(2S)-2-Azido-3,3-diphenyl-1-butanol | 169768-99-4

• 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: (2S)-2-Azido-3,3-diphenyl-1-butanol
• CAS: 169768-99-4
• 化学式: C₁₆H₁₇N₃O
• 分子量: 267.33
• InChiKey: XCEYLNSCZHHDOH-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-Azido-3,3-diphenyl-1-butanol 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以77%的产率得到(S)-(Diphenylmethyl)alaninol
  参考文献：
  名称：

  Preparation of Chiral Bisoxazolines: Observations on the Effect of Substituents

  摘要：

  A series of enantiomerically pure 4-substituted bisoxazolines 1a-f, 2c, and 2e was prepared from naturally derived or synthetic amino alcohols and malonyl dichloride derivatives. The formation of the bisoxazolines was accomplished in two stages: (1) preparation of the bis-amides of the malonyl derivatives with the amino alcohols and (2) cyclization of the hydroxy amides 4 by either of two general protocols; (1) heating with thionyl chloride in toluene or (2) formation of the bismesylate and then heating with aqueous or alcoholic base. The latter procedure was found to be more reliable especially for bisoxazolines with bulky substitutents at C(4). The C(4) trityl-substituted hydroxy amide 4f produced the bis(acylaziridine) 10 by cyclization on the nitrogen atom using KOH/MeOH, but afforded the desired bisoxazoline If by the action of SOCl2/Et(3)N. The synthesis of the nonnaturally derived amino alcohols using the Evans asymmetric azidation procedure is also described.

  DOI：

  10.1021/jo00120a036
• 作为产物：
  描述：

  在 锂硼氢 、 正丁基锂 、 2,4,6-三异丙基苯磺酰叠氮化物 、 水 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 3.03h， 生成 (2S)-2-Azido-3,3-diphenyl-1-butanol
  参考文献：
  名称：

  Preparation of Chiral Bisoxazolines: Observations on the Effect of Substituents

  摘要：

  A series of enantiomerically pure 4-substituted bisoxazolines 1a-f, 2c, and 2e was prepared from naturally derived or synthetic amino alcohols and malonyl dichloride derivatives. The formation of the bisoxazolines was accomplished in two stages: (1) preparation of the bis-amides of the malonyl derivatives with the amino alcohols and (2) cyclization of the hydroxy amides 4 by either of two general protocols; (1) heating with thionyl chloride in toluene or (2) formation of the bismesylate and then heating with aqueous or alcoholic base. The latter procedure was found to be more reliable especially for bisoxazolines with bulky substitutents at C(4). The C(4) trityl-substituted hydroxy amide 4f produced the bis(acylaziridine) 10 by cyclization on the nitrogen atom using KOH/MeOH, but afforded the desired bisoxazoline If by the action of SOCl2/Et(3)N. The synthesis of the nonnaturally derived amino alcohols using the Evans asymmetric azidation procedure is also described.

  DOI：

  10.1021/jo00120a036