(Z)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione | 27297-60-5

• 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-chlorophenyl)but-2-ene-1,4-dione
• 英文别名: 1.4-bis-(4-chloro-phenyl)-butene-(2c)-dione-(1.4)；1.4-Bis-(4-chlor-phenyl)-buten-(2c)-dion-(1.4)；cis-1,4-Bis-(4-chlor-phenyl)-but-2-en-1,4-dion；cis-1,2-Di-p-chlorbenzoyl-aethylen；1,2-Bis-(p-chlorbenzoyl)-ethylen；cis-1,2-Di-p-chlorbenzoylethylen；cis-1,2-Di-p-chlorobenzoylethylene
• CAS: 27297-60-5
• 化学式: C₁₆H₁₀Cl₂O₂
• 分子量: 305.16
• InChiKey: NOWZMUNUVDBDQQ-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione 在 碘 作用下， 生成 (E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione
  参考文献：
  名称：

  Hadjoudis,E., Israel Journal of Chemistry, 1973, vol. 11, p. 63 - 69

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯仿 作用下， 生成 (Z)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione
  参考文献：
  名称：

  Conant; Lutz, Journal of the American Chemical Society, 1923, vol. 45, p. 1305

  摘要：

  DOI：

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。
• Reduction of 1 : 4-Diketones
  作者：NEIL CAMPBELL、NANDOOMAL KHANNA

  DOI：10.1038/161054a0

  日期：1948.1

  desirable, especially since 1 : 6-addition is comparatively uncommon3. We have done this by reducing several substituted dibenzoylethylenes with aluminium isopropoxide in isopropyl alcohol, a reagent known to attack carbonyl groups while leaving olefinic linkages intact. The reduction products were invariably the corresponding diphenacyls, identified (after chromatographic adsorption) by mixed melting points

  二苯甲酰乙烯在某些条件下用金属组合还原或催化氢化产生相应的二苯甲酰基，并且有证据表明该反应通过氢的 1:6-加成和中间体二烯醇的快速酮化发生。Lutz 和 Reveley2 显示了一种这样的二烯醇的存在，但是没有将其分离：需要确认这种机制，特别是因为 1:6 加成相对不常见。我们已经通过在异丙醇中用异丙醇铝还原几个取代的二苯甲酰亚乙基来实现这一点，异丙醇是一种已知的试剂，可以攻击羰基，同时保持烯键完整。还原产物总是相应的二苯甲酰，通过与真实样品的混合熔点进行鉴定（色谱吸附后）。
• 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。
• Chemical Strategies to Diversification of the Mechanical Properties of Organic Crystals
  作者：Shuting Dai、Jiangbin Zhong、Xiqiao Yang、Chao Chen、Liping Zhou、Xinyu Liu、Jingbo Sun、Kaiqi Ye、Hongyu Zhang、Liang Li、Pance Naumov、Ran Lu

  DOI：10.1002/anie.202320223

  日期：——

  This study demonstrates the effects of halogenation on the mechanical and photomechanical behavior of organic crystals. Starting with (E)-1,4-diphenylbut-2-ene-1,4-dione, the brittle photoinert crystals evolve into mechanically flexible, photochemically reactive crystals via double and quadruple halogenation, an approach that advocates for combined chemical and crystal engineering strategies to determine

  这项研究证明了卤化对有机晶体的机械和光机械行为的影响。从 ( E )-1,4-二苯基丁-2-烯-1,4-二酮开始，脆性光惰性晶体通过双卤化和四卤化演变成机械柔性、光化学反应性晶体，这是一种提倡化学和晶体工程相结合的方法确定决定固态响应动力学的关键因素的策略。
• 1,3-Diaryl-4,5,6,7-tetrahydro-2<i>H</i>-isoindole Derivatives:  A New Series of Potent and Selective COX-2 Inhibitors in Which a Sulfonyl Group Is Not a Structural Requisite
  作者：Bernard Portevin、Charles Tordjman、Philippe Pastoureau、Jacqueline Bonnet、Guillaume De Nanteuil

  DOI：10.1021/jm990965x

  日期：2000.11.1

  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.