(E)-ethyl 4-(trimethylsilyl)-3-butenoate | 147583-39-9

• 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: (E)-ethyl 4-(trimethylsilyl)-3-butenoate
• 英文别名: 4-trimethylsilyl-3(E)-butenoate；ethyl (E)-4-trimethylsilylbut-3-enoate
• CAS: 147583-39-9
• 化学式: C₉H₁₈O₂Si
• 分子量: 186.326
• InChiKey: LZCWCLOPTPHHAO-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-(trimethylsilyl)-3-butenoate 以75%的产率得到
  参考文献：
  名称：

  Miyazaki Yasushi, Hotta Hiroyasu, Sato Fumie, Tetrahedron Lett, 35 (1994) N 25, S 4389- 4392

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(trimethylsilyl)-2-propenylacetate 以71%的产率得到
  参考文献：
  名称：

  Miyazaki Yasushi, Hotta Hiroyasu, Sato Fumie, Tetrahedron Lett, 35 (1994) N 25, S 4389- 4392

  摘要：

  DOI：

文献信息

• Palladium(0)-catalyzed alkoxycarbonylation of allyl phosphates and acetates
  作者：Shunichi Murahashi、Yasushi Imada、Yuki Taniguchi、Shinya Higashiura

  DOI：10.1021/jo00058a040

  日期：1993.3

  Palladium-catalyzed alkoxycarbonylation of allyl phosphates under CO (1 atm) at 50-degrees-C proceeds highly efficiently to give the corresponding beta,gamma-unsaturated esters. The carbonylation of geranyl phosphate ((E)-11) under CO (1 atm) at 50-degrees-C gave ethyl ester of homogeranic acid ((E)-12) stereoselectively. The carbonylation takes place at the least substituted allylic positions with inversion of configuration. Typically, the methoxycarbonylation of cis-5-(methoxycarbonyl)-2-cyclohexen-1-yl phosphate (cis-16) gave trans-dimethyl 2-cyclohexene-1,5-dicarboxylate (trans-17) selectively. Alkoxycarbonylation of allyl acetates is performed for the first time in the presence of a catalytic amount of bromide ion. The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium(0) species to allyl acetates to give pi-allylpalladium acetate, fast ligand exchange of the acetate with bromide, insertion of carbon monoxide to give acylpalladium species, and alkoxylation.
• Synthesis of β-hydroxy-γ-trimethylsilyl-γ-butyrolactone as key chiral building block for preparation of four-carbon chain units having tertiary stereogenic carbon
  作者：Yasushi Miyazaki、Hiroyasu Hotta、Fumie Sato

  DOI：10.1016/s0040-4039(00)73364-8

  日期：1994.6

  A new chiral building block beta-hydroxy-gamma-trimethylsilyl-gamma-butyrolactone (1) was prepared from gamma-trimethylsilylallyl acetate (2) via two steps in excellent overall yield. The lactone 1 is useful precursor to four-carbon chain blocks having tertiary stereogenic center such as 6, 10 and 11.
• Murahashi Shun-Ichi, Imada Yasushi, Taniguchi Yuki, Higashiura Shinya, J. Org. Chem, 58 (1993) N 6, S 1538-1545
  作者：Murahashi Shun-Ichi, Imada Yasushi, Taniguchi Yuki, Higashiura Shinya

  DOI：——

  日期：——
• Miyazaki Yasushi, Hotta Hiroyasu, Sato Fumie, Tetrahedron Lett, 35 (1994) N 25, S 4389- 4392
  作者：Miyazaki Yasushi, Hotta Hiroyasu, Sato Fumie

  DOI：——

  日期：——