methyl (Z)-2-ethylidene-3-((Z)-2-((triethylsilyl)oxy)vinyl)hexanoate | 1035485-23-4

• 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: methyl (Z)-2-ethylidene-3-((Z)-2-((triethylsilyl)oxy)vinyl)hexanoate
• CAS: 1035485-23-4
• 化学式: C₁₇H₃₂O₃Si
• 分子量: 312.525
• InChiKey: HAQRIBUBAXGGPY-FQSMVDRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  21.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 2-已烯醛 、 2-丁炔酸甲酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 三环己基膦 作用下， 以 四氢呋喃 为溶剂， 生成 methyl (Z)-2-ethylidene-3-((Z)-2-((triethylsilyl)oxy)vinyl)hexanoate 、 (E)-methyl 3-methyl-4-((Z)-2-(triethylsilyloxy)vinyl)hept-2-enoate
  参考文献：
  名称：

  Evolution of Efficient Strategies for Enone−Alkyne and Enal−Alkyne Reductive Couplings

  摘要：

  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.

  DOI：

  10.1021/ja9083607

文献信息

• Highly Chemoselective and Stereoselective Synthesis of <i>Z</i>-Enol Silanes
  作者：Ananda Herath、John Montgomery

  DOI：10.1021/ja802844v

  日期：2008.7.1

  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.