(S)-3-hydroxy-5-nitro-3-(2-oxopropyl)indolin-2-one | 1351988-28-7

• 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)-3-hydroxy-5-nitro-3-(2-oxopropyl)indolin-2-one
• 英文别名: (3S)-3-hydroxy-5-nitro-3-(2-oxopropyl)-1H-indol-2-one
• CAS: 1351988-28-7
• 化学式: C₁₁H₁₀N₂O₅
• mdl: MFCD11107112
• 分子量: 250.211
• InChiKey: UQUBXBNIUCDTNU-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 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：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-硝基靛红 、 丙酮 在 (1S,2R)-2-(5-methylthiophen-2-yl)methylamino-1-phenylpropanol 、 溶剂黄146 作用下， 以65 %的产率得到(S)-3-hydroxy-5-nitro-3-(2-oxopropyl)indolin-2-one
  参考文献：
  名称：

  Enantioselective Aldol Reaction between Isatins and Ketones, Catalyzed by Chiral Norephedrine-Derived β-Amino Alcohols with a Thiophene Moiety

  摘要：

  DOI：

  10.1134/s1070428022060100

文献信息

• A Continuous‐Flow Route to Enantioenriched 3‐Substituted‐3‐Hydroxyoxindoles: Organocatalytic Aldol Reactions of Isatin with Acetone
  作者：Kavnen Tseke、Claire Lennon、Joseph O'Mahony、Michael Kinsella

  DOI：10.1002/ejoc.202100735

  日期：2021.11.15

  the isatin-acetone reaction at higher temperatures without compromising enantioselectivity is reported. Kamlet-Taft basicity (β) and proticity (α) of solvents were found to be crucial in describing the solubility of isatin and performance of L-leucinol organocatalyst and informed the choice of solvent for transfer to flow.

  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。
• Solvent-free asymmetric aldol reaction organocatalyzed by (S)-proline-containing thiodipeptides under ball-milling conditions
  作者：José G. Hernández、Víctor García-López、Eusebio Juaristi

  DOI：10.1016/j.tet.2011.10.093

  日期：2012.1

  protocol for the asymmetric aldol reaction between cyclohexanone and cyclopentanone with various aromatic aldehydes using a novel series of (S)-proline-containing dipeptides and thiodipeptides 1a–f as organocatalysts is reported. In general, (S)-proline-containing thiodipeptides proved to be better organocatalysts relative to their analogous amides. In particular, thiodipeptide (S,S)-1d catalyzed the stereoselective

  报道了一种有效的，无溶剂的球磨方法，该方法使用一系列新的含（S）-脯氨酸的二肽和硫代二肽1a - f作为有机催化剂，用于环己酮和环戊酮与各种芳族醛之间的不对称羟醛反应。通常，相对于其类似的酰胺，含（S）-脯氨酸的硫代二肽被证明是更好的有机催化剂。具体地讲，硫代二（小号，小号） - 1D催化的醛醇预期产品具有优良的diastereo-和对映选择性（高达的立体选择性形成至98:2反/顺博士和高达96％的ee）。这种观察结果可能归因于硫酰胺链段的N–H酸度增加，从而导致在过渡态时与醛羰基之间更强的H键相互作用，从而导致更高的立体诱导。此外，硫代二肽1f被证明是丙酮与Isatin和isatin衍生物（ee 56-86％）的醛醇缩合反应的有效有机催化剂。
• 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.