1-methyl-2-trifluoromethyl-4,5-dihydropyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-methyl-2-trifluoromethyl-4,5-dihydropyrrole
• 英文别名: Pyrrole, 4,5-dihydro-1-methyl-2-(trifluoromethyl)-；1-methyl-5-(trifluoromethyl)-2,3-dihydropyrrole
• 化学式: C₆H₈F₃N
• 分子量: 151.131
• InChiKey: BDAWGMFMEUPZAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-2-trifluoromethyl-4,5-dihydropyrrole 在 盐酸 、 sodium hydroxide 、 水 作用下， 以60%的产率得到2-hydroxy-1-methyl-2-trifluoromethyl-pyrrolidine
  参考文献：
  名称：

  A simple one-pot synthesis of α-trifluoromethyl-substituted enamines by C-trifluoromethylation of dialkylamides with

  摘要：

  Dialkylamides of the general formula R(3)R(2)NC(O)CH(2)R(1), and Me-N-C(O)-CH2-(CH2)(n)-CH2, n=1-3, react with the reagent combination P(NEt(2))(3)/CF3Br in the presence of BCl3 to give alpha-trifluoromethyl enamines R(3)R(2)N-C(CF3)=CHR(1), R(1)=H, R(2)=R(3)=Me (I), Et(II), Pr-i(III); R(2)=(n)Bu, R(3)=Me(IV); R(1)=R(2)=R(3)=Me(Va/b); Me-N-C(CF3)=CH-(CH2)(n)-CH2, n=1 (VI), 2 (VII) and 3 (VIII) in yields of 25%-36%. Hydrolysis of VI by hydrochloric acid yielded the salt [Me-NH-C(CF3)(OH)-CH2-CH2-CH2]Cl-+(-) (IX), the deprotonation of which with NaOH gave the 2-hydroxypyrrolidine Me-N-C(CF3)(OH)-CH2-CH2-CH2 (X). The novel compounds have been characterized by elemental analyses, multinuclear NMR, IR and mass spectroscopy.

  DOI：

  10.1016/0022-1139(94)03090-m
• 作为产物：
  描述：

  N-甲基吡咯烷酮 、 三氟溴甲烷 在 三氯化硼 、 六乙基亚磷酸胺 作用下， 以30%的产率得到1-methyl-2-trifluoromethyl-4,5-dihydropyrrole
  参考文献：
  名称：

  A simple one-pot synthesis of α-trifluoromethyl-substituted enamines by C-trifluoromethylation of dialkylamides with

  摘要：

  Dialkylamides of the general formula R(3)R(2)NC(O)CH(2)R(1), and Me-N-C(O)-CH2-(CH2)(n)-CH2, n=1-3, react with the reagent combination P(NEt(2))(3)/CF3Br in the presence of BCl3 to give alpha-trifluoromethyl enamines R(3)R(2)N-C(CF3)=CHR(1), R(1)=H, R(2)=R(3)=Me (I), Et(II), Pr-i(III); R(2)=(n)Bu, R(3)=Me(IV); R(1)=R(2)=R(3)=Me(Va/b); Me-N-C(CF3)=CH-(CH2)(n)-CH2, n=1 (VI), 2 (VII) and 3 (VIII) in yields of 25%-36%. Hydrolysis of VI by hydrochloric acid yielded the salt [Me-NH-C(CF3)(OH)-CH2-CH2-CH2]Cl-+(-) (IX), the deprotonation of which with NaOH gave the 2-hydroxypyrrolidine Me-N-C(CF3)(OH)-CH2-CH2-CH2 (X). The novel compounds have been characterized by elemental analyses, multinuclear NMR, IR and mass spectroscopy.

  DOI：

  10.1016/0022-1139(94)03090-m

文献信息

• A simple one-pot synthesis of α-trifluoromethyl-substituted enamines by C-trifluoromethylation of dialkylamides with
  作者：Hans Bürger、Thomas Dittmar、Gottfried Pawelke

  DOI：10.1016/0022-1139(94)03090-m

  日期：1995.1

  Dialkylamides of the general formula R(3)R(2)NC(O)CH(2)R(1), and Me-N-C(O)-CH2-(CH2)(n)-CH2, n=1-3, react with the reagent combination P(NEt(2))(3)/CF3Br in the presence of BCl3 to give alpha-trifluoromethyl enamines R(3)R(2)N-C(CF3)=CHR(1), R(1)=H, R(2)=R(3)=Me (I), Et(II), Pr-i(III); R(2)=(n)Bu, R(3)=Me(IV); R(1)=R(2)=R(3)=Me(Va/b); Me-N-C(CF3)=CH-(CH2)(n)-CH2, n=1 (VI), 2 (VII) and 3 (VIII) in yields of 25%-36%. Hydrolysis of VI by hydrochloric acid yielded the salt [Me-NH-C(CF3)(OH)-CH2-CH2-CH2]Cl-+(-) (IX), the deprotonation of which with NaOH gave the 2-hydroxypyrrolidine Me-N-C(CF3)(OH)-CH2-CH2-CH2 (X). The novel compounds have been characterized by elemental analyses, multinuclear NMR, IR and mass spectroscopy.