(+/-)-trans-N-allyloxycarbonyl-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine

• 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: (+/-)-trans-N-allyloxycarbonyl-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine
• 英文别名: prop-2-enyl (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate
• 化学式: C₁₆H₂₀FNO₃
• 分子量: 293.338
• InChiKey: ZCSPOTAUGLGORQ-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-N-allyloxycarbonyl-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine 在 palladium on activated charcoal Candida antarctica Lipase A 、 氢气 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 55.0h， 生成 (3S,4R)-(-)-3-acetoxymethyl-4-(4'-fluorophenyl)-N-phenyloxycarbonylpiperidine
  参考文献：
  名称：

  Enzymatic Resolution of trans-4-(4‘-Fluorophenyl)-3-hydroxymethylpiperidines, Key Intermediates in the Synthesis of (−)-Paroxetine

  摘要：

  Two Candida antarctica lipases catalyze the enantioselective acylation of N-substituted trans-4(4'-fluorophenyl)-3-hydroxymethylpiperidines in organic solvents. These two lipases show opposite stereochemical preference in these processes. Both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer, is an intermediate for the synthesis of (-)-Paroxetine.

  DOI：

  10.1021/jo010809+
• 作为产物：
  描述：

  (3S,4R)-(-)-3-acetoxymethyl-N-allyloxycarbonyl-4-(4'-fluorophenyl)piperidine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (+/-)-trans-N-allyloxycarbonyl-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine
  参考文献：
  名称：

  Enzymatic Resolution of trans-4-(4‘-Fluorophenyl)-3-hydroxymethylpiperidines, Key Intermediates in the Synthesis of (−)-Paroxetine

  摘要：

  Two Candida antarctica lipases catalyze the enantioselective acylation of N-substituted trans-4(4'-fluorophenyl)-3-hydroxymethylpiperidines in organic solvents. These two lipases show opposite stereochemical preference in these processes. Both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer, is an intermediate for the synthesis of (-)-Paroxetine.

  DOI：

  10.1021/jo010809+

文献信息

• Enzymatic Resolution of <i>trans</i>-4-(4‘-Fluorophenyl)-3-hydroxymethylpiperidines, Key Intermediates in the Synthesis of (−)-Paroxetine
  作者：Gonzalo de Gonzalo、Rosario Brieva、Víctor M. Sánchez、Miguel Bayod、Vicente Gotor

  DOI：10.1021/jo010809+

  日期：2001.12.1

  Two Candida antarctica lipases catalyze the enantioselective acylation of N-substituted trans-4(4'-fluorophenyl)-3-hydroxymethylpiperidines in organic solvents. These two lipases show opposite stereochemical preference in these processes. Both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer, is an intermediate for the synthesis of (-)-Paroxetine.