8-(trifluoromethyl)-1H-benzo[e]imidazo[1,2-b][1,2,4]thiadiazin-2(3H)-one-5,5-dioxide | 1605279-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 8-(trifluoromethyl)-1H-benzo[e]imidazo[1,2-b][1,2,4]thiadiazin-2(3H)-one-5,5-dioxide
• 英文别名: 5,5-Dioxo-8-(trifluoromethyl)-1,3-dihydroimidazo[1,2-b][1,2,4]benzothiadiazin-2-one；5,5-dioxo-8-(trifluoromethyl)-1,3-dihydroimidazo[1,2-b][1,2,4]benzothiadiazin-2-one
• CAS: 1605279-89-7
• 化学式: C₁₀H₆F₃N₃O₃S
• 分子量: 305.237
• InChiKey: DAIZDAOOYGJDLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Fmoc-甘氨酸 、 2-硝基-4-(三氟甲基)苯磺酰氯 、 Fmoc-异硫氰酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 8-(trifluoromethyl)-1H-benzo[e]imidazo[1,2-b][1,2,4]thiadiazin-2(3H)-one-5,5-dioxide
  参考文献：
  名称：

  Solid-Phase Synthesis of Anagrelide Sulfonyl Analogues

  摘要：

  Simple solid-phase synthesis of 3,10-dihydro-2H-benzo[e]imidazo[1,2-b][1,2,4]thiadiazin-2-one 5,5-dioxides is described, with Fmoc-α-amino acids and 2-nitrobenzenesulfonyl chlorides (2-NosCls) being the key building blocks. Fmoc-α-amino acids were immobilized on Wang resin and transformed to the corresponding 2-nitrobenzenesulfonamides in two steps. After reduction of the nitro group, Fmoc-thioureas were synthesized followed by cyclization of the 1,2,4-benzothiadiazine-1,1-dioxide scaffold with diisopropylcarbodiimide (DIC). Cleavage of the Fmoc protecting group followed by spontaneous cyclative cleavage gave the target products in excellent crude purity.

  DOI：

  10.1021/co400119c

文献信息

• Solid-Phase Synthesis of Anagrelide Sulfonyl Analogues
  作者：Claire McMaster、Veronika Fülöpová、Igor Popa、Martin Grepl、Miroslav Soural

  DOI：10.1021/co400119c

  日期：2014.5.12

  Simple solid-phase synthesis of 3,10-dihydro-2H-benzo[e]imidazo[1,2-b][1,2,4]thiadiazin-2-one 5,5-dioxides is described, with Fmoc-α-amino acids and 2-nitrobenzenesulfonyl chlorides (2-NosCls) being the key building blocks. Fmoc-α-amino acids were immobilized on Wang resin and transformed to the corresponding 2-nitrobenzenesulfonamides in two steps. After reduction of the nitro group, Fmoc-thioureas were synthesized followed by cyclization of the 1,2,4-benzothiadiazine-1,1-dioxide scaffold with diisopropylcarbodiimide (DIC). Cleavage of the Fmoc protecting group followed by spontaneous cyclative cleavage gave the target products in excellent crude purity.