(Z)-3-benzylidene-4-((Z)-2-(triethylsilyloxy)vinyl)heptan-2-ol | 1035485-17-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (Z)-3-benzylidene-4-((Z)-2-(triethylsilyloxy)vinyl)heptan-2-ol
• 英文别名: (Z)-benzylidene-4-((Z)-2-(triethylsilyloxy)vinyl)heptan-2-ol
• CAS: 1035485-17-6
• 化学式: C₂₂H₃₆O₂Si
• 分子量: 360.612
• InChiKey: RDNWEFLOWHJIGH-JLAYCCIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 2-已烯醛 、 4-苯基-3-丁炔-2-醇 在 bis(1,5-cyclooctadiene)nickel (0) 、 三环己基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到(Z)-3-benzylidene-4-((Z)-2-(triethylsilyloxy)vinyl)heptan-2-ol
  参考文献：
  名称：

  Highly Chemoselective and Stereoselective Synthesis of Z-Enol Silanes

  摘要：

  Three-component nickel-catalyzed couplings of enals, alkynes, and silanes have been developed as a new entry to enol silanes. The enol silane and a trisubstituted alkene are both formed with > 98:2 stereoselectively, and the reaction tolerates a broad range of functionality including aldehydes, ketones, esters, free hydroxyls, and basic secondary amines. A mechanistic pathway involving the formation of a metallacycle that possesses and eta(1) nickel O-enolate motif explains the high level of stereoselection.

  DOI：

  10.1021/ja802844v

文献信息

• Evolution of Efficient Strategies for Enone−Alkyne and Enal−Alkyne Reductive Couplings
  作者：Wei Li、Ananda Herath、John Montgomery

  DOI：10.1021/ja9083607

  日期：2009.11.25

  Strategies for the reductive coupling of enones or enals with alkynes have been developed. The reducing agents employed include organozincs, organoboranes, organosilanes, and methanol. The latter of these strategies is simple, cost-effective, and tolerant of many functional groups. Isotopic labeling strategies have provided supporting evidence for the mechanistic proposals.