1-(2-tert-butyl-6-formylphenyl)-1-methyl-3-phenylurea | 862892-05-5

• 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-(2-tert-butyl-6-formylphenyl)-1-methyl-3-phenylurea
• 英文别名: 1-(2-t-butyl-6-formylphenyl)-1-methyl-3-phenylurea；1-(2-Tert-butyl-6-formylphenyl)-1-methyl-3-phenylurea
• CAS: 862892-05-5
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: LDPKPUFLZPZAGU-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C
• 沸点：
  488.7±45.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-tert-butyl-6-formylphenyl)-1-methyl-3-phenylurea 、 phenylmagnesium bromide 以63%的产率得到1-(2-tert-butyl-6-(hydroxy(phenyl)methyl)phenyl)-1-methyl-3-phenylurea
  参考文献：
  名称：

  N,N′-Diarylureas: A New Family of Atropisomers Exhibiting Highly Diastereoselective Reactivity

  摘要：

  2,6-Disubstituted N-aryl ureas rotate slowly about their Ar-N bonds and can exist as separable atropisomers. They also react remarkably diastereoselectively, with the urea axis controlling new stereogenic centers with high fidelity in a variety of nucleophilic and electrophilic addition reactions. The sense of diastereoselectivity in lateral lithiation-electrophilic quench reactions is electrophile-dependent and appears to be the result of stereospecific reaction with one of two interconvertible diastereoisomeric organolithiums.

  DOI：

  10.1021/jo702706c
• 作为产物：
  描述：

  2-叔丁基苯胺 在 仲丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 36.5h， 生成 1-(2-tert-butyl-6-formylphenyl)-1-methyl-3-phenylurea
  参考文献：
  名称：

  Ring-Selective Functionalization of N,N‘-Diarylureas by Regioselective N-Alkylation and Directed Ortho Metalation

  摘要：

  Unsymmetrical N,N'-diarylureas may be alkylated regioselectively at the more sterically congested nitrogen atom. The resulting mono-N-alkylated ureas undergo directed metalation (ortholithiation) with sec-BuLi to yield, on electrophilic quench, products functionalized regioselectively at the ring bearing the alkylated nitrogen atom.

  DOI：

  10.1021/ol0508025

文献信息

• Ring-Selective Functionalization of <i>N</i>,<i>N</i><i>‘</i>-Diarylureas by Regioselective N-Alkylation and Directed Ortho Metalation
  作者：Jonathan Clayden、Hazel Turner、Mark Pickworth、Thomas Adler

  DOI：10.1021/ol0508025

  日期：2005.7.1

  Unsymmetrical N,N'-diarylureas may be alkylated regioselectively at the more sterically congested nitrogen atom. The resulting mono-N-alkylated ureas undergo directed metalation (ortholithiation) with sec-BuLi to yield, on electrophilic quench, products functionalized regioselectively at the ring bearing the alkylated nitrogen atom.
• <i>N</i>,<i>N′</i>-Diarylureas: A New Family of Atropisomers Exhibiting Highly Diastereoselective Reactivity
  作者：Jonathan Clayden、Hazel Turner、Madeleine Helliwell、Elizabeth Moir

  DOI：10.1021/jo702706c

  日期：2008.6.1

  2,6-Disubstituted N-aryl ureas rotate slowly about their Ar-N bonds and can exist as separable atropisomers. They also react remarkably diastereoselectively, with the urea axis controlling new stereogenic centers with high fidelity in a variety of nucleophilic and electrophilic addition reactions. The sense of diastereoselectivity in lateral lithiation-electrophilic quench reactions is electrophile-dependent and appears to be the result of stereospecific reaction with one of two interconvertible diastereoisomeric organolithiums.