3,3'-(1,2-phenylene)bis(1,4-diphenyl)azetidin-2-one | 1009075-87-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,3'-(1,2-phenylene)bis(1,4-diphenyl)azetidin-2-one
• 英文别名: (3S,4R)-3-[2-[(3R,4S)-2-oxo-1,4-diphenylazetidin-3-yl]phenyl]-1,4-diphenylazetidin-2-one
• CAS: 1009075-87-9
• 化学式: C₃₆H₂₈N₂O₂
• 分子量: 520.631
• InChiKey: HHEXUHNTVYCYFR-WKKVWOBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  o-Phenylendiessigsaeure-dichlorid 、 (E)-N-benzylidenebenzenamine 在 1,8-双二甲氨基萘 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以200 mg的产率得到3,3'-(1,2-phenylene)bis(1,4-diphenyl)azetidin-2-one
  参考文献：
  名称：

  Spiro-Aziridine and Bislactam Formation from Bisketene−Imine Cycloadditions

  摘要：

  1,2-Bisketenes 6 react with imines PhCH=NAr, (E)-2, forming spiro-aziridines 7. DFT computations indicate that this occurs by nucleophilic attack of the imine on the carbonyl carbon of the more reactive arylketene moiety, followed by cyclization, and not by prior cyclization of the 1,2-bisketene forming a carbene lactone intermediate. Computations also indicate that the previously studied bisketene 10 from benzocyclobutadiene 9 is 4.0 kcal/mol less stable than carbene lactone 12 that would result from cyclization but that the failure to observe 12 results from a lower barrier for 10 to instead revert to 9. 1,2-, 1,3-, and 1,4-Bisketenylbenzenes 16, 19, and 22 react with imines forming bis(beta- lactams), with a preference for formation of mixtures of trans, trans chiral (+/-) and achiral diastereomeric products.

  DOI：

  10.1021/ja077623y

文献信息

• Spiro-Aziridine and Bislactam Formation from Bisketene−Imine Cycloadditions
  作者：Annette D. Allen、Jazmin Godoy、Nanyan Fu、Michelle Nagy、Sandra Spadaro、Thomas T. Tidwell、Sinisa Vukovic

  DOI：10.1021/ja077623y

  日期：2008.2.1

  1,2-Bisketenes 6 react with imines PhCH=NAr, (E)-2, forming spiro-aziridines 7. DFT computations indicate that this occurs by nucleophilic attack of the imine on the carbonyl carbon of the more reactive arylketene moiety, followed by cyclization, and not by prior cyclization of the 1,2-bisketene forming a carbene lactone intermediate. Computations also indicate that the previously studied bisketene 10 from benzocyclobutadiene 9 is 4.0 kcal/mol less stable than carbene lactone 12 that would result from cyclization but that the failure to observe 12 results from a lower barrier for 10 to instead revert to 9. 1,2-, 1,3-, and 1,4-Bisketenylbenzenes 16, 19, and 22 react with imines forming bis(beta- lactams), with a preference for formation of mixtures of trans, trans chiral (+/-) and achiral diastereomeric products.