2-(1-hydroxy-3,4-dioxonaphthalen-2-yl)acetaldehyde | 52422-60-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-hydroxy-3,4-dioxonaphthalen-2-yl)acetaldehyde
• 英文别名: 1,4-dihydro-3-hydroxy-1,4-dioxo-2-naphthaleneacetaldehyde
• CAS: 52422-60-3
• 化学式: C₁₂H₈O₄
• 分子量: 216.193
• InChiKey: IPNLDANGCFDNDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(1-hydroxy-3,4-dioxonaphthalen-2-yl)acetaldehyde 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以80%的产率得到(E)-2-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalene-2-yl)vinyl acetate
  参考文献：
  名称：

  Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol

  摘要：

  Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is also reported. The antitumoral activity of the tested compounds on human DU-145 prostate carcinoma cells was evaluated following XTT assay. The results revealed that 2-(1-methylethenyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (5), beta-lapachone (10) and dehydro-beta-lapachone diacetate (11) showed 100% inhibition at 25 mu g/ml. All the tested samples showed dose-dependent activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.053
• 作为产物：
  描述：

  黄钟花醌 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到2-(1-hydroxy-3,4-dioxonaphthalen-2-yl)acetaldehyde
  参考文献：
  名称：

  Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol

  摘要：

  Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is also reported. The antitumoral activity of the tested compounds on human DU-145 prostate carcinoma cells was evaluated following XTT assay. The results revealed that 2-(1-methylethenyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (5), beta-lapachone (10) and dehydro-beta-lapachone diacetate (11) showed 100% inhibition at 25 mu g/ml. All the tested samples showed dose-dependent activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.053