ethyl (1-chlorocyclohexyl)-azocarboxylate | 153861-63-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: ethyl (1-chlorocyclohexyl)-azocarboxylate
• 英文别名: ethyl N-(1-chlorocyclohexyl)iminocarbamate
• CAS: 153861-63-3
• 化学式: C₉H₁₅ClN₂O₂
• 分子量: 218.683
• InChiKey: BAYHFMXZMLPGIT-UHFFFAOYSA-N

物化性质

• 沸点：
  279.8±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (1-chlorocyclohexyl)-azocarboxylate 、 Acetic acid (2R,3R,4S,5R,6R)-4,5,6-triacetoxy-2-cyano-2-methylsulfanyl-tetrahydro-thiopyran-3-yl ester 在 氯化锑(V) 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 以40%的产率得到Acetic acid (2R,3R,4S,5R,6R)-4,5,6-triacetoxy-2-methylsulfanyl-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-yl)-tetrahydro-thiopyran-3-yl ester
  参考文献：
  名称：

  Novel C‐Thionucleosides: Synthesis and Reactions of 1,5‐ and 1,3‐Dialkyl Derivatives of (1,5‐Dithio‐1‐thiomethyl‐α‐D,L‐arabinopentulo‐pyranos‐1‐yl)‐1H‐1,2,4‐triazole Nucleosides

  摘要：

  A series of novel C-thionucleosides: 1,5- and 1,3-dialkyl derivatives of (2,3,4,5-tetra-O-acetyl-1,5-dithio-1-methylthio-alpha-D,L-arabinopentulopyranos-1-yl)-1H-1,2,4-triazole nucleosides 10a-d and 17a-c were synthesized, after spontaneous rearrangements, from concerted 1,3-cycloaddition of the sugar nitrile 5 with the reactive 1-(chloroalkyl)-1-aza-2-azoniaallenes 6 and 13 in the presence of a Lewis acid. Deblocking of the acylated nucleosides afforded the free nucleosides 11a-d and 18a-c. The structures of the synthesized compounds were confirmed by H-1 NMR and mass spectra.

  DOI：

  10.1081/car-120034002
• 作为产物：
  描述：

  N-(环己基氨基)氨基甲酸乙酯 在 次氯酸叔丁酯 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以96%的产率得到ethyl (1-chlorocyclohexyl)-azocarboxylate
  参考文献：
  名称：

  Synthesis of 1,2,4-triazolium salts: Reaction of 1-azo-2-azonia-allene salts with nitriles

  摘要：

  Alkyl ketone hydrazones 1 are oxidized with tert-butylhypochlorite to give geminal chloro azo compounds 2. These react with SbCl5, to give 1-aza-2-azonia-allene salts 3 as reactive intermediates which are intercepted with nitriles to yield 3H-1,2,4-triazolium salts 5. In most cases these salts rearrange spontaneously to form 1H-triazolium salts 6. Hydrolysis of 6e-g by NaOH provide bases 7a-c, which react with picric acid to give 1H-pyrazolium picrates 8.

  DOI：

  10.1007/bf00813205