2-丙烯酸,3-(3-甲酰基-2-萘基)-,甲基酯,(E)- | 139527-81-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 中文名称: 2-丙烯酸,3-(3-甲酰基-2-萘基)-,甲基酯,(E)-
• 英文名称: 2-formyl-3-(2'-carbomethoxyethenyl)naphthalene
• 英文别名: (E)-methyl 3-(2-formylnaphthalen-3-yl)acrylate；methyl (E)-3-(3-formylnaphthalen-2-yl)prop-2-enoate
• CAS: 139527-81-4
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: OPVUWMCHPJUXLL-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-3-(3-Dimethoxymethyl-naphthalen-2-yl)-acrylic acid methyl ester 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-丙烯酸,3-(3-甲酰基-2-萘基)-,甲基酯,(E)-
  参考文献：
  名称：

  An unusual doubly substituted product from the phase-transfer-catalyzed Heck reactions of o-bromobenzaldehydes with methyl acrylate

  摘要：

  The reactions of o-bromobenzaldehydes with methyl acrylate under Heck conditions and with phase-transfer catalysis to yield significant amounts of doubly substituted deformylated products 1A-E in addition to the expected o-formyl cinnamates 2A-E are reported. X-ray crystallography of one such product (4) established that the bromine was replaced by a propionate and the formyl group by an acrylate residue. Employment of deuterium-labeled substrates showed that the hydrogen atom of the formyl group of the substrate was transferred intramolecularly and regiospecifically to the benzylic carbon of the propionate substituent of the product. A tentative hypothesis is advanced to explain these and other experimental findings.

  DOI：

  10.1021/jo00034a041

文献信息

• Highly Regio- and Stereoselective Ruthenium(II)-Catalyzed Direct <i>ortho</i>-Alkenylation of Aromatic and Heteroaromatic Aldehydes with Activated Alkenes under Open Atmosphere
  作者：Kishor Padala、Masilamani Jeganmohan

  DOI：10.1021/ol3000684

  日期：2012.2.17

  reacted with activated alkenes in the presence of a catalytic amount of [RuCl2(p-cymene)}2], AgSbF6, and Cu(OAc)2·H2O to give substituted alkene derivatives in a highly regio- and stereoselective manner. The corresponding alkene derivatives were further converted into unusual four-membered cyclic ketones or a polycyclic isochromanone derivative via a photochemical rearrangement. Notably, the catalytic

  在催化量的[RuCl 2（p- cymene）} 2 ]，AgSbF 6和Cu（OAc）2 ·H 2 O的存在下，各种芳族和杂芳族醛与活化的烯烃反应，得到取代的烯烃衍生物。高度区域选择性和立体选择性的方式。相应的烯烃衍生物通过光化学重排进一步转化为不寻常的四元环酮或多环异苯并二氢吡喃酮衍生物。值得注意的是，催化反应是在开放气氛下进行的。