(Z)-1,4-bis(4-methoxyphenyl)but-2-ene-1,4-dione | 878652-50-7

• 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: (Z)-1,4-bis(4-methoxyphenyl)but-2-ene-1,4-dione
• CAS: 878652-50-7
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: CEXKMZRIOMSVLG-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-1,4-bis(4-methoxyphenyl)but-2-ene-1,4-dione 在 乙酸铵 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 1,3-bis(4-methoxyphenyl)-4,7-dihydro-2H-isoindole
  参考文献：
  名称：

  1,3-Diaryl-4,5,6,7-tetrahydro-2H-isoindole Derivatives:  A New Series of Potent and Selective COX-2 Inhibitors in Which a Sulfonyl Group Is Not a Structural Requisite

  摘要：

  Novel tetrahydro-2H-isoindoles have been prepared and evaluated as inhibitors of the COX-2 isoenzyme. A 1,S-diaryl substitution on the central polycyclic ring system and absence of a sulfonyl moiety are the two structural features of this chemical series. A short and easy synthetic pathway produced several derivatives which were shown to be potent and selective COX-2 vs COX-1 inhibitors (IC50 = 0.6-100 nM for COX-2, 100->1000 nM for COX-1). Structural modifications established that a bicyclic ring appended to the pyrrole nucleus and 4,4'-difluoro substitution on the phenyl rings were optimal for high inhibitory potency. Activity was confirmed in the human whole blood assay and subsequently in the murine air-pouch model in which in vivo PGE2 inhibitory activity was evaluated with respect to gastric tolerance (ED50 for inhibition of exudate PGE2 of 3 mg/kg and gastric PGEB of 20 mg/kg). Gastric tolerance was further assessed after administration to mice of high doses (up to 400 mg/kg) of the inhibitors by measurement of gastric damage. This panel of studies allowed selection of a number of tetrahydro-2H-isoindoles which were compared in the adjuvant-induced arthritis model. Compounds 32 and 37 showed the most potent activity with ED50 values for edema inhibition in the noninjected paw of 0.35 and 0.15 mg/kg/day, respectively, after oral administration. In addition, this interesting antiinflammatory profile was accompanied by a protective effect against arthritis-induced osteopenia, the decrease being 50% with a dose of 0.25 mg/kg/day.

  DOI：

  10.1021/jm990965x
• 作为产物：
  描述：

  反式-1,2-二(4-甲氧基苯甲酰基)乙烯 以 正己烷 、 乙酸乙酯 为溶剂， 反应 5.0h， 以81%的产率得到(Z)-1,4-bis(4-methoxyphenyl)but-2-ene-1,4-dione
  参考文献：
  名称：

  甲酮的高度可调立体选择性二聚：E-和Z -1,4-对映体的高效合成

  摘要：

  描述了一种直接由芳族甲基酮可调谐合成1，4-二烯的新方法。该串联反应使得能够构造具有完全的E-选择性的对称和不对称的1，4-二烯。此外，通过用23W的白光照射，可以将所得的E -1，4-二烯二酮转化为Z-异构体。

  DOI：

  10.1021/ol4006344

文献信息

• Visible-Light-Mediated Oxidative Dimerization of Arylalkynes in the Open Air: Stereoselective Synthesis of (<i>Z</i>)-1,4-Enediones
  作者：Donglei Wei、Fushun Liang

  DOI：10.1021/acs.orglett.6b02926

  日期：2016.11.18

  An organic photoredox catalytic one-pot protocol is developed for the highly stereoselective synthesis of (Z)-1,4-enediones. The reaction starts directly from alkyne precursors, using 4-(4-cyanophenyl)-2,6-diphenylpyrylium tetrafluoroborate (CN-TPT) as an efficient photosensitizer and dioxygen in the air as a green oxidant. A Csp–Csp oxidative coupling/[4 + 2] cyclization (with dioxygen)/fragmentive

  开发了一种有机光氧化还原催化一锅法，用于高度立体选择性地合成（Z）-1,4-二烯酮。该反应直接从炔烃前体开始，使用四氟硼酸4-（4-氰基苯基）-2,6-二苯基吡啶鎓（CN-TPT）作为有效的光敏剂，并在空气中使用双氧作为绿色氧化剂。提出了AC sp –C sp氧化偶合/ [4 + 2]环化（含双氧）/碎片异构化的级联机理。（Z）-1，4-二烯的主要形成归因于来自蓝色LED的有效可见光照明，以及可能的从光敏剂CN-TPT到E-异构体的能量转移。
• Zn^II- and Au^I-Catalyzed Regioselective Hydrative Oxidations of 3-En-1-ynes with Selectfluor: Realization of 1,4-Dioxo and 1,4-Oxohydroxy Functionalizations
  作者：Appaso Mahadev Jadhav、Sagar Ashok Gawade、Dhananjayan Vasu、Ramesh B. Dateer、Rai-Shung Liu

  DOI：10.1002/chem.201304322

  日期：2014.2.10

  Catalytic 1,4‐dioxo functionalizations of 3‐en‐1‐ynes to (Z)‐ and (E)‐2‐en‐1,4‐dicarbonyl compounds are described. This regioselective difunctionalization was achieved in one‐pot operation through initial alkyne hydration followed by in situ Selectfluor oxidation. The presence of pyridine alters the reaction chemoselectivity to give 4‐hydroxy‐2‐en‐1‐carbonyl products instead. A cooperative action of

  描述了3-烯-1-炔对（Z）-和（E）-2-烯-1,4-二羰基化合物的催化1,4-二氧羰基化作用。这种区域选择性的双功能化是通过最初的炔烃水合作用，然后进行原位Selectfluor氧化，通过一锅操作实现的。吡啶的存在会改变反应的化学选择性，从而产生4-羟基-2-en-1-羰基产物。吡啶和Zn II的协同作用有助于关键氧鎓中间体的水解。
• Rotational isomerism in 1,4-diarylbut-2-ene-1,4-dione radical anions: an electron paramagnetic resonance study
  作者：M. Luisa T. M. B. Franco、M. Celina R. L. R. Lazana、Bernardo J. Herold

  DOI：10.1039/ft9928801977

  日期：——

  The radical anions of (Z)- and (E)-1,4-diarylbut-2-ene-1,4-diones 1–8 have been obtained by electrolytic reduction in dimethylformamide. Identical EPR spectra are recorded at room temperature for both the (Z)- and (E)-isomers evidencing rapid (Z)–(E) interconversion. Individual conformers are not observed for radical anions derived from either diphenyl, bis(p-tolyl) or bis(p-anisyl) derivatives 1˙––6˙–

  的自由基阴离子（Ž） -和（Ë）-1,4- diarylbut -2-烯-1,4-二酮1 - 8已经由二甲基甲酰胺电解还原而获得。（Z）-和（E）-异构体在室温下记录到相同的EPR光谱，证明了快速的（Z）-（E）互变。从二苯基，双（对甲苯基）或双（对茴香基）衍生物1 1– – 6 ˙–衍生的自由基阴离子未观察到单个构象异构体在223–298 K的温度范围内。INDO计算理论上支持了可能的构象异构体之间的快速相互转化。为了从二化合物高度应变自由基阴离子8 ˙-三种异构体具有不同的克-值是可区分的。还通过INDO计算指定了不同的异构体。
• Photoredox-Mediated Aerobic Oxidative Cleavage of 1,3-Diketones to Access 1,2-Diketones and (<i>Z</i>)-1,4-Enediones
  作者：Xiaofeng Yu、Nan Huang、Yanping Huo、Xianwei Li、Yan Liu、Keiji Maruoka、Qian Chen

  DOI：10.1021/acs.orglett.3c04247

  日期：2024.1.19

  is disclosed. The newly developed reaction provides practical access to 1,2-diketones and (Z)-1,4-enediones in moderate to good yields with absolute regio- and stereoselectivity. Mechanistic studies of the reaction suggest that tetraketone intermediates might undergo a photocatalytic energy transfer from the excited photocatalyst to form biradical-like (n,π*) states of ketones.

  公开了使用有机染料作为光催化剂在可见光照射下1,3-二酮的有氧氧化裂解。新开发的反应以中等至良好的产率和绝对的区域选择性和立体选择性提供了实际获得 1,2-二酮和 ( Z )-1,4-烯二酮的方法。该反应的机理研究表明，四酮中间体可能会经历激发光催化剂的光催化能量转移，形成酮的双自由基 (n,π*) 态。
• Buchta; Schaeffer, Justus Liebigs Annalen der Chemie, 1955, vol. 597, p. 129,140
  作者：Buchta、Schaeffer

  DOI：——

  日期：——