2-(thiophen-2-yl)tetrahydrofuran | 100378-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(thiophen-2-yl)tetrahydrofuran
• 英文别名: a-(2-Thienyl)tetrahydrofuran；2-thiophen-2-yloxolane
• CAS: 100378-42-5
• 化学式: C₈H₁₀OS
• 分子量: 154.233
• InChiKey: SCOYNRVYGDDPQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2'-thienyl)-1,4-butanediol 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以71%的产率得到2-(thiophen-2-yl)tetrahydrofuran
  参考文献：
  名称：

  Catalytic FeCl 3 - or Yb(OTf) 3 -mediated synthesis of substituted tetrahydrofurans and C -aryl glycosides from 1,4-diols

  摘要：

  A facile and mild protocol for the synthesis of substituted tetrahydrofurans, 2-deoxy C-aryl glycoside and C-aryl glycosides is described by use of 20 mol%, FeCl3, or Yb(OTf)(3) as acid catalysts. The benzylic carbocation generated undergoes intramolecular substitution by the oxygen nucleophile to result the tetrahydrofurans and C-aryl glycosides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00179-9

文献信息

• Practical and Highly Selective CH Functionalization of Structurally Diverse Ethers
  作者：Miao Wan、Zhilin Meng、Hongxiang Lou、Lei Liu

  DOI：10.1002/anie.201407083

  日期：2014.12.8

  A trityl ion mediated CH functionalization of ethers with a wide range of nucleophiles at ambient temperature has been developed. The reaction displays high chemoselectivity and good functional group tolerance. The protocol also exhibits excellent regio‐ and diastereoselectivities for the unsymmetric ethers, thus stereoselectively generating highly functionalized disubstituted 2,5‐trans tetrahydrofurans

  在环境温度下，已开发出由三苯甲基离子介导的具有多种亲核试剂的醚的CH功能化。该反应显示出高的化学选择性和良好的官能团耐受性。该协议还对非对称醚表现出出色的区域选择性和非对映选择性，因此立体选择性地生成高度官能化的二取代的2,5-反式四氢呋喃（THF），2,6-反式四氢吡喃（THP），2,6-反式二氢吡喃（DHP），和1,3-反式异色团，并突出了该协议在复杂分子合成中的能力。
• An Unprecedented Coupling Reaction of Arylmagnesium Compounds with Tetrahydrofuran Providing 2-Aryltetrahydrofuran Mediated by an Iodoalkane-EtMgBr System
  作者：Atsushi Inoue、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1055/s-1999-2915

  日期：——

  An extremely facile coupling reaction between arylmagnesium compounds and THF by means of an iodoalkane-EtMgBr system provides 2-aryltetrahydrofurans. One-pot synthesis of 2-thienyltetrahydrofuran is achieved from thiophene and THF using this coupling reaction.

  一种通过碘烷-EtMgBr体系实现的芳基镁化合物与THF之间极其简单的耦合反应，提供了2-芳基四氢呋喃。该耦合反应还实现了从噻吩和THF一锅合成2-噻吩基四氢呋喃。
• Utilizing a needle as a source of iron in synergistic dual photoredox catalytic generation of alkoxy radicals
  作者：Alica Ondrejková、Rickard Lindroth、Göran Hilmersson、Carl-Johan Wallentin

  DOI：10.1039/d2cc03262g

  日期：——

  for a structurally divergent oxidative C(sp3)–H bond functionalization. This protocol employs a photoredox/iron dual catalysis allowing for an unprecedented chemoselective single-step transformation of alcohol derivatives giving access to two valuable sets of products, tetrahydrofurans and γ-bromoketones, under one set of conditions. Addition of iron, by slow corrosion of a needle, provides superior

  描述了可见光介导的烷氧基自由基生成，它允许结构上不同的氧化 C(sp 3 )-H 键官能化。该协议采用光氧化还原/铁双催化，允许在一组条件下对醇衍生物进行前所未有的化学选择性单步转化，从而获得两组有价值的产品四氢呋喃和 γ-溴酮。与各种铁 ( III ) 配合物相比，通过针的缓慢腐蚀添加铁可提供优异的反应效率。
• Ligand‐Free Pd‐Catalyzed Reductive Mizoroki‐Heck Reaction Strategy for the One‐Pot Synthesis of Functionalized Oxygen Heterocycles in Deep Eutectic Solvents
  作者：Giuseppe Dilauro、Luciana Cicco、Paola Vitale、Filippo Maria Perna、Vito Capriati

  DOI：10.1002/ejoc.202200814

  日期：2023.1.17

  Ligandless, telescoped, one-pot reductive Mizoroki-Heck reactions proceed smoothly and regioselectively in eco-friendly eutectic mixtures, and under aerobic conditions to yield 2-(hetero)aryl THF or THP derivatives in up to 95 % yield. Key intermediates have also been targeted in DES en route to pharmacologically relevant molecules.

  无配体、嵌套、一锅法还原 Mizoroki-Heck 反应在生态友好的共晶混合物中顺利进行并具有区域选择性，并在有氧条件下以高达 95% 的产率产生 2-（杂）芳基 THF 或 THP 衍生物。关键中间体也在 DES 中成为药理相关分子的目标。
• Enzymatic encoding methods for efficient synthesis of large libraries
  申请人：Nuevolution A/S

  公开号：EP2341140A1

  公开（公告）日：2011-07-06

  Disclosed is a method for obtaining a bifunctional complex comprising a molecule linked to a single stranded identifier oligonucleotide, wherein a nascent bifunctional complex comprising a chemical reaction site and a priming site for enzymatic addition of a tag is a) reacted at the chemical reaction site with one or more reactants, and b) reacted enzymatically at the priming site with one or more tag(s) identifying the reactant(s).

  本发明公开了一种获得双功能复合物的方法，该复合物由与单链标识寡核苷酸相连的分子组成，其中包含化学反应位点和用于酶加标记的引物位点的新生双功能复合物 a) 在化学反应位点与一种或多种反应物反应，b) 在引物位点与一种或多种标识反应物的标记进行酶反应。