(3-vinylcyclopent-3-ene-1,1-diyl)dimethanol | 874919-05-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-vinylcyclopent-3-ene-1,1-diyl)dimethanol
• 英文别名: [3-Ethenyl-1-(hydroxymethyl)cyclopent-3-en-1-yl]methanol
• CAS: 874919-05-8
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: RFCUBXZVDFWETL-UHFFFAOYSA-N

物化性质

• 沸点：
  238.5±25.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-vinylcyclopent-3-ene-1,1-diyl)dimethanol 在 [2-(benzyloxy)phenyl]diphenylphosphane 、 bi(allylnickel bromide) 、 Na{[1,3-(CF₃)2C₆H₃]4B} 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 15.5h， 生成 4,4-[bis(benzyloxy)methyl]-1-(1-methylprop-2-enyl)cyclopentene
  参考文献：
  名称：

  Hydrovinylation of 1,3-Dienes:  A New Protocol, an Asymmetric Variation, and a Potential Solution to the Exocyclic Side Chain Stereochemistry Problem

  摘要：

  Cyclic and acyclic 1,3-dienes undergo efficient (substrate/catalyst = 72) heterodimerization with ethylene in the presence of a Ni catalyst prepared from [o-(PhCH2O)]C6H4PPh2, [(allyl)2NiBr]2, and Na+ BAr4- (Ar = 3,5-bis-trifluromethylphenyl), giving 1,2-addition products. Yields up to 99% can be realized for several 1-vinylcycloalkenes and 1-substituted 1,3-butadienes. Phospholanes with suitably placed hemilabile ligating groups and phosphoramidites derived from binaphthol are excellent ligands for an asymmetric variation of this reaction, the latter giving 99% yield and >95% ee's for selected substrates. An example of how an exocyclic chiral center can be used to install other stereo-centers in the ring (e. g., the carbon to which the side chain is attached) is also provided. These discoveries open an expeditious entry into several biologically relevant classes of compounds, especially those carrying tetrahydronaphthalene and related heterocyclic moieties.

  DOI：

  10.1021/ja0561338
• 作为产物：
  描述：

  1,1-diethyl 3-ethenylcyclopent-3-ene-1,1-dicarboxylate 在 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 反应 13.5h， 以77%的产率得到(3-vinylcyclopent-3-ene-1,1-diyl)dimethanol
  参考文献：
  名称：

  Hydrovinylation of 1,3-Dienes:  A New Protocol, an Asymmetric Variation, and a Potential Solution to the Exocyclic Side Chain Stereochemistry Problem

  摘要：

  Cyclic and acyclic 1,3-dienes undergo efficient (substrate/catalyst = 72) heterodimerization with ethylene in the presence of a Ni catalyst prepared from [o-(PhCH2O)]C6H4PPh2, [(allyl)2NiBr]2, and Na+ BAr4- (Ar = 3,5-bis-trifluromethylphenyl), giving 1,2-addition products. Yields up to 99% can be realized for several 1-vinylcycloalkenes and 1-substituted 1,3-butadienes. Phospholanes with suitably placed hemilabile ligating groups and phosphoramidites derived from binaphthol are excellent ligands for an asymmetric variation of this reaction, the latter giving 99% yield and >95% ee's for selected substrates. An example of how an exocyclic chiral center can be used to install other stereo-centers in the ring (e. g., the carbon to which the side chain is attached) is also provided. These discoveries open an expeditious entry into several biologically relevant classes of compounds, especially those carrying tetrahydronaphthalene and related heterocyclic moieties.

  DOI：

  10.1021/ja0561338