4,7-dimethyl-3,4-dihydropyrano[4,3-b]pyran-2,5-dione | 18735-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4,7-dimethyl-3,4-dihydropyrano[4,3-b]pyran-2,5-dione
• 英文别名: 4,7-Dimethyl-3,4-dihydropyrano[3,2-c]pyran-2,5-dione
• CAS: 18735-93-8
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: ALBKXSOBXZYFSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：

  4,7-dimethyl-3,4-dihydropyrano[4,3-b]pyran-2,5-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以95%的产率得到4,7-二甲基吡喃并[5,6-c]吡喃-2,5-二酮
  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-methyl-6-oxopyran-4-yl) (E)-but-2-enoate 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 以48%的产率得到4,7-dimethyl-3,4-dihydropyrano[4,3-b]pyran-2,5-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

文献信息

• A new method for enol lactone synthesis by a Michael addition/cyclization sequence
  作者：Kennosuke Itoh、Shuji Kanemasa

  DOI：10.1016/s0040-4039(03)00147-3

  日期：2003.2

  Reactions of cyclic 1,3-dicarbonyl compounds with 1-(2-alkenoyl)-4-bromo-3,5-dimethylpyrazoles under the double catalytic activation conditions using both catalytic amounts of Lewis acid and amine catalysts provide a new direct synthetic route to enol lactones. Thus, 1,3-cyclohexanedione is allowed to react with 4-bromo-1-crotonoyl-3,5-dimethylpyrazole, in tetrahydrofuran at room temperature in the

  环状1,3-二羰基化合物与1-（2-链烯酰基）-4-溴-3,5-二甲基吡唑在双催化活化条件下使用催化量的路易斯酸和胺催化剂的反应提供了一种新的直接合成途径烯醇内酯。因此，在两种催化量（各为10摩尔％）的高氯酸镍（II）存在下，在室温下使1，3-环己二酮与4-溴-1-巴豆酰基-3,5-二甲基吡唑在四氢呋喃中反应。六水合物和2,2,6,6-四甲基哌啶，以良好的收率得到4,7,7-三甲基-3,4,5,6,7,8-六氢苯并吡喃-2（H），5-二酮。在双催化活化条件以外的反应条件下，该反应不会进行或反应太慢。
• Enantioselective synthesis of enol lactones from tandem Michael addition/lactonization catalyzed by a chiral squaramide catalyst
  作者：Bo-Liang Zhao、Da-Ming Du

  DOI：10.1016/j.tetasy.2014.01.005

  日期：2014.2
• 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.