1-(2-phenyl-2,3-dihydro-benzothiazol-2-yl)-ethanone | 23219-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 1-(2-phenyl-2,3-dihydro-benzothiazol-2-yl)-ethanone
• 英文别名: 2-acetyl-2-phenylbenzothiazoline；2-Acetyl-2-phenyl-benzothiazol；1-(2-phenyl-3H-1,3-benzothiazol-2-yl)ethanone
• CAS: 23219-44-5
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: BTGICCATIBKVTN-UHFFFAOYSA-N

物化性质

• 沸点：
  427.5±45.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-phenyl-2,3-dihydro-benzothiazol-2-yl)-ethanone 、 5-benzylidene-1,3-dimethyl-pyrimidine-2,4,6-trione 在 Eosin Y 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以90%的产率得到
  参考文献：
  名称：

  苯并噻唑啉作为自由基转移剂：在光辐照条件下通过自由基生成对烯烃进行加氢烷基化和加氢酰化†

  摘要：

  通过使用苯并噻唑啉衍生物开发了在光辐照条件下的新型自由基转移试剂。这些试剂能够在环境温度下在中性条件下进行烯烃的加氢烷基化和加氢酰化，而无需使用任何有毒的试剂或过量的金属。进行了机理研究以阐明基本过程。

  DOI：

  10.1039/c9cc05336k
• 作为产物：
  描述：

  (2-methyl-2,3-dihydro-benzothiazol-2-yl)-phenyl-methanone 反应 24.0h， 以100%的产率得到1-(2-phenyl-2,3-dihydro-benzothiazol-2-yl)-ethanone
  参考文献：
  名称：

  Synthesis and Study of Isomeric Benzo[1,4]oxazines and Benzothiazolines by NMR Spectroscopy and X-Ray Crystallography

  摘要：

  Reaction of 2-aminophenol and 2-aminothiophenol with 1-phenyl-1,2-propanedione yields a mixture of both possible isomeric benzo[1,4]oxazines and benzothiazolines which were characterized by NMR spectroscopy. In addition, the structures for 3-methyl-2-phenyl-2H-benzo[1,4]-oxazin-2-ol and 1-(2-phenyl-2,3-dihydro-benzothiazol-2-yl)-ethanone were established by X-ray diffraction analysis.

  DOI：

  10.1007/s007060050307

文献信息

• Radical Hydroalkylation and Hydroacylation of Alkenes by the Use of Benzothiazoline under Thermal Conditions
  作者：Tatsuhiro Uchikura、Mitsuhiro Toda、Toshiki Mouri、Tatsuya Fujii、Kaworuko Moriyama、Ignacio Ibáñez、Takahiko Akiyama

  DOI：10.1021/acs.joc.0c01872

  日期：2020.10.2

  The hydroalkylation and hydroacylation of electron-deficient alkenes proceeded smoothly by using benzothiazoline derivatives as radical-transfer reagents under thermal conditions without light irradiation or any additive. Both benzyl and benzoyl moieties were transferred efficiently.

  通过使用苯并噻唑啉衍生物作为自由基转移试剂，在没有光照或没有任何添加剂的热条件下，将电子不足的烯烃的加氢烷基化和加氢酰化反应顺利进行。苄基和苯甲酰基部分均被有效转移。
• Visible-Light Driven, Metal-Free Hydroalkylation of Alkenes Mediated by Electron Donor-Acceptor Complex Using Benzothiazolines
  作者：Tatsuhiro Uchikura、Tatsuya Fujii、Kaworuko Moriyama、Takahiko Akiyama

  DOI：10.1246/bcsj.20210322

  日期：2021.12.15

  A visible-light mediated, catalyst-free hydroalkylation of electron-deficient alkenes was achieved using benzothiazoline as a radical transfer reagent. The photoreaction proceeded under household LEDs. Mechanistic studies elucidated the formation of an electron-donor-acceptor complex between benzothiazoline and electron-deficient alkenes.

  以苯并噻唑啉为自由基转移试剂，在可见光介导下实现了缺电子烯烃的无催化剂加氢烷基化反应。光反应在家用 LED 灯下进行。机理研究阐明了苯并噻唑啉和缺电子烯之间形成的电子供体-受体复合物。
• Visible-Light-Driven Enantioselective Radical Addition to Imines Enabled by the Excitation of a Chiral Phosphoric Acid–Imine Complex
  作者：Tatsuhiro Uchikura、Nanami Kamiyama、Toshiki Mouri、Takahiko Akiyama

  DOI：10.1021/acscatal.2c00993

  日期：2022.5.6

  A visible-light-driven enantioselective radical addition to imines enabled by the direct excitation of a chiral phosphoric acid–imine complex was developed. By using benzothiazolines as the radical precursors, chiral amine products were obtained with high enantioselectivities (up to 98% ee). Mechanistic studies elucidated that the chiral phosphoric acid–imine complex has photoredox activities for oxidizing

  通过手性磷酸-亚胺复合物的直接激发，开发了一种可见光驱动的对亚胺的对映选择性自由基加成。通过使用苯并噻唑啉作为自由基前体，获得了具有高对映选择性（高达 98% ee）的手性胺产物。机理研究表明，手性磷酸-亚胺复合物具有氧化苯并噻唑啉的光氧化还原活性。
• Benzothiazolines as radical transfer reagents: hydroalkylation and hydroacylation of alkenes by radical generation under photoirradiation conditions
  作者：Tatsuhiro Uchikura、Kaworuko Moriyama、Mitsuhiro Toda、Toshiki Mouri、Ignacio Ibáñez、Takahiko Akiyama

  DOI：10.1039/c9cc05336k

  日期：——

  Novel radical transfer reagents under photoirradiation conditions were developed by the use of benzothiazoline derivatives. These reagents enabled both hydroalkylation and hydroacylation of alkenes under neutral conditions at ambient temperature without any toxic reagents or an excess amount of metals. A mechanistic study was carried out to elucidate the radical process.

  通过使用苯并噻唑啉衍生物开发了在光辐照条件下的新型自由基转移试剂。这些试剂能够在环境温度下在中性条件下进行烯烃的加氢烷基化和加氢酰化，而无需使用任何有毒的试剂或过量的金属。进行了机理研究以阐明基本过程。
• Synthesis and Study of Isomeric Benzo[1,4]oxazines and Benzothiazolines by NMR Spectroscopy and X-Ray Crystallography
  作者：Vıctor Santes、Susana Rojas-Lima、Rosa L. Santillan、Norberto Farfán

  DOI：10.1007/s007060050307

  日期：1999.12

  Reaction of 2-aminophenol and 2-aminothiophenol with 1-phenyl-1,2-propanedione yields a mixture of both possible isomeric benzo[1,4]oxazines and benzothiazolines which were characterized by NMR spectroscopy. In addition, the structures for 3-methyl-2-phenyl-2H-benzo[1,4]-oxazin-2-ol and 1-(2-phenyl-2,3-dihydro-benzothiazol-2-yl)-ethanone were established by X-ray diffraction analysis.

表征谱图