(Z)-β-Styryl crotonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-β-Styryl crotonate
• 英文别名: [(Z)-2-phenylethenyl] (E)-but-2-enoate
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: MYBYLSLXGXEOBB-LOABUPAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  巴豆酸 、 苯乙炔 在 Ru(η³-CH2=C(Me)CH2)2 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以85%的产率得到(Z)-β-Styryl crotonate
  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

• Synthesis and structure of some ruthenium–rhenium heterodinuclear complexes and their catalytic activity in the addition of carboxylic acids to phenylacetylene
  作者：Suming Ye、Weng Kee Leong

  DOI：10.1016/j.jorganchem.2005.11.061

  日期：2006.3

  Cp*(CO)Ru(μ-H)[μ-PhP(C6H4)CH2PPh2]Re(CO)3, was also obtained from the first reaction. All these heterodinuclear products have been characterised crystallographically. They also showed good catalytic activity for the addition of carboxylic acids to phenylacetylene to afford the anti-Markovnikov products selectively.

  Na [Re（CO）5 ]与Cp * Ru（dppm）Cl，CpRu（dppm）Cl或CpRu（CO）2 Cl的盐消除反应得到异核物质Cp * Ru（μ-CO）2（μ- dppm）Re（CO）3，Cp（CO）Ru（μ-dppm）Re（CO）4或Cp（CO）2 RuRe（CO）5的产率中等。正金属化物种Cp *（CO）Ru（μ-H）[μ-PhP（C 6 H 4）CH 2 PPh 2 ] Re（CO）3也从第一反应获得。所有这些异双核产物均已通过晶体学表征。他们还显示出良好的催化活性，可以将羧酸加到苯乙炔中，从而选择性地提供抗马尔科夫尼科夫产物。
• Regio- and stereoselective addition of carboxylic acids to phenylacetylene catalyzed by cyclopentadienyl ruthenium complexes
  作者：Suming Ye、Weng Kee Leong

  DOI：10.1016/j.jorganchem.2005.11.023

  日期：2006.3

  The direct addition of carboxylic acids to terminal alkynes Such as phenylacetylene in the presence of catalytic amount of [CpRu(CO)(2)CI] (1) or [CpRu(CO)(2)}(2)] (2) affords the anti-Markovnikov adducts with high selectivity. In most instances, the E-enol esters are the major products. (c) 2005 Elsevier B.V. All rights reserved.
• 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.