N-methyl-4,5-bis(trimethylsiloxy)-cis-Δ⁴-tetrahydrophthalimide | 145159-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-methyl-4,5-bis(trimethylsiloxy)-cis-Δ⁴-tetrahydrophthalimide
• 英文别名: (3aS,7aR)-2-methyl-5,6-bis(trimethylsilyloxy)-3a,4,7,7a-tetrahydroisoindole-1,3-dione
• CAS: 145159-79-1
• 化学式: C₁₅H₂₇NO₄Si₂
• 分子量: 341.555
• InChiKey: ASDXVUJYYZRVSW-PHIMTYICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  N-methyl-4,5-bis(trimethylsiloxy)-cis-Δ⁴-tetrahydrophthalimide 在 palladium on activated charcoal 、 polyphosphoric acid trimethylsilyl ester 、 间氯过氧苯甲酸 作用下， 反应 16.5h， 生成 N6-methylarcyriaflavin A
  参考文献：
  名称：

  Synthetic Approaches to Indolo[2,3-a]carbazole alkaloids. Syntheses of arcyriaflavin A and AT2433-B aglycone

  摘要：

  Ozonolysis of tetrahydrophthalimides 17 and 18 or cyclohexane diester 25 and treatment of the intermediate dialdehydes (19, 20, 26) with an arylhydrazine affords the corresponding bis-arylhydrazones (21-24, 27, 28). Exposure of 21 and 23 to PPSE in CH3NO2 gives the indolo[2,3-a]carbazole alkaloids arcyriaflavin A (8) and AT2433-B aglycone (29) in low yield. bis-Phenylhydrazones (osazones) (33, 34, 42, 44) of cyclohexandiones were synthesized by m-CPBA oxidation of 4,5-bis(trimethylsilyloxy)tetrahydrophthalimides followed by treatment of the presumed intermediate 1,2-cyclohexanediones with an arylhydrazine. These osazones were cyclized to the corresponding indolo[2,3-a]carbazoles with PPSE.

  DOI：

  10.1016/s0040-4020(01)81986-4
• 作为产物：
  描述：

  N-甲基马来酰亚胺 、 2,3-二(三甲基甲硅烷氧基)-1,3-丁二烯 以 甲苯 为溶剂， 以89%的产率得到N-methyl-4,5-bis(trimethylsiloxy)-cis-Δ⁴-tetrahydrophthalimide
  参考文献：
  名称：

  Synthetic Approaches to Indolo[2,3-a]carbazole alkaloids. Syntheses of arcyriaflavin A and AT2433-B aglycone

  摘要：

  Ozonolysis of tetrahydrophthalimides 17 and 18 or cyclohexane diester 25 and treatment of the intermediate dialdehydes (19, 20, 26) with an arylhydrazine affords the corresponding bis-arylhydrazones (21-24, 27, 28). Exposure of 21 and 23 to PPSE in CH3NO2 gives the indolo[2,3-a]carbazole alkaloids arcyriaflavin A (8) and AT2433-B aglycone (29) in low yield. bis-Phenylhydrazones (osazones) (33, 34, 42, 44) of cyclohexandiones were synthesized by m-CPBA oxidation of 4,5-bis(trimethylsilyloxy)tetrahydrophthalimides followed by treatment of the presumed intermediate 1,2-cyclohexanediones with an arylhydrazine. These osazones were cyclized to the corresponding indolo[2,3-a]carbazoles with PPSE.

  DOI：

  10.1016/s0040-4020(01)81986-4

文献信息

• Synthetic Approaches to Indolo[2,3-a]carbazole alkaloids. Syntheses of arcyriaflavin A and AT2433-B aglycone
  作者：Gordon W. Gribble、Steven J. Berthel

  DOI：10.1016/s0040-4020(01)81986-4

  日期：——

  Ozonolysis of tetrahydrophthalimides 17 and 18 or cyclohexane diester 25 and treatment of the intermediate dialdehydes (19, 20, 26) with an arylhydrazine affords the corresponding bis-arylhydrazones (21-24, 27, 28). Exposure of 21 and 23 to PPSE in CH3NO2 gives the indolo[2,3-a]carbazole alkaloids arcyriaflavin A (8) and AT2433-B aglycone (29) in low yield. bis-Phenylhydrazones (osazones) (33, 34, 42, 44) of cyclohexandiones were synthesized by m-CPBA oxidation of 4,5-bis(trimethylsilyloxy)tetrahydrophthalimides followed by treatment of the presumed intermediate 1,2-cyclohexanediones with an arylhydrazine. These osazones were cyclized to the corresponding indolo[2,3-a]carbazoles with PPSE.