(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-benzylpentanoate | 148118-15-4

• 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: (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-benzylpentanoate
• CAS: 148118-15-4
• 化学式: C₃₅H₅₆N₂O₄S
• 分子量: 600.907
• InChiKey: RPKXZBJHJCMFPS-ZCROVJRPSA-N

物化性质

• 沸点：
  691.5±65.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  89.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-benzylpentanoate 在 甲基溴化镁 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以86%的产率得到(3R)-3-Benzyl-3-propyl-2-azetidinone
  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：

  (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-phenyl-2-cyanopropanoate 在 Rh/Al₂O₃ 六甲基磷酰三胺 、 氢气 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 25.0h， 生成 (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-benzylpentanoate
  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

• Asymmetric Synthesis of .beta.-Lactams. Highly Diastereoselective Alkylation of Chiral 2-Cyano Esters
  作者：Carlos Cativiela、Maria D. Diaz-de-Villegas、Jose A. Galvez

  DOI：10.1021/jo00088a034

  日期：1994.5

  Enolates derived from 10-(dicyclohexylsulfamoyl)isobornyl 2-substituted-2-cyanoacetates were alkylated with very good yield and high diastereoselectivity. The reduction of the resulting reaction products and subsequent cyclization of the p-amino acids led to the corresponding beta-lactam in high yields. This result paves the way for the development of a versatile and efficient asymmetric synthesis of enantiomerically pure (R)- and (S)-C(3)-disubstituted beta-lactams.