2-(2-thienyl)acetophenone | 893739-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-thienyl)acetophenone
• 英文别名: 1-[2-(2-Thienyl)phenyl]ethanone；1-(2-thiophen-2-ylphenyl)ethanone
• CAS: 893739-40-7
• 化学式: C₁₂H₁₀OS
• 分子量: 202.277
• InChiKey: KWGPNQDWNUMLRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-thienyl)acetophenone 在 sodium hydride 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 15.0h， 生成 4-methyl-4H-indeno<1,2-b>thiophene
  参考文献：
  名称：

  无过渡金属的分子内碳原子芳族取代/Büchner反应：芴和[6,5,7]苯并稠合环的合成

  摘要：

  分子内芳族取代和Büchner反应已被认为是构建多环化合物的有力方法。传统上，这些反应是由Rh II催化剂以α-重氮羰基化合物为底物催化的。本文介绍了无过渡金属的分子内芳族取代/Büchner反应。这些反应使用现成的N-甲苯磺酰hydr作为重氮化合物的前体，并显示出较宽的底物范围。

  DOI：

  10.1002/anie.201409982
• 作为产物：
  描述：

  2-溴噻吩 、 2-乙酰苯基硼酸 在 palladium diacetate 、 tri tert-butylphosphoniumtetrafluoroborate 、 sodium hydroxide 作用下， 以 水 、 正丁醇 为溶剂， 反应 12.25h， 生成 2-(2-thienyl)acetophenone
  参考文献：
  名称：

  N-碘代琥珀酰亚胺和双氧在阳光下通过空气合成 10-菲酚

  摘要：

  使用催化量的N-碘代琥珀酰亚胺 (NIS) 与空气中的O 2结合，进行有氧氧化反应，以在室温下在阳光下有效且可扩展地构建一系列 10-菲酚。机理研究表明，原位产生的H 2 O 2负责将 I 2转化为 IOH，作为后期催化循环的潜在引发剂。

  DOI：

  10.1039/d1gc02185k

文献信息

• General Suzuki Coupling of Heteroaryl Bromides by Using Tri-<i>tert</i>-butylphosphine as a Supporting Ligand
  作者：Yinjun Zou、Guizhou Yue、Jianwei Xu、Jianrong Steve Zhou

  DOI：10.1002/ejoc.201402915

  日期：2014.9

  A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids.

  通过使用 Pd(OAc)2/PtBu3 作为催化剂，实现了主要家族杂芳基溴化物的快速 Suzuki 偶联的一般程序。许多偶联在室温下在正丁醇中几分钟内完成。与之前的研究不同，在各种杂芳基和芳基硼酸的偶联中系统地研究了三种典型的杂芳基溴化物。
• Photoredox catalysis powered by triplet fusion upconversion: arylation of heteroarenes
  作者：Jorge Castellanos-Soriano、Daniel Álvarez-Gutiérrez、M. Consuelo Jiménez、Raúl Pérez-Ruiz

  DOI：10.1007/s43630-022-00203-5

  日期：2022.7

  fusion upconversion (TFU, also named triplet–triplet annihilation upconversion) technology for the functionalization (arylation) of furans and thiophenes has been successfully proven. Activation of aryl halides by TFU leads to generation of aryl radical intermediates; trapping of the latter by the corresponding heteroarenes, which act as nucleophiles, affords the final coupling products. Advantages of this

  在这项工作中，成功证明了三重态融合上转换（ TFU ，也称为三重态-三重态湮没上转换）技术在呋喃和噻吩的官能化（芳基化）方面的可行性。TFU活化芳基卤化物导致芳基自由基中间体的产生；后者被作为亲核试剂的相应杂芳烃捕获，得到最终的偶联产物。这种光氧化还原催化方法的优点包括使用非常温和的条件（可见光，标准条件），使用市售的反应物和低负载的无金属光催化剂，在中等和短的照射时间内不存在任何牺牲剂（添加剂） . 淬灭研究证明了高能延迟荧光参与反应机制，而呋喃和噻吩的这种光氧化还原芳基化的双光子性质已通过对能源功率的依赖性得到证明。最后，连续流动装置令人满意地提供了放大条件。 图形概要
• <i>o</i>-Nitrobenzyl Oxime Ethers Enable Photoinduced Cyclization Reaction to Provide Phenanthridines under Aqueous Conditions
  作者：Hidenori Okamura、Momoka Iida、Yui Kaneyama、Fumi Nagatsugi

  DOI：10.1021/acs.orglett.2c04015

  日期：2023.1.27

  In this paper, we describe a novel N–O photolysis of o-nitrobenzyl oxime ethers that enables the synthesis of phenanthridines via intramolecular cyclization reactions. Without the use of additional photocatalysts or photosensitizers, the process proceeds with an efficiency of ≤96% upon exposure of the sample to near-visible light (405 nm) under aqueous conditions. Through the photoinduced production

  在本文中，我们描述了一种新型的邻硝基苄基肟醚的 N-O 光解，它能够通过分子内环化反应合成菲啶。在不使用额外的光催化剂或光敏剂的情况下，在水性条件下将样品暴露于近可见光 (405 nm) 时，该过程的效率≤96%。通过在 HeLa 细胞中光诱导产生荧光菲啶衍生物，证明了生物条件下反应的进展。这种光诱导环化反应可用作不同的光化学仪器，通过诱导生物活性分子的产生来控制生物过程。
• Synthesis, in vitro, and in vivo (Zebra fish) antitubercular activity of 7,8-dihydroquinolin-5(6H)-ylidenehydrazinecarbothioamides
  作者：Sandeep kumar Marvadi、Vagolu Siva Krishna、Goverdhan Surineni、Rudraraju Srilakshmi Reshma、Balasubramanian Sridhar、Dharmarajan Sriram、Srinivas Kantevari

  DOI：10.1016/j.bioorg.2020.103626

  日期：2020.3

  We, herein, describe the synthesis of a series of novel aryl tethered 7,8-dihydroquinolin-5(6H)-ylidenehydrazinecarbothioamides 4a-v, which showed in vitro and in vivo antimycobacterial activity against Mycobacterium tuberculosis (Mtb) H37Rv. The intermediates dihydro-6H-quinolin-5-ones 3a-v were synthesized from beta-enaminones, reacting with cyclochexane-1,3-dione/5,5-dimethylcyclohexane-1,3-dione and ammonium acetate using a modified Bohlmann-Rahtz reaction conditions. They were further reacted with thiosemicarbazide to give the respective hydrazine carbothioamides 4a-v. All the new analogues 4a-v, were characterized by their NMR and mass spectral data analysis. Among the twenty-two compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC27294), two compounds, 4e and 4j, exhibited the highest inhibition with an MIC of 0.39 mu g/mL. Compounds 4a, 4g, and 4k were found to inhibit Mtb at an MIC of 0.78 mu g/mL. Hydrazinecarbothioamides 4a-k, exhibited enhanced activity than dihydroquinolinones 3a-k. The observed increase in potency provides a clear evidence that hydrazinecarbothioamide is a potential pharmacophore, collectively imparting synergistic effect in enhancing antitubercular activity of the dihydroquinolinone core. The in vivo (Zebra fish) antimycobacterial screening of the in vitro active molecules led to the identification of a hit compound, 4j, with significant activity in the Mtb nutrient starvation model (2.2-fold reduction). Docking studies of 4j showed a hydrogen bond with the P156 residue of the protein.
• <i>N</i>-Iodosuccinimide and dioxygen in an air-enabled synthesis of 10-phenanthrenols under sunlight
  作者：Jia-Dong Guo、Xiu-Long Yang、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1039/d1gc02185k

  日期：——

  Using a catalytic amount of N-iodosuccinimide (NIS) in combination with O2 in air, an aerobic oxidative reaction was carried out to efficiently and scalably construct a series of 10-phenanthrenols under sunlight at room temperature. Mechanistic studies reveal that H2O2 generated in situ was responsible for the conversion of I2 to IOH as a potential initiator for later catalytic cycle.

  使用催化量的N-碘代琥珀酰亚胺 (NIS) 与空气中的O 2结合，进行有氧氧化反应，以在室温下在阳光下有效且可扩展地构建一系列 10-菲酚。机理研究表明，原位产生的H 2 O 2负责将 I 2转化为 IOH，作为后期催化循环的潜在引发剂。