5-tert-butoxycarbonyl-4,6-dimethyl-2-thioxo-1,3-diselenolo[4,5-c]pyrrole | 1327309-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-tert-butoxycarbonyl-4,6-dimethyl-2-thioxo-1,3-diselenolo[4,5-c]pyrrole
• 英文别名: Tert-butyl 4,6-dimethyl-2-sulfanylidene-[1,3]diselenolo[4,5-c]pyrrole-5-carboxylate
• CAS: 1327309-97-6
• 化学式: C₁₂H₁₅NO₂SSe₂
• 分子量: 395.243
• InChiKey: QMLFCOYTHZZODF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-tert-butoxycarbonyl-4,6-dimethyl-2-thioxo-1,3-diselenolo[4,5-c]pyrrole 反应 0.33h， 以45%的产率得到4,6-dimethyl-2-oxo-5H-1,3-diselenolo[4,5-c]pyrrole
  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：

  硫光气 、 2,7-bis(tert-butoxycarbonyl)-1,3,6,8-tetramethyl-[1,2,5,6]tetraselenocine[3,4-c:8,7-c']dipyrrole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到5-tert-butoxycarbonyl-4,6-dimethyl-2-thioxo-1,3-diselenolo[4,5-c]pyrrole
  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).