pentanoic acid 3-cis-hexenyl ester

• 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: pentanoic acid 3-cis-hexenyl ester
• 英文别名: [(Z)-hex-1-enyl] pentanoate
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: QVSWHXAMEIASBU-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  1-己炔 、 正戊酸 在 Ru(η³-CH2=C(Me)CH2)2 作用下， 以 正戊烷 为溶剂， 反应 22.0h， 生成 pentanoic acid 3-cis-hexenyl ester 、 (E)-Hex-1-en-1-yl valerate
  参考文献：
  名称：

  General Synthesis of (Z)-Alk-1-en-1-yl Esters via Ruthenium-Catalyzed anti-Markovnikov trans-Addition of Carboxylic Acids to Terminal Alkynes

  摘要：

  The direct addition of carboxylic acids to terminal alkynes in the presence of catalytic amounts of (bis(diphenylphosphino)alkane)Ru(eta(3)-methallyl)(2) complexes provides a novel selective route to (Z)-alk-1-en-1-yl esters. This reaction involves an anti-Markovnikov and trans-addition to alkynes and gives access to a variety of new (Z)-alkene derivatives from hex-1-yne, phenylacetylene, and (trimethylsilyl)acetylene. The actual catalyst precursors are (bis(diphenylphosphino)alkane)Ru(eta(2)-carboxylate)(2) complexes formed in situ during the reaction.

  DOI：

  10.1021/jo00127a033

文献信息

• Thermal Decomposition of Pentacarbonyl(1-acyloxyalkylidene)chromium(0) Complexes:  Formation of <i>Z</i>-Enol Esters
  作者：Björn C. Söderberg、Jian Liu、Thomas W. Ball、Michael J. Turbeville

  DOI：10.1021/jo962197c

  日期：1997.8.1

  Pentacarbonyl(1-acyloxyalkylidene)chromium(0) complexes, formed in situ by reaction of the corresponding tetramethylammonium pentacarbonyl(1-oxoalkyl)chromate(1-) salts with carboxylic acid halides, affords enol esters in moderate to good yields. In all cases examined, the Z-enol ester was obtained as the major or exclusive isomer. Addition of I equiv of pyridine to the reaction mixture substantially improved the Z/E ratio and, in most cases, increased the chemical yield.
• General Synthesis of (Z)-Alk-1-en-1-yl Esters via Ruthenium-Catalyzed anti-Markovnikov trans-Addition of Carboxylic Acids to Terminal Alkynes
  作者：Henri Doucet、Blanca Martin-Vaca、Christian Bruneau、Pierre H. Dixneuf

  DOI：10.1021/jo00127a033

  日期：1995.11

  The direct addition of carboxylic acids to terminal alkynes in the presence of catalytic amounts of (bis(diphenylphosphino)alkane)Ru(eta(3)-methallyl)(2) complexes provides a novel selective route to (Z)-alk-1-en-1-yl esters. This reaction involves an anti-Markovnikov and trans-addition to alkynes and gives access to a variety of new (Z)-alkene derivatives from hex-1-yne, phenylacetylene, and (trimethylsilyl)acetylene. The actual catalyst precursors are (bis(diphenylphosphino)alkane)Ru(eta(2)-carboxylate)(2) complexes formed in situ during the reaction.