tert-butyl (3S,4S)-4-ethoxy-3-hydroxy-4-phenylpiperidine-1-carboxylate | 1278402-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (3S,4S)-4-ethoxy-3-hydroxy-4-phenylpiperidine-1-carboxylate
• CAS: 1278402-46-2
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: BAVGOVHULAZNLK-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,4S)-4-ethoxy-3-hydroxy-4-phenylpiperidine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到(3S,4S)-4-ethoxy-4-phenylpiperidin-3-ol
  参考文献：
  名称：

  A highly selective monoalkylation of tert-butyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate under phase transfer conditions

  摘要：

  Liquid-liquid phase transfer conditions have been found to provide highly selective monoalkylation of tert-butyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate, a transformation for which many other common alkylation protocols proved inadequate. The high preference for 3-O-alkylation in the phase transfer alkylation is emphasised by the absence of diether formation even in the presence of a large excess of reagents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.029
• 作为产物：
  描述：

  4-苯基-3,6-二氢-2H-吡啶-1-羧酸叔丁酯 在 1-甲基-1,4-环己二烯 、 20 wt% Pd(OH)2/C 、 四丁基硫酸氢铵 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 89.5h， 生成 tert-butyl (3S,4S)-4-ethoxy-3-hydroxy-4-phenylpiperidine-1-carboxylate
  参考文献：
  名称：

  A highly selective monoalkylation of tert-butyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate under phase transfer conditions

  摘要：

  Liquid-liquid phase transfer conditions have been found to provide highly selective monoalkylation of tert-butyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate, a transformation for which many other common alkylation protocols proved inadequate. The high preference for 3-O-alkylation in the phase transfer alkylation is emphasised by the absence of diether formation even in the presence of a large excess of reagents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.029

文献信息

• A highly selective monoalkylation of tert-butyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate under phase transfer conditions
  作者：Mark I. Lansdell、David Fradet

  DOI：10.1016/j.tetlet.2011.01.029

  日期：2011.3

  Liquid-liquid phase transfer conditions have been found to provide highly selective monoalkylation of tert-butyl 3,4-dihydroxy-4-phenylpiperidine-1-carboxylate, a transformation for which many other common alkylation protocols proved inadequate. The high preference for 3-O-alkylation in the phase transfer alkylation is emphasised by the absence of diether formation even in the presence of a large excess of reagents. (C) 2011 Elsevier Ltd. All rights reserved.