cis-1,1'-(1,2-Cyclohexanediyl)bis(2-diazoethanone) | 148371-13-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 英文名称: cis-1,1'-(1,2-Cyclohexanediyl)bis(2-diazoethanone)
• 英文别名: 2-diazo-1-[(1R,2S)-2-(2-diazoacetyl)cyclohexyl]ethanone
• CAS: 148371-13-5
• 化学式: C₁₀H₁₂N₄O₂
• 分子量: 220.231
• InChiKey: RAJQDHSPILYKGB-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-1,1'-(1,2-Cyclohexanediyl)bis(2-diazoethanone) 以 甲苯 为溶剂， 以72%的产率得到cis-3a,4,5,6,7,7a-hexahydro-1H-inden-1-one
  参考文献：
  名称：

  Novel synthesis of trans-hydroindenones by thermal reaction of α,ω-bis(diazo)diketones

  摘要：

  δ±，Ï-双（重氮）二酮的热反应产生了δ±²-不饱和环烯酮，包括未取代的反式氢茚酮，这些物质很难通过传统合成反应获得。

  DOI：

  10.1039/c39930000556
• 作为产物：
  描述：

  cis-1,2-cyclohexanedicarboxylic dichloride 、 以 乙醚 为溶剂， 以27%的产率得到cis-1,1'-(1,2-Cyclohexanediyl)bis(2-diazoethanone)
  参考文献：
  名称：

  Novel synthesis of trans-hydroindenones by thermal reaction of α,ω-bis(diazo)diketones

  摘要：

  δ±，Ï-双（重氮）二酮的热反应产生了δ±²-不饱和环烯酮，包括未取代的反式氢茚酮，这些物质很难通过传统合成反应获得。

  DOI：

  10.1039/c39930000556

文献信息

• Intramolecular Cooperative Reactions of 1,2-Bis(diazoketone)s. The First Syntheses of trans-Hydro-1H-2-inden-1-ones
  作者：Kazuhiko Nakatani、Kazunori Takada、Sachihiko Isoe

  DOI：10.1021/jo00113a030

  日期：1995.4

  The intramolecular cooperative reactions of 1,2-bis(diazoketone)s initiated by the Wolff rearrangement of alpha-diazoketones have been investigated. Under thermal conditions, 1,2-bis(diazoketone)s are efficiently transformed into 2-cyclopenten-1-one derivatives with complete stereospecificity. Thus, a most extraordinary result is reported, that trans-hydro-2-inden-1-ones (1-3) were synthesized for the first time from trans-1,2-bis(diazoketone)s (5, 11, and 12), respectively. The unprecedented trans-hydroindenone structure was confirmed by X-ray analysis of 3 as well as H-1 NMR analysis and was supported by ab initio molecular orbital calculations. The same reactions were also carried out under photochemical conditions and were applied to 1,3-bis(diazoketone)s, giving 2-cyclohexen-1-one derivatives.