(2S,6S,7R,9S)-2,7,9-triphenyl-1-aza-4,8-dioxabicyclo[4.3.0^1,6]nonan-5-one | 144896-94-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,6S,7R,9S)-2,7,9-triphenyl-1-aza-4,8-dioxabicyclo[4.3.0^1,6]nonan-5-one
• 英文别名: (1R,3S,5S,8aS)-1,3,5-triphenyl-3,5,6,8a-tetrahydro-1H-[1,3]oxazolo[4,3-c][1,4]oxazin-8-one
• CAS: 144896-94-6
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: GWKMEGVLBXNIFK-ACESQOTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,6S,7R,9S)-2,7,9-triphenyl-1-aza-4,8-dioxabicyclo[4.3.0^1,6]nonan-5-one 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 三氟乙酸 为溶剂， 以95%的产率得到(2S,3R)-3-cyclohexyl-2-(cyclohexylmethylamino)-3-hydroxypropanoic acid
  参考文献：
  名称：

  Asymmetric cycloadditions of aldehydes to stabilised azomethine ylids: Enantiocontrolled construction of β-hydroxy-α-amino acid derivatives

  摘要：

  In the absence of added dipolarophile, chiral stabilised azomethine ylids derived from the reaction of 5-(S)-phenylmorpholin-2-one (1) with aldehydes undergo efficient and highly enantiocontrolled cycloaddition with a second molecule of aldehyde to furnish products which may be converted into beta-hydroxy-alpha-amino acids.

  DOI：

  10.1016/s0957-4166(00)82093-5
• 作为产物：
  描述：

  (5S)-3,4,5,6-四氢-5-苯基-4(H)-1,4-恶嗪-2-酮 、 苯甲醛 以 甲苯 为溶剂， 以69%的产率得到(2S,6S,7R,9S)-2,7,9-triphenyl-1-aza-4,8-dioxabicyclo[4.3.0^1,6]nonan-5-one
  参考文献：
  名称：

  Asymmetric cycloadditions of aldehydes to stabilised azomethine ylids: Enantiocontrolled construction of β-hydroxy-α-amino acid derivatives

  摘要：

  In the absence of added dipolarophile, chiral stabilised azomethine ylids derived from the reaction of 5-(S)-phenylmorpholin-2-one (1) with aldehydes undergo efficient and highly enantiocontrolled cycloaddition with a second molecule of aldehyde to furnish products which may be converted into beta-hydroxy-alpha-amino acids.

  DOI：

  10.1016/s0957-4166(00)82093-5

文献信息

• Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis
  作者：David Alker、Giles Hamblett、Laurence M. Harwood、Sarah M. Robertson、David J. Watkin、C. Eleri Williams

  DOI：10.1016/s0040-4020(98)00302-0

  日期：1998.5

  Chiral stabilised azomethine ylids derived from the reaction of (5S)-5-phenylmorpholin-2-one (1) with aldehydes undergo efficient and highly diastereocontrolled cycloaddition with a second molecule of aldehyde to furnish products (2) which may be converted into enantiomerically pure three (2S,3R) beta-hydroxy-alpha-amino acids (3) in excellent yield, (C) 1998 Elsevier Science Ltd. All rights reserved.