ethyl-2-(5-bromo-2-oxoindolin-3-ylidene)-2-cyanoacetate

• 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: ethyl-2-(5-bromo-2-oxoindolin-3-ylidene)-2-cyanoacetate
• 英文别名: [5-Bromo-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-cyano-acetic acid ethyl ester；ethyl 2-(5-bromo-2-oxo-1H-indol-3-ylidene)-2-cyanoacetate
• 化学式: C₁₃H₉BrN₂O₃
• 分子量: 321.13
• InChiKey: CDLPXDJPAROXNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl-2-(5-bromo-2-oxoindolin-3-ylidene)-2-cyanoacetate 在 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 ethyl 3-acetyl-9-benzyl-6-bromo-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate
  参考文献：
  名称：

  Phosphorus-containing Lewis base catalyzed highly regioselective cyclization of isatin derived electron-deficient alkenes with but-3-yn-2-one

  摘要：

  In this paper, we reported that phosphorus-containing Lewis bases catalyzed [4+2] cyclization of N-protected isatin derived electron-deficient alkenes with but-3-yn-2-one could proceed smoothly to give the corresponding dihydropyrano[2,3-b]indoles in good to excellent yields under mild conditions. The substrate scope has been carefully examined and the plausible reaction mechanism has been also proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.036
• 作为产物：
  描述：

  5-溴靛红 、 氰乙酸乙酯 在 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate 作用下， 反应 0.33h， 以82%的产率得到ethyl-2-(5-bromo-2-oxoindolin-3-ylidene)-2-cyanoacetate
  参考文献：
  名称：

  离子液体介导的N-甲基喹诺酮绿色合成螺并吲哚及其抗细菌活性

  摘要：

  特定任务中涉及1-甲基喹啉-2,4（1 H，3 H）-二酮1，靛红2（a-e）和丙二腈/氰基乙酸酯3（a-b）缩合的三组分反应离子液体[DBU] [Ac]（1,8-二氮杂双环[5.4.0]-十一-7-en-8-乙酸乙酸盐）被描述为螺氧杂吲哚衍生物4（a–j）。这种方法无需柱色谱即可提供高收率的产品，并评估了所得化合物对革兰氏阳性和革兰氏阴性细菌（金黄色葡萄球菌， 大肠杆菌）的抗菌活性，蜡状芽孢杆菌，枯草芽孢杆菌，鼠伤寒沙门氏菌和肺炎克雷伯菌）。在所有化合物中，四种化合物，即4b，4e，4f，4g，4j与所用标准品相比，对所有菌株均表现出中等活性。

  DOI：

  10.1002/jhet.2821

文献信息

• Synthesis of 2,6′-Dioxo-1′,5′,6′,7′-tetrahydrospiro[indoline-3,4′-pyrazolo[3,4-<i>b</i>]pyridine]-5′-carbonitriles via a One-Pot, Three-Component Reaction in Water
  作者：Abbas Rahmati、Tahmineh Kenarkoohi、Hamid Reza Khavasi

  DOI：10.1021/co300047j

  日期：2012.12.10

  A one-pot, three-component condensation reaction of an isatin, aminopyrazole, and alkyl cyanoacetate in water to give 2,6′-dioxo-1′,5′,6′,7′-tetrahydrospiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-5′-carbonitrile with good yields, at 90 °C, using a Et3N as catalyst, is described.

  靛红，氨基吡唑和氰基乙酸烷基酯在水中的一锅三组分缩合反应，得到2,6'-dioxo-1'，5'，6'，7'-四氢螺[吲哚啉-3,4'描述了在90℃下使用Et 3 N作为催化剂具有良好收率的-吡唑并[3，4- b ]吡啶] -5′-腈。
• Synthesis of Highly Functionalized Chiral 3,3′-Disubstituted Oxindoles via an Organocatalytic Enantioselective Michael Addition of Nitroalkanes to Indolylidenecyanoacetates
  作者：Lu Liu、Deyan Wu、Shu Zheng、Tengfei Li、Xiangmin Li、Sinan Wang、Jian Li、Hao Li、Wei Wang

  DOI：10.1021/ol202931e

  日期：2012.1.6

  An efficient bifunctional cinchona alkaloid derived thiourea-promoted enantioselective conjugate addition of nitroalkanes to indolylidenecyanoacetates has been developed under neat conditions. The process leads to synthetically interesting densely functionalized 3,3′-disubstituted oxindoles with creation of up to three stereogenic centers.

  在纯净条件下，已经开发了一种有效的双功能金鸡纳生物碱衍生的硫脲促进的硝基烷对映体选择性共轭加成反应。该过程导致合成有趣的密集功能化的3,3'-二取代的羟吲哚，最多可形成三个立体异构中心。
• Visible-Light-Initiated Oxidative Coupling of Indole and Active Methylene Compounds Using Eosin Y as a Photocatalyst
  作者：Sundaram Singh、Ambuj Kumar Kushwaha、Suresh Kumar Maury、Savita Kumari、Arsala Kamal、Himanshu Kumar Singh、Dhirendra Kumar

  DOI：10.1055/a-1894-8303

  日期：2022.11

  A novel, efficient, mild, and inexpensive photocatalytic approach has been established for the visible-light-initiated oxidative coupling of indole and active methylene compounds using atmospheric air and water as an oxidant in the presence of Eosin Y to give 3-methyleneindolin-2-ones. In this work, only one molecule of malononitrile, ethyl acetoacetate, or dimedone reacts with one molecule of indole

  已经建立了一种新颖、高效、温和且廉价的光催化方法，用于在 Eosin Y 存在下使用大气和水作为氧化剂，在可见光下引发吲哚和活性亚甲基化合物的氧化偶联，得到 3-methyleneindolin-2 -那些。在这项工作中，只有一分子丙二腈、乙酰乙酸乙酯或二甲酮与一分子吲哚反应，但相反，两分子巴比妥酸与一分子吲哚反应。该方法的基本特征是无金属反应、产物收率高、无副产物和使用可再生能源。
• An efficient, three-component synthesis and molecular structure of derivatives of 2-amino-3-R-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine-5,5-dioxide spirocombined with a 2-oxindole nucleus
  作者：Leonid A. Shemchuk、Dmitry A. Lega、Ruslan Gr. Redkin、Valentin P. Chernykh、Oleg V. Shishkin、Svetlana V. Shishkina

  DOI：10.1016/j.tet.2014.09.005

  日期：2014.11

  Spiro[(2-amino-3-R-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine-5,5-dioxide)-4,3'-(1'-R'-5'-R ''-indolin-2'-one)] compounds were synthesized based on the three-component interaction of benzo[c][2,1]thiazin-4-on 2,2-dioxide with corresponding isatins and appropriate methylene active nitriles in the presence of a base as a catalyst. The molecular structures of the target compounds were proved uniquely by the X-ray diffraction analysis method. (C) 2014 Elsevier Ltd. All rights reserved.
• Riyaz; Indrasena; Naidu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 1, p. 120 - 123
  作者：Riyaz、Indrasena、Naidu、Dubey

  DOI：——

  日期：——