2,7-dimethyl-2,3-dihydropyrano[4,3-b]pyran-4,5-dione | 18735-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,7-dimethyl-2,3-dihydropyrano[4,3-b]pyran-4,5-dione
• 英文别名: 2,7-dimethyl-2,3-dihydro-pyrano[4,3-b]pyran-4,5-dione；2,3-Dihydro-2,7-dimethyl-4H,5H-pyrano-<4,3-b>-pyran-4,5-dion；2,3-Dihydro-2,7-dimethyl-4H,5H-pyrano-<4,3-b>pyran-4,5-dion；2,7-Dimethyl-2,3,4,5-tetrahydropyrano(4,3-b)pyran-4,5-dione；2,7-dimethyl-2,3-dihydropyrano[3,2-c]pyran-4,5-dione
• CAS: 18735-96-1
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: ZWGNATRKDFUMPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-dimethyl-2,3-dihydropyrano[4,3-b]pyran-4,5-dione 在 碘 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 以68%的产率得到2,7-dimethyl-4H-pyrano<3,2-c>-2H-pyran-4,5-dione
  参考文献：
  名称：

  Lewis acid mediated condensation reactions of α,β-unsaturated acids with 4-hydroxy-2-pyrones. A concise structural assignment of Fleischmann’s α,α-bispyrone and Praill’s α,γ-bispyrone

  摘要：

  Unambiguous assignments of Fleischmann's alpha,alpha-bispyrone 3 and Praill's alpha,gamma-bispyrone 6 have been carried out by exploring Lewis acid mediated condensation reactions of oc, B-unsaturated carboxylic acids with 4-hydroxy-2-pyrones. This protocol is shown to be useful for synthesis of a BCDE-ring tetracyclic analog of arisugacin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00057-5
• 作为产物：
  描述：

  2,2-dimethyl-6-(2-oxopropyl)-4H-1,3-dioxin-4-one 在 四氯化钛 作用下， 以 甲苯 、 1,1,2,2-四氯乙烷 为溶剂， 反应 3.75h， 生成 2,7-dimethyl-2,3-dihydropyrano[4,3-b]pyran-4,5-dione
  参考文献：
  名称：

  Synthesis and Herbicidal Activity Against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin

  摘要：

  报告了一种新的合成策略，用于获得（±）-3-去氧根毒素（2）。这种合成方法比以前文献中报道的方法更高效，同时在C-7和C-2位置引入不同侧链的多功能性也更高。所得化合物（±）-2对草类杂草牛草具有植物毒性，与天然植物毒素根毒素（1）相当。因此，（±）-2可以作为比1更实用的合成替代品，用于牛草控制的生物除草剂。

  DOI：

  10.3390/molecules24173193

文献信息

• Synthesis and Herbicidal Activity Against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin
  作者：Giulia Marsico、Maria Sabrina Ciccone、Marco Masi、Fabrizio Freda、Massimo Cristofaro、Antonio Evidente、Stefano Superchi、Patrizia Scafato

  DOI：10.3390/molecules24173193

  日期：——

  A novel synthetic strategy for obtainment of (±)-3-deoxyradicinin (2) is reported. This synthetic methodology is more efficient than those previously reported in the literature and also shows higher versatility towards the introduction of different side-chains at both C-7 and C-2. The obtained compound (±)-2 shows phytotoxicity against the grass-weed buffelgrass comparable to that of the natural phytotoxin radicinin (1). Therefore, (±)-2 can constitute a more practical synthetic alternative to 1 as bioherbicide for buffelgrass control.

  报告了一种新的合成策略，用于获得（±）-3-去氧根毒素（2）。这种合成方法比以前文献中报道的方法更高效，同时在C-7和C-2位置引入不同侧链的多功能性也更高。所得化合物（±）-2对草类杂草牛草具有植物毒性，与天然植物毒素根毒素（1）相当。因此，（±）-2可以作为比1更实用的合成替代品，用于牛草控制的生物除草剂。
• Lewis acid mediated condensation reactions of α,β-unsaturated acids with 4-hydroxy-2-pyrones. A concise structural assignment of Fleischmann’s α,α-bispyrone and Praill’s α,γ-bispyrone
  作者：Luke R Zehnder、Jason W Dahl、Richard P Hsung

  DOI：10.1016/s0040-4039(00)00057-5

  日期：2000.3

  Unambiguous assignments of Fleischmann's alpha,alpha-bispyrone 3 and Praill's alpha,gamma-bispyrone 6 have been carried out by exploring Lewis acid mediated condensation reactions of oc, B-unsaturated carboxylic acids with 4-hydroxy-2-pyrones. This protocol is shown to be useful for synthesis of a BCDE-ring tetracyclic analog of arisugacin. (C) 2000 Elsevier Science Ltd. All rights reserved.