5-chloro-3-hydroxy-3-(2-phenylethynyl)-1H-indol-2-one | 1243153-46-9

• 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: 5-chloro-3-hydroxy-3-(2-phenylethynyl)-1H-indol-2-one
• CAS: 1243153-46-9
• 化学式: C₁₆H₁₀ClNO₂
• 分子量: 283.714
• InChiKey: AABHTNMMVJWDBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-3-hydroxy-3-(2-phenylethynyl)-1H-indol-2-one 在 tert-butylammonium hexafluorophosphate(V) 、 calcium(II) trifluoromethanesulfonate 作用下， 以 neat (no solvent) 为溶剂， 反应 8.0h， 生成 (3R,4'S,7'R)-5-chloro-7'-phenyl-5'-(p-tolyl)-3a',4',7',7a'-tetrahydrospiro[indoline-3,9'-[4,7]ethanoisobenzofuran]-1',2,3'-trione
  参考文献：
  名称：

  羟吲哚衍生的1,5-炔烃的环异构化：钙（II）催化的一锅无溶剂合成苯并吡啶酮，3-（环戊二烯基）吲哚-2-酮和3-螺环吲哚-2-酮

  摘要：

  描述了在无溶剂条件下，从一锅中容易获得的3-羟基-3-（炔基）吲哚-2-酮和苯乙烯中钙催化的羟吲哚衍生的1,5-烯炔的区域选择性合成，然后进行环异构化。该方法可合成多种分子：菲啶酮，3-（环戊烯基）吲哚-2-酮和3-螺环吲哚-2-酮是通过包括交叉脱水偶联，[3,3]-σ在内的级联反应获得的重排，碳环化，异构化，氧化环重排和Diels-Alder环加成。此外，该方法具有原子经济和阶梯经济，底物范围广，产率高的特点。

  DOI：

  10.1002/adsc.201700569
• 作为产物：
  描述：

  5-氯靛红 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 生成 5-chloro-3-hydroxy-3-(2-phenylethynyl)-1H-indol-2-one
  参考文献：
  名称：

  A Concise Silylamine Approach to 2-Amino-3-hydroxy-indoles with Potent in vivo Antimalaria Activity

  摘要：

  The development of a concise strategy to access 2-amino-3-hydroxy-indoles, which are disclosed as novel antimalarials with potent in vivo activity, is reported. Starting from isatins the target compounds are synthesized in 2 steps and in good yields via oxoindole intermediates by employing tert-butyldimethylsilyl amine (TBDMSNH(2)) as previously unexplored ammonia equivalent.

  DOI：

  10.1021/ol101566h

文献信息

• Stereoselective sulfenylation of oxindole-derived propargyl alcohols to access sulfenylated-3-alkenyloxindoles
  作者：Tabassum Khan、Pallava Rajesh、Doma Arun、Srinivasarao Yaragorla

  DOI：10.1039/d1ob01921j

  日期：——

  alkenyl-sulfenylation was achieved using readily available aryl/alkyl thiols and easily prepared oxindole-derived propargyl alcohols under solvent-free conditions. The reaction proceeded with hydrogen bonding assisted regioselective α-thiolation and subsequent calcium catalyzed stereoselective alkenylation to yield E-alkenyl thioethers with high diastereoselectivity.

  在无溶剂条件下，使用容易获得的芳基/烷基硫醇和容易制备的羟吲哚衍生的炔丙醇，实现了 Ca 催化的四取代烯基亚磺酰化。该反应通过氢键辅助区域选择性α-硫醇化和随后的钙催化立体选择性烯基化进行，以产生具有高非对映选择性的E-烯基硫醚。
• A Concise Silylamine Approach to 2-Amino-3-hydroxy-indoles with Potent <i>in vivo</i> Antimalaria Activity
  作者：Sameer Urgaonkar、Joseph F. Cortese、Robert H. Barker、Mandy Cromwell、Adelfa E. Serrano、Dyann F. Wirth、Jon Clardy、Ralph Mazitschek

  DOI：10.1021/ol101566h

  日期：2010.9.17

  The development of a concise strategy to access 2-amino-3-hydroxy-indoles, which are disclosed as novel antimalarials with potent in vivo activity, is reported. Starting from isatins the target compounds are synthesized in 2 steps and in good yields via oxoindole intermediates by employing tert-butyldimethylsilyl amine (TBDMSNH(2)) as previously unexplored ammonia equivalent.
• Cycloisomerization of Oxindole-Derived 1,5-Enynes: A Calcium(II)-Catalyzed One-Pot, Solvent-free Synthesis of Phenanthridinones, 3-(Cyclopentenylidene)indolin-2-ones and 3-Spirocyclic Indolin-2-ones
  作者：Srinivasarao Yaragorla、Abhishek Pareek、Ravikrishna Dada

  DOI：10.1002/adsc.201700569

  日期：2017.9.4

  Calcium‐catalyzed regioselective synthesis of oxindole‐derived 1,5‐enynes, followed by cycloisomerization, from readily accessible 3‐hydroxy‐3‐(alkynyl)indolin‐2‐ones and styrenes in one‐pot, under solvent‐free conditions is described. This method offers the synthesis of diverse molecules: phenanthridinones, 3‐(cyclopentenylidene)indolin‐2‐ones, and 3‐spirocyclic indolin‐2‐ones are obtained through

  描述了在无溶剂条件下，从一锅中容易获得的3-羟基-3-（炔基）吲哚-2-酮和苯乙烯中钙催化的羟吲哚衍生的1,5-烯炔的区域选择性合成，然后进行环异构化。该方法可合成多种分子：菲啶酮，3-（环戊烯基）吲哚-2-酮和3-螺环吲哚-2-酮是通过包括交叉脱水偶联，[3,3]-σ在内的级联反应获得的重排，碳环化，异构化，氧化环重排和Diels-Alder环加成。此外，该方法具有原子经济和阶梯经济，底物范围广，产率高的特点。