tert-butyl (3S,4S)-3-(benzyloxy)-4-hydroxy-4-phenylpiperidine-1-carboxylate | 923948-90-7

• 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)-3-(benzyloxy)-4-hydroxy-4-phenylpiperidine-1-carboxylate
• 英文别名: tert-butyl (3S,4S)-4-hydroxy-4-phenyl-3-phenylmethoxypiperidine-1-carboxylate
• CAS: 923948-90-7
• 化学式: C₂₃H₂₉NO₄
• 分子量: 383.488
• InChiKey: YNVWIYMAIPBILX-REWPJTCUSA-N

物化性质

• 沸点：
  515.2±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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)-3-(benzyloxy)-4-hydroxy-4-phenylpiperidine-1-carboxylate 在 盐酸 、 1-甲基-1,4-环己二烯 、 20 wt% Pd(OH)2/C 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二甲基亚砜 为溶剂， 反应 73.5h， 生成 (3S,4S)-4-methoxy-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：

  溴甲苯 、 tert-butyl 3,4-dihydroxy-4-phenyl-piperidine-1-carboxylate 在 四正丁基硫酸铵 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 以97%的产率得到tert-butyl (3S,4S)-3-(benzyloxy)-4-hydroxy-4-phenylpiperidine-1-carboxylate
  参考文献：
  名称：

  WO2007/15162

  摘要：

  公开号：

文献信息

• Piperidinoyl-Pyrrolidine and Piperidinoyl-Piperidine Compounds
  申请人：Andrews Mark David

  公开号：US20080269233A1

  公开（公告）日：2008-10-30

  The present invention relates to a class of compounds of general formula (I) and the salts, hydrates, solvates, polymorphs and prodrugs wherein n, R 6 , R 7 and R 10 are as defined herein and especially to MCR4 agonist compounds of formula (I), to their use in medicine, particularly in the treatment of sexual dysfunction and obesity, to intermediates useful in their synthesis and to compositions containing them.

  本发明涉及一类通式（I）的化合物及其盐、水合物、溶剂物、多晶形和前药，其中n、R6、R7和R10如本文所定义，特别是MCR4激动剂化合物的通式（I），它们在医学上的应用，特别是在治疗性功能障碍和肥胖症方面的应用，以及有用于它们合成的中间体和含有它们的组合物。
• WO2007/15162
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.