5,10-bis(dimethylamino)-3,8-bis(trimethylstannyl)-5H,10H-dipyrrolo{1,2-a:1',2'-d}-pyrazine | 146830-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯嗪
• 英文名称: 5,10-bis(dimethylamino)-3,8-bis(trimethylstannyl)-5H,10H-dipyrrolo{1,2-a:1',2'-d}-pyrazine
• 英文别名: (2S,8R)-2-N,2-N,8-N,8-N-tetramethyl-6,12-bis(trimethylstannyl)-1,7-diazatricyclo[7.3.0.03,7]dodeca-3,5,9,11-tetraene-2,8-diamine
• CAS: 146830-88-8
• 化学式: C₂₀H₃₆N₄Sn₂
• 分子量: 569.953
• InChiKey: WMSWHBGQUQUZIF-HZLDOYPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  16.34
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5,10-bis(dimethylamino)-3,8-bis(trimethylstannyl)-5H,10H-dipyrrolo{1,2-a:1',2'-d}-pyrazine 、 水 在 methyl iodide 作用下， 以 乙腈 为溶剂， 以20%的产率得到5-trimethylstannyl-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Group 14 metalated 6-amino-1-azafulvene dimers. Evidence for a double intramolecular nitrogen-tin interaction

  摘要：

  The structures of group 14 C-metalated 6-amino-1-azafulvene dimers have been investigated in solution and in the solid state by NMR spectroscopy. For one of these compounds, 5,10-bis(dimethylamino)-3,8-bis(trimethylstannyl)-5H,10H-dipyrrolo[1,2-a:1',2'-d]-pyrazine (2c), the molecular structure in the solid state has been determined by X-ray diffractometry. The two tin centers have a distorted-trigonal-bipyramidal coordination geometry with the more electronegative N ligand at a pseudoaxial position, resulting in one of the longest known Sn-N interactions: 3.101 (5) angstrom. Moreover, the temperature-dependent C-13 CP-MAS NMR spectrum of this compound shows an appreciable narrowing of the Me3Sn signal between 296 and 333 K. By comparison with nonmetalated analogs or with isomer 5c, the nonreactivity of compound 2c toward hydrolytic decomposition into correspondings-(trimethylstannyl)-pyrrole-2-carbaldehyde (3c) may be the result of stabilization of the dimeric form 2c by a double Sn-N interaction. In silicon and germanium analogs (2a, 2b) the Si(Ge)-N interaction is weaker.

  DOI：

  10.1021/om00028a011
• 作为产物：
  描述：

  三甲基氯化锡 、 trans-5,10-bis-(dimethylamino)-5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine 在 n-butyllithium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 5,10-bis(dimethylamino)-3,8-bis(trimethylstannyl)-5H,10H-dipyrrolo{1,2-a:1',2'-d}-pyrazine
  参考文献：
  名称：

  Group 14 metalated 6-amino-1-azafulvene dimers. Evidence for a double intramolecular nitrogen-tin interaction

  摘要：

  The structures of group 14 C-metalated 6-amino-1-azafulvene dimers have been investigated in solution and in the solid state by NMR spectroscopy. For one of these compounds, 5,10-bis(dimethylamino)-3,8-bis(trimethylstannyl)-5H,10H-dipyrrolo[1,2-a:1',2'-d]-pyrazine (2c), the molecular structure in the solid state has been determined by X-ray diffractometry. The two tin centers have a distorted-trigonal-bipyramidal coordination geometry with the more electronegative N ligand at a pseudoaxial position, resulting in one of the longest known Sn-N interactions: 3.101 (5) angstrom. Moreover, the temperature-dependent C-13 CP-MAS NMR spectrum of this compound shows an appreciable narrowing of the Me3Sn signal between 296 and 333 K. By comparison with nonmetalated analogs or with isomer 5c, the nonreactivity of compound 2c toward hydrolytic decomposition into correspondings-(trimethylstannyl)-pyrrole-2-carbaldehyde (3c) may be the result of stabilization of the dimeric form 2c by a double Sn-N interaction. In silicon and germanium analogs (2a, 2b) the Si(Ge)-N interaction is weaker.

  DOI：

  10.1021/om00028a011