2,6-dimethyl-1,4-naphthoquinone-2,3-epoxide | 73377-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-dimethyl-1,4-naphthoquinone-2,3-epoxide
• 英文别名: 2,3-epoxy-2,6-dimethyl-2,3-dihydro-[1,4]naphthoquinone；2,3-Epoxy-2,6-dimethyl-2,3-dihydro-[1,4]naphthochinon；4,7a-dimethyl-1aH-naphtho[2,3-b]oxirene-2,7-dione
• CAS: 73377-84-1
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: CLOOWXSGPYVYQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-1,4-naphthoquinone-2,3-epoxide 、 乙醚 、 苯 、 烯丙基溴化镁 生成 3-hydroxy-2,6-dimethyl-[1,4]naphthoquinone 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Naphthoquinones of the Vitamin K₁ Type of Structure

  摘要：

  DOI：

  10.1021/ja01266a068
• 作为产物：
  描述：

  2,6-dimethyl-1,4-naphthoquinone 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以93%的产率得到2,6-dimethyl-1,4-naphthoquinone-2,3-epoxide
  参考文献：
  名称：

  Epoxides related to dioncoquinone B: Synthesis, activity against multiple myeloma cells, and search for the target protein

  摘要：

  Epoxide 2b is an analog of the synthetic intermediate 2a en route to the polyketide-derived antitumoral naphthoquinone dioncoquinone B (1), isolated from cell cultures of the tropical liana Triphyophyllum peltatum (Dioncophyllaceae). Compound 2b was found to induce strong apoptosis in multiple myeloma cells at a concentration (EC50 = 3.5 mu M), distinctly lower than that of 1 and any related analog, without exerting significant toxicity against normal blood cells. Preliminary studies showed that 2b follows different SAR rules as compared to the naphthoquinones. Among the series of synthesized epoxides, 2b was the most active one and was thus, after biotinylation, subjected to mass spectrometry-based affinity capture experiments aiming at the identification of target proteins. The MS data revealed 2b to address proteins that are associated with stress regulation processes which are critical for multiple myeloma cell survival. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.04.056

文献信息

• Catalytic asymmetric induction in oxidation reactions. Synthesis of optically active epoxynaphthoquinones
  作者：Henk Pluim、Hans Wynberg

  DOI：10.1021/jo01300a047

  日期：1980.6