2-(4-([1,3]dioxolan-2-yl)-1-methyl-1H-benzimidazol-2-yl)phenylamine | 273749-30-7

• 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: 2-(4-([1,3]dioxolan-2-yl)-1-methyl-1H-benzimidazol-2-yl)phenylamine
• 英文别名: 1-Methyl-2-(2-aminophenyl)-benzimidazole-4-carboxaldehyde ethylene acetal；Benzenamine, 2-[4-(1,3-dioxolan-2-yl)-1-methyl-1H-benzimidazol-2-yl]-；2-[4-(1,3-dioxolan-2-yl)-1-methylbenzimidazol-2-yl]aniline
• CAS: 273749-30-7
• 化学式: C₁₇H₁₇N₃O₂
• 分子量: 295.341
• InChiKey: TVDUQLKSYKKNEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  166.5-167.0 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  536.1±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-([1,3]dioxolan-2-yl)-1-methyl-1H-benzimidazol-2-yl)phenylamine 在 高氯酸 、 sodium cyanoborohydride 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 111.0h， 生成 41,42-Dimethyl-1,9,17,25,40,41,42-heptazanonacyclo[15.15.7.18,11.124,27.134,38.02,7.010,15.018,23.026,31]dotetraconta-2,4,6,8,10(15),11,13,18,20,22,24,26(31),27,29,34(40),35,37-heptadecaene
  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：

  4-([1,3]dioxolan-2-yl)-1-methyl-2-(2-nitrophenyl)-1H-benzimidazole 在 钯 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以to give 0.76 g (98%) of the title compound as a white solid的产率得到2-(4-([1,3]dioxolan-2-yl)-1-methyl-1H-benzimidazol-2-yl)phenylamine
  参考文献：
  名称：

  Cyclic bis-benzimidazole ligands and metal complexes thereof

  摘要：

  通过将(2-氨基苯基)-苯并咪唑-4-甲醛乙二醇缩醛或(2-硝基苯基)-苯并咪唑-4-苯甲醛与酸接触，可在金属或金属盐的存在下形成以下公式的环状双苯并咪唑配体。其中R1和R2可以相同或不同，并选自H、具有1至10个碳原子的烷基、苄基、取代的2-乙基苯基、羰基、苯基取代基、甲磺酰基和烷基磺酸盐基；R3和R4可以相同或不同，并选自H、甲基和乙基；R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17和R18可以相同或不同，并选自H、具有1至10个碳原子的烷基、氟、氯、溴、碘、硝基、氨基、羧酸盐、酯和苯基。

  公开号：

  US06376664B1

文献信息

• Cyclic bis-benzimidazole ligands and metal complexes thereof
  申请人：The Ohio State University

  公开号：US06376664B1

  公开（公告）日：2002-04-23

  Cyclic bis benzimidazole ligands of the following formula are formed by contacting a (2-aminophenyl)-benzimidazole-4-carboxaldehyde ethylene acetal or a (2-nitrophenyl)-benzimidazole-4-benzaldehyde with an acid optionally in the presence of a metal or a metal salt. wherein R1 and R2 may be the same or different and are selected from H, an alkyl having 1 to 10 carbon atoms, a benzyl group, a substituted 2-ethylphenyl group, a carbonyl group, a phenyl substituent, a tosyl group, and an alkylsulfonate group; R3 and R4 may be the same or different and are selected from H, methyl, and ethyl; and R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, and R18 may be the same or different and are selected from H, alkyl having 1 to 10 carbon atoms, fluoride, chloride, bromide, iodide, nitro, amino, a carboxylate, an ester, and a phenyl group.

  通过将(2-氨基苯基)-苯并咪唑-4-甲醛乙二醇缩醛或(2-硝基苯基)-苯并咪唑-4-苯甲醛与酸接触，可在金属或金属盐的存在下形成以下公式的环状双苯并咪唑配体。其中R1和R2可以相同或不同，并选自H、具有1至10个碳原子的烷基、苄基、取代的2-乙基苯基、羰基、苯基取代基、甲磺酰基和烷基磺酸盐基；R3和R4可以相同或不同，并选自H、甲基和乙基；R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17和R18可以相同或不同，并选自H、具有1至10个碳原子的烷基、氟、氯、溴、碘、硝基、氨基、羧酸盐、酯和苯基。
• US6376664B1
  申请人：——

  公开号：US6376664B1

  公开（公告）日：2002-04-23
• [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.