methyl 2-amino-1-isopropyl-1H-benzo[d]imidazole-5-carboxylate | 1329120-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: methyl 2-amino-1-isopropyl-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: Methyl 2-amino-1-propan-2-ylbenzimidazole-5-carboxylate
• CAS: 1329120-08-2
• 化学式: C₁₂H₁₅N₃O₂
• 分子量: 233.27
• InChiKey: CCVVQUDVXISXAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-amino-1-isopropyl-1H-benzo[d]imidazole-5-carboxylate 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 24.08h， 生成 methyl 4-phenyl-6-(propan-2-yl)-2,3,3a,4,6,11a-hexahydrofuro[3',2':5,6]pyrimido[1,2-a]benzimidazole-9-carboxylate
  参考文献：
  名称：

  碱催化的Povarov反应：对二氢嘧啶基苯并咪唑的不寻常的[1,3]σ重排。

  摘要：

  已开发出一种新颖的碱催化的芳基胺，醛和缺电子的亲二烯体的Povarov反应。还发现了导致4,10-二氢嘧啶基[1,2- a ]苯并咪唑的前所未有的原位[1,3]σ重排。X射线晶体研究讨论并支持了对可能机制的见解。在微波条件下，在可溶性载体上以单锅多组分方式实现该级联反应。

  DOI：

  10.1021/ol201985p
• 作为产物：
  描述：

  4-异丙基氨基-3-硝基苯甲酸甲酯 在 甲酸铵 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 methyl 2-amino-1-isopropyl-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  铜催化的好氧氧化环化和酮化：一锅合成苯并咪唑并[1,2-a]咪唑啉酮

  摘要：

  在有氧条件下，通过2-氨基苯并咪唑，醛和末端炔的新型5 - exo -dig环化-酮化级联反应，高效合成了苯并咪唑并[1,2- a ]咪唑酮。

  DOI：

  10.1039/c6cc01828a

文献信息

• Three Component Divergent Reactions: Base-Controlled Amphiphilic Synthesis of Benzimidazole-Linked Thiazetidines and Fused Thiadiazines
  作者：Manikandan Selvaraju、Sandip Dhole、Chung-Ming Sun

  DOI：10.1021/acs.joc.6b01586

  日期：2016.10.7

  A divergent reaction of 2-aminobenzimidazole with isothiocyanates and dihalomethanes has been developed for the selective synthesis of benzoimidazothiazetidine and benzoimidazothiadiazine. A single-pot reaction of 2-aminobenzimidazole in the presence of sodium hydride delivers benzoimidazothiazetidine, whereas triethylamine promotes the formation of benzoimidazothiadiazine via a sequential stepwise, fashion. The reaction sequence involves the initial formation of thiourea followed by regioselective nucleophilic addition and intramolecular ring-closing with dihalo electrophiles. The observed regioselectivity,of this reaction is governed by the nature of bases and the reaction sequence.
• One-Pot, Two-Step Synthesis of Imidazo[1,2-<i>a</i>]benzimidazoles via A Multicomponent [4 + 1] Cycloaddition Reaction
  作者：Ya-Shan Hsiao、Bharat D. Narhe、Ying-Sheng Chang、Chung-Ming Sun

  DOI：10.1021/co400075z

  日期：2013.10.14

  A one-pot, two-step synthesis of imidazo[1,2-a]benzimidazoles has been achieved by a three-component reaction of 2-aminobenzimidazoles with an aromatic aldehyde and an isocyanide. The reaction involving condensation of 2-aminobenzimidazole with an aldehyde is run under microwave activation to generate an imine intermediate under basic conditions which then undergoes [4 + 1] cycloaddition with an isocyanide.
• [EN] NOVEL BENZIMIDAZOLE COMPOUND, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] NOUVEAU COMPOSÉ DE BENZIMIDAZOLE, SON PROCÉDÉ DE PRÉPARATION ET COMPOSITION PHARMACEUTIQUE LE CONTENANT
  申请人：CRYSTALGENOMICS INC

  公开号：WO2011099832A2

  公开（公告）日：2011-08-18

  The present invention relates to a novel benzimidazole compound, a pharmaceutical composition for preventing or treating an inflammatory disease comprising said compound, a use of a novel benzimidazole compound for the manufacture of a medicament for preventing or treating an inflammatory disease, and a method of preventing or treating an inflammatory disease in a mammal comprising administering to the mammal said compound.
• Copper catalyzed aerobic oxidative cyclization and ketonization: one pot synthesis of benzoimidazo[1,2-a]imidazolones
  作者：Manikandan Selvaraju、Tzuen-Yang Ye、Chia-Hsin Li、Pei-Heng Ho、Chung-Ming Sun

  DOI：10.1039/c6cc01828a

  日期：——

  A highly efficient synthesis of benzoimidazo[1,2-a]imidazolone through a novel oxidative 5-exo-dig cyclization-ketonization cascade of 2-aminobenzimidazole, aldehyde and terminal alkyne has been explored under aerobic conditions.

  在有氧条件下，通过2-氨基苯并咪唑，醛和末端炔的新型5 - exo -dig环化-酮化级联反应，高效合成了苯并咪唑并[1,2- a ]咪唑酮。
• Base-Catalyzed Povarov Reaction: An Unusual [1,3] Sigmatropic Rearrangement to Dihydropyrimidobenzimidazoles
  作者：Chih-Hau Chen、Gorakh S. Yellol、Po-Tsung Lin、Chung-Ming Sun

  DOI：10.1021/ol201985p

  日期：2011.10.7

  A novel base-catalyzed Povarov reaction of arylamines, aldehydes, and electron-deficient dienophiles has been developed. An unprecedented in situ [1,3] sigmatropic rearrangement leading to 4,10-dihydropyrimido[1,2-a]benzimidazoles has also been discovered. An insight of the plausible mechanism is discussed and supported by X-ray crystal study. This cascade reaction is achieved in a one-pot multicomponent

  已开发出一种新颖的碱催化的芳基胺，醛和缺电子的亲二烯体的Povarov反应。还发现了导致4,10-二氢嘧啶基[1,2- a ]苯并咪唑的前所未有的原位[1,3]σ重排。X射线晶体研究讨论并支持了对可能机制的见解。在微波条件下，在可溶性载体上以单锅多组分方式实现该级联反应。