1-(3-methoxyphenyl)-1,3-dimethyl-3-[(Z)-1-phenylprop-1-enyl]urea | 1256930-47-8

• 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: 1-(3-methoxyphenyl)-1,3-dimethyl-3-[(Z)-1-phenylprop-1-enyl]urea
• 英文别名: 1-(3-methoxyphenyl)-1,3-dimethyl-3-((Z)-1-phenylpropenyl)urea
• CAS: 1256930-47-8
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: WFCBMIZLZCBROU-DVZOWYKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-methoxyphenyl)-1,3-dimethyl-3-[(Z)-1-phenylprop-1-enyl]urea 在 lithium diisopropyl amide 、 N,N-二甲基丙烯基脲 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以56%的产率得到(+/-)-1-[1-(3-methoxyphenyl)-1-phenylallyl]-1,3-dimethylurea
  参考文献：
  名称：

  Sequential Double α-Arylation of N-Allylureas by Asymmetric Deprotonation and N→C Aryl Migration

  摘要：

  On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic alpha carbon. From the alpha-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control.

  DOI：

  10.1021/ol102155h
• 作为产物：
  描述：

  在 silica gel 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到1-(3-methoxyphenyl)-1,3-dimethyl-3-[(Z)-1-phenylprop-1-enyl]urea
  参考文献：
  名称：

  Geometry-Selective Synthesis of E or Z N-Vinyl Ureas (N-Carbamoyl Enamines)

  摘要：

  N-Vinyl ureas are emerging as a valuable class of compounds with both nucleophilic and electrophilic reactivity. They may be made by capturing the enamine tautomer of an imine with an isocyanate, a reaction which in general leads to the E isomer of the vinyl urea. Deprotonation of such a vinyl urea, or of an allyl urea, generates a dipole stabilized Z-allyl anion which may be protonated to return the Z-vinyl urea. Isomerization of an allyl urea with a Ru complex provides an alternative route to E-vinyl ureas.

  DOI：

  10.1021/ol1027442