(2R) (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyano-2,3-dimethylbutanoate | 154520-16-8

• 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-dicyclohexylsulfamoylisobornyl 2-cyano-2,3-dimethylbutanoate
• 英文别名: [(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2R)-2-cyano-2,3-dimethylbutanoate
• CAS: 154520-16-8
• 化学式: C₂₉H₄₈N₂O₄S
• 分子量: 520.777
• InChiKey: ZYGYKOBINSONOO-LKFSIGMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 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-dicyclohexylsulfamoylisobornyl 2-cyano-2,3-dimethylbutanoate 在 rhodium on alumina 甲基溴化镁 、 氢气 作用下， 以 乙醚 、 乙醇 、 氨 为溶剂， 反应 27.0h， 生成 (3R)-3-Isopropyl-3-methyl-2-azetidinone
  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
• 作为产物：
  描述：

  2-Cyano-3-methylbutanoyl chloride 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-dicyclohexylsulfamoylisobornyl 2-cyano-2,3-dimethylbutanoate
  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

• Chiral 2-cyano esters as synthetic intermediates in the synthesis of R and S α-methylvaline
  作者：Carlos Cativiela、María D. Díaz-de-Villegas、JoséA. Gálvez、Yolanda Lapeña

  DOI：10.1016/0040-4020(95)00260-f

  日期：1995.5

  A divergent stereoselective synthesis of R and S α-methylvaline from (2RS) (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyano-3-methylbutanoate has been developed.

  已开发了由（2RS）（1S，2R，4R）-10-二环己基氨磺酰基异冰片基2-氰基-3-甲基丁酸酯合成R和Sα-甲基缬氨酸的立体选择异构体。
• 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.