3-benzyl-5-bromo-1-methylindolin-2-one | 1033201-50-1

• 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-benzyl-5-bromo-1-methylindolin-2-one
• 英文别名: 3-benzyl-5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one；3-benzyl-5-bromo-1-methyl-3H-indol-2-one
• CAS: 1033201-50-1
• 化学式: C₁₆H₁₄BrNO
• 分子量: 316.197
• InChiKey: YLDDSQXKSSOSDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-benzyl-5-bromo-1-methylindolin-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3-benzyl-5-bromo-1-methyl-2-oxoindolin-3-yl)methyl acetate
  参考文献：
  名称：

  南极念珠菌脂肪酶-B催化动力学拆分1,3-二烷基-3-羟甲基羟吲哚

  摘要：

  南极念珠菌(CAL-B) 脂肪酶催化拆分 1,3-二烷基-3-羟甲基羟甲基羟吲哚，获得 ( R )-1,3-二烷基-3-乙酰氧基甲基羟吲哚，其ee和 ( S )-1,3-二烷基-3-羟甲基羟甲基羟吲哚，具有高达 78% ee使用乙酸乙烯酯作为酰化剂和乙腈作为溶剂将 ( S )-3-烯丙基-3-羟甲基羟甲基羟吲哚转化为 ( 3S )-1'- benzyl-5-(iodomethyl)-4,5-dihydro-2 H - spiro[furan-3,3'-indolin]-2'-one。光学活性的 3-取代-3-羟甲基羟吲哚和螺-羟吲哚是合成潜在生物活性分子的关键合成子。

  DOI：

  10.1002/chir.23284
• 作为产物：
  描述：

  2,4-二溴苯胺 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 sodium hydride 、 potassium carbonate 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 3.42h， 生成 3-benzyl-5-bromo-1-methylindolin-2-one
  参考文献：
  名称：

  Rh-Catalyzed Domino Addition–Enolate Arylation: Generation of 3-Substituted Oxindoles via a Rh(lll) Intermediate

  摘要：

  A Rh-catalyzed domino conjugate addition-arylation sequence via a Rh(III) intermediate is reported. This process involving a proposed intramolecular oxidative addition of a rhodium enolate was utilized to achieve the synthesis of 3-substituted oxindole derivatives in moderate to excellent yields.

  DOI：

  10.1021/acs.orglett.5b01737

文献信息

• Asymmetric hydroxyamination of oxindoles catalyzed by chiral bifunctional tertiary aminethiourea: construction of 3-amino-2-oxindoles with quaternary stereocenters
  作者：Li-Na Jia、Jun Huang、Lin Peng、Liang-Liang Wang、Jian-Fei Bai、Fang Tian、Guang-Yun He、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1039/c1ob06413d

  日期：——

  Chiral bifunctional tertiary amine thiourea was applied to catalyze the asymmetric hydroxyamination of 3-subsituted oxindoles with nitrosobenzene to construct 3-amino-2-oxindoles with quaternary stereocenters in good yields (up to 91%) and enantioselectivities (up to 90% ee).

  应用手性双功能叔胺硫脲催化 3-取代吲哚与亚硝基苯的不对称羟基化反应，以良好的产率（高达 91%）和对映选择性（高达 90% ee）构建出具有四元立体中心的 3-氨基-2-吲哚。
• Photoinduced Dehalocyclization to Access Oxindoles Using Formate as a Reductant
  作者：Wei Ge、Jia‐Xin Wang、Ming‐Chen Fu、Yao Fu

  DOI：10.1002/cjoc.202300740

  日期：——

  Herein, we report an efficient and practical protocol for the photoinduced dehalocyclization of ortho‐halophenylacrylamides with formate by the engagement of a CO₂ radical anion to access substituted oxindoles. This method proceeds smoothly under mild conditions and exhibits a wide range of substrate as well as remarkable functional group compatibility.

  综合摘要在本文中，我们报告了一种通过 CO2 自由基阴离子啮合甲酸盐以获得取代的羰基吲哚的高效实用的光诱导原卤苯基丙烯酰胺脱卤环化方法。该方法在温和的条件下顺利进行，并具有广泛的底物范围和显著的官能团兼容性。
• Room‐Temperature Synthesis of <i>α</i>‐Alkylated Indolin‐2‐ones via a Photo Assisted Iron Catalyzed Borrowing Hydrogen Reaction
  作者：Dingguo Song、Rong Chen、Weiwei Huang、Pengtao Yang、Lingxin Chen、Jialin Zhang、Fei Ling、Weihui Zhong

  DOI：10.1002/adsc.202301219

  日期：2024.4.23

  bioorganic chemistry. Herein, we reported a visible‐light‐induced iron‐catalyzed α‐alkylation of oxindoles with alcohols to offer a variety of α‐alkylled oxindoles at room temperature. This reaction featured broad substrate scope with good functional tolerance under simple conditions. Detailed mechanistic studies has been done to illuminate the essetial role of light in this borrowing hydrogen (BH) reaction

  醇和羟吲哚衍生物是非常重要的骨架，广泛应用于有机和生物有机化学。在此，我们报道了可见光诱导的铁催化的羟吲哚与醇的α-烷基化反应，在室温下提供多种α-烷基化的羟吲哚。该反应具有底物范围广、条件简单、功能耐受性好的特点。详细的机理研究已经完成，以阐明光在这种借氢（BH）反应中的重要作用。
• A simple and eco-friendly method for the aminomethylation of 3-substituted oxindoles via three-component Mannich reaction in aqueous media
  作者：Xiong-Li Liu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1016/j.tetlet.2010.12.060

  日期：2011.2

  A simple and eco-friendly method for the aminomethylation of various 3-substituted oxindoles via three-component Mannich reaction in aqueous media has been established. A variety of oxindoles containing a quaternary carbon center, which comprises an aminomethyl group were obtained smoothly in good yields (up to 93%) with this method. Particularly valuable features, such as employing cheap and readily available formalin as a useful aminomethylation Cl unit and using water as a reaction medium, are embodied in this method. (C) 2010 Elsevier Ltd. All rights reserved.
• BF3·Et2O catalyzed allylation of oxindoles with allyl trichloroacetimidate
  作者：Jiao Ma、Ling Zhou、Jie Chen

  DOI：10.1016/j.tetlet.2015.01.155

  日期：2015.3

  An efficient Lewis acid catalyzed allylation of 3-substituted oxindoles has been developed for the first time using allyl trichloroacetimidate as an electrophile under mild reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.