(1E,4E)-1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one | 621-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1E,4E)-1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one
• 英文别名: (E,E)-1,5-Di(3-nitrophenyl)-1,4-pentadien-3-one；1,5-bis-(3'-nitrophenyl)-penta-1E,4E-dien-3-one；(1E,4E)-1,5-bis-(3-nitrophenyl)-penta-1,4-dien-3-one；Bis-<3-nitrobenzal>-aceton；Bis-(3-nitrobenzal)-aceton
• CAS: 621-21-6
• 化学式: C₁₇H₁₂N₂O₅
• 分子量: 324.293
• InChiKey: ZPQURSDVJWZXLQ-FIFLTTCUSA-N

物化性质

• 熔点：
  237 °C
• 沸点：
  533.8±50.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one 在 过氧乙酸 、 dipotassium hydrogenphosphate 、 sodium hydrogensulfide 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 5.0h， 生成 2,3,5,6-Tetrahydro-2,6-di(3-nitrophenyl)thiopyran-4-one 1,1-dioxide
  参考文献：
  名称：

  Syntheses of 4H-Thiopyran-4-one 1,1-Dioxides as Precursors to Sulfone-Containing Analogs of Tetracyanoquinodimethane

  摘要：

  Synthetic routes to the unsubstituted 4H-thiopyran-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation af 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.

  DOI：

  10.1021/jo00111a027
• 作为产物：
  描述：

  2,3,5,6-Tetrahydro-2,6-di(3-nitrophenyl)thiopyran-4-one 在 过氧乙酸 、 硫酸 、 碘 、 二甲基亚砜 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (1E,4E)-1,5-bis(3-nitrophenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Syntheses of 4H-Thiopyran-4-one 1,1-Dioxides as Precursors to Sulfone-Containing Analogs of Tetracyanoquinodimethane

  摘要：

  Synthetic routes to the unsubstituted 4H-thiopyran-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation af 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.

  DOI：

  10.1021/jo00111a027

文献信息

• BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER
  申请人：Shibata Hiroyuki

  公开号：US20100152493A1

  公开（公告）日：2010-06-17

  It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

  要改善姜黄素的溶解度，以开发一种能够在低浓度下抑制各种癌细胞生长的抗肿瘤化合物。因此，披露了一种新型合成化合物，双(芳基甲基亚乙酮)，具有优异的抗肿瘤活性和化学预防活性。合成并筛选了一种双(芳基甲基亚乙酮)（即具有姜黄素骨架的衍生物），它是一种抗肿瘤化合物并具有化学预防活性。可以合成具有增强抗肿瘤活性和化学预防活性的衍生物。
• New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cycloaddition reaction and their conformational structures
  作者：N. N. Pesyan、S. Noori、S. Poorhassan、E. Şahin

  DOI：10.4314/bcse.v28i3.12

  日期：——

  Crossed-aldol condensation reaction of aromatic aldehydes with ketones such as; acetone and cyclohexanone leads to the efficient formation of cross conjugated α,β-unsaturated ketones in excellent yield. The intermolecular and then intramolecular Michael addition reaction of α,β-unsaturated ketones derived from acetone and cyclohexanone with (thio)barbituric acids lead to synthesis new type of 7,11-diaryl-2

  芳族醛与酮的交联醇醛缩合反应，如：丙酮和环己酮可有效地形成交叉共轭的α，β-不饱和酮，且产率极高。丙酮和环己酮衍生的α，β-不饱和酮与（硫代）巴比妥酸的分子内和分子内迈克尔加成反应导致合成新型的7,11-二芳基-2,4-二氮杂螺[5.5]十一烷-1， 3,5,9-丁酮和2,4-二芳基-1'H-螺[双环[3.3.1]壬烷-3,5'-嘧啶] -2'，4'，6'，9（3'H ）-四酮，分别具有良好的收率。通过1 H NMR，13 C NMR，FT-IR，UV-Visible，质谱和X射线晶体学技术进行结构阐明。讨论了一种可能的形成机理。结构构象还由邻近质子和双子质子之间的二面角衍生的耦合常数证明。来自巴比妥酸的螺环化合物的NH质子的1 H NMR光谱显示宽的单峰，而源自硫代巴比妥酸的螺环化合物中的这些质子显示两个不同的峰。关键词：交叉羟醛缩合，迈克尔加成，[1 + 5]环加成，巴比妥酸，构象，螺环巴比妥酸盐。化学
• Monocarbonyl Analogs of Curcumin with Potential to Treat Colorectal Cancer
  作者：Marta Clariano、Vanda Marques、João Vaz、Salma Awam、Marta B. Afonso、Maria Jesus Perry、Cecília MP Rodrigues

  DOI：10.1002/cbdv.202300222

  日期：2023.3

  small library of monocarbonyl analogs of curcumin 1a–q was synthesized. Lipophilicity and stability in physiological conditions were both assessed by HPLC-UV, while two different methods assessed the electrophilic character of each compound monitored by NMR and by UV-spectroscopy. The potential therapeutic effect of the analogs 1a–q was evaluated in human colon carcinoma cells and toxicity in immortalized

  姜黄素具有多种生物学特性，使得这种化合物可以有效治疗包括癌症在内的多种疾病。然而，姜黄素的临床应用因其较差的药代动力学而受到影响，因此寻找具有更好药代动力学和药理学特性的新型类似物至关重要。在这里，我们的目的是评估姜黄素单羰基类似物的稳定性、生物利用度和药代动力学特征。合成了姜黄素1a–q的单羰基类似物的小型文库。生理条件下的亲脂性和稳定性均通过 HPLC-UV 进行评估，同时通过 NMR 和 UV 光谱监测两种不同的方法评估每种化合物的亲电特性。在人结肠癌细胞中评估了类似物1a–q的潜在治疗效果以及在永生化肝细胞中的毒性。我们的结果表明，姜黄素类似物1e是一种有前景的抗结直肠癌药物，具有更高的稳定性和功效/安全性。
• 10.1039/d4dt00985a
  作者：Chandra, Anushri、Basu, Pousali、Raha, Shreya、Dhibar, Papu、Bhattacharya, Samaresh

  DOI：10.1039/d4dt00985a

  日期：——

  2′-bipyridine and phen = 1,10-phenanthroline). The crystal structure of [Ru(L3)2(bpy)] has been determined and the structure of [Ru(L2)2(phen)] has been optimized by the DFT method. The electronic spectra of the four [Ru(Ln)2(dmso)2] complexes and the two derivatives ([Ru(Ln)2(L′)]; n = 3, L′ = bpy; n = 2, L′ = phen), recorded in dichloromethane solutions, show intense absorptions spanning the visible and

  [Ru(dmso) 4 Cl 2 ]与四黄原酸钾盐(RO–C( S) S- ; R = Me、Et、 i Pr 和t Bu) 配体（表示为 L n ； n = 1–4）在热甲醇中提供一组 [Ru(L n ) 2 (dmso) 2 ] 类型的混合配体配合物。四种配合物的晶体结构均已测定，表明黄原酸配体与金属中心结合形成四元螯合物，dmso通过硫配位，互为顺式。借助DFT计算评估了这些配合物的顺式异构体和其他可能的反式异构体的相对热力学稳定性，这表明顺式异构体是更稳定的异构体。 [Ru(L n ) 2 (dmso) 2 ]配合物中的配位 dmso 可以通过螯合双齿配体（表示为 L'）轻松置换，以提供 [Ru(L n ) 2 (L')] 类型的配合物，正如通过分离两个这样的复合物所证明的，即。[Ru(L 3 ) 2 (bpy)]和[Ru(L 2 ) 2 (phen)]（bpy = 2,2′-联吡啶和phen
• Ahmed, M. Giasuddin; Ahmed, Syeda Asghari; Ahmed, S. Mosaddeq, Journal of Chemical Research, 2005, # 10, p. 622 - 625
  作者：Ahmed, M. Giasuddin、Ahmed, Syeda Asghari、Ahmed, S. Mosaddeq、Hossain, M. Mahmun、Hussam, Abul

  DOI：——

  日期：——