(2S)-(1S,2R,4R)-10-(dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate | 154520-17-9

• 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: (2S)-(1S,2R,4R)-10-(dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate
• 英文别名: (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate；[(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2R)-2-cyano-2-propan-2-ylpent-4-enoate
• CAS: 154520-17-9
• 化学式: C₃₁H₅₀N₂O₄S
• 分子量: 546.815
• InChiKey: DMOHRTJXKFMUKK-GWLLCHKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  (2S)-(1S,2R,4R)-10-(dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate 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-propyl-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 (2S)-(1S,2R,4R)-10-(dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate
  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

• 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.