ethyl 2-(2-benzyloxycarbonylaminophenyl)-1-methyl-1H-benzimidazole-4-carboxylate | 560086-59-1

• 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: ethyl 2-(2-benzyloxycarbonylaminophenyl)-1-methyl-1H-benzimidazole-4-carboxylate
• 英文别名: Ethyl 1-methyl-2-[2-(phenylmethoxycarbonylamino)phenyl]benzimidazole-4-carboxylate
• CAS: 560086-59-1
• 化学式: C₂₅H₂₃N₃O₄
• 分子量: 429.475
• InChiKey: URKSQCCOZRBZDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-benzyloxycarbonylaminophenyl)-1-methyl-1H-benzimidazole-4-carboxylate 在 palladium on activated charcoal manganese(IV) oxide 、 lithium aluminium tetrahydride 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 56.5h， 生成 2-(4-([1,3]dioxolan-2-yl)-1-methyl-1H-benzimidazol-2-yl)phenylamine
  参考文献：
  名称：

  Synthesis and Metalation of a Chiral, Pyridine-Strapped, Cyclic Bis(benzimidazole) Ligand

  摘要：

  [GRAPHICS]Synthesis of a chiral, strapped, cyclic bis(benzimidazole) ligand is reported. This compound forms a stable, Jahn-Teller-distorted, octahedral Cu(II) complex in which the elongated axis is positioned within the main macrocycle. The C-2-symmetric bis(benzimidazole) core adopts a highly ruffled conformation with the ortho-substituted benzene rings located anti relative to the pyridine-bearing strap.

  DOI：

  10.1021/ol049954a
• 作为产物：
  描述：

  ethyl 1-methyl-2-(2-nitrophenyl)-1H-benzimidazole-4-carboxylate 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 17.0h， 生成 ethyl 2-(2-benzyloxycarbonylaminophenyl)-1-methyl-1H-benzimidazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and Metalation of a Chiral, Pyridine-Strapped, Cyclic Bis(benzimidazole) Ligand

  摘要：

  [GRAPHICS]Synthesis of a chiral, strapped, cyclic bis(benzimidazole) ligand is reported. This compound forms a stable, Jahn-Teller-distorted, octahedral Cu(II) complex in which the elongated axis is positioned within the main macrocycle. The C-2-symmetric bis(benzimidazole) core adopts a highly ruffled conformation with the ortho-substituted benzene rings located anti relative to the pyridine-bearing strap.

  DOI：

  10.1021/ol049954a

文献信息

• [EN] STRAPPED AND MODIFIED BIS (BENZIMIDAZOLE) DIAMIDES FOR ASYMMETRIC CATALYSTS AND OTHER APPLICATIONS<br/>[FR] BIS(BENZIMIDAZOLE)DIAMIDES PONTES ET MODIFIES POUR CATALYSEURS ASYMETRIQUES ET AUTRES APPLICATIONS
  申请人：UNIV OHIO STATE RES FOUND

  公开号：WO2003057667A2

  公开（公告）日：2003-07-17

  New compounds that are similar in function to tetrapyrrole ligands are provided. The basic framework consists of three classes of homochiral cyclic bis(benzimidazole) ligands: (1) bis(benzamidazoles) having Schiff base linkages; (2) bis(benzimidazoles) with diamime linkages; and (3) bis(benzimidazoles) with diamide linkages. Complexes of these ligands are also provided. The bis(benzimidazole) ligands further comprise a strap that lessens or precludes racemization of ligands or their complexes. These homochiral ligands are useful as catalysts for many types of reactions, including asymmetric epoxidation, epoxide ring opening. Diels-Alder, hereto Diels-Alder, asymmetric oxidation of benzylic hydrocarbons, oxidation of sulfides, hydroxylation, aziridination, cyclopropanation, kinetic resolution of allenes and other cumulenes, and the addition of HCN to imines. Also provided are polymer supports comprising the homochiral bis(benzimidazole) ligands and complexes.
• Synthesis and Metalation of a Chiral, Pyridine-Strapped, Cyclic Bis(benzimidazole) Ligand
  作者：Tomasz Fekner、Judith Gallucci、Michael K. Chan

  DOI：10.1021/ol049954a

  日期：2004.3.1

  [GRAPHICS]Synthesis of a chiral, strapped, cyclic bis(benzimidazole) ligand is reported. This compound forms a stable, Jahn-Teller-distorted, octahedral Cu(II) complex in which the elongated axis is positioned within the main macrocycle. The C-2-symmetric bis(benzimidazole) core adopts a highly ruffled conformation with the ortho-substituted benzene rings located anti relative to the pyridine-bearing strap.