trifluoroacetic acid 1-(1-cyclopenten-1-yl)-2-(2-nitrophenyl)hydrazide | 256442-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trifluoroacetic acid 1-(1-cyclopenten-1-yl)-2-(2-nitrophenyl)hydrazide
• 英文别名: N-(cyclopenten-1-yl)-2,2,2-trifluoro-N'-(2-nitrophenyl)acetohydrazide
• CAS: 256442-16-7
• 化学式: C₁₃H₁₂F₃N₃O₃
• 分子量: 315.252
• InChiKey: SEMZSCDTWWLEID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trifluoroacetic acid 1-(1-cyclopenten-1-yl)-2-(2-nitrophenyl)hydrazide 以 甲苯 为溶剂， 反应 29.0h， 以31%的产率得到(+/-)-cis-3a-[(trifluoroacetyl)amino]-1,2,3,3a,4,8b-hexahydro-5-nitrocyclopent[b]indole
  参考文献：
  名称：

  Unambiguous characterisation of dienylimines as intermediates in Fischer indolisation of o-substituted N-trifluoroacetyl enehydrazines

  摘要：

  经系统研究，发现邻位取代的N-三氟乙酰烯酮肼通过二烯亚胺中间体进行热环化反应，并通过晶体衍射和光谱分析明确鉴定了这些中间体。

  DOI：

  10.1039/a907539i
• 作为产物：
  描述：

  2-硝基苯肼 在 2,4,6-三甲基吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 trifluoroacetic acid 1-(1-cyclopenten-1-yl)-2-(2-nitrophenyl)hydrazide
  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

• Unambiguous characterisation of dienylimines as intermediates in Fischer indolisation of o-substituted N-trifluoroacetyl enehydrazines
  作者：Okiko Miyata、Yasuo Kimura、Takeaki Naito

  DOI：10.1039/a907539i

  日期：——

  Thermal cyclisation of o-substituted N-trifluoroacetyl enehydrazines was systematically investigated and found to proceed via dienylimine intermediates, which were unambiguously characterised by X-ray and spectral analysis.

  经系统研究，发现邻位取代的N-三氟乙酰烯酮肼通过二烯亚胺中间体进行热环化反应，并通过晶体衍射和光谱分析明确鉴定了这些中间体。
• 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.