(1R,5R,6R)-3-Oxo-6-phenyl-2-oxa-4-aza-bicyclo[3.3.1]nonane-5-carboxylic acid methyl ester | 190074-09-0

• 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: (1R,5R,6R)-3-Oxo-6-phenyl-2-oxa-4-aza-bicyclo[3.3.1]nonane-5-carboxylic acid methyl ester
• 英文别名: methyl (1R,5R,6R)-3-oxo-6-phenyl-2-oxa-4-azabicyclo[3.3.1]nonane-5-carboxylate
• CAS: 190074-09-0
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: LOTGZTOSMSQEEV-LALPHHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,5R,6R)-3-Oxo-6-phenyl-2-oxa-4-aza-bicyclo[3.3.1]nonane-5-carboxylic acid methyl ester 在 盐酸 、 水 作用下， 反应 18.0h， 生成 (1R,3R,6R)-1-amino-3-hydroxy-6-phenylcyclohexane-1-carboxylic acid trifluoroacetate
  参考文献：
  名称：

  Synthesis of enantiomerically pure constrained γ-hydroxy-α-amino acids by directed hydroxylation

  摘要：

  Efficient synthetic routes to enantiomerically pure (1R,3R,6R)- and (1S,3S,6S)-1-amino-3-hydroxy-6-phenylcyclohexane-1-acids have been developed. The key step is a directed hydroxylation through an iodo-initiated O-functionalization reaction of methyl (1S,6R)- and (1R,6S)-1-aminocarbonyl-6-phenyl-3-cyclohexene-1-carboxylates, which can easily be obtained from the asymmetric Diels-Alder reactions of 1,3-butadiene with the (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00083-9
• 作为产物：
  描述：

  (1S,2R,5R)-1-Carbamoyl-5-hydroxy-2-phenyl-cyclohexanecarboxylic acid methyl ester 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 mercury(II) diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以92%的产率得到(1R,5R,6R)-3-Oxo-6-phenyl-2-oxa-4-aza-bicyclo[3.3.1]nonane-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of enantiomerically pure constrained γ-hydroxy-α-amino acids by directed hydroxylation

  摘要：

  Efficient synthetic routes to enantiomerically pure (1R,3R,6R)- and (1S,3S,6S)-1-amino-3-hydroxy-6-phenylcyclohexane-1-acids have been developed. The key step is a directed hydroxylation through an iodo-initiated O-functionalization reaction of methyl (1S,6R)- and (1R,6S)-1-aminocarbonyl-6-phenyl-3-cyclohexene-1-carboxylates, which can easily be obtained from the asymmetric Diels-Alder reactions of 1,3-butadiene with the (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00083-9

文献信息

• Synthesis of enantiomerically pure constrained γ-hydroxy-α-amino acids by directed hydroxylation
  作者：Alberto Avenoza、Carlos Cativiela、Miguel París、Jesús M. Peregrina、Beatriz Saenz-Torre

  DOI：10.1016/s0957-4166(97)00083-9

  日期：1997.4

  Efficient synthetic routes to enantiomerically pure (1R,3R,6R)- and (1S,3S,6S)-1-amino-3-hydroxy-6-phenylcyclohexane-1-acids have been developed. The key step is a directed hydroxylation through an iodo-initiated O-functionalization reaction of methyl (1S,6R)- and (1R,6S)-1-aminocarbonyl-6-phenyl-3-cyclohexene-1-carboxylates, which can easily be obtained from the asymmetric Diels-Alder reactions of 1,3-butadiene with the (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone, respectively. (C) 1997 Elsevier Science Ltd.