1-Cyclohexyl-4,5-dihydropyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 1-Cyclohexyl-4,5-dihydropyrazole
• 英文别名: 1-cyclohexyl-4,5-dihydro-1H-pyrazole；2-cyclohexyl-3,4-dihydropyrazole
• 化学式: C₉H₁₆N₂
• 分子量: 152.239
• InChiKey: OHDOLGCGGADHNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  15.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-(3-azidopropyl)cyclohexanamine 在 iron(III) chloride 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 0.5h， 以73%的产率得到1-Cyclohexyl-4,5-dihydropyrazole
  参考文献：
  名称：

  Fe(III)-Catalyzed Aerobic Intramolecular N–N Coupling of Aliphatic Azides with Amines

  摘要：

  An Fe(III)-catalyzed intramolecular N-N coupling of aliphatic azidoamines that forms diverse five-and six-membered semisaturated diazoheterocycles using air as an oxidant is reported, providing an alternative to hydrazine-based methods. Mechanistic studies suggest that a N-radical induced intramolecular homolytic substitution (S(H)2) is involved in ring closure. The power of this N-N bond-forming method is also demonstrated by using it as the final step in a total synthesis of (-)-newbouldine.

  DOI：

  10.1021/acs.orglett.9b01396

文献信息

• Koptelov; Molchanov; Kostikov, Russian Journal of Organic Chemistry, 2000, vol. 36, # 7, p. 1025 - 1026
  作者：Koptelov、Molchanov、Kostikov

  DOI：——

  日期：——
• Fe(III)-Catalyzed Aerobic Intramolecular N–N Coupling of Aliphatic Azides with Amines
  作者：Yue Zhang、Dongyu Duan、Ying Zhong、Xin-Ai Guo、Jiawei Guo、Jing Gou、Ziwei Gao、Binxun Yu

  DOI：10.1021/acs.orglett.9b01396

  日期：2019.7.5

  An Fe(III)-catalyzed intramolecular N-N coupling of aliphatic azidoamines that forms diverse five-and six-membered semisaturated diazoheterocycles using air as an oxidant is reported, providing an alternative to hydrazine-based methods. Mechanistic studies suggest that a N-radical induced intramolecular homolytic substitution (S(H)2) is involved in ring closure. The power of this N-N bond-forming method is also demonstrated by using it as the final step in a total synthesis of (-)-newbouldine.