ethyl 2,2-dimethyl-6-oxo-2H,6H-benzo[f]pyrano[2,3-h]chromene-8-carboxylate | 476213-11-3

• 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: ethyl 2,2-dimethyl-6-oxo-2H,6H-benzo[f]pyrano[2,3-h]chromene-8-carboxylate
• 英文别名: Ethyl 4,4-dimethyl-10-oxo-3,9-dioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),5,8(13),11,14,16-heptaene-12-carboxylate
• CAS: 476213-11-3
• 化学式: C₂₁H₁₈O₅
• 分子量: 350.371
• InChiKey: WKSIGLDLTYZALZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-dimethyl-6-oxo-2H,6H-benzo[f]pyrano[2,3-h]chromene-8-carboxylate 在 吡啶 、 氢氧化钾 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 为溶剂， 反应 31.67h， 生成 ethyl cis-3-hydroxy-4{[(4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]hept-1-yl)carbonyl]oxy}-3,4-dihydro-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：

  3,4-二氢-2,2-二甲基-2H-萘并[1,2-B]吡喃-5,6-二酮 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 ethyl 2,2-dimethyl-6-oxo-2H,6H-benzo[f]pyrano[2,3-h]chromene-8-carboxylate
  参考文献：
  名称：

  Synthesis of some 3,4-dihydro-2H-benzo[f]pyrano[2,3-h]chromen-6-one derivatives

  摘要：

  邻醌 16-18 与叶立德 19 的反应以中等至良好的收率 (62-80%) 得到化合物 5-7，其进一步脱乙氧基羰基化为化合物 28-30，收率 53-66%。化合物6、7和29进一步转化为化合物31-35。还报道了新化合物10、11、16和27的制备。

  DOI：

  10.1039/b202640f

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.
• Synthesis of some 3,4-dihydro-2H-benzo[f]pyrano[2,3-h]chromen-6-one derivatives
  作者：Demetrios N. Nicolaides、Daman R. Gautam、Konstantinos E. Litinas、Theodora Papamehael

  DOI：10.1039/b202640f

  日期：2002.6.7

  Reactions of o-quinones 16–18 with ylide 19 afforded compounds 5–7 in moderate to good yields (62–80%), which were further de-ethoxycarbonylated to compounds 28–30 in 53–66% yield. Compounds 6, 7 and 29 were further transformed into compounds 31–35. The preparation of the novel compounds 10, 11, 16 and 27 is also reported.

  邻醌 16-18 与叶立德 19 的反应以中等至良好的收率 (62-80%) 得到化合物 5-7，其进一步脱乙氧基羰基化为化合物 28-30，收率 53-66%。化合物6、7和29进一步转化为化合物31-35。还报道了新化合物10、11、16和27的制备。