1,1-二苄基-3-苯基脲 | 53693-57-5

• 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: 1,1-二苄基-3-苯基脲
• 英文名称: 1,1-dibenzyl-3-phenylurea
• 英文别名: N,N-dibenzyl-N'-phenylurea
• CAS: 53693-57-5
• 化学式: C₂₁H₂₀N₂O
• mdl: MFCD00020637
• 分子量: 316.403
• InChiKey: PTHTXCJHLYXEMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.095
• 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：

  1,1-二苄基-3-苯基脲 在 rhodium(II) octanoate 正丁基锂 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 、 苯 为溶剂， 反应 4.5h， 生成 4-acetyl-5-carbmethoxy-1-(dibenzylamino)-6H-7-oxa-3-oxo-2-phenyl-2-azabicyclo<2.2.1>hept-5-ene
  参考文献：
  名称：

  Synthesis of nitrogen-containing polycycles via rhodium(II)-induced cyclization-cycloaddition and insertion reactions of N-(diazoacetoacetyl)amides. Conformational control of reaction selectivity

  摘要：

  A series of diazoacetoacetamides, when treated with a catalytic quantity of a rhodium(II) carboxylate, were found to afford products derived from both a carbonyl ylide intermediate and intramolecular C-H insertion. With 3-(N-(diazoacetoacetyl)amino)propanoate derivatives, the rhodium(II)-catalyzed carbenoid reactions exhibit a strong preference for formation of a beta-lactam ring. This is attributed to a conformational preference that juxtaposes the carbenoid center and the less sterically encumbered amide substituent and is consistent with an activating influence on the C-H bond adjacent to the amide nitrogen atom. Carbonyl ylide products derived from carbenoid cyclization onto the ester carbonyl group are also formed, and their relative yields are dependent on electronic influences from the bridging ligands of rhodium(II). Treatment of a series of cyclic diazoimides with rhodium(II) acetate resulted in cyclization of the rhodium carbenoid onto the adjacent imide carbonyl group to produce an isomunchnone dipole. Cyclization onto the imide carbonyl group occurs exclusively even when C-H insertion or aromatic substitution reactions of the carbenoid intermediate are favorable, and this selectivity is also attributed to conformational preferences that juxtapose the carbenoid center and imide carbonyl group. The isomunchnone dipole readily undergoes cycloaddition with several different dipolarophiles to give 1,3-dipolar cycloadducts. When acetylenic dipolarophiles were used as the trapping agents, the initial cycloadducts were found to undergo a [4 + 2]-cycloreversion, producing substituted furans in high yield. The generality of the method was demonstrated by varying the ring size of the cyclic imide. An analogous cyclization-cycloaddition reaction also occurred using diazoacetoacetyl-substituted ureas.

  DOI：

  10.1021/jo00002a058
• 作为产物：
  描述：

  N-苯基甲酰胺 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.03h， 生成 1,1-二苄基-3-苯基脲
  参考文献：
  名称：

  Synthesis of unsymmetrical phenylurea derivatives via oxidative cross coupling of aryl formamides with amines under metal-free conditions

  摘要：

  通过使用高价碘试剂作为外部氧化剂，在良好的产率下，将N-芳基甲酰胺直接转化为相应的苯基脲衍生物，通过形成异氰酸酯中间体实现。

  DOI：

  10.1039/c4nj01668h

文献信息

• A General Copper-Catalyzed Synthesis of Ynamides from 1,2-Dichloroenamides
  作者：Steven J. Mansfield、Russell C. Smith、Jonathan R. J. Yong、Olivia L. Garry、Edward A. Anderson

  DOI：10.1021/acs.orglett.9b00971

  日期：2019.4.19

  Ynamides are accessed via copper-catalyzed coupling of Grignard or organozinc nucleophiles with chloroynamides, formed in situ from 1,2-dichloroenamides. The reaction exhibits a broad substrate scope, is readily scaled, and overcomes typical limitations in ynamide synthesis such as the use of ureas, carbamates, and bulky or aromatic amide derivatives. This modular approach contrasts with previous routes

  氰化物通过格利雅（Grignard）或有机锌亲核试剂与由1,2-二氯烯酰胺原位形成的氯代乙酰胺的铜催化偶联而获得。该反应显示出广泛的底物范围，易于规模化，并且克服了在酰胺合成中的典型限制，例如使用脲，氨基甲酸酯和大体积或芳香族酰胺衍生物。这种模块化方法与以前的方法相反，它同时安装了乙酰胺的N-和C-取代基作为亲核组分。
• A robust and modular synthesis of ynamides
  作者：Steven J. Mansfield、Craig D. Campbell、Michael W. Jones、Edward A. Anderson

  DOI：10.1039/c4cc07876d

  日期：——

  A flexible, modular ynamide synthesis is reported that uses a wide range of amides and electrophiles, including acyclic carbamates, hindered sulfonamides, and aryl amides.

  报道了一种灵活、模块化的氨酰胺合成方法，使用了广泛的氨酰胺和电子亲和剂，包括无环碳酸酯、受阻磺酰胺和芳基酰胺。
• On the Thermal Dissociation of Organic Compounds. VIII. The Effects of the Substituents on the Thermal Dissociation of Tri-substituted Ureas
  作者：Teruaki Mukaiyama、Shoichiro Ozaki、Yasuhiro Kobayashi

  DOI：10.1246/bcsj.29.51

  日期：1956.1

  The rate constants of the thermal dissociation of tri-substituted ureas in fatty acids and alcohols were determined. It was shown that tri-substituted ureas dissociate faster than 1, 3-dis-substituted ureas. In tri-substituted ureas, the rates in alcohols are faster than in fatty acids in contrast with 1, 3-disubstituted ureas.Tetra-substituted ureas which are not formed by the addition reaction do not react under the same condition with tri-substituted ureas.The bimolecular mechanism for the dissociation of ureas involving the direct attack of one solvent molecule on urea was denied.

  三取代脲在脂肪酸和醇中的热解离速率常数已被测定。结果显示，三取代脲的解离速度快于1,3-二取代脲。在三取代脲中，醇中的解离速率快于脂肪酸，而1,3-二取代脲则恰恰相反。不是通过加成反应形成的四取代脲在与三取代脲的相同条件下不发生反应。否定了涉及一个溶剂分子直接攻击脲的脲解离的双分子机制。
• Visible-light-promoted oxidative desulphurisation: a strategy for the preparation of unsymmetrical ureas from isothiocyanates and amines using molecular oxygen
  作者：Ziyu Gan、Guoqing Li、Qiuli Yan、Weiseng Deng、Yuan-Ye Jiang、Daoshan Yang

  DOI：10.1039/d0gc00070a

  日期：——

  A green and efficient visible-light promoted oxidative desulphurisation protocol has been proposed for the construction of unsymmetrical ureas under mild conditions with broad substrate scope and good functional group tolerance. Most appealingly, the reaction can proceed smoothly without adding any strong oxidants. Control experiments and computational studies support a mechanism involving water-assisted

  已经提出了绿色和有效的可见光促进的氧化脱硫方案，用于在温和的条件下，具有较宽的底物范围和良好的官能团耐受性，构造不对称脲。最吸引人的是，该反应可以平稳进行，而无需添加任何强氧化剂。控制实验和计算研究支持了一种机制，该机制涉及水辅助原位生成硫脲和光催化氧化脱硫。本方法为在药物和合成化学领域中形成各种有用的不对称脲衍生物提供了有希望的合成策略。
• An efficient and mild protocol for the synthesis of unsymmetrical ureas in the absence of catalyst and additives
  作者：Rahman Hosseinzadeh、Yaghoub Sarrafi、Nora Aghili

  DOI：10.1016/j.cclet.2010.06.014

  日期：2010.10

  Abstract A new practical method for the synthesis of unsymmetrical ureas was achieved by reaction of phenylurea with primary and secondary amines under neutral and mild condition in very good yields. The reaction took place in refluxing dioxane and does not require any catalyst or additives.

  摘要在中性和温和条件下，苯脲与伯胺和仲胺反应，制得了一种合成不对称脲的实用新方法，收率很高。该反应在回流的二恶烷中进行，不需要任何催化剂或添加剂。