2-acetoxymethyl-1,4-dimethoxynaphthalene | 246543-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-acetoxymethyl-1,4-dimethoxynaphthalene
• 英文别名: (1,4-Dimethoxynaphthalen-2-yl)methyl acetate；(1,4-dimethoxynaphthalen-2-yl)methyl acetate
• CAS: 246543-81-7
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: RICUKAOLJGOHMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetoxymethyl-1,4-dimethoxynaphthalene 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.13h， 以95%的产率得到2-acetoxymethyl-[1,4]naphthoquinone
  参考文献：
  名称：

  Synthesis of Quinones from Hydroquinone Dimethyl Ethers. Oxidative Demethylation with Cobalt(III) Fluoride

  摘要：

  用三氟化钴对1,4-二甲氧基萘和1,4-二甲氧基苯衍生物进行氧化脱甲基反应，能够获得良好至极佳的产率，从而得到相应的萘醌和苯醌衍生物。

  DOI：

  10.1055/s-1999-2875
• 作为产物：
  描述：

  1,4-二羟基萘 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 水 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 50.5h， 生成 2-acetoxymethyl-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Synthesis of Quinones from Hydroquinone Dimethyl Ethers. Oxidative Demethylation with Cobalt(III) Fluoride

  摘要：

  用三氟化钴对1,4-二甲氧基萘和1,4-二甲氧基苯衍生物进行氧化脱甲基反应，能够获得良好至极佳的产率，从而得到相应的萘醌和苯醌衍生物。

  DOI：

  10.1055/s-1999-2875

文献信息

• Development of Novel Quinone Phosphorodiamidate Prodrugs Targeted to DT-Diaphorase
  作者：Carolee Flader、Jiwen Liu、Richard F. Borch

  DOI：10.1021/jm000179o

  日期：2000.8.1

  A series of naphthoquinone and benzimidazolequinone phosphorodiamidates has been synthesized and studied as potential cytotoxic prodrugs activated by DT-diaphorase. Reduction of the quinone moiety in the target compounds was expected to provide a pathway for expulsion of the phosphoramide mustard alkylating agent. All of the compounds synthesized were excellent substrates for purified human DT-diaphorase (k(cat)/K-m = 3 x 10(7) - 3 x 10(8) M-1 s(-1)). The naphthoquinones were toxic to both HT-29 and BE human colon cancer cell lines in a clonogenic assay; however, cytotoxicity did not correlate with DT-diaphorase activity in these cell lines. The benzimidazolequinone analogues were 1-2 orders of magnitude less cytotoxic than the naphthoquinone analogues. Chemical reduction of the naphthoquinone led to rapid expulsion of the phosphorodiamidate anion; in contrast, the benzimidazole reduction product was stable. Michael addition of glutathione and other sulfur nucleophiles provides an alternate mechanism for activation of the naphthoquinone phosphorodiamidates, and this mechanism may contribute to the cytotoxicity of these compounds.