N-[3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-heptadecafluoro-1-(4-trifluoromethylphenyl)dec-1-en-2-yl]morpholine | 790703-58-1

• 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-[3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-heptadecafluoro-1-(4-trifluoromethylphenyl)dec-1-en-2-yl]morpholine
• 英文别名: 4-[(Z)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-[4-(trifluoromethyl)phenyl]dec-1-en-2-yl]morpholine
• CAS: 790703-58-1
• 化学式: C₂₁H₁₃F₂₀NO
• 分子量: 675.308
• InChiKey: IMCOWMKSUOCQGP-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  N-[3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-heptadecafluoro-1-(4-trifluoromethylphenyl)dec-1-en-2-yl]morpholine 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 12.0h， 以96%的产率得到4-[2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-Heptadecafluoro-1-(4-trifluoromethyl-benzyl)-nonyl]-morpholine
  参考文献：
  名称：

  An easy three step synthesis of perfluoroalkylated amphetamines

  摘要：

  A general synthesis of perfluoroalkylated amphetamines is presented. Initially, 1-aryl-1-iodo-2-(perfluoroalkyl)ethylenes are prepared by radical addition of perfluoroalkyl iodides to arylacetylenes. Key step of the reaction sequence is the following dehydroiodination in the presence of n-BuLi to give 1-perfluoroalkyl-2-arylacetylenes in situ, which are reacted with secondary amines to produce perfluoroalkylated enamines in a new one pot procedure. Final hydrogenation yields the desired products in good yields. By using N,N-dibenzylamine or N-benzylamines the corresponding primary and secondary perfluoroalkylated amines are easily available. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.080
• 作为产物：
  描述：

  4-乙炔基-α,α,α-三氟甲苯 在 正丁基锂 、 二叔丁基过氧化物 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 36.0h， 生成 N-[3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-heptadecafluoro-1-(4-trifluoromethylphenyl)dec-1-en-2-yl]morpholine
  参考文献：
  名称：

  An easy three step synthesis of perfluoroalkylated amphetamines

  摘要：

  A general synthesis of perfluoroalkylated amphetamines is presented. Initially, 1-aryl-1-iodo-2-(perfluoroalkyl)ethylenes are prepared by radical addition of perfluoroalkyl iodides to arylacetylenes. Key step of the reaction sequence is the following dehydroiodination in the presence of n-BuLi to give 1-perfluoroalkyl-2-arylacetylenes in situ, which are reacted with secondary amines to produce perfluoroalkylated enamines in a new one pot procedure. Final hydrogenation yields the desired products in good yields. By using N,N-dibenzylamine or N-benzylamines the corresponding primary and secondary perfluoroalkylated amines are easily available. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.080

文献信息

• An easy three step synthesis of perfluoroalkylated amphetamines
  作者：Amit Tewari、Martin Hein、Alexander Zapf、Matthias Beller

  DOI：10.1016/j.tetlet.2004.08.080

  日期：2004.10

  A general synthesis of perfluoroalkylated amphetamines is presented. Initially, 1-aryl-1-iodo-2-(perfluoroalkyl)ethylenes are prepared by radical addition of perfluoroalkyl iodides to arylacetylenes. Key step of the reaction sequence is the following dehydroiodination in the presence of n-BuLi to give 1-perfluoroalkyl-2-arylacetylenes in situ, which are reacted with secondary amines to produce perfluoroalkylated enamines in a new one pot procedure. Final hydrogenation yields the desired products in good yields. By using N,N-dibenzylamine or N-benzylamines the corresponding primary and secondary perfluoroalkylated amines are easily available. (C) 2004 Elsevier Ltd. All rights reserved.