N-(2-(1-(4-bromophenyl)-1-hydroxy-3-phenylprop-2-yn-1-yl)phenyl)-4-methylbenzenesulfonamide | 1238251-85-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(2-(1-(4-bromophenyl)-1-hydroxy-3-phenylprop-2-yn-1-yl)phenyl)-4-methylbenzenesulfonamide
• 英文别名: N-(2-(1-(4-bromophenyl)-1-hydroxy-3-phenylprop-2-ynyl)phenyl)-4-methylbenzenesulfonamide；N-[2-[1-(4-bromophenyl)-1-hydroxy-3-phenylprop-2-ynyl]phenyl]-4-methylbenzenesulfonamide
• CAS: 1238251-85-8
• 化学式: C₂₈H₂₂BrNO₃S
• 分子量: 532.458
• InChiKey: ITRMGXDKDLKFKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-(1-(4-bromophenyl)-1-hydroxy-3-phenylprop-2-yn-1-yl)phenyl)-4-methylbenzenesulfonamide 在 碘 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以99%的产率得到2-phenyl-4-(4-bromophenyl)-3-iodoquinoline
  参考文献：
  名称：

  Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines

  摘要：

  Highly substituted 3-iodoquinolines bearing different alkyl and aryl moieties can be synthesized in moderate to excellent yields (up to 99%) by 6-endo-dig iodocyclization of 2-tosylaminophenylprop-1-yn-3-ols with molecular iodine (I-2) under mild conditions. The cyclization is highly regioselective and the resulting 3-iodoquinolines can be further functionalized by various coupling reactions.

  DOI：

  10.1021/ol2007154
• 作为产物：
  描述：

  2-氨基-4'-溴二苯甲酮 在 吡啶 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 环己烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 5.17h， 生成 N-(2-(1-(4-bromophenyl)-1-hydroxy-3-phenylprop-2-yn-1-yl)phenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-Methylene-1-sulfonylindolin-3-ols

  摘要：

  A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.

  DOI：

  10.1021/jo301198z

文献信息

• Gold-Catalyzed Cycloisomerization Reactions of 2-Tosylaminophenylprop-1-yn-3-ols as a Versatile Approach for Indole Synthesis
  作者：Prasath Kothandaraman、Weidong Rao、Shi Jia Foo、Philip Wai Hong Chan

  DOI：10.1002/anie.201000341

  日期：2010.6.21

  A great combination: A putative indolyl‐substituted vinyl gold species generated in situ from AuCl/AgOTf catalyzed the title transformation. Under these reaction conditions, indenyl‐fused and 2,3‐disubstituted indole derivatives were produced in good to excellent yields of up to 94 % (see scheme).

  一个很好的组合：从AuCl / AgOTf原位生成的推定的吲哚基取代的乙烯基金物种催化了标题转化。在这些反应条件下，以高达94％的优良产率生产了茚并稠合的2,3-二取代的吲哚衍生物（参见方案）。
• Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (<i>Z</i>)<i>-</i>2-Methylene-1-sulfonylindolin-3-ols
  作者：Dewi Susanti、Fujiet Koh、Jeffrey Antonius Kusuma、Prasath Kothandaraman、Philip Wai Hong Chan

  DOI：10.1021/jo301198z

  日期：2012.9.7

  A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.
• Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines
  作者：Shaukat Ali、Hai-Tao Zhu、Xiao-Feng Xia、Ke-Gong Ji、Yan-Fang Yang、Xian-Rong Song、Yong-Min Liang

  DOI：10.1021/ol2007154

  日期：2011.5.20

  Highly substituted 3-iodoquinolines bearing different alkyl and aryl moieties can be synthesized in moderate to excellent yields (up to 99%) by 6-endo-dig iodocyclization of 2-tosylaminophenylprop-1-yn-3-ols with molecular iodine (I-2) under mild conditions. The cyclization is highly regioselective and the resulting 3-iodoquinolines can be further functionalized by various coupling reactions.