(2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-phenyl-2-cyanoacetate

• 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: (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-phenyl-2-cyanoacetate
• 英文别名: (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (2RS)-2-phenylcyanoacetate；[(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-cyano-2-phenylacetate
• 化学式: C₃₁H₄₄N₂O₄S
• 分子量: 540.767
• InChiKey: ALEWLPJALAUVHB-FMHFGWIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-phenyl-2-cyanoacetate 在 palladium on activated charcoal 六甲基磷酰三胺 、 氢气 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (2R)-2-phenyl-2-cyanopentanoate
  参考文献：
  名称：

  Cativiela, Carlos; Villegas, Maria D. Diaz de; Galvez, Jose A., Anales de Quimica, 1994, vol. 90, # 7-8, p. 432 - 437

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-cyano-2-phenylacetate 、 (-)-10-dicyclohexylsulfamoyl-D-isoborneol 在 三甲基铝 作用下， 以 正己烷 、 甲苯 为溶剂， 以93%的产率得到(2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-phenyl-2-cyanoacetate
  参考文献：
  名称：

  Asymmetric Synthesis of .beta.-Lactams. Highly Diastereoselective Alkylation of Chiral 2-Cyano Esters

  摘要：

  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.

  DOI：

  10.1021/jo00088a034

文献信息

• Cativiela, Carlos; Villegas, Maria D. Diaz de; Galvez, Jose A., Anales de Quimica, 1994, vol. 90, # 7-8, p. 432 - 437
  作者：Cativiela, Carlos、Villegas, Maria D. Diaz de、Galvez, Jose A.、Lapena, Yolanda

  DOI：——

  日期：——
• 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.