(2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-phenyl-2-cyanopropanoate | 188183-31-5

• 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: (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-phenyl-2-cyanopropanoate
• 英文别名: (2RS)-(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 3-phenyl-2-cyanopropanoate；(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 3-phenyl-2-cyanopropanoate；(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl-2-cyano-3-phenylpropanoate；(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl-3-phenyl-2-cyanopropanoate；[(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-cyano-3-phenylpropanoate
• CAS: 188183-31-5
• 化学式: C₃₂H₄₆N₂O₄S
• 分子量: 554.794
• InChiKey: SOUKKMPJZSQELK-MLJVCPQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 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-phenyl-2-cyanopropanoate 在 六甲基磷酰三胺 、 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (R)-(-)-2-cyano-2-methyl-3-phenylpropionic acid
  参考文献：
  名称：

  对映体纯形式的（R）-和（S）-3-苄基-3-甲基-2-氮杂环丁酮的合成

  摘要：

  报道了10-二环己基氨磺酰基异冰片基-3-苯基-2-氰基丙酸酯的烯醇盐的非对映选择性甲基化。在各种条件下进行该甲基化以获得良好的产率和选择性，并且将反应产物还原并高产率地环化成相应的β-内酰胺。

  DOI：

  10.1016/s0957-4166(00)82097-2
• 作为产物：
  描述：

  (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (E)-2-cyanocinnamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-phenyl-2-cyanopropanoate
  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

• 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。
• Stereoselective amination of chiral enolates: Synthesis of chiral key intermediates for β-lactam antibiotics
  作者：Carlos Cativiela、María D. Díaz-de-Villegas、José A. Galvéz

  DOI：10.1016/0957-4166(94)80114-2

  日期：1994.8

  Stereoselective enolate trapping of lithium (1S, 2R, 4R)- 10-dicyclohexylsulfamoylisobornyl-2-cyano-3-phenylpropanoate with O-(diphenylphosphinyl) hydroxylamine followed by appropriate reduction, hydrolysis, and cyclisation processes allows the asymmetric synthesis of (S)-3-amino-3-benzyl-2-azetidinone.

  用O-（二苯基膦基）羟胺对锂（1S，2R，4R）-10-二环己基氨磺酰基异冰片基-2-氰基-3-苯基丙酸锂进行立体选择性烯醇捕获，然后进行适当的还原，水解和环化过程，可以不对称地合成（S）- 3-氨基-3-苄基-2-氮杂环丁酮。
• 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.
• 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.
• New approaches to the asymmetric synthesis of α-methylphenylalanine
  作者：Carlos Cativiela、Maria D. Diaz-de-Villegas、José A. Galvez

  DOI：10.1016/s0957-4166(00)86182-0

  日期：1994.1

  A strategy of highly selective alkylation of chiral 2-cyanoesters followed by the corresponding degradation process allows a divergent asymmetric synthesis of (R) and (S)-alpha-methylphenylalanine.