(E)-methyl 3-(6-methylpyridin-2-yl)acrylate | 853179-80-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-methyl 3-(6-methylpyridin-2-yl)acrylate
• 英文别名: (E)-methyl 3-(6-methylpyridine-2-yl)acrylate；2-Propenoic acid, 3-(6-methyl-2-pyridinyl)-, methyl ester；methyl (E)-3-(6-methylpyridin-2-yl)prop-2-enoate
• CAS: 853179-80-3
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: RERVJXIHGQMDCR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(6-methylpyridin-2-yl)acrylate 在 sodium hydroxide 、 正丁基锂 、 氢溴酸 、 羟胺 、 溴 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.67h， 生成 3-Methoxy-5-(6-methyl-2-pyridinyl)-4-isoxazolemethanol
  参考文献：
  名称：

  AMPA的杂芳基类似物。2.合成，绝对立体化学，光化学和结构活性关系。

  摘要：

  先前我们已经表明（S）-2-氨基-3-（3-羟基-5-苯基-4-异恶唑基）丙酸[（S）-APPA，2]是（RS）-2-的弱激动剂氨基-3-（3-羟基-5-甲基-4-异恶唑基）丙酸（AMPA）受体，被（S）-AMPA（1）特异性激活，而（S）-2-氨基-3- [3-羟基-5-（2-吡啶基）-4-异恶唑基]丙酸[[（S）-2-Py-AMPA，5]和（RS）-2-氨基-3- [3-羟基-5-（2-噻唑基）-4-异恶唑基]丙酸（4）是有效的AMPA激动剂。另一方面，（R）-APPA（3）和（R）-2-Py-AMPA（6）被证明是弱AMPA拮抗剂。现在，我们报告了2-Py-AMPA（7a）和异构体化合物3-Py-AMPA（7b）和4-Py-AMPA（7c）以及7a类似物（RS）-2-amino-的合成3- [3-羟基-5-（6-甲基-2-吡啶基）-4-异恶唑基]丙酸（7d）和（RS）-2-氨基-3-

  DOI：

  10.1021/jm9801206
• 作为产物：
  描述：

  6-甲基-2-吡啶基甲醇 、 甲氧羰基亚甲基三苯基正膦 在 C₃₄H₃₇N₄O₆Ru₂⁽¹⁺⁾*Cl^(1-) 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以82%的产率得到(E)-methyl 3-(6-methylpyridin-2-yl)acrylate
  参考文献：
  名称：

  Acceptorless Dehydrogenation of Alcohols on a Diruthenium(II,II) Platform

  摘要：

  The diruthenium(II,II) complex [Ru-2(L-1)(OAc)(3)]Cl (1), spanned by a naphthyridine-diimine ligand and bridged by three acetates, has been synthesized. The catalytic efficacy of complex 1 has been evaluated for the acceptorless dehydrogenation (AD) of alcohols and for the dehydrogenative coupling reactions of alcohols with Wittig reagents. The diruthenium(II,II) complex is an excellent catalyst for AD of a diverse range of alcohols, and it is shown to be particularly effective for the conversion of primary alcohols to the corresponding aldehydes without undesired side products such as esters. Triphenylphosphonium ylides in a one-pot reaction with alcohols afforded the corresponding olefins in high yields with excellent E selectivity. The liberated dihydrogen gas was identified and measured to be 1 equiv with respect to alcohol. Deuteration studies with PhCD2OH revealed the absence of isotope scrambling in the product, indicating the involvement of a Ru-monohydride intermediate. Kinetic studies and DFT calculations suggest a low-energy bimetallic beta-hydride elimination pathway where rate-limiting intramolecular proton transfer from alcohol to metal-bound hydride constitutes the dehydrogenation step. The general utility of metal-metal bonded compounds for alcohol AD and subsequent coupling reactions is demonstrated here.

  DOI：

  10.1021/acs.organomet.6b00085

文献信息

• Efficient and fast Heck vinylation of 2-bromo-6-methyl pyridines with methylacrylate. Application to the synthesis of 6-methyl cyclopenta[b]pyridinone
  作者：Nicolas Robert、Christophe Hoarau、Sylvain Célanire、Pierre Ribéreau、Alain Godard、Guy Quéguiner、Francis Marsais

  DOI：10.1016/j.tet.2005.03.008

  日期：2005.5

  Heck vinylation of 2-bromo-6-methyl-3-substituted pyridines using eta(3)-allylpalladium chloride dimer/P(o-Tol)(3) complex/toluene and dimethylacetamide (DMA) as co-solvent with methyl acrylate is reported. Electronic and steric effects were investigated engaging diversely 2-bromo-3,6-disubstituted pyridines. As application, a new synthesis of the 6-methyl cyclopenta[b]pyridinone building-block connecting Heck vinylation, alkene reduction and Dieckmann condensation is described. (c) 2005 Published by Elsevier Ltd.