ethyl 2-methyl-4,11-dipropoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate | 1082607-59-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: ethyl 2-methyl-4,11-dipropoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate
• CAS: 1082607-59-7
• 化学式: C₂₆H₂₆O₇
• 分子量: 450.488
• InChiKey: ZDFDYQMOCIVNQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.04
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-4,11-dipropoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.5h， 以72%的产率得到2-methyl-5,10-dioxo-4,11-dipropoxyanthra[2,3-b]furan-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and fluorescence of anthra[2,3-b]furan-5,10-dione derivatives

  摘要：

  4,11-Dialkoxyanthra[2,3-b]furan-5,10-diones containing various substituents in the 3-position were synthesized. Reactions of these compounds with primary and secondary amines resulted in nucleophilic replacement of one or two alkoxy groups by the corresponding amine residues. 4,11-Dialkoxy derivatives of anthra[2,3-b]furan-5,10-dione showed fluorescence with large Stokes shifts (170-200 nm).

  DOI：

  10.1134/s1070428007110164
• 作为产物：
  描述：

  1-碘代丙烷 、 ethyl 4,11-dihydroxy-2-methyl-5,10-dioxoanthra[2,3-b]furan-3-carboxylate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以66%的产率得到ethyl 2-methyl-4,11-dipropoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate
  参考文献：
  名称：

  Synthesis and fluorescence of anthra[2,3-b]furan-5,10-dione derivatives

  摘要：

  4,11-Dialkoxyanthra[2,3-b]furan-5,10-diones containing various substituents in the 3-position were synthesized. Reactions of these compounds with primary and secondary amines resulted in nucleophilic replacement of one or two alkoxy groups by the corresponding amine residues. 4,11-Dialkoxy derivatives of anthra[2,3-b]furan-5,10-dione showed fluorescence with large Stokes shifts (170-200 nm).

  DOI：

  10.1134/s1070428007110164

文献信息

• Heterocyclic analogs of 5,12-naphtacenequinone 13*. Synthesis of 4,11-diaminoanthra[2,3-b]furan-5,10-diones and sulfur-containing analogs
  作者：Alexander S. Tikhomirov、Eugeny E. Bykov、Yury N. Luzikov、Alexander M. Korolev、Andrey E. Shchekotikhin

  DOI：10.1007/s10593-016-1968-6

  日期：2016.10

  We have developed an effective method for the synthesis of 4,11-diaminoanthra[2,3-b]furan-5,10-dione and 4,11-diaminoanthra[2,3-b]-thiophene-5,10-dione derivatives based on the substitution of 4,11-alkoxy groups with n-butylamine and subsequent oxidative dealkylation of n-butylamino groups via treatment with tetrabutylammonium hydroxide in DMSO.

  我们已经开发出一种合成4,11-二氨基蒽[2,3- b ]呋喃-5,10-二酮和4,11-二氨基蒽[2,3 - b ]-噻吩-5,10-二酮的有效方法衍生物是基于用正丁胺取代4,11-烷氧基，然后通过在DMSO中用氢氧化四丁铵处理正丁氨基的氧化脱烷基而得到的衍生物。