1α-acetoxy-5-carbomethoxy-1,2,4,10bα-tetrahydro-8-methoxy-3a-azabenz[e]azulen-3-one | 171366-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1α-acetoxy-5-carbomethoxy-1,2,4,10bα-tetrahydro-8-methoxy-3a-azabenz[e]azulen-3-one
• 英文别名: methyl (1S,11bR)-1-acetyloxy-9-methoxy-3-oxo-1,2,5,11b-tetrahydropyrrolo[2,1-a][2]benzazepine-6-carboxylate
• CAS: 171366-50-0
• 化学式: C₁₈H₁₉NO₆
• 分子量: 345.352
• InChiKey: ZJRPFKGPOLITDS-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1α-acetoxy-5-carbomethoxy-1,2,4,10bα-tetrahydro-8-methoxy-3a-azabenz[e]azulen-3-one 在 三溴化硼 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.33h， 生成 1α-acetoxy-5-carbomethoxy-10aα-hydroxy-1,2,10aα,10bα-tetrahydro-4H-3a-azabenz[e]azulen-3,8-dione
  参考文献：
  名称：

  An Asymmetric Synthesis of Aza Analogues of the Tricyclic Skeleton of Daphnane and the ABC Ring System of Phorbol

  摘要：

  An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.

  DOI：

  10.1021/jo0205816
• 作为产物：
  描述：

  (Z)-methyl 2-(bromomethyl)-3-(3-methoxyphenyl)acrylate 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成 1α-acetoxy-5-carbomethoxy-1,2,4,10bα-tetrahydro-8-methoxy-3a-azabenz[e]azulen-3-one
  参考文献：
  名称：

  An Asymmetric Synthesis of Aza Analogues of the Tricyclic Skeleton of Daphnane and the ABC Ring System of Phorbol

  摘要：

  An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.

  DOI：

  10.1021/jo0205816

文献信息

• Convergent stereocontrolled construction of 5-7-6 tricyclic aza analogues of phorbol and aconite alkaloids
  作者：Charles M. Marson、Jennifer H. Pink、Christopher Smith

  DOI：10.1016/0040-4039(95)01688-e

  日期：1995.10

  An acyliminium cyclization is used to construct the central seven-membered ring of 5-7-6 tricyclic aza-analogues of diterpenoids.