Tag: M.W=150-200

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

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

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

Kim, Byung Hyun; Lee, Jong Gil; Kim, Woon Ki; Kim, Young Gyu published the artcile< Regioselective Synthesis of 2,6-Dimethyltetralin: Key Precursor to 2,6-Dimethylnaphthalene>, Quality Control of 52244-70-9, the main research area is tetralin dimethyl regioselective preparation; naphthalene dimethyl regioselective preparation; tetrahydronaphthalene regioselective preparation; alc arylbutyl preparation intramol Friedel Crafts alkylation.

A novel regioselective synthesis for 2,6-dimethyltetralin (2,6-DMT), a key precursor to 2,6-dimethylnaphthalene (2,6-DMN), is described. The synthesis comprises the following three steps; the Heck reaction between com. available 4-bromotoluene and 3-methyl-3-buten-1-ol, the catalytic reduction of the coupling products, and the acid-catalyzed cyclization of the alc. intermediate. The process has an advantage over the established processes in that 2,6-DMT is obtained as the only isomer, and the isomerization and/or the complicated separation and purification steps are not required to produce pure 2,6-DMT. 2,6-DMN could be also obtained as a major product depending on the cyclization conditions.

Organic Process Research & Development published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Quality Control of 52244-70-9.

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

Kosui, Nobuo; Waki, Michinori; Kato, Tetsuo; Izumiya, Nobuo published the artcile< Preparation of homologs of L-2-amino-5-(p-methoxyphenyl)pentanoic acid>, Quality Control of 52244-70-9, the main research area is aminoalkanoic acid anisyl; anisylalkanoic acid amino; butanoic acid aminoanisyl; hexanoic acid aminoanisyl; resolution acetamidoanisylalkanoic acid deacetylation; enzyme resolution acetamidoanisylalkanoic acid.

L-p-MeOC6H4(CH2)nCH(NH2)CO2H (n = 2, 4) were prepared by optical resolution of their N-acetyl derivatives with Aspergillus acylase. The N-acetyl derivatives were synthesized from p-MeO6H4(CH2)nC(NHAc)(CO2H)2 by heating with p-xylene.

Bulletin of the Chemical Society of Japan published new progress about 52244-70-9. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Quality Control of 52244-70-9.

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

Zheng, Guangrong; Smith, Andrew M.; Huang, Xiaoqin; Subramanian, Karunai L.; Siripurapu, Kiran B.; Deaciuc, Agripina; Zhan, Chang-Guo; Dwoskin, Linda P. published the artcile< Structural Modifications to Tetrahydropyridine-3-carboxylate Esters en Route to the Discovery of M5-Preferring Muscarinic Receptor Orthosteric Antagonists>, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol, the main research area is tetrahydropyridine carboxylate ester preparation muscarinic receptor drug abuse.

The M5 muscarinic acetylcholine receptor is suggested to be a potential pharmacotherapeutic target for the treatment of drug abuse. We describe herein the discovery of a series of M5-preferring orthosteric antagonists based on the scaffold of 1,2,5,6-tetrahydropyridine-3-carboxylic acid. Compound 56, the most selective compound in this series, possesses an 11-fold selectivity for the M5 over M1 receptor and shows little activity at M2-M4. This compound, although exhibiting modest affinity (Ki = 2.24 μM) for the [3H]N-methylscopolamine binding site on the M5 receptor, is potent (IC50 = 0.45 nM) in inhibiting oxotremorine-evoked [3H]DA release from rat striatal slices. Further, a homol. model of human M5 receptor based on the crystal structure of the rat M3 receptor was constructed, and docking studies of compounds 28 and 56 were performed in an attempt to understand the possible binding mode of these novel analogs to the receptor.

Journal of Medicinal Chemistry published new progress about Drugs of abuse. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol.

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

Liu, Jie; Xiang, Haonan; Jiang, Lvqi; Yi, Wenbin published the artcile< Chemoselective desulfurization-fluorination/bromination of carbonofluoridothioates for the O-trifluoromethylation and O-bromodifluoromethylation of alcohols>, Electric Literature of 52244-70-9, the main research area is carbonofluoridothioate preparation desulfurization fluorination bromination; bromodifluoromethyl ether alkyl preparation chemoselective; alkyl trifluoromethyl ether preparation chemoselective; alc trifluoromethylation.

Herein, a method for synthesizing various alkyl trifluoromethyl e.g., C6H5(CH2)5OCF3 and alkyl bromodifluoromethyl ethers e.g., C6H5(CH2)5OCF2Br using carbonofluoridothioates e.g., C6H5(CH2)5OC(S)F as precursors has been described. Carbonofluoridothioates were obtained upon the reaction of an alc. e.g., C6H5(CH2)5OH and S=CF2 generated via the decomposition of an SCF3 anion, and then selectively transformed into their corresponding trifluoromethyl and bromodifluoromethyl ethers upon changing the reaction conditions. This transformation has also been extended to the one-pot, two-step conversion of alcs. into alkyl trifluoromethyl ethers. A series of alkyl bromodifluoromethyl ethers has also been synthesized. These compounds open up a new avenue for the synthesis of a wide range of useful fluorinated products. In addition, this method is suitable for the late-stage introduction of trifluoromethyl ethers in complex small mols.

Science China: Chemistry published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Electric Literature of 52244-70-9.

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

Hansen, N. C. published the artcile< Monoalkylsulfamyl chlorides>, Electric Literature of 10305-42-7, the main research area is .

Normal C2-5 amine hydrochlorides were treated with excess SO2Cl2 18 hrs. on a water bath at 75°. In some cases more SO2Cl2 was added. The resulting oil was treated with dry ether, the precipitated amine hydrochloride filtered off, and the filtrate distilled in vacuo to give monoalkylsulfamyl chlorides, RNHSO2Cl (I). [RNH2.HCl (R given), amount added, and recovered (g.), volume (ml.) SO2Cl2 used, % yield of corresponding I (based on RNH2.HCl used) and b.p. (redistilled samples) given]: Et, 52, 23, 105 (a further 100 ml. was added after 4 hrs. reflux), 42, b0.05 52; Pr, 52, 26, 350, 13, b0.2 78°; Bu, 77, 27, 450, 39, b0.11 80°; and Am, 19, 12, 150, 8, b0.15 95°. When HCl salts of methyl-, hexyl-, cyclohexyl-, and octylamine were used, the yields of the corresponding I were too low to permit their isolation. That at least MeNHSO2Cl was formed could be concluded from the fact that MeNHSO2NHPr, m. 57-8° (ether-petr. ether), could be obtained when the impure product was treated with PrNH2. EtNHSO2NHBu, m. 73-5° (hexane), was similarly obtained from EtNHSO2Cl.

Acta Chemica Scandinavica published new progress about NMR (nuclear magnetic resonance). 10305-42-7 belongs to class ethers-buliding-blocks, and the molecular formula is C3H8ClNO2S, Electric Literature of 10305-42-7.

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

Poon, Kevin W. C.; Dudley, Gregory B. published the artcile< Mix-and-Heat Benzylation of Alcohols Using a Bench-Stable Pyridinium Salt>, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol, the main research area is alc benzylation pyridinium triflate; ether benzyl preparation.

2-Benzyloxy-1-methylpyridinium triflate (I) is a stable, neutral organic salt that converts alcs. into benzyl ethers upon warming. The synthesis and reactivity of I are described herein. Benzylation of a wide range of alcs. occurs in good to excellent yields.

Journal of Organic Chemistry published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol.

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