1-丁基-3-(2,6-二甲基苯基)脲 | 39143-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-丁基-3-(2,6-二甲基苯基)脲
• 英文名称: 1-butyl-3-[2,6-dimethylphenyl]urea
• 英文别名: 1-Butyl-3-(2,6-dimethylphenyl)urea
• CAS: 39143-71-0
• 化学式: C₁₃H₂₀N₂O
• mdl: MFCD00089229
• 分子量: 220.315
• InChiKey: SYSPPBFQNQIPGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  1-丁基-3-(2,6-二甲基苯基)脲 在 四(三苯基膦)钯 、 三乙胺 、 三苯基膦 、 二溴三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 [3-Butyl-4-vinyl-oxazolidin-(2Z)-ylidene]-(2,6-dimethyl-phenyl)-amine
  参考文献：
  名称：

  Highly Enantioselective Synthesis of 1,3-Oxazolidin-2-imine Derivatives by Asymmetric Cycloaddition Reactions of Vinyloxiranes with Unsymmetrical Carbodiimides Catalyzed by Palladium(0) Complexes

  摘要：

  4-Vinyl-1,3-oxazoilidin-2-imine derivatives have been synthesized by cycloaddition reactions of 2-vinyloxiranes with unsymmetrical carbodiimides catalyzed by palladium(0) complexes-in excellent total isolated yields. After reaction two compounds were always formed, one of which was isolated as the major product. A bulky alkyl group on one of the nitrogen atoms of the carbodiimide enhanced the product ratio in favor of the N-aryl-3-alkyl-1,3-oxazolidin-2-imine. Highly enantioselective cycloadducts (up to >99% ee) were formed by using TolBINAP as the chiral phosphine ligand, in THF at ambient temperatures. The enantiodetermination is believed to be dependent on nucleophilic attack of the anionic nitrogen of the carbodiimide due to the steric interaction of the carbodiimide substituents with the chiral phosphine ligand.

  DOI：

  10.1021/jo9804341
• 作为产物：
  描述：

  正丁胺 、 2,6-二甲苯基异氰酸酯 以 二氯甲烷 为溶剂， 反应 24.0h， 以59%的产率得到1-丁基-3-(2,6-二甲基苯基)脲
  参考文献：
  名称：

  Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution

  摘要：

  苯脲部分是超分子化学中普遍存在的合成子。本文报道，在尿素单元的邻位引入氯或溴原子是一种简单且极为有效的方法，可提升其分子间氢键供体的性质。该效应在溶液中的自聚二脲和单脲与强氢键受体的氢键作用两种情况下均得到了验证。

  DOI：

  10.1039/c3cc47447j

文献信息

• Oxidative α-addition of isonitrile by use of mercuric salts synthesis of urea and urethane
  作者：Hiroaki Sawai、Takeo Takizawa

  DOI：10.1016/s0040-4039(01)94290-x

  日期：1972.1
• Joshua, C P; Sujatha, T S, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 6, p. 600 - 603
  作者：Joshua, C P、Sujatha, T S

  DOI：——

  日期：——
• Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution
  作者：Ilaria Giannicchi、Benjamin Jouvelet、Benjamin Isare、Mathieu Linares、Antonella Dalla Cort、Laurent Bouteiller

  DOI：10.1039/c3cc47447j

  日期：——

  The phenylurea moiety is a ubiquitous synthon in supramolecular chemistry. Here we report that the introduction of chlorine or bromine atoms in the ortho positions to the urea unit is a simple and very efficient way to improve its intermolecular hydrogen bond (HB) donor character. This effect was demonstrated in solution both in the context of self-association of bis-ureas and hydrogen bonding of mono-ureas to strong HB acceptors.

  苯脲部分是超分子化学中普遍存在的合成子。本文报道，在尿素单元的邻位引入氯或溴原子是一种简单且极为有效的方法，可提升其分子间氢键供体的性质。该效应在溶液中的自聚二脲和单脲与强氢键受体的氢键作用两种情况下均得到了验证。
• Highly Enantioselective Synthesis of 1,3-Oxazolidin-2-imine Derivatives by Asymmetric Cycloaddition Reactions of Vinyloxiranes with Unsymmetrical Carbodiimides Catalyzed by Palladium(0) Complexes
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/jo9804341

  日期：1998.9.1

  4-Vinyl-1,3-oxazoilidin-2-imine derivatives have been synthesized by cycloaddition reactions of 2-vinyloxiranes with unsymmetrical carbodiimides catalyzed by palladium(0) complexes-in excellent total isolated yields. After reaction two compounds were always formed, one of which was isolated as the major product. A bulky alkyl group on one of the nitrogen atoms of the carbodiimide enhanced the product ratio in favor of the N-aryl-3-alkyl-1,3-oxazolidin-2-imine. Highly enantioselective cycloadducts (up to >99% ee) were formed by using TolBINAP as the chiral phosphine ligand, in THF at ambient temperatures. The enantiodetermination is believed to be dependent on nucleophilic attack of the anionic nitrogen of the carbodiimide due to the steric interaction of the carbodiimide substituents with the chiral phosphine ligand.