(7S)-3,6,6-trimethyl-4-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-7-yl-ammonium (2S,3S)-2,3-bis-benzoyloxy-3-carboxy-propionate | 1315509-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (7S)-3,6,6-trimethyl-4-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-7-yl-ammonium (2S,3S)-2,3-bis-benzoyloxy-3-carboxy-propionate
• CAS: 1315509-52-4
• 化学式: C₁₆H₁₉N₃O*C₁₈H₁₄O₈
• 分子量: 627.651
• InChiKey: VDMSKDDVJBVVCB-VZURBRKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  188.11
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (7S)-3,6,6-trimethyl-4-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-7-yl-ammonium (2S,3S)-2,3-bis-benzoyloxy-3-carboxy-propionate 在 potassium carbonate 作用下， 以 氯仿 、 水 为溶剂， 反应 0.5h， 以91%的产率得到(+)-(7S)-7-amino-3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-one
  参考文献：
  名称：

  Resolution, absolute configuration, and synthetic transformations of 7-amino-tetrahydroindazolones

  摘要：

  The chiral resolution of 7-amino-1-aryl-4,5,6,7-tetrahydro-indazol-4-ones was achieved via salt formation with O,O'-dibenzoyl tartaric acid. The transformation of enantiomerically enriched 7-amino-THIs into their corresponding azides proceeds with no decrease in their ee's. A comparison of the X-ray structures of the racemic and enantiopure forms of the title compounds explains the rather large melting point differences between both the series. The enantiopure azides obtained from the corresponding 7-amino-THIs were employed in copper-catalyzed Huisgen 1,3-dipolar cycloaddition reactions with various alkynes. The use of enantiomerically enriched THI scaffolds is demonstrated by the preparation of diastereomerically pure products when the former are conjugated with alkynes arising from natural sources. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.010
• 作为产物：
  描述：

  (+)-(7S)-7-amino-3,6,6-trimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-one 、 D-二苯甲酰酒石酸 以 乙醇 为溶剂， 反应 4.0h， 以3.73 g的产率得到(7S)-3,6,6-trimethyl-4-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-7-yl-ammonium (2S,3S)-2,3-bis-benzoyloxy-3-carboxy-propionate
  参考文献：
  名称：

  Resolution, absolute configuration, and synthetic transformations of 7-amino-tetrahydroindazolones

  摘要：

  The chiral resolution of 7-amino-1-aryl-4,5,6,7-tetrahydro-indazol-4-ones was achieved via salt formation with O,O'-dibenzoyl tartaric acid. The transformation of enantiomerically enriched 7-amino-THIs into their corresponding azides proceeds with no decrease in their ee's. A comparison of the X-ray structures of the racemic and enantiopure forms of the title compounds explains the rather large melting point differences between both the series. The enantiopure azides obtained from the corresponding 7-amino-THIs were employed in copper-catalyzed Huisgen 1,3-dipolar cycloaddition reactions with various alkynes. The use of enantiomerically enriched THI scaffolds is demonstrated by the preparation of diastereomerically pure products when the former are conjugated with alkynes arising from natural sources. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.010