1,5-bis(2,4-dichlorophenyl)penta-1,4-dien-3-one | 66896-93-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,5-bis(2,4-dichlorophenyl)penta-1,4-dien-3-one
• 英文别名: 1,5-Bis(2,4-dichlorophenyl)-1,4-pentadien-3-one
• CAS: 66896-93-3
• 化学式: C₁₇H₁₀Cl₄O
• 分子量: 372.078
• InChiKey: GSCSMANFUIJPIU-UHFFFAOYSA-N

物化性质

• 熔点：
  168-169 °C
• 沸点：
  517.5±50.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  22
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,5-bis(2,4-dichlorophenyl)penta-1,4-dien-3-one 在 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 反应 0.05h， 以94%的产率得到1-[3-(2,4-Dichlorophenyl)-5-[2-(2,4-dichlorophenyl)ethenyl]-3,4-dihydropyrazol-2-yl]ethanone
  参考文献：
  名称：

  Mild and Ecofriendly Tandem Synthesis, and Spectral and Antimicrobial Studies of N¹-Acetyl-5-aryl-3-(substituted styryl)pyrazolines

  摘要：

  N-1-acetyl-5-aryl-3-(substituted styryl) pyrazolines were synthesized by the cyclocondensation of 1,5-substituted diphenyl-1,4-pentadien-3-ones with hydrazine hydrate and a cyclizing agent such as acetic acid in ethanol. The title compounds were synthesized using conventional and solvent-free approaches, which involves mechanochemical mixing, microwave-irradiation, and ultrasound-irradiation methods in the presence of a solid support. The synthesized compounds have been characterized by elemental analyses and spectral data (IR, PMR, and FAB-mass). All the synthesized compounds have been evaluated for their antibacterial and antifungal activities. Some compounds have shown promising biological activity.

  DOI：

  10.1080/10426500802388318
• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 丙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 1,5-bis(2,4-dichlorophenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  对十二烷基苯磺酸在水介质中超声辐射催化合成2-（1,5-二芳基-1,4-戊二烯-3-亚甲基）-肼甲酰亚胺盐酸盐。

  摘要：

  mid胺化合物是非常重要的合成中间体，可以作为许多天然产物和药物分子合成中的通用前体。超声，对十二烷基苯磺酸（DBSA）和水作为溶剂的使用改善了不同的2-（1,5-二芳基-1,4-戊二烯-3-亚烷基）-肼基羧酰亚胺酰胺盐酸盐的合成。1,5-二苯基-1,4-戊二烯-3-酮与氨基胍盐酸盐缩合的最佳反应条件如下：1,5-二苯基-1,4-戊二烯-3-酮（1，1 mmol ），氨基胍盐酸盐（1.1 mmol），DBSA（0.5 mmol），水10 mL，反应温度25-27°C，照射频率25 kHz。在2小时内以94％的收率获得2a。在相同条件下，在2-3h内以84-94％的收率获得了其他七个seven基hydr。

  DOI：

  10.1016/j.ultsonch.2012.02.009

文献信息

• Chemoselective Double Michael Addition: Synthesis of 2,6-Diarylspiro[Cyclohexane-1,3′-Indoline]-2′,4-Diones via Addition of Indolin-2-One to Divinyl Ketones
  作者：Zheng Li、Jiasheng Li、Jingya Yang

  DOI：10.3184/174751917x14878812592779

  日期：2017.3

  Seventeen examples of 2,6-diarylspiro[cyclohexane-1,3′-indoline]-2′4-diones were efficiently prepared by the Cs₂CO₃-catalysed chemoselective double Michael additions of indolin-2-one to divinyl ketones. This method has the advantage of high chemoselectivity, mild reaction conditions, high yield and atom- and step-economy.

  通过 Cs2CO3 催化吲哚啉-2-酮与二乙烯基酮的化学选择性双迈克尔加成反应，有效地制备了 17 个 2,6-二芳基螺[环己烷-1,3′-吲哚啉]-2′4-二酮的实例。该方法具有化学选择性高、反应条件温和、产率高、原子和步骤经济等优点。
• Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones
  作者：Bin Wu、Guo-Gui Liu、Mei-Qiu Li、Yong Zhang、Shao-Yun Zhang、Jun-Ru Qiu、Xiao-Ping Xu、Shun-Jun Ji、Xing-Wang Wang

  DOI：10.1039/c0cc05418f

  日期：——

  Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1) and high enantiomeric ratios (up to 97 : 3).

  硫脲改性的金鸡纳生物碱作为双功能催化剂和碱，可以通过两次迈克尔加成反应，用硝基甲烷催化二乙烯基酮的[5 + 1]逐步环化，从而提供了具有良好收率，优异的非对映选择性（> 20：1的旋光性4-硝基-环己酮）。 ）和高对映体比例（高达97：3）。
• Fe-catalyzed dithiane radical induced C−S bond activation−addition to α, β-unsaturated ketones
  作者：Deng Min、Xinyu Yuan、Teng Liu、Jian Liu、Shouchu Tang

  DOI：10.1002/adsc.201800241

  日期：2018.5.2

  An efficient and clean strategy to construct organosulfur compounds has been developed via a Fe‐catalyzed dithiane C−S bond activation/addition process with α, β‐unsaturated ketones. This C−S activation protocol exhibits excellent reactivities, and up to 92% yield of the corresponding thioether‐thioester derivatives could be obtained under the mild conditions, allowing the ready preparation of a number

  通过铁催化的二硫键与α，β-不饱和酮的CS键活化/加成过程，已经开发出一种有效且清洁的构造有机硫化合物的策略。此CS活化方案具有出色的反应活性，在温和的条件下可获得高达92％的相应硫醚-硫酯衍生物收率，从而可以制备许多具有合成价值的S-连接的共轭物。
• 不对称双共轭加成合成光学活性酮类化合物的方法
  申请人：河南师范大学

  公开号：CN112811996B

  公开（公告）日：2023-01-03

  本发明公开了不对称双共轭加成合成光学活性酮类化合物的方法，属于有机化学中的不对称合成技术领域。具体步骤如下：以二烯酮1和有机硼酸2为原料，在手性联二萘酚或手性四苯并环辛四烯类催化剂和分子筛存在下，经过不对称共轭加成反应得到酮类化合物3。反应方程式如下：本发明的优势在于：反应原料易得，催化剂结构简单，催化效率高，反应条件温和，后处理简单。
• Synthesis of Pyridine-Dicarboxamide-Cyclohexanone Derivatives: Anticancer and α-Glucosidase Inhibitory Activities and In Silico Study
  作者：Abdullah Al-Majid、Mohammad Islam、Saleh Atef、Fardous El-Senduny、Farid Badria、Yaseen Elshaier、M. Ali、Assem Barakat、A. Motiur Rahman

  DOI：10.3390/molecules24071332

  日期：——

  An efficient and practical method for the synthesis of 2,6-diaryl-4-oxo-N,N′-di(pyridin-2-yl)cyclohexane-1,1-dicarboxamide is described in this present study, which occurs through a double Michael addition reaction between diamide and various dibenzalacetones. The reaction was carried out in dichloromethane (DCM) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The anticancer activities of the synthesized compounds were evaluated in several cancer cell lines, including MCF-7, MDA-MB-231, SAS, PC-3, HCT-116, HuH-7 and HepG2 cells. From these experiments, we determined that MDA-MB-231 was the most sensitive cancer cell line to the compounds 3c, 3e, 3d, 3j and 3l, which exhibited variable anticancer activities (3l [IC50 = 5 ± 0.25 µM] > 3e [IC50 = 5 ± 0.5 µM] > 3c [IC50 = 7 ± 1.12 µM] > 3d [IC50 = 18 ± 0.87 µM] > 3j [IC50 = 45 ± 3 µM]). Of these, 3l (substituted p-trifluoromethylphenyl and chloropyridine) showed good potency (IC50 = 6 ± 0.78 µM) against HCT-116 colorectal cancer cells and exhibited high toxicity against HuH-7 liver cancer cells (IC50 = 4.5 ± 0.3 µM). These values were three times higher than the values reported for cisplatin (IC50 of 8 ± 0.76 and 14.7 ± 0.5 µM against HCT-116 and HuH-7 cells, respectively). The highest α-glucosidase inhibitory activity was detected for the 3d, 3i and 3j compounds. The details of the binding mode of the active compounds were clarified by molecular docking studies.

  本研究描述了一种高效实用的方法，用于合成2,6-二芳基-4-氧代-N,N′-二(吡啶-2-基)环己烷-1,1-二甲酰胺，该方法通过二酰胺与各种二苯乙酮之间的双Michael加成反应实现。反应在二氯甲烷（DCM）中，在1,8-二氮杂双环[5.4.0]十一烯（DBU）存在下进行。评估了合成化合物在几种癌细胞系中的抗癌活性，包括MCF-7、MDA-MB-231、SAS、PC-3、HCT-116、HuH-7和HepG2细胞。从这些实验中，我们确定MDA-MB-231对化合物3c、3e、3d、3j和3l表现出最敏感的抗癌活性，这些化合物表现出不同的抗癌活性（3l [IC50 = 5 ± 0.25 µM] > 3e [IC50 = 5 ± 0.5 µM] > 3c [IC50 = 7 ± 1.12 µM] > 3d [IC50 = 18 ± 0.87 µM] > 3j [IC50 = 45 ± 3 µM]）。其中，3l（取代p-三氟甲基苯基和氯吡啶）对HCT-116结肠癌细胞显示出良好的效力（IC50 = 6 ± 0.78 µM），并对HuH-7肝癌细胞表现出高毒性（IC50 = 4.5 ± 0.3 µM）。这些值比顺铂报告的值高三倍（分别为HCT-116和HuH-7细胞的IC50分别为8 ± 0.76和14.7 ± 0.5 µM）。化合物3d、3i和3j显示出最高的α-葡萄糖苷酶抑制活性。通过分子对接研究澄清了活性化合物的结合模式细节。