(S_S,1S,2S,5R,E)-N-(4-nitrobenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide | 1366005-24-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S_S,1S,2S,5R,E)-N-(4-nitrobenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide
• 英文别名: (S,1S,2S,5R,E)-2-isopropyl-5-methyl-N-(4-nitrobenzylidene)cyclohexanesulfinamide；(S,1s,2s,5r,e)-2-isopropyl-5-methyl-N-(4-nitro-benzylidene)cyclohexanesulfinamide；(NE,S,1S,2S,5R)-5-methyl-N-[(4-nitrophenyl)methylidene]-2-propan-2-ylcyclohexane-1-sulfinamide
• CAS: 1366005-24-4
• 化学式: C₁₇H₂₄N₂O₃S
• 分子量: 336.455
• InChiKey: YBBDKLOKRZNZHN-VZZKHWCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  94.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S_S,1S,2S,5R,E)-N-(4-nitrobenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到(S,1S,2S,5R)-N-(4-nitrobenzyl)-2-isopropyl-5-methylcyclohexanesulfinamide
  参考文献：
  名称：

  Asymmetric synthesis of new optically active sulfinamides of menthane series and their derivatives

  摘要：

  Asymmetric syntheses were performed of neomenthanesulfinamide in the yield of 60% and de 74%, of neomenthanesulfinaldimines and N-substituted neomenthanesulfinamides in 22-80 and 40-90% yields respectively.

  DOI：

  10.1134/s1070428012020066
• 作为产物：
  描述：

  (1S,2S,5R)-2-isopropyl-5-methylcyclohexanesulfinamide 、 对硝基苯甲醛 在 对甲苯磺酸 、 copper(II) sulfate 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(S_S,1S,2S,5R,E)-N-(4-nitrobenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide
  参考文献：
  名称：

  Asymmetric synthesis of new optically active sulfinamides of menthane series and their derivatives

  摘要：

  Asymmetric syntheses were performed of neomenthanesulfinamide in the yield of 60% and de 74%, of neomenthanesulfinaldimines and N-substituted neomenthanesulfinamides in 22-80 and 40-90% yields respectively.

  DOI：

  10.1134/s1070428012020066

文献信息

• New N-substituted sulfinamides of neomenthane series
  作者：E. S. Izmest’ev、D. V. Sudarikov、S. A. Rubtsova、P. A. Slepukhin、A. V. Kutchin

  DOI：10.1007/s11172-013-0343-3

  日期：2013.11

  A reaction of neomenthanethiol with ammonia and N-chlorosuccinimide with subsequent addition of aromatic aldehydes leads to chiral N-arylideneneomenthylsulfenimines, whose oxidation at the sulfur atom gives N-arylideneneomenthylsulfinimines. The reactions of N-arylideneneomenthylsulfinimines with lithium aluminum hydride or Grignard reagents proceed at the imine fragment and lead to the corresponding

  新薄荷硫醇与氨和 N-氯代琥珀酰亚胺与随后加入芳香醛的反应产生手性 N-亚芳基薄荷基亚磺亚胺，其在硫原子处氧化产生 N-亚芳基亚甲基亚磺亚胺。N-亚芳基新薄荷亚磺亚胺与氢化铝锂或格氏试剂的反应在亚胺片段处进行并产生相应的 N-苄基新薄荷亚磺酰胺。