N-n-butyl-N'-phenylcarbodiimide | 21848-95-3

• 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: N-n-butyl-N'-phenylcarbodiimide
• 英文别名: N-((butylimino)methylene)aniline；N-butyl-N'-phenylmethanediimine；N-butyl-N'-phenylcarbodiimide；N-phenyl-N'-(n-butyl)carbodiimide；N-butyl-N'-phenylcarbodiimiide
• CAS: 21848-95-3
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: UHZVBFGPKDZMLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-n-butyl-N'-phenylcarbodiimide 在 三甲基乙炔基硅 作用下， 以 苯 为溶剂， 反应 72.0h， 以10%的产率得到5-(n-butylamino)-1-phenyltetrazole
  参考文献：
  名称：

  Reactions of trimethylsilyl azide with heterocumulenes

  摘要：

  DOI：

  10.1021/jo01313a021
• 作为产物：
  描述：

  N-butyl-N'-phenylurea 在 三乙胺 、 二溴三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-n-butyl-N'-phenylcarbodiimide
  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

文献信息

• A New Synthetic Protocol for the Preparation of Carbodiimides Using a Hypervalent Iodine(III) Reagent
  作者：Yunyang Wei、Chenjie Zhu、Dan Xu

  DOI：10.1055/s-0030-1258414

  日期：2011.3

  A new, simple, and efficient preparation of symmetrical and unsymmetrical carbodiimides from the corresponding thioureas via dehydrosulfurization using a hypervalent iodine(III) reagent is described. The oxidation afforded carbodiimides in excellent yields and high selectivity. A possible mechanism for the transformation is proposed. desulfurization - hypervalent iodine - oxidations - carbodiimides

  描述了一种通过使用高价碘（III）试剂通过脱硫反应从相应的硫脲中制备对称和不对称碳二亚胺的新方法，该方法简单有效。该氧化以优异的产率和高选择性提供了碳二亚胺。提出了一种可能的转换机制。 脱硫-高价碘-氧化-碳二亚胺-催化
• Palladium-catalyzed cross-coupling reaction of azides with isocyanides
  作者：Zhen Zhang、Zongyang Li、Bin Fu、Zhenhua Zhang

  DOI：10.1039/c5cc05981j

  日期：——

  A palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides.

  一种钯催化的偶联反应方法已经开发出来，可以将叠氮化合物与异氰酸酯进行偶联，从而提供了一种合成非对称碳二亚胺的通用途径。
• o-Iodoxybenzoic Acid Mediated Oxidative Desulfurization of 1,3-Disubstituted Thioureas to Carbodiimides
  作者：Krishnacharya Akamanchi、Pramod Chaudhari、Prasad Dangate

  DOI：10.1055/s-0030-1259072

  日期：2010.12

  An efficient and mild oxidative desulfurization procedure using o-iodoxybenzoic acid has been developed for the synthesis of carbodiimides starting from easily synthesizable 1,3-disubstituted thioureas.

  已经开发了一种使用邻碘苯甲酸的高效温和的氧化脱硫程序，用于从易于合成的 1,3-二取代硫脲开始合成碳二亚胺。
• Di-2-Pyridyl thionocarbonate. A new reagent for the preparation of isothiocyanates and carbodiimides.
  作者：Sunggak Kim、Kyu Yang Yi

  DOI：10.1016/s0040-4039(00)98578-2

  日期：1985.1

  Reaction of amines with di-2-pyridyl thionocarbonate affords the corresponding isothiocyanates at room temperature, while reaction of N,N′-disubstituted thio-ureas with di-2-pyridyl thionocarbonate in the presence of 4-dimethylaminopyridine as a catalyst affords the corresponding carbodiimides in high yields.

  胺与二-2-吡啶基硫代碳酸酯在室温下反应可得到相应的异硫氰酸酯，而N，N'-二取代硫脲与二-2-吡啶基硫代碳酸酯在4-二甲基氨基吡啶存在下的反应可得到相应的异硫氰酸酯。碳二亚胺的收率很高。
• A Catalytic Route to Pyrrole Derivatives <i>via</i> Copper‐catalyzed Multicomponent Reaction
  作者：Alireza Samzadeh‐Kermani、Samira Ghasemi

  DOI：10.1002/jhet.3614

  日期：2019.8

  A novel approach for the synthesis of pyrrole derivatives has been reported. The reactions starting from terminal alkynes, carbodiimides, and malononitrile using CuI, DBU, and TBPAc in anhydrous MeCN afforded the functionalized pyrroles in acceptable yields. Alkyl‐, aryl‐, and heteroaromatic terminal alkynes were tolerated. Carbodiimides could be symmetrical and unsymmetrical substrates with aryl or

  已经报道了合成吡咯衍生物的新方法。使用CuI，DBU和TBPAc在无水MeCN中从末端炔烃，碳二亚胺和丙二腈开始的反应以可接受的收率提供了官能化的吡咯。烷基，芳基和杂芳族末端炔烃是可以容忍的。碳二亚胺可以是具有芳基或烷基取代基的对称和不对称底物。当使用不对称的碳二亚胺时，该反应表现出良好的区域选择性。