9-bromo-4,5-diaza-9H-fluorene | 253453-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 9-bromo-4,5-diaza-9H-fluorene
• 英文别名: 8-Bromo-3,13-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene
• CAS: 253453-36-0
• 化学式: C₁₁H₇BrN₂
• 分子量: 247.094
• InChiKey: YZUOFOHJCGGVNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-bromo-4,5-diaza-9H-fluorene 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 0.25h， 以89%的产率得到9,9'-bi-4,5-diaza-9H-fluorenylidene
  参考文献：
  名称：

  Synthesis, Structure and Chemistry of a Twisted Olefinic Bis-didentate Proligand: 5,5′-Bi-5H-cyclopenta[2,1-b : 3,4-b′]dipyridinylidene

  摘要：

  The elusive chiral twisted alkene, 5,5'-bi-5H-cyclopenta[2.1-b : 3,4-b']dipyridinylidene, known also as 9,9'-bi-4,5-diazafluorenylidene (BDAF), has been prepared in racemic form from 9-bromo-4,5-diazafluorene and from 9,9'-bi-4,5-diazafluorenyl and fully characterised. X-Ray measurements show that there is a twist of 37.8 degrees about the double bond between the 4,5-diazafluorenylidene units. A 1:1 charge-transfer compound with 7,7,8,8-tetracyanoquinodimethane (TCNQ) contains an unusual packing arrangement which is centred around the formation of spiral stacks. Each BDAF molecule contributes one 4,5-diazofluorenylidene unit to the backbone of the stack, while the second half is involved in hydrogen-bonding interactions and additional stacking with TCNQ. Examples of complexes containing the axially symmetric tetradentate ligand binding to one and to two metal ions. [M(bdaf)Cl-2] and [(MCl2)(2)(bdaf)] (M = Co, Ni, Zn), are reported.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1666::aid-hlca1666>3.0.co;2-k
• 作为产物：
  描述：

  4,5-二氮杂芴 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 苯 为溶剂， 以61%的产率得到9-bromo-4,5-diaza-9H-fluorene
  参考文献：
  名称：

  Synthesis, Structure and Chemistry of a Twisted Olefinic Bis-didentate Proligand: 5,5′-Bi-5H-cyclopenta[2,1-b : 3,4-b′]dipyridinylidene

  摘要：

  The elusive chiral twisted alkene, 5,5'-bi-5H-cyclopenta[2.1-b : 3,4-b']dipyridinylidene, known also as 9,9'-bi-4,5-diazafluorenylidene (BDAF), has been prepared in racemic form from 9-bromo-4,5-diazafluorene and from 9,9'-bi-4,5-diazafluorenyl and fully characterised. X-Ray measurements show that there is a twist of 37.8 degrees about the double bond between the 4,5-diazafluorenylidene units. A 1:1 charge-transfer compound with 7,7,8,8-tetracyanoquinodimethane (TCNQ) contains an unusual packing arrangement which is centred around the formation of spiral stacks. Each BDAF molecule contributes one 4,5-diazofluorenylidene unit to the backbone of the stack, while the second half is involved in hydrogen-bonding interactions and additional stacking with TCNQ. Examples of complexes containing the axially symmetric tetradentate ligand binding to one and to two metal ions. [M(bdaf)Cl-2] and [(MCl2)(2)(bdaf)] (M = Co, Ni, Zn), are reported.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1666::aid-hlca1666>3.0.co;2-k