(2R,3R)-3-diphenylmethylamino-3-(1-naphthyl)-1,2-propanediol | 192125-30-7

• 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: (2R,3R)-3-diphenylmethylamino-3-(1-naphthyl)-1,2-propanediol
• 英文别名: (2R,3R)-3-(benzhydrylamino)-3-naphthalen-1-ylpropane-1,2-diol
• CAS: 192125-30-7
• 化学式: C₂₆H₂₅NO₂
• 分子量: 383.49
• InChiKey: PCJWICCZKBKCCJ-AZGAKELHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (2R,3R)-3-diphenylmethylamino-3-(1-naphthyl)-1,2-propanediol 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 48.0h， 以87%的产率得到(2R,3R)-3-(tert-butoxycarbonylamino)-3-(1-naphthyl)-1,2-propanediol
  参考文献：
  名称：

  Enantioselective synthesis of N-Boc-1-naphthylglycine

  摘要：

  A new stereoselective synthesis of enantiomerically pure 1-naphthylglycine has been developed. The source of chirality is the catalytic Sharpless epoxidation. Regioselective and stereospecific ring-opening of the corresponding epoxy alcohol is performed either with sodium azide or with benzhydrylamine as ammonia synthetic equivalents. Subsequent hydrogenation in the presence of (Boc)(2)O affords crystalline N-Boc-3-(1-naphthyl)propane-1,2-diol which is enantiomerically enriched up to 100% ee and oxidized to the alpha-amino acid. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00137-7
• 作为产物：
  描述：

  (E)-3-(1-naphthyl)prop-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 4 A molecular sieve 作用下， 以 异辛烷 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (2R,3R)-3-diphenylmethylamino-3-(1-naphthyl)-1,2-propanediol
  参考文献：
  名称：

  Enantioselective synthesis of N-Boc-1-naphthylglycine

  摘要：

  A new stereoselective synthesis of enantiomerically pure 1-naphthylglycine has been developed. The source of chirality is the catalytic Sharpless epoxidation. Regioselective and stereospecific ring-opening of the corresponding epoxy alcohol is performed either with sodium azide or with benzhydrylamine as ammonia synthetic equivalents. Subsequent hydrogenation in the presence of (Boc)(2)O affords crystalline N-Boc-3-(1-naphthyl)propane-1,2-diol which is enantiomerically enriched up to 100% ee and oxidized to the alpha-amino acid. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00137-7

文献信息

• Enantioselective synthesis of N-Boc-1-naphthylglycine
  作者：Eva Medina、Anton Vidal-Ferran、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1016/s0957-4166(97)00137-7

  日期：1997.5

  A new stereoselective synthesis of enantiomerically pure 1-naphthylglycine has been developed. The source of chirality is the catalytic Sharpless epoxidation. Regioselective and stereospecific ring-opening of the corresponding epoxy alcohol is performed either with sodium azide or with benzhydrylamine as ammonia synthetic equivalents. Subsequent hydrogenation in the presence of (Boc)(2)O affords crystalline N-Boc-3-(1-naphthyl)propane-1,2-diol which is enantiomerically enriched up to 100% ee and oxidized to the alpha-amino acid. (C) 1997 Elsevier Science Ltd.