2-chloro-6-phenyl-furo[2,3-b]pyrazine-7-carboxylic acid methyl ester | 1369514-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2-chloro-6-phenyl-furo[2,3-b]pyrazine-7-carboxylic acid methyl ester
• 英文别名: methyl 2-chloro-6-phenylfuro[3,2-b]pyrazine-7-carboxylate
• CAS: 1369514-32-8
• 化学式: C₁₄H₉ClN₂O₃
• 分子量: 288.69
• InChiKey: ORCDHADUKISWJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.22
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  AcAla-NH2 、 2-chloro-6-phenyl-furo[2,3-b]pyrazine-7-carboxylic acid methyl ester 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以61%的产率得到methyl 2-(2-acetamidopropanamido)-6-phenylfuro[3,2-b]pyrazine-7-carboxylate
  参考文献：
  名称：

  Synthesis of functionalized furopyrazines as restricted dipeptidomimetics

  摘要：

  Herein, an efficient synthetic approach to a furopyrazine scaffold with four points of diversity, starting from 2(1H)-pyrazinones, with dipeptomimetic properties, is presented. R-groups corresponding to amino acid side chains were introduced during the 2(1H)-pyrazinone and subsequent furopyrazine formation. The furopyrazine scaffold was further functionalized with an amino- and a carboxy-terminus resulting in a conformationally restricted dipeptidomimetic scaffold. The carboxy-terminus was introduced via a chemoselective vinylation of the 7-position followed by oxidative cleavage, while the amino-terminus was obtained via Buchwald-Hartwig amidation of the 2-position of the scaffold. The versatility of the synthetic method was demonstrated by the synthesis of a small library of diversely substituted furopyrazines having various amino acid side chains on the four points of diversity. Evaluation with an X-ray structure of the scaffold and computational analysis supports the exploitation of the furopyrazine scaffold as a restricted dipeptide mimic, which can mimic the two central residues of a beta-turn. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.022
• 作为产物：
  描述：

  在 sodium chlorite 、 sodium periodate 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 8.0h， 生成 2-chloro-6-phenyl-furo[2,3-b]pyrazine-7-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of functionalized furopyrazines as restricted dipeptidomimetics

  摘要：

  Herein, an efficient synthetic approach to a furopyrazine scaffold with four points of diversity, starting from 2(1H)-pyrazinones, with dipeptomimetic properties, is presented. R-groups corresponding to amino acid side chains were introduced during the 2(1H)-pyrazinone and subsequent furopyrazine formation. The furopyrazine scaffold was further functionalized with an amino- and a carboxy-terminus resulting in a conformationally restricted dipeptidomimetic scaffold. The carboxy-terminus was introduced via a chemoselective vinylation of the 7-position followed by oxidative cleavage, while the amino-terminus was obtained via Buchwald-Hartwig amidation of the 2-position of the scaffold. The versatility of the synthetic method was demonstrated by the synthesis of a small library of diversely substituted furopyrazines having various amino acid side chains on the four points of diversity. Evaluation with an X-ray structure of the scaffold and computational analysis supports the exploitation of the furopyrazine scaffold as a restricted dipeptide mimic, which can mimic the two central residues of a beta-turn. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.022