1,1'-bibenzimidazolyl-2,2'-dicarboxaldehyde | 175871-66-6

• 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: 1,1'-bibenzimidazolyl-2,2'-dicarboxaldehyde
• 英文别名: 1,1'-Bi-1H-benzimidazole-2,2'-dicarbaldehyde；1-(2-formylbenzimidazol-1-yl)benzimidazole-2-carbaldehyde
• CAS: 175871-66-6
• 化学式: C₁₆H₁₀N₄O₂
• 分子量: 290.281
• InChiKey: SBDBWJUEJDCQEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-bibenzimidazolyl-2,2'-dicarboxaldehyde 在 potassium permanganate 、 sodium carbonate 作用下， 以 水 、 苯 为溶剂， 反应 10.0h， 以62%的产率得到1-(苯并咪唑-1-基)苯并咪唑
  参考文献：
  名称：

  Chiral atropisomeric five-membered biheteroaromatic diphosphines: New ligands of the bibenzimidazole and biindole series

  摘要：

  Two new chiral atropisomeric biheteroaromatic diphosphines are described: 2,2'-bis(diphenylphosphino)-1,1'-bibenzimidazole (3a) and 3,3'-dimethyl-1,1'-bis(diphenylphosphino)-2,2'-biindole (4a) structural characterization is given and configurational stability at room temperature demonstrated. The oxidation potential was recognized as a good tool to evaluate the electronic availability of the phosphorus atom in the series of biheteroaromatic diphosphines. Its value increases parallel to the electronic demand of the heterocyclic system and also depends on the position of the diphenylphosphino group. (C) 1997 Elsevier Science S.A.

  DOI：

  10.1016/s0022-328x(96)06682-x
• 作为产物：
  描述：

  2,2'-dimethyl-1,1'-bibenzimidazole 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以98%的产率得到1,1'-bibenzimidazolyl-2,2'-dicarboxaldehyde
  参考文献：
  名称：

  Chiral atropisomeric five-membered biheteroaromatic diphosphines: New ligands of the bibenzimidazole and biindole series

  摘要：

  Two new chiral atropisomeric biheteroaromatic diphosphines are described: 2,2'-bis(diphenylphosphino)-1,1'-bibenzimidazole (3a) and 3,3'-dimethyl-1,1'-bis(diphenylphosphino)-2,2'-biindole (4a) structural characterization is given and configurational stability at room temperature demonstrated. The oxidation potential was recognized as a good tool to evaluate the electronic availability of the phosphorus atom in the series of biheteroaromatic diphosphines. Its value increases parallel to the electronic demand of the heterocyclic system and also depends on the position of the diphenylphosphino group. (C) 1997 Elsevier Science S.A.

  DOI：

  10.1016/s0022-328x(96)06682-x

文献信息

• US6297387B1
  申请人：——

  公开号：US6297387B1

  公开（公告）日：2001-10-02
• US6586357B1
  申请人：——

  公开号：US6586357B1

  公开（公告）日：2003-07-01
• [EN] HETEROAROMATIC DIPHOSPHINES AS CHIRAL LIGANDS<br/>[FR] DIPHOSPHINES HETEROAROMATIQUES EN TANT QUE LIGANDS CHIRAUX
  申请人：ITALFARMACO SUD S.P.A.

  公开号：WO1996001831A1

  公开（公告）日：1996-01-25

  (EN) Chiral diphosphines constituted by an aromatic pentatomic biheterocyclic system, suitable to act as chiral ligands, complexes between said diphosphines and transition metals, and their utilization as chiral catalysts in stereocontrolled reactions, such as diastereo- and enantioselective reduction reactions. Process for the preparation of said chiral diphosphines and process for the preparation of said complexes and for their utilization as chiral catalysts in stereocontrolled reactions.(FR) On décrit des diphosphines chirales constituées par un système bihétérocyclique pentatomique aromatique, conçues pour agir en tant que ligands chiraux, des complexes entre ces diphosphines et des métaux de transition, ainsi que l'utilisation de ces substances en tant que catalyseurs chiraux dans des réactions stéréocommandées, telles que des réactions de réduction diastéréosélectives et énantiostéréosélectives. On décrit également un procédé de préparation desdites diphosphines chirales et desdits complexes, ainsi qu'un procédé d'utilisation de ces substances en tant que catalyseurs chiraux de réactions stéréocommandées.
• Chiral atropisomeric five-membered biheteroaromatic diphosphines: New ligands of the bibenzimidazole and biindole series
  作者：Tiziana Benincori、Elisabetta Brenna、Franco Sannicolò、Licia Trimarco、Patrizia Antognazza、Edoardo Cesarotti、Francesco Demartin、Tullio Pilati、Gianni Zotti

  DOI：10.1016/s0022-328x(96)06682-x

  日期：1997.2

  Two new chiral atropisomeric biheteroaromatic diphosphines are described: 2,2'-bis(diphenylphosphino)-1,1'-bibenzimidazole (3a) and 3,3'-dimethyl-1,1'-bis(diphenylphosphino)-2,2'-biindole (4a) structural characterization is given and configurational stability at room temperature demonstrated. The oxidation potential was recognized as a good tool to evaluate the electronic availability of the phosphorus atom in the series of biheteroaromatic diphosphines. Its value increases parallel to the electronic demand of the heterocyclic system and also depends on the position of the diphenylphosphino group. (C) 1997 Elsevier Science S.A.