Tert-butyl 2-[phenyl(triethylsilyloxy)methyl]prop-2-enoate | 1399773-88-6

• 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: Tert-butyl 2-[phenyl(triethylsilyloxy)methyl]prop-2-enoate
• 英文别名: tert-butyl 2-[phenyl(triethylsilyloxy)methyl]prop-2-enoate
• CAS: 1399773-88-6
• 化学式: C₂₀H₃₂O₃Si
• 分子量: 348.558
• InChiKey: INJJRTZZTXMZFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 叔丁基丙炔酸酯 、 苯甲醛 在 bis(1,5-cyclooctadiene)nickel (0) 、 C₂₇H₃₈N₂*BF₄H 、 potassium tert-butylate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 9.08h， 以46%的产率得到tert-butyl 4-phenyl-4-triethylsilyloxybut-2-enoate
  参考文献：
  名称：

  Quick Installation of a 1,4-Difunctionality via Regioselective Nickel-Catalyzed Reductive Coupling of Ynoates and Aldehydes

  摘要：

  The development of efficient methods for the synthesis of molecules with 1,4-difunctionalities has been a dire need of the synthetic community. In this work, intermolecular reductive coupling of ynoates and aldehydes (in the presence of a silane) has been accomplished for the first time using catalytic amounts of Ni(COD)(2), an N-heterocyclic carbene ligand, and PPh3. High regioselectivity has been demonstrated for the multicomponent coupling reactions, and more than a dozen invaluable silyl-protected gamma-hydrox-alpha,beta-enoates have been synthesized. This methodology provides a quick entry to many other 1,4-difunctional compounds and oxygen-containing five-membered rings. The intermediacy of metallacycles in the catalytic process has been established by deuterium-labeling experiments.

  DOI：

  10.1021/jo301790q

文献信息

• Quick Installation of a 1,4-Difunctionality via Regioselective Nickel-Catalyzed Reductive Coupling of Ynoates and Aldehydes
  作者：Sanjeewa K. Rodrigo、Hairong Guan

  DOI：10.1021/jo301790q

  日期：2012.9.21

  The development of efficient methods for the synthesis of molecules with 1,4-difunctionalities has been a dire need of the synthetic community. In this work, intermolecular reductive coupling of ynoates and aldehydes (in the presence of a silane) has been accomplished for the first time using catalytic amounts of Ni(COD)(2), an N-heterocyclic carbene ligand, and PPh3. High regioselectivity has been demonstrated for the multicomponent coupling reactions, and more than a dozen invaluable silyl-protected gamma-hydrox-alpha,beta-enoates have been synthesized. This methodology provides a quick entry to many other 1,4-difunctional compounds and oxygen-containing five-membered rings. The intermediacy of metallacycles in the catalytic process has been established by deuterium-labeling experiments.