3-Hydroxy-2,2-dimethyl-6-oxo-3,4-dihydro-2H,6H-1,5-dioxa-triphenylene-8-carboxylic acid ethyl ester | 708988-59-4

• 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: 3-Hydroxy-2,2-dimethyl-6-oxo-3,4-dihydro-2H,6H-1,5-dioxa-triphenylene-8-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-hydroxy-4,4-dimethyl-10-oxo-3,9-dioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),8(13),11,14,16-hexaene-12-carboxylate
• CAS: 708988-59-4
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: AARZTBZQBQUNEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-2,2-dimethyl-6-oxo-3,4-dihydro-2H,6H-1,5-dioxa-triphenylene-8-carboxylic acid ethyl ester 在 三苯基膦 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 3.0h， 以97%的产率得到ethyl 2,2-dimethyl-6-oxo-2H,6H-benzo[f]pyrano[2,3-h]chromene-8-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of the antioxidant and antiinflammatory activities of some benzo[l]khellactone derivatives and analogues

  摘要：

  Treatment of 3-hydroxy-beta-lapachone 4 with ylide 5 gave the coumarin derivative 7a, which was transformed to compounds 10-14. Compound 14 was then transformed to benzo[f]seselin 15 as well as to benzo[I]khellactones 16, 18 from which the title compounds 17, 19(I), 19(II), 20, 21(I) and 21(II) were prepared. All the tested compounds were found to interact with DPPH in a concentration and time dependent manner. All the tested compounds highly inhibited the soybean lipoxygenase, whereas compounds 12, 17 and 19(II) highly compete with DMSO for (OH)-O-.. Compounds 7a, 7b, 12 and 17 induced at 48.7-58.9% protection against carrageenin induced rat paw edema. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.01.003
• 作为产物：
  描述：

  3-Hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 、 乙氧甲酰基亚甲基三苯基膦 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到3-Hydroxy-2,2-dimethyl-6-oxo-3,4-dihydro-2H,6H-1,5-dioxa-triphenylene-8-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and evaluation of the antioxidant and antiinflammatory activities of some benzo[l]khellactone derivatives and analogues

  摘要：

  Treatment of 3-hydroxy-beta-lapachone 4 with ylide 5 gave the coumarin derivative 7a, which was transformed to compounds 10-14. Compound 14 was then transformed to benzo[f]seselin 15 as well as to benzo[I]khellactones 16, 18 from which the title compounds 17, 19(I), 19(II), 20, 21(I) and 21(II) were prepared. All the tested compounds were found to interact with DPPH in a concentration and time dependent manner. All the tested compounds highly inhibited the soybean lipoxygenase, whereas compounds 12, 17 and 19(II) highly compete with DMSO for (OH)-O-.. Compounds 7a, 7b, 12 and 17 induced at 48.7-58.9% protection against carrageenin induced rat paw edema. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.01.003

文献信息

• Synthesis and evaluation of the antioxidant and antiinflammatory activities of some benzo[l]khellactone derivatives and analogues
  作者：Demetrios N Nicolaides、Daman R Gautam、Konstantinos E Litinas、Dimitra J Hadjipavlou-Litina、Konstantina C Fylaktakidou

  DOI：10.1016/j.ejmech.2004.01.003

  日期：2004.4

  Treatment of 3-hydroxy-beta-lapachone 4 with ylide 5 gave the coumarin derivative 7a, which was transformed to compounds 10-14. Compound 14 was then transformed to benzo[f]seselin 15 as well as to benzo[I]khellactones 16, 18 from which the title compounds 17, 19(I), 19(II), 20, 21(I) and 21(II) were prepared. All the tested compounds were found to interact with DPPH in a concentration and time dependent manner. All the tested compounds highly inhibited the soybean lipoxygenase, whereas compounds 12, 17 and 19(II) highly compete with DMSO for (OH)-O-.. Compounds 7a, 7b, 12 and 17 induced at 48.7-58.9% protection against carrageenin induced rat paw edema. (C) 2004 Elsevier SAS. All rights reserved.