2-bromo-N-(3,3-difluoroallyl)aniline | 1565823-32-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-bromo-N-(3,3-difluoroallyl)aniline
• 英文别名: 2-bromo-N-(3,3-difluoroprop-2-enyl)aniline
• CAS: 1565823-32-6
• 化学式: C₉H₈BrF₂N
• 分子量: 248.07
• InChiKey: IWMXTYYPCIKKAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(3,3-difluoroallyl)aniline 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 正己烷 为溶剂， 反应 6.0h， 以94%的产率得到3-(difluoromethyl)indoline
  参考文献：
  名称：

  Two-Step Synthesis of Difluoromethyl-Substituted 2,3-Dihydrobenzoheteroles

  摘要：

  3-Difluoromethylated 2,3-dihydrobenzoheteroles, 2,3-dihydrobenzofurans, 2,3-dihydrobenzothiophenes, and indolines were readily synthesized from ortho-heterosubstituted bromobenzenes, 2-bromophenols, 2-bromobenzenethiols, and 2-bromoanilines, respectively, in two steps: (1) gamma-selective allylic substitution of 3-bromo-3,3-difluoropropene with heteronucleophiles and (2) intramolecular radical cyclization of the resulting 3,3-difluoroallylic compounds.

  DOI：

  10.1021/ol5001582
• 作为产物：
  描述：

  3-溴-3,3-二氟丙烯 、 2-溴苯胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.17h， 以92%的产率得到2-bromo-N-(3,3-difluoroallyl)aniline
  参考文献：
  名称：

  Two-Step Synthesis of Difluoromethyl-Substituted 2,3-Dihydrobenzoheteroles

  摘要：

  3-Difluoromethylated 2,3-dihydrobenzoheteroles, 2,3-dihydrobenzofurans, 2,3-dihydrobenzothiophenes, and indolines were readily synthesized from ortho-heterosubstituted bromobenzenes, 2-bromophenols, 2-bromobenzenethiols, and 2-bromoanilines, respectively, in two steps: (1) gamma-selective allylic substitution of 3-bromo-3,3-difluoropropene with heteronucleophiles and (2) intramolecular radical cyclization of the resulting 3,3-difluoroallylic compounds.

  DOI：

  10.1021/ol5001582

文献信息

• Two-Step Synthesis of Difluoromethyl-Substituted 2,3-Dihydrobenzoheteroles
  作者：Takeshi Fujita、Shohei Sanada、Yosuke Chiba、Kazuki Sugiyama、Junji Ichikawa

  DOI：10.1021/ol5001582

  日期：2014.3.7

  3-Difluoromethylated 2,3-dihydrobenzoheteroles, 2,3-dihydrobenzofurans, 2,3-dihydrobenzothiophenes, and indolines were readily synthesized from ortho-heterosubstituted bromobenzenes, 2-bromophenols, 2-bromobenzenethiols, and 2-bromoanilines, respectively, in two steps: (1) gamma-selective allylic substitution of 3-bromo-3,3-difluoropropene with heteronucleophiles and (2) intramolecular radical cyclization of the resulting 3,3-difluoroallylic compounds.