1,3-dibenzyl-3-hydroxy-1,3-dihydro-2H-indol-2-one | 35887-49-1

• 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: 1,3-dibenzyl-3-hydroxy-1,3-dihydro-2H-indol-2-one
• 英文别名: 1,3-dibenzyl-3-hydroxy-2-oxo-2,3-dihydroindole；1,3-dibenzyl-3-hydroxyindolin-2-one；3-hydroxy-1,3-dibenzylindolin-2-one；1,3-dibenzyl-3-hydroxy-1,3-dihydro-indol-2-one；1,3-Dibenzyl-3-hydroxyindol-2-one
• CAS: 35887-49-1
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: CBJUGMFUMAIKKI-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177 °C(Solv: benzene (71-43-2))
• 沸点：
  589.4±50.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dibenzyl-3-hydroxy-1,3-dihydro-2H-indol-2-one 在 盐酸 、 tin(ll) chloride 作用下， 以 水 、 溶剂黄146 为溶剂， 以53%的产率得到1,3-dibenzyl-1,3-dihydroindol-2-one
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalysed Oxygen-to-Carbon Carboxyl Transfer of Indolyl and Benzofuranyl Carbonates

  摘要：

  研究了N-杂环卡宾在一系列吲哚基和苯并呋喃基碳酸酯上促进O到C羧基转移的能力，并阐明了该过程的范围和局限性。

  DOI：

  10.1055/s-2008-1077890
• 作为产物：
  描述：

  1,3-dibenzyl-4-hydroxy-2(1H)-quinolone 在 过氧乙酸 、 氢氧化钾 、 air 作用下， 以 苯 为溶剂， 反应 43.0h， 生成 1,3-dibenzyl-3-hydroxy-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Novel Ring Contraction of 3-Hydroxy-2,4(1H,3H)-quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls

  摘要：

  Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.

  DOI：

  10.1021/jo015786d

文献信息

• The Power of Triplet and Singlet Oxygen in Synthesis: 2-Oxindoles, 3-Hydroxy-2-oxindoles, and Isatins from Furans
  作者：Myron Triantafyllakis、Kalliopi Sfakianaki、Dimitris Kalaitzakis、Georgios Vassilikogiannakis

  DOI：10.1021/acs.orglett.8b01404

  日期：2018.6.15

  A straightforward synthesis of substituted 2-oxindoles, 3-hydroxy-2-oxindoles, and isatins has been developed. Easily accessible furans were transformed into tetrahydropyranopyrrolones by a singlet oxygen initiated cascade reaction sequence. An acid-catalyzed rearrangement, followed by aromatization, gave access to a variety of 2-oxindole motifs, which were oxidized to 3-hydroxy-2-oxindoles or isatins

  已经开发了取代的2-氧吲哚，3-羟基-2-氧吲哚和靛红的直接合成方法。容易获得的呋喃通过单线态氧引发的级联反应序列转化为四氢吡咯并吡咯烷酮。酸催化的重排，然后进行芳构化，可以使用亚甲基蓝作为自由基引发剂和分子氧作为末端氧化剂将各种2-oxindole图案氧化为3-羟基-2-oxindole或靛红。
• Transition-Metal-Free C–H Hydroxylation of Carbonyl Compounds
  作者：Moreshwar B. Chaudhari、Yogesh Sutar、Shreyas Malpathak、Anirban Hazra、Boopathy Gnanaprakasam

  DOI：10.1021/acs.orglett.7b01616

  日期：2017.7.7

  and reductant free α-C(sp3)–H hydroxylation of carbonyl compounds are reported. This method is promoted by commercially available inexpensive KO-t-Bu and atmospheric air as an oxidant at room temperature. This unified strategy is also very facile for hydroxylation of various carbonyl compound derivatives to obtain quaternary hydroxyl compounds in excellent yield. A preliminary mechanistic investigation

  据报道，过渡金属和无还原剂的羰基化合物的α-C（sp3）–H羟基化。此方法由市售的廉价KO- t- Bu和室温下的大气氧化剂作为促进剂。这种统一的策略对于各种羰基化合物衍生物的羟基化以极好的收率获得季羟基化合物也非常容易。初步的机械研究得到了同位素标记和计算研究的支持，表明过氧化物键的形成及其通过原位生成的烯醇盐的裂解。
• Facile regiospecific synthesis of 2,3-disubstituted indoles from isatins
  作者：Xiaowei Dou、Weijun Yao、Shan Wen、Yixin Lu

  DOI：10.1039/c4cc04555f

  日期：——

  A facile regiospecific synthesis of 2,3-disubstituted indoles from isatins has been developed. Nucleophilic addition of Grignard reagents to commercially available isatins, followed by reduction with borane, afforded an array of structurally diverse 2,3-disubstituted indoles in moderate to good yields. The method described herein represents a novel and very simple approach to synthesize various 2,3-disubstituted

  已经开发了从靛红容易地区域特异性合成2，3-二取代的吲哚的方法。将格氏试剂亲核地添加到市售的靛红中，然后用硼烷还原，以中等至良好的产率提供了结构上不同的2，3-二取代的吲哚阵列。本文所述的方法代表了一种新颖且非常简单的方法，用于合成各种2，3-二取代的吲哚，这是制药工业和药物化学中极为重要的结构基序。
• An efficient and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles via Zn-mediated barbier-type reaction under aqueous conditions
  作者：L Raju Chowhan、Marri Sameer Reddy、Nandigama Satish Kumar

  DOI：10.1007/s12039-017-1329-8

  日期：2017.8

   A robust and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles from isatins is described. This method introduces an ecofriendly, un-activated Zn dust, solid $$\hbox NH}_4}\hbox Cl}$$ and substrates under aqueous conditions, which has produced the product in moderate to good yields. Without using column chromatography, majority of the compounds were isolated in analytically pure form. The progress of the reaction could be visualized by naked eye. SYNOPSIS A robust and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles from isatins is described. This method introduces an ecofriendly method using un-activated Zn dust, solid $$\hbox NH}_4}\hbox Cl}$$ and substrates under aqueous conditions, which has produced the products in moderate to good yields.

   介绍了一种从异汀类化合物中快速合成3-羟基-3-烷基-2-氧茚酮的方法。该方法在水溶液条件下引入了一种环保的、未活化的锌粉、固体$$\hbox NH}_4}\hbox Cl}$$和底物，从而以中等到良好的收率生产出产品。在不使用柱层析的情况下，大部分化合物都以分析纯的形式分离出来。反应过程可以用肉眼观察到。摘要 描述了一种从异汀类化合物中快速合成 3-羟基-3-烷基-2-氧化吲哚的方法。该方法采用未活化的 Zn 粉尘、固体 $$\hbox NH}_4}\hbox Cl}$$ 和底物在水溶液条件下进行合成，以中等至良好的收率得到了产物。
• Cathodic reduction of N-(2-iodophenyl)-N-alkylcinnamides: a novel sequential electrochemical radical cyclisation and hydroxylation
  作者：Raja Munusamy、Kaveripatnam Samban Dhathathreyan、Kalpattu Kuppusamy Balasubramanian、Chitoor Sivaramakrishnan Venkatachalam

  DOI：10.1039/b100418m

  日期：——

  cyclisation has emerged as a useful route for the synthesis of benzannulated heterocycles and carbocycles. The aryl radicals are generated in situ from aryl halides (iodides or bromides) with tributylstannyl hydride–AIBN, SmI2, Co(I) or under photochemical conditions. The present work envisages the generation of aryl radicals by cathodic reduction of the carbon–iodine bond of N-(2-iodophenyl)-N-alkylcinnamides

  近年来，分子内 芳基 激进的 环化苯已成为合成苯环杂环和碳环的有用途径。这芳基自由基是由芳基卤化物（碘化物或溴化物）与三丁基锡氢化物-AIBN，SmI 2，Co（I）或在光化学条件下原位生成的。目前的工作设想芳基 阴极自由基 减少-（2-碘苯基）-N-烷基肉桂酰胺的碳碘键及其分子内结构环化。阴极减少在DMF中在脱气条件下，N-（2-碘苯基）-N-烷基肉桂酰胺选择性地生成1-烷基-3-苄基吲哚-2-酮，并且在氧气的存在下令人惊讶地产生了1-烷基-3-羟基-3-苄基吲哚- 2个 这两种产品都是通过5- exo - trig工艺形成的，产率很高。已经提出通过使用以下方法形成产品的机制：循环伏安法， 库仑法 和控制电位电解以及 氘标记。