4-chloro-4'-ethynylbiphenyl | 57399-11-8

• 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: 4-chloro-4'-ethynylbiphenyl
• 英文别名: 4-chloro-4′-ethynyl-1,1′-biphenyl；4-chloro-4’-ethynyl-1,1’-biphenyl；4'-Chlor-4-ethinyl-biphenyl；4-Chloro-4'-ethynyl-1,1'-biphenyl；1-chloro-4-(4-ethynylphenyl)benzene
• CAS: 57399-11-8
• 化学式: C₁₄H₉Cl
• 分子量: 212.678
• InChiKey: SAIYZSYSSLLGMS-UHFFFAOYSA-N

物化性质

• 沸点：
  317.8±25.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  4-chloro-4'-ethynylbiphenyl 在 palladium diacetate 、 一氯化碘 、 三(2,6-二甲氧基苯基)磷 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 6-(4'-chlorobiphenyl-4-yl)-5-iodo-4-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Discovery of a novel series of N -hydroxypyridone derivatives protecting astrocytes against hydrogen peroxide-induced toxicity via improved mitochondrial functionality

  摘要：

  Astrocytes play a key role in brain homeostasis, protecting neurons against neurotoxic stimuli such as oxidative stress. Therefore, the neuroprotective therapeutics that enhance astrocytic functionality has been regarded as a promising strategy to reduce brain damage. We previously reported that ciclopirox, a well-known antifungal N-hydroxypyridone compound, protects astrocytes from oxidative stress by enhancing mitochondrial function. Using the N-hydroxypyridone scaffold, we have synthesized a series of cytoprotective derivatives. Mitochondrial activity assay showed that N-hydroxypyridone derivatives with biphenyl group have comparable to better protective effects than ciclopirox in astrocytes exposed to H2O2. N-hydroxypyridone derivatives, especially 11g, inhibited membrane-induced deterioration of mitochondrial membrane potential and oxygen consumption rate, and significantly improved cell viability of astrocytes. The results indicate that the N-hydroxypyridone motif can provide a novel cytoprotective scaffold for astrocytes via enhancing mitochondrial functionality. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.12.052
• 作为产物：
  描述：

  4'-氯联苯-4-甲醛 在 二乙胺基三氟化硫 、 叠氮基三甲基硅烷 、 二正丁基氧化锡 、 三乙胺 、 N,N-二异丙基乙胺 、 柠檬酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 4-chloro-4'-ethynylbiphenyl
  参考文献：
  名称：

  α-羟基-四唑作为潜在的乙炔基部分：机理研究。

  摘要：

  本文着重于α-羟基四唑的脱水，导致四氮杂富烯，然后再通过Fritsch–Buttenberg–Wiechell重排而重排成乙炔基的乙烯基卡宾。通过检查底物和/或脱水剂的范围，或通过AM1计算，仔细检查该序列的每个步骤，以了解该方法的限制步骤。这种低估的转化似乎是用于将醛转化为炔烃的现有方法的可行替代方案。

  DOI：

  10.1002/ejoc.201800143

文献信息

• Chemodivergent Synthesis of One-Carbon-Extended Alcohols via Copper-Catalyzed Hydroxymethylation of Alkynes with Formic Acid
  作者：Xin Jin、Hong-Chen Fu、Mei-Yan Wang、Shouying Huang、Yue Wang、Liang-Nian He、Xinbin Ma

  DOI：10.1021/acs.orglett.1c01473

  日期：2021.7.2

  efficient synthesis of alcohols is a long-standing goal of chemical research. Here an intriguing strategy for the chemodivergent copper-catalyzed hydroxymethylation of alkynes with formic acid and hydrosilane has been developed. By simply tuning the amount of formic acid and reaction temperature, distinct one-carbon-extended primary alcohols, that is, allylic alcohols and β-branched alkyl alcohols, were

  开发利用容易获得的试剂有效合成醇的选择性催化反应是化学研究的一个长期目标。这里开发了一种有趣的策略，用于化学发散的铜催化炔烃与甲酸和氢硅烷的羟甲基化。通过简单地调整甲酸的量和反应温度，可以生产出具有高水平 Z/E-、区域-和对映选择性的不同的单碳扩展伯醇，即烯丙醇和 β-支链烷基醇。
• Copper‐Catalyzed and Proton‐Directed Selective Hydroxymethylation of Alkynes with CO ₂
  作者：Mei‐Yan Wang、Xin Jin、Xiaofei Wang、Shumei Xia、Yue Wang、Shouying Huang、Ying Li、Liang‐Nian He、Xinbin Ma

  DOI：10.1002/anie.202012768

  日期：2021.2.19

  strategy for copper‐catalyzed hydroxymethylation of alkynes with CO2 and hydrosilane was developed. Switched on/off a proton source, for example, tBuOH, direct hydroxymethylation and reductive hydroxymethylation could be triggered selectively, delivering a series of allylic alcohols and homobenzylic alcohols, respectively, with high levels of Z/E, regio‐ and enantioselectivity. Such a selective synthesis

  提出了一种用CO 2和氢硅烷对炔烃进行铜催化的羟甲基化的有趣策略。开启/关闭质子源（例如t BuOH）时，可以选择性地触发直接羟甲基化和还原性羟甲基化，分别提供一系列Z / E，区域和对映选择性高的烯丙基醇和高苄基醇。这种选择性合成归因于乙烯基铜中间体对质子和CO 2的响应差异。已证明乙烯基铜物质的质子化在羟甲基化之前，因此允许在合适的质子存在下从直接炔烃羟甲基化转移至还原性羟甲基化。
• Synthesis of Aryl Carboxylic Acids through Ambient Electro-oxidation of Arylacetylenes
  作者：Yanhua Zhang、Hongyan Yuan、Manxin Sun、Tong Zhang、Guohao Wu

  DOI：10.1055/s-0041-1738456

  日期：2024.1

  An efficient and environment-friendly synthesis of aryl carboxylic acids through the ambient electro-oxidation of the arylacetylenes is demonstrated. The reaction proceeds smoothly at certain applied potentials in a mixed solution of acetonitrile and water with potassium peroxymonosulfate (Oxone) as the additive. The isolated yields of the desired products are good up to 90%, and the reaction exhibits

  证明了通过芳基乙炔的环境电氧化有效且环境友好地合成芳基羧酸。在乙腈和水的混合溶液中，以过一硫酸钾（Oxone）为添加剂，反应在一定的外加电位下顺利进行。目标产物的分离收率高达90%，并且反应表现出优异的官能团耐受性。在该电化学系统中，不需要过渡金属催化剂、额外的酸/碱和高温。该方法可能开辟一条通过电化学策略合成羧酸的途径。
• Ambient Semi‐Hydrogenation of Terminal Alkynes with NaBH4 Catalyzed by Palladium Nanowires
  作者：Ying Wang、Mengyuan Ji、Guohao Wu、Yawen Wang、Yanhua Zhang

  DOI：10.1002/cctc.202400951

  日期：2024.11.11

  The semi-hydrogenation of terminal alkynes is successfully achieved with NaBH4 catalyzed by recyclable palladium nanowires (PdNWs) under ambient conditions. With only 0.32 mol % of catalyst loading, the reaction gives the hydrogenated products with up to 98 % overall yields, in which 97 % are semi-hydrogenated products. The method expands the application of metal nanomaterials in organic syntheses

  在环境条件下，用可回收钯纳米线 （PdNW） 催化的 NaBH4 成功实现了末端炔烃的半氢化。只需 0.32 mol % 的催化剂负载量，该反应即可使氢化产物的总产率高达 98%，其中 97% 是半氢化产物。该方法扩展了金属纳米材料在有机合成中的应用。
• Synthesis and Antiplasmodial Activity of New Indolone <i>N</i>-Oxide Derivatives
  作者：Françoise Nepveu、Sothea Kim、Jeremie Boyer、Olivier Chatriant、Hany Ibrahim、Karine Reybier、Marie-Carmen Monje、Severine Chevalley、Pierre Perio、Barbora H. Lajoie、Jalloul Bouajila、Eric Deharo、Michel Sauvain、Rachida Tahar、Leonardo Basco、Antonella Pantaleo、Francesco Turini、Paolo Arese、Alexis Valentin、Eloise Thompson、Livia Vivas、Serge Petit、Jean-Pierre Nallet

  DOI：10.1021/jm901300d

  日期：2010.1.28

  A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), its well as for cytotoxic concentration (CC50) on MCF7 and KB human tumor Cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (< 3 nM on FcB1 and = 1.7 nM on 3D7) with a very satisfactory selectivity index (CC50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day.