N-((tert-butylimino)methylene)-4-nitroaniline | 1026190-86-2

• 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: N-((tert-butylimino)methylene)-4-nitroaniline
• 英文别名: N-tert-butyl-N'-(4-nitrophenyl)methanediimine；N'-tert-butyl-N-4-nitrophenyl carbodiimide
• CAS: 1026190-86-2
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: JWRUPCLMZKHBIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-((tert-butylimino)methylene)-4-nitroaniline 在 盐酸 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 16.0h， 以98%的产率得到N'-tert-butyl-N-4-nitrophenyl urea
  参考文献：
  名称：

  The efficient synthesis of carbodiimides using a titanium imido complex

  摘要：

  An efficient it synthesis of carbodiimides or ureas from the combination of a titanium imido complex 2 and a range of 12 aryl and aliphatic isocyanates is described Control experiments suggest that carbodimide formation is via heterocumulene metathesis through a transient intermediate eta(2)-ureato-N O metallacycle 8 (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.09.073
• 作为产物：
  描述：

  1-(4-硝基苯基)-1H-四唑 在 sodium azide 、 高氯酸 、 三乙胺盐酸盐 、 二甲基亚砜 作用下， 以 乙腈 为溶剂， 反应 120.0h， 生成 N-((tert-butylimino)methylene)-4-nitroaniline
  参考文献：
  名称：

  One-Pot Syntheses of 5-Amino-1-aryltetrazole Derivatives

  摘要：

  已开发出一种新颖简便的方法，将5-氨基和5-烷基氨基取代基引入到1-芳基四唑中。通过连续的开环、叠氮化和分子内环化反应，从相应的1-芳基四唑一锅获得了一系列5-氨基-1-芳基四唑。5-烷基氨基-1-芳基四唑是通过类似机制从1,4-二取代的四唑盐形成的。研究揭示了芳基取代基的性质和反应条件对中间体氨基叠氮盐分子内环化反应的区域选择性的影响。

  DOI：

  10.1055/s-2006-926403

文献信息

• Electrochemical Synthesis of Carbodiimides via Metal/Oxidant-Free Oxidative Cross-Coupling of Amines and Isocyanides
  作者：Bhanwar Kumar Malviya、Pradeep K. Jaiswal、Ved Prakash Verma、Satpal Singh Badsara、Siddharth Sharma

  DOI：10.1021/acs.orglett.0c00510

  日期：2020.3.20

  This work discloses an electrochemical oxidative cross-coupling of amines with aryl and aliphatic isocyanides. In an undivided cell, the reaction proceeds without involving any transition-metal catalyst, oxidant, or toxic reagents providing carbodiimides in good yields, thereby circumventing stoichiometric chemical oxidants, with H2 as the only byproduct. Moreover, carbodiimides were in situ converted

  这项工作公开了胺与芳基和脂族异氰酸酯的电化学氧化交叉偶联。在一个没有分隔的电池中，反应进行时不涉及任何过渡金属催化剂，氧化剂或有毒的试剂，以高收率提供了碳二亚胺，从而绕开了化学计量的化学氧化剂，其中H 2是唯一的副产物。此外，使用电开-关策略可将碳二亚胺原位转化为中等至良好收率的不对称脲。
• I₂/CHP mediated [1 + 1 + 1 + 1] cyclization of aromatic isocyanides with amines to construct 1,3-diazetidine-2,4-diimine derivatives
  作者：Hai-Feng Liu、Tong-Hao Zhu、Pei Xu、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c7ob02255g

  日期：——

  An I2/CHP (cumene hydroperoxide) mediated [1 + 1 + 1 + 1] cyclization of aromatic isocyanides with readily accessible amines via the formation 4 new C–N bonds has been developed to construct unsymmetric 1,3-diazetidine-2,4-diimine derivatives under mild conditions.

  通过形成4个新的C–N键，由I 2 / CHP（氢过氧化枯烯）介导的[1 +1 + 1 +1]环化芳香族异氰酸酯与易于获得的胺，从而构建了不对称的1,3-二氮杂啶2， 4-二亚胺衍生物在温和的条件下。
• Ultrasonic-assisted synthesis of carbodiimides from N,N′-disubstituted thioureas and ureas
  作者：Chuthamat Duangkamol、Mookda Pattarawarapan、Wong Phakhodee

  DOI：10.1007/s00706-016-1761-3

  日期：2016.11

  AbstractA facile and efficient sonochemical method for the preparation of carbodiimides from their corresponding thioureas or ureas was described. Using Ph3P–I2 combination in the presence of triethylamine, various diaryl, aryl–alkyl, as well as dialkyl substituted substrates could be converted into carbodiimides in good-to-excellent yields within short reaction times under mild conditions with simple

  摘要描述了一种从其相应的硫脲或脲制备碳二亚胺的简便有效的声化学方法。在三乙胺存在下，使用Ph 3 P–I 2组合，可以在温和的条件下，通过简单的实验设置，在短的反应时间内以良好或优异的产率将各种二芳基，芳基-烷基以及二烷基取代的底物转化为碳二亚胺。 。 图形概要
• Synthesis of Carbodiimides by I₂/CHP-Mediated Cross-Coupling Reaction of Isocyanides with Amines under Metal-Free Conditions
  作者：Tong-Hao Zhu、Shun-Yi Wang、Yang-Qing Tao、Shun-Jun Ji

  DOI：10.1021/acs.orglett.5b00722

  日期：2015.4.17

  An I-2/CHP-mediated cross-coupling reaction of isocyanides with readily accessible amines via CN formation is described for carbodiimide synthesis in moderate to excellent yields. This represents a metal-free strategy for a coupling reaction of isocyanides with amines, and it provides an efficient approach for symmetric and unsymmetric functionalized carbodiimide derivative synthesis under mild conditions
• One-Pot Syntheses of 5-Amino-1-aryltetrazole Derivatives
  作者：Andrey Vorobiov、Pavel Gaponik、Petr Petrov、Oleg Ivashkevich

  DOI：10.1055/s-2006-926403

  日期：2006.4

  A novel facile route for the introduction of 5-amino and 5-alkylamino substituents into 1-aryltetrazoles has been developed. A range of 5-amino-1-aryltetrazoles was obtained directly from the corresponding 1-aryltetrazoles in one pot by consecutive ring-opening, azidation and intramolecular cyclization. 5-Alkylamino-1-aryltetrazoles were formed by a similar mechanism from 1,4-disubstituted tetrazolium salts. An influence of the nature of aryl substituents and reaction conditions on the regioselectivity of the intramolecular cyclization of intermediate guanyl azides is revealed.

  已开发出一种新颖简便的方法，将5-氨基和5-烷基氨基取代基引入到1-芳基四唑中。通过连续的开环、叠氮化和分子内环化反应，从相应的1-芳基四唑一锅获得了一系列5-氨基-1-芳基四唑。5-烷基氨基-1-芳基四唑是通过类似机制从1,4-二取代的四唑盐形成的。研究揭示了芳基取代基的性质和反应条件对中间体氨基叠氮盐分子内环化反应的区域选择性的影响。