4-Nitro-6,7,8-trihydro-cyclopent-5H-(b)-indol | 13687-73-5

• 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: 4-Nitro-6,7,8-trihydro-cyclopent-5H-(b)-indol
• 英文别名: 5-nitro-1,2,3,4-tetrahydro-cyclopent[b]indole；5-Nitro-1,2,3,4-tetrahydro-cyclopent[b]indol；5-Nitro-1,2,3,4-tetrahydrocyclopenta[b]indole；5-nitro-1,2,3,4-tetrahydrocyclopenta[b]indole
• CAS: 13687-73-5
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: FYWZHJNDYBZUIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  trifluoroacetic acid 1-(1-cyclopenten-1-yl)-2-(2-nitrophenyl)hydrazide 反应 10.0h， 以17%的产率得到4-Nitro-6,7,8-trihydro-cyclopent-5H-(b)-indol
  参考文献：
  名称：

  Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines

  摘要：

  [3,3]-Sigmatropic rearrangement of N-triflluoroacetyl enehydrazines provides a novel method for the construction of indoles. N-Trifluoroacetyl enehydrazine having a cyclopentene ring smoothly underwent [3,3]-sign-tatropic rearrangement followed by cyclization to give indolines in excellent yield. On the other hand, both cyclohexenyl N-trifluoroacetyl enchydrazine and acyclic N-trifluoroacetyl enehydrazine gave indoles in good yield. Additionally, the substituent effect on the benzene ring was also studied. The rearrangement of N-trifluoroacetyl enchydrazines proceeded smoothly even Linder either aqueous or solvent-free conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.087

文献信息

• Plant, Journal of the Chemical Society, 1929, p. 2497
  作者：Plant

  DOI：——

  日期：——
• Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines
  作者：Okiko Miyata、Norihiko Takeda、Yasuo Kimura、Yoshiji Takemoto、Norimitsu Tohnai、Mikiji Miyata、Takeaki Naito

  DOI：10.1016/j.tet.2006.01.087

  日期：2006.4

  [3,3]-Sigmatropic rearrangement of N-triflluoroacetyl enehydrazines provides a novel method for the construction of indoles. N-Trifluoroacetyl enehydrazine having a cyclopentene ring smoothly underwent [3,3]-sign-tatropic rearrangement followed by cyclization to give indolines in excellent yield. On the other hand, both cyclohexenyl N-trifluoroacetyl enchydrazine and acyclic N-trifluoroacetyl enehydrazine gave indoles in good yield. Additionally, the substituent effect on the benzene ring was also studied. The rearrangement of N-trifluoroacetyl enchydrazines proceeded smoothly even Linder either aqueous or solvent-free conditions. (c) 2006 Elsevier Ltd. All rights reserved.