(E)-5-(4-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione | 72610-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-(4-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione
• CAS: 72610-53-8
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: FUSGOCNZQHXDTJ-JXMROGBWSA-N

物化性质

• 熔点：
  126.5-127.0 °C
• 沸点：
  475.5±30.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-(4-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione 在 一水合肼 、 溶剂黄146 作用下， 以84%的产率得到(E)-3-(4-methoxystyryl)-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

  摘要：

  A click-type entry into shortened curcuminoids of the diarylpentanoid type has been developed. The reaction is ideally suited to generate non-symmetrical analogues of curcumin, a class of natural products difficult to access but of growing biomedical relevance and special mechanistic interest to investigate the unique binding mode of curcumin to tubulin. Investigation of a series of click diarylpentane curcuminoids and their pyrazole adducts in various cellular tubulin functional assays validated this class of compounds as a novel type of anti-mitotic agents, evidencing structure-activity relationships, and identifying the pyrazole adduct 4k as a promising lead. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.053
• 作为产物：
  描述：

  2,2-Dimethyl-6-(4-methoxystyryl)-4-phenyl-1,3-dioxenilium perchlorate 在 水 、 sodium acetate 作用下， 以 丙酮 为溶剂， 以85%的产率得到(E)-5-(4-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione
  参考文献：
  名称：

  Olekhnovich; Arsen'ev; Borodkin, Russian Journal of Organic Chemistry, 1997, vol. 33, # 8, p. 1160 - 1166

  摘要：

  DOI：

文献信息

• Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation
  作者：Yan-Cheng Liou、Yin-Hsiang Su、Kuan-Chun Ku、Athukuri Edukondalu、Chun-Kai Lin、You-Syuan Ke、Praneeth Karanam、Chia-Jui Lee、Wenwei Lin

  DOI：10.1021/acs.orglett.9b03116

  日期：2019.10.18

  We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products

  我们报告了膦酰化的α，β-不饱和1，3-二酮与酰氯和碱的直接β-酰化作用。根据我们的方案，肉桂酸和酰氯通过β-酰化反应也可以制备官能化的呋喃酮。我们的研究表明，在第二位带有给电子基团的α，β-不饱和1,3-二酮有利于β-酰化产物的形成，而那些具有氧的物质（如酸酐）则通过空前的C-酰化促进呋喃酮的形成。 /环化顺序。
• 1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles
  作者：Vladislav Yu. Korotaev、Nikolay S. Zimnitskiy、Andrey D. Denikaev、Alexey Yu. Barkov、Igor B. Kutyashev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1007/s10593-021-02871-0

  日期：2021.1

  The three-component reaction of (E)-1,5-diarylpent-4-ene-1,3-diones, isatins, and (thia)proline in i-PrOH at room temperature proceeds regio- and stereoselectively leading to the formation of spiro[(thia)pyrrolizidine-3,3'-oxindoles] with the 1,3-dicarbonyl moiety in the (thia)pyrrolizidine ring. Subsequent treatment of these tetracyclic products with arylhydrazine hydrochlorides under reflux in the EtOH–AcOH system gave 5-substituted 1,3-diaryl-1H-pyrazoles in high yields.

  室温下，(E)-1,5-二芳基-4-戊烯-1,3-二酮、异砹和(噻)脯氨酸在 i-PrOH 中发生三组份反应，进行区域和立体选择性反应，生成螺[(噻)吡咯烷-3,3'-氧杂吲哚]，(噻)吡咯烷环中含有 1,3- 二羰基。随后，在 EtOH-AcOH 系统中，在回流条件下用芳基肼盐酸盐处理这些四环产物，高产率地得到了 5-取代的 1,3-二芳基-1H-吡唑。
• An expedient synthesis of novel spiro[indenoquinoxaline-pyrrolizidine]-pyrazole conjugates with anticancer activity from 1,5-diarylpent-4-ene-1,3-diones through the 1,3-dipolar cycloaddition/cyclocondensation sequence
  作者：Nikolay S. Zimnitskiy、Alexey Yu. Barkov、Maria V. Ulitko、Igor B. Kutyashev、Vladislav Yu. Korotaev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1039/d0nj02817g

  日期：——

  in an acidic medium, the 2′-(1,3-diaryl-1H-pyrazol-5-yl)-1′-arylspiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizidines] were formed as individual regioisomers. In a similar reaction with hydrazine hydrate and hydroxylamine, the corresponding hybrids bearing the N-unsubstituted pyrazole and isoxazole moieties were obtained. Most of spiro[indenoquinoxaline-pyrrolizidine]-N-arylpyrazole conjugates have shown

  从11 H-茚并[1,2- b ]喹喔啉-11-one和L-脯氨酸/硫代脯氨酸原位生成的偶氮甲亚胺的内基-1,3-偶极环加成反应生成（E）-1,5-二芳基戊-4-烯-1,3-二酮导致3-羟基-3-芳基-1-（1'-芳基螺[茚并[1,2 - b ]喹喔啉-11,3 '-（硫杂吡咯啉）-2'- yl）prop-2- en -1，含有1,3-二酮片段。在酸性介质中用芳基肼盐酸盐处理这些加合物时，2'-（（1,3-二芳基-1 H-吡唑-5-基）-1'-芳基螺[茚并[1,2- b]作为单独的区域异构体形成了[喹喔啉-11,3'-吡咯嗪核苷]。在与水合肼和羟胺的类似反应中，获得了带有N-未取代的吡唑和异恶唑部分的相应杂化物。大部分螺[茚并喹喔啉-吡咯烷核] -N-芳基吡唑结合物已显示出对HeLa癌细胞系的高细胞毒性活性。
• Highly diastereoselective annulation of 2-substituted 3-nitro-2<i>H</i>-chromenes with hemicurcuminoids and curcuminoids <i>via</i> a double and triple Michael reaction cascade
  作者：Nikolay S. Zimnitskiy、Alexey Yu. Barkov、Ivan A. Kochnev、Igor B. Kutyashev、Vladislav Yu. Korotaev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1039/d2nj02019j

  日期：——

  72 h in the presence of Cs2CO3 proceeds by way of a triple Michael/Michael/oxa-Michael cascade leading to 3,6-diaryl-6a-nitro-2,3,5,6a,7,12b-hexahydro-1H,6H-chromeno[6,5-c]chromen-1-ones in 71–97% yields. 2-Phenyl-2-(trifluoromethyl)-3-nitro-2H-chromenes under the analogous conditions react with enediones to form 2-(2-phenyl-2-(trifluoromethyl)-2H-chromen-4-yl)-1,5-diarylpent-4-ene-1,3-diones as a result

  K 2 CO 3催化的 ( E )-1,5-二芳基-和 1-烷基-5-芳基戊-4-烯-1,3-二酮与 2-三氟甲基-和 2-苯基-取代的双迈克尔加成3-nitro-2 H -chromenes 在二氯甲烷中在室温下放置 48 小时，生成 10-aroyl(acyl)-7-aryl-6a-nitro-6,6a,7,8,10,10a-hexahydro-9 H -苯并[ c ]chromen-9-ones 以 75–98% 的产率作为单独的非对映异构体在 C-6、C-6a 和 C-7 原子和 H-9b 原子上相对于稠合三环体系具有顺式排列的取代基. 在 Cs 2 CO 3存在下，类姜黄素在氯仿中回流 72 小时的类似立体选择性过程通过三重 Michael/Michael/oxa-Michael 级联产生 3,6-diaryl-6a-nitro-2,3,5,6a,7,12b-hexahydro-1
• Venugopalan, P.; Krishnankutty, K., Journal of the Indian Chemical Society, 1998, vol. 75, # 2, p. 98 - 99
  作者：Venugopalan, P.、Krishnankutty, K.

  DOI：——

  日期：——