5,7-dibromo-3-hydroxy-3-(2-oxopropyl)indolin-2-one | 188349-41-9

• 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: 5,7-dibromo-3-hydroxy-3-(2-oxopropyl)indolin-2-one
• 英文别名: 5,7-dibromo-3-hydroxy-3-(2-oxopropyl)-2-oxindole；convolutamydine A；(+/-)-5,7-dibromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole；5,7-dibromo-3-hydroxy-3-(2-oxopropyl)-1H-indol-2-one
• CAS: 188349-41-9
• 化学式: C₁₁H₉Br₂NO₃
• 分子量: 363.005
• InChiKey: MQCFLFPDNUJPOD-UHFFFAOYSA-N

物化性质

• 沸点：
  520.6±50.0 °C(Predicted)
• 密度：
  1.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,7-dibromo-3-hydroxy-3-(2-oxopropyl)indolin-2-one 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到5,7-dibromo-3-(2-hydroxypropyl)-indole
  参考文献：
  名称：

  A versatile synthetic methodology for the synthesis of tryptophols

  摘要：

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01048-7
• 作为产物：
  描述：

  5,7-二溴靛红 、 丙酮 在 二乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5,7-dibromo-3-hydroxy-3-(2-oxopropyl)indolin-2-one
  参考文献：
  名称：

  Cu(II)-噻吩-2,5-双(氨基醇)介导的不对称羟醛反应和Domino Knoevenagel Michael环化：一种新型高效路易斯酸催化剂

  摘要：

  高效路易斯酸催化体系Cu( II )-噻吩-2,5-双(氨基-醇)已被开发用于靛红衍生物与酮的对映选择性羟醛反应。新的催化体系还被证明对取代靛红与丙二腈和乙酰乙酸乙酯的一锅三组分Domino Knoevenagel Michael环化反应具有高度对映选择性。手性配体 (2 S ,2' S )-2,2'-((噻吩-2,5-二基双(亚甲基))双(氮杂二基))双(3-苯基丙-1-醇) ( L1 ) 组合使用 Cu(OAc) 2 ·H 2 O 作为新型路易斯酸催化剂，以良好至优异的产率 (81–99%) 和高对映选择性制备了 3-取代-3-羟基二氢吲哚-2-酮衍生物 ( 3a–s ) （高达 96% ee）和螺[4 H -吡喃-3,3-羟吲哚]衍生物（ 6a–l ）具有优异的产率（89–99%）和高 ee（高达 95%）。这些羟醛产物和螺羟吲哚构成了大量药物活性分子和天然产物的核心结构基序。

  DOI：

  10.1039/d2ra00674j

文献信息

• A modified Sandmeyer methodology and the synthesis of (±)-convolutamydine A
  作者：Simon J. Garden、JoséC. Torres、Alexandre A. Ferreira、Rosangela B. Silva、Angelo C. Pinto

  DOI：10.1016/s0040-4039(97)00140-8

  日期：1997.3

  (±)-Convolutamydine A (5) has been prepared by a concise synthesis form 3,5-dibromoaniline using a modified Sandmeyer methodology. The modified Sandmeyer methodology has also been found to be beneficial for the synthesis of other α-isonitrosoacetanilides. The 4,6-dibromohydrocyoxindole nucleus was further confirmed by comparison with the isomeric 5,7-dibromohydroxyoxindole.

  （±）-Convolutamydine A（5）已使用改良的Sandmeyer方法通过简明的合成形式3,5-二溴苯胺制备。还发现改进的Sandmeyer方法学对合成其他α-异亚硝基乙酰苯胺有利。通过与异构体5，7-二溴羟基羟吲哚比较，进一步确认了4，6-二溴氢羟吲哚核。
• Tailoring the Chemical Structure of Nitrogen‐Doped Carbon Dots for Nano‐Aminocatalysis in Aqueous Media
  作者：Giuseppe Gentile、Martina Mamone、Cristian Rosso、Francesco Amato、Chiara Lanfrit、Giacomo Filippini、Maurizio Prato

  DOI：10.1002/cssc.202202399

  日期：——

  different nitrogen-doped carbon dots (NCDS) are investigated for the functionalization of carbonyl compounds. The surface amines of all the NCDs were comprehensively characterized, allowing a correlation between the structural features of the nanoparticles and their catalytic performances. The most active nano-aminocatalyst was used to drive organic reactions in aqueous media.

  多点催化：研究了不同氮掺杂碳点 (NCDS) 的氨基催化活性，用于羰基化合物的功能化。对所有 NCD 的表面胺进行了全面表征，从而使纳米颗粒的结构特征与其催化性能之间存在相关性。最活跃的纳米氨基催化剂用于驱动水性介质中的有机反应。
• Mapping the Surface Groups of Amine-Rich Carbon Dots Enables Covalent Catalysis in Aqueous Media
  作者：Giacomo Filippini、Francesco Amato、Cristian Rosso、Giulio Ragazzon、Alberto Vega-Peñaloza、Xavier Companyó、Luca Dell’Amico、Marcella Bonchio、Maurizio Prato

  DOI：10.1016/j.chempr.2020.08.009

  日期：2020.11

  Carbon nanodots stand as the missing link between the molecular and the nanoscale world, owing to the unique molecular-like behavior emerging from their synthetic precursors. A converging set of analytical and spectroscopic data yields a precise inventory of the surface reactive groups of amine-rich carbon dots (NCDs-1). As a result, NCDs-1 provide a multi-functional nano-platform that is able to covalently activate carbonyl groups, form iminium-ions and enamine intermediates, and efficiently promote diverse aminocatalytic transformations in water. Remarkably, the catalytic activity of carbon dots can also govern the stereoselectivity in the bond-forming event. Indeed, the use of chiral carbon dots (NCDs-7) as catalysts affords the final aldol products with significant enantiomeric excess. The successful implementation of carbon nanostructures into chemical roles so far restricted to molecular systems opens new avenues for advanced applications where the nanoscale and the molecular realms will merge and complement each other.
• A versatile synthetic methodology for the synthesis of tryptophols
  作者：Simon J Garden、Rosângela B da Silva、Angelo C Pinto

  DOI：10.1016/s0040-4020(02)01048-7

  日期：2002.10

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Cu(<scp>ii</scp>)-thiophene-2,5-bis(amino-alcohol) mediated asymmetric Aldol reaction and Domino Knoevenagel Michael cyclization: a new highly efficient Lewis acid catalyst
  作者：Abdullah Mohammed Al-Majid、Abdullah Saleh Alammari、Saeed Alshahrani、Matti Haukka、Mohammad Shahidul Islam、Assem Barakat

  DOI：10.1039/d2ra00674j

  日期：——

  acid-catalytic system Cu(II)-thiophene-2,5-bis(amino-alcohol) has been developed for enantioselective Aldol reaction of isatin derivatives with ketones. The new catalytic system also proved to be highly enantioselective for the one pot three-component Domino Knoevenagel Michael cyclization reaction of substituted isatin with malononitrile and ethylacetoacetate. The chiral ligand (2S,2′S)-2,2′-((thiophene-2

  高效路易斯酸催化体系Cu( II )-噻吩-2,5-双(氨基-醇)已被开发用于靛红衍生物与酮的对映选择性羟醛反应。新的催化体系还被证明对取代靛红与丙二腈和乙酰乙酸乙酯的一锅三组分Domino Knoevenagel Michael环化反应具有高度对映选择性。手性配体 (2 S ,2' S )-2,2'-((噻吩-2,5-二基双(亚甲基))双(氮杂二基))双(3-苯基丙-1-醇) ( L1 ) 组合使用 Cu(OAc) 2 ·H 2 O 作为新型路易斯酸催化剂，以良好至优异的产率 (81–99%) 和高对映选择性制备了 3-取代-3-羟基二氢吲哚-2-酮衍生物 ( 3a–s ) （高达 96% ee）和螺[4 H -吡喃-3,3-羟吲哚]衍生物（ 6a–l ）具有优异的产率（89–99%）和高 ee（高达 95%）。这些羟醛产物和螺羟吲哚构成了大量药物活性分子和天然产物的核心结构基序。