1-(3-Diphenylphosphoryl-3-phenylpropa-1,2-dienyl)-2-[2-(4-methylphenyl)ethynyl]benzene | 182920-45-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-(3-Diphenylphosphoryl-3-phenylpropa-1,2-dienyl)-2-[2-(4-methylphenyl)ethynyl]benzene
• CAS: 182920-45-2
• 化学式: C₃₆H₂₇OP
• 分子量: 506.584
• InChiKey: YWCUPLSZKBCEGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-Diphenylphosphoryl-3-phenylpropa-1,2-dienyl)-2-[2-(4-methylphenyl)ethynyl]benzene 以63%的产率得到10-(Diphenyl-phosphinoyl)-5-p-tolyl-11H-benzo[b]fluorene
  参考文献：
  名称：

  烯炔-丙二烯热解中的环应变效应：从Myers-Saito反应转变为C 2 -C 6双自由基环化[1]

  摘要：

  烯炔-丙烯1的热环化模式取决于环应变效应：当烯官能团是苯，环己烯或环庚烯环的一部分时，观察到新型C 2 -C 6双自由基环化，而当它是a的一部分时Myers-Saito环芳环化反应的环戊烯环已注册。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)01393-2
• 作为产物：
  描述：

  2-[ 2 -(4-甲基苯基)乙炔基]苯甲醛 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1-(3-Diphenylphosphoryl-3-phenylpropa-1,2-dienyl)-2-[2-(4-methylphenyl)ethynyl]benzene
  参考文献：
  名称：

  A Surprising Switch from the Myers–Saito Cyclization to a Novel Biradical Cyclization in Enyne–Allenes: Formal Diels–Alder and Ene Reactions with High Synthetic Potential

  摘要：

  AbstractIf there is an aryl substituent on the acetylene terminus of enyne‐allenes, then its reaction mode may be changed from the Myers‐Saito cyclization to a novel C2–C6 cyclization resulting in a net intramolecular Diels‐Alder or ene reaction. As a consequence, the thermal cyclization of readily accessible acyclic enyne‐allenes can be utilized for the synthesis of complex benzofulvene and benzofluorene derivatives. Kinetic results of the C2–C6 cyclization reaction indicate a two‐step reaction pathway with a benzofulvene biradical intermediate.

  DOI：

  10.1002/chem.19970030521

文献信息

• Ring Strain Effects in Enyne-Allene Thermolysis: Switch from the Myers-Saito Reaction to the C2-C6 Biradical Cyclization
  作者：Michael Schmittel、Jens-Peter Steffen、Dominik Auer、Michael Maywald

  DOI：10.1016/s0040-4039(97)01393-2

  日期：1997.9

  The mode of the thermal cyclization of enyne-allenes 1 depends on ring strain effects: when the ene functionality is part of a benzene, cyclohexene or cycloheptene ring the novel C2-C6 biradical cyclization is observed, while when it is part of a cyclopentene ring the Myers-Saito cycloaromatization is registered. © 1997 Elsevier Science Ltd.

  烯炔-丙烯1的热环化模式取决于环应变效应：当烯官能团是苯，环己烯或环庚烯环的一部分时，观察到新型C 2 -C 6双自由基环化，而当它是a的一部分时Myers-Saito环芳环化反应的环戊烯环已注册。©1997爱思唯尔科学有限公司。
• A Surprising Switch from the Myers–Saito Cyclization to a Novel Biradical Cyclization in Enyne–Allenes: Formal Diels–Alder and Ene Reactions with High Synthetic Potential
  作者：Michael Schmittel、Manfred Keller、Susanne Kiau、Marc Strittmatter

  DOI：10.1002/chem.19970030521

  日期：1997.5

  AbstractIf there is an aryl substituent on the acetylene terminus of enyne‐allenes, then its reaction mode may be changed from the Myers‐Saito cyclization to a novel C2–C6 cyclization resulting in a net intramolecular Diels‐Alder or ene reaction. As a consequence, the thermal cyclization of readily accessible acyclic enyne‐allenes can be utilized for the synthesis of complex benzofulvene and benzofluorene derivatives. Kinetic results of the C2–C6 cyclization reaction indicate a two‐step reaction pathway with a benzofulvene biradical intermediate.