3-(2'-methylphenyl)-3-hydroxy-1,3-dihydro-indol-2-one | 20423-57-8

• 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: 3-(2'-methylphenyl)-3-hydroxy-1,3-dihydro-indol-2-one
• 英文别名: 3-hydroxy-3-o-tolyl-indolin-2-one；3-Hydroxy-3-o-tolyl-indolin-2-on；(+/-)-3-Hydroxy-3-(o-tolyl)-indolin-2-on；3-o-Tolyl-dioxindol；3-hydroxy-3-(2-methylphenyl)-1H-indol-2-one
• CAS: 20423-57-8
• 化学式: C₁₅H₁₃NO₂
• mdl: MFCD25294654
• 分子量: 239.274
• InChiKey: FICSQISOWVCKIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  229.7 °C (decomp)
• 沸点：
  468.4±45.0 °C(predicted)
• 密度：
  1.279±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  3-(2'-methylphenyl)-3-hydroxy-1,3-dihydro-indol-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 、 二氯甲烷 为溶剂， 反应 1.0h， 以53%的产率得到2-Amino-3-(o-tolyl)indol-3-ol
  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：

  3-(o-tolyl)indolin-2-one 在 air 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以49%的产率得到3-(2'-methylphenyl)-3-hydroxy-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed α-Arylation of Oxindoles with Aryl Chlorides and Aerobic Oxidation of the Products in a One-Pot Procedure

  摘要：

  NHC-Pd(II)-Im complex 1 was found to be an effective catalyst for the alpha-arylation of unprotected oxindoles with aryl chlorides to give products 4 in 44-98% yields under a N-2 atmosphere. Furthermore, if the reactions were first performed under conditions identical to those for the alpha-arylation reaction for 12 hand then exposed to air for another 3 h, 3-aryl-3-hydroxy-2-oxindoles 5 can be obtained in 49-84% yields In a one-pot procedure.

  DOI：

  10.1021/ol400186b

文献信息

• Rhodium-Catalyzed Addition of Arylboronic Acids to Isatins:  An Entry to Diversity in 3-Aryl-3-Hydroxyoxindoles
  作者：Patrick Y. Toullec、Richard B. C. Jagt、Johannes G. de Vries、Ben L. Feringa、Adriaan J. Minnaard

  DOI：10.1021/ol0608101

  日期：2006.6.1

  [reaction: see text] A general method for the catalytic 1,2-addition of aryl and alkenyl boronic acids to isatins is described using a rhodium(I)/triphenylphosphite catalyst. The application of this transformation allows the synthesis of a variety of 3-aryl-3-hydroxyoxindole building blocks in high yields. An enantioselective version of this reaction using a rhodium(I)/phosphoramidite system is also

  [反应：见正文]描述了使用铑（I）/亚磷酸三苯酯催化剂将芳基和烯基硼酸催化1，2-加成至靛红的一般方法。该转化的应用允许以高收率合成各种3-芳基-3-羟基恶吲哚结构单元。还提出了使用铑（I）/亚磷酰胺体系的该反应的对映选择性形式。
• Palladium-Catalyzed Asymmetric Benzylation of 3-Aryl Oxindoles
  作者：Barry M. Trost、Lara C. Czabaniuk

  DOI：10.1021/ja1079755

  日期：2010.11.10

  we report palladium-catalyzed asymmetric benzylic alkylation with 3-aryl oxindoles as prochiral nucleophiles. Proceeding analogously to asymmetric allylic alkylation, asymmetric benzylation occurs in high yield and enantioselectivity for a variety of unprotected 3-aryl oxindoles and benzylic methyl carbonates using chiral bisphosphine ligands. This methodology represents a novel asymmetric carbon-carbon

  在这里，我们报告了钯催化的不对称苄基烷基化，以 3-芳基羟吲哚作为前手性亲核试剂。与不对称烯丙基烷基化类似地进行，使用手性双膦配体对各种未保护的 3-芳基羟吲哚和苄基甲基碳酸酯以高产率和对映选择性发生不对称苄化。该方法代表在苄基和前手性亲核试剂之间形成新的不对称碳-碳键以生成季中心。
• ArPNO-catalyzed acylative kinetic resolution of tertiary alcohols: access to 3-hydroxy-3-substituted oxindoles
  作者：Min Yang、Yu-Lin Gao、Ming-Sheng Xie、Hai-Ming Guo

  DOI：10.1039/d2ob01205g

  日期：——

  Bifunctional chiral 4-aryl-pyridine-N-oxides (ArPNO) were reported for the acylative kinetic resolution of 3-hydroxy-3-substituted oxindoles, where the oxygen acts as the nucleophilic site. Using less sterically hindered acetic anhydride, both the recovered tertiary heterocyclic alcohols and the ester products exhibited good to excellent results with s-factors up to 167. Control experiments supported

  据报道，双功能手性 4-芳基-吡啶-N-氧化物 (ArPNO) 用于 3-羟基-3-取代的羟吲哚的酰化动力学拆分，其中氧充当亲核位点。使用较少空间位阻的乙酸酐，回收的叔杂环醇和酯产物都表现出良好至优异的结果，s因子高达 167。对照实验支持双重活化方式，其中N-氧化物基团和 N-H 质子在ArPNO 对于高选择性和增强催化反应性至关重要。与广泛使用的手性 NHC、异硫属元素脲和 DMAP 催化剂相比，我们发现手性 ArPNO 在叔醇的动力学拆分中也是有效的有机催化剂。
• Synthesis of Sulfur-Containing Oxindoles by Photoinduced Alkene Difunctionalization via Sulfur 1,2-Relocation
  作者：Cong Lu、Rui Chen、Rui Wang、Dong Jing、Ke Zheng

  DOI：10.1021/acs.orglett.2c04189

  日期：2023.2.10

  which have been widely applied in agrochemicals and pharmaceuticals. Herein, a new approach for the efficient construction of sulfur-containing oxindoles by photoinduced alkene difunctionalization via sulfur 1,2-relocation is developed. The method exhibited a high functional group tolerance and broad substrate compatibility. A library of sulfur-containing oxindole derivatives were synthesized under mild

  有机硫化合物广泛存在于各种天然产物中，广泛应用于农药和医药领域。在此，开发了一种通过硫 1,2-重定位光诱导烯烃双官能化有效构建含硫羟吲哚的新方法。该方法表现出高官能团耐受性和广泛的底物相容性。在温和条件下（无金属、无光催化剂和无添加剂）合成了一个含硫羟吲哚衍生物库。机理研究表明，这种光化学过程是由羟吲哚烯醇化物与氧化还原活性酯形成 EDA 复合物引发的，β-硫基自由基的 C-S 键裂解原位生成烯烃是该过程的关键步骤转型。
• COAP/Pd-Catalyzed Linear Asymmetric Allylic Alkylation for Optically Active 3,3-Disubstituted Oxindole Derivatives with a Four-Carbon Amino Side Chain
  作者：Wen-Kai Liu、Bai-Lin Wang、Sheng-Suo Zhou、Jun-Hao Shen、Zheng Wang、Xing-Wang Wang

  DOI：10.1021/acs.orglett.2c03902

  日期：2023.1.13

  An asymmetric linear selective allylic alkylation of vinylaziridines with 3-aryl oxindoles has been developed by using a chiral oxamide-phosphine (COAP-Bn-OMe-p)/palladium complex in methanol, which furnished a wide variety of 3,3-disubstituted oxindole derivatives in good yields with excellent regio- and enantioselectivities.

  通过在甲醇中使用手性草酰胺-膦 (COAP-Bn-OMe- p )/钯络合物，开发了乙烯基氮丙啶与 3-芳基羟吲哚的不对称线性选择性烯丙基烷基化反应，可提供多种 3,3-二取代羟吲哚具有良好区域选择性和对映选择性的高收率衍生物。