1-(2-tert-butylphenyl)-1-methyl-3-phenylurea | 862891-94-9

• 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-butylphenyl)-1-methyl-3-phenylurea
• 英文别名: 1-(2-t-butylphenyl)-1-methyl-3-phenylurea
• CAS: 862891-94-9
• 化学式: C₁₈H₂₂N₂O
• 分子量: 282.385
• InChiKey: WVLNNFNQYZRYJY-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  445.6±28.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-tert-butylphenyl)-1-methyl-3-phenylurea 在 仲丁基锂 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 0.5h， 以80%的产率得到1-(2-tert-butyl-6-bromophenyl)-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
• 作为产物：
  描述：

  2-叔丁基苯胺 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 1-(2-tert-butylphenyl)-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

• Lateral lithiation of N,N′-diaryl ureas
  作者：Jonathan Clayden、Jérémy Dufour

  DOI：10.1016/j.tetlet.2006.07.134

  日期：2006.9

  sec-butyllithium. Quenching with a range of electrophiles yields functionalised aryl ureas in excellent yield. Lateral lithiation is favoured when the urea nitrogen adjacent to the aromatic ring in question is alkylated, and when competitive lithiations of such a ring are possible, lateral lithiation is more favourable than the alternative ortholithiation.

  带有N-（2-烷基芳基）基团的芳族脲可通过用仲丁基锂处理而横向锂化。用一系列亲电试剂猝灭可以以优异的产率产生官能化的芳基脲。当与所讨论的芳族环相邻的尿素氮被烷基化时，侧向锂化是有利的，并且当这种环的竞争性锂化是可能的时，侧向锂化比替代的原位锂化更有利。
• Enantiomerically enriched atropisomeric N,N′-diaryl ureas by oxidative kinetic resolution of their 2-sulfanyl derivatives
  作者：Jonathan Clayden、Hazel Turner

  DOI：10.1016/j.tetlet.2009.02.021

  日期：2009.7

  Atropisomeric N-methyl-N,N'-diaryl ureas may be obtained in enantiomerically enriched form by oxidative kinetic resolution of their sulfide derivatives. The atropisomeric sulfides may be obtained in up to 97:3 er and display high stability to racemisation (half-lives at 25 degrees C of up to 500 years). Unlike related fully alkylated ureas, the product sulfoxides exhibit relatively weak thermodynamic conformational selectivity. (C) 2009 Elsevier Ltd. All rights reserved.
• <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.