1,3,6,8-tetramethyl-2H,7H-[1,2,5,6]tetraselenocine[3,4-c:8,7-c']dipyrrole | 1327309-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,3,6,8-tetramethyl-2H,7H-[1,2,5,6]tetraselenocine[3,4-c:8,7-c']dipyrrole
• 英文别名: 5,7,12,14-Tetramethyl-2,3,9,10-tetraselena-6,13-diazatricyclo[9.3.0.04,8]tetradeca-1(14),4,7,11-tetraene
• CAS: 1327309-89-6
• 化学式: C₁₂H₁₄N₂Se₄
• 分子量: 502.097
• InChiKey: ODXWXTQOWGWBLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 1,3,6,8-tetramethyl-2H,7H-[1,2,5,6]tetraselenocine[3,4-c:8,7-c']dipyrrole 在 sodium hydride 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.08h， 以90%的产率得到2,7-bis(tert-butoxycarbonyl)-1,3,6,8-tetramethyl-[1,2,5,6]tetraselenocine[3,4-c:8,7-c']dipyrrole
  参考文献：
  名称：

  A convenient synthesis of pyrrolo-annelated 1,3-diselenole-2-thione and 1,3-diselenol-2-one derivatives via dipyrrolo-annelated 1,2,5,6-tetraselenocine derivatives

  摘要：

  AbstractThe reaction of 2,5‐dimethyl‐3,4‐diselenocyanato‐1H‐pyrrole by NaBH4 or NaOCH3 led to tetraselenide 7 in quantitative yield. Treatment of protected tetraselenide 8 with LiAlH4 afforded the aluminum complex intermediate that was converted into pyrrole‐annelated 1,3‐diselenolo‐2‐thione 9 in excellent yield. Similarly, treatment of tetraselenide 8 with LiAlH4 followed by TFA afforded 1,2‐diselenol intermediate that was converted into pyrrole‐annelated 1,3‐diselenolo‐2‐one 10 upon treatment of diimidazole carbonate. J. Heterocyclic Chem., (2011).

  DOI：

  10.1002/jhet.676
• 作为产物：
  描述：

  2,5-二甲基吡咯 在 sodium tetrahydroborate 、 溴 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.25h， 生成 1,3,6,8-tetramethyl-2H,7H-[1,2,5,6]tetraselenocine[3,4-c:8,7-c']dipyrrole
  参考文献：
  名称：

  A convenient synthesis of pyrrolo-annelated 1,3-diselenole-2-thione and 1,3-diselenol-2-one derivatives via dipyrrolo-annelated 1,2,5,6-tetraselenocine derivatives

  摘要：

  AbstractThe reaction of 2,5‐dimethyl‐3,4‐diselenocyanato‐1H‐pyrrole by NaBH4 or NaOCH3 led to tetraselenide 7 in quantitative yield. Treatment of protected tetraselenide 8 with LiAlH4 afforded the aluminum complex intermediate that was converted into pyrrole‐annelated 1,3‐diselenolo‐2‐thione 9 in excellent yield. Similarly, treatment of tetraselenide 8 with LiAlH4 followed by TFA afforded 1,2‐diselenol intermediate that was converted into pyrrole‐annelated 1,3‐diselenolo‐2‐one 10 upon treatment of diimidazole carbonate. J. Heterocyclic Chem., (2011).

  DOI：

  10.1002/jhet.676

文献信息

• A convenient synthesis of pyrrolo-annelated 1,3-diselenole-2-thione and 1,3-diselenol-2-one derivatives via dipyrrolo-annelated 1,2,5,6-tetraselenocine derivatives
  作者：Joon Bum Park、Ja Hong Kim、Kyukwan Zong

  DOI：10.1002/jhet.676

  日期：2011.7

  AbstractThe reaction of 2,5‐dimethyl‐3,4‐diselenocyanato‐1H‐pyrrole by NaBH4 or NaOCH3 led to tetraselenide 7 in quantitative yield. Treatment of protected tetraselenide 8 with LiAlH4 afforded the aluminum complex intermediate that was converted into pyrrole‐annelated 1,3‐diselenolo‐2‐thione 9 in excellent yield. Similarly, treatment of tetraselenide 8 with LiAlH4 followed by TFA afforded 1,2‐diselenol intermediate that was converted into pyrrole‐annelated 1,3‐diselenolo‐2‐one 10 upon treatment of diimidazole carbonate. J. Heterocyclic Chem., (2011).