4-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one | 17631-02-6

• 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-hydroxybenzo[1,3]oxathiol-2-one
• 英文别名: 4-acetyl-5-hydroxy-1,3-benzoxathiol-2-one；4-acetyl-5-hydroxybenzo[d][1,3]oxathiol-2-one
• CAS: 17631-02-6
• 化学式: C₉H₆O₄S
• 分子量: 210.21
• InChiKey: UFKYILOCMCAXIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one 在 potassium carbonate 、 二甲基亚砜 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 2-(4'-nitrobenzylidene)-4-methoxy-7-piperidinocarbonyloxy-2,3-dihydro-benzo[b]thiophen-3-one
  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
• 作为产物：
  描述：

  5-acetoxy-benzo[1,3]oxathiol-2-one 在 三氯化铝 作用下， 反应 4.0h， 以8.8 g的产率得到6-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one
  参考文献：
  名称：

  Synthesis of Isomeric, Oxathiolone Fused Chalcones, and Comparison of Their Activity toward Various Microorganisms and Human Cancer Cells Line

  摘要：

  在酸性条件下，通过将适当的乙酰苯并[1,3]氧硫杂环戊-2-酮与苯甲醛缩合，制备了同分异构的氧硫杂环戊酮融合查耳酮。利用 HeLa 细胞对合成的化合物进行了细胞毒性活性筛选，并对黄体微球菌、金黄色葡萄球菌、伤寒沙门氏菌、大肠杆菌、普通变形杆菌进行了抗菌活性筛选，对白色念珠菌进行了抗真菌活性筛选，对结核分枝杆菌 H37Rv 和堪萨斯分枝杆菌菌株进行了抗结核活性筛选。

  DOI：

  10.1248/cpb.55.817

文献信息

• [EN] NOVEL CHALCONE DERIVATIVES WITH CYTOTOXIC ACTIVITY<br/>[FR] NOUVEAUX DÉRIVÉS DE CHALCONE PRÉSENTANT UNE ACTIVITÉ CYTOTOXIQUE
  申请人：ADAMED SP ZOO

  公开号：WO2011009826A3

  公开（公告）日：2011-06-09
• Synthesis of oxathiolone fused chalcones bearing O-aminoalkyl side chain. Comparison of stability of isomeric benzoxathiolones under alkylation reaction conditions
  作者：M KONIECZNY、W KONIECZNY、D PIRSKA、A BULAKOWSKA、M SABISZ、A SKLADANOWSKI、R WAKIEC、E AUGUSTYNOWICZKOPEC、Z ZWOLSKA

  DOI：10.1016/s0385-5414(07)81197-x

  日期：2007.12.1

  Isomeric, oxathiolone fused chalcones bearing 0-aminoalkyl side chain were synthesized by condensation of suitable benzoxathiolones with substituted benzaldehydes. The starting benzoxathiolones were prepared by O-alkylation of corresponding phenols with aminoalkyl chlorides, however, the reaction was often complicated by amino group catalyzed opening of the oxathiolone ring. The obtained chalcones were screened for antimicrobial and cytotoxic activity.
• New domino reaction. One pot synthesis of 4,7-dihydroxythioaurone derivatives from benzaldehydes and 4-acetyl-2-oxo-benz[1,3]oxathiole
  作者：Marek T. Konieczny、Wojciech Konieczny、Stefan Wolniewicz、Konstanty Wierzba、Yoshimitsu Suda、Paweł Sowiński

  DOI：10.1016/j.tet.2005.06.107

  日期：2005.9

  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.
• Synthesis of Isomeric, Oxathiolone Fused Chalcones, and Comparison of Their Activity toward Various Microorganisms and Human Cancer Cells Line
  作者：Marek Tadeusz Konieczny、Wojciech Konieczny、Michał Sabisz、Andrzej Skladanowski、Roland Wakieć、Ewa Augustynowicz-Kopeć、Zofia Zwolska

  DOI：10.1248/cpb.55.817

  日期：——

  Isomeric oxathiolone fused chalcones were prepared by condensation of appropriate acetylbenzo[1,3]oxathiol-2-ones with benzaldehydes under acidic conditions. The synthesized compounds were screened for cytotoxic activity using HeLa cells, as well as for antibacterial activity against Micrococcus luteus, Staphylococcus aureus, Salmonella typhimurium, Escherichia coli, Proteus vulgaris, antifungal activity against Candida albicans, and tuberculostatic activity against Mycobacterium tuberculosis H37Rv and Mycobacterium kansasii strains.

  在酸性条件下，通过将适当的乙酰苯并[1,3]氧硫杂环戊-2-酮与苯甲醛缩合，制备了同分异构的氧硫杂环戊酮融合查耳酮。利用 HeLa 细胞对合成的化合物进行了细胞毒性活性筛选，并对黄体微球菌、金黄色葡萄球菌、伤寒沙门氏菌、大肠杆菌、普通变形杆菌进行了抗菌活性筛选，对白色念珠菌进行了抗真菌活性筛选，对结核分枝杆菌 H37Rv 和堪萨斯分枝杆菌菌株进行了抗结核活性筛选。