3-hydroxy-3-(3,3-dimethyl-2-oxobutyl)-2-oxindole | 27302-71-2

• 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-hydroxy-3-(3,3-dimethyl-2-oxobutyl)-2-oxindole
• 英文别名: 3-(3,3-dimethyl-2-oxobutyl)-3-hydroxyindolin-2-one；3-(3,3-Dimethyl-2-ketobut-1-yl)-hydroxyoxindol；3-(3,3-dimethyl-2-oxo-butyl)-3-hydroxy-1,3-dihydro-indol-2-one；3-hydroxy-3-(3,3-dimethyl-2-oxo-butyl)-indolin-2-one；3-Hydroxy-3-(3,3-dimethyl-2-oxo-butyl)-indolin-2-on；3-(3,3-Dimethyl-2-oxobutyl)-3-hydroxy-2-indolinone；3-(3,3-dimethyl-2-oxobutyl)-3-hydroxy-1H-indol-2-one
• CAS: 27302-71-2
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: JWDUMWNFXPKAJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3-hydroxy-3-(3,3-dimethyl-2-oxobutyl)-2-oxindole 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到3-(3',3'-Dimethyl-2-hydroxybutyl)indol
  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：

  4,4-dimethyl-3-oxopentanoic acid 、 靛红 以 乙酸乙酯 为溶剂， 反应 12.0h， 以83%的产率得到3-hydroxy-3-(3,3-dimethyl-2-oxobutyl)-2-oxindole
  参考文献：
  名称：

  分子筛介导的β-酮酸脱羧曼尼希和羟醛反应

  摘要：

  报道了分子筛介导的β-酮酸与磺酰基亚胺的曼尼希脱羧反应。该方案可有效制备合成上有用的β-氨基酮。还描述了类似的分子筛促进的β-酮酸和靛红之间的脱羧醛醇缩合反应，其以优异的产率提供了生物活性的3-取代的-3-羟基-吲哚。

  DOI：

  10.1016/j.tetlet.2013.06.030

文献信息

• A New Mild Method for Synthesis of Marine Alkaloid Fascaplysin and Its Therapeutically Promising Derivatives
  作者：Oleg A. Tryapkin、Alexey V. Kantemirov、Sergey A. Dyshlovoy、Vladimir S. Prassolov、Pavel V. Spirin、Gunhild von Amsberg、Maria A. Sidorova、Maxim E. Zhidkov

  DOI：10.3390/md21080424

  日期：——

  addition, the number of methods for the syntheses of its derivatives is limited. In the current study, we report a new two-step method of synthesis of fascaplysin derivatives based on low temperature UV quaternization for the synthesis of thermolabile 9-benzyloxyfascaplysin and 6-tert-butylfascaplysin. 9-Benzyloxyfascaplysin was used as the starting compound to obtain 9-hydroxyfascaplysin. However

  Fascaplysin 是一种海洋生物碱，由于其多样化且有效的生物活性而被认为是主要候选药物。作为一种抗癌剂，fascaplysin 具有巨大的潜力，因为这种生物碱在癌细胞中影响多个靶点，包括抑制细胞周期蛋白依赖性激酶 4 (CDK4) 和诱导内在细胞凋亡。同时，其结构优化的研究也因其较高的毒性（主要是由DNA嵌入引起）而受到阻碍。此外，其衍生物的合成方法数量有限。在目前的研究中，我们报道了一种基于低温紫外季铵化的新型两步法 fascaplysin 衍生物合成方法，用于合成不耐热的 9-benzyloxyfascaplysin 和 6-tert-丁基 fascaplysin。使用9-苄氧基fascaplysin作为起始化合物以获得9-羟基fascaplysin。然而，发现后者在化学上高度不稳定。与 fascaplysin 相比，6-tert-Butylfascaplysin 的 DNA 嵌
• Pietra; Tacconi, Farmaco, Edizione Scientifica, 1958, vol. 13, p. 893,907
  作者：Pietra、Tacconi

  DOI：——

  日期：——
• 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.
• Molecular sieve mediated decarboxylative Mannich and aldol reactions of β-ketoacids
  作者：Fangrui Zhong、Chunhui Jiang、Weijun Yao、Li-Wen Xu、Yixin Lu

  DOI：10.1016/j.tetlet.2013.06.030

  日期：2013.8

  A molecular sieve mediated decarboxylative Mannich reaction of β-ketoacids with sulfonyl imines is reported; this protocol leads to an efficient preparation of synthetically useful β-amino ketones. An analogous molecular sieve promoted decarboxylative aldol reaction between β-ketoacids and isatins is also described, which affords bioactive 3-substituted-3-hydroxy-oxindoles in excellent yields.

  报道了分子筛介导的β-酮酸与磺酰基亚胺的曼尼希脱羧反应。该方案可有效制备合成上有用的β-氨基酮。还描述了类似的分子筛促进的β-酮酸和靛红之间的脱羧醛醇缩合反应，其以优异的产率提供了生物活性的3-取代的-3-羟基-吲哚。

表征谱图