(R)-2-Aminomethyl-2-benzyl-5-phenyl-pentanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester | 148118-18-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-Aminomethyl-2-benzyl-5-phenyl-pentanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• 英文别名: [(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2R)-2-(aminomethyl)-2-benzyl-5-phenylpentanoate
• CAS: 148118-18-7
• 化学式: C₄₁H₆₀N₂O₄S
• 分子量: 677.004
• InChiKey: CKIMXSGPRHBVOZ-VNPXKJLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2-Aminomethyl-2-benzyl-5-phenyl-pentanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 甲基溴化镁 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以91%的产率得到(R)-3-Benzyl-3-(3-phenyl-propyl)-azetidin-2-one
  参考文献：
  名称：

  Synthesis of (R)- 3-alkyl-3-benzyl-2-azetidinones in enantiomerically pure form

  摘要：

  The diastereoselective alkylation of the enolate of 10-dicyclohexylsulfamoylisobornyl 3-phenyl-2-cyanopropanoate is reported. This alkylation took place with very good yield and selectivity and the reaction product was reduced and cyclised to the corresponding beta-lactam in high yield.

  DOI：

  10.1016/s0957-4166(00)82343-5
• 作为产物：
  描述：

  (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (E)-2-cyanocinnamate 在 palladium on activated charcoal 、 Rh/Al₂O₃ 六甲基磷酰三胺 、 氢气 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 97.0h， 生成 (R)-2-Aminomethyl-2-benzyl-5-phenyl-pentanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  Synthesis of (R)- 3-alkyl-3-benzyl-2-azetidinones in enantiomerically pure form

  摘要：

  The diastereoselective alkylation of the enolate of 10-dicyclohexylsulfamoylisobornyl 3-phenyl-2-cyanopropanoate is reported. This alkylation took place with very good yield and selectivity and the reaction product was reduced and cyclised to the corresponding beta-lactam in high yield.

  DOI：

  10.1016/s0957-4166(00)82343-5

文献信息

• Synthesis of (R)- 3-alkyl-3-benzyl-2-azetidinones in enantiomerically pure form
  作者：Carlos Cativiela、Maria D. Diaz-de-Villegas、José A. Galvez

  DOI：10.1016/s0957-4166(00)82343-5

  日期：1993.2

  The diastereoselective alkylation of the enolate of 10-dicyclohexylsulfamoylisobornyl 3-phenyl-2-cyanopropanoate is reported. This alkylation took place with very good yield and selectivity and the reaction product was reduced and cyclised to the corresponding beta-lactam in high yield.