1-氟-4-[4-(4-氟苯基)丁-1,3-二炔基]苯 | 55606-94-5

• 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: 1-氟-4-[4-(4-氟苯基)丁-1,3-二炔基]苯
• 英文名称: 1,4-bis(4'-fluorophenyl)-buta-1,3-diyne
• 英文别名: 1,4-bis(4-fluorophenyl)-1,3-butadiyne；1,4-bis(p-fluorophenyl)buta-1,3-diyne；1,4-bis(p-fluorophenyl)-1,3-butadiyne；Benzene, 1,1'-(1,3-butadiyne-1,4-diyl)bis[4-fluoro-；1-fluoro-4-[4-(4-fluorophenyl)buta-1,3-diynyl]benzene
• CAS: 55606-94-5
• 化学式: C₁₆H₈F₂
• 分子量: 238.236
• InChiKey: RUDSKSLJCZGANW-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C
• 沸点：
  330.4±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  3
• 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：
  2

反应信息

• 作为反应物：
  描述：

  1-氟-4-[4-(4-氟苯基)丁-1,3-二炔基]苯 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以58%的产率得到1,2,3-tribromo-6-fluoro-4-(4-fluorophenyl)naphthalene
  参考文献：
  名称：

  Bromine-mediated cyclization of 1,4-diaryl buta-1,3-diyne to 1,2,3-tribromo-4-aryl naphthalene

  摘要：

  Bromine-mediated intramolecular cyclization of 1,4-diaryl buta-1,3-diynes has been developed for the construction of naphthalene motifs. A number of 1,2,3-tribromo-4-aryl naphthalenes are synthesized under mild reaction condition by the 6-endo-dig electrophilic cyclization of the corresponding 1,4-diaryl buta-1,3-diynes by Br-2 in moderate to excellent yields. This methodology has been successfully extended to the synthesis of 1,2,3,4-tetraphenyl naphthalene derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.079
• 作为产物：
  描述：

  1-(2,2-二溴乙烯基)-4-氟苯 在 copper(l) iodide 、 1,8-diazabicyclo[5.4.0]undec-7-ene monohydrate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以89%的产率得到1-氟-4-[4-(4-氟苯基)丁-1,3-二炔基]苯
  参考文献：
  名称：

  Cu-Catalyzed solvent-free, pot-economic synthesis of 1,3-dynes from 1,1-dibromoalkenes in the presence of DBU•H2O

  摘要：

  DOI：

  10.24820/ark.5550190.p011.466

文献信息

• A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes
  作者：Jiawang Liu、Carolin Schneider、Ji Yang、Zhihong Wei、Haijun Jiao、Robert Franke、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.202010768

  日期：2021.1.4

  3‐diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synthetically useful α‐alkynyl‐α, β‐unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs. Control experiments and density‐functional

  描述了（不）对称 1,3-二炔的化学选择性、区域选择性和立体选择性单氢酰胺化。这种新型转化成功的关键是采用具有特定配体 Neolephos 的先进钯催化剂系统。这种合成有用的 α-炔基-α, β-不饱和酰胺的通用方法的合成价值通过几种结构复杂的分子和上市药物的多样化得到了展示。控制实验和密度泛函理论 (M06L-SMD) 计算也表明底物在控制不对称 1,3-二炔的区域选择性中发挥着关键作用。
• Copper-Mediated Deacylative Coupling of Ynones via C–C Bond Activation under Mild Conditions
  作者：Lili Feng、Tingjun Hu、Saisai Zhang、Heng-Ying Xiong、Guangwu Zhang

  DOI：10.1021/acs.orglett.9b03684

  日期：2019.12.6

  The intermolecular deacylative coupling of unstrained ynones via C-C bond activation was accomplished by a CuCl-bpy system under mild reaction conditions. This protocol features facile cleavage of the C-C bond at room temperature, broad substrate scope, and efficient construction of important symmetric and unsymmetrical 1,3-diyne adducts through homo or cross coupling of ynones, respectively. The preliminary

  通过温和的反应条件下的CuCl-bpy系统完成了未应变的炔酮通过CC键活化的分子间脱酰基反应。该协议的特点是在室温下容易裂解CC键，广泛的底物范围，以及通过炔酮的均相或交联分别有效构建重要的对称和不对称1,3-二炔加合物的方法。初步的机械研究表明，此过程可能涉及酰基铜（III）配合物。
• Synthesis of 2,3,6-trisubstituted pyridines by transition-metal free cyclization of 1,3-diynes with amino acids
  作者：Gang Zhou、Xiaoming Zhao、Wenyan Dan

  DOI：10.1016/j.tetlet.2017.06.080

  日期：2017.8

  Amino acids are firstly employed in transition-metal free heterocyclization reaction of 1,3-diynes in the presence of K3PO4 and DMSO at 120 °C. This method produces 2,3,6-trisubstituted pyridines with up to 86% yield. The –CO2H group on the amino acids is crucial for this heterocyclization reaction. The mechanism of such a heterocyclization reaction is discussed, as well.

  首先在120°C下在K 3 PO 4和DMSO存在下，将氨基酸用于1,3-二炔的无过渡金属的杂环反应中。该方法产生2,3,6-三取代的吡啶，产率高达86％。氨基酸上的–CO 2 H基团对于该杂环化反应至关重要。还讨论了这种杂环化反应的机理。
• Copper-Catalyzed Aerobic Oxidative Transformation of Ketone-Derived<i>N</i>-Tosyl Hydrazones: An Entry to Alkynes
  作者：Xianwei Li、Xiaohang Liu、Huoji Chen、Wanqing Wu、Chaorong Qi、Huanfeng Jiang

  DOI：10.1002/anie.201405058

  日期：2014.12.22

  A novel strategy involving Cu‐catalyzed oxidative transformation of ketone‐derived hydrazone moiety to various synthetic valuable internal alkynes and diynes has been developed. This method features inexpensive metal catalyst, green oxidant, good functional group tolerance, high regioselectivity and readily available starting materials. Oxidative deprotonation reactions were carried out to form internal

  已开发出一种新的策略，涉及铜催化的酮衍生部分转化为各种合成的有价值的内部炔烃和二炔。该方法的特点是廉价的金属催化剂，绿色氧化剂，良好的官能团耐受性，高区域选择性和易于获得的原料。进行氧化去质子反应以形成内部炔烃和对称二炔。进行hydr与卤化物和末端炔的交叉偶联反应，得到官能化的炔和不对称的共轭二炔。提出了通过碳卡宾中间体进行CC三键形成的机理。
• Tailored Palladium Catalysts for Selective Synthesis of Conjugated Enynes by Monocarbonylation of 1,3‐Diynes
  作者：Jiawang Liu、Ji Yang、Carolin Schneider、Robert Franke、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.201915386

  日期：2020.6.2

  1'-binaphthalene (Neolephos), which permits the palladium-catalyzed selective carbonylation under mild conditions, providing a general preparation of functionalized 1,3-enynes in good-to-high yields with excellent chemoselectivities. Synthetic applications that showcase the possibilities of this novel methodology include an efficient one-pot synthesis of 4-aryl-4H-pyrans as well as the rapid construction of various

  首次实现了容易获得的 1,3-二炔的单烷氧基羰基化以产生合成有用的共轭烯炔。成功的关键是设计和利用新配体 2,2'-双(叔丁基(吡啶-2-基)膦基)-1,1'-联萘 (Neolephos)，它允许钯催化选择性羰基化在温和条件下，以良好到高的产率提供官能化 1,3-烯炔的通用制备，并具有优异的化学选择性。展示这种新方法可能性的合成应用包括 4-芳基-4H-吡喃的高效一锅法合成以及各种杂环、双环和多环化合物的快速构建。