Butyl-(4-chloro-phenyl)-carbodiimide | 212687-07-5

• 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: Butyl-(4-chloro-phenyl)-carbodiimide
• CAS: 212687-07-5
• 化学式: C₁₁H₁₃ClN₂
• 分子量: 208.691
• InChiKey: KIWRCOPCJHNZTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 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：

  Butyl-(4-chloro-phenyl)-carbodiimide 在 caesium carbonate 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 (E)-4-benzyl-6-butyl-3-(4-chlorophenyl)-5-(p-tolylimino)-3,4,5,6-tetrahydro-7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
  参考文献：
  名称：

  碳二亚胺与重氮乙酸乙酯的无过渡金属级联环化一锅法合成 8-氮鸟嘌呤

  摘要：

  已经开发了一种通过级联环化过程快速组装 EDA 和碳二亚胺来构建 8-氮鸟嘌呤衍生物的简洁有效的方法。利用两种相同或不同的碳二亚胺制备了多种不同取代的 8-氮鸟嘌呤衍生物，具有优异的区域选择性和良好的收率。

  DOI：

  10.1002/ejoc.202101559
• 作为产物：
  描述：

  1-丁基-3-(4-氯苯基)脲 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 Butyl-(4-chloro-phenyl)-carbodiimide
  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

• Palladium-Catalyzed Cyclocarbonylation of <i>o</i>-Iodophenols and 2-Hydroxy-3-iodopyridine with Heterocumulenes:  Regioselective Synthesis of Benzo[<i>e</i>]-1,3-oxazin-4-one and Pyrido[3,2-<i>e</i>]-1,3-oxazin-4-one Derivatives
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/jo991256u

  日期：1999.12.1

  Benzo[e]-1,3-oxazin-2-imine-4-ones (3) were synthesized by cyclocarbonylation of o-iodophenols with carbodiimides in the presence of a catalytic amount of a palladium catalyst and 1,4-bis(diphenylphosphino)butane under CO pressure. Product yields are dependent on the nature of the substrate, catalyst, solvent, and base as well as phosphine ligand. Reaction of o-iodophenols with unsymmetrical carbodiimides affords benzo[e]-1,3-oxazin-2-imine-4-ones (11a-g) in good yield and usually in a completely regioselective manner. Benzo[e]-1,3-oxazin-2,4-diones (5) were obtained in good to excellent yields using the same procedure and a 1:2 ratio of o-iodophenol/isocyanate. Pyrido[3,2-e]-1,3-oxazin-4-ones (16) were isolated in fine yield using 2-hydroxy-3-iodopyridine instead of an iodophenol as reactant. The reaction mechanism is believed to involve in situ formation of a carbamate eater followed by palladium-catalyzed carbonylative amidation.
• 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.
• One‐Pot Synthesis of 8‐Azaguanines by Transition Metal‐Free Cascade Cyclization of Carbodiimides with Ethyl Diazoacetate
  作者：Shilong Wang、Xingchen Zhao、Jixin Liu、Ziling Zhao、Haoran Yu、Jiaxun Li、Jiazhu Li、Jinchun Chen、Zhen Zhang

  DOI：10.1002/ejoc.202101559

  日期：2022.3.29

  A concise and efficient method to construct 8-azaguanines derivatives by the rapid assembly of EDA and carbodiimides via a cascade cyclization process has been developed. A variety of diversely substituted 8-azaguanines derivatives were prepared with excellent regioselectivity and good yields utilizing two same or different carbodiimides.

  已经开发了一种通过级联环化过程快速组装 EDA 和碳二亚胺来构建 8-氮鸟嘌呤衍生物的简洁有效的方法。利用两种相同或不同的碳二亚胺制备了多种不同取代的 8-氮鸟嘌呤衍生物，具有优异的区域选择性和良好的收率。