(3S,7aR)-7a-Methyl-5-oxo-3-phenyl-2,3,5,7a-tetrahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester | 141708-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,7aR)-7a-Methyl-5-oxo-3-phenyl-2,3,5,7a-tetrahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester
• 英文别名: benzyl (3S,7aR)-7a-methyl-5-oxo-3-phenyl-2,3-dihydropyrrolo[2,1-b][1,3]oxazole-6-carboxylate
• CAS: 141708-08-9
• 化学式: C₂₁H₁₉NO₄
• 分子量: 349.386
• InChiKey: LHYSQSUXIXFCPH-WIYYLYMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,7aR)-7a-Methyl-5-oxo-3-phenyl-2,3,5,7a-tetrahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester 在 palladium on activated charcoal aluminium hydride 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 28.83h， 生成 (2S,3R)-3-Butyl-2-methyl-pyrrolidine
  参考文献：
  名称：

  Asymmetric conjugate additions to chiral bicyclic lactams. Synthesis of aracemic trans-2,3-disubstituted pyrrolidines

  摘要：

  The trans-2,3-disubstituted pyrrolidine moiety, found in the pyrrolizidine alkaloids as well as other natural products, has been accessed from the alpha,beta-unsaturated bicyclic lactams 1d and 10. Conjugate addition of lower order cyanocuprates to lactams 1d and 10 resulted in endo entry of the cuprate with high diastereoselectivity. Other cuprates were investigated and resulted in diminished or opposite stereoselectivities. Further transformation of the beta-substituted lactams provided the title compounds in good overall yield and high enantiomeric excess.

  DOI：

  10.1021/jo00040a018
• 作为产物：
  描述：

  氯甲酸苄酯 、 (3S,7aR)-7a-methyl-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one 生成 (3S,7aR)-7a-Methyl-5-oxo-3-phenyl-2,3,5,7a-tetrahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester
  参考文献：
  名称：

  Asymmetric conjugate additions to chiral bicyclic lactams. Synthesis of aracemic trans-2,3-disubstituted pyrrolidines

  摘要：

  The trans-2,3-disubstituted pyrrolidine moiety, found in the pyrrolizidine alkaloids as well as other natural products, has been accessed from the alpha,beta-unsaturated bicyclic lactams 1d and 10. Conjugate addition of lower order cyanocuprates to lactams 1d and 10 resulted in endo entry of the cuprate with high diastereoselectivity. Other cuprates were investigated and resulted in diminished or opposite stereoselectivities. Further transformation of the beta-substituted lactams provided the title compounds in good overall yield and high enantiomeric excess.

  DOI：

  10.1021/jo00040a018

文献信息

• Non-metallocatalyzed epoxidation of chiral unsaturated lactams by tertiary amine N-oxides
  作者：C.J. Andres、N. Spetseris、J.R. Norton、A.I. Meyers

  DOI：10.1016/0040-4039(95)00114-r

  日期：1995.3

  Tertiary amine N-oxides were used to stereospecifically epoxidize chiral unsaturated bicyclic lactams in high yields (90–99%) at room temperature. This appears to be the first reported example of tertiary amine N-oxides acting as epoxidizing agents in the absence of a metal catalyst.

  叔胺N-氧化物用于在室温下以高产率（90-99％）立体定向环氧化手性不饱和双环内酰胺。这似乎是在没有金属催化剂的情况下叔胺N-氧化物起环氧化剂作用的第一个报道实例。
• [2 + 2] and [3 + 2] Cycloadditions of Triisopropylallylsilane to .alpha.,.beta.-Unsaturated Bicyclic Lactams
  作者：Gregory P. Brengel、C. Rithner、A. I. Meyers

  DOI：10.1021/jo00097a013

  日期：1994.9

  Addition of allylsilane gave cyclobutanes at low temperature and cyclopentanes at higher temperature.
• Allyldimethyltritylsilane: construction of enantiomerically pure cyclobutano[c]fused pyrrolidines
  作者：Michael D Groaning、Gregory P Brengel、A.I Meyers

  DOI：10.1016/s0040-4020(01)00083-7

  日期：2001.3

  Cyclobutannulation of the bicyclic lactam with allyldimethyltritylsilane is accomplished in high yield with good diastereoselectivity. The resulting tricyclic system is converted to a enantiomerically pure cyclobutane-fused pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Brengel Gregory P., Rithner C., Meyers A. I., J. Org. Chem, 59 (1994) N 18, S 5144-5146
  作者：Brengel Gregory P., Rithner C., Meyers A. I.

  DOI：——

  日期：——
• Asymmetric conjugate additions to chiral bicyclic lactams. Synthesis of aracemic trans-2,3-disubstituted pyrrolidines
  作者：A. I. Meyers、Lawrence Snyder

  DOI：10.1021/jo00040a018

  日期：1992.7

  The trans-2,3-disubstituted pyrrolidine moiety, found in the pyrrolizidine alkaloids as well as other natural products, has been accessed from the alpha,beta-unsaturated bicyclic lactams 1d and 10. Conjugate addition of lower order cyanocuprates to lactams 1d and 10 resulted in endo entry of the cuprate with high diastereoselectivity. Other cuprates were investigated and resulted in diminished or opposite stereoselectivities. Further transformation of the beta-substituted lactams provided the title compounds in good overall yield and high enantiomeric excess.