3-(benzo[d]thiazol-2-yl)-1-phenylpropan-1-one | 92855-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(benzo[d]thiazol-2-yl)-1-phenylpropan-1-one
• 英文别名: 3-Benzothiazol-2-yl-1-phenyl-propan-1-one；3-(1,3-benzothiazol-2-yl)-1-phenylpropan-1-one
• CAS: 92855-46-4
• 化学式: C₁₆H₁₃NOS
• mdl: MFCD04323203
• 分子量: 267.351
• InChiKey: KJZDZSKCFBHGIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  γ-苯基-γ-丁内酯 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 3-(benzo[d]thiazol-2-yl)-1-phenylpropan-1-one
  参考文献：
  名称：

  Babitschew,F.S., Journal of general chemistry of the USSR, 1963, vol. 33, p. 2942 - 2948

  摘要：

  DOI：

文献信息

• Chemoselective and metal-free reduction of α,β-unsaturated ketones by <i>in situ</i> produced benzeneselenol from <i>O</i>-(<i>tert</i>-butyl) Se-phenyl selenocarbonate
  作者：Andrea Temperini、Marco Ballarotto、Carlo Siciliano

  DOI：10.1039/d0ra07128e

  日期：——

  The carbon–carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. This mild, metal-free and experimentally simple reduction procedure displays considerable functional-group compatibility, products are obtained in good to excellent yields, and the use

  亚芳基丙酮和查耳酮的碳碳双键可以通过O- (叔丁基)硒苯基硒代碳酸酯与盐酸在乙醇中的反应原位产生的苯硒醇选择性还原。这种温和、无金属且实验简单的还原过程显示出相当大的官能团兼容性，产品的收率非常好，并且避免使用有毒的 Se/CO 混合物和 NaSeH，或有气味且对空气敏感的苯硒醇.
• A Photochemical Organocatalytic Strategy for the α‐Alkylation of Ketones by using Radicals
  作者：Davide Spinnato、Bertrand Schweitzer‐Chaput、Giulio Goti、Maksim Ošeka、Paolo Melchiorre

  DOI：10.1002/anie.201915814

  日期：2020.6.8

  Reported herein is a visible‐light‐mediated radical approach to the α‐alkylation of ketones. This method exploits the ability of a nucleophilic organocatalyst to generate radicals upon SN2‐based activation of alkyl halides and blue light irradiation. The resulting open‐shell intermediates are then intercepted by weakly nucleophilic silyl enol ethers, which would be unable to directly attack the alkyl

  本文报道了一种可见光介导的自由基对酮进行α-烷基化的方法。该方法利用了亲核有机催化剂在S N上生成自由基的能力基于2的烷基卤化物的激活和蓝光照射。然后，所得的开壳中间体被弱亲核的甲硅烷基烯醇醚截获，它们将无法通过传统的双电子路径直接攻击卤代烷。温和的反应条件使酮的α位置具有与经典阴离子策略不兼容的官能团。此外，该方法的氧化还原中性性质使其与基于金鸡纳酮的伯胺催化剂兼容，该催化剂被用于开发酮的对映选择性有机催化自由基α-烷基化的罕见实例。
• Metal-Free Direct C-H β-Carbonyl Alkylation of Heteroarenes with Cyclopropanols Mediated by K₂ S₂ O₈
  作者：Qiang Liu、Qiang Wang、Guanqun Xie、Zeyang Fang、Shujiang Ding、Xiaoxia Wang

  DOI：10.1002/ejoc.202000289

  日期：2020.5.10

  direct C–H β‐carbonyl alkylation of heteroarenes has been achieved through K2S2O8‐mediated ring‐opening of cyclopropanols. A wide scope of substrates, such as various substituted quinolines and isoquinolines, pyridines, pyridazine, benzo[d]thiazole, and phenanthroline, underwent the β‐carbonyl alkylation efficiently and afforded the β‐heteroarylated ketones in moderate to excellent yields.

  无金属直接C-H β羰基杂芳烃烷基化已到K达到2小号2 ö 8介导的cyclopropanols的开环。各种各样的底物，例如各种取代的喹啉和异喹啉，吡啶，哒嗪，苯并[d]噻唑和菲咯啉，有效地进行了β羰基烷基化反应，并以中等至优异的产率提供了β杂芳基化的酮。
• Eco-Friendly Syntheses of 2-Substituted Benzoxazoles and 2-Substituted Benzothiazoles from 2-Aminophenols, 2-Aminothiophenols and DMF Derivatives in the Presence of Imidazolium Chloride
  作者：Qingqiang Tian、Wen Luo、Zongjie Gan、Dan Li、Zeshu Dai、Huajun Wang、Xuetong Wang、Jianyong Yuan

  DOI：10.3390/molecules24010174

  日期：——

  A simple, economical and metal-free approach to the synthesis of 2-substituted benzoxazoles and 2-substituted benzothiazoles from 2-aminophenols, 2-aminothiophenols and DMF derivatives, only using imidazolium chloride (50% mmol) as promoter without any other additive, was reported. Various 2-substituted benzoxazoles and 2-substituted benzothiazoles were thus prepared in moderate to excellent yields

  从 2-氨基苯酚、2-氨基苯硫酚和 DMF 衍生物合成 2-取代苯并恶唑和 2-取代苯并噻唑的一种简单、经济且无金属的方法，仅使用氯化咪唑 (50% mmol) 作为促进剂，无需任何其他添加剂，已经报道。各种2-取代的苯并恶唑和2-取代的苯并噻唑因此以中等至极好的产率制备。
• Efficient CDI/CH3SO3H -Catalyzed, Microwave-Assisted Synthesis of 2-Substituted Benzothiazoles
  作者：Yao-Wei Li、Pei-Ming Zhang、Rui Li、Yan Bai、Yu Yu、Zong-Jie Gan

  DOI：10.2174/1570178615666180611120239

  日期：2018.12.4

  synthesized in good yield and their structures were characterized by 1H-NMR, 13CNMR, IR and mass spectrometry. This simple, rapid synthetic method is believed to provide a useful process for the synthesis of 2-substituted benzothiazole compounds.

  发现CDI与CH3SO3H结合在MW条件下对2-氨基硫酚衍生物与羧酸的环化反应非常有效。以高收率合成了十四种苯并噻唑衍生物，并通过1 H-NMR，13 CNMR，IR和质谱对它们的结构进行了表征。据信这种简单，快速的合成方法为合成2-取代的苯并噻唑化合物提供了有用的方法。