2-methyl-2-propanyl (2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate | 265997-74-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methyl-2-propanyl (2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate
• 英文别名: (2,3-dioxo-2,3-dihydroindol-1-yl)acetic acid tert-butyl ester；t-butyl (2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate；isatin；tert-butyl 2-(2,3-dioxoindolin-1-yl)acetate；tert-butyl (2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate；tert-butyl 2-(2,3-dioxoindol-1-yl)acetate
• CAS: 265997-74-8
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: PBBILZVSDWJXJL-UHFFFAOYSA-N

物化性质

• 沸点：
  391.3±44.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-2-propanyl (2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate 在 calcium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.17h， 生成 tert-butyl 2-(2′-amino-3′-cyano-5′-hydroxy-2,6′-dioxo-8′-phenyl-6′H-spiro[indoline- 3,4′-pyrano [3,2-g]chromene]-1-yl)acetate
  参考文献：
  名称：

  Design, synthesis and evaluation of structurally diverse chrysin-chromene-spirooxindole hybrids as anticancer agents

  摘要：

  A series of structurally diverse chrysin-chromene-spirooxindole hybrids were designed, synthesized via a Knoevenagel/Michael/cyclization of chrysin and isatylidene malononitrile derivatives through utilizing a hybrid pharmacophore approach. The newly synthesized compounds were evaluated for their in vitro anticancer activity, and most of the compounds showed stronger anti-proliferative activity than parent compound chrysin. In particular, compound 3e had the highest cytotoxicity towards A549 cells (IC50 = 3.15 +/- 0.51 mu M), and had better selectivity in A549 cells and normal MRC-5 cells. Furthermore, compound 3e could significantly inhibit the proliferation and migration of A549 cells in a dose-dependent manner, as well as induce the apoptosis possibly through mitochondria-mediated caspase-3/8/9 activation and multi-target co-regulation of the p53 signaling pathway. Thus, our results provide in vitro evidence that compound 3e may be a potential candidate for the development of new anti-tumour drugs.

  DOI：

  10.1016/j.bmc.2019.115109
• 作为产物：
  描述：

  溴乙酸叔丁酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以94%的产率得到2-methyl-2-propanyl (2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate
  参考文献：
  名称：

  WO2007/91948

  摘要：

  公开号：

文献信息

• Eco-friendly chemoselective N-functionalization of isatins mediated by supported KF in 2-MeTHF
  作者：Ashenafi Damtew Mamuye、Serena Monticelli、Laura Castoldi、Wolfgang Holzer、Vittorio Pace

  DOI：10.1039/c5gc01002k

  日期：——

  A simple, versatile and eco-friendly approach to the functionalization of isatins.

  一种简单、多功能且环保的对异喹啉的官能化方法。
• Polyfunctional 4-quinolinones. Synthesis of 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines
  作者：María S. Shmidt、Isabel A. Perillo、Alicia Camelli、María A. Fernández、María M. Blanco

  DOI：10.1016/j.tetlet.2016.01.077

  日期：2016.3

  We present here two new methods based on rearrangement reactions to obtain novel 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines, an important family of heterocycles with potential applications. Alkyl 3-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylates were obtained by alkoxide promoted rearrangement of alkyl isatinacetates. A second synthetic route involves the alkoxide promoted reaction of both

  我们在此介绍两种基于重排反应的新方法，以获得新颖的2-取代的3-羟基-4-氧代-1,4-二氢喹啉，具有重要应用前景的重要的杂环族。通过醇盐促进烷基异氰酸酯乙酸酯的重排获得3-羟基-4-氧代-1,4-二氢喹啉-2-羧酸烷基酯。第二种合成途径涉及伊斯丁和N-甲基伊斯丁两者的醇盐促进的反应，以及具有酸性亚甲基的烷基化剂。该反应导致通过Darzens的缩合形成螺氧基环氧吲哚。当使用苯甲酰溴时，将最初获得的苯甲酰基取代的螺氧基环氧吲哚以良好或优异的收率平稳地转化为相应的2-苯甲酰基-3-羟基-4-喹啉酮。
• Oxobenzofuranylide-dihydroindolone
  申请人：Ciba Specialty Chemicals Corporation

  公开号：US06503937B1

  公开（公告）日：2003-01-07

  Oxobenzofuranylidene-dihydroindolones of formulae trans-(Ia) and cis-(Ib) and of formulae trans-(IIa) and cis-(IIb) wherein A1 and A2 are each independently of the other unsubstituted or mono- to tetra-substituted ortho-C6-C18arylene, and R1 is hydrogen or an organic radical, with the proviso that when R1 is hydrogen and A2 is 1,2-phenylene, A1 is not 9,10-anthraquinon-1,2-ylene, 4-chloro-3,5-dimethyl-1,2-phenylene or 3,5-dimethyl-1,2-phenylene, processes for their preparation and the use thereof.

  氧苯并呋喃亚甲基二氢吲哚酮的结构式trans-(Ia)和cis-(Ib)，以及结构式trans-(IIa)和cis-(IIb)，其中A1和A2分别独立地为未取代或单至四取代的邻位C6-C18芳基，R1为氢或有机基团，条件是当R1为氢且A2为1,2-苯基时，A1不是9,10-蒽醌-1,2-亚基，4-氯-3,5-二甲基-1,2-苯基或3,5-二甲基-1,2-苯基，其制备方法及用途。
• Organocatalytic asymmetric decarboxylative cyanomethylation of isatins using l-proline derived bifunctional thiourea
  作者：V. Pratap Reddy Gajulapalli、Poopathy Vinayagam、Venkitasamy Kesavan

  DOI：10.1039/c4ob00271g

  日期：——

  First asymmetric decarboxylative cyanomethylation of isatins is reported herewith using bifunctional thiourea derived from L-proline in good yields and enantioselectivities. This strategy enables the construction of various 3-cyanomethylene substituted 3-hydroxyoxindoles in enantioselective manner. Enantioselective synthesis of CPC-1 alkaloid has been accomplished in fewer steps.

  首次报道了使用源自L-脯氨酸的双功能硫脲进行不对称脱羧氰甲基化的结果，良好的产率和对映选择性。这一策略使得以对映选择性的方式构建多种3-氰甲基取代的3-羟基氧化吲哚成为可能。CPC-1生物碱的对映选择性合成已经在更少的步骤中完成。
• Asymmetric Catalytic Vinylogous Addition Reactions Initiated by Meinwald Rearrangement of Vinyl Epoxides
  作者：Jinxiu Xu、Yanji Song、Jun He、Shunxi Dong、Lili Lin、Xiaoming Feng

  DOI：10.1002/anie.202102054

  日期：2021.6.21

  catalytic asymmetric multiple vinylogous addition reactions initiated by Meinwald rearrangement of vinyl epoxides were realized by employing chiral N,N′-dioxide/ScIII complex catalysts. The vinyl epoxides, as masked β,γ-unsaturated aldehydes, via direct vinylogous additions with isatins, 2-alkenoylpyridines or methyleneindolinones, provided a facile and efficient way for the synthesis of chiral 3-hydroxy-3-substituted

  通过使用手性N , N '-dioxide/Sc III实现了第一个由乙烯基环氧化物的 Meinwald 重排引发的催化不对称多重乙烯基加成反应复杂的催化剂。乙烯基环氧化物作为掩蔽的 β,γ-不饱和醛，通过与靛红、2-链烯酰基吡啶或亚甲基吲哚酮直接进行乙烯基加成，为合成手性 3-羟基-3-取代的羟吲哚、α,β-提供了一种简便有效的方法分别具有高效率和立体选择性的不饱和醛和螺环己烯吲哚酮。对照实验和动力学研究表明，路易斯酸充当双任务催化剂，控制初始重排以匹配随后的对映选择性乙烯基加成反应。提出了具有可能的过渡模型的催化循环来说明反应机理。