4-acetyl-5-methoxy-2-oxobenz[1,3]oxathiole | 865851-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-acetyl-5-methoxy-2-oxobenz[1,3]oxathiole
• 英文别名: 4-acetyl-5-methoxy-1,3-benzoxathiol-2-one；4-acetyl-5-methoxybenzo[d][1,3]oxathiol-2-one
• CAS: 865851-35-0
• 化学式: C₁₀H₈O₄S
• 分子量: 224.237
• InChiKey: ONUWFFKVCJEBOP-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  380.7±52.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetyl-5-methoxy-2-oxobenz[1,3]oxathiole 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 二溴甲烷 为溶剂， 反应 4.0h， 以64%的产率得到4-acetyl-5-methoxybenzo[d][1,3]oxathiole
  参考文献：
  名称：

  [EN] NOVEL CHALCONE DERIVATIVES WITH CYTOTOXIC ACTIVITY
  [FR] NOUVEAUX DÉRIVÉS DE CHALCONE PRÉSENTANT UNE ACTIVITÉ CYTOTOXIQUE

  摘要：

  公开号：

  WO2011009826A3
• 作为产物：
  描述：

  4-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以73%的产率得到4-acetyl-5-methoxy-2-oxobenz[1,3]oxathiole
  参考文献：
  名称：

  New domino reaction. One pot synthesis of 4,7-dihydroxythioaurone derivatives from benzaldehydes and 4-acetyl-2-oxo-benz[1,3]oxathiole

  摘要：

  A convenient synthesis of 4,7-dihydroxythioaurone derivatives by a one pot reaction of benzaldehydes with 4-acetyl-2-oxobenz[1,3]oxathioles and piperidine acetate in DMSO is described. The structures of the compounds, including double bond geometry were proved unequivocally by NMR methods. The thioaurone ring system seems to be formed by three consecutive reactions: opening of the oxathiolone ring with piperidine, oxidation of the formed mercapto group with DMSO or/and air to disulfide, and condensation with aldehyde. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.107

文献信息

• Acid-catalyzed synthesis of oxathiolone fused chalcones. Comparison of their activity toward various microorganisms and human cancer cells line
  作者：Marek T. Konieczny、Wojciech Konieczny、Michał Sabisz、Andrzej Skladanowski、Roland Wakieć、Ewa Augustynowicz-Kopeć、Zofia Zwolska

  DOI：10.1016/j.ejmech.2006.12.014

  日期：2007.5

  Substituted oxathiolone fused chalcones were prepared by condensation of 4-acetyl-5-methoxy-2-oxo-benz[1,3]oxathiole with benzaldehydes under acidic conditions. The compounds were tested for cytotoxic, antibacterial, antifungal and tuberculostatic activity. Three derivatives demonstrated weak activity against HeLa cells, two were slightly active against Micrococcus luteus and Staphylococcus aureus, and one was active against Mycobacterium tuberculosis H(37)Rv. (c) 2007 Elsevier Masson SAS. All rights reserved.