(Z)-3-(2-(4-fluorophenyl)-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-one | 1289383-33-0

• 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: (Z)-3-(2-(4-fluorophenyl)-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-one
• 英文别名: (Z)-3-[2-oxo-2-(4-fluorophenyl)ethylidene]-3,4-dihydroquinoxalin-2(1H)-one；(3Z)-3-[2-(4-fluorophenyl)-2-oxoethylidene]-1,4-dihydroquinoxalin-2-one
• CAS: 1289383-33-0
• 化学式: C₁₆H₁₁FN₂O₂
• 分子量: 282.274
• InChiKey: UIXFWJVCVKBYOF-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2-(4-fluorophenyl)-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-one 以 diphenyl ether-biphenyl eutectic 、 氯仿 为溶剂， 生成 3-(4-fluorobenzoyl)furo[3,2-b]quinoxalin-2(4H)-one
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones

  摘要：

  Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1H-pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones that at the thermal decarbonylation generated acyl(3-oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.

  DOI：

  10.1134/s1070428011020151
• 作为产物：
  描述：

  4-(4-氟苯基)-2,4-二氧代丁酸甲酯 、 邻苯二胺 以 1,4-二氧六环 为溶剂， 以89%的产率得到(Z)-3-(2-(4-fluorophenyl)-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-one
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones

  摘要：

  Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1H-pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones that at the thermal decarbonylation generated acyl(3-oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.

  DOI：

  10.1134/s1070428011020151

文献信息

• Formation of 4-(het)aryl-3H-1,5-benzodiazepine-2-carboxylates from (het)aroylpyruvate esters and o-phenylenediamine
  作者：Ekaterina E. Khramtsova、Maksim V. Dmitriev、Andrey N. Maslivets

  DOI：10.1007/s10593-023-03235-6

  日期：2023.8

  Esters of (het)aroylpyruvic acids can react with o-phenylenediamine, leading to the formation of (Z)-3-(2-(het)aryl-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones and 4-(het)aryl-3H-1,5-benzodiazepine-2-carboxylates. The obtained product ratio depends on the electronic effects due to substituents in the (het)aroyl moiety of (het)aroylpyruvate esters and the reaction conditions. The highest ratio

  (杂)芳酰基丙酮酸的酯可以与邻苯二胺反应，导致形成 ( Z )-3-(2-(杂)芳基-2-氧代亚乙基)-3,4-二氢喹喔啉-2(1 H )-和4-(杂)芳基-3H- 1,5-苯二氮卓-2-羧酸酯。所获得的产物比率取决于由于(杂)芳酰基丙酮酸酯的(杂)芳酰基部分中的取代基所产生的电子效应和反应条件。当使用不带取代基的(杂)芳酰基丙酮酸酯时，以及在乙酸中进行反应时，观察到与药物化学相关的喹喔啉酮的最高比例，取代基会导致(杂)芳酰基部分产生负面介观效应。
• Microwave-assisted One-pot Efficient Synthesis of Functionalized 2-Oxo-2-phenylethylidenes-linked 2-Oxobenzo[1,4]oxazines and 2-Oxoquino[1,4]oxalines: Synthetic Applications, Antioxidant Activity, SAR and Cytotoxic Studies
  作者：Vashundhra Sharma、Pradeep K. Jaiswal、Dharmendra K. Yadav、Mukesh Saran、Jaroslav Prikhodko、Manas Mathur、Ajit K. Swami、Irina V. Mashevskaya、Sandeep Chaudhary

  DOI：10.17344/acsi.2017.3709

  日期：2017.12.15

  A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2- phenylethylidene)-3, 4-dihydro-2H-benzo[b][1,4] oxazin-2-ones (11a-n) in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3,4-dihydroquinoxalin-2(1H)-ones (14a-h) (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 +/- 0.08 mu g/mL, 9.89 +/- 0.15 mu g/mL and 8.97 +/- 0.13 mu g/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 mu g/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity in comparison to the reference standard BHT (C-0.5 FRAP = 546.2 mu M). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T(3) fibroblast cell lines using MTT assay.
• ANDREJCHIKOV YU. S.; PITIRIMOVA S. G.; CAPAEBA R. F.; GEJN V. L.; PLAXINA+, XIMIYA GETEROTSIKL. SOEDIN., 1978, HO 3 407-410
  作者：ANDREJCHIKOV YU. S.、 PITIRIMOVA S. G.、 CAPAEBA R. F.、 GEJN V. L.、 PLAXINA+

  DOI：——

  日期：——
• Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones
  作者：I. V. Mashevskaya、I. G. Mokrushin、K. S. Bozdyreva、A. N. Maslivets

  DOI：10.1134/s1070428011020151

  日期：2011.2

  Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1H-pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones that at the thermal decarbonylation generated acyl(3-oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.