N-[3-(3-chlorophenyl)-1-cyclohexyl-4-cyclohexyliminoazetidin-2-ylidene]-4-methylbenzenesulfonamide | 1359876-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: N-[3-(3-chlorophenyl)-1-cyclohexyl-4-cyclohexyliminoazetidin-2-ylidene]-4-methylbenzenesulfonamide
• CAS: 1359876-05-3
• 化学式: C₂₈H₃₄ClN₃O₂S
• 分子量: 512.116
• InChiKey: CZKGGNYXAQBJKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[3-(3-chlorophenyl)-1-cyclohexyl-4-cyclohexyliminoazetidin-2-ylidene]-4-methylbenzenesulfonamide 在 lithium hexamethyldisilazane 、 水 作用下， 以 四氢呋喃 、 乙基苯 为溶剂， 反应 4.0h， 以98%的产率得到N-[3-(3-chlorophenyl)-5-cyclohexyl-1,5-diazaspiro[5.5]undeca-1,3-dien-2-yl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Regioselective Ring Expansion of 2,4-Diiminoazetidines via Cleavage of C–N and C(sp³)–H Bonds: Efficient Construction of 2,3-Dihydropyrimidinesulfonamides

  摘要：

  A highly regioselective base-mediated ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp(3))-H bonds is achieved for the first time to afford efficiently 2,3-dihydropyrimidinesulfonamides. The mechanism of the ring expansion via tandem 4 pi electrocyclic ring-opening/1,5-H shift/6 pi electrocydic ring-closing is well confirmed by the trapping experiments of two key intermediates and deuterium labeling studies.

  DOI：

  10.1021/ja211486f
• 作为产物：
  描述：

  对甲苯磺酰叠氮 、 3-氯苯乙炔 、 N,N'-二环己基碳二亚胺 在 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以83%的产率得到N-[3-(3-chlorophenyl)-1-cyclohexyl-4-cyclohexyliminoazetidin-2-ylidene]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Regioselective Ring Expansion of 2,4-Diiminoazetidines via Cleavage of C–N and C(sp³)–H Bonds: Efficient Construction of 2,3-Dihydropyrimidinesulfonamides

  摘要：

  A highly regioselective base-mediated ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp(3))-H bonds is achieved for the first time to afford efficiently 2,3-dihydropyrimidinesulfonamides. The mechanism of the ring expansion via tandem 4 pi electrocyclic ring-opening/1,5-H shift/6 pi electrocydic ring-closing is well confirmed by the trapping experiments of two key intermediates and deuterium labeling studies.

  DOI：

  10.1021/ja211486f

文献信息

• Regioselective Ring Expansion of 2,4-Diiminoazetidines via Cleavage of C–N and C(sp³)–H Bonds: Efficient Construction of 2,3-Dihydropyrimidinesulfonamides
  作者：Yang Wang、Yue Chi、Wen-Xiong Zhang、Zhenfeng Xi

  DOI：10.1021/ja211486f

  日期：2012.2.15

  A highly regioselective base-mediated ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp(3))-H bonds is achieved for the first time to afford efficiently 2,3-dihydropyrimidinesulfonamides. The mechanism of the ring expansion via tandem 4 pi electrocyclic ring-opening/1,5-H shift/6 pi electrocydic ring-closing is well confirmed by the trapping experiments of two key intermediates and deuterium labeling studies.