1-hydroxy-3-ethylnaphthalen-4-yl acetate | 916432-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-hydroxy-3-ethylnaphthalen-4-yl acetate
• 英文别名: (2-Ethyl-4-hydroxynaphthalen-1-yl) acetate
• CAS: 916432-84-3
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: YBLKGXXAJLVGLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3-ethylnaphthalen-4-yl acetate 在 sodium hydroxide 、 tetrafluoroboric acid 、 potassium carbonate 、 sodium thiosulfate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.08h， 生成 5-benzyl-9-ethyl-3-methylbenzo[de]chromene-7,8-dione
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 9‐Substituted Benzo[de]chromene‐7,8‐dione and 5‐Benzyl‐9‐substituted Benzo[de]chromene‐7,8‐dione

  摘要：

  New Mansonone analogues of 9-substitued benzo[ de] chromene-7,8-dione 5b-e and 5-benzyl-9-substitued benzo[ de] chromene-7,8-dione 6a-e were prepared through a modified route. The first step involved a bulky base t-butylamine mediated regioselective deacetylation of 2-substituted-1,4-naphth-diyl diacetate, resulting in obtaining of monoacetate 4-acetate 2 in high yield. The mechanism of cyclization, debenzylation, and oxidation for the formation of 5a - e and 6a - e were discussed. The cytotoxicity of the prepared compounds 5 and 6 were comparable with naturally occurring Mansonone F.

  DOI：

  10.1080/00397910600764683
• 作为产物：
  描述：

  2-ethyl-1,4-naphthalenediyl diacetate 在 叔丁胺 作用下， 以 甲醇 为溶剂， 以85%的产率得到1-hydroxy-3-ethylnaphthalen-4-yl acetate
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 9‐Substituted Benzo[de]chromene‐7,8‐dione and 5‐Benzyl‐9‐substituted Benzo[de]chromene‐7,8‐dione

  摘要：

  New Mansonone analogues of 9-substitued benzo[ de] chromene-7,8-dione 5b-e and 5-benzyl-9-substitued benzo[ de] chromene-7,8-dione 6a-e were prepared through a modified route. The first step involved a bulky base t-butylamine mediated regioselective deacetylation of 2-substituted-1,4-naphth-diyl diacetate, resulting in obtaining of monoacetate 4-acetate 2 in high yield. The mechanism of cyclization, debenzylation, and oxidation for the formation of 5a - e and 6a - e were discussed. The cytotoxicity of the prepared compounds 5 and 6 were comparable with naturally occurring Mansonone F.

  DOI：

  10.1080/00397910600764683

文献信息

• Syntheses of Naphthoquinone Compounds Using Chromium Carbonyl Carbene Complexes
  作者：Masakazu Yamashita、Takahiro Ohishi

  DOI：10.1246/bcsj.66.1187

  日期：1993.4

  The chromium carbonyl carbene complexes bearing an acetoxyl group and a phenyl substituent were found to react smoothly with acetylene compounds to produce naphthoquinone derivatives in good yields after oxidation. This cycloaddition reaction proceeded regioselectively and several naphthoquinones were prepared selectively from the complex and unsymmetrical acetylenes.

  发现带有乙酰氧基和苯基取代基的铬羰基卡宾配合物可与乙炔化合物顺利反应，氧化后以良好的产率生成萘醌衍生物。这种环加成反应是区域选择性地进行的，并且从复杂的和不对称的乙炔中选择性地制备了几种萘醌。