(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate | 154520-13-5

• 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: (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate
• 英文别名: [(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2R)-2-cyano-2-methylbutanoate
• CAS: 154520-13-5
• 化学式: C₂₈H₄₆N₂O₄S
• 分子量: 506.75
• InChiKey: GCUFUSIPXPEMMC-FHMMDLEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (2R)-2-cyano-2-methylbutanoic acid
  参考文献：
  名称：

  对映体纯形式的（R）-和（S）-2-氨基-2-甲基丁酸（Iva）的合成

  摘要：

  描述了基于（1 S，2 R，4 R）-10-二环己基氨磺酰基异冰片基2-氰基酯的非对映选择性烷基化制备2-氨基-甲基丁酸（Iva）两种对映体的新策略，以及相应的降解过程。

  DOI：

  10.1016/s0957-4166(00)80337-7
• 作为产物：
  描述：

  2-氰基丁酰氯 在 silver cyanide 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methylbutanoate
  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

• 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.
• Synthesis of (R)- and (S)-2-amino-2-methylbutanoic acid (Iva) in enantiomerically pure form
  作者：Carlos Cativiela、Maria D. Diaz-de-Villegas、José A. Galvez

  DOI：10.1016/s0957-4166(00)80337-7

  日期：1993.7

  A new strategy for the preparation of both enantiomers of 2-amino-methylbutanoic acid (Iva) based on diastereoselective alkylation of (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanoesters and the corresponding degradation process is described.

  描述了基于（1 S，2 R，4 R）-10-二环己基氨磺酰基异冰片基2-氰基酯的非对映选择性烷基化制备2-氨基-甲基丁酸（Iva）两种对映体的新策略，以及相应的降解过程。