1-ethyl-7-methylindoline-2,3-dione | 620931-79-5

• 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: 1-ethyl-7-methylindoline-2,3-dione
• 英文别名: 1-ethyl-7-methyl-1H-indole-2,3-dione；1-ethyl-7-methylindole-2,3-dione
• CAS: 620931-79-5
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: CZJDGMHPYAMRDF-UHFFFAOYSA-N

物化性质

• 沸点：
  318.6±35.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-ethyl-7-methylindoline-2,3-dione 在 calcium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.17h， 生成 2′-amino-1-ethyl-5′-hydroxy-7-methyl-2,6′-dioxo-8′-phenyl-6′Hspiro[indoline-3,4′- pyrano[3,2-g]chromene]-3′‑carbonitrile
  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：

  在 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以87%的产率得到1-ethyl-7-methylindoline-2,3-dione
  参考文献：
  名称：

  Synthesis of isatins by the palladium-catalyzed intramolecular acylation of unactivated aryl C(sp²)–H bonds

  摘要：

  通过PdCl2催化的分子内酰化，从甲酰-N-芳酰胺合成吲哚酮。

  DOI：

  10.1039/c5ra23837d

文献信息

• Lanthanide Silylamide-Catalyzed Synthesis of Pyrano[2,3-<i>b</i>]indol-2-ones
  作者：Qifa Chen、Yue Teng、Fan Xu

  DOI：10.1021/acs.orglett.1c01506

  日期：2021.6.18

  A lanthanide silylamide-catalyzed tandem reaction of isatins, diethyl phosphite, and 2,3-diarylcyclopropenones has been developed. A series of pyrano[2,3-b]indol-2-ones were synthesized in high yields. The cooperation of the Lewis acidity of the lanthanide center and the Bronsted basicity of the N(SiMe3)2 anion may be the key factor affecting the catalytic activity of lanthanide amides.

  已经开发了镧系元素甲硅烷基酰胺催化的靛红、亚磷酸二乙酯和 2,3-二芳基环丙烯酮的串联反应。以高产率合成了一系列吡喃并[2,3 - b ]indol-2-ones。镧系元素中心的路易斯酸度和N(SiMe 3 ) 2阴离子的布朗斯台德碱度的协同作用可能是影响镧系酰胺催化活性的关键因素。
• Synthesis of N-alkyl isatins via oxidative cyclization of N-alkyl 2-bromo(chloro)acetanilides
  作者：Qingwen Gui、Fenglin Dai、Jidan Liu、Peixing Chen、Zhiyong Yang、Xiang Chen、Ze Tan

  DOI：10.1039/c4ob00118d

  日期：——

  A highly efficient method for the synthesis of N-alkyl isatins starting from N-alkyl 2-bromo or 2-chloro acetanilides is described. The starting materials are easy to prepare and the yields of isatins are generally high. Operationally the reaction is very simple to run. Even though best results were obtained with a catalytic amount of CuI, the reactions of N-alkyl 2-bromo acetanilides actually performed well even in the absence of any metal catalyst.

  本文描述了一种从N-烷基2-溴或2-氯乙酰苯胺合成N-烷基靛红的高效方法。起始原料易于制备，靛红的产率通常较高。在操作上，该反应非常简单易行。尽管使用催化量的CuI可获得最佳结果，但即使在没有任何金属催化剂的情况下，N-烷基2-溴乙酰苯胺的反应也能良好进行。
• A catalytic asymmetric hetero-Diels–Alder reaction of olefinic azlactones and isatins: facile access to chiral spirooxindole dihydropyranones
  作者：Tai-Ping Gao、Jun-Bing Lin、Xiu-Qin Hu、Peng-Fei Xu

  DOI：10.1039/c4cc03896g

  日期：——

  A catalytic asymmetric hetero-Diels-Alder (HDA) reaction has been achieved through hydrogen-bond directed gamma-addition of olefinic azlactones to isatins. This methodology provides an efficient access to spirooxindole dihydropyranones in moderate to good yields and with excellent enantioselectivities.

  催化不对称杂Diels-Alder（HDA）反应是通过氢键直接将烯烃a内酯加到isatins上的伽马加成反应而实现的。这种方法可以高效，高效地获得螺环吲哚二氢吡喃酮，并且具有出色的对映选择性。
• IBX-promoted domino reaction of α-hydroxy amides: a facile one-pot synthesis of isatins
  作者：Yaoling Wang、Xu Cheng、Zhen Zhan、Xiaojun Ma、Ruifang Nie、Li Hai、Yong Wu

  DOI：10.1039/c5ra25036f

  日期：——

  A novel and temperature-controlled oxidation of α-hydroxy amides in the presence of IBX is described. The divergent one-pot synthesis of isatins and α-formyl amides was achieved in good to excellent yields under metal-free conditions. And these two mild methods can tolerate a variety of functional groups, and are operationally simple.

  描述了在IBX存在下α-羟基酰胺的新颖且温度控制的氧化。在无金属条件下，一锅法合成靛红和α-甲酰酰胺的收率很高。这两种温和的方法可以耐受多种功能基团，并且操作简单。
• Ru(III)-mediated intramolecular ortho-C(sp2)–H activation/oxidative acylation: one-pot synthesis of isatins from α-hydroxy amides
  作者：Yaoling Wang、Weijian Li、Xu Cheng、Zhen Zhan、Xiaojun Ma、Li Guo、Hui Jin、Yong Wu

  DOI：10.1016/j.tet.2016.04.041

  日期：2016.6

  A novel and efficient synthesis of isatins from α-hydroxy amides via ruthenium-mediated aromatic C–H activation is described. The reactions proceeded smoothly under mild conditions and generated the corresponding products in good to excellent yields. This methodology has a broad substrate scope and opens up an interesting and attractive avenue for the application of intramolecular ortho-C–H activation

  描述了通过钌介导的芳香族C–H活化从α-羟基酰胺合成一种新型高效的isatin 。反应在温和条件下平稳进行，并以良好至优异的产率产生相应的产物。该方法具有广泛的底物范围，并为分子内邻-C–H活化的应用开辟了有趣且有吸引力的途径。