(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (R)-3-phenyl-2-allyl-2-cyanopropanoate | 143100-10-1

• 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: (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (R)-3-phenyl-2-allyl-2-cyanopropanoate
• 英文别名: (2S)-(1S,2R,4R)-10-(dicyclohexylsulfamoyl)isobornyl 2-benzyl-2-cyano-4-pentenoate；(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-benzyl-2-cyano-4-pentenoate；[(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2R)-2-benzyl-2-cyanopent-4-enoate
• CAS: 143100-10-1
• 化学式: C₃₅H₅₀N₂O₄S
• 分子量: 594.859
• InChiKey: FFTBBKVNSXATJV-ZCROVJRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (R)-3-phenyl-2-allyl-2-cyanopropanoate 在 甲醇 、 氢氧化钾 、 氯化亚砜 、 sodium azide 作用下， 以 丙酮 为溶剂， 反应 7.0h， 生成 (R)-2-Benzyl-2-cyano-pent-4-enoyl azide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(96)00516-2
• 作为产物：
  描述：

  (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-phenyl-2-cyanopropanoate 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以65%的产率得到(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (R)-3-phenyl-2-allyl-2-cyanopropanoate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(96)00516-2

文献信息

• Chiral 2-Cyanocinnamates in Conjugate Addition Asymmetric Enolate Trapping Reactions
  作者：Carlos Cativiela、Maria Dolores Diaz-De-Villegas、José Antonio Galvez

  DOI：10.1246/bcsj.65.1657

  日期：1992.6

  Chiral 2-cyanocinnamates react with L-selectride® to give an intermediate enolate which can be stereoselectively trapped with different halides to afford α-substituted phenylalanine precursors with excellent chemical yields and good diastereomeric excess.

  手性 2-氰基肉桂酸酯与 L-selectride® 反应生成中间体烯醇化物，该中间体可以被不同的卤化物立体选择性地捕获，以提供具有优异化学产率和良好非对映体过量的 α-取代苯丙氨酸前体。
• 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.
• 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.