2,5-二苯基对苯二酚 | 5422-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,5-二苯基对苯二酚
• 中文别名: 2,5-二苯基-1,4-苯二醇；2,5-二苯基氢化喹啉
• 英文名称: 2,5-diphenylhydroquinone
• 英文别名: 2.5-Diphenyl-hydrochinon；2,5-diphenyl-1,4-dihydroxybenzene；2,5-diphenylbenzene-1,4-diol
• CAS: 5422-91-3
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: BVVCBZSERKSMIE-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C
• 沸点：
  486.3±45.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  2,5-二苯基对苯二酚 在 氯仿 、 溴 作用下， 生成 3',6'-dibromo-p-terphenyl-2',5'-diol
  参考文献：
  名称：

  THE SYNTHESIS OF POLYPORIC ACID AND ATROMENTIN DIMETHYL ETHER

  摘要：

  DOI：

  10.1021/ja01357a053
• 作为产物：
  描述：

  苯基-P-苯醌 在 sodium tetrahydroborate 、 palladium(II) trifluoroacetate 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 26.0h， 生成 2,5-二苯基对苯二酚
  参考文献：
  名称：

  Synthesis and evaluation of arylquinones as BACE1 inhibitors, β-amyloid peptide aggregation inhibitors, and destabilizers of preformed β-amyloid fibrils

  摘要：

  BACE1 activity, inhibition of A beta aggregation, and disaggregation of preformed A beta fibrils constitute the three major targets in the development of small-molecule lipophilic new drugs for the treatment of Alzheimer's disease (AD). Quinones are widely distributed among natural products and possess relevant and varied biological activities including antitumor and antibiotic, inhibition of HIV-1 reverse transcriptase, antidiabetic, or COX-inhibition, among others. We report herein the interaction of several arylquinones and their derivatives with the amyloidogenic pathway of the amyloid precursor protein processing. Our studies put forward that these compounds are promising candidates in the development of new drugs which are effective simultaneously towards the three major targets of AD. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.023

文献信息

• Synthesis of new type benzo[<i>b</i>]thiophene fused quinones and their tetracyanoquinodimethane derivatives
  作者：Yoshihiro Ohba、Yasuo Murakami、Tyo Sone、Hiroshi Awano

  DOI：10.1002/jhet.5570340313

  日期：1997.5

  of new type of benzo[b]thiophene-fused 1,4-benzoquinones and their tetracyanoquinodimethane derivatives were synthesized. The cyclic voltammetric data of new type quinones and tetracyanoquinodimethane derivatives displayed different behavior. All new quinones exhibit two reduction waves corresponding to the radical anion and dianion. On the other hand, most tetracyanoquinodimethane derivatives display

  合成了一系列新型的苯并[ b ]噻吩稠合的1,4-苯醌及其四氰基喹二甲烷衍生物。新型醌和四氰基喹二甲烷衍生物的循环伏安数据显示出不同的行为。所有新的醌类均表现出两个还原波，分别对应于自由基阴离子和二阴离子。另一方面，大多数四氰基喹二甲烷衍生物显示出对二价阴离子的单波还原。苯并[ b ]噻吩部分稠合的四氰基喹二甲烷衍生物比四氰基喹二甲烷具有更大的负还原电位。
• On/off electrochemical switches based on quinone-bisketals
  作者：Noelia Fuentes、Luis Álvarez de Cienfuegos、Andrés Parra、Duane Choquesillo-Lazarte、Juan M. García-Ruiz、M. Luisa Marcos、Elena Buñuel、Maria Ribagorda、M. Carmen Carreño、Diego J. Cárdenas、Juan M. Cuerva

  DOI：10.1039/c0cc04388e

  日期：——

  The synthesis and anodic oxidation of a variety of 2,5-diaryl or dialkynylaryl substituted 1,4-dialkoxybenzenes to quinone bisketals is described. The study of the X-ray structures and electrochemical and spectroscopic properties evidenced that these pairs constitute a first approach to the concept of a molecular nanofuse.

  描述了多种2,5-二芳基或二炔基芳基取代的1,4-二烷氧基苯合成及其阳极氧化为醌双酮的过程。X射线结构、 electrochemical和光谱特性的研究表明，这些配体构成了分子纳米保险丝概念的首次尝试。
• Synthesis and characterization of low-birefringent crosslinkable fluorinated poly(arylene ether sulfide)s containing pendant phenyl moiety
  作者：Kwan-Soo Lee、Jae-Pil Kim、Jae-Suk Lee

  DOI：10.1016/j.polymer.2009.12.020

  日期：2010.2

  polymer used and were changed to the range of 191–245 °C after curing. The FPAESIs and E-FPAESIs exhibited high thermal stability up to 445–450 °C and 457–462 °C, respectively. The refractive index and birefringence of spin-coated polymer films were determined by the prism-coupling method. The refractive indices and birefringences of the films were in the range of 1.5849–1.5880 and 0.0014–0.0035 at a 1550 nm

  由制备的二羟基单体与五氟苯基硫化物逐步生长聚合合成氟化聚（亚芳基醚硫化物）（FPAESI）和乙炔基端基的氟化聚（亚芳基醚硫化物）（E-FPAESI），然后E-FPAESI继而与3-乙炔基苯酚。FPAESI和E-FPAESI的数均分子量和多分散性分别在12,000–26,000和1.75–3.18之间。聚合物的玻璃化转变温度在138至178°C之间变化，具体取决于所用聚合物的分子量，固化后改变为191–245°C。FPAESI和E-FPAESI分别在高达445–450°C和457–462°C的温度下具有较高的热稳定性。通过棱镜耦合法测定旋涂的聚合物膜的折射率和双折射。薄膜在1550 nm波长处的折射率和双折射分别在1.5849-1.5880和0.0014-0.0035范围内。将E-FPAESI结构对双折射的影响与各种已报道的聚亚芳基醚硫化物进行了比较。
• Syntheses of Tetrasubstituted [10]Cycloparaphenylenes by a Pd‐catalyzed Coupling Reaction. Remarkable Effect of Strain on the Oxidative Addition and Reductive Elimination
  作者：Eiichi Kayahara、Masaya Nakano、Liansheng Sun、Kosuke Ishida、Shigeru Yamago

  DOI：10.1002/asia.202000711

  日期：2020.8.17

  A small library of tetrasubstituted [10]cycloparaphenylene ([10]CPP) derivatives bearing alkyl, alkenyl, alkynyl and aryl substituents was constructed by a Pd‐catalyzed cross‐coupling reaction starting from tetratriflate [10]CPP 5 e, which was readily available in high yields on a >2 g scale. The CPP skeleton increases the reactivity of aryl triflate for oxidative addition to the Pd species, and 5 e

  四取代的[10]环的一小库（[10] CPP）衍生物轴承烷基，烯基，炔基和芳基取代基是通过从tetratriflate [10] CPP开始Pd-催化的交叉偶联反应构建5  ë，这是容易获得的> 2 g规模的高产量。该CPP骨架增加芳基三氟甲磺酸酯的反应性的氧化除钯物种，和5  ë是10倍比其线性对苯类似物更具反应性的，如通过竞争实验来确定。理论计算表明，未参与反应的每个对亚苯基单元产生的小的应变释放的累积是观察到的增强的反应性的原因。
• Anti-proliferative Activities towards Human Brain Glioma U251 Cells and Human Carcinoma Cells (KB3-1) of Some Twin-Drug Type Bivalent &lt;i&gt;C&lt;/i&gt;&lt;sub&gt;2&lt;/sub&gt;-Symmetrical Phenylboronic Acid Derivatives
  作者：Makoto Furutachi、Toshiaki Gondo、Ryuji Ikeda、Naoki Yoshikawa、Tsubasa Yokota、Yasuo Takeda、Kazumi Yokomizo、Jian-Rong Zhou、Nobuhiro Kashige、Fumio Miake、Kunihiro Sumoto

  DOI：10.1248/bpb.b18-00859

  日期：2019.5.1

  Derivatives of C2-symmetrical bivalent phenylboronic acid exhibit several remarkable biological activities such as anti-herpes simplex virus (HSV)-1 and cytotoxic activities against Vero cells and they can reverse the effect of anticancer drugs. Novel symmetrical bivalent molecules were synthesized and their biological activities were evaluated in vitro using a human brain glioma cell line (U251) and a human carcinoma cell line (KB3-1). Among the tested compounds (1a–i), bivalent C2-symmetrical phenylboronic acid derivative 1g showed the highest anti-proliferative activity towards both U251 and KB3-1 cells. The values of 50% anti-proliferative activity (IC50) of this compound against the two cell lines (U251 and KB3-1) were 19.0 and 3.78 µM, respectively. The anti-proliferative activity of compound 1g towards KB3-1 cells was higher than that of cisplatin. The bivalent C2-symmetrical compound 1g had a linear methylene linker in the molecule.

  C2对称二价苯硼酸衍生物具有多种显著的生物活性，例如抗单纯疱疹病毒（HSV）-1和针对Vero细胞的细胞毒性，它们可以逆转抗癌药物的作用。研究人员合成了新型对称二价分子，并使用人脑胶质瘤细胞系（U251）和人癌细胞系（KB3-1）对其生物活性进行了体外评估。在测试的化合物（1a-i）中，二价C2对称苯硼酸衍生物1g对U251和KB3-1细胞具有最高的抗增殖活性。该化合物对两种细胞系（U251和KB3-1）的50%抗增殖活性（IC50）值分别为19.0和3.78微摩尔。化合物1g对KB3-1细胞的抗增殖活性高于顺铂。二价C2对称化合物1g在分子中具有线性亚甲基连接。