N-[2-(1H-indol-3-yl)ethyl]but-3-yne-1-sulfonamide | 1452838-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-[2-(1H-indol-3-yl)ethyl]but-3-yne-1-sulfonamide
• CAS: 1452838-24-2
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: HQSNNVANEJPSKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(1H-indol-3-yl)ethyl]but-3-yne-1-sulfonamide 在 磷酸二苯酯 、 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.33h， 生成 11-(3-bromobenzyl)-11b-methyl-1,2,5,6,11,11b-hexahydro[1,2]thiazolo[2',3':1,2]pyrido[3,4-b]indole 3,3-dioxide
  参考文献：
  名称：

  Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade

  摘要：

  A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.

  DOI：

  10.1021/ol401784h
• 作为产物：
  描述：

  丁-3-炔-1-磺酰氯化 、 色胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-[2-(1H-indol-3-yl)ethyl]but-3-yne-1-sulfonamide
  参考文献：
  名称：

  Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade

  摘要：

  A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.

  DOI：

  10.1021/ol401784h

文献信息

• Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/<i>N</i>-Sulfonyliminium Cyclization Cascade
  作者：Alex W. Gregory、Pavol Jakubec、Paul Turner、Darren J. Dixon

  DOI：10.1021/ol401784h

  日期：2013.9.6

  A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.