(E)-methyl 3-(3-nitrophenyl)-3-phenylacrylate | 1198097-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-methyl 3-(3-nitrophenyl)-3-phenylacrylate
• 英文别名: methyl (E)-3-(3-nitrophenyl)-3-phenylprop-2-enoate
• CAS: 1198097-86-7
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: USSUFHKCAXAITK-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-nitrobenzene-1-diazonium tertafluoroborate 、 肉桂酸甲酯 在 palladium diacetate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (E)-methyl 3-(3-nitrophenyl)-3-phenylacrylate
  参考文献：
  名称：

  肉桂酸甲酯与亚砷二唑鎓盐的Heck反应的非对映选择性的显着电子效应：（±）-茚达林和（±）-Sertraline的正式全合成

  摘要：

  Abstractmagnified imageAn efficient and stereoselective protocol for the preparation of β,β‐disubstituted acrylates in good to high yields by means of a Heck–Matsuda arylation was accomplished. The method employs a base‐ and ligand‐free Heck arylation reaction of methyl cinnamate using both electron‐deficient and electron‐rich arenediazonium salts as electrophiles. The Heck reaction displays a remarkable electronic dependence regarding the diastereoselectivity of the arylation process, which correlates with the electronic nature of the arenediazonium salts employed. A rationale for the observed diastereoselectivity is presented. The overall methodology provides a convenient route to 3‐arylindanones and 4‐aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (±)‐indatraline and (±)‐sertraline.

  DOI：

  10.1002/adsc.200900032

文献信息

• Remarkable Electronic Effect on the Diastereoselectivity of the Heck Reaction of Methyl Cinnamate with Arenediazonium Salts: Formal Total Synthesis of (±)-Indatraline and (±)-Sertraline
  作者：Julio Cezar Pastre、Carlos Roque Duarte Correia

  DOI：10.1002/adsc.200900032

  日期：2009.6

  Abstractmagnified imageAn efficient and stereoselective protocol for the preparation of β,β‐disubstituted acrylates in good to high yields by means of a Heck–Matsuda arylation was accomplished. The method employs a base‐ and ligand‐free Heck arylation reaction of methyl cinnamate using both electron‐deficient and electron‐rich arenediazonium salts as electrophiles. The Heck reaction displays a remarkable electronic dependence regarding the diastereoselectivity of the arylation process, which correlates with the electronic nature of the arenediazonium salts employed. A rationale for the observed diastereoselectivity is presented. The overall methodology provides a convenient route to 3‐arylindanones and 4‐aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (±)‐indatraline and (±)‐sertraline.