(S)-5-chloro-3-hydroxy-3-phenylindolin-2-one | 1243153-73-2

• 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: (S)-5-chloro-3-hydroxy-3-phenylindolin-2-one
• 英文别名: (3S)-5-chloro-3-hydroxy-3-phenyl-1H-indol-2-one
• CAS: 1243153-73-2
• 化学式: C₁₄H₁₀ClNO₂
• 分子量: 259.692
• InChiKey: ZAKUKJAHRBAVGS-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (S)-5-chloro-3-hydroxy-3-phenylindolin-2-one 在 N-甲基吗啉 、 2-[氨基(二甲基)甲硅烷基]-2-甲基丙烷 、 四氯化锡 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以60%的产率得到(S)-2-amino-5-chloro-3-hydroxy-3-phenylindole
  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
• 作为产物：
  描述：

  苯基溴化镁 在 三乙基硅烷 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-5-chloro-3-hydroxy-3-phenylindolin-2-one
  参考文献：
  名称：

  [EN] 2-AMINOINDOLE COMPOUNDS AND METHODS FOR THE TREATMENT OF MALARIA
  [FR] COMPOSÉS 2-AMINOINDOLES ET MÉTHODES DE TRAITEMENT DE LA MALARIA

  摘要：

  公开号：

  WO2011053697A8

文献信息

• Rh(I)-catalyzed asymmetric addition of arylboronic acids to NH isatins
  作者：Jiangyang Gui、Guihua Chen、Peng Cao、Jian Liao

  DOI：10.1016/j.tetasy.2012.04.013

  日期：2012.4

  The transition metal-catalyzed asymmetric variant of the title reaction is normally limited to N-protected isatins. However, Rh(I)/chiral sulfoxide phosphine complexes were found to catalyze the enantioselective addition of arylboronic acids to NH isatins under mild conditions. A variety of chiral 3-aryl-3-hydroxyl-2-oxindoles were obtained with high yields and with good to excellent enantioselectivities

  标题反应的过渡金属催化的不对称变体通常限于N-保护的靛红。然而，发现在温和条件下，Rh（I）/手性亚砜膦配合物可催化将芳基硼酸对映选择性加成至NH靛红。以高收率和良好至优异的对映选择性（85-92％ee）获得了各种手性3-芳基-3-羟基-3-羟吲哚。
• Concave P-Stereogenic Phosphorodiamidite Ligands for Enantioselective Rh(I) Catalysis
  作者：Nidal Saleh、Céline Besnard、Jérôme Lacour

  DOI：10.1021/acs.orglett.4c00371

  日期：2024.3.22

  The development of a new class of concave P-stereogenic phosphorodiamidite ligands, derived from Tröger’s bases (TBs), is explored. These ligands, characterized by their remarkable stability and unique structural geometry around the P atom, are used in asymmetric Rh(I)-catalyzed additions of boronic acids to NH-isatins resulting in excellent reactivities and reasonable enantioselectivity (er up to

  探索了源自 Tröger 碱基 (TB) 的新型凹 P-立体异构亚磷酰亚胺配体的开发。这些配体具有卓越的稳定性和围绕 P 原子的独特结构几何形状，可用于 Rh(I) 催化的硼酸与 NH-靛红的不对称加成，从而产生优异的反应活性和合理的对映选择性（最高可达 92:8） 。
• Rh(I)-catalyzed asymmetric 1,2-additions of arylboronic acids to isatins with chiral sulfur–alkene hybrid ligands
  作者：Xiangqing Feng、Yanzhao Nie、Lanqiong Zhang、Jing Yang、Haifeng Du

  DOI：10.1016/j.tetlet.2014.06.074

  日期：2014.8

  A rhodium-catalyzed asymmetric 1,2-addition of arylboronic acids to isatins with chiral sulfur-alkene hybrid ligands was achieved, and a variety of 3-aryl-3-hydroxy-2-oxindoles were obtained in moderate to good yields with up to 85% ee and a biologically active compound was synthesized with this strategy. (C) 2014 Elsevier Ltd. All rights reserved.