3,4,6,8,9-pentaphenyl-5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-dione | 1341189-45-4

• 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: 3,4,6,8,9-pentaphenyl-5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-dione
• 英文别名: 3,4,6,8,9-Pentakis-phenyl-5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-dione
• CAS: 1341189-45-4
• 化学式: C₃₈H₂₇NO₄
• 分子量: 561.637
• InChiKey: AOPBOVNBEOUUEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 3,4,6,8,9-pentaphenyl-5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-dione 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到(Z)-methyl 3-(5-oxo-2,6,7-triphenyl-2,3,4,5-tetrahydro-1,4-oxazepin-2-yloxy)-2,3-diphenylacrylate
  参考文献：
  名称：

  Nonconcerted Cycloaddition of 2H-Azirines to Acylketenes: A Route to N-Bridgehead Heterocycles

  摘要：

  Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene. According to DFT B3LYP/6-31G(d) computations, the formation of (4+2)-monoadducts proceeds via a stepwise non-pericyclic mechanism. Reaction with methanol transforms quantitatively both 1:1 and 2:1 adducts into 1,4-oxazepine derivatives.

  DOI：

  10.1021/jo201563b
• 作为产物：
  描述：

  (1Z)-2-偶氮基-3-氧代-1,3-二苯基-1-丙烯-1-醇 、 3-phenyl-2H-azirine 以 甲苯 为溶剂， 反应 2.0h， 以70%的产率得到3,4,6,8,9-pentaphenyl-5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-dione
  参考文献：
  名称：

  Nonconcerted Cycloaddition of 2H-Azirines to Acylketenes: A Route to N-Bridgehead Heterocycles

  摘要：

  Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene. According to DFT B3LYP/6-31G(d) computations, the formation of (4+2)-monoadducts proceeds via a stepwise non-pericyclic mechanism. Reaction with methanol transforms quantitatively both 1:1 and 2:1 adducts into 1,4-oxazepine derivatives.

  DOI：

  10.1021/jo201563b

文献信息

• Domino reactions of 2<i>H</i>-azirines with acylketenes from furan-2,3-diones: Competition between the formation of <i>ortho</i>-fused and bridged heterocyclic systems
  作者：Alexander F Khlebnikov、Mikhail S Novikov、Viktoriia V Pakalnis、Roman O Iakovenko、Dmitry S Yufit

  DOI：10.3762/bjoc.10.74

  日期：——

  prepared only from 3-aryl-2H-azirines having no electron-withdrawing groups in the aryl substituent. Calculations at the DFT B3LYP/6-31G(d) level for the various routes of bis[1,3]oxazino[3,2-a:3',2'-d]pyrazine skeleton formation revealed a new domino reaction of 3-aryl-2H-azirines occurring in the presence of furandiones: acid-catalyzed dimerization to dihydropyrazine followed by consecutive cycloaddition

  3-芳基-2H-氮丙啶与通过 5-芳基呋喃-2,3-二酮热解产生的酰基乙烯酮反应，得到桥联 5,7-二氧杂-1-氮杂双环[4.4.1]undeca-3,8-二烯- 2,10-二酮和/或邻位稠合的6,6a,12,12a-四氢双[1,3]恶嗪基[3,2-a:3',2'-d]吡嗪-4,10-二酮。后者具有新的杂环骨架，是两分子氮丙啶和两分子酰基乙烯酮偶联的结果，并且只能由芳基取代基中不具有吸电子基团的3-芳基-2H-氮丙啶制备。在 DFT B3LYP/6-31G(d) 水平上对双[1,3]恶嗪基[3,2-a:3',2'-d]吡嗪骨架形成的各种途径的计算揭示了新的多米诺骨牌反应 3 -芳基-2H-氮丙啶在呋喃二酮存在下发生：酸催化二聚成二氢吡嗪，然后将后者连续环加成到两个酰基乙烯酮分子上。
• Nonconcerted Cycloaddition of 2<i>H</i>-Azirines to Acylketenes: A Route to N-Bridgehead Heterocycles
  作者：Alexander F. Khlebnikov、Mikhail S. Novikov、Viktoriia V. Pakalnis、Dmitry S. Yufit

  DOI：10.1021/jo201563b

  日期：2011.11.18

  Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene. According to DFT B3LYP/6-31G(d) computations, the formation of (4+2)-monoadducts proceeds via a stepwise non-pericyclic mechanism. Reaction with methanol transforms quantitatively both 1:1 and 2:1 adducts into 1,4-oxazepine derivatives.