5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2:5,4-b'>dipyran | 106038-24-8

• 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: 5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2:5,4-b'>dipyran
• 英文别名: 5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2-b:5,4-b'>dipyran；2,6-dihydro-5-methoxy-8-methylpyrano[3,2-g][1]benzopyran-2,6-dione；5-methoxy-8-methylpyrano[3,2-g]chromen-2,6-dione；5-Methoxy-8-methylpyrano[3,2-g]chromene-2,6-dione
• CAS: 106038-24-8
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: MJWKARBCOYYLJA-UHFFFAOYSA-N

物化性质

• 沸点：
  493.8±45.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2:5,4-b'>dipyran 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到7-Hydroxy-5-methoxy-6-(5-methyl-1H-pyrazol-3-yl)-chromen-2-one
  参考文献：
  名称：

  Soliman, Fouad M.; Khalil, Khairia M.; Elnaem, Shweekar I., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 60, # 3/4, p. 183 - 187

  摘要：

  DOI：
• 作为产物：
  描述：

  7-hydroxy-5-methoxy-2-methyl-6-[(phenylimino)methyl]-4H-chromen-4-one 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.0h， 生成 5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2:5,4-b'>dipyran
  参考文献：
  名称：

  磷叶立德化学。第 34 部分 Chromenone Phosphanylidene 和 Cyclobutylidene 衍生物的合成

  摘要：

  摘要 亲核磷杂草烯叶立德与visnaginone 和khellinone 反应得到相应的亚膦基和呋喃色烯衍生物。此外，吡喃色烯是从色烯甲醛与磷枯草烯的反应中获得的。另一方面，亚膦基-亚环丁基及其二聚体是由呋喃色烯甲醛与相同的鏻试剂反应产生的。图形概要

  DOI：

  10.1080/10426507.2011.600741

文献信息

• 4-Phenoxybutoxy-substituted heterocycles – A structure–activity relationship study of blockers of the lymphocyte potassium channel Kv1.3
  作者：Silke B. Bodendiek、Cédrick Mahieux、Wolfram Hänsel、Heike Wulff

  DOI：10.1016/j.ejmech.2008.10.033

  日期：2009.5

  The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC(50) of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC(50)s of 150 nM to 10 mu M in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC(50) 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Atta, Sanaa M. S.; Hafez, Taghrid S.; Mahran, Mohamed R., Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 80, # 1-4, p. 109 - 116
  作者：Atta, Sanaa M. S.、Hafez, Taghrid S.、Mahran, Mohamed R.

  DOI：——

  日期：——
• Chemistry of Phosphorus Ylides. Part 34 Synthesis of Chromenone Phosphanylidene and Cyclobutylidene Derivatives
  作者：Soher S. Maigali、Mohamed H. Arief、Marwa EL-Hussieny、Fouad M. Soliman

  DOI：10.1080/10426507.2011.600741

  日期：2012.2.1

  Abstract The reaction of nucleophilic phosphacumulene ylides with visnaginone and khellinone afforded the corresponding phosphanylidene and furochromene derivatives. Moreover, pyranochromenes were obtained from the reaction of chromene carbaldehydes with phosphacumulenes. On the other hand, the phosphanylidene-cyclobutylidenes and their dimers were produced from the reaction of furochromene carbaldehydes

  摘要 亲核磷杂草烯叶立德与visnaginone 和khellinone 反应得到相应的亚膦基和呋喃色烯衍生物。此外，吡喃色烯是从色烯甲醛与磷枯草烯的反应中获得的。另一方面，亚膦基-亚环丁基及其二聚体是由呋喃色烯甲醛与相同的鏻试剂反应产生的。图形概要
• Soliman, Fouad M.; Khalil, Khairia M.; Elnaem, Shweekar I., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 60, # 3/4, p. 183 - 187
  作者：Soliman, Fouad M.、Khalil, Khairia M.、Elnaem, Shweekar I.

  DOI：——

  日期：——