(2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate | 143100-05-4

• 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: (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate
• 英文别名: (2S)-(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyano-2-methyl-3-phenylpropanoate；(2S)-(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl-2-methyl-3-phenyl-2-cyanopropanoate；(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (S)-3-phenyl-2-methyl-2-cyanopropanoate；[(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2S)-2-cyano-2-methyl-3-phenylpropanoate
• CAS: 143100-05-4
• 化学式: C₃₃H₄₈N₂O₄S
• 分子量: 568.821
• InChiKey: NQRSPHFZJMMDHS-HLNZXYRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 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-methyl-3-phenylpropanoate 在 氢氧化钾 、 sodium azide 、 五氯化磷 作用下， 以 甲醇 、 乙醚 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 (2S)-2-cyano-2-methyl-3-phenylpropanoyl azide
  参考文献：
  名称：

  New approaches to the asymmetric synthesis of α-methylphenylalanine

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)86182-0
• 作为产物：
  描述：

  (-)-10-dicyclohexylsulfamoyl-D-isoborneol 在 六甲基磷酰三胺 、 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-methyl-3-phenylpropanoate
  参考文献：
  名称：

  New approaches to the asymmetric synthesis of α-methylphenylalanine

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)86182-0

文献信息

• Synthesis of (R)- and (S)-3-benzyl-3-methyl-2-azetidinone in enantiomerically pure form
  作者：Carlos Cativiela、Maria D. Diaz-de-Villegas、Joé A. Galvez

  DOI：10.1016/s0957-4166(00)82097-2

  日期：1992.9

  The diastereoselective methylation of the enolate of 10-dicyclohexylsulfamoylisobornyl-3-phenyl-2-cyanopropanoate is reported. This methylation was carried out under a variety of conditions to achieve a good yield and selectivity and the reaction product was reduced and cyclised to the corresponding β-lactam in high yield.

  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。
• 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.
• 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.