4-acetyl-5-[2'-(N,N-diethylamino)ethoxy]-1,3-benzoxathiol-2-one | 865851-36-1

• 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-[2'-(N,N-diethylamino)ethoxy]-1,3-benzoxathiol-2-one
• 英文别名: 4-acetyl-5-[2-(diethylamino)ethoxy]benzo[1,3]oxathiol-2-one；4-Acetyl-5-[2-(diethylamino)ethoxy]-1,3-benzoxathiol-2-one
• CAS: 865851-36-1
• 化学式: C₁₅H₁₉NO₄S
• 分子量: 309.386
• InChiKey: CDWPYZNCYCLNIC-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C(Solv: methanol (67-56-1))
• 沸点：
  450.9±55.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-acetyl-5-[2'-(N,N-diethylamino)ethoxy]-1,3-benzoxathiol-2-one 、 4-[2-(二甲胺基)乙氧基]苯甲醛 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以48%的产率得到5-[2-(diethylamino)ethoxy]-4-[3-(4'-(2-dimethylamino)ethoxyphenyl)acryloyl]benzo[1,3]oxathiol-2-one
  参考文献：
  名称：

  Synthesis of oxathiolone fused chalcones bearing O-aminoalkyl side chain. Comparison of stability of isomeric benzoxathiolones under alkylation reaction conditions

  摘要：

  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.

  DOI：

  10.1016/s0385-5414(07)81197-x
• 作为产物：
  描述：

  4-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one 、 2-二乙氨基氯乙烷盐酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以62%的产率得到4-acetyl-5-[2'-(N,N-diethylamino)ethoxy]-1,3-benzoxathiol-2-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