4-[2-(N,N-diphenylhydrazino)cyclopentyl]butanal | 246143-70-4

• 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: 4-[2-(N,N-diphenylhydrazino)cyclopentyl]butanal
• 英文别名: 4-[2-(2,2-diphenylhydrazinyl)cyclopentyl]butanal
• CAS: 246143-70-4
• 化学式: C₂₁H₂₆N₂O
• 分子量: 322.45
• InChiKey: ONNSRTRYFIIUPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6-三甲基苯磺酰肼 、 4-[2-(N,N-diphenylhydrazino)cyclopentyl]butanal 以 乙醇 为溶剂， 反应 1.0h， 生成 cis-4-[2-(N,N-diphenylhydrazino)cyclopentyl]butanal[N-(2,4,6-trimethylbenzenesulfonyl)hydrazone] 、 trans-4-[2-(N,N-diphenylhydrazino)cyclopentyl]butanal[N-(2,4,6-trimethylbenzenesulfonyl)hydrazone]
  参考文献：
  名称：

  Rate Constants for 5-Exo Secondary Alkyl Radical Cyclizations onto Hydrazones and Oxime Ethers via Intramolecular Competition Experiments

  摘要：

  The kinetics for the 5-exo cyclizations of secondary radicals onto various imine accepters (aryl-, alkyl-, and benzoylhydrazones, oxime ethers, etc.) have been determined. The rate constants have been established by competitive "internal radical clock" type cyclizations on the basis of the known rate constants for alkene and N,N-diphenylhydrazone systems. In refluxing benzene (80 degrees C) the rate constants for these 5-exo cyclizations fall within the range of 16 x 10(7) to 4 x 10(7) s(-1) depending on the electron-withdrawing capacity of the imine acceptor (C=NR). The fastest rate constants were observed for the N-benzyoylhydrazone acceptor (cis, 1.2 x 10(8) s(-1)), a value that is very similar to rate constant determined previously for N,N-diphenylhydrazones (cis, 1.1 x 10(8) s(-1)), These rate constants are approximately 200 times faster than those for the corresponding 5-exo cyclization onto alkenes.

  DOI：

  10.1021/jo982017u
• 作为产物：
  描述：

  2-(4-hydroxybutyl)-1-(N,N-diphenylhydrazino)cyclopentane 在 pyridine-SO3 complex 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以97%的产率得到4-[2-(N,N-diphenylhydrazino)cyclopentyl]butanal
  参考文献：
  名称：

  Rate Constants for 5-Exo Secondary Alkyl Radical Cyclizations onto Hydrazones and Oxime Ethers via Intramolecular Competition Experiments

  摘要：

  The kinetics for the 5-exo cyclizations of secondary radicals onto various imine accepters (aryl-, alkyl-, and benzoylhydrazones, oxime ethers, etc.) have been determined. The rate constants have been established by competitive "internal radical clock" type cyclizations on the basis of the known rate constants for alkene and N,N-diphenylhydrazone systems. In refluxing benzene (80 degrees C) the rate constants for these 5-exo cyclizations fall within the range of 16 x 10(7) to 4 x 10(7) s(-1) depending on the electron-withdrawing capacity of the imine acceptor (C=NR). The fastest rate constants were observed for the N-benzyoylhydrazone acceptor (cis, 1.2 x 10(8) s(-1)), a value that is very similar to rate constant determined previously for N,N-diphenylhydrazones (cis, 1.1 x 10(8) s(-1)), These rate constants are approximately 200 times faster than those for the corresponding 5-exo cyclization onto alkenes.

  DOI：

  10.1021/jo982017u