1,5-Bis(3-fluorophenyl)-1,4-pentadien-3-one | 916427-65-1

• 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(3-fluorophenyl)-1,4-pentadien-3-one
• 英文别名: 1,5-bis(3-fluorophenyl)penta-1,4-dien-3-one
• CAS: 916427-65-1
• 化学式: C₁₇H₁₂F₂O
• 分子量: 270.278
• InChiKey: YDABOWAAEKQQKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 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：
  3

反应信息

• 作为反应物：
  描述：

  1,5-Bis(3-fluorophenyl)-1,4-pentadien-3-one 在 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 反应 0.05h， 以88%的产率得到1-[3-(3-fluorophenyl)-5-[2-(3-fluorophenyl)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：

  丙酮 、 3-氟苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 1,5-Bis(3-fluorophenyl)-1,4-pentadien-3-one
  参考文献：
  名称：

  通过氮杂迈克尔加成/亲核加成/脱氢级联反应合成2-氨基-4-芳基-6-苯乙烯基嘧啶

  摘要：

  描述了一种通过各种二苯乙烯基酮与盐酸胍通过氮杂-迈克尔加成/亲核加成/脱氢级联过程反应合成2-氨基-4-芳基-6-苯乙烯基嘧啶的有效方法。该方案的显着特点是底物易得、无过渡金属体系、反应条件温和、原子经济性高、底物范围广、收率满意、后处理程序简单。

  DOI：

  10.1002/jhet.4731

文献信息

• 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。
• A highly organocatalytic stereoselective double Michael reaction: efficient construction of optically enriched spirocyclic oxindoles
  作者：Liang-Liang Wang、Lin Peng、Jian-Fei Bai、Li-Na Jia、Xi-Ya Luo、Qing-Chun Huang、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1039/c1cc11223f

  日期：——

  An array of spirocyclic oxindoles have been constructed via a double Michael reaction in high yields and excellent enantioselectivities.

  一系列螺环氧吲哚化合物已经通过双Michael反应高产率和优异对映选择性构建。
• Asymmetric Double Michael Reaction Catalyzed by Simple Primary Amine Catalysts: A Straightforward Approach to Construct Spirocyclic Oxindoles
  作者：Xiya Luo、Liangliang Wang、Lin Peng、Jianfei Bai、Lina Jia、Guangyun He、Fang Tian、Xiaoying Xu、Lixin Wang

  DOI：10.1002/cjoc.201100543

  日期：2012.5

  The enantioselective double Michael reaction of N‐Boc‐3‐nonsubstitued oxindoles with dienones catalyzed by chiral monoimide protected cyclohexane‐1,2‐diamines was developed. A wide range of optically active spirocyclic oxindoles were obtained up to 98% yield and up to 89% ee.

  开发了N ‐Boc‐3‐取代的吲哚与手性单酰亚胺保护的环己烷‐1,2‐二胺催化的二烯酮的对映选择性双Michael反应。获得了高达98％的收率和89％ee的多种旋光性螺环羟吲哚。
• Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes
  作者：Ibrahim Jantan、Syed Nasir Abbas Bukhari、Nordin Haji Lajis、Faridah Abas、Lam Kok Wai、Malina Jasamai

  DOI：10.1111/j.2042-7158.2011.01423.x

  日期：2012.2.6

  A series of 43 curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on the chemiluminescence and chemotactic activity of phagocytes in vitro.

  The effects of the compounds on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) were evaluated using a luminol-based chemiluminescence assay and their effect on chemotactic migration of PMNs was investigated using the Boyden chamber technique.

  Compounds 6, 17, 25 and 30 exhibited significant inhibitory activity on the oxidative burst of PMNs. The presence of methoxy groups at positions 2 and 5, and methoxylation and fluorination at positions 4 and 2 of both phenyl rings, respectively, may contribute significantly to their reactive oxygen species inhibition activity. Compounds 7, 17, 18, 24 and 32 showed strong inhibition of the chemotaxis migration of PMNs. Chlorination at various positions of both phenyl rings of cyclohexanone diarylpentanoid resulted in compounds with potent inhibitory effects on PMN migration.

  The results suggest that some of these diarylpentanoid analogues are able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as a source of new immunomodulatory agents.

  摘要 目的 合成了一系列43个姜黄素二芳基戊酮类似物，并评估它们对体外吞噬细胞化学发光和趋化活性的抑制作用。 方法 使用基于流明的化学发光测定法评估化合物对人全血和分离的人多形核白细胞（PMNs）呼吸爆发的影响，并利用Boyden室技术研究它们对PMNs趋化迁移的影响。 主要发现 化合物6、17、25和30在PMNs的氧化爆发上表现出显著的抑制活性。在两个苯环的2和5位置有甲氧基基团，以及在4和2位置分别有甲氧化和氟化基团的存在，可能会显著促进它们对活性氧化物种的抑制活性。化合物7、17、18、24和32显示出对PMNs趋化迁移的强烈抑制作用。在环己酮二芳基戊酮类似物的两个苯环的不同位置进行氯化，导致化合物对PMN迁移具有强效抑制作用。 结论 结果表明，这些二芳基戊酮类似物中的一些能够调节吞噬细胞的先天免疫反应的不同步骤，强调它们作为新的免疫调节剂来源的潜力。
• Synthesis of Optically Enriched Spirocyclic Benzofuran-2-ones by Bifunctional Thiourea-Base Catalyzed Double-Michael Addition of Benzofuran-2-ones to Dienones
  作者：Xin Li、Chen Yang、Jia-Lu Jin、Xiao-Song Xue、Jin-Pei Cheng

  DOI：10.1002/asia.201201244

  日期：2013.5

  A highly enantioselective catalytic double‐Michael addition reaction of substituted benzofuran‐2‐ones with divinyl ketones promoted by readily accessible tertiary amine–thiourea Cinchona alkaloids has been developed. A number of optically enriched spirocyclic benzofuran‐2‐ones were prepared in very good yields (up to 99 %), diastereoselectivities (up to 19:1 d.r.), and very good enantioselectivities

  已经开发出一种高度对映选择性的双苯甲酰呋喃-2-酮催化的双迈克尔加成反应与易于获得的叔胺-硫脲金鸡纳生物碱促进的二乙烯基酮。制备了许多光学富集的螺环苯并呋喃-2-酮，具有很高的收率（高达99％），非对映选择性（高达19：1 dr）和非常好的对映选择性（高达92％ee）。进行密度泛函理论（DFT）计算以研究立体选择性的起源。