2-bromo-N-(furan-2-ylmethyl)-N-methylaniline | 114325-54-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-bromo-N-(furan-2-ylmethyl)-N-methylaniline
• CAS: 114325-54-1
• 化学式: C₁₂H₁₂BrNO
• 分子量: 266.137
• InChiKey: YCCMVDIWRPWYIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  335.6±32.0 °C(predicted)
• 密度：
  1.422±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  16.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(furan-2-ylmethyl)-N-methylaniline 在 四(三苯基膦)钯 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以83%的产率得到(E)-3-(1-methyl-1H-indol-3-yl)acrylaldehyde
  参考文献：
  名称：

  A Novel Entry to Functionalized Benzofurans and Indoles via Palladium(0)-Catalyzed Arylative Dearomatization of Furans

  摘要：

  A novel entry to functionalized benzofurans and indoles from furans in moderate to good yields has been developed. This protocol involves palladium(0)-catalyzed dearomatizing intramolecular arylation of the furan ring, formation of a pi-allylic palladium complex, furan ring opening, and a beta-hydride elimination sequence.

  DOI：

  10.1021/ol300008d
• 作为产物：
  描述：

  2-溴苯胺 在 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 36.0h， 生成 2-bromo-N-(furan-2-ylmethyl)-N-methylaniline
  参考文献：
  名称：

  A Novel Entry to Functionalized Benzofurans and Indoles via Palladium(0)-Catalyzed Arylative Dearomatization of Furans

  摘要：

  A novel entry to functionalized benzofurans and indoles from furans in moderate to good yields has been developed. This protocol involves palladium(0)-catalyzed dearomatizing intramolecular arylation of the furan ring, formation of a pi-allylic palladium complex, furan ring opening, and a beta-hydride elimination sequence.

  DOI：

  10.1021/ol300008d

文献信息

• Scope of tandem cycloadditon/radical cyclization methodology
  作者：Tirthankar Ghosh、Harold Hart

  DOI：10.1021/jo00282a022

  日期：1989.10
• Tandem cycloaddition/radical cyclization, a widely applicable strategy for the rapid assembly of polycyclic systems
  作者：Tirthankar Ghosh、Harold Hart

  DOI：10.1021/jo00245a060

  日期：1988.5
• GHOSH, T.;HART, H., J. ORG. CHEM., 53,(1988) N 10, 2396-2398
  作者：GHOSH, T.、HART, H.

  DOI：——

  日期：——
• A Novel Entry to Functionalized Benzofurans and Indoles <i>via</i> Palladium(0)-Catalyzed Arylative Dearomatization of Furans
  作者：Biaolin Yin、Congbi Cai、Guohui Zeng、Ruoqi Zhang、Xiang Li、Huanfeng Jiang

  DOI：10.1021/ol300008d

  日期：2012.2.17

  A novel entry to functionalized benzofurans and indoles from furans in moderate to good yields has been developed. This protocol involves palladium(0)-catalyzed dearomatizing intramolecular arylation of the furan ring, formation of a pi-allylic palladium complex, furan ring opening, and a beta-hydride elimination sequence.