1-hydroxy-3-(2-chlorobenzyl)naphthalen-4-yl acetate | 916432-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-hydroxy-3-(2-chlorobenzyl)naphthalen-4-yl acetate
• 英文别名: [2-[(2-Chlorophenyl)methyl]-4-hydroxynaphthalen-1-yl] acetate
• CAS: 916432-87-6
• 化学式: C₁₉H₁₅ClO₃
• 分子量: 326.779
• InChiKey: UBIWKZQIYXTTPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-(2-chlorobenzyl)naphthalen-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-(2-chlorobenzyl)-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-(2-chlorobenzyl)-1,4-naphthalenediyl diacetate 在 叔丁胺 作用下， 以 甲醇 为溶剂， 以78%的产率得到1-hydroxy-3-(2-chlorobenzyl)naphthalen-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