1-benzyloxy-3-methylnaphthalen-4-yl acetate | 53772-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-benzyloxy-3-methylnaphthalen-4-yl acetate
• 英文别名: (2-Methyl-4-phenylmethoxynaphthalen-1-yl) acetate
• CAS: 53772-20-6
• 化学式: C₂₀H₁₈O₃
• 分子量: 306.361
• InChiKey: XTDAJWAHMWBSCD-UHFFFAOYSA-N

物化性质

• 熔点：
  103.8-104.9 °C
• 沸点：
  469.5±33.0 °C(predicted)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-3-methylnaphthalen-4-yl acetate 在 sodium hydroxide 、 tetrafluoroboric acid 、 sodium thiosulfate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 6.08h， 生成 3,6,9-trimethyl-naphtho[1,8-bc]pyran-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：

  维生素 K4 在 potassium carbonate 、 叔丁胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 5.0h， 生成 1-benzyloxy-3-methylnaphthalen-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

• Synthesis of menaquinones
  作者：Clinton D. Snyder、Henry Rapoport

  DOI：10.1021/ja00833a035

  日期：1974.12
• US3948958A
  申请人：——

  公开号：US3948958A

  公开（公告）日：1976-04-06
• US4060558A
  申请人：——

  公开号：US4060558A

  公开（公告）日：1977-11-29