1-Benzyl-3-[(3-chlorophenyl)methyl]urea

• 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-Benzyl-3-[(3-chlorophenyl)methyl]urea
• 化学式: C₁₅H₁₅ClN₂O
• 分子量: 274.75
• InChiKey: PGAWRAXDXJLXPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙酸 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 1-Benzyl-3-[(3-chlorophenyl)methyl]urea
  参考文献：
  名称：

  Thiol on silica as a ‘catch and release’ support for isocyanates to afford ureas

  摘要：

  Silica-bound thiocarbamates were prepared by Curtius rearrangement of carboxylic acids in the presence of thiol on silica gel. The solid supported thiocarbamates were found to be stable isocyanate equivalents, which upon treatment with amines efficiently afforded di- and tri-substituted ureas. The urea products released from the catch and release support were, in the majority of cases, greater than 95% pure and required no further work. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.050

文献信息

• Kinetics and Mechanism of the Aminolysis of Aryl N-Benzyl Thiocarbamates in Acetonitrile
  作者：Hyuck-Keun Oh

  DOI：10.5012/bkcs.2011.32.1.137

  日期：2011.1.20

  The aminolysis reactions of phenyl N-benzyl thiocarbamate with benzylamines in acetonitrile at $50.0^\circ}C$ are investigated. The reactions are first order in both the amine and the substrate. Under amine excess, pseudo-first coefficient ($k_obs}$) are obtained, plot of $k_obs}$ vs free amine concentration are linear. The signs of $\rho}_XZ}$ (< 0) are consistent with concerted mechanism. Moreover, the variations of $\rho_X$ and $\rho_Z$ with respect to the sustituent in the substrate and large $\rho}_XZ}$ value indicate that the reactions proceed concerted mechanism. The normal kinetic isotope effects ($k_H/k_D$ = 1.3 ~ 1.5) involving deuterated benzylamine nucleophiles suggest a hydrogen-bonded, four-centered-type transition state. The activation parameters, $\Delta}H^\ddagger$ and $\Delta}S^\ddagger$, are consistent with this transition state structure.

  对苯基 N-苄基硫代氨基甲酸酯与苄胺在乙腈中50.0°C下的氨解反应进行了研究。反应对胺和底物均为一级。在胺过量情况下，获得了伪一级速率常数（$k_obs}$），$k_obs}$ 与游离胺浓度的关系图为线性。参量 $\rho_XZ}$（< 0）的符号与协同机理一致。此外，$\rho_X$ 和 $\rho_Z$ 随底物取代基的变化以及较大的 $\rho_XZ}$ 值表明反应通过协同机理进行。正常的动力学同位素效应（$k_H/k_D$ = 1.3 ~ 1.5）涉及氘代苄胺亲核试剂，表明过渡态为氢键作用的四中心类型。活化参数 $\Delta H^\ddagger$ 和 $\Delta S^\ddagger$ 与此过渡态结构相符。
• Thermolysis of Geminal Diazido Malonamides: Simple Access to Tetrazoles and Functionalization of In Situ Formed Isocyanates
  作者：Kathrin Bensberg、Kevin A. Kunz、Stefan F. Kirsch

  DOI：10.1002/ejoc.202300212

  日期：2023.5.8

  Tetrazole or urea compound: The thermolytical decomposition under microwave irradiation of diazidated malonamides was studied. A variety of different tetrazoles could be synthesized in three steps starting from diethyl malonate. Furthermore, the formation of isocyanates in situ was investigated.

  四唑或脲化合物：研究了二叠氮基丙二酰胺在微波辐射下的热分解。从丙二酸二乙酯开始，可以通过三个步骤合成多种不同的四唑。此外，还研究了原位异氰酸酯的形成。
• Thiol on silica as a ‘catch and release’ support for isocyanates to afford ureas
  作者：Yuri Bolshan、Miroslaw J. Tomaszewski、Vijayaratnam Santhakumar

  DOI：10.1016/j.tetlet.2007.05.050

  日期：2007.7

  Silica-bound thiocarbamates were prepared by Curtius rearrangement of carboxylic acids in the presence of thiol on silica gel. The solid supported thiocarbamates were found to be stable isocyanate equivalents, which upon treatment with amines efficiently afforded di- and tri-substituted ureas. The urea products released from the catch and release support were, in the majority of cases, greater than 95% pure and required no further work. (c) 2007 Elsevier Ltd. All rights reserved.