(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[(7-methoxy-4-coumaryl)methyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[(7-methoxy-4-coumaryl)methyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• 英文别名: benzyl (3S,5S,6R)-3-[(7-methoxy-2-oxochromen-4-yl)methyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• 化学式: C₃₅H₂₉NO₇
• 分子量: 575.618
• InChiKey: AYKOLMHPBQAJSL-QPWONNCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[(7-methoxy-4-coumaryl)methyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 在 platinum(II) chloride 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 7-methoxycoumarin-4-ylalanine
  参考文献：
  名称：

  Highly enantioselective synthesis of a fluorescent amino acid

  摘要：

  A high enantiomeric excess (>99.5%) synthesis of L- 2-amino-3-(7-methoxy-4-coumaryl) propionic acid (L-Amp) is described. The two step synthesis route of this non-proteinogenic amino acid includes an oxazinone derivative as glycine enolate, which is alkylated with the fluorogenic group. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00459-6
• 作为产物：
  描述：

  4-溴甲基-7-甲氧基香豆素 、 (2R,3S)-N-苄氧羰基-2,3-二苯基吗啉-6-酮 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以40%的产率得到(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[(7-methoxy-4-coumaryl)methyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
  参考文献：
  名称：

  Highly enantioselective synthesis of a fluorescent amino acid

  摘要：

  A high enantiomeric excess (>99.5%) synthesis of L- 2-amino-3-(7-methoxy-4-coumaryl) propionic acid (L-Amp) is described. The two step synthesis route of this non-proteinogenic amino acid includes an oxazinone derivative as glycine enolate, which is alkylated with the fluorogenic group. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00459-6

文献信息

• Highly enantioselective synthesis of a fluorescent amino acid
  作者：Péter Kele、Guodong Sui、Qun Huo、Roger M. Leblanc

  DOI：10.1016/s0957-4166(00)00459-6

  日期：2000.12

  A high enantiomeric excess (>99.5%) synthesis of L- 2-amino-3-(7-methoxy-4-coumaryl) propionic acid (L-Amp) is described. The two step synthesis route of this non-proteinogenic amino acid includes an oxazinone derivative as glycine enolate, which is alkylated with the fluorogenic group. (C) 2001 Published by Elsevier Science Ltd.