(4-methoxy-phenyl)-(1-p-chloro-phenyl-allyl)-amine | 1256930-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4-methoxy-phenyl)-(1-p-chloro-phenyl-allyl)-amine
• 英文别名: (4-methoxyphenyl)(1-(p-chlorophenyl)allyl)amine；(4-methoxyphenyl)-(1-p-chlorophenylallyl)amine
• CAS: 1256930-34-3
• 化学式: C₁₆H₁₆ClNO
• 分子量: 273.762
• InChiKey: DLXZYEIQDIMVNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4-methoxy-phenyl)-(1-p-chloro-phenyl-allyl)-amine 、 4-氰基苯异氰酸酯 以 二氯甲烷 为溶剂， 生成
  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

文献信息

• Reversible aryl migrations in metallated ureas: controlled inversion of configuration at a quaternary carbon atom
  作者：Daniel J. Tetlow、Mark A. Vincent、Ian H. Hillier、Jonathan Clayden

  DOI：10.1039/c2cc38704b

  日期：——

  Deprotonation with strong bases of N-vinyl ureas carrying an N′-aryl substituent leads to migration of the N′-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents α to the urea N atom may migrate from C to N.

  带有 N′-芳基取代基的 N-乙烯基脲在强碱作用下发生去质子化反应，导致 N′-芳基通过烯丙基锂从 N 转移到 C；在弱碱和缺电子芳基环作用下，转移方向发生逆转，脲 N 原子上的α芳基取代基可能会从 C 转移到 N。
• 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.