N,N-diethyl-2-fluoro-2-trifluoromethyl-4-hexenamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N-diethyl-2-fluoro-2-trifluoromethyl-4-hexenamide
• 英文别名: (E)-N,N-diethyl-2-fluoro-2-(trifluoromethyl)hex-4-enamide
• 化学式: C₁₁H₁₇F₄NO
• 分子量: 255.256
• InChiKey: ATYGOHSIDHUIDD-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2-fluoro-2-trifluoromethyl-4-hexenamide 在 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 (3S,5R)-3-Fluoro-5-(1-iodo-ethyl)-3-trifluoromethyl-dihydro-furan-2-one 、 (3S,5S)-3-Fluoro-5-(1-iodo-ethyl)-3-trifluoromethyl-dihydro-furan-2-one
  参考文献：
  名称：

  A novel reaction of allylic alcohols with hexafluoropropene-diethylamine adduct (PPDA) to form 2-fluoro-2-trifluoromethyl-4-alkenamide

  摘要：

  Treatment of allylic alcohols with hexafluoropropene-diethylamine adduct (PPDA) afforded N,N-diethyl-2-fluoro-2-trifluoromethyl-4-alkenamides which were formed by the Claisen rearrangement of intermediary 2-alkenyl-1-diethylamino-2,3,3,3-tetrafluoro-1-propenyl ethers. Although (E)-allylic alcohols gave two diastereomeric products in about 1:1 ratio, (Z)-allylic alcohols gave the corresponding product as a single diastereomer. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00191-x
• 作为产物：
  描述：

  3-丁烯-2-醇 、 N,N-二乙基-1,1,2,3,3,3-六氟丙胺 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 25.0h， 以79%的产率得到N,N-diethyl-2-fluoro-2-trifluoromethyl-4-hexenamide
  参考文献：
  名称：

  A novel reaction of allylic alcohols with hexafluoropropene-diethylamine adduct (PPDA) to form 2-fluoro-2-trifluoromethyl-4-alkenamide

  摘要：

  Treatment of allylic alcohols with hexafluoropropene-diethylamine adduct (PPDA) afforded N,N-diethyl-2-fluoro-2-trifluoromethyl-4-alkenamides which were formed by the Claisen rearrangement of intermediary 2-alkenyl-1-diethylamino-2,3,3,3-tetrafluoro-1-propenyl ethers. Although (E)-allylic alcohols gave two diastereomeric products in about 1:1 ratio, (Z)-allylic alcohols gave the corresponding product as a single diastereomer. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00191-x

文献信息

• Novel reaction of allylic alcohols with a hexafluoropropene-diethylamine adduct (PPDA) to form α-fluoro-α-(trifluoromethyl)-γ,δ-unsaturated amides
  作者：Ken-ichi Ogu、Motohiro Akazome、Katsuyuki Ogura

  DOI：10.1016/s0040-4039(97)10548-2

  日期：1998.1

  Treatment of allylic alcohols (1) with a hexafluoropropene-diethylamine adduct (PPDA) gave alpha-fluoro-(trifluoromethyl)-gamma,delta-unsaturated amides (2), which were shown to be important precursors for synthesizing a variety of fluoro(trifluoromethyl)methylene-containing compounds. (C) 1997 Elsevier Science Ltd. All rights reserved.
• A novel reaction of allylic alcohols with hexafluoropropene-diethylamine adduct (PPDA) to form 2-fluoro-2-trifluoromethyl-4-alkenamide
  作者：Ken-ichi Ogu、Motohiro Akazome、Katsuyuki Ogura

  DOI：10.1016/s0022-1139(03)00191-x

  日期：2003.11

  Treatment of allylic alcohols with hexafluoropropene-diethylamine adduct (PPDA) afforded N,N-diethyl-2-fluoro-2-trifluoromethyl-4-alkenamides which were formed by the Claisen rearrangement of intermediary 2-alkenyl-1-diethylamino-2,3,3,3-tetrafluoro-1-propenyl ethers. Although (E)-allylic alcohols gave two diastereomeric products in about 1:1 ratio, (Z)-allylic alcohols gave the corresponding product as a single diastereomer. (C) 2003 Elsevier B.V. All rights reserved.