methyl α,χ-diphenylallophanate | 39510-74-2

• 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: methyl α,χ-diphenylallophanate
• 英文别名: N-acetyl-N,N'-diphenylurea；1-acetyl-1,3-diphenylurea；N-acetyl-N,N'-diphenyl-urea；N-Acetyl-N,N'-diphenyl-harnstoff；N-phenyl-N-(phenylcarbamoyl)acetamide
• CAS: 39510-74-2
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: VLEBSGBTTVLWGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  methyl α,χ-diphenylallophanate 生成 异氰酸苯酯
  参考文献：
  名称：

  Busch; Blume; Pungs, Journal fur praktische Chemie (Leipzig 1954), 1909, vol. <2>79, p. 563

  摘要：

  DOI：
• 作为产物：
  描述：

  manganese triacetate 、 N,N'-二苯基硫脲 以 乙腈 为溶剂， 反应 3.0h， 以72%的产率得到methyl α,χ-diphenylallophanate
  参考文献：
  名称：

  Regioselective synthesis of N-acetylureas by manganese(III) acetate reaction of 1,3-disubstituted thioureas

  摘要：

  Reactions of asymmetrical 1,3-disubstituted thioureas with manganese(III) acetate produce regioselective N-acetylureas. A mechanism for this novel transformation is proposed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.013

文献信息

• Mild Acetylation of Amides, Thioamides, Ureas, and Thioureas Using Methyl Bis(1-naphthyl)bismuthinate in Acetic Acid
  作者：Takuji Ogawa、Kikuko Miyazaki、Hitomi Suzuki

  DOI：10.1246/cl.1990.1651

  日期：1990.9

  Amides, thioamides, ureas, and thioureas were N-acetylated in good yield with acetic acid in the presence of methyl bis(1-naphthyl)bismuthinate at room temperature.

  酰胺、硫代酰胺、脲和硫脲在室温下在双(1-萘基)铋酸甲酯存在下用乙酸以良好的收率N-乙酰化。
• Zinc Acetate-Mediated Regioselective N-Acylation of 1,3-Disubstituted Selenoureas
  作者：Xue Li、Bin Gan、Zhixiang Peng、Zhisheng Mi、Yuanyuan Xie

  DOI：10.3184/174751918x15260514562361

  日期：2018.6

  N-acetylureas were synthesised regioselectively from 1,3-disubstituted selenoureas and zinc acetate. Regioselectivity was dependent on the pKa of the amine attached to the selenourea and occurred towards the amine with the lower pKa. The approach provided a simple, mild and efficient way to construct various N-acetylureas regioselectively in moderate to good yields (53–88%). A plausible mechanism was

  N-乙酰脲是由 1,3-二取代硒脲和乙酸锌区域选择性合成的。区域选择性取决于附着在硒脲上的胺的 pKa，并且发生在 pKa 较低的胺上。该方法提供了一种简单、温和且有效的方法，可以区域选择性地构建各种 N-乙酰脲，收率中等至良好（53-88%）。提出了形成 N-乙酰脲的合理机制。
• Regioselective Acetylate of 1,3-Disubstituted Selenoureas Promoted by Recyclable Ion-Supported Hypervalent Iodine(III) Reagent
  作者：Yuanyuan Xie、Haixuan Pan

  DOI：10.1080/10426507.2013.797418

  日期：2014.1

  environmentally friendly reaction of 1,3-disubstituted selenoureas with a recyclable ion-supported hypervalent iodine(III) reagent produces regioselectively N-acetylureas. This is the first example of ion-supported hypervalent iodine reagent [dibmim]+[BF4]−being employed as an N-acetylating agent. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and

  摘要 1,3-二取代硒脲与可回收的离子负载高价碘 (III) 试剂通过温和、高效且环保的反应生成区域选择性 N-乙酰脲。这是离子支持的高价碘试剂 [dibmim]+[BF4]-用作 N-乙酰化剂的第一个例子。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Reaction of diazomethane with selenoesters
  作者：Thomas G. Back、Russell G. Kerr

  DOI：10.1016/s0040-4020(01)96714-6

  日期：1985.1

  selenoesters 1c and 1i with diazomethane resulted in crossover, with the formation of all four possible α-seleno ketones 2b, 2c, 2h and 2i. A non-concerted mechanism involving attack by the diazo compound upon the acyl carbon atom of an activated selenoester with the formation of a tetrahedral intermediate 11 has been suggested. The reaction of the selenothiocarbamate 4 with diazomethane resulted in 1,3-dipolar

  在CuI，CuSePh或Cu粉末存在下，重氮甲烷与一系列硒酸酯1的反应产生了α-（烷基-或芳基硒代）甲基酮2，产率为41-65％。副产物形成了甲基酮3和双（芳基硒代）甲烷9或14。通过与重氮甲烷的常规反应，然后用HBr溶液进行后处理，可以以高收率将硒酸酯直接转化为甲基酮。硒酸酯1c和1i与重氮甲烷的同时铜催化反应导致交叉反应，并形成了所有四种可能的α-硒酮2b，2c，2h和2i。已经提出了一种不确定的机制，该机制涉及重氮化合物对活化的硒酯的酰基碳原子的攻击并形成四面体中间体11。硒代硫代氨基甲酸酯4与重氮甲烷的反应导致1，3-偶极环加成，得到5，而不是插入到酰基-硒键中。
• One-pot synthesis of N-acylated ureas using phenyliodine (III) diacetate (PIDA) as N-acylation agent
  作者：Rong Feng、Lang Huang、Da-Bin Qin、Fang Zhou、Zhi-Bing Dong

  DOI：10.1016/j.tetlet.2023.154694

  日期：2023.9

  An effective method was explored for the one-pot synthesis of N-acylated urea derivatives by the reaction of substituted isothiocyanatobenzenes, primary amines and PIDA (phenyliodine (III) diacetate) in one-pot manner. Mild reaction conditions, short reaction time, high efficiency and readily accessible materials are the features of this method, making suitable and alternative for the preparation of

  探索了一种由取代异硫氰酸苯、伯胺和PIDA（二乙酸苯碘(III)）一锅法反应一锅法合成N-酰化脲衍生物的有效方法。该方法具有反应条件温和、反应时间短、效率高、原料易得等特点，适用于多种生物或药物活性化合物的制备。

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