(2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate | 188183-29-1

• 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 3-methyl-2-cyanobutanoate
• 英文别名: (2RS) (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyano-3-methylbutanoate；(2RS)-(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyano-3-methylbutanoate；[(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-cyano-3-methylbutanoate
• CAS: 188183-29-1
• 化学式: C₂₈H₄₆N₂O₄S
• 分子量: 506.75
• InChiKey: ZGICMAWMQOWWKT-HOYHFXJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 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：

  (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate 在 rhodium on alumina 甲基溴化镁 、 氢气 、 lithium diisopropyl amide 作用下， 以 乙醚 、 乙醇 、 氨 为溶剂， 反应 28.0h， 生成 (3R)-3-Benzyl-3-isopropyl-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-methylbutanoic acid 在 silver cyanide 、 五氯化磷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate
  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。
• Stereoselective amination of chiral enolates: Synthesis of enantiomerically pure α,β-diamino acids, chiral key compounds in the synthesis of conformationally constrained peptido- and non-peptidomimetics
  作者：Ramón Badorrey、Carlos Cativiela、Maria D. Diaz-de-Villegas、JoséA. Gálvez

  DOI：10.1016/0957-4166(95)00368-y

  日期：1995.11

  This work describes an efficient synthesis of enantiomerically pure (R)-2-aminomethylalanine, (R)-2-aminomethylnorvaline, (R)-2-aminomethylvaline, (R)-2-aminomethylleucine and (R)-2-aminomethylphenylalanine by electrophilic amination of chiral 2-cyanoesters with O-(diphenylphosphinyl)hydroxylamine followed by appropiate reduction and hydrolysis.

  这项工作描述了对映体纯的（R）-2-氨基甲基丙氨酸，（R）-2-氨基甲基正缬氨酸，（R）-2-氨基甲基缬氨酸，（R）-2-氨基甲基亮氨酸和（R）-2-氨基甲基苯基丙氨酸的有效合成用O-（二苯基膦基）羟胺胺化手性2-氰基酯，然后适当还原和水解。
• A new approach to the stereoselective synthesis of conveniently protected α-allyl substituted amino acids; chiral key compounds in the synthesis of constrained peptide isostere constituents
  作者：Ramón Badorrey、Carlos Cativiela、Maria D. Díaz-de-Villegas、JoséA. Gálvez、Yolanda Lapeña

  DOI：10.1016/s0957-4166(96)00516-2

  日期：1997.1

  Enantiomerically pure alpha-allyl-N-Boc-aminoamides were prepared by Curtius rearrangement of alpha,alpha-dialkyl chiral 2-cyanoesters obtained by the diastereoselective allylation of chiral 2-cyanoesters according to a modification of our previously described procedure. (C) 1997 Elsevier Science Ltd.
• 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.