7,8-diacetonyloxy-4-methylcoumarin | 185453-42-3

• 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: 7,8-diacetonyloxy-4-methylcoumarin
• 英文别名: 7,8-bis-acetonyloxy-4-methyl-coumarin；7,8-Bis-acetonyloxy-4-methyl-cumarin；4-Methyl-7,8-bis(2-oxopropoxy)chromen-2-one
• CAS: 185453-42-3
• 化学式: C₁₆H₁₆O₆
• 分子量: 304.299
• InChiKey: LBUUMASAXSEDTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,8-diacetonyloxy-4-methylcoumarin 在 四丁基溴化铵 、 sodium hydroxide 、 magnesium iodide 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 20.0h， 生成 4,4'-dimethyl-8-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)xanthotoxol
  参考文献：
  名称：

  Synthesis and biological evaluation of glycosylated psoralen derivatives

  摘要：

  A novel route for the efficient synthesis of a target psoralen moiety, 4,4'-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photoinduced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.090
• 作为产物：
  描述：

  邻苯三酚 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 7,8-diacetonyloxy-4-methylcoumarin
  参考文献：
  名称：

  Synthesis and biological evaluation of glycosylated psoralen derivatives

  摘要：

  A novel route for the efficient synthesis of a target psoralen moiety, 4,4'-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photoinduced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.090

文献信息

• Reaction of α-Haloketones with<i>ortho</i>-Dihydroxy-2<i>H</i>-1-benzopyran-2-ones. Formation of α-Pyrano-1,5-benzodioxapines-A New Heterocyclic System
  作者：Avula Prashant、Gazaula DavidKrupadanam、Roberto R. Gil、Lee-Juian Lin、Geoffrey A. Cordell

  DOI：10.1080/00397919608004791

  日期：1996.12

  Abstract Reaction of 7,8-dihydroxy-2H-1-benzopyran-2-one, and its 4-methyl derivative, with α-haloketones affords α-pyrano-1,5-benzodioxapines, while 3-chloro-4-methyl-7,8-dihydroxy-2H-1-benzopyran-2-one gives α-pyrano-1,4-benzodioxane. The structures of the compounds were deduced using a combination of 1H nmr, 13C nmr (BB, DEPT), HETCOR, NOESY, and selective INEPT techniques and molecular modeling

  摘要 7,8-二羟基-2H-1-苯并吡喃-2-one 及其4-甲基衍生物与α-卤代酮反应生成α-吡喃-1,5-苯并二氧杂茚，而3-氯-4-甲基- 7,8-二羟基-2H-1-苯并吡喃-2-one 生成 α-吡喃-1,4-苯并二恶烷。化合物的结构是使用 1H nmr、13C nmr (BB, DEPT)、HETCOR、NOESY 和选择性 INEPT 技术和分子建模的组合推导出来的。
• Sakai; Kato, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1935, vol. 55, p. 785,787; dtsch. Ref. S. 151
  作者：Sakai、Kato

  DOI：——

  日期：——
• Synthesis and biological evaluation of glycosylated psoralen derivatives
  作者：Chao-Yue Chen、Jian-Guo Sun、Fei-Yan Liu、Kwok-Pui Fung、Ping Wu、Zhi-Zhen Huang

  DOI：10.1016/j.tet.2012.01.090

  日期：2012.3

  A novel route for the efficient synthesis of a target psoralen moiety, 4,4'-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photoinduced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. (C) 2012 Elsevier Ltd. All rights reserved.