(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)-3,4-dihydroquinoxalin-2(1H)-one | 124928-47-8

• 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: (Z)-3-(2-oxo-2-(p-tolyl)ethylidene)-3,4-dihydroquinoxalin-2(1H)-one
• 英文别名: 3-[(Z)-2-(4-methylphenyl)-2-oxoethylidene]-1,2,3,4-tetrahydroquinoxalin-2-one；(Z)-3-[2-(4-methylphenyl)-2-oxoethylidene]-3,4-dihydroquinoxalin-2(1H)-one；(3Z)-3-[2-(4-methylphenyl)-2-oxoethylidene]-1,4-dihydroquinoxalin-2-one
• CAS: 124928-47-8
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: JMESLTJTWQGOBD-GDNBJRDFSA-N

物化性质

• 熔点：
  229-230 °C (decomp)(Solv: ethyl acetate (141-78-6))
• 沸点：
  494.9±45.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 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：
  0.06
• 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-oxo-2-(p-tolyl)ethylidene)-3,4-dihydroquinoxalin-2(1H)-one 在 盐酸 、 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 反应 11.0h， 生成 (4-Methylphenyl)-(1-phenylpyrazolo[4,3-b]quinoxalin-3-yl)methanone
  参考文献：
  名称：

  新型1 H-吡唑并[3,4- b ]喹喔啉（黄酮类）的合成及生物活性

  摘要：

  一种新型系列flavazoles 3A-1的合成通过一个新的系列的第3的脱水闭环- [（α-芳基亚肼基）-aroylmethyl]喹喔啉-2（1 H ^） -酮2A-1和它们的生物活性进行了评估。前体2a-1的互变异构结构也已经阐明。

  DOI：

  10.1002/jhet.5570420202
• 作为产物：
  描述：

  5-(4-甲基苯基)呋喃-2,3-二酮 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (Z)-3-(2-oxo-2-(p-tolyl)ethylidene)-3,4-dihydroquinoxalin-2(1H)-one
  参考文献：
  名称：

  Shurov, S. N.; Pavlova, E. Yu.; Livantsova, L. I., Russian Journal of Organic Chemistry, 1993, vol. 29, # 11.2, p. 1890 - 1901

  摘要：

  DOI：

文献信息

• Five-membered 2,3-dioxo heterocycles: LXVI. Reactions of (2Z,5Z)-1-aryl-3-hydroxy-5-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene]pent-2-ene-1,4-diones with o-phenylenediamine and hydrazine. Crystalline and molecular structure of 2-{(Z)-8,8-dimethyl-2,3,8,9-tetrahydro[1,4]dioxino[2,3-g]isoquinolin-6(7H)-ylidene}-1-(3-phenyl-1H-pyrazol-5-yl)ethanone
  作者：V. V. Khalturina、Yu. V. Shklyaev、Z. G. Aliev、A. N. Maslivets

  DOI：10.1134/s1070428009100169

  日期：2009.10

  (2Z,5Z)-1-Aryl-3-hydroxy-5-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene]pent-2-ene-1,4-diones reacted with o-phenylenediamine and hydrazine to give 3-[(Z)-2-aryl-2-oxoethylidene]-1,2,3,4-tetrahydroquinoxalin-2-ones and 1-(3-aryl-1H-pyrazol-5-yl)-2-[(Z)-3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene]ethanones, respectively. The crystalline and molecular structure of 2-(Z)-8,8-dimethyl-2,3,8,9-tetrahydro[1,4]dioxino[2,3-g]isoquinolin-6(7H)-ylidene}-1-(3-phenyl-1H-pyrazol-5-yl)ethanone was determined by X-ray analysis.

  (2Z,5Z)-1-芳基-3-羟基-5-[3,3-二甲基-3,4-二氢异喹啉-1(2H)-基亚基]戊-2-烯-1,4-二酮分别与邻苯二胺和联肼反应，得到3-[(Z)-2-芳基-2-氧代乙基亚基]-1,2,3,4-四氢喹喔啉-2-酮和1-(3-芳基-1H-吡唑-5-基)-2-[(Z)-3,3-二甲基-3,4-二氢异喹林-1(2H)-基亚基]乙酮。2-(Z)-8,8-二甲基-2,3,8,9-四氢[1,4]二恶英[2,3-g]异喹啉-6(7H)-基亚基}-1-(3-苯基-1H-吡唑-5-基)乙酮的晶态及分子结构通过X射线分析测定。
• ——
  作者：I. V. Mashevskaya、R. R. Makhmudov、G. A. Aleksandrova、O. V. Golovnina、A. V. Duvalov、A. N. Maslivets

  DOI：10.1023/a:1010475811489

  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.
• 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.
• Maslivets, A. N.; Tarasova, O. P.; Berdinskii, I. S., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 5.2, p. 935 - 940
  作者：Maslivets, A. N.、Tarasova, O. P.、Berdinskii, I. S.、Andreichikov, Yu. S.

  DOI：——

  日期：——