5-<<(4-bromo-2,5-dimethoxyphenyl)amino>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione | 133400-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-<<(4-bromo-2,5-dimethoxyphenyl)amino>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-[(4-bromo-2,5-dimethoxyphenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione；5-[(4-Bromo-2,5-dimethoxyanilino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[(4-bromo-2,5-dimethoxyanilino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 133400-93-8
• 化学式: C₁₅H₁₆BrNO₆
• 分子量: 386.199
• InChiKey: SUMYAJWDTXCIMN-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C(Solv: ethanol (64-17-5))
• 沸点：
  540.9±50.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-<<(4-bromo-2,5-dimethoxyphenyl)amino>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione 在 五氯化磷 、 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 21.33h， 生成 6-bromo-4-chloro-5,8-dimethoxyquinoline
  参考文献：
  名称：

  Synthesis of isoascididemin, a regioisomer of the marine alkaloid ascididemin

  摘要：

  The synthesis of isoascididemin, a regioisomer of the naturally occurring ascididemin, has been completed in nine steps from 2,5-dimethoxyaniline. The key steps feature a selective palladium(O)-catalyzed cross-coupling reaction of 6-bromo-5,8-dimethoxy-4-[(trifluoromethanesulfonyl)oxy]quinoline with N-(tert-butoxycarbonyl)-2-(trimethylstannyl)aniline promoted by Cu(I) and a hetero-Diels-Alder reaction of a quinoline-5,8-dione with acrolein N,N-dimethylhydrazone.

  DOI：

  10.1021/jo00011a011
• 作为产物：
  描述：

  5-{[(2,5-dimethoxyphenylamino)]methylidene}-2,2-dimethyl-4,6-dioxo-1,3-dioxane 在 溴 、 溶剂黄146 作用下， 以84%的产率得到5-<<(4-bromo-2,5-dimethoxyphenyl)amino>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Computational design, synthesis and biological evaluation of para-quinone-based inhibitors for redox regulation of the dual-specificity phosphatase Cdc25B

  摘要：

  根据原子电位线性组合（LCAP）方法设计了 Cdc25B 的醌类抑制剂。与已发表的假设相反，三种合成模型的生物活性和在还原介质中生成的过氧化氢与醌半波电位 E1/2 并不相关。

  DOI：

  10.1039/b806712k

文献信息

• GOMEZ-BENGOA, ENRIQUE;ECHAVARREN, ANTONIO M., J. ORG. CHEM., 56,(1991) N1, C. 3497-3501
  作者：GOMEZ-BENGOA, ENRIQUE、ECHAVARREN, ANTONIO M.

  DOI：——

  日期：——
• Synthesis of isoascididemin, a regioisomer of the marine alkaloid ascididemin
  作者：Enrique Gomez-Bengoa、Antonio M. Echavarren

  DOI：10.1021/jo00011a011

  日期：1991.5

  The synthesis of isoascididemin, a regioisomer of the naturally occurring ascididemin, has been completed in nine steps from 2,5-dimethoxyaniline. The key steps feature a selective palladium(O)-catalyzed cross-coupling reaction of 6-bromo-5,8-dimethoxy-4-[(trifluoromethanesulfonyl)oxy]quinoline with N-(tert-butoxycarbonyl)-2-(trimethylstannyl)aniline promoted by Cu(I) and a hetero-Diels-Alder reaction of a quinoline-5,8-dione with acrolein N,N-dimethylhydrazone.
• Computational design, synthesis and biological evaluation of para-quinone-based inhibitors for redox regulation of the dual-specificity phosphatase Cdc25B
  作者：Shahar Keinan、William D. Paquette、John J. Skoko、David N. Beratan、Weitao Yang、Sunita Shinde、Paul A. Johnston、John S. Lazo、Peter Wipf

  DOI：10.1039/b806712k

  日期：——

  Quinoid inhibitors of Cdc25B were designed based on the Linear Combination of Atomic Potentials (LCAP) methodology. In contrast to a published hypothesis, the biological activities and hydrogen peroxide generation in reducing media of three synthetic models did not correlate with the quinone half-wave potential, E1/2.

  根据原子电位线性组合（LCAP）方法设计了 Cdc25B 的醌类抑制剂。与已发表的假设相反，三种合成模型的生物活性和在还原介质中生成的过氧化氢与醌半波电位 E1/2 并不相关。