1-(4-methoxyphenyl)-3-methyl-1-((Z)-1-phenylpropenyl)urea | 1256929-96-0

• 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: 1-(4-methoxyphenyl)-3-methyl-1-((Z)-1-phenylpropenyl)urea
• 英文别名: 1-(4-methoxyphenyl)-3-methyl-1-[(Z)-1-phenylprop-1-enyl]urea
• CAS: 1256929-96-0
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: VJYYFFYPKVEFQV-INGKJJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴-6-甲氧基吡啶 、 1-(4-methoxyphenyl)-3-methyl-1-((Z)-1-phenylpropenyl)urea 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以89%的产率得到1-(4-methoxyphenyl)-3-(6-methoxypyridin-2-yl)-3-methyl-1-((Z)-1-phenylpropenyl)urea
  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：

  1-allyl-1-(4-methoxyphenyl)-3-methyl-3-phenylurea 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 3.17h， 以74%的产率得到1-(4-methoxyphenyl)-3-methyl-1-((Z)-1-phenylpropenyl)urea
  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

文献信息

• Sequential Double α-Arylation of <i>N</i>-Allylureas by Asymmetric Deprotonation and N→C Aryl Migration
  作者：Daniel J. Tetlow、Ulrich Hennecke、James Raftery、Michael J. Waring、David S. Clarke、Jonathan Clayden

  DOI：10.1021/ol102155h

  日期：2010.12.3

  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.