2-methyl-3-phenyl-3,3a,4,5,6,7-hexahydro-2H-imidazole | 144202-85-7

• 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: 2-methyl-3-phenyl-3,3a,4,5,6,7-hexahydro-2H-imidazole
• 英文别名: 2-methyl-3-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole；3,3a,4,5,6,7-hexahydro-2-methyl-3-phenyl-2H-indazole；2-Methyl-3-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole；2-methyl-3-phenyl-3,3a,4,5,6,7-hexahydroindazole
• CAS: 144202-85-7
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: HFXZIDGPVBVXAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-phenyl-3,3a,4,5,6,7-hexahydro-2H-imidazole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到2-甲基-3-苯基吲唑
  参考文献：
  名称：

  Synthesis of hydrogenated indazole derivatives starting with α,β-unsaturated ketones and hydrazine derivatives

  摘要：

  The reaction of hydrazine derivatives with alpha,beta-unsaturated ketones, such as cyclohexenyl(phenyl) methanone and (E)-2-benzylidenecyclohexanone, were investigated.The reaction between methylhydrazine and e.g., cyclohexenyl(phenyl)methanone was particularly interesting as 3a,4,5,6,7,7a-hexahydro-1-methyl-3-phenyl-1H-indazole was obtained as the major product together with 4,5,6,7-tetrahydro-2-methyl-3-phenyl-2H-indazole as a minor product. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.041
• 作为产物：
  描述：

  (E)-2-benzylidenecyclohexanone 、 甲基肼 以 异丙醇 为溶剂， 以99%的产率得到2-methyl-3-phenyl-3,3a,4,5,6,7-hexahydro-2H-imidazole
  参考文献：
  名称：

  Synthesis of hydrogenated indazole derivatives starting with α,β-unsaturated ketones and hydrazine derivatives

  摘要：

  The reaction of hydrazine derivatives with alpha,beta-unsaturated ketones, such as cyclohexenyl(phenyl) methanone and (E)-2-benzylidenecyclohexanone, were investigated.The reaction between methylhydrazine and e.g., cyclohexenyl(phenyl)methanone was particularly interesting as 3a,4,5,6,7,7a-hexahydro-1-methyl-3-phenyl-1H-indazole was obtained as the major product together with 4,5,6,7-tetrahydro-2-methyl-3-phenyl-2H-indazole as a minor product. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.041

文献信息

• Synthesis of Bicyclic<i>N</i>-Methylpyrazoline and Pyrazole Derivatives from α,β-Unsaturated Ketones and<i>N</i>,<i>N</i>-Dimethylhydrazine: An Illustration of Reductive Cyclization
  作者：A. K. Panda、U. Das、J. W. Quail、J. R. Dimmock

  DOI：10.1002/jhet.1570

  日期：2014.1

  The reaction of N,N‐dimethylhydrazine with α,β‐unsaturated keto precursors such as 2‐benzylidenecyclohexanone, 2,6‐bis(benzylidene)cyclohexanone, and 3,5‐bis(benzylidene)‐1‐methyl‐4‐piperidone hydrochloride provided bicyclic N‐methylpyrazoles instead of hydrazones or any Michael addition products. The crystal structure of a representative pyrazole is reported. The proposed mechanism for the formation

  N，N-二甲基肼与α，β-不饱和酮前体的反应，例如2-苄叉基环己酮，2,6-双（苄叉基）环己酮和3,5-双（苄叉基）-1-甲基-4-哌啶酮盐酸盐提供了双环N-甲基吡唑类化合物，而不是或任何迈克尔加成产物。报告了代表性的吡唑的晶体结构。概述了形成双环N-甲基吡唑1的机制。
• Synthesis of hydrogenated indazole derivatives starting with α,β-unsaturated ketones and hydrazine derivatives
  作者：Azadeh Nakhai、Jan Bergman

  DOI：10.1016/j.tet.2009.01.041

  日期：2009.3

  The reaction of hydrazine derivatives with alpha,beta-unsaturated ketones, such as cyclohexenyl(phenyl) methanone and (E)-2-benzylidenecyclohexanone, were investigated.The reaction between methylhydrazine and e.g., cyclohexenyl(phenyl)methanone was particularly interesting as 3a,4,5,6,7,7a-hexahydro-1-methyl-3-phenyl-1H-indazole was obtained as the major product together with 4,5,6,7-tetrahydro-2-methyl-3-phenyl-2H-indazole as a minor product. (C) 2009 Elsevier Ltd. All rights reserved.