N-(2-iodophenyl)-N-phenylmethanediimine | 1218906-34-3

• 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-(2-iodophenyl)-N-phenylmethanediimine
• 英文别名: N-(2-iodophenyl)-N'-phenyldicarbodiimide；2-iodo-N-((phenylimino)methylene)aniline
• CAS: 1218906-34-3
• 化学式: C₁₃H₉IN₂
• 分子量: 320.132
• InChiKey: UTOHHEVICPZVQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  406.1±28.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-(2-iodophenyl)-N-phenylmethanediimine 在 copper(l) iodide 、 caesium carbonate 、 L-脯氨酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 2-methyl-1-phenyl-1H-benzo[d]imidazo[1,2-a]imidazole
  参考文献：
  名称：

  区域选择性一步合成2-氨基咪唑衍生物

  摘要：

  本文描述了2-氨基咪唑衍生物的区域选择性组装的方便的单步策略。通过无过渡金属的多米诺加成/环化过程，不对称碳二亚胺与Cs 2 CO 3介导的炔丙基胺的反应在非常温和的条件下以中等至良好的收率选择性地提供了相应的多取代的2-氨基咪唑。在较高温度下，在TEA存在下，区域选择性反转。所获得的2-（邻碘芳基）氨基咪唑可以容易地转化为2-（2-联苯基）氨基咪唑，2-（邻炔基苯基）氨基咪唑，苯并咪唑并[1,2- a ]咪唑和N-（咪唑-2-基）吲哚衍生物。

  DOI：

  10.1016/j.tetlet.2019.151122
• 作为产物：
  描述：

  异氰酸苯酯 、 (2-iodophenylimino)triphenylphosphorane 以 二氯甲烷 为溶剂， 生成 N-(2-iodophenyl)-N-phenylmethanediimine
  参考文献：
  名称：

  Tandem Palladium-Catalyzed Addition/Cyclocarbonylation: An Efficient Synthesis of 2-Heteroquinazolin-4(3H)-ones

  摘要：

  A highly practical and efficient method for the synthesis of 2-heteroquinazolin-4(3H)-ones has been developed by a palladium-catalyzed tandem reaction. Under mild reaction conditions (80 degrees C, 100 psi), a wide variety of 2-heteroquinazolin-4(3H)-ones were obtained in good to excellent yields.

  DOI：

  10.1021/ol902924x

文献信息

• A concise synthesis of 4-imino-3,4-dihydroquinazolin-2-ylphosphonates via a palladium-catalyzed reaction of carbodiimide, isocyanide, and phosphite
  作者：Guanyinsheng Qiu、Yuan Lu、Jie Wu

  DOI：10.1039/c2ob26979a

  日期：——

  A palladium-catalyzed reaction of 2-iodoarylcarbodiimide, isocyanide, and phosphite leads to 4-imino-3,4-dihydroquinazolin-2-ylphosphonates in moderate to good yields. Three bonds are formed in a one pot procedure and the tandem process includes nucleophilic attack, isocyanide insertion, and C–N coupling.

  2-碘芳基碳二亚胺，异氰化物和亚磷酸酯的钯催化反应以中等至良好的产率产生4-亚氨基-3,4-二氢喹唑啉-2-基膦酸酯。一锅法过程中形成三个键，串联过程包括亲核攻击，异氰酸酯插入和C–N偶联。
• Generation of benzoimidazo[1,5-a]imidazoles via a copper-catalyzed tandem reaction of carbodiimide and isocyanoacetate
  作者：Guanyinsheng Qiu、Jie Wu

  DOI：10.1039/c2cc32135a

  日期：——

  Carbodiimide reacts with isocyanide catalyzed by copper(I) iodide, leading to benzoimidazo[1,5-a]imidazoles in good yields. This reaction is efficient, and proceeds through a formal [3+2] cycloaddition and C–N coupling.

  氨基卡宾与异氰化物在碘化铜(I)的催化下反应，生成苯并咪唑[1,5-a]咪唑类化合物，产率良好。该反应高效，通过一种形式的[3+2]环加成和C–N偶联反应进行。
• Copper-catalyzed synthesis of 2-aminobenzothiazoles from carbodiimide and sodium hydrosulfide
  作者：Weilan Zeng、Pan Dang、Xiaoyun Zhang、Yun Liang、Caiyun Peng

  DOI：10.1039/c4ra04047c

  日期：——

  An efficient copper-catalyzed method for the synthesis of a variety of 2-aminobenzothiazoles has been developed. The reaction proceeded from carbodiimide and sodium hydrosulfide via a tandem reaction in the presence of copper(II) trifluoromethanesulfonate to afford the corresponding 2-aminobenzothiazole derivatives in good to perfect yields.

  已经开发了一种有效的铜催化的合成多种2-氨基苯并噻唑的方法。该反应由碳二亚胺和氢硫化钠在三氟甲磺酸铜（II）存在下经由串联反应进行，以良好至理想的收率得到相应的2-氨基苯并噻唑衍生物。
• Facile and Selective Synthesis of Imidazobenzimidazoles<i>via</i>a Copper-Catalysed Domino Addition/Cycloisomerisation/ Coupling Process
  作者：Bingqing Xu、Bo Peng、Bili Cai、Shishi Wang、Xiaoxia Wang、Xin Lv

  DOI：10.1002/adsc.201500455

  日期：2016.2.18

  copper(I)‐catalysed domino transformation for the synthesis of tricyclic imidazobenzimidazole derivatives was developed. Using readily available primary propargylic amines and o‐haloarylcarbodiimides as the starting materials, a variety of substituted benzo[d]imidazo[1,2‐a]imidazoles was efficiently and selectively assembled. Further investigations indicated that the domino reaction was likely the result

  开发了铜（I）催化的多米诺变换，用于合成三环咪唑并苯并咪唑衍生物。使用现成的伯炔丙基胺和邻卤代芳基碳二亚胺作为起始原料，可以有效地，选择性地组装各种取代的苯并[ d ]咪唑并[1,2- a ]咪唑。进一步的研究表明，多米诺骨牌反应可能是新颖的加成/环异构化/偶联过程的结果。
• Molybdenum-mediated synthesis of quinazolin-4(3H)-ones via cyclocarbonylation using microwave irradiation
  作者：Bryan Roberts、David Liptrot、Tim Luker、Michael J. Stocks、Catherine Barber、Nicola Webb、Robert Dods、Barrie Martin

  DOI：10.1016/j.tetlet.2011.05.052

  日期：2011.7

  A new, efficient and practical synthesis of quinazolin-4(3H)-ones is reported via molybdenum-mediated cyclocarbonylation using microwave irradiation. These methods allow access to a wide range of quinazolin-4(314)-ones in reasonable yields without the need for gaseous carbon monoxide and palladium catalysts. A range of reactions illustrating the wide scope of this chemistry was carried out and all proceeded in reasonable yields. (C) 2011 Elsevier Ltd. All rights reserved.