(Z)-3'-Phenyl-2'-propenyl 2-butynoate | 146099-14-1

• 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)-3'-Phenyl-2'-propenyl 2-butynoate
• 英文别名: 3'-phenyl-2'(Z)-propenyl 2-butynoate；[(Z)-3-phenylprop-2-enyl] but-2-ynoate
• CAS: 146099-14-1
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: DRTIBMODDBUJRB-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  (Z)-3'-Phenyl-2'-propenyl 2-butynoate 以100%的产率得到
  参考文献：
  名称：

  Ma Shengming, Lu Xiyan, J. Org. Chem., 58 (1993) N 5, S 1245-1250

  摘要：

  DOI：
• 作为产物：
  描述：

  2-丁炔酸 、 (Z)-肉桂醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以97%的产率得到(Z)-3'-Phenyl-2'-propenyl 2-butynoate
  参考文献：
  名称：

  Stereoselective synthesis of .alpha.-chloromethylene-.gamma.-butyrolactone derivatives from acyclic allylic 2-alkynoates

  摘要：

  Alpha-Methylene-gamma-butyrolactones have been constructed by a bis(benzonitrile)palladium dichloride catalyzed cyclization reaction of the easily available acyclic 2'-alkenyl 2-alkynoates in the presence of CuCl2. A mechanism involving a stereoselective chloropalladation in the presence of CuCl2, followed by intramolecular insertion of a carbon-carbon double bond to the carbon-palladium bond, and subsequent CuCl2-mediated formation of a new carbon-chlorine bond is briefly discussed.

  DOI：

  10.1021/jo00057a043

文献信息

• Molecular oxygen promoted oxidative cleavage of carbon-palladium bonds — catalytic cyclization of allylic 2-alkynoates to α-alkylidine-γ-butyrolactones by a PdII complex
  作者：Guoxin Zhu、Xiyan Lu

  DOI：10.1016/0022-328x(95)05781-j

  日期：1996.2

  Molecular oxygen was used as the oxidant to promote the PdII and CuII catalyzed cyclization of acyclic allylic 2-alkynoates, yielding α-haloakylidene-gg-butyrokactones with high stereoselectivity. The stereochemitsyr of halopalladation of the carbon-carbon triple bond, 1,2-induction in the intramolecular carbon-carbon double insertion and oxidative cleavage of carbon-palladium bonds in the cyclization

  分子氧用作氧化剂，以促进Pd II和Cu II催化无环烯丙基2-链烷酸酯的环化反应，产生具有高立体选择性的α-卤代亚烷基-gg-丁酮内酯。详细研究了碳-碳三键的卤代缩合的立体化学，分子内碳-碳双插入的1,2-诱导和环化反应中碳-钯键的氧化裂解。
• Palladium‐Catalyzed Oxidative Cyclization of Enynes with Hydrogen Peroxide as the Oxidant
  作者：Guoyin Yin、Guosheng Liu

  DOI：10.1002/anie.200801438

  日期：2008.7.7
• Palladium-Templated Regio- and Stereoselective Cyclization of 2'-Alkenyl 2-Alkynoates and Its Synthetic Applications
  作者：Jianguo Ji、Chunming Zhang、Xiyan Lu

  DOI：10.1021/jo00110a018

  日期：1995.3

  2'-Alkenyl 2-alkynoates undergo facile stereoselective cyclization to alpha-(haloalkylidene)-gamma-butyrolactones upon treatment with a catalytic amount of palladium complex in the presence of CuX(2) and LiX. When an alkyl group is introduced to the 1'-position of the alkenyl group, unsubstituted 2-propynoates mainly give trans-beta, gamma-disubstituted gamma-lactones, and substituted 2-propynoates afford cis-beta,gamma-disubstituted gamma-lactones. Further elaborations of the halogen atoms and the synthesis of A-factor using this method are exemplified.
• Ma Shengming, Lu Xiyan, J. Org. Chem., 58 (1993) N 5, S 1245-1250
  作者：Ma Shengming, Lu Xiyan

  DOI：——

  日期：——
• Stereoselective synthesis of .alpha.-chloromethylene-.gamma.-butyrolactone derivatives from acyclic allylic 2-alkynoates
  作者：Shengming Ma、Xiyan Lu

  DOI：10.1021/jo00057a043

  日期：1993.2

  Alpha-Methylene-gamma-butyrolactones have been constructed by a bis(benzonitrile)palladium dichloride catalyzed cyclization reaction of the easily available acyclic 2'-alkenyl 2-alkynoates in the presence of CuCl2. A mechanism involving a stereoselective chloropalladation in the presence of CuCl2, followed by intramolecular insertion of a carbon-carbon double bond to the carbon-palladium bond, and subsequent CuCl2-mediated formation of a new carbon-chlorine bond is briefly discussed.