1-cyclohexen-1-yl-1-(diphenylphosphinyl)ethene | 178943-29-8

• 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: 1-cyclohexen-1-yl-1-(diphenylphosphinyl)ethene
• 英文别名: [1-(Cyclohex-1-en-1-yl)ethenyl](oxo)diphenyl-lambda~5~-phosphane；[1-(cyclohexen-1-yl)ethenyl-phenylphosphoryl]benzene
• CAS: 178943-29-8
• 化学式: C₂₀H₂₁OP
• 分子量: 308.36
• InChiKey: WHYACTOBJKCMOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  505.6±23.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-乙炔基环己烷 、 四苯基二膦 在 四(三苯基膦)钯 二乙基甲基硅烷 、 air 作用下， 以 氘代苯 为溶剂， 反应 18.0h， 以41%的产率得到1-cyclohexen-1-yl-1-(diphenylphosphinyl)ethene
  参考文献：
  名称：

  A Highly Regioselective Palladium-Catalyzed Hydrophosphination of Alkynes Using a Diphosphine−Hydrosilane Binary System

  摘要：

  A novel transition-metal-catalyzed hydrophosphination of terminal alkynes using a diphosphine-hydrosilane binary system takes place regioselectively to provide vinylic phosphines, which undergo air oxidation during workup, affording the corresponding vinylphosphine oxides in good yields. In this hydrophosphination, hydrosilanes act as a useful hydrogen source, and furthermore, small amounts of oxygen is required to accomplish the reaction efficiently.

  DOI：

  10.1021/jo801267y

文献信息

• Phosphinic Acid Induced Reversal of Regioselectivity in Pd-Catalyzed Hydrophosphinylation of Alkynes with Ph2P(O)H
  作者：Li-Biao Han、Ruimao Hua、Masato Tanaka

  DOI：10.1002/(sici)1521-3773(19980202)37:1/2<94::aid-anie94>3.0.co;2-t

  日期：1998.2.2
• Palladium-complex-catalyzed regioselective Markovnikov addition reaction and dehydrogenative double phosphinylation to terminal alkynes with diphenylphosphine oxide
  作者：Naotomo Dobashi、Kouichiro Fuse、Takako Hoshino、Jun Kanada、Taigo Kashiwabara、Chihiro Kobata、Satish Kumar Nune、Masato Tanaka

  DOI：10.1016/j.tetlet.2007.05.039

  日期：2007.7

  Palladium-1,2-bis(diphenylphosphino)ethane complex catalyzes regioselective Markovnikov addition of diphenylphosphine oxide to terminal alkynes in propionitrile, while the use of triarylphopshines, di(o-tolyl)phenylphosphine in particular, as the ligand leads to dehydrogenative double addition forming 1,2-diphenylphosphinyl-1-alkenes as major products. (c) 2007 Elsevier Ltd. All rights reserved.
• Nickel-Catalyzed Addition of P(O)−H Bonds to Propargyl Alcohols:  One-Pot Generation of Phosphinoyl 1,3-Butadienes
  作者：Li-Biao Han、Yutaka Ono、Hideaki Yazawa

  DOI：10.1021/ol0508431

  日期：2005.7.1

  Diphenylphosphine oxide and related P(O)H compounds react with propargyl alcohols at room temperature in the presence of a catalytic amount of Ni(O) complex and Ph2P(O)OH to produce high yields of phosphinoyl 1,3-dienes though an efficient in situ dehydration process.
• A Highly Regioselective Palladium-Catalyzed Hydrophosphination of Alkynes Using a Diphosphine−Hydrosilane Binary System
  作者：Shin-ichi Kawaguchi、Shoko Nagata、Akihiro Nomoto、Motohiro Sonoda、Akiya Ogawa

  DOI：10.1021/jo801267y

  日期：2008.10.17

  A novel transition-metal-catalyzed hydrophosphination of terminal alkynes using a diphosphine-hydrosilane binary system takes place regioselectively to provide vinylic phosphines, which undergo air oxidation during workup, affording the corresponding vinylphosphine oxides in good yields. In this hydrophosphination, hydrosilanes act as a useful hydrogen source, and furthermore, small amounts of oxygen is required to accomplish the reaction efficiently.