2,2,3,3,3-pentafluoro-N,N-dimethylpropionamide | 83599-57-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 2,2,3,3,3-pentafluoro-N,N-dimethylpropionamide
• 英文别名: N,N-dimethylpentafluoropropionamide；Dimethylamine, N-pentafluoropropionyl-；2,2,3,3,3-pentafluoro-N,N-dimethylpropanamide
• CAS: 83599-57-9
• 化学式: C₅H₆F₅NO
• 分子量: 191.101
• InChiKey: DSSAYXNOUMDUCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-dibromobenzo[b]thiophene 、 2,2,3,3,3-pentafluoro-N,N-dimethylpropionamide 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 4.75h， 以54%的产率得到1-(6-bromo-benzo[b]thiophen-3-yl)-2,2,3,3,3-pentafluoro-propan-1-one
  参考文献：
  名称：

  Potent BRAF kinase inhibitors based on 2,4,5-trisubstituted imidazole with naphthyl and benzothiophene 4-substituents

  摘要：

  The RAS-RAF-MEK-ERK pathway is hyperactivated in 30% of human cancers. BRAF is a serine-threonine kinase, belonging to this pathway that is mutated with high frequency in human melanoma and other cancers thus BRAF is an important therapeutic target in melanoma. We have designed inhibitors of BRAF based on 2,4,5-trisubstituted imidazoles with naphthyl and benzothiophene-4-substituents. Two compounds were discovered to be potent BRAF inhibitors: 1-(6-{2-[4-(2-dimethylamino-ethoxy) phenyl]-5-(pyridin-4-yl)-1H-imidazol-4-yl} benzo[b]thiophen-3-yl)-2,2,2-trifluoroethanol (1i) with BRAF IC50 = 190 nM and with cellular GI(50) = 2100 nM, and 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-naphthalen-1-ol (1q) with IC50 = 9 nM and GI(50) = 220 nM. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.035
• 作为产物：
  描述：

  五氟丙酰氟 、 二甲胺 以 乙醚 为溶剂， 以72.4%的产率得到2,2,3,3,3-pentafluoro-N,N-dimethylpropionamide
  参考文献：
  名称：

  Electrochemical fluorination of N,N-dimethylperfluoroacylamides

  摘要：

  The electrochemical fluorination (ECF) of N,N-dimethylperfluoroacylamides gives the corresponding perfluoro-N,N-dimethylacylamides in low yield. With increase of the number of carbon atoms in the perfluoroacyl radical the yield of the required perfluoro-NN-dimethylacylamides is slightly increased. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00545-0

文献信息

• Antiinflammatory 4,5-diaryl-.alpha.-(polyhalomethyl)-2-thiophenemethanols
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04381311A1

  公开（公告）日：1983-04-26

  4,5-Diaryl-.alpha.-(polyhalomethyl)-2-thiophenemethanols such as 4-(4-methoxyphenyl)-5-(4-methylthiophenyl)-.alpha.,.alpha.-bis(trifluorome thyl)-2-thiophenemethanol useful for treating arthritis and/or alleviating pain.

  4,5-二芳基-α-(多卤甲基)-2-噻吩甲醇，例如4-(4-甲氧基苯基)-5-(4-甲基噻吩基)-α，α-双(三氟甲基)-2-噻吩甲醇，用于治疗关节炎和/或缓解疼痛。
• A novel synthesis of per(poly)fluoroalkyl aldehydes
  作者：Chang-Ming Hu、Xiao-Qing Tang

  DOI：10.1016/s0022-1139(00)80105-0

  日期：1993.4

  A novel synthesis of per(poly)fluoroalkyl aldehydes in high yield by the reaction ofper(poly)fluoroalkyl iodides or bromides with dimethylformamide initiated by aPbBr2(catalyst)/Al bimetal redox system is described.

  通过由PbBr 2（催化剂）/ Al双金属氧化还原体系引发的全（多）氟烷基碘或溴化物与二甲基甲酰胺的反应，高产率地合成全（多）氟烷基醛。
• Potent BRAF kinase inhibitors based on 2,4,5-trisubstituted imidazole with naphthyl and benzothiophene 4-substituents
  作者：Dan Niculescu-Duvaz、Ion Niculescu-Duvaz、Bart M.J.M. Suijkerbuijk、Delphine Ménard、Alfonso Zambon、Lawrence Davies、Jean-Francois Pons、Steven Whittaker、Richard Marais、Caroline J. Springer

  DOI：10.1016/j.bmc.2012.12.035

  日期：2013.3

  The RAS-RAF-MEK-ERK pathway is hyperactivated in 30% of human cancers. BRAF is a serine-threonine kinase, belonging to this pathway that is mutated with high frequency in human melanoma and other cancers thus BRAF is an important therapeutic target in melanoma. We have designed inhibitors of BRAF based on 2,4,5-trisubstituted imidazoles with naphthyl and benzothiophene-4-substituents. Two compounds were discovered to be potent BRAF inhibitors: 1-(6-2-[4-(2-dimethylamino-ethoxy) phenyl]-5-(pyridin-4-yl)-1H-imidazol-4-yl} benzo[b]thiophen-3-yl)-2,2,2-trifluoroethanol (1i) with BRAF IC50 = 190 nM and with cellular GI(50) = 2100 nM, and 6-2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-naphthalen-1-ol (1q) with IC50 = 9 nM and GI(50) = 220 nM. (C) 2013 Elsevier Ltd. All rights reserved.
• Electrochemical fluorination of N,N-dimethylperfluoroacylamides
  作者：Nikolai V Ignat’ev、Michael Schmidt、Udo Heider、Andriy Kucherina、Peter Sartori、Fatiah M Helmy

  DOI：10.1016/s0022-1139(01)00545-0

  日期：2002.2

  The electrochemical fluorination (ECF) of N,N-dimethylperfluoroacylamides gives the corresponding perfluoro-N,N-dimethylacylamides in low yield. With increase of the number of carbon atoms in the perfluoroacyl radical the yield of the required perfluoro-NN-dimethylacylamides is slightly increased. (C) 2002 Elsevier Science B.V. All rights reserved.