1-Methyl-3,4-dihydrothieno[3,2-e][1,4]diazepine-2,5-dione | 1086383-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烯杂卓类
• 英文名称: 1-Methyl-3,4-dihydrothieno[3,2-e][1,4]diazepine-2,5-dione
• 英文别名: 1-methyl-3,4-dihydrothieno[3,2-e][1,4]diazepine-2,5-dione
• CAS: 1086383-82-5
• 化学式: C₈H₈N₂O₂S
• 分子量: 196.23
• InChiKey: AXMQMMVAGDJNFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Methyl-3,4-dihydrothieno[3,2-e][1,4]diazepine-2,5-dione 、 二碳酸二叔丁酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.08h， 以83%的产率得到tert-butyl 2,3-dihydro-1-methyl-2,5-dioxo-1H-thieno[3,2-e]-[1,4]diazepine-4(5H)-carboxylate
  参考文献：
  名称：

  From Thienodiazepinediones to Thienopyridinones: Flexible Synthesis of Substituted Thieno[3,2-e][1,4]diazepinones and 6-Aminothieno[3,2-b]pyridinones

  摘要：

  N-Substituted thienodiazepinedione opening with a series of organomagnesium bromides allowed the subsequent cyclization to the seven-membered ring thieno[3,2-e][1,4]diazepinone in 52-99% yields or to the six-membered ring thieno[3,2-b]pyridinones in 45-55% yields. Effective syntheses introducing considerable diversity onto these valuable scaffolds are described.

  DOI：

  10.1021/jo900627a
• 作为产物：
  描述：

  2-[[3-(Methylamino)thiophene-2-carbonyl]amino]acetic acid 在 溶剂黄146 作用下， 生成 1-Methyl-3,4-dihydrothieno[3,2-e][1,4]diazepine-2,5-dione
  参考文献：
  名称：

  Valuable Versatile Reactivity of Thiaisatoic Anhydrides: Expedient Solid­Phase Synthesis of Thieno[1,4]diazepine-2,5-diones

  摘要：

  本文描述了一种合成取代的噻吩并[3,2-e][1,4]二氮杂环庚烯-2,5-二酮类似物的便捷途径。在溶液中证明，硫代异硫氰酸酐及其N-烷基化类似物在碱性条件下与氨基酸发生相反的反应。利用这一多样的反应性，开发了一种高效的固相支持策略。Wang树脂结合的硫代异硫氰酸酐与N-烷基化的α-氨基酸反应，环化并有效地从聚合物中裂解，得到了纯度为83-99%、产率为71-95%的噻吩并[3,2-e][1,4]二氮杂环庚烯-2,5-二酮的初步集合。

  DOI：

  10.1055/s-2008-1078210

文献信息

• Valuable Versatile Reactivity of Thiaisatoic Anhydrides: Expedient Solid­Phase Synthesis of Thieno[1,4]diazepine-2,5-diones
  作者：Vincent Lisowski、Yann Brouillette、Pascal Verdié、Jean Martinez

  DOI：10.1055/s-2008-1078210

  日期：——

  An expedient route for the generation of substituted thieno[3,2-e][1,4]diazepine-2,5-dione analogues is described herein. It was demonstrated in solution that thiaisatoic anhydride and its N-alkylated equivalents react in opposite ways with amino acids in basic conditions. This versatile reactivity was used to develop an efficient strategy on solid support. Wang resin-bound thiaisatoic anhydride was coupled with N-alkylated α-amino acids, cyclo-condensed and effectively cleaved from the polymer to provide a preliminary collection of thieno[3,2-e][1,4]diazepine-2,5-diones in 83-99% purity and 71-95% yield.

  本文描述了一种合成取代的噻吩并[3,2-e][1,4]二氮杂环庚烯-2,5-二酮类似物的便捷途径。在溶液中证明，硫代异硫氰酸酐及其N-烷基化类似物在碱性条件下与氨基酸发生相反的反应。利用这一多样的反应性，开发了一种高效的固相支持策略。Wang树脂结合的硫代异硫氰酸酐与N-烷基化的α-氨基酸反应，环化并有效地从聚合物中裂解，得到了纯度为83-99%、产率为71-95%的噻吩并[3,2-e][1,4]二氮杂环庚烯-2,5-二酮的初步集合。
• From Thienodiazepinediones to Thienopyridinones: Flexible Synthesis of Substituted Thieno[3,2-<i>e</i>][1,4]diazepinones and 6-Aminothieno[3,2-<i>b</i>]pyridinones
  作者：Yann Brouillette、Jean Martinez、Vincent Lisowski

  DOI：10.1021/jo900627a

  日期：2009.7.17

  N-Substituted thienodiazepinedione opening with a series of organomagnesium bromides allowed the subsequent cyclization to the seven-membered ring thieno[3,2-e][1,4]diazepinone in 52-99% yields or to the six-membered ring thieno[3,2-b]pyridinones in 45-55% yields. Effective syntheses introducing considerable diversity onto these valuable scaffolds are described.