2-[(E)-2-phenylvinyl]-1-benzothiophene | 28684-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-[(E)-2-phenylvinyl]-1-benzothiophene
• 英文别名: (E)-2-styrylbenzo[b]thiophene；2-styrylbenzo[b]thiophene；trans-Phenyl-2-benzothienylethylen；trans-2-Styrylbenzothiophen；trans-2-Styrylbenzo[b]thiophen；2-[(E)-2-phenylethenyl]-1-benzothiophene
• CAS: 28684-74-4
• 化学式: C₁₆H₁₂S
• 分子量: 236.337
• InChiKey: WUYSFSWCVBMUDG-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-phenylvinyl]-1-benzothiophene 以51%的产率得到
  参考文献：
  名称：

  TOMINAGA, YOSHINORI;LEE, M. L.;CASTLE, R. N., J. HETEROCYCL. CHEM., 1981, 18, N 5, 967-972

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯-1-丙炔 在 溴乙烷 、 magnesium 、 potassium iodide 、 palladium(II) iodide 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 7.0h， 生成 2-[(E)-2-phenylvinyl]-1-benzothiophene
  参考文献：
  名称：

  Synthesis of Benzothiophene Derivatives by Pd-Catalyzed or Radical-Promoted Heterocyclodehydration of 1-(2-Mercaptophenyl)-2-yn-1-ols

  摘要：

  Novel and convenient approaches to benzothiophene derivatives 3 and 5 have been developed, based on heterocyclization reactions of 1-(2-mercaptophenyl)-2-yn-1-is 2 or 4, respectively, readily available from alkynylation of 2-mercaptobenzaldehydes or 1-(2-mercaptophenyl) ketones 1. In particular, 1-(2-mercaptophenyl)-2-yn-1-ols 2, bearing a CH2R substituent on the triple bond (R = alkyl, aryl), were conveniently converted in fair to good yields (55-82%) into (E)-2-(1-alkenyl)benzothiophenes 3 when allowed to react in the presence of catalytic amounts (2 mol %) of PdI2 in conjunction with KI (KI:PdI2 molar ratio = 10) at 80-100 degrees C in MeCN as the solvent, through a heterocyclodehydration process. On the other hand, 2-alkoxymethylbenzothiophenes 5 were selectively obtained in fair to excellent yields (49-98%) via a radical-promoted substitutive heterocyclodehydration process, by reacting 1-(2-mercaptophenyl)-2-yn-1-ols 4 (bearing an alkyl or aryl substituent on the triple bond) in alcoholic media at 80-100 degrees C in the presence of a radical initiator, such as AIBN.

  DOI：

  10.1021/jo201471k

文献信息

• Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis
  作者：Min-Jie Zhou、Lei Zhang、Guixia Liu、Chen Xu、Zheng Huang

  DOI：10.1021/jacs.1c05479

  日期：2021.10.13

  cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system’s exceptional site selectivity and functional group

  脂肪族催化脱氢 (CDA) 在有机合成中的价值在很大程度上仍未得到充分探索。已知的均相 CDA 系统通常需要使用牺牲氢受体（或氧化剂）、贵金属催化剂和苛刻的反应条件，因此将大多数现有方法限制为非或低官能化烷烃的脱氢。在这里，我们描述了一种可见光驱动的双催化剂系统，该系统由廉价的有机光氧化还原和贱金属催化剂组成，用于室温、无受体 CDA (Al-CDA)。该过程由光激发的 2-氯蒽醌引发，涉及脂肪族的 H 原子转移 (HAT) 形成烷基自由基，然后与钴肟反应生成烯烃和 H 2. 这种操作简单的方法能够将容易获得的化学原料直接脱氢成多种官能化的烯烃。例如，我们首次证明了硫醚和酰胺在无氧化剂条件下分别脱饱和为烯基硫醚和烯酰胺。此外，14 种生物相关分子和药物成分的后期脱氢和合成说明了该系统卓越的位点选择性和官能团耐受性。机理研究揭示了双重 HAT 过程，并提供了对反应性和位点选择性起源的见解。
• p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocycles
  作者：Maud Jacubert、Olivier Provot、Jean-François Peyrat、Abdallah Hamze、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1016/j.tet.2010.03.055

  日期：2010.5

  Regioselective hydration of a wide range of internal alkynes has been afforded in high to good yields by using PTSA in EtOH. The scope of the reaction of alkynes has been delineated. Arylaliphatic alkynes and diarylalkynes were regioselectively hydrated in good to excellent yields and short reaction times when the reaction was achieved under microwave irradiation. Moreover, diarylalkynes, arylenynes

  通过在EtOH中使用PTSA，可以实现高产率到良好产率的多种内部炔烃的区域选择性水合。已经描述了炔烃的反应范围。当在微波辐射下完成反应时，芳基脂族炔烃和二芳基炔烃以良好至优异的产率和短的反应时间进行区域选择性水合。而且，对在邻位带有甲氧基或硫代甲基取代基的二芳基炔，芳炔和二芳基二炔进行区域选择性5-内酯化。-dig-环化得到各种2-芳基-和2-苯乙烯基苯并呋喃或苯并噻吩衍生物。我们相信，这种新的无金属污染的环保方法与微波辐射相结合，对于绿色实验室规模的合成研究将非常重要。
• Direct <i>trans</i>-Selective Ruthenium-Catalyzed Reduction of Alkynes in Two-Chamber Reactors and Continuous Flow
  作者：Karoline T. Neumann、Sebastian Klimczyk、Mia N. Burhardt、Benny Bang-Andersen、Troels Skrydstrup、Anders T. Lindhardt

  DOI：10.1021/acscatal.6b01045

  日期：2016.7.1

  efficient trans-selective hydrogenation of alkynes under low hydrogen pressure and low reaction temperatures is reported, applying a commercially available ruthenium hydride complex. The developed reaction conditions, which tolerate a variety of functional groups, are carried out in a two-chamber setup with ex situ generated hydrogen. The reaction setup is highly suitable for deuterium labeling. The trans-selective

  据报道，使用可商购的氢化钌配合物，在低氢压力和低反应温度下有效的炔烃的反式选择性氢化。可以耐受各种官能团的发达反应条件是在两室设置下利用异位产生的氢气进行的。反应设置非常适合氘标记。的反式-选择性氢化外推至一个转移氢化协议，采用连续流动仅为10分钟的保留时间的填充床固定化钌氢化催化剂。
• Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic CS Coupling
  作者：Christopher S. Bryan、Julia A. Braunger、Mark Lautens

  DOI：10.1002/anie.200902843

  日期：2009.9.7

  construction of a CS and a CC bond under catalytic conditions forms the basis of an efficient route to diversely functionalized benzothiophenes from gem‐dihalovinyl thiophenols. The CC bond can be formed in this tandem catalytic process with an organoboron reagent as shown in the scheme (R1=H, Me, F, Cl, Br, OCH2O; R2=H, Me; R3=aryl, heteroaryl, alkenyl, alkyl), or by Heck or Sonogashira coupling with an

  同时施工一个C  S和一个C 催化条件下C键形成从不同地官能化的苯并噻吩的高效路由的基础宝石-dihalovinyl苯硫酚。与c 可以在此串联与有机硼试剂催化工艺来形成C键为显示在方案（R 1 = H中，Me，F，氯，溴， OCH 2 ö  ; R 2 = H中，Me; R 3＝芳基，杂芳基，烯基，烷基），或通过Heck或Sonogashira与烯烃或炔烃偶联。
• An efficient route to regioselective functionalization of benzo[b]thiophenes via palladium-catalyzed decarboxylative Heck coupling reactions: insights from experiment and computation
  作者：Daoshan Yang、Yuxia Liu、Pengfei Sun、Ning Zhang、Wei Wei、Mingyang Sun、Guang Chen、Siwei Bi、Hua Wang

  DOI：10.1039/c5ob01905b

  日期：——

  This study reports the Pd-catalyzed decarboxylative Heck-type coupling of 3-chlorobenzo[b]thiophene-2-carboxylic acids with styrenes.

  这项研究报道了Pd催化的3-氯苯并[b]噻吩-2-羧酸与苯乙烯的脱羧Heck型偶联反应。