(E)-methyl 3-phenyl-2-((N-phenylacetamido)methyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl 3-phenyl-2-((N-phenylacetamido)methyl)acrylate
• 英文别名: methyl (E)-2-[(N-acetylanilino)methyl]-3-phenylprop-2-enoate
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: OPFVIZFHHCOROS-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-phenyl-2-((N-phenylacetamido)methyl)acrylate 、 4-氯苯硼酸 在 potassium fluoride 、 palladium diacetate 、 丙酸 作用下， 反应 2.0h， 以85%的产率得到(E)-methyl 3-(4-chlorophenyl)-3-phenyl-2-[(N-phenylacetamido)methyl]acrylate
  参考文献：
  名称：

  以2,2,6,6-四甲基哌啶-N-氧基（TEMPO）为氧化剂的烯丙基胺的氧化Heck偶联制备四取代的烯烃

  摘要：

  AbstractThe paper describes the oxidative Heck arylation of various allylic amines using arylboronic acids for the preparation of tetrasubstituted alkenes. As oxidant the commercially available 2,2,6,6‐tetramethylpiperidine‐N‐oxyl (TEMPO) is used and coupling reactions occur under very mild conditions at room temperature. The densely substituted alkenes are formed in good to excellent yields with complete control of the diastereoselectivity. Substrate scope with respect to the allylic amine and the arylboronic acid is investigated.magnified image

  DOI：

  10.1002/adsc.201300846
• 作为产物：
  描述：

  (Z)-methyl 2-(bromomethyl)-3-phenylacrylate 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (E)-methyl 3-phenyl-2-((N-phenylacetamido)methyl)acrylate
  参考文献：
  名称：

  以2,2,6,6-四甲基哌啶-N-氧基（TEMPO）为氧化剂的烯丙基胺的氧化Heck偶联制备四取代的烯烃

  摘要：

  AbstractThe paper describes the oxidative Heck arylation of various allylic amines using arylboronic acids for the preparation of tetrasubstituted alkenes. As oxidant the commercially available 2,2,6,6‐tetramethylpiperidine‐N‐oxyl (TEMPO) is used and coupling reactions occur under very mild conditions at room temperature. The densely substituted alkenes are formed in good to excellent yields with complete control of the diastereoselectivity. Substrate scope with respect to the allylic amine and the arylboronic acid is investigated.magnified image

  DOI：

  10.1002/adsc.201300846

文献信息

• Palladium‐Catalyzed, Chelation‐Assisted Stereo‐ and Regioselective Synthesis of Tetrasubstituted Olefins by Oxidative Heck Arylation
  作者：Hyun Seung Lee、Ko Hoon Kim、Sung Hwan Kim、Jae Nyoung Kim

  DOI：10.1002/adsc.201200306

  日期：2012.9.17

  An efficient synthesis of tetrasubstituted olefins was achieved via a palladium‐catalyzed, chelation‐assisted oxidative Heck arylation protocol from trisubstituted olefins bearing a tether with a directing group in a completely stereo‐ and regioselective manner. The stereo‐ and regioselectivity as well as excellent yields of tetrasubstituted olefins originated from the stabilization of a palladium

  通过钯催化的，螯合辅助的氧化Heck芳基化反应方案，可以从带有取代基的带有方向基团的三取代烯烃以完全立体和区域选择性的方式高效合成四取代烯烃。四取代烯烃的立体选择性和区域选择性以及出色的收率均源于钯中间物与导向基团之间的螯合作用，使钯中间体稳定。
• Oxidative Heck Coupling of Allylic Amines with 2,2,6,6‐Tetramethylpiperidine‐ <i>N</i> ‐oxyl (TEMPO) as Oxidant for the Preparation of Tetrasubstituted Alkenes
  作者：Zhiheng He、Birgit Wibbeling、Armido Studer

  DOI：10.1002/adsc.201300846

  日期：2013.12.16

  AbstractThe paper describes the oxidative Heck arylation of various allylic amines using arylboronic acids for the preparation of tetrasubstituted alkenes. As oxidant the commercially available 2,2,6,6‐tetramethylpiperidine‐N‐oxyl (TEMPO) is used and coupling reactions occur under very mild conditions at room temperature. The densely substituted alkenes are formed in good to excellent yields with complete control of the diastereoselectivity. Substrate scope with respect to the allylic amine and the arylboronic acid is investigated.magnified image