3-hydroxy-5-methyl-3-phenylindolin-2-one | 28864-72-4

• 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-hydroxy-5-methyl-3-phenylindolin-2-one
• 英文别名: 1,3-Dihydro-3-hydroxy-5-methyl-3-phenyl-2H-indol-2-one；3-hydroxy-5-methyl-3-phenyl-1H-indol-2-one
• CAS: 28864-72-4
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: YJKMVUSKKAWYHL-UHFFFAOYSA-N

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：
  0.13
• 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-hydroxy-5-methyl-3-phenylindolin-2-one 在 copper(l) iodide 、 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 生成 (2-氨基-5-甲基苯基)(苯基)甲酮
  参考文献：
  名称：

  Pd和Cu前驱体催化2-炔基芳基叠氮化物一锅法合成2-氨基二苯甲酮

  摘要：

  公开了一种从 2-炔基芳基叠氮化物制备 2-氨基二苯甲酮的新型一锅三步合成方法。该反应由钯催化形成 3-羟基-3-苯基吲哚-2-酮，随后酰胺键水解和铜催化脱羧生成 2-氨基二苯甲酮。在温和的反应条件下以中等至良好的产率得到所需产物。

  DOI：

  10.1002/ejoc.202100772
• 作为产物：
  描述：

  5-methyl-3-phenyloxindole 在 air 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以73%的产率得到3-hydroxy-5-methyl-3-phenylindolin-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

• A catalytic metal-free Ritter reaction to 3-substituted 3-aminooxindoles
  作者：Feng Zhou、Miao Ding、Jian Zhou

  DOI：10.1039/c2ob25319d

  日期：——

  The first Ritter reaction of 3-substituted 3-hydroxyoxindoles with nitriles, catalyzed by HClO4, is developed, which enables the synthesis of 3-substituted 3-aminooxindoles in good to excellent yield with rich diversity.

  HClO 4催化了3-取代的3-羟基羟吲哚与腈的第一个Ritter反应，该反应使得合成3-取代的3-氨基氧吲哚具有良好的收率和丰富的多样性。
• Lewis Acid-Catalyzed Enantioselective Hydroxylation Reactions of Oxindoles and β-Keto Esters Using DBFOX Ligand
  作者：Takehisa Ishimaru、Norio Shibata、Jun Nagai、Shuichi Nakamura、Takeshi Toru、Shuji Kanemasa

  DOI：10.1021/ja0668825

  日期：2006.12.1

  enantioselective hydroxylation reaction of both 3-aryl and 3-alkyl-2-oxindoles using the DBFOX-Zn(II) complex, leading to pharmaceutically important chiral 3-hydroxy-2-oxindoles was described. The structure of oxidant was found to play an important role to increase the enantioselectivity. The methodology has successfully applied to the highly enantioselective hydroxylation of beta-keto esters using the DBFOX-Ni(II)

  描述了使用 DBFOX-Zn(II) 配合物对 3-芳基和 3-烷基-2-羟吲哚进行的第一次催化对映选择性羟基化反应，产生了具有药学意义的手性 3-羟基-2-羟吲哚。发现氧化剂的结构在提高对映选择性方面起着重要作用。该方法已成功应用于使用 DBFOX-Ni(II) 配合物对 β-酮酯进行高度对映选择性羟基化。
• Organocatalytic stereoselective conjugate addition of 3-substituted oxindoles with in situ generated ortho-quinone methides
  作者：Weihong Liang、Wenhao Yin、Tingzhong Wang、Fayang G. Qiu、Junling Zhao

  DOI：10.1016/j.tetlet.2018.03.069

  日期：2018.5

  A novel method for the stereoselective conjugate addition of 3-substituted oxindoles to in situ generated o-QMs was described. This process was catalyzed efficiently by a cinchonidine-derived squaramide catalyst in oil-water phase, furnishing the corresponding 3,3-disubsituted oxindole derivatives in moderate to high yields (up to 98%) with high stereoselectivities (up to 95% ee, 15.4:1 dr). The utility

  描述了一种将3-取代的羟吲哚立体选择性共轭加成到原位生成的o -QMs的新方法。该方法在油水相中由辛可尼定衍生的方酰胺催化剂有效地催化，以中等至高收率（高达98％）和高的立体选择性（高达95％ee，15.4）提供了相应的3,3-二取代的羟吲哚衍生物。 ：1博士）。还通过克级合成和一种产物的衍生化研究了该反应的效用。
• Facile Synthesis of Enantioenriched C^γ-Tetrasubstituted α-Amino Acid Derivatives via an Asymmetric Nucleophilic Addition/Protonation Cascade
  作者：Shu-Wen Duan、Jing An、Jia-Rong Chen、Wen-Jing Xiao

  DOI：10.1021/ol200550y

  日期：2011.5.6

  An asymmetric nucleophilic addition/protonation reaction of 3-substituted oxindoles and ethyl 2-phthalimidoacrylate has been described. This strategy can give direct access to Cγ-tetrasubstituted α-amino acid derivatives bearing 1,3-nonadjacent stereocenters with up to 98% yield, 94:6 dr, and >99% ee. Dual activation is proposed in the transition state, and the opposite enantiomers can be obtained

  已经描述了3-取代的羟吲哚和2-邻苯二甲酰亚胺基丙烯酸乙酯的不对称亲核加成/质子化反应。这种策略可以给予至C直接访问γ -tetrasubstitutedα氨基酸衍生物轴承1,3-不相邻的立体中心具有高达98％的收率，94：6 DR，和> 99％ee的。提出了在过渡态下的双重活化，并且可以简单地通过将辛可尼丁衍生的催化剂改变为辛可宁类似物来获得相反的对映异构体。
• 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。