diethyl 2-(3-oxo-2,3-dihydro-1H-2-indolyliden)malonate | 14370-76-4

• 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: diethyl 2-(3-oxo-2,3-dihydro-1H-2-indolyliden)malonate
• 英文别名: 2-(Diethoxycarbonylmethylen)-indolin-3-on；1,3-Diethyl 2-(3-oxo-2,3-dihydro-1H-indol-2-ylidene)propanedioate；diethyl 2-(3-oxo-1H-indol-2-ylidene)propanedioate
• CAS: 14370-76-4
• 化学式: C₁₅H₁₅NO₅
• mdl: MFCD02733134
• 分子量: 289.288
• InChiKey: DCHVBIYTAAXWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-(3-oxo-2,3-dihydro-1H-2-indolyliden)malonate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 11.0h， 生成 3-Oxo-2-o-tolyl-3,5-dihydro-2H-pyridazino[4,3-b]indole-4-carboxylic acid
  参考文献：
  名称：

  Structure-activity relationships of 2-Aryl-2,5-dihydropyridazino[4,3-b]indol-3(3H)-ones at the benzodiazepine receptor

  摘要：

  A large series of 2-aryl-2,5-dihydropyridazino[4,3-b]indol-3(3H)ones (PIs) carrying properly selected substituents at the indole and N-2-phenyl rings was prepared and tested as central benzodiazepine receptor (BZR) ligands and potential (anti)convulsant agents. Stereoelectronic requirements for high receptor affinity were detected by means of 2-D and 3-D QSAR analyses. BZR affinities and pharmacological profiles of the compounds were examined in comparison with some other pyridazinoindolones recently described by us and with pyrazoloquinoline (PQ) analogues. An anticonvulsant activity greater than PQs was generally observed for PIs. Notably, in the test of audiogenically induced seizures, one compound showed a potency comparable to that of diazepam. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00220-9
• 作为产物：
  描述：

  2-叠氮苯甲酸 在 2,6-二甲基吡啶 、 草酰氯 、 六氟乙酰丙酮化铜的水合物 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 diethyl 2-(3-oxo-2,3-dihydro-1H-2-indolyliden)malonate
  参考文献：
  名称：

  Azide trapping of metallocarbenes: generation of reactive C-acylimines and domino trapping with nucleophiles

  摘要：

  重要提示：Diazocarbonyl化合物在铜催化下与侧链偶氮化物反应，生成可与碳π-亲核试剂in situ捕获的反应性C-酰亚胺。

  DOI：

  10.1039/c4ra06044j

文献信息

• Synthesis and Reactivity of (3-Oxo-2,3-dihydro-1H-ylidene)acetic Acid Alkyl Esters in Diels-Alder Reactions
  作者：Jean-Yves Mérour、Lucien Chichereau、Eric Desarbre、Philippe Gadonneix

  DOI：10.1055/s-1996-4236

  日期：1996.4

  Aldolization reactions of 1-acetyl-1H-indol-3(2H)-one with glyoxal derivatives afforded (1-acetyl-3-oxo-2,3-dihydro-1H-indol-2-ylidene)acetic acid ester derivatives 2 and 3. Spiro compounds 6 were obtained by Diels-Alder reactions of 2; inverse electron demand Diels-Alder reactions of 2 afforded pyrano indoles 8.

  1-乙酰基-1H-吲哚-3(2H)-酮与醛二醛衍生物的阿尔多反应生成了（1-乙酰基-3-氧基-2,3-二氢-1H-吲哚-2-亚烯基）醋酸酯衍生物2和3。通过2的迪尔斯-阿尔德反应得到了螺旋化合物6；2的反向电子需求迪尔斯-阿尔德反应生成了吡喃吲哚8。
• Synthesis and antibacterial activity of pyridazino[4,3-b]indole-4-carboxylic acids carrying different substituents at N-2
  作者：Fausta Palluotto、Francesco Campagna、Angelo Carotti、Marcello Ferappi、Antonio Rosato、Cesare Vitali

  DOI：10.1016/s0014-827x(01)01173-9

  日期：2002.1

  The synthesis and the in vitro evaluation of antibacterial activity of new pyridazino[4,3-b]indole-4-carboxylic acids 2-4, 6 against some selected representative of Gram-positive and Gram-negative bacteria are reported. The role of the lipophilicity in the modulation of the antibacterial activity of the tested compounds is discussed. All the synthesized compounds appear quite weak against Gram-positive bacteria, whereas have no significant activity against Gram-negative bacteria. Only derivative 2g possesses an interesting activity against Gram-positive bacteria. (C) 2002 Elsevier Science S.A. All rights reserved.
• Reactions of 3-([(trifluoromethyl)sulfonyl]oxy)-1H-indole derivatives with diamines and carbon nucleophiles. Synthesis of 6H-indolo[2,3-b]quinoxaline derivatives
  作者：Béatrice Malapel-Andrieu、Jean-Yves Mérour

  DOI：10.1016/s0040-4020(98)00650-4

  日期：1998.9

  Indolic triflate reacted with 1,2-diamines to afford pyrazino[2,3-b]indole or indolo[2,3-b] quinoxaline. Carbon nucleophiles such as malonate derivatives also reacted with indolic triflate in absence of palladium catalyst to afford 2-(3-oxo-2,3 -dihydro-1H-2-indolyliden) malonate derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Structure-activity relationships of 2-Aryl-2,5-dihydropyridazino[4,3-b]indol-3(3H)-ones at the benzodiazepine receptor
  作者：F. Palluotto、A. Carotti、G. Casini、F. Campagna、G. Genchi、M. Rizzo、G.B. De Sarro

  DOI：10.1016/s0968-0896(96)00220-9

  日期：1996.12

  A large series of 2-aryl-2,5-dihydropyridazino[4,3-b]indol-3(3H)ones (PIs) carrying properly selected substituents at the indole and N-2-phenyl rings was prepared and tested as central benzodiazepine receptor (BZR) ligands and potential (anti)convulsant agents. Stereoelectronic requirements for high receptor affinity were detected by means of 2-D and 3-D QSAR analyses. BZR affinities and pharmacological profiles of the compounds were examined in comparison with some other pyridazinoindolones recently described by us and with pyrazoloquinoline (PQ) analogues. An anticonvulsant activity greater than PQs was generally observed for PIs. Notably, in the test of audiogenically induced seizures, one compound showed a potency comparable to that of diazepam. Copyright (C) 1996 Elsevier Science Ltd
• Azide trapping of metallocarbenes: generation of reactive C-acylimines and domino trapping with nucleophiles
  作者：Tina M. Bott、Bren Jordan Atienza、F. G. West

  DOI：10.1039/c4ra06044j

  日期：——

  Diazocarbonyl compounds react with pendent azides under copper catalysis to generate reactive C-acylimines that can be trapped with carbon π-nucleophilesin situ.

  重要提示：Diazocarbonyl化合物在铜催化下与侧链偶氮化物反应，生成可与碳π-亲核试剂in situ捕获的反应性C-酰亚胺。