1,5-bis(2-methoxyphenyl)penta-1,4-dien-3-one | 41973-42-6

• 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-methoxyphenyl)penta-1,4-dien-3-one
• CAS: 41973-42-6
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: RCZMPCUUTSDNAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  127 °C
• 沸点：
  467.2±40.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,5-bis(2-methoxyphenyl)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90%的产率得到1-[3-(2-Methoxyphenyl)-5-[2-(2-methoxyphenyl)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：

  (1E,4E)-1,5-二(2-羟基苯基)戊-1,4-二烯-3-酮 生成 1,5-bis(2-methoxyphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Heilbron; Forster, Journal of the Chemical Society, 1924, vol. 125, p. 2066

  摘要：

  DOI：

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。
• Synthesis of 4-arylethyl-6-arylpyrimidine-2-thiols through aza-Michael addition/nucleophilic addition/aromatization tandem reactions
  作者：Zheng Li、Wenli Song、Jiaojiao He、Yan Du、Jingya Yang

  DOI：10.1515/hc-2017-0169

  日期：2018.2.23

  Abstract An efficient method for the synthesis of the title compounds by reactions of divinyl ketones with thiourea is described. This protocol has the advantages of high yields, mild reaction conditions and simple work-up procedure.

  摘要 描述了一种通过二乙烯基酮与硫脲反应合成标题化合物的有效方法。该方案具有收率高、反应条件温和、后处理程序简单等优点。
• Curcumin analogs with anti-tumor and anti-angiogenic properties
  申请人：——

  公开号：US20020019382A1

  公开（公告）日：2002-02-14

  The present invention is directed to curcumin analogs exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

  本发明涉及表现出抗肿瘤和抗血管生成特性的姜黄素类似物，包括这些化合物的药物配方以及使用这些化合物的方法。
• An Efficient Synthesis of 1,5-Diaryl-1,4-pentadien-3-one Oxime in the Presence of Anhydrous Sodium Sulfate
  作者：Ji-Tai Li、Xin-Li Zhai、Bo Bai、Yan-Hua Liang

  DOI：10.2174/157017810791130676

  日期：2010.6.1

  A series of 1,5-diaryl-1,4-pentadien-3-one oximes were synthesized via the reaction of 1,5-diaryl-1,4- pentadien-3-one with hydroxylamine hydrochloride in the presence of anhydrous sodium sulfate at refluxing EtOH to give good yields. This method provided several advantages such as shorter reaction time and higher yield.

  一系列1,5-二芳基-1,4-戊二烯-3-酮肟通过在回流乙醇中，无水硫酸钠存在下，1,5-二芳基-1,4-戊二烯-3-酮与盐酸羟胺反应合成，产率良好。该方法具有反应时间短、产率高等优点。
• 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。