(Z)-β-Styryl salicylate

• 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 salicylate
• 英文别名: (Z)-styryl 2-hydroxybenzoate；(Z)-2-phenylethenyl salicylate；[(Z)-2-phenylethenyl] 2-hydroxybenzoate
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: UPDCVVSQIAMBNJ-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙炔 、 水杨酸 在 Ru(η³-CH2=C(Me)CH2)2 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以94%的产率得到(Z)-β-Styryl salicylate
  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 [Ru(dppe)2(CH3CN)Cl][BPh4] and its catalytic application to anti-Markovnikov addition of carboxylic acids to terminal alkynes
  作者：Uttam Kumar Das、Manish Bhattacharjee

  DOI：10.1016/j.jorganchem.2011.11.017

  日期：2012.3

  from the precursor complex, [(PPh3)2Ru(CH3CN)3Cl][BPh4]. The complex has been structurally characterized. This complex has been found to be an efficient catalyst for the anti-Markovnikov addition of carboxylic acids to alkynes.

  [Ru（dppe）2（CH 3 CN）Cl] [BPh 4 ]（1）是由前体络合物[（PPh 3）2 Ru（CH 3 CN）3 Cl] [BPh 4 ]合成的。。该复合物已在结构上进行了表征。已经发现该络合物是将羧酸抗马尔科夫尼科夫加成至炔烃的有效催化剂。
• 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.