2-methyl-3-benzoylbenzothiophene | 65628-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-3-benzoylbenzothiophene
• 英文别名: 3-benzoyl-2-methylbenzothiophene；(2-methylbenzo[b]thiophen-3-yl)(phenyl)methanone；(2-methyl-benzo[b]thiophen-3-yl)-phenyl ketone；(2-Methyl-benzo[b]thiophen-3-yl)-phenyl-keton；Methanone, (2-methylbenzo[b]thien-3-yl)phenyl-；(2-methyl-1-benzothiophen-3-yl)-phenylmethanone
• CAS: 65628-46-8
• 化学式: C₁₆H₁₂OS
• 分子量: 252.337
• InChiKey: OHCVSTADHKWXBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-methyl-3-benzoylbenzothiophene 生成 苯并[b]萘并[2,3-d]噻吩
  参考文献：
  名称：

  CROISY, A.;MISPELTER, J.;LHOSTE, J. -M.;ZAJDELA, F.;JACQUIGNON, P., J. HETEROCYCL. CHEM., 1984, 21, N 2, 353-359

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-methyl-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)-phenylmethanone 以40%的产率得到
  参考文献：
  名称：

  CROISY, A.;MISPELTER, J.;LHOSTE, J. -M.;ZAJDELA, F.;JACQUIGNON, P., J. HETEROCYCL. CHEM., 1984, 21, N 2, 353-359

  摘要：

  DOI：

文献信息

• Synthesis of carbonylated heteroaromatic compounds via visible-light-driven intramolecular decarboxylative cyclization of o-alkynylated carboxylic acids
  作者：Fei Gao、Jiu-Tao Wang、Lin-Lin Liu、Na Ma、Chao Yang、Yuan Gao、Wujiong Xia

  DOI：10.1039/c7cc04813k

  日期：——

  An efficient strategy for the easy access to carbonylated heteroaromatic compounds has been developed via a visible-light-promoted intramolecular decarboxylative cyclization reaction of o-alkynylated carboxylic acids. This method is characterized by its benign conditions and the tolerance to a wide range of functionalities.

  已经通过可见光促进了邻炔基化羧酸的分子内脱羧环化反应，开发了一种易于获得羰基杂芳族化合物的有效策略。该方法的特点是其良性条件和对多种功能的耐受性。
• Hexafluoro-2-propanol-Promoted Intermolecular Friedel–Crafts Acylation Reaction
  作者：Rakesh H. Vekariya、Jeffrey Aubé

  DOI：10.1021/acs.orglett.6b01460

  日期：2016.8.5

  The intermolecular Friedel–Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.

  分子间的Friedel-Crafts酰化反应在六氟-2-丙醇中进行，可在室温下产生芳基和杂芳基酮，而无需任何其他试剂。
• Thiophene analogues of carcinogenic polycyclic hydrocarbons. Elbs pyrolysis of various aroylmethylbenzo[<i>b</i>]thiophenes
  作者：Alain Croisy、Joël Mispelter、Jean-Marc Lhoste、François Zajdela、Pierre Jacquignon

  DOI：10.1002/jhet.5570210217

  日期：1984.3

  benzophenanthrothiophenes 14–17 through Elbs cyclodehydration of ortho-methylated aroylbenzo[b]thiophenes is described. The occurrence of a rearrangement of the thiophene ring in the course of the cyclization is discussed as well as the influence of the temperature on a concurrent cyclodehydration process. Several of these poly-condensed thiophenes were found carcinogenic in mice.

  描述了通过邻甲基化的芳酰基苯并[ b ]噻吩的Elbs环脱水反应合成苯并萘噻吩9和10以及苯并噻吩噻吩14-17。讨论了环化过程中噻吩环重排的发生以及温度对同时进行的环脱水过程的影响。发现这些缩聚噻吩中的几种在小鼠中具有致癌性。
• Photoinduced Vinylogous Dearomatization
  作者：Xinxin Lv、Ya-Nan Qi、Jiahao Wang、Xiaowei Zhao、Zhiyong Jiang

  DOI：10.1021/acs.orglett.3c00966

  日期：2023.5.5

  The first vinylogous dearomatization is reported. Under a photoinduced platform, various benzothiophenes functionalized by ketones at the 3-position could react with 3-methylenechroman-4-ones efficiently, leading to a variety of valuable products that contain the pharmaceutically significant chromones and 2,3-dihydrobenzo[b]thiophenes concurrently. The transformations were revealed to experience hydrogen-atom

  报道了第一个插烯脱芳构化。在光诱导平台下，在 3 位被酮类功能化的各种苯并噻吩可以与 3-亚甲基色满-4-酮有效反应，从而产生多种具有药学意义的色酮和 2,3-二氢苯并[b]噻吩的有价值的产品同时。揭示了这些转化经历了氢原子转移、脱芳构化、烯烃迁移和自由基交叉偶联。
• Metal‐Free Arylation of Benzothiophenes at C4 by Activation as their Benzothiophene S‐Oxides
  作者：Ranjana Bisht、Mihai V Popescu、Zhen He、Ameer M Ibrahim、Giacomo E M Crisenza、Robert S Paton、David John Procter

  DOI：10.1002/anie.202302418

  日期：——

  key structures in materials and medicines and methods for their selective C−H functionalization are highly prized. Activation of benzothiophenes bearing electron-withdrawing groups at C3 as their S-oxides enables formal C−H/C−H coupling with phenols to access C4 arylated benzothiophenes. Computational studies suggest the intermediacy of a π-complex between the benzothiophene and a phenoxonium cation

  苯并噻吩是材料和药物中的关键结构，其选择性 C−H 官能化方法受到高度重视。 C3 处带有吸电子基团的苯并噻吩作为其S氧化物被激活，使得 C−H/C−H 与苯酚发生正式偶联，得到 C4 芳基化苯并噻吩。计算研究表明，苯并噻吩和苯氧鎓阳离子之间存在 π 配合物的中介作用。