N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-methylthiomethyl-carbamic acid allyl ester | 233266-59-6

• 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: N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-methylthiomethyl-carbamic acid allyl ester
• 英文别名: prop-2-enyl N-(methylsulfanylmethyl)-N-(2,3,5,6-tetrafluoro-4-piperidin-1-ylphenyl)carbamate
• CAS: 233266-59-6
• 化学式: C₁₇H₂₀F₄N₂O₂S
• 分子量: 392.418
• InChiKey: NUWROIZRXLQEEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-methylthiomethyl-carbamic acid allyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 N^α-tert-butoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester
  参考文献：
  名称：

  Allylic protection of thiols and cysteine: II: The N-[2,3,5,6-tetrafluoro-4-(N′-piperidino)-phenyl], N-allyloxycarbonylaminomethyl (Fnam) group

  摘要：

  S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)-phenyl], N-allyloxycarbonyl]-aminomethyl (Fnam) derivatives of thiols in general and cysteine in particular are readily deprotected by palladium catalysed allylic cleavage in the presence of various nucleophilic species. They are perfectly stable in both the basic conditions (piperidine/DMF) of Fmoc group removal and the acidic conditions (TFA/CH2Cl2) of t-Bu and Boc group removal. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00323-3
• 作为产物：
  描述：

  2,3,4,5,6-五氟苯胺 在 乙基氯化镁 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 99.0h， 生成 N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-methylthiomethyl-carbamic acid allyl ester
  参考文献：
  名称：

  Allylic protection of thiols and cysteine: II: The N-[2,3,5,6-tetrafluoro-4-(N′-piperidino)-phenyl], N-allyloxycarbonylaminomethyl (Fnam) group

  摘要：

  S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)-phenyl], N-allyloxycarbonyl]-aminomethyl (Fnam) derivatives of thiols in general and cysteine in particular are readily deprotected by palladium catalysed allylic cleavage in the presence of various nucleophilic species. They are perfectly stable in both the basic conditions (piperidine/DMF) of Fmoc group removal and the acidic conditions (TFA/CH2Cl2) of t-Bu and Boc group removal. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00323-3