1,2-dihydrocyclobutaphenanthren-1-ol | 144493-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,2-dihydrocyclobutaphenanthren-1-ol
• 英文别名: cyclobutenol；1,2-Dihydrocyclobuta[l]phenanthren-1-ol
• CAS: 144493-73-2
• 化学式: C₁₆H₁₂O
• 分子量: 220.271
• InChiKey: WYQCJKZBXAVILO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-dihydrocyclobutaphenanthren-1-ol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.33h， 生成
  参考文献：
  名称：

  热力学稳定的邻二甲基甲烷：合成，结构和反应性

  摘要：

  研究了环丁菲向邻喹啉甲烷的热异构化。四元环上的立体拥挤的取代基或给电子的取代基促进了开环，从而提供了相对稳定的邻喹啉甲烷。对新制备的邻喹啉甲烷的分离可对其结构进行阐明，并对其潜在的反应性进行研究。亚芳基和邻喹二甲烷的双[4 + 2]环加成反应得到四苯并五并苯，证明了该分离化合物的合成应用。

  DOI：

  10.1002/chem.202004510
• 作为产物：
  描述：

  9-溴菲 在 盐酸 、 sodium tetrahydroborate 、 sodium amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 21.0h， 生成 1,2-dihydrocyclobutaphenanthren-1-ol
  参考文献：
  名称：

  Rapid, convergent, and regioselective synthesis of anthracenes

  摘要：

  Anthracenes are obtained in moderate to good yield by the simultaneous treatment of benzocyclobutenols and halobenzenes with LTMP in tetrahydropyran. In the key step of this one-pot process, o-toluoyl anion intermediates from the known ring-opening of benzocyclobutenoxides add to halobenzene derived arynes. Methoxy-substituted benzocyclobutenols which are readily made regiospecifically by known methods also react regiospecifically with the single benzyne generated from either a 2- or 3-haloanisole. For example, the only trimethoxyanthracene isolated (48% yield) from the reaction of 6-methoxybenzocyclobutenol (8) with 5-chloro-1,3-dimethoxybenzene is the 1,3,8-isomer 20. When 1,2-dihydrocyclobuta[l]phenanthren-1-ol (14) and/or halonaphthalenes are the reactants, benzannulated anthracenes are formed; e.g., tribenz[a,c,h]anthracene in 68% yield from 14 and bromonaphthalene. In another extension, pentaphene (31) was made in one pot from o-dichlorobenzene.

  DOI：

  10.1021/jo00052a027

文献信息

• Rapid, convergent, and regioselective synthesis of anthracenes
  作者：John J. Fitzgerald、Neville E. Drysdale、R. A. Olofson

  DOI：10.1021/jo00052a027

  日期：1992.12

  Anthracenes are obtained in moderate to good yield by the simultaneous treatment of benzocyclobutenols and halobenzenes with LTMP in tetrahydropyran. In the key step of this one-pot process, o-toluoyl anion intermediates from the known ring-opening of benzocyclobutenoxides add to halobenzene derived arynes. Methoxy-substituted benzocyclobutenols which are readily made regiospecifically by known methods also react regiospecifically with the single benzyne generated from either a 2- or 3-haloanisole. For example, the only trimethoxyanthracene isolated (48% yield) from the reaction of 6-methoxybenzocyclobutenol (8) with 5-chloro-1,3-dimethoxybenzene is the 1,3,8-isomer 20. When 1,2-dihydrocyclobuta[l]phenanthren-1-ol (14) and/or halonaphthalenes are the reactants, benzannulated anthracenes are formed; e.g., tribenz[a,c,h]anthracene in 68% yield from 14 and bromonaphthalene. In another extension, pentaphene (31) was made in one pot from o-dichlorobenzene.
• Thermodynamically Stable <i>o</i> ‐Quinodimethane: Synthesis, Structure, and Reactivity
  作者：Kazuhiko Adachi、Shunsuke Hirose、Yasuyuki Ueda、Hidehiro Uekusa、Toshiyuki Hamura

  DOI：10.1002/chem.202004510

  日期：2021.2.19

  o‐quinodimethane was investigated. Sterically congested substituents or electron‐donating substituents on the four‐membered ring promoted the ring‐opening, affording o‐quinodimethane in a relatively stable form. Isolation of the newly prepared o‐quinodimethane allowed its structural elucidation and investigation of its potential reactivities. Dual [4+2] cycloaddition of an aryne and o‐quinodimethane

  研究了环丁菲向邻喹啉甲烷的热异构化。四元环上的立体拥挤的取代基或给电子的取代基促进了开环，从而提供了相对稳定的邻喹啉甲烷。对新制备的邻喹啉甲烷的分离可对其结构进行阐明，并对其潜在的反应性进行研究。亚芳基和邻喹二甲烷的双[4 + 2]环加成反应得到四苯并五并苯，证明了该分离化合物的合成应用。