4-benzylsulfanylcoumarin | 88369-09-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-benzylsulfanylcoumarin
• 英文别名: 4-(benzythio)coumarin；4-S-benzylcoumarin；2H-1-Benzopyran-2-one, 4-[(phenylmethyl)thio]-；4-benzylsulfanylchromen-2-one
• CAS: 88369-09-9
• 化学式: C₁₆H₁₂O₂S
• 分子量: 268.336
• InChiKey: DLNRLPJPCQECDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 在 potassium carbonate 、 三乙胺 、 硫脲 作用下， 以 水 为溶剂， 生成 4-benzylsulfanylcoumarin
  参考文献：
  名称：

  Synthesis of 4-Sulfanylcoumarins Using Thiourea and Alkyl Halides as the Sulfanylation Agent in Polyethylene Glycol-Water

  摘要：

  A novel and efficient route for the synthesis of 4-sulfanylcoumarins is disclosed. The direct sulfanylation of 4-tosyloxycoumarins with thiourea and various alkyl halides in polyethylene glycol 200-water ( PEG 200-H2O), at room temperature under an air atmosphere, affords the corresponding 4-sulfanylcoumarins in moderate to excellent yields. This transformation shows good substrate scope and takes place in a green solvent.

  DOI：

  10.1055/s-0032-1318139

文献信息

• 4-Thio coumarins
  申请人：——

  公开号：US20040002538A1

  公开（公告）日：2004-01-01

  4-thio substituted coumarin derivatives and coumarin dimers are provided, as well as processes for their preparation. A synthetic process for the preparation of 4-thio substituted coumarin derivatives is provided using mild reaction conditions, which maintains a high substituent tolerance and is appropriate for use in solid phase syntheses for producing a library of 4-thio substituted coumarin derivatives for biological screening.

  提供4-硫代取代香豆素衍生物和香豆素二聚体，以及它们的制备方法。提供了一种使用温和反应条件的合成方法，用于制备4-硫代取代香豆素衍生物，该方法具有高取代基耐受性，并适用于固相合成，以生产用于生物筛选的4-硫代取代香豆素衍生物库。
• Direct sulfanylation of 4-hydroxycoumarins with thiols in water
  作者：Yi-Yuan Peng、Yanfang Wen、Xuechun Mao、Guanyinsheng Qiu

  DOI：10.1016/j.tetlet.2009.03.004

  日期：2009.5

  The direct sulfanylation of 4-hydroxycoumarins with thiols via C–OH bond activation in water under mild conditions is described, which afforded the corresponding 4-sulfanylcoumarins in good yields.

  描述了在温和的条件下，通过水中的C-OH键活化，4-羟基香豆素与硫醇的直接磺酰化反应，从而以良好的收率提供了相应的4-硫烷基香豆素。
• Heterocyclic bioantioxidants. 3. Effect of a substituent on the result of the reduction of 3-nitro-4-hetero-substituted coumarins with sodium hydrosulfite
  作者：�. A. Parfenov、L. D. Smirnov

  DOI：10.1007/bf00529367

  日期：1992.3
• Instance of direct replacement of a nitro group attached to an unsaturated center of a coumarin by a mercapto group
  作者：�.. A. Parfenov、L. D. Smirnov

  DOI：10.1007/bf00480879

  日期：1990.8
• Synthesis of 4-Sulfanylcoumarins Using Thiourea and Alkyl Halides as the Sulfanylation Agent in Polyethylene Glycol-Water
  作者：Yiyuan Peng、Zhenlan Yin、Yu Wang、Qin Yang、Ying Wang、Jingshi Xu、Zhihong Deng

  DOI：10.1055/s-0032-1318139

  日期：——

  A novel and efficient route for the synthesis of 4-sulfanylcoumarins is disclosed. The direct sulfanylation of 4-tosyloxycoumarins with thiourea and various alkyl halides in polyethylene glycol 200-water ( PEG 200-H2O), at room temperature under an air atmosphere, affords the corresponding 4-sulfanylcoumarins in moderate to excellent yields. This transformation shows good substrate scope and takes place in a green solvent.