4-bromo-N-[4-[[(4-bromophenyl)sulfonylamino]methyl]pent-4-en-2-ynyl]benzenesulfonamide | 1198357-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-N-[4-[[(4-bromophenyl)sulfonylamino]methyl]pent-4-en-2-ynyl]benzenesulfonamide
• CAS: 1198357-09-3
• 化学式: C₁₈H₁₆Br₂N₂O₄S₂
• 分子量: 548.276
• InChiKey: STFIZUAUXBTTMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-bromo-N-[4-[[(4-bromophenyl)sulfonylamino]methyl]pent-4-en-2-ynyl]benzenesulfonamide 在 gold(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到
  参考文献：
  名称：

  铑催化的炔烃头尾二聚和随后的金催化环化反应合成三取代的吡咯

  摘要：

  Abstractmagnified imageDimerization of N‐protected propargylic amines in a rather rare head‐to‐tail mode has been achieved under mild conditions with high selectivity using rhodium catalysts. The N‐protecting group could be a sulfonyl, carbamate, or carbonyl functionality and (cyclooctadiene)rhodium chloride dimer/1,1′‐bis(diphenylphosphino)ferrocene {[Rh(COD)Cl]2/dppf} as well as tris(triphenylphosphine)rhodium chloride [Rh(PPh3)3Cl] proved to be active catalysts. In addition, these functionalized gem‐enynes subsequently undergo selective gold(III)‐catalyzed intramolecular hydroamination to give trisubstituted pyrroles under mild conditions.

  DOI：

  10.1002/adsc.200800735
• 作为产物：
  描述：

  4-bromo-N-(prop-2-yn-1-yl)benzenesulfonamide 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,1'-bis(diphenylphosphino)ferrocene 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以80%的产率得到4-bromo-N-[4-[[(4-bromophenyl)sulfonylamino]methyl]pent-4-en-2-ynyl]benzenesulfonamide
  参考文献：
  名称：

  铑催化的炔烃头尾二聚和随后的金催化环化反应合成三取代的吡咯

  摘要：

  Abstractmagnified imageDimerization of N‐protected propargylic amines in a rather rare head‐to‐tail mode has been achieved under mild conditions with high selectivity using rhodium catalysts. The N‐protecting group could be a sulfonyl, carbamate, or carbonyl functionality and (cyclooctadiene)rhodium chloride dimer/1,1′‐bis(diphenylphosphino)ferrocene {[Rh(COD)Cl]2/dppf} as well as tris(triphenylphosphine)rhodium chloride [Rh(PPh3)3Cl] proved to be active catalysts. In addition, these functionalized gem‐enynes subsequently undergo selective gold(III)‐catalyzed intramolecular hydroamination to give trisubstituted pyrroles under mild conditions.

  DOI：

  10.1002/adsc.200800735

文献信息

• Synthesis of Trisubstituted Pyrroles from Rhodium-Catalyzed Alkyne Head-to-Tail Dimerization and Subsequent Gold- Catalyzed Cyclization
  作者：Hong Mei Peng、Jing Zhao、Xingwei Li

  DOI：10.1002/adsc.200800735

  日期：2009.6

  Abstractmagnified imageDimerization of N‐protected propargylic amines in a rather rare head‐to‐tail mode has been achieved under mild conditions with high selectivity using rhodium catalysts. The N‐protecting group could be a sulfonyl, carbamate, or carbonyl functionality and (cyclooctadiene)rhodium chloride dimer/1,1′‐bis(diphenylphosphino)ferrocene [Rh(COD)Cl]2/dppf} as well as tris(triphenylphosphine)rhodium chloride [Rh(PPh3)3Cl] proved to be active catalysts. In addition, these functionalized gem‐enynes subsequently undergo selective gold(III)‐catalyzed intramolecular hydroamination to give trisubstituted pyrroles under mild conditions.