1-indan-1-yl-1,3-dimethyl-3-vinylurea | 1371664-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-indan-1-yl-1,3-dimethyl-3-vinylurea
• CAS: 1371664-63-9
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: BQWOBFPKCYLKKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  23.55
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-indan-1-yl-1,3-dimethyl-3-vinylurea 在 N,N-二甲基丙烯基脲 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以45%的产率得到1,3-dimethyl-1-(1-vinylindan-1-yl)urea
  参考文献：
  名称：

  Intramolecular Vinylation of Secondary and Tertiary Organolithiums

  摘要：

  Deprotonation of benzylic ureas, carbamates, and thiocarbamates bearing N'-alkenyl substituents generates carbanions which undergo intramolecular migration of the alkenyl group to the carbanionic center. Solvolysis of the urea products generates alpha-alkenylated amines. With an enantiomerically pure starting urea, migration proceeds stereospecifically, generating in enantiomerically enriched form products containing allylic quaternary stereogenic centers bearing N. Computational and in situ IR studies suggest that the reaction, formally a nucleophilic substitution at an sp(2) carbon atom, proceeds by a concerted addition-elimination pathway.

  DOI：

  10.1021/ja301591m
• 作为产物：
  描述：

  、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.5h， 以90 mg的产率得到1-indan-1-yl-1,3-dimethyl-3-vinylurea
  参考文献：
  名称：

  Intramolecular Vinylation of Secondary and Tertiary Organolithiums

  摘要：

  Deprotonation of benzylic ureas, carbamates, and thiocarbamates bearing N'-alkenyl substituents generates carbanions which undergo intramolecular migration of the alkenyl group to the carbanionic center. Solvolysis of the urea products generates alpha-alkenylated amines. With an enantiomerically pure starting urea, migration proceeds stereospecifically, generating in enantiomerically enriched form products containing allylic quaternary stereogenic centers bearing N. Computational and in situ IR studies suggest that the reaction, formally a nucleophilic substitution at an sp(2) carbon atom, proceeds by a concerted addition-elimination pathway.

  DOI：

  10.1021/ja301591m