trifluoroacetic acid 1-(1-cyclohexen-1-yl)-2-(2-methoxyphenyl)hydrazide | 256442-12-3

• 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-cyclohexen-1-yl)-2-(2-methoxyphenyl)hydrazide
• 英文别名: N-(cyclohexen-1-yl)-2,2,2-trifluoro-N'-(2-methoxyphenyl)acetohydrazide
• CAS: 256442-12-3
• 化学式: C₁₅H₁₇F₃N₂O₂
• 分子量: 314.307
• InChiKey: CKJFMTCBRXKQSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trifluoroacetic acid 1-(1-cyclohexen-1-yl)-2-(2-methoxyphenyl)hydrazide 以 甲苯 为溶剂， 反应 10.0h， 以75%的产率得到1,2,3,4-tetrahydro-8-methoxy-9H-carbazole
  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-甲氧基苯肼 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-cyclohexen-1-yl)-2-(2-methoxyphenyl)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

• Michael Addition–Aromatization Reaction of Dienylimines Bearing a Leaving Group and Its Application to the Preparation of Thiol-Selective Labeling Reagents Capable of Forming Strong Carbon–Sulfur Bonds
  作者：Tetsuya Miyoshi、Yuka Aoki、Yumina Uno、Mina Araki、Takahiro Kamatani、Daichi Fujii、Yoshinori Fujita、Norihiko Takeda、Masafumi Ueda、Hiroshi Kitagawa、Noriaki Emoto、Takahiro Mukai、Masafumi Tanaka、Okiko Miyata

  DOI：10.1021/jo402002k

  日期：2013.11.15

  The reaction of a dienylimine with thiols was found to proceed smoothly to afford the corresponding indolines bearing aromatic carbon-sulfur bonds as a result of a Michael addition-aromatization sequence. Furthermore, this reaction was applied to the development of fluorogenic dienylimines that could be used as thiol-selective fluorescent labeling reagents.