(+)-1-[1-(4-chlorophenyl)-1-(4-cyanophenyl)allyl]-1-(4-methoxyphenyl)-3-methylurea | 1256930-39-8

• 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-[1-(4-chlorophenyl)-1-(4-cyanophenyl)allyl]-1-(4-methoxyphenyl)-3-methylurea
• 英文别名: 1-[(1S)-1-(4-chlorophenyl)-1-(4-cyanophenyl)prop-2-enyl]-1-(4-methoxyphenyl)-3-methylurea
• CAS: 1256930-39-8
• 化学式: C₂₅H₂₂ClN₃O₂
• 分子量: 431.922
• InChiKey: CUDSOIMXQLLJFW-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-1-(1-(4-chlorophenyl)prop-1-enyl)-3-(4-cyanophenyl)-1-(4-methoxyphenyl)-3-methylurea 在 lithium (S)-(-)-N-isopropyl-1-phenylethylamide 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 (+)-1-[1-(4-chlorophenyl)-1-(4-cyanophenyl)allyl]-1-(4-methoxyphenyl)-3-methylurea 、 (-)-1-[1-(4-chlorophenyl)-1-(4-cyanophenyl)allyl]-1-(4-methoxyphenyl)-3-methylurea
  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.