(S)-5-(tert-butyldiphenylsilanyloxymethyl)-4-(4-fluorophenyl)-2-oxopiperidine-1-carboxylic acid benzyl ester | 1229652-81-6

• 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: (S)-5-(tert-butyldiphenylsilanyloxymethyl)-4-(4-fluorophenyl)-2-oxopiperidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(4-fluorophenyl)-2-oxopiperidine-1-carboxylate
• CAS: 1229652-81-6
• 化学式: C₃₆H₃₈FNO₄Si
• 分子量: 595.786
• InChiKey: TZFFUROBPYRYHD-ZQAZVOLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-5-(tert-butyldiphenylsilanyloxymethyl)-4-(4-fluorophenyl)-2-oxopiperidine-1-carboxylic acid benzyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以99%的产率得到(S)-[4-(4-fluorophenyl)-6-oxotetrahydropyran-3-ylmethyl]carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of (−)-Paroxetine via Enantioselective Phase-Transfer Catalytic Monoalkylation of Malonamide Ester

  摘要：

  A new enantioselective synthetic method of (-)-paroxetine is reported. (-)-Paroxetine could be obtained in 15 steps (95% ee and 9.1% overall yield) from N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester via the enantioselective phase-transfer catalytic alkylation and the diastereoselective Michael addition as the key steps.

  DOI：

  10.1021/ol100928v
• 作为产物：
  描述：

  (S)-3-(tert-butyldiphenylsilanyloxymethyl)-6-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 、 4-氟苯基溴化镁 在 copper(I) bromide dimethylsulfide complex 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到(S)-5-(tert-butyldiphenylsilanyloxymethyl)-4-(4-fluorophenyl)-2-oxopiperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of (−)-Paroxetine via Enantioselective Phase-Transfer Catalytic Monoalkylation of Malonamide Ester

  摘要：

  A new enantioselective synthetic method of (-)-paroxetine is reported. (-)-Paroxetine could be obtained in 15 steps (95% ee and 9.1% overall yield) from N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester via the enantioselective phase-transfer catalytic alkylation and the diastereoselective Michael addition as the key steps.

  DOI：

  10.1021/ol100928v

文献信息

• Synthesis of (−)-Paroxetine via Enantioselective Phase-Transfer Catalytic Monoalkylation of Malonamide Ester
  作者：Mi-hyun Kim、Yohan Park、Byeong-Seon Jeong、Hyeung-geun Park、Sang-sup Jew

  DOI：10.1021/ol100928v

  日期：2010.6.18

  A new enantioselective synthetic method of (-)-paroxetine is reported. (-)-Paroxetine could be obtained in 15 steps (95% ee and 9.1% overall yield) from N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester via the enantioselective phase-transfer catalytic alkylation and the diastereoselective Michael addition as the key steps.