2-Allyl-N-(2-bromoallyl)-N-methylaniline | 198285-18-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Allyl-N-(2-bromoallyl)-N-methylaniline
• 英文别名: N-(2-bromoprop-2-enyl)-N-methyl-2-prop-2-enylaniline
• CAS: 198285-18-6
• 化学式: C₁₃H₁₆BrN
• 分子量: 266.181
• InChiKey: HWWKEJNPMNNBMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Allyl-N-(2-bromoallyl)-N-methylaniline 在 zirconocene methyl chloride 、 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 以78%的产率得到2,3,4,5-Tetrahydro-1,4-dimethyl-3-methylene-1H-1-benzazepine
  参考文献：
  名称：

  Zirconium-Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven- and Eight-Membered Heterocycles

  摘要：

  AbstractThe development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.

  DOI：

  10.1002/chem.19970030820
• 作为产物：
  描述：

  2-allyl-phenylamine 在 potassium sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-Allyl-N-(2-bromoallyl)-N-methylaniline
  参考文献：
  名称：

  Zirconium-Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven- and Eight-Membered Heterocycles

  摘要：

  AbstractThe development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.

  DOI：

  10.1002/chem.19970030820

文献信息

• Zirconium-Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven- and Eight-Membered Heterocycles
  作者：José Barluenga、Roberto Sanz、Francisco J. Fañanás

  DOI：10.1002/chem.19970030820

  日期：1997.8

  AbstractThe development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.