8-(thiophen-2-yl)quinoline | 56421-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(thiophen-2-yl)quinoline
• 英文别名: 8-Thiophen-2-ylquinoline
• CAS: 56421-71-7
• 化学式: C₁₃H₉NS
• 分子量: 211.287
• InChiKey: UVDZTHGZCRJTIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-(thiophen-2-yl)quinoline 、 di(hydrido(1,2-bis(diisopropylphosphino)ethane)platinum(I)) 以 苯 为溶剂， 以70%的产率得到Pt(dippe)(C9H6NC(S)CHCHCH)
  参考文献：
  名称：

  C−H and C−S Activations of Quinoline-Functionalized Thiophenes by Platinum Complexes

  摘要：

  We synthesized and characterized two ligands, 2-(quinolin-8-yl)thiophene (1a) and 3-(quinolin-8-yl)thiophene (1b). The selective C-H activation of the thiophene moieties was achieved by reacting 1a or, 1b and [Pt(CH3)(2)(SMe2)](2). We observed eta(2)-thiophene intermediates during the course of the reactions. The selective C-S bond activation of the thiophene moieties was observed after reacting 1a or 1b and [Pt(dippe)H](2). DFT calculations were performed to elucidate the regioselectivity of C-S activations.

  DOI：

  10.1021/om101171s
• 作为产物：
  描述：

  8-羟基喹啉 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium phosphate 、 三乙胺 、 三环己基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 47.0h， 生成 8-(thiophen-2-yl)quinoline
  参考文献：
  名称：

  Ni(COD)₂/PCy₃ Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature

  摘要：

  Reaction conditions for the Ni(COD)(2)/PCy3 catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)(2)/PCy3 was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature. This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives. In combination with the recently developed Ni-catalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible.

  DOI：

  10.1021/jo202037x

文献信息

• Reductive electrophilic C–H alkylation of quinolines by a reusable iridium nanocatalyst
  作者：Rong Xie、Wenhui Mao、Huanhuan Jia、Jialu Sun、Guangpeng Lu、Huanfeng Jiang、Min Zhang

  DOI：10.1039/d1sc02967c

  日期：——

  electrophilic mono and dialkylations of quinolines with various 2- or 4-functionalized aryl carbonyls or benzyl alcohols by utilizing renewable formic acid as the reductant. This catalytic transformation offers a practical platform for direct access to a vast range of alkyl THQs, proceeding with excellent step and atom-efficiency, good substrate scope and functional group tolerance, a reusable catalyst and abundantly

  在不饱和系统的还原中加入偶联步骤为功能分子的多样化合成提供了一种理想的方法，但由于难以控制化学选择性，迄今为止仍然是一个挑战。在此，通过开发由 Ir 物种（Ir δ +）和 N 掺杂的 SiO 2 /TiO 2载体（Ir/N-SiO 2 /TiO 2)，我们描述了其通过利用可再生甲酸作为还原剂，在喹啉与各种 2-或 4-官能化芳基羰基或苯甲醇的还原亲电单和二烷基化反应中的应用。这种催化转化为直接获得各种烷基 THQ 提供了一个实用的平台，具有出色的步骤和原子效率、良好的底物范围和官能团耐受性、可重复使用的催化剂和大量可用的原料，以及水和二氧化碳的生成作为副产品。这项工作为在多相还原催化下进一步开发更有用的有机转化打开了一扇门。
• Synthesis of 8-heteroaryl nitroxoline analogues via one-pot sequential Pd-catalyzed coupling reactions
  作者：Helena Brodnik、Franc Požgan、Bogdan Štefane

  DOI：10.1039/c5ob02364e

  日期：——

  A series of 8-heteroaryl substituted quinolines were prepared, either by direct C–H arylation of five-membered heteroarenes, or Pd-catalyzed coupling of organoboron reagents with bromoquinolines. The use of (benzo)thiophenyl or (benzo)furanyl boron coupling partners allowed further C–H functionalization on the five-membered heteroaryl ring with aryl bromides in one flask to access a variety of polyconjugated

  通过五元杂芳烃的直接C–H芳基化，或Pd催化的有机硼试剂与溴喹啉的偶联，制备了一系列8-杂芳基取代的喹啉。通过使用（苯并）硫代苯基或（苯并）呋喃基硼偶联剂，可以在一个烧瓶中用芳基溴化物进一步在五元杂芳基环上进行C–H官能化，从而获得各种多共轭分子结构。所开发的方法代表了一种简单的方法，可用于生物学上有趣的硝基氧杂环丁烷核心的8芳基类似物。
• Carbon–Sulfur Bond Cleavage Reactions of Quinolyl-Substituted Thiophenes with Iron Carbonyls
  作者：Takumi Matsunaga、Isamu Kinoshita、Masakazu Hirotsu

  DOI：10.1021/acs.organomet.7b00280

  日期：2017.6.12

  reactivity of the thiolate complexes [Fe2(μ-LR)(CO)5] and [Fe3(μ-LR)(CO)8]. Although the photoreactions of the diiron complexes [Fe2(μ-LR)(CO)5] with [Fe(CO)5] produced the corresponding triiron complexes [Fe3(μ-LR)(CO)8], desulfurization leading to the formation of [Fe2CHCHCHC(Q)}(CO)5] was predominant for R = H, and a fast conversion of the triiron complex to a CO elimination product was observed for R =

  喹啉基取代的噻吩（2-（8'-喹啉基）噻吩（QT），2-甲基-5-（8'-喹啉基）噻吩（MeQT），2-（8'-喹啉基）-5-（三甲基硅烷基）噻吩（TMSQT）），与的[Fe 3（CO）12 ]，得到相应的硫醇盐，桥接二铁配合物的[Fe 2（μ-L - [R ）（CO）5 ]（R = H，Me中，森达3），其中L H，L Me和L TMS是通过QT中C–S键的氧化加成形成的阴离子N，C，S-三齿配体（SC（R）CHCHC（Q）2–，Q = 8-喹啉基） ，MeQT和TMSQT。相反，喹啉基取代的噻吩与[Fe（CO）的光反应产物的形成5 ]取决于噻吩环的R基团。QT的光反应，得到无硫二铁配合物的[Fe 2 CHCHCHC（Q）}（CO）5 ]，而MeQT和TMSQT的光反应，得到硫醇盐桥联三铁配合物的[Fe 3（μ-L我）（ CO）8 ]和二铁配合物的[Fe 2（μ-L TMS）（CO）5
• The Influence of the Quinoline Moiety on Direct Pd‐Catalyzed Arylation of Five‐Membered Heterocycles
  作者：Bogdan Štefane、Uroš Grošelj、Jurij Svete、Franc Požgan、Drago Kočar、Helena Brodnik Žugelj

  DOI：10.1002/ejoc.201800842

  日期：2019.1.23

  reactivity of C2‐quinoline‐substituted furan, thiophene and pyrrole derivatives in palladium‐catalyzed direct C–H arylation. The regioselectivity of the reaction was strongly influenced by site position of the attached five‐membered heterocycle thus giving rise to C3‐ and/or C5‐arylated products. Furthermore, the Hammett correlation performed on 5‐substituted‐8‐(furan‐2‐yl)quinolines indicates that a marginally

  本文中我们报道了在钯催化的直接CHH芳基化反应中，C2-喹啉取代的呋喃，噻吩和吡咯衍生物的反应性。反应的区域选择性受到连接的五元杂环的位置的强烈影响，因此产生了C3和/或C5芳基化产物。此外，对5-取代-8-（呋喃-2-基）喹啉进行的哈米特相关性表明，在决定速率的过渡态中会形成少量的正电荷，从而指向亲电子的金属化-去质子化反应机理。
• [EN] HYDROXAMIC AND CARBOXYLIC ACID DERIVATIVES HAVING MMP AND TNF INHIBITORY ACTIVITY<br/>[FR] DERIVES DE L'ACIDE HYDROXAMIQUE ET DE L'ACIDE CARBOXYLIQUE DOTES D'UNE ACTIVITE INHIBITRICE VIS A VIS DES MMP ET DU TNF
  申请人：DARWIN DISCOVERY LIMITED

  公开号：WO1998005635A1

  公开（公告）日：1998-02-12

  (EN) The invention concerns hydroxamic acid and carboxylic acid derivatives of formulae (I): B-X-(CH2)n-CHR1-(CH2)m-CONHOH and (Ia): B-S(O)1-2-(CH2)n-CHR1-(CH2)m-COOR2, in which X is O, NR3 or S(O)0-2, and the other variables have the definitions given in the claims, having MMP and TNF inhibitory activity.(FR) La présente invention se rapporte à des dérivés de l'acide hydroxamique et de l'acide carboxylique, dotés d'une activité inhibitrice vis à vis des métalloprotéases matricielles (MMP) et du facteur de nécrose des tumeurs (TNF). Ces dérivés sont représentés par les formules (I): B-X-(CH2)n-CHR1-(CH2)m-CONHOH et (Ia): B-S(O)1-2-(CH2)n-CHR1-(CH2)m-COOR2, dans lesquelles X est O, NR3 ou S(O)0-2, les autres variables étant définies dans les revendications.

  该发明涉及式(I)和式(Ia)的羟胺酸和羧酸衍生物，具有MMP和TNF抑制活性，其中X为O、NR3或S(O)0-2，其他变量在权利要求中给出了定义。式(I)为B-X-(CH2)n-CHR1-(CH2)m-CONHOH，式(Ia)为B-S(O)1-2-(CH2)n-CHR1-(CH2)m-COOR2。