Adamantane-1-carboxylic acid {(R)-1-[2-(2-oxo-2-phenyl-ethanesulfonyl)-phenyl]-ethyl}-amide | 183204-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Adamantane-1-carboxylic acid {(R)-1-[2-(2-oxo-2-phenyl-ethanesulfonyl)-phenyl]-ethyl}-amide
• 英文别名: N-[(1R)-1-(2-phenacylsulfonylphenyl)ethyl]adamantane-1-carboxamide
• CAS: 183204-13-9
• 化学式: C₂₇H₃₁NO₄S
• 分子量: 465.613
• InChiKey: FJNYSWLKEZKCMP-FVFHPELPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Adamantane-1-carboxylic acid {(R)-1-[2-(2-oxo-2-phenyl-ethanesulfonyl)-phenyl]-ethyl}-amide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 Adamantane-1-carboxylic acid {(R)-1-[2-(2-hydroxy-2-phenyl-ethanesulfonyl)-phenyl]-ethyl}-amide
  参考文献：
  名称：

  Asymmetric synthesis of β-hydroxy sulfones by reduction of chiral β-keto sulfones

  摘要：

  Chiral beta-keto sulfones 3 have been prepared from enantiomerically pure sulfinic acids 2 derived from (R)- and S-methylbenzylamine. Enantiospecific reduction of these ketosulfones 3 can be achieved using different hydrides affording beta-hydroxy sulfones. Opposite configurations on the newly created stereocenter is obtained with DIBAL-H or LAH as reducing agents. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00310-2
• 作为产物：
  描述：

  2-溴苯乙酮 、 在 氢氧化钾 作用下， 生成 Adamantane-1-carboxylic acid {(R)-1-[2-(2-oxo-2-phenyl-ethanesulfonyl)-phenyl]-ethyl}-amide
  参考文献：
  名称：

  Asymmetric synthesis of β-hydroxy sulfones by reduction of chiral β-keto sulfones

  摘要：

  Chiral beta-keto sulfones 3 have been prepared from enantiomerically pure sulfinic acids 2 derived from (R)- and S-methylbenzylamine. Enantiospecific reduction of these ketosulfones 3 can be achieved using different hydrides affording beta-hydroxy sulfones. Opposite configurations on the newly created stereocenter is obtained with DIBAL-H or LAH as reducing agents. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00310-2