(2RS)-(1'S,2'R,4'R)-10'-(dicyclohexylsulfamoyl)isobornyl-2-cyanobutanoate | 610784-26-4

• 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)-(1'S,2'R,4'R)-10'-(dicyclohexylsulfamoyl)isobornyl-2-cyanobutanoate
• 英文别名: (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyanobutanoate；(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanobutanoate；[(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-cyanobutanoate
• CAS: 610784-26-4
• 化学式: C₂₇H₄₄N₂O₄S
• 分子量: 492.723
• InChiKey: ONGPHWQJVZLQRX-SYGZWVSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 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)-(1'S,2'R,4'R)-10'-(dicyclohexylsulfamoyl)isobornyl-2-cyanobutanoate 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 (S)-2-Cyano-2-ethyl-pentanoic acid
  参考文献：
  名称：

  脂多糖的脂肽代谢物：全合成，优选的构象和膜活性。

  摘要：

  我们已通过溶液法合成方法，并表征了从真菌Tolypocladium geodes提取的脂肽代谢物LP237-F8和五个选定的类似物，在位置8处Etn-> Aib或Etn-> Nva替代和/或三重Gln->在位置5、6和9处进行Glu（OMe）置换（Etn = Calpha-乙基降冰片碱，Aib =α-氨基异丁酸，Nva =降冰片碱）。通过FT-IR吸收，NMR和CD技术进行的构象分析强烈支持以下观点：六个末端封闭的十肽在溶液中呈高度螺旋状。螺旋形拓扑结构和两亲特性是其出色的膜活性的原因。在第8位，高疏水性和Calpha四取代的组合（如含Etn的LP237-F8代谢产物）对膜相互作用具有积极影响。

  DOI：

  10.1002/chem.200304756
• 作为产物：
  描述：

  alpha-乙基氰基乙酸 在 silver cyanide 、 五氯化磷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (2RS)-(1'S,2'R,4'R)-10'-(dicyclohexylsulfamoyl)isobornyl-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

• Synthesis of (R)- and (S)-2-amino-2-methylbutanoic acid (Iva) in enantiomerically pure form
  作者：Carlos Cativiela、Maria D. Diaz-de-Villegas、José A. Galvez

  DOI：10.1016/s0957-4166(00)80337-7

  日期：1993.7

  A new strategy for the preparation of both enantiomers of 2-amino-methylbutanoic acid (Iva) based on diastereoselective alkylation of (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanoesters and the corresponding degradation process is described.

  描述了基于（1 S，2 R，4 R）-10-二环己基氨磺酰基异冰片基2-氰基酯的非对映选择性烷基化制备2-氨基-甲基丁酸（Iva）两种对映体的新策略，以及相应的降解过程。
• Lipopeptaibol Metabolites of Tolypocladium geodes: Total Synthesis, Preferred Conformation, and Membrane Activity
  作者：Mario Rainaldi、Alessandro Moretto、Cristina Peggion、Fernando Formaggio、Stefano Mammi、Evaristo Peggion、José Antonio Galvez、Maria Dolores Díaz-de-Villegas、Carlos Cativiela、Claudio Toniolo

  DOI：10.1002/chem.200304756

  日期：2003.8.4

  (Etn=Calpha-ethylnorvaline, Aib=alpha-aminoisobutyric acid, Nva=norvaline). Conformation analysis, performed by FT-IR absorption, NMR, and CD techniques, strongly supports the view that the six terminally blocked decapeptides are highly helical in solution. Helix topology and amphiphilic character are responsible for their remarkable membrane activity. At position 8 the combination of high hydrophobicity and Calpha

  我们已通过溶液法合成方法，并表征了从真菌Tolypocladium geodes提取的脂肽代谢物LP237-F8和五个选定的类似物，在位置8处Etn-> Aib或Etn-> Nva替代和/或三重Gln->在位置5、6和9处进行Glu（OMe）置换（Etn = Calpha-乙基降冰片碱，Aib =α-氨基异丁酸，Nva =降冰片碱）。通过FT-IR吸收，NMR和CD技术进行的构象分析强烈支持以下观点：六个末端封闭的十肽在溶液中呈高度螺旋状。螺旋形拓扑结构和两亲特性是其出色的膜活性的原因。在第8位，高疏水性和Calpha四取代的组合（如含Etn的LP237-F8代谢产物）对膜相互作用具有积极影响。
• 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.