N-pentafluorophenyl-carbamic acid allyl ester | 233266-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-pentafluorophenyl-carbamic acid allyl ester
• 英文别名: prop-2-enyl N-(2,3,4,5,6-pentafluorophenyl)carbamate
• CAS: 233266-56-3
• 化学式: C₁₀H₆F₅NO₂
• 分子量: 267.155
• InChiKey: WKIGLHKQQZJUGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-pentafluorophenyl-carbamic acid allyl ester 在 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(1-naphthylmethylthio)methyl-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
• 作为产物：
  描述：

  2,3,4,5,6-五氟苯胺 、 氯甲酸烯丙酯 在 乙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以96%的产率得到N-pentafluorophenyl-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

文献信息

• Allylic protection of thiols and cysteine: II: The N-[2,3,5,6-tetrafluoro-4-(N′-piperidino)-phenyl], N-allyloxycarbonylaminomethyl (Fnam) group
  作者：Paloma Gomez-Martinez、André Malanda Kimbonguila、François Guibé

  DOI：10.1016/s0040-4020(99)00323-3

  日期：1999.5

  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.