5-(p-tolyl)thiophene-2-carbonitrile | 77673-51-9

• 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: 5-(p-tolyl)thiophene-2-carbonitrile
• 英文别名: 5-(4-Methylphenyl)thiophene-2-carbonitrile
• CAS: 77673-51-9
• 化学式: C₁₂H₉NS
• mdl: MFCD01860765
• 分子量: 199.276
• InChiKey: HADKWIALNBHXHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(p-tolyl)thiophene-2-carbonitrile 在 sodium azide 、 氯化铵 、 N,N-二甲基甲酰胺 作用下， 以70%的产率得到5-(5-(p-tolyl)thiophen-2-yl)-1H-tetrazole
  参考文献：
  名称：

  Synthesis and Structural Characterization of Ricin Inhibitors Targeting Ribosome Binding Using Fragment-Based Methods and Structure-Based Design

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c01370
• 作为产物：
  描述：

  2-氰基噻吩 、 对溴甲苯 在 C₄₀H₃₆N₂O₂Pd⁽²⁺⁾*2C₂H₄O₂ 、 potassium carbonate 、 三甲基乙酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以73%的产率得到5-(p-tolyl)thiophene-2-carbonitrile
  参考文献：
  名称：

  无磷的双（烷氧基）钯配合物低催化剂负载下噻吩的直接C–H芳基化

  摘要：

  在双（烷氧基）钯配合物（Cat.I，0.1-0.2 mol％）的低催化剂负载下，已开发出一种有效的无磷的噻吩在α位上无膦直接CH芳基化的化合物。所开发的合成方法可用于从芳基或杂芳基溴化物以良好至优异的产率合成α-芳基/杂芳基噻吩，并且与带有给电子或吸电子基团的底物相容。噻吩2位和5位的反应性是相同的，并且在最佳条件下不依赖于空间位阻。该条件还可以以高转化率应用于其他杂环部分，例如苯并噻吩，苯并呋喃和吡咯。

  DOI：

  10.1021/jo402745b

文献信息

• Direct C–H Arylation of Thiophenes at Low Catalyst Loading of a Phosphine-Free Bis(alkoxo)palladium Complex
  作者：Yabo Li、Jingran Wang、Mengmeng Huang、Zhiwei Wang、Yusheng Wu、Yangjie Wu

  DOI：10.1021/jo402745b

  日期：2014.4.4

  An efficient phosphine-free direct C–H arylation of thiophenes at the α-position has been developed at low catalyst loading of bis(alkoxo)palladium complex (Cat.I, 0.1–0.2 mol %). The developed synthetic method can be applied to the synthesis of α-aryl/heteroaryl thiophenes from aryl or heteroaryl bromides in good to excellent yields and is compatible with the substrates bearing electron-donating or

  在双（烷氧基）钯配合物（Cat.I，0.1-0.2 mol％）的低催化剂负载下，已开发出一种有效的无磷的噻吩在α位上无膦直接CH芳基化的化合物。所开发的合成方法可用于从芳基或杂芳基溴化物以良好至优异的产率合成α-芳基/杂芳基噻吩，并且与带有给电子或吸电子基团的底物相容。噻吩2位和5位的反应性是相同的，并且在最佳条件下不依赖于空间位阻。该条件还可以以高转化率应用于其他杂环部分，例如苯并噻吩，苯并呋喃和吡咯。
• Synthesis of an Air-Stable Pd(0) Catalyst Bearing Donor and Acceptor Phosphine Ligands
  作者：Ryota Sato、Takaki Kanbara、Junpei Kuwabara

  DOI：10.1021/acs.organomet.9b00646

  日期：2020.1.27

  We synthesized a new Pd(0) complex bearing π-acceptor ligands and a σ-donor ligand and confirmed that it exhibits high air stability and catalytic activity in direct arylation reactions. Moreover, stoichiometric reactions of the complex revealed that the σ-donor ligand does not dissociate from the Pd center.

  我们合成了一个新的Pd（0）配合物，带有π-受体配体和σ-供体配体，并证实了它在直接芳基化反应中具有很高的空气稳定性和催化活性。此外，配合物的化学计量反应表明，σ-供体配体不会从Pd中心解离。
• Air-stable Pd(0) catalyst bearing dual phosphine ligands: a detailed evaluation of air stability and catalytic property in cross-coupling reactions
  作者：Ryota Sato、Takaki Kanbara、Junpei Kuwabara

  DOI：10.1039/d0dt02744h

  日期：——

  have synthesised an air-stable Pd(0) catalyst bearing donor and acceptor phosphine ligands (Complex 1). This study revealed the long-term air stability and catalytic property of Complex 1 as a catalyst for cross-coupling reactions, where it was stable in air for eight months. DFT calculations revealed that the acceptor ligands in Complex 1 decreased the HOMO energy level, which provided the observed

  我们已经合成了带有供体和受体膦配体（化合物1）的空气稳定的Pd（0）催化剂。这项研究揭示了络合物1作为交叉偶联反应的催化剂的长期空气稳定性和催化性能，在空气中稳定8个月。DFT计算表明，配合物1中的受体配体降低了HOMO能级，从而提供了观察到的空气稳定性。综合大楼1成功地用作直接C–H芳基化反应和Suzuki–Miyaura交叉偶联反应的催化剂，并催化了相对不活泼的底物2-氯吡啶的反应，这是常规的，空气稳定的Pd（0）无法实现的催化剂。分离偶联反应的中间体表明，每个中间体均具有供体配体（PCy 3），该配体经确定可赋予复合物1所显示的高催化活性。
• [EN] 2,3-DIHYDROBENZOXAZINE AND 2,3-DIHYDROBENZOTHIAZINE DERIVATES AS HIF-INHIBITORS FOR THE TREATMENT OF CANCER AND INFLAMMATORY DISEASES<br/>[FR] DÉRIVÉS DE 2,3-DIHYDROBENZOXAZINE ET DE 2,3-DIHYDROBENZOTHIAZINE UTILISÉS EN TANT QU'INHIBITEURS DES HIF POUR LE TRAITEMENT DU CANCER ET DES MALADIES INFLAMMATOIRES
  申请人：ELARA PHARMACEUTICALS GMBH

  公开号：WO2011057892A1

  公开（公告）日：2011-05-19

  The present invention provides novel 2,3-dihydrobenzazine compounds of the formula (I), the pharmaceutically acceptable salts thereof, the N-oxides thereof and the pharmaceutically acceptable salts of said N-oxides. Formula (I) X is O or S(=O)n with n being 0, 1 or 2; R1 is phenyl or C-bound monocyclic 5- or 6-membered heteroaryl, wherein phenyl and monocyclic 5- or 6-membered heteroaryl are unsubstituted or carry 1, 2 or 3 radicals R1a which are identical or different; R1a is selected from the group consisting of halogen, cyano, NO2, NH2, OH, SH, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, hydroxy-C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, fluorinated C1-C2-alkyl, SF5, fluorinated C1-C2-alkoxy, C(O)R3, NR4R5, N(OR6)R7 and C(O)OR8, or two radicals R1a, which are bound to adjacent carbon atoms, may also form a bridging moiety O-Alk-O, wherein AIk is selected from CH2, CH2CH2, CHF and CF2; R2 is phenyl or C- or N-bound monocyclic 5- or 6-membered heteroaryl, wherein phenyl and monocyclic 5- or 6-membered heteroaryl carry a CN radical and may additionally carry 1, 2 or 3 radicals R2a which are identical or different; R2a is selected from the group consisting of halogen, cyano, NO2, NH2, OH, SH, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, hydroxy-C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, fluorinated C1-C2-alkyl, SF5, fluorinated C1-C2-alkoxy, C(O)R3, NR4R5, N(OR6)R7 and C(O)OR8, or two radicals R2a, which are bound to adjacent carbon atoms, may also form a bridging moiety O-Alk'-O, wherein AIk' is selected from CH2, CH2CH2, CHF and CF2; and where R3 to R8 are as defined in the claims and the specification. The invention relates to use of these compounds in therapy, in particular in the therapy of a disease or disorder selected from the group consisting of inflammatory diseases, a hyperproliferative disease or disorders, a hypoxia related pathology and a disease characterized by pathophysiological hyper-vascularisation.
• Synthesis and Structural Characterization of Ricin Inhibitors Targeting Ribosome Binding Using Fragment-Based Methods and Structure-Based Design
  作者：Xiao-Ping Li、Rajesh K. Harijan、Bin Cao、Jennifer N. Kahn、Michael Pierce、Anastasiia M. Tsymbal、Jacques Y. Roberge、David Augeri、Nilgun E. Tumer

  DOI：10.1021/acs.jmedchem.1c01370

  日期：2021.10.28