(3R)-3-Benzyl-3-methyl-2-azetidinone | 144631-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R)-3-Benzyl-3-methyl-2-azetidinone
• 英文别名: (3R)-3-benzyl-3-methylazetidin-2-one
• CAS: 144631-57-2
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: GMBLYOOPBUSLMR-LLVKDONJSA-N

物化性质

• 沸点：
  341.7±11.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (E)-2-cyanocinnamate 在 palladium on activated charcoal 、 Rh/Al₂O₃ 六甲基磷酰三胺 、 甲基溴化镁 、 氢气 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 100.0h， 生成 (3R)-3-Benzyl-3-methyl-2-azetidinone
  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

• 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。
• 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.