6-methoxy-4,7-dimethyl-5-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-3-carbonitrile | 205177-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-methoxy-4,7-dimethyl-5-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-3-carbonitrile
• CAS: 205177-70-4
• 化学式: C₁₅H₁₅N₃O₃
• 分子量: 285.302
• InChiKey: QYLYGCMDSZCGEF-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  551.013±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.389±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxy-4,7-dimethyl-5-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-3-carbonitrile 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -20.0 ℃ 、344.73 kPa 条件下， 反应 6.17h， 生成
  参考文献：
  名称：

  Design of a Cyclopropyl Quinone Methide Reductive Alkylating Agent

  摘要：

  Described herein is the formation of a cyclopropyl quinone methide species by leaving group elimination from an indole-based hydroquinone. This species is structurally related to the A-ring of CC-1065 and is a nucleophile trap. In addition, the cyclopropyl quinone methide species can trap or eliminate a proton. Unlike the A-ring of CC-1065, stereoelectronic factors favor opening of the fused cyclopropane ring so as to result in ring expansion. Also described herein is the utility of C-13 NMR spectroscopy in following the fate of the cyclopropyl quinone methide species. Finally, the cyclopropyl quinone methide species reversibly alkylates the guanine N(7) position of DNA, resulting in cytotoxicity.

  DOI：

  10.1021/jo971808d
• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 6-Methoxy-4,7-dimethyl-5-nitro-1,2-dihydropyrrolo[1,2-a]indol-3-one 在 sodium ethanolate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 以42%的产率得到6-methoxy-4,7-dimethyl-5-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole-3-carbonitrile
  参考文献：
  名称：

  Design of a Cyclopropyl Quinone Methide Reductive Alkylating Agent

  摘要：

  Described herein is the formation of a cyclopropyl quinone methide species by leaving group elimination from an indole-based hydroquinone. This species is structurally related to the A-ring of CC-1065 and is a nucleophile trap. In addition, the cyclopropyl quinone methide species can trap or eliminate a proton. Unlike the A-ring of CC-1065, stereoelectronic factors favor opening of the fused cyclopropane ring so as to result in ring expansion. Also described herein is the utility of C-13 NMR spectroscopy in following the fate of the cyclopropyl quinone methide species. Finally, the cyclopropyl quinone methide species reversibly alkylates the guanine N(7) position of DNA, resulting in cytotoxicity.

  DOI：

  10.1021/jo971808d

文献信息

• Design of a Cyclopropyl Quinone Methide Reductive Alkylating Agent
  作者：Anlong Ouyang、Edward B. Skibo

  DOI：10.1021/jo971808d

  日期：1998.3.1

  Described herein is the formation of a cyclopropyl quinone methide species by leaving group elimination from an indole-based hydroquinone. This species is structurally related to the A-ring of CC-1065 and is a nucleophile trap. In addition, the cyclopropyl quinone methide species can trap or eliminate a proton. Unlike the A-ring of CC-1065, stereoelectronic factors favor opening of the fused cyclopropane ring so as to result in ring expansion. Also described herein is the utility of C-13 NMR spectroscopy in following the fate of the cyclopropyl quinone methide species. Finally, the cyclopropyl quinone methide species reversibly alkylates the guanine N(7) position of DNA, resulting in cytotoxicity.