Category: 100927-02-4

Efficient and enantioselective total syntheses of heliannuols A and K was written by Kanematsu, Makoto;Soga, Kana;Manabe, Yuki;Morimoto, Sachie;Yoshida, Masahiro;Shishido, Kozo. And the article was included in Tetrahedron in 2011.Product Details of 100927-02-4 The following contents are mentioned in the article:

The second-generation enantioselective synthesis of (-)-heliannuol A (I) and the first enantioselective total synthesis of (-)-heliannuol K (II) via two routes have both been accomplished efficiently; (I, nine steps and 25% yield; II, seven steps and 47% yield). Highlights of our synthetic strategy include a substrate-controlled chirality transfer in the Lewis acid mediated Claisen rearrangement of the allyl aryl ether for the key construction of a tertiary stereogenic center at the benzylic position followed by, for I, ring-closing metathesis, diastereoselective epoxidation, and regioselective cleavage of the epoxide; and for II, ring-closing metathesis and conjugate reduction of the eight-membered enone. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Product Details of 100927-02-4).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Product Details of 100927-02-4

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Total synthesis of heliannuol B, an allelochemical from Helianthus annuus was written by Roy, Amalesh;Biswas, Bidyut;Sen, Prabir K.;Venkateswaran, Ramanathapuram V.. And the article was included in Tetrahedron Letters in 2007.Application In Synthesis of 4-(Benzyloxy)-3-methylphenol The following contents are mentioned in the article:

A total synthesis of the allelochem. heliannuol B (I) is described employing ring closing metathesis to generate the central benzoxepane ring system. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Application In Synthesis of 4-(Benzyloxy)-3-methylphenol).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Application In Synthesis of 4-(Benzyloxy)-3-methylphenol

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Studies towards the conception of new selective PPARβ/δ ligands was written by Ekambome Bassene, Carine;Suzenet, Franck;Hennuyer, Nathalie;Staels, Bart;Caignard, Daniel-Henri;Dacquet, Catherine;Renard, Pierre;Guillaumet, Gerald. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2006.Synthetic Route of C14H14O2 The following contents are mentioned in the article:

In order to define new PPARβ/δ ligands, SAR study on the selective PPARβ/δ activator L-165,041 led to the identification of one key functional group for selective PPARβ/δ activation. Furthermore, taking advantage of SAR studies done elsewhere on the most selective PPARβ/δ ligand GW501516, the conception of new ligands showing good affinity for PPARβ/δ is reported. Finally, synthesis and biol. evaluation of pyridine analogs have shown the beneficial effect of the pyridine ring on the PPARβ/δ subtype selectivity. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Synthetic Route of C14H14O2).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Synthetic Route of C14H14O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Studies towards the conception of new selective PPARβ/δ ligands was written by Ekambome Bassene, Carine;Suzenet, Franck;Hennuyer, Nathalie;Staels, Bart;Caignard, Daniel-Henri;Dacquet, Catherine;Renard, Pierre;Guillaumet, Gerald. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2006.Synthetic Route of C14H14O2 The following contents are mentioned in the article:

In order to define new PPARβ/δ ligands, SAR study on the selective PPARβ/δ activator L-165,041 led to the identification of one key functional group for selective PPARβ/δ activation. Furthermore, taking advantage of SAR studies done elsewhere on the most selective PPARβ/δ ligand GW501516, the conception of new ligands showing good affinity for PPARβ/δ is reported. Finally, synthesis and biol. evaluation of pyridine analogs have shown the beneficial effect of the pyridine ring on the PPARβ/δ subtype selectivity. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Synthetic Route of C14H14O2).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Synthetic Route of C14H14O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Discovery of novel brain permeable and G protein-biased beta-1 adrenergic receptor partial agonists for the treatment of neurocognitive disorders was written by Yi, Bitna;Jahangir, Alam;Evans, Andrew K.;Briggs, Denise;Ravina, Kristine;Ernest, Jacqueline;Farimani, Amir B.;Sun, Wenchao;Rajadas, Jayakumar;Green, Michael;Feinberg, Evan N.;Pande, Vijay S.;Shamloo, Mehrdad. And the article was included in PLoS One in 2017.Product Details of 100927-02-4 The following contents are mentioned in the article:

The beta-1 adrenergic receptor (ADRB1) is a promising therapeutic target intrinsically involved in the cognitive deficits and pathol. features associated with Alzheimer’s disease (AD). Evidence indicates that ADRB1 plays an important role in regulating neuroinflammatory processes, and activation of ADRB1 may produce neuroprotective effects in neuroinflammatory diseases. Novel small mol. modulators of ADRB1, engineered to be highly brain permeable and functionally selective for the G protein with partial agonistic activity, could have tremendous value both as pharmacol. tools and potential lead mols. for further preclin. development. The present study describes our ongoing efforts toward the discovery of functionally selective partial agonists of ADRB1 that have potential therapeutic value for AD and neuroinflammatory disorders, which has led to the identification of the mol. STD-101-D1. As a functionally selective agonist of ADRB1, STD-101-D1 produces partial agonistic activity on G protein signaling with an EC50 value in the low nanomolar range, but engages very little beta-arrestin recruitment compared to the unbiased agonist isoproterenol. STD-101-D1 also inhibits the tumor necrosis factor α (TNFα) response induced by lipopolysaccharide (LPS) both in vitro and in vivo, and shows high brain penetration. Other than the therapeutic role, this newly identified, functionally selective, partial agonist of ADRB1 is an invaluable research tool to study mechanisms of G protein-coupled receptor signal transduction. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Product Details of 100927-02-4).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Product Details of 100927-02-4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

β(4-Hydroxy-2-methylphenoxy)lactic acid, a metabolite of mephenesin was written by Ludwig, B. J.;Luts, H.;West, W. A.. And the article was included in Journal of the American Chemical Society in 1955.Recommanded Product: 4-(Benzyloxy)-3-methylphenol The following contents are mentioned in the article:

2,1,4-MeC₆H₃(OH)₂ (I) (24.8 g.) in 8.0 g. NaOH in 100 cc. H₂O, the mixture refluxed 2 hrs. with 12.5 g. ClCH₂CH(OH)CO₂H (II), cooled, saturated with CO₂, and washed with Et₂O to recover 19.5 g. unchanged I, the aqueous layer concentrated in vacuo, acidified with HCl, and extracted with Et₂O, the extract evaporated, the residue (2.6 g.) sublimed in vacuo to remove unchanged I, and the tan-colored, solid residue (1.5 g.) recrystallized repeatedly from hot PrNO₂ gave 3,4-Me(HO)C₆H₃OCH₂CH(OH)CO₂H, slightly colored crystals, m. 121-2°. Dihydropyran (16.8 g.) added with stirring to 12.4 g. I in 100 cc. dioxane containing 2 drops concentrated HCl at 25-30°, the mixture allowed to warm to 60°, and diluted with Et₂O, the organic layer extracted with 10% aqueous NaOH, the alk. solution neutralized with CO₂, diluted with H₂O, and extracted with CCl₄, the extract evaporated, and the colored residue (5.3 g.) recrystallized from Et₂O-ligroine containing a drop dihydropyran gave 4- hydroxy-3-methylphenyl-2-tetrahydropyranyl ether (III), white crystals, m. 90-1.5°. III (4.16 g.) in 12 g. 10% aqueous NaOH refluxed 3 hrs. with 1.25 g. II, the solution cooled, saturated with CO₂, and extracted with Et₂O, the aqueous portion acidified with HCl, saturated with Na₂SO₄, and extracted with Et₂O, the extract dried and evaporated, and the colored, solid residue (0.8 g.) recrystallized twice from C₆H₆-Et₂O and once from PrNO₂ gave 410 mg. 2,4-Me(HO)C₆H₃OCH₂CH(OH)CO₂H (IV), m. 168-9°. Synthetic and natural IV were identical with regard to their m.p., ultraviolet absorption, color test with Ehrlich reagent, and chromatographic behavior on paper. III (1.04 g.) treated in the usual manner with 1 equivalent PhCH₂Cl in 1 equivalent aqueous NaOH, the intermediate mixed diether hydrolyzed, and the mixture worked up in the usual manner gave a small amount of 2,5-PhCH₂(HO)C₆H₃Me, white crystals, m. 69.5-70.5°. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Recommanded Product: 4-(Benzyloxy)-3-methylphenol).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Recommanded Product: 4-(Benzyloxy)-3-methylphenol

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reactions with halogen-substituted xanthones. II was written by Mustafa, Ahmed;Asker, Wafia;Sobhy, Mohamed Ezz El-Din. And the article was included in Journal of the American Chemical Society in 1955.Product Details of 100927-02-4 The following contents are mentioned in the article:

The reduction of halogen-substituted xanthones with LiAlH₄ and with metallic Na and EtOH led to the formation of xanthene (I) with loss of the halogen. The reduction of xanthone (II) to I with LiAlH₄ is discussed. 1-Chloro-(III), 1-6-dichloro-4-methylxanthone (IV), and 1-chloro-4-methylthiaxanthone (V) condense with aromatic thiols in the presence of KOH to yield the corresponding arylmercapto derivatives which are oxidized readily to the corresponding sulfone derivatives Whereas 2-chloroxanthone (VI) undergoes a photochem. addition reaction with I in sunlight to give the carbinol VII, the 4-isomer (VIII) of VI effects the photochem. dehydrogenation of I to 9,9′-bixanthene (IX). 2-Chloro-9-phenylxanthone (X) undergoes a photochem. oxidation in sunlight in the presence of O, yielding the peroxide (XI) of X. VI (1 g.) in 30 cc. C₆H₆ added in portions to 0.7 g. LiAlH₄ in 50 cc. Et₂O, the mixture refluxed 3 h., kept at room temperature overnight, and treated with cold dilute HCl, the Et₂O layer worked up, and the solid residue washed with about 40 cc. petr. ether and recrystallized from MeOH gave almost quant. I. The 4-isomer (XII) and the 2-Br (XIII) and 4-Br (XIV) analogs of VI gave identical results. III (1 g.) treated with LiAlH₄ in the usual manner, the mixture refluxed 2 h., decomposed with about 100 cc. cold saturated aqueous NH₄Cl, and extracted with Et₂O, the extract dried and evaporated, and the solid residue recrystallized from C₆H₆ and light petr. yielded about 0.73 g. 1-chloro-4-methylxanthydrol, colorless crystals, m. 170° (yellow melt). VI, XII, XIII, and XIV (1 g. each) in 25 cc. hot absolute EtOH added dropwise to 1 g. molten metallic Na by the method of Heller and Kostanecki (C.A. 2, 2243), the mixture steam distilled, and the resulting solid recrystallized from MeOH gave an almost quant. yield of I, m. 101°, in each case. III, IV, V (2 g. each) and 1.5 g. of the appropriate thiol in 25 cc. AmOH treated with 0.1 g. solid KOH, the mixture refluxed 3 h., held at room temperature overnight, and filtered, the filter residue washed with cold EtOH, H₂O, and cold Me₂CO, and extracted with about 60 cc. ligroine (b. 60-80°), and the residue crystallized from glacial AcOH gave the corresponding 1-arylmercapto-4-methylxanthones and -thiaxanthones. In this manner were obtained the following compounds (m.p. and % yield given): 1-(o-tolylmercapto)4-methylxanthones (XV), 170°, 52; the m-isomer, 163°, 58; the p-isomer of XV, 166°, 73; 1-phenylmercapto-6-chloro-4-methylxanthone (XVI), 164°, 81; the o-Me derivative of XVI, 205°, 62; m-Me derivative of XVI, 140°, 58; p-Me derivative of XVI, 180°, 78; 1-phenylmercapto-4-methylthiaxanthone (XVII), 150°, 83°; o-Me derivative of XVII, 162°, 64; m-Me derivative of XVII, 140°, 61; p-Me derivative of XVII, 164°, 84; all compounds formed yellow crystals and gave an orange-red color with H₂SO₄. The appropriate arylmercapto-4-methylxanthone or -thiaxanthone (1 g.) in 25 cc. glacial AcOH treated with 5 cc. 30% H₂O₂, the mixture heated 1 h. on the steam bath and held at room temperature overnight, and the resulting crystallized deposit recrystallized from glacial AcOH gave the corresponding sulfones (mercapto compound used, m.p., and % yield given): XV, 260°, 63; m-isomer of XV, 226°, 61; p-isomer of XV, 270°, 76; XVI, 210-12°, 84; o-Me derivative of XVI, 242°, 73; m-Me derivative of XVI, 198°, 69; p-Me derivative of XVI, 240°, 79; XVII, 176°, 82; o-Me derivative of XVII, 180°, 75; m-Me derivative of XVII, 182°, 70; p-Me derivative of XVIII, 210°, 85. I (1 g.) and 1.3 g. VI in 30 cc. C₆H₆ exposed 10 days (May) to sunlight and the resulting colorless needles washed with about 10 cc. C₆H₆ and recrystallized from hot C₆H₆ yielded about 80% VII, m. 174°; it dissolved with difficulty with an orange color in concentrated H₂SO₄. VIII (0.7 g.) and 0.5 g. I in 25 cc. C₆H₆ exposed 10 days (July) to sunlight, the C₆H₆ removed in vacuo, the oily residue cooled, and the semisolid mass washed with about 25 cc. petr. ether (b. 50-60°) and recrystallized from C₆H₆ yielded about 0.32 g. IX, m. 201°. The Grignard solution from 0.9 g. Mg and 9 g. PhBr in 50 cc. dry Et₂O treated with 1 g. VI in 50 cc. dry C₅H₆, the Et₂O evaporated, the residual mixture heated 1 h. on the steam bath, kept at 25° overnight, and poured slowly into 100 cc. saturated aqueous NH₄Cl, the Et₂O layer dried, filtered, and evaporated, the oily residue washed with about 35 cc. petr. ether below 40°, and the resulting solid crystallized from ligroine gave about 0.87 g. 2-chloro-9-phenylxanthydrol, m. 113°; it gave an orange color with H₂SO₄; it gave reduced with Zn dust and AcOH almost 100% X, colorless crystals, m. 139° (from EtOH). X (1 g.) in solution exposed 15 days (Apr.) to sunlight gave about 0.63 g. XI, m. 221° (decomposition) (brown-red melt); it gave an orange-yellow color with H₂SO₄. XI (0.5 g.) heated 0.5 h. at 270° yielded 0.18 g. xanthone. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Product Details of 100927-02-4).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Product Details of 100927-02-4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Elbs persulfate oxidation of phenols and its adaptation to the preparation of monoalkyl ethers of quinols was written by Baker, Wilson;Brown, N. C.. And the article was included in Journal of the Chemical Society in 1948.Synthetic Route of C14H14O2 The following contents are mentioned in the article:

The oxidation of phenols to hydroquinones by K₂S₂O₈ in alk. medium is termed “Elbs K₂S₂O₈ oxidation” [cf. J. prakt. Chem. 48, 179(1893)]. The phenol (1 mol.) in 5 mols. 10% NaOH is oxidized by the slow addition (3-4 h.) of aqueous saturated K₂S₂O₈ (temperature not above 20°); after standing overnight, the solution is acidified (Congo red), extracted with ether, the aqueous layer treated with excess HCl, heated 0.5 h. on a water bath, cooled, and extracted with ether. The following give the recovered phenol and the yield of oxidation product on the basis of unrecovered phenol (%): PhOH to p-C₆H₄(OH)₂ 48, 34; ο-HOC₆H₄CHO to 2,5-(HO)₂C₆H₃CHO 24, 33; 1,3,5-Me₂C₆H₃OH to 2,6,1,4-Me₂C₆H₂(OH)₂ (I) 30, 51; 1,3,2-Me₂C₆H₃OH (II) to I 26, 40; 2,5-Me₂C₆H₃OH to 2,5,1,4-Me₂C₆H₂(OH)₂ 25, 56; ο-ClC₆H₄OH to 2,1,4-ClC₆H₃(OH)₂ 20, 62; p-MeC₆H₄OH to 3,4-(HO)₂C₆H₃Me 20, 11; vanillin to 5,3,4-MeO(HO)₂C₆H₂CHO 48, 3.6; p-HOC₆H₄CO₂H to 3,4-(HO)₂C₆H₃CO₂H 71, 2. Some of the yields can be improved by isolation of the intermediate sulfate but this involves evaporation of large volumes of solution 2,6,4-Me₂(HO)C₆H₂OSO₃K (from II) (25 g.) in 60 cc. 90% EtOH and 50 cc. H₂O containing 7 g. NaOH, treated (0.25 h.) at the b.p. with 14 g. PhCH₂Cl and refluxed an addnl. 2 h., gives 22 g. 5-(benzyloxy)-m-2-xylenol, m. 97-9°. ο-HOC₆H₄Me (21 g.) gives 27 g. of the K SO₄ salt, which with Me₂SO₄ and NaOH yields 27% 5,2-HO(MeO)C₆H₃Me; the m-isomer gives 34% 2,5-HO(MeO)C₆H₃Me. ο-HOC₆H₄Me yields 2-(benzyloxy)-5-hydroxytoluene, m. 69-70°; the 5-Me ether b_0.5 135-8° and with HCl yields 2,5-HO(MeO)C₆H₃Me. II gives 2-methoxy-m-5-xylenol, m. 83°. This study involved multiple reactions and reactants, such as 4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4Synthetic Route of C14H14O2).

4-(Benzyloxy)-3-methylphenol (cas: 100927-02-4) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Synthetic Route of C14H14O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem