(S)-5-chloro-3-hydroxy-3-(2-oxopropyl)indolin-2-one | 1312942-25-8

• 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: (S)-5-chloro-3-hydroxy-3-(2-oxopropyl)indolin-2-one
• 英文别名: (3S)-5-chloro-3-hydroxy-3-(2-oxopropyl)-1H-indol-2-one
• CAS: 1312942-25-8
• 化学式: C₁₁H₁₀ClNO₃
• mdl: MFCD07545638
• 分子量: 239.658
• InChiKey: ZSAGYDHNYJBYTB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 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

• 作为产物：
  描述：

  5-氯靛红 、 丙酮 在 L-亮氨醇 、 水 作用下， 反应 12.0h， 以99%的产率得到(S)-5-chloro-3-hydroxy-3-(2-oxopropyl)indolin-2-one
  参考文献：
  名称：

  对映体富集的 3-取代-3-羟基吲哚的连续流动途径：靛红与丙酮的有机催化羟醛反应

  摘要：

  报道了 3-取代-3-羟基吲哚的首次连续流动合成，为在更高温度下加速靛红-丙酮反应提供了一种更安全、无缝的方法，同时不影响对映选择性。发现溶剂的 Kamlet-Taft 碱度 (β) 和质子性 (α) 在描述靛红的溶解度和 L-亮氨醇有机催化剂的性能方面至关重要，并为转移到流动的溶剂选择提供信息。

  DOI：

  10.1002/ejoc.202100735

文献信息

• Synthesis of planar chiral [2.2]paracyclophane-based amino thioureas and their application in asymmetric aldol reactions of ketones with isatins
  作者：Yu Lu、Yudao Ma、Shaobo Yang、Manyuan Ma、Hongju Chu、Chun Song

  DOI：10.1016/j.tetasy.2013.07.023

  日期：2013.9

  were used as bifunctional catalysts for organocatalytic enantioselective aldol reactions between ketones and isatins, affording the desired adducts containing a chiral tertiary alcohol in high yields (up to 92% yield) and with good enantioselectivity (up to 88% ee). This is a successful example of employing planar chiral [2.2]paracyclophane-based amino thioureas in asymmetric aldol reactions.

  已经设计并合成了几种新颖的基于[2.2]对环环烷的氨基硫脲。[2.2]对环烷基氨基硫脲被用作双官能催化剂，用于酮和靛红之间的有机催化对映选择性醛醇缩合反应，以高收率（高达92％的收率）和良好的对映选择性（最高收率）提供了所需的含有手性叔醇的加合物。 88％ee）。这是在不对称醛醇缩合反应中使用基于平面手性[2.2]对环硫基的氨基硫脲的成功实例。
• Natural amino acid salt catalyzed aldol reactions of isatins with ketones: highly enantioselective construction of 3-alkyl-3-hydroxyindolin-2-ones
  作者：Gong Chen、Yuan Ju、Tao Yang、Zicheng Li、Wei Ang、Zitai Sang、Jie Liu、Youfu Luo

  DOI：10.1016/j.tetasy.2015.07.008

  日期：2015.9

  The asymmetric synthesis of 3-alkyl-3-hydroxyindolin-2-ones via direct aldol reaction of isatin with ketones catalyzed by natural amino acid salts is described, in which the phenylalanine lithium salt was found to be the best catalyst. This strategy was then applied to a variety of isatin and ketone substrates and the corresponding aldol products were obtained in excellent yields (up to 97%) with good

  描述了通过Isatin与天然氨基酸盐催化的酮直接进行羟醛直接不对称合成3-烷基-3-羟基吲哚-2-酮的方法，其中发现苯丙氨酸锂盐是最好的催化剂。然后，将该策略应用于各种靛红和酮底物，并以优异的收率（高达97％）和良好的对映选择性（高达90％）获得了相应的羟醛产品。
• Enantioselective Solvent-Free Synthesis of 3-Alkyl-3-hydroxy-2-oxoindoles Catalyzed by Binam-Prolinamides
  作者：Abraham Bañn-Caballero、Jesús Flores-Ferrándiz、Gabriela Guillena、Carmen Nájera

  DOI：10.3390/molecules200712901

  日期：——

  BINAM-prolinamides are very efficient catalyst for the synthesis of non-protected and N-benzyl isatin derivatives by using an aldol reaction between ketones and isatins under solvent-free conditions. The results in terms of diastereo- and enantioselectivities are good, up to 99% de and 97% ee, and higher to those previously reported in the literature under similar reaction conditions. A high variation of the results is observed depending on the structure of the isatin and the ketone used in the process. While 90% of ee and 97% ee, respectively, is obtained by using (Ra)-BINAM-l-(bis)prolinamide as catalyst in the addition of cyclohexanone and α-methoxyacetone to free isatin, 90% ee is achieved for the reaction between N-benzyl isatin and acetone using N-tosyl BINAM-l-prolinamide as catalyst. This reaction is also carried out using a silica BINAM-l-prolinamide supported catalyst under solvent-free conditions, which can be reused up to five times giving similar results.

  BINAM-prolinAMides 是一种非常高效的催化剂，可通过在无溶剂条件下使用酮和异靛的醛缩反应合成非保护性和 N-苄基异靛衍生物。在立体选择性和对映选择性方面的结果良好，达到高达 99% 的 diastereomer excess (de) 和 97% 的 enantiomeric excess (ee)，且高于文献中在类似反应条件下所报告的结果。根据所使用的异靛和酮的结构，结果呈现出较大的变化。当使用 (Ra)-BINAM-l-(bis)prolinAMide 作为催化剂，将环己酮和 α-甲氧基丙酮添加到自由异靛时，分别可获得 90% 和 97% 的 ee；而在 N-苄基异靛与丙酮的反应中，使用 N-tosyl BINAM-l-prolinAMide 作为催化剂可获得 90% 的 ee。该反应还可以在无溶剂条件下使用硅基 BINAM-l-prolinAMide 支持催化剂进行，该催化剂可重复使用多达五次，并产生类似的结果。
• 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。
• trans-4-Hydroxy-l-prolinamide as an efficient catalyst for direct asymmetric aldol reaction of acetone with isatins
  作者：Geeta Devi Yadav、Surendra Singh

  DOI：10.1016/j.tetasy.2016.04.008

  日期：2016.7

  Prolinamide (2S,4R)-4-hydroxy-N-((S)-1-phenylethyl)pyrrolidine-2-carboxamide was found to be an efficient organocatalyst (10 mol %) for the direct asymmetric aldol reactions of isatins with acetone at -35 degrees C in THF and afforded the product in 79% yield with 74% ee. We have generalised the methodology for the direct asymmetric aldol reaction between isatin derivatives and acetone, and the corresponding aldol products were obtained in high yields (up to 99%) and with moderate enantioselectivities (up to 80%). This method has been applied to the enantioselective synthesis of (S)-convolutamydine. (C) 2016 Elsevier Ltd. All rights reserved.