bis(N-tert-butoxycarbonyl-2-pyrrolyl)sulfide | 187237-63-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: bis(N-tert-butoxycarbonyl-2-pyrrolyl)sulfide
• 英文别名: Tert-butyl 2-[1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrol-2-yl]sulfanylpyrrole-1-carboxylate
• CAS: 187237-63-4
• 化学式: C₁₈H₂₄N₂O₄S
• 分子量: 364.466
• InChiKey: MOQPUMBLPWBFPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  87.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(N-tert-butoxycarbonyl-2-pyrrolyl)sulfide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到bis(N-tert-butoxycarbonyl-2-pyrrolyl)sulfone
  参考文献：
  名称：

  Synthesis and Characterization of N-t-BOC Protected Pyrrole-sulfur Oligomers And Polymers

  摘要：

  The synthesis and characterization of a new class of pyrrole-sulfur compounds is described. These compounds are designed to be precursors for an organic analogue of poly(sulfur nitride). Poly(N-t-BOC-2,5-pyrrolyl sulfide) was prepared from N-t-BOC-2,5-dibromopyrrole by first lithiating this compound with n-BuLi, followed by the addition of bis(p-tosyl) sulfide. Similarly, bis(N-t-BOC-2-pyrrolyl) sulfide was prepared starting from N-t-BOC-2-bromopyrrole. Subsequent selective oxidation with one or two equivalents of m-CPBA quantitatively gave bis(N-t-BOC-2-pyrrolyl) sulfoxide and -sulfone, respectively. Thermal deprotection of the t-BOC groups of the oligomers and the polymer resulted in decomposition of these compounds; the latter is presumably due to a combination of sulfur-extrusion and polymerization.

  DOI：

  10.1080/00397919708005026
• 作为产物：
  描述：

  1-Boc-2-溴-1H-吡咯 在 正丁基锂 、 di-p-toluenesulfonyl sulfide 作用下， 生成 bis(N-tert-butoxycarbonyl-2-pyrrolyl)sulfide
  参考文献：
  名称：

  Synthesis and Characterization of N-t-BOC Protected Pyrrole-sulfur Oligomers And Polymers

  摘要：

  The synthesis and characterization of a new class of pyrrole-sulfur compounds is described. These compounds are designed to be precursors for an organic analogue of poly(sulfur nitride). Poly(N-t-BOC-2,5-pyrrolyl sulfide) was prepared from N-t-BOC-2,5-dibromopyrrole by first lithiating this compound with n-BuLi, followed by the addition of bis(p-tosyl) sulfide. Similarly, bis(N-t-BOC-2-pyrrolyl) sulfide was prepared starting from N-t-BOC-2-bromopyrrole. Subsequent selective oxidation with one or two equivalents of m-CPBA quantitatively gave bis(N-t-BOC-2-pyrrolyl) sulfoxide and -sulfone, respectively. Thermal deprotection of the t-BOC groups of the oligomers and the polymer resulted in decomposition of these compounds; the latter is presumably due to a combination of sulfur-extrusion and polymerization.

  DOI：

  10.1080/00397919708005026

文献信息

• Synthesis and Characterization of N-<i>t</i>-BOC Protected Pyrrole-sulfur Oligomers And Polymers
  作者：L. Groenendaal、K. Pieterse、J. A.J.M. Vekemans、E. W. Meijer

  DOI：10.1080/00397919708005026

  日期：1997.1

  The synthesis and characterization of a new class of pyrrole-sulfur compounds is described. These compounds are designed to be precursors for an organic analogue of poly(sulfur nitride). Poly(N-t-BOC-2,5-pyrrolyl sulfide) was prepared from N-t-BOC-2,5-dibromopyrrole by first lithiating this compound with n-BuLi, followed by the addition of bis(p-tosyl) sulfide. Similarly, bis(N-t-BOC-2-pyrrolyl) sulfide was prepared starting from N-t-BOC-2-bromopyrrole. Subsequent selective oxidation with one or two equivalents of m-CPBA quantitatively gave bis(N-t-BOC-2-pyrrolyl) sulfoxide and -sulfone, respectively. Thermal deprotection of the t-BOC groups of the oligomers and the polymer resulted in decomposition of these compounds; the latter is presumably due to a combination of sulfur-extrusion and polymerization.