1,3-bis(phenylethynyl)benzene | 13141-36-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,3-bis(phenylethynyl)benzene
• 英文别名: 1,3-bis(2-phenylethynyl)benzene；1,3-bis(ethynylphenyl)benzene
• CAS: 13141-36-1
• 化学式: C₂₂H₁₄
• 分子量: 278.353
• InChiKey: OYEDTTNTNYKSFX-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  464.6±28.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• 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

反应信息

• 作为反应物：
  描述：

  1,3-bis(phenylethynyl)benzene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、250.0 kPa 条件下， 以99%的产率得到1,3-双(2-苯基乙基)苯
  参考文献：
  名称：

  Strategies To Reduce hERG K⁺Channel Blockade. Exploring Heteroaromaticity and Rigidity in Novel Pyridine Analogues of Dofetilide

  摘要：

  Drug-induced blockade of the human ether-a-go-go-related gene K+ channel (hERG) represents one of the major antitarget concerns in pharmaceutical industry. SAR studies of this ion channel have shed light on the structural requirements for hERG interaction but most importantly may reveal drug design principles to reduce hERG affinity. In the present study, a novel library of neutral and positively charged heteroaromatic derivatives of the class III antiarrhythmic agent dofetilide was synthesized and assessed for hERG affinity in radioligand binding and manual patch clamp assays. Structural modifications of the pyridine moiety, side chain, and peripheral aromatic moieties were evaluated, thereby revealing approaches for reducing hERG binding affinity. In particular, we found that the extra rigidity imposed close to the positively charged pyridine moiety can be very efficient in decreasing hERG affinity.

  DOI：

  10.1021/jm301564f
• 作为产物：
  描述：

  三苯基铋 、 1,3-双(2,2-二溴乙烯基)苯 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以73%的产率得到1,3-bis(phenylethynyl)benzene
  参考文献：
  名称：

  Pd-Catalyzed Domino Synthesis of Internal Alkynes Using Triarylbismuths as Multicoupling Organometallic Nucleophiles

  摘要：

  The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles with 3 equiv of 1,1-dibromo-1alkenes are very fast, affording high yields of alkynes in a short reaction time. Thus, an efficient domino process has been accomplished using 1,1-dibromo-1-alkenes as surrogates for internal alkyne synthesis in couplings with triarylbismuths in a one-pot operation.

  DOI：

  10.1021/ol1004164

文献信息

• Supported palladium nanoparticles-catalyzed decarboxylative coupling approaches to aryl alkynes, indoles and pyrrolines synthesis
  作者：C. Bal Reddy、Richa Bharti、Sandeep Kumar、Pralay Das

  DOI：10.1039/c6ra12046f

  日期：——

  The polystyrene supported palladium (Pd@PS) nanoparticles (NPs) catalyzed decarboxylative coupling (DC) of arylhalides and alkynyl carboxylic acids was developed for the synthesis of diaryl alkynes. Indole and 3-pyrroline heterocycles were also synthesized from 2-iodo anilines/amino benzocycloheptene bromide and alkynyl carboxylic acids, following a domino decarboxylative coupling-cyclization (DCC)

  聚苯乙烯负载的钯（Pd @ PS）纳米粒子（NPs）催化芳基卤化物和炔基羧酸的脱羧偶联（DC）用于合成二芳基炔烃。在相同的催化条件下，按照多米诺脱羧偶联-环化（DCC）方法，还从2-碘苯胺/氨基苯并环庚烯溴化物​​和炔基羧酸合成了吲哚和3-吡咯啉杂环。Pd @ PS的结合锚固和催化性能使该方法有利于产物的形成。
• Pd-Catalyzed decarboxylative alkynylation of alkynyl carboxylic acids with arylsulfonyl hydrazides<i>via</i>a desulfinative process
  作者：Sheng Chang、Ying Liu、Shu Zhu Yin、Lin Lin Dong、Jian Feng Wang

  DOI：10.1039/c8nj02964d

  日期：——

  In the presence of a Pd(II)/P-ligand catalytic system, decarboxylative alkynylation of alkynyl carboxylic acids and arylsulfonyl hydrazides by desulfinative coupling could provide aryl alkynes in satisfactory yields by either judiciously selecting palladium catalysts or modulating phosphine ligands under mild conditions. The reported coupling reactions are very practical as they do not require the

  在Pd（II）/ P-配体催化体系的存在下，通过明智地选择钯催化剂或在温和条件下调节膦配体，通过脱硫偶联将炔基羧酸和芳基磺酰肼进行脱羧烷基化可以提供令人满意的收率的芳基炔烃。报道的偶联反应非常实用，因为它们不需要保护惰性气体或氧气，并且可以耐受许多官能团。
• Highly effective copper-catalyzed decarboxylative coupling of aryl halides with alkynyl carboxylic acids
  作者：Xiaoming Qu、Tingyi Li、Peng Sun、Yan Zhu、Hailong Yang、Jincheng Mao

  DOI：10.1039/c1ob05969f

  日期：——

  We have developed a highly effective copper-catalyzed decarboxylative coupling of alkynylcarboxylic acids with various aryl and alkyl halides at 2 mol% loading of copper. This method is simple, economical and practical for the synthesis of disubstituted alkyne compounds.

  我们已经开发了在铜的2摩尔％负载下，炔基羧酸与各种芳基和烷基卤化物的高效铜催化脱羧偶联反应。该方法对于合成二取代炔烃化合物是简单，经济和实用的。
• Rhodium/Copper Cocatalyzed Highly <i>trans</i>-Selective 1,2-Diheteroarylation of Alkynes with Azoles via C–H Addition/Oxidative Cross-Coupling: A Combined Experimental and Theoretical Study
  作者：Guangying Tan、Lei Zhu、Xingrong Liao、Yu Lan、Jingsong You

  DOI：10.1021/jacs.7b07242

  日期：2017.11.8

  experimental and theoretical methods, the reaction mechanism for addition/oxidative cross-coupling of internal alkynes with azoles has been investigated. Theoretical calculations reveal that the metalation/deprotonation of azole could occur with either rhodium or copper species. When azolylrhodium is formed, an alkyne could insert into the Rh–C bond. Another azolyl group could then transfer to rhodium from azolylcopper

  用芳基化试剂过渡金属催化的二芳基炔烃的加成反应以合成四芳基乙烯通常遇到严格的反应条件，并且依赖于使用预官能化的底物，例如有机卤化物或替代物以及有机金属试剂。在这项工作中，我们建立了高度跨性别的铑/铜共催化的C–H加成/氧化偶联过程使炔烃与唑类化合物进行1,2-选择性1,2-二杂芳基化反应。此外，本文开发的二杂芳基化反应可为杂芳烃掺杂的四芳基乙烯的合成打开一扇门，THF-水混合物和固体粉末中的光致发光（PL）光谱验证了这些四（杂）芳基乙烯是聚集诱导发射（AIE）活跃，建立一个新的AIE分子库。结合实验和理论方法，研究了内部炔烃与吡咯的加成/氧化交叉偶联的反应机理。理论计算表明，无论是铑还是铜，都可能发生吡咯的金属化/去质子化。当形成偶氮基铑时，炔可以插入Rh-C键中。然后另一个偶氮基可以从偶氮铜化合物转移到铑上。随后的分子内反亲核加成产生第二个C–C键。同时，理论计算也解释了形成氢杂芳基化副产物的假定途径。
• Copper-catalyzed C(sp²)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons
  作者：Wei Xu、Bo Yu、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1002/aoc.3298

  日期：2015.6

  Copper‐catalyzed Sonogashira‐type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5 mol% < Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. Both aromatic and aliphatic terminal alkynes as well as diverse aryl iodides were employed in this transformation

  通过引入催化量的多环芳烃添加剂，铜催化的Sonogashira型反应得以显着加速。这种新颖的催化系统具有低铜负载量（0.5 mol％