4-<2-dimethylaminomethylphenyl>-2-pentanone | 135679-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-<2-dimethylaminomethylphenyl>-2-pentanone
• 英文别名: 4-[2-[(dimethylamino)methyl]phenyl]pentan-2-one
• CAS: 135679-30-0
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: LIMLKGNVBVNHKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (E)-methyl 3-(2-((dimethylamino)methyl)phenyl)acrylate 、 lithium dimethylcuprate 在 氨 、 氯化铵 作用下， 以 乙醚 为溶剂， 生成 methyl 3-<2-dimethylaminomethylphenyl>-butanoate 、 4-<2-dimethylaminomethylphenyl>-2-pentanone
  参考文献：
  名称：

  Stereoselective addition of R2CuLi to ortho-substituted methyl cinnamates intramolecular assistance and solvent effects

  摘要：

  High chemical yields are obtained on the addition of the ortho-substituted enoates 1,2,3, and 4 to Me2CuLi or Ph2CuLi in non-coordinating solvents, CH2Cl2 or toluene. The results underline the strong effect of solvent on reactions between organocuprates and enoates as the corresponding reactions in diethyl ether afforded low yields and moderate steroselectivity. No reaction was observed when THF was used. The high steroselectivity observed with the dimethylaminoethyl substituted enoate 4 in non-coordinating solvents can be accommodated by a mechanistic model for the reaction based on chelation control, within a copper-alkene pi-complex.

  DOI：

  10.1016/s0040-4020(01)86478-4

文献信息

• Stereoselective addition of R2CuLi to ortho-substituted methyl cinnamates intramolecular assistance and solvent effects
  作者：Beritte Christenson、Gerd Hallnemo、Christina Ullenius

  DOI：10.1016/s0040-4020(01)86478-4

  日期：1991.1

  High chemical yields are obtained on the addition of the ortho-substituted enoates 1,2,3, and 4 to Me2CuLi or Ph2CuLi in non-coordinating solvents, CH2Cl2 or toluene. The results underline the strong effect of solvent on reactions between organocuprates and enoates as the corresponding reactions in diethyl ether afforded low yields and moderate steroselectivity. No reaction was observed when THF was used. The high steroselectivity observed with the dimethylaminoethyl substituted enoate 4 in non-coordinating solvents can be accommodated by a mechanistic model for the reaction based on chelation control, within a copper-alkene pi-complex.