ethyl 3-methyl-2-[(trimethylsilyl)ethynyl]undec-2-enoate | 1038863-34-1

• 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: ethyl 3-methyl-2-[(trimethylsilyl)ethynyl]undec-2-enoate
• 英文别名: ethyl (Z)-3-methyl-2-(2-trimethylsilylethynyl)undec-2-enoate
• CAS: 1038863-34-1
• 化学式: C₁₉H₃₄O₂Si
• 分子量: 322.563
• InChiKey: PUTHPRMUPLEKCE-ZCXUNETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-ethyl 3-chloro-2-(2-(trimethylsilyl)ethynyl)but-2-enoate 、 9-octyl-9-bora-bicyclo[3.3.1]nonane 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium phosphate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 以64%的产率得到ethyl 3-methyl-2-[(trimethylsilyl)ethynyl]undec-2-enoate
  参考文献：
  名称：

  A simple method to prepare single isomer tetrasubstituted olefins by successive Suzuki–Miyaura cross-couplings of E-β-chloro-α-iodo-α,β-unsaturated esters

  摘要：

  A convenient method of synthesizing tetrasubstituted olefins as single isomers is described. E-beta-Chloro-alpha-iodo-alpha,beta-unsaturatecl esters are first converted into the corresponding E-beta-chloro-alpha,beta-unsaturatedesters using Suzuki-Miyaura coupling reactions with arylboronic acids and alkenylboronic acids. These transformations gave complete selectivity, and proceeded with substitution at the more activated alpha-iodide position. These compounds, isolated as single isomers, were then transformed into tetrasubstituted olefins by Suzuki-Miyaura couplings with arylboronic acids, alkenylboronic acids, and alkyl boranes to afford the corresponding tetrasubstituted olefins as single isomers. During this coupling process, it was discovered that the use of small ligands, such as PMe3 or PEt3, was critical for efficient coupling. The stereochemistry and regiochemistry of the products were unequivocally established using NMR methods. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.004

文献信息

• A simple method to prepare single isomer tetrasubstituted olefins by successive Suzuki–Miyaura cross-couplings of E-β-chloro-α-iodo-α,β-unsaturated esters
  作者：Julie Simard-Mercier、Alison B. Flynn、William W. Ogilvie

  DOI：10.1016/j.tet.2008.04.004

  日期：2008.6

  A convenient method of synthesizing tetrasubstituted olefins as single isomers is described. E-beta-Chloro-alpha-iodo-alpha,beta-unsaturatecl esters are first converted into the corresponding E-beta-chloro-alpha,beta-unsaturatedesters using Suzuki-Miyaura coupling reactions with arylboronic acids and alkenylboronic acids. These transformations gave complete selectivity, and proceeded with substitution at the more activated alpha-iodide position. These compounds, isolated as single isomers, were then transformed into tetrasubstituted olefins by Suzuki-Miyaura couplings with arylboronic acids, alkenylboronic acids, and alkyl boranes to afford the corresponding tetrasubstituted olefins as single isomers. During this coupling process, it was discovered that the use of small ligands, such as PMe3 or PEt3, was critical for efficient coupling. The stereochemistry and regiochemistry of the products were unequivocally established using NMR methods. (C) 2008 Elsevier Ltd. All rights reserved.