(3R,7aS)-6-Benzoyl-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,7aS)-6-Benzoyl-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one
• 英文别名: (3R,7aS)-6-benzoyl-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-one
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: AMPMVHBZCCVDCX-SCVGIUIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲酸甲酯 、 (+)-(3R,7aS)-四氢-3-苯基-3H,5H-吡咯并[1,2-c]噁唑-5-酮 在 sodium hydride 作用下， 以 甲苯 为溶剂， 以83%的产率得到(3R,7aS)-6-Benzoyl-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one
  参考文献：
  名称：

  A concise approach to functionalised, homochiral pyrrolidinones

  摘要：

  Acylation of O,N-acetal 1 gives excellent yields of the C-7 substituted products 2a,b. Alkylation of 2a under mild conditions gives high yields of the exo- 3 and endo- 4 substituted products in varying ratios, depending on the alkylating agent. The unsaturated derivative 8 reacts in high yields under mild conditions with dienes and 1,3-dipoles to give the corresponding cycloadducts. Elaboration of these compounds by acidic deprotection to substituted pyroglutaminols, and oxidation to the corresponding pyroglutamates, can be readily achieved.

  DOI：

  10.1016/0957-4166(95)00007-c

文献信息

• A concise approach to functionalised, homochiral pyrrolidinones
  作者：Mark J Bamford、Mark Beard、David T Cherry、Mark G Moloney

  DOI：10.1016/0957-4166(95)00007-c

  日期：1995.2

  Acylation of O,N-acetal 1 gives excellent yields of the C-7 substituted products 2a,b. Alkylation of 2a under mild conditions gives high yields of the exo- 3 and endo- 4 substituted products in varying ratios, depending on the alkylating agent. The unsaturated derivative 8 reacts in high yields under mild conditions with dienes and 1,3-dipoles to give the corresponding cycloadducts. Elaboration of these compounds by acidic deprotection to substituted pyroglutaminols, and oxidation to the corresponding pyroglutamates, can be readily achieved.