Category: 56724-03-9

Comins, Daniel L.; Brown, Jack D. published the artcile< Ortho substitution of m-anisaldehyde via α-amino alkoxide directed lithiation>, Safety of 3-Methoxy-2-methylbenzaldehyde, the main research area is ortho substitution anisaldehyde; amino alkoxide directed lithiation; regioselective lithiation anisaldehyde; methylation anisaldehyde regioselective; methylanisaldehyde.

The directed lithiation of α-amino alkoxides derived from 3-MeOC6H4CHO (I) was studied. The α-amino alkoxides were formed in situ by the addition of I to N-MeLiNCH2CH2NMe2, MeLiNNMe2 or lithium N-methylpiperazide. Several lithiation-methylation reactions of the in situ formed α-amino alkoxides were performed and the products analyzed for 2,3-, 6,3- and 4,3-Me(MeO)C6H3CHO and I. Mixtures of products were obtained in several cases. A highly regioselective directed lithiation occurred at C(2) in C6H6 or PhMe in the presence of MeLiNNMe2 and PhLi. In this manner, 2,3-Me(MeO)C6H3CHO of 96% purity was prepared in 1 step from I in 91% yield.

Journal of Organic Chemistry published new progress about Lithiation, regioselective. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Safety of 3-Methoxy-2-methylbenzaldehyde.

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

Hendrikse, Erica R.; Liew, Lydia P.; Bower, Rebekah L.; Bonnet, Muriel; Jamaluddin, Muhammad A.; Prodan, Nicole; Richards, Keith D.; Walker, Christopher S.; Pairaudeau, Garry; Smith, David M.; Rujan, Roxana-Maria; Sudra, Risha; Reynolds, Christopher A.; Booe, Jason M.; Pioszak, Augen A.; Flanagan, Jack U.; Hay, Michael P.; Hay, Debbie L. published the artcile< Identification of Small-Molecule Positive Modulators of Calcitonin-like Receptor-Based Receptors>, Name: 3-Methoxy-2-methylbenzaldehyde, the main research area is adrenomedullin CLR calcitonin peptide RAMP allosteric modulator GPCRs.

Class B G protein-coupled receptors are highly therapeutically relevant but challenges remain in identifying suitable small-mol. drugs. The calcitonin-like receptor (CLR) in particular is linked to conditions such as migraine, cardiovascular disease, and inflammatory bowel disease. The CLR cannot act as a cell-surface receptor alone but rather must couple to one of three receptor activity-modifying proteins (RAMPs), forming heterodimeric receptors for the peptides adrenomedullin and calcitonin gene-related peptide. These peptides have extended binding sites across their receptors. This is one reason why there are few small-mol. ligands that can modulate these receptors. Here we describe small mols. that are able to pos. modulate the signaling of the CLR with all three RAMPs but are not active at the related calcitonin receptor. These compounds were selected from a β-arrestin recruitment screen, coupled with rounds of medicinal chem. to improve their activity. Translational potential is shown as the compounds can pos. modulate cAMP signaling in a vascular cell line model. Binding experiments do not support an extracellular domain binding site; however, mol. modeling reveals potential allosteric binding sites in multiple receptor regions. These are the first small-mol. pos. modulators described for the CLR:RAMP complexes.

ACS Pharmacology & Translational Science published new progress about Adrenomedullin receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Name: 3-Methoxy-2-methylbenzaldehyde.

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

Comins, Daniel L.; Brown, Jack D. published the artcile< Ortho metalation directed by α-amino alkoxides>, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde, the main research area is metalation ortho amino alkoxide directed; lithiation ortho amino alkoxide directed; regiochemistry lithiation ortho aromatic aldehyde.

Adding benzaldehydes and naphthaldehydes to Li dialkylamides gave α-amino alkoxides, which were ortho-lithiated with excess BuLi and then alkylated and hydrolyzed to give o-substituted aromatic aldehydes. Using Me2NCH2CH2NHMe as the amine gave metalation at lower temperatures due to intramol. amine-assisted metalation. The synthetic utility of this ortho metalation, including how varying the amine component of the α-amino alkoxide affects the regiochem. and metalation rate, was discussed.

Journal of Organic Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde.

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

Kende, Andrew S.; Curran, Dennis P. published the artcile< Regiochemical control in dihydrophenanthrene synthesis. A photochemical total synthesis of juncusol>, Related Products of 56724-03-9, the main research area is juncusol total synthesis; phenanthrenediol dihydrodimethylvinyl Juncus total synthesis; regiochem cyclization vinylphenylbenzyl alc.

Three approaches are described toward the total synthesis of juncusol (I), a cytotoxic constituent of the needlerush Juncus roemerianus. Wittig condensation of the phosphonium salt derived from 2-methyl-3-methoxybenzyl bromide with 3-methoxy-4-methyl-5-cyanobenzaldehyde gave a mixture of cyanostilbenes, (E)- and (Z)-2,3-Me(MeO)C6H3CH:CHC6H2(CN)(OMe)Me-3,5,4. Reduction of this mixture gave the diarylethane, which failed to undergo oxidative aryl-aryl cyclization. Photocyclization of the stilbenes gave a 7:1 mixture of phenanthrenes in which the unwanted 7-cyano regioisomer predominated. The Ziegler modification of the Ullmann coupling was used to prepare the sym. dialdehyde II, which underwent successive Wittig reaction with Ph3P:CH2 and hydride reduction to give the key intermediate III. Photocyclization of III gave a dihydrophenanthrene alc. which underwent successive oxidation to an aldehyde, Wittig condensation with Ph3P:CH2, and demethylation to give I. The overall yield of I from 2-methyl-3-methoxybenzaldehyde is 18% over 10 steps; the route provides the first total synthesis of this natural product.

Journal of the American Chemical Society published new progress about Juncus roemerianus. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Related Products of 56724-03-9.

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

Bezencon, Olivier; Bur, Daniel; Weller, Thomas; Richard-Bildstein, Sylvia; Remen, Lubos; Sifferlen, Thierry; Corminboeuf, Olivier; Grisostomi, Corinna; Boss, Christoph; Prade, Lars; Delahaye, Stephane; Treiber, Alexander; Strickner, Panja; Binkert, Christoph; Hess, Patrick; Steiner, Beat; Fischli, Walter published the artcile< Design and Preparation of Potent, Nonpeptidic, Bioavailable Renin Inhibitors>, SDS of cas: 56724-03-9, the main research area is aryl substituted diazabicyclononenecarboxamide preparation selective renin inhibitor antihypertensive; potent nonpeptidic bioavailable diazabicyclononenecarboxamide renin inhibitor; structure aryl substituted diazabicyclononenecarboxamide inhibition renin; mol crystal structure renin bound nonracemic aryloxyethylphenyl diazabicyclononenecarboxamide.

Aryl-substituted diazabicyclononenecarboxamides such as I are prepared as selective human renin inhibitors for potential use as antihypertensive agents. Aryl substituents and the carboxamide moiety of the diazabicyclononenecarboxamides are essential for selective binding to renin; attachment of a substituent to the methyleneaminomethylene bridge of the diazabicyclononenecarboxamides does not modify the binding affinity but alters the pharmacokinetics of the product. I inhibits renin with an IC50 of 0.20 nM in buffer and 19 nM in plasma; a 10 mg/kg dose of I lowers the blood pressures of transgenic rats over a period of 36 h. The structures of both enantiomers of an aryloxyethylphenyl diazabicyclononenecarboxamide sep. bound to human renin are determined by X-ray crystallog.

Journal of Medicinal Chemistry published new progress about Antihypertensives. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, SDS of cas: 56724-03-9.

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

Gilmartin, Philip H.; Kozlowski, Marisa C. published the artcile< Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products>, HPLC of Formula: 56724-03-9, the main research area is vanadium catalyzed oxidative intramol coupling tethered phenol dienone.

A mild and efficient method for the vanadium-catalyzed intramol. coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.

Organic Letters published new progress about Biomimetic synthesis. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, HPLC of Formula: 56724-03-9.

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

Cho, Hyunkyung; Jeon, Hongjun; Shin, Jae Eui; Lee, Seokwoo; Park, Soojun; Kim, Sanghee published the artcile< Asymmetric synthesis of Cα-substituted prolines through Curtin-Hammett-controlled diastereoselective N-alkylation>, Safety of 3-Methoxy-2-methylbenzaldehyde, the main research area is substituted proline enantioselective diastereoselective synthesis chirality transfer Stevens rearrangement; amino acid proline ester alkylation substituted benzyl; alkylation mechanism Curtin Hammett principle DFT transition state; crystal structure substituted proline quaternization free energy steric effect; Curtin-Hammett principle; chirality transfer; proline derivatives; rearrangement; stereoselectivity.

Asym. synthesis of α-substituted proline derivatives has been accomplished by an efficient chirality-transfer method. High diastereoselectivity of the N-alkylation of the proline ester (C→N chirality transfer) was achieved when a 2,3-disubstituted benzyl group was used as the N-substituent. DFT calculations provided a mechanistic rationale for the high degree of stereoselectivity. The generated N-chirality of the quaternary ammonium salt was transferred back to the α-carbon through a stereoselective [2,3]-Stevens rearrangement (N→C chirality transfer) to give α-substituted proline ester.

Chemistry – A European Journal published new progress about Alkylation, stereoselective. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Safety of 3-Methoxy-2-methylbenzaldehyde.

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

Xiao, Peihong; Tang, Zhixing; Wang, Kai; Chen, Hua; Guo, Qianyou; Chu, Yang; Gao, Lu; Song, Zhenlei published the artcile< Chemoselective Reduction of Sterically Demanding N,N-Diisopropylamides to Aldehydes>, HPLC of Formula: 56724-03-9, the main research area is aldehyde preparation sterically demanding diisopropylamide chemoselective reduction.

A sequential one-pot process for chemoselectively reducing sterically demanding N,N-diisopropylamides to aldehydes has been developed. In this reaction, amides are activated with EtOTf to form imidates, which are reduced with LiAlH(OR)3 [R = t-Bu, Et] to give aldehydes by hydrolysis of the resulting hemiaminals. The non-nucleophilic base 2,6-DTBMP remarkably improves reaction efficiency. The combination of EtOTf/2,6-DTBMP and LiAlH(O-t-Bu)3 was found to be optimal for reducing alkyl, alkenyl, alkynyl, and 2-monosubstituted aryl N,N-diisopropylamides. In contrast, EtOTf and LiAlH(OEt)3 in the absence of base were found to be optimal for reducing extremely sterically demanding 2,6-disubstituted N,N-diisopropylbenzamides. The reaction tolerates various reducible functional groups, including aldehyde and ketone. 1H NMR studies confirmed the formation of imidates stable in water. The synthetic usefulness of this methodol. was demonstrated with N,N-diisopropylamide-directed ortho-metalation and C-H bond activation.

Journal of Organic Chemistry published new progress about Aldehydes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, HPLC of Formula: 56724-03-9.

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

Flippin, Lee A.; Muchowski, Joseph M.; Carter, David S. published the artcile< Directed metalation of aromatic aldimines with lithium 2,2,6,6-tetramethylpiperidide>, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde, the main research area is lithiation aromatic aldimine lithium tetramethylpiperidide; piperidide lithiotetramethyl lithiation aldimine; benzaldehyde methyl.

N-Cyclohexyl aromatic aldimines are ortho-lithiated or o-methyl-lithiated with 2 equiv of lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF solution at -15°. The lithiated intermediates generally reacted with alkyl halides or CO2 to provide ortho-functionalized aldimine products which could be readily converted to the corresponding aldehydes by hydrolysis with aqueous 4 M HCl. Aromatic aldimines derived from (±)-trans-2-methylcyclohexylamine or 3-amino-2,4-dimethylpentane are resistant toward C=N addition with 1 equiv of n-BuLi at 0° in THF solution; however, they are also surprisingly resistant toward directed metalation reactions with either LTMP or n-BuLi. Exceptions to the ortho-directing and o-methyl-directing effects of the aldimine group were observed in a reaction of 3-methylthiophene-2-carboxaldehyde cyclohexylimine with LTMP, followed by CH3I, which gave a 9:1 mixture of 3,5-dimethylthiophene-2-carboxaldehyde cyclohexylimine and 5-ethyl-3-methylthiophene-2-carboxaldehyde cyclohexylimine, and a reaction of p-tolualdehyde 2,4-dimethylpent-3-ylimine with either n-BuLi or LTMP, followed by CH3I, which gave p-ethylbenzaldehyde 2,4-dimethylpent-3-ylimine.

Journal of Organic Chemistry published new progress about Aldimines Role: RCT (Reactant), RACT (Reactant or Reagent). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde.

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

Leed, Andrew R.; Boettger, Susan D.; Ganem, Bruce published the artcile< Studies on the synthesis of substituted phenanthrenoids>, Reference of 56724-03-9, the main research area is juncusol; phenanthrene substituted; halogenation regioselective benzene.

Highly regioselective reactions for the construction of polysubstituted benzenes I (R = H, Me, SiMe2CMe3; R1, R2 = H, Br) and II (R3 = CO2H, CH2OH, CH2Br, CH2PPh3Br) are described, including some remarkable site-selective halogenations. These were used to prepare halo-, nitro-, amino-, and urethane-substituted stilbenes e.g., (E)-III (R4 = NO2, NH2, NHCO2Et; R5, R6 = H, iodo). Thermal as well as photochem. cyclizations were attempted. Stilbene III (R4 = NO2, R5 = H, R6 = iodo) gave the IV (R7 = H, Br; R8 = NO2, NH2); likewise III (R4 = NHCO2Et, R5 = H, R6 = iodo) furnished two new tricyclics, IV (R7 = Br; R8 = NH2, NHCO2Et), whereas irradiation of III (R4 = NHCO2Et, R5 = R6 = H) in HOCMe3 captured solvent to produce phenanthrenes IV (R7 = NHCO2Et; R8 = OH, OCMe3). Strategies for the total synthesis of juncusol (V), a cytotoxic phytoalexin, are considered.

Journal of Organic Chemistry published new progress about Halogenation, regioselective. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Reference of 56724-03-9.

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