(3S)-6-acetyl-3-methyl-3,4-dihydrothieno[2,3-b]pyrazin-2(1H)-one | 433212-79-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S)-6-acetyl-3-methyl-3,4-dihydrothieno[2,3-b]pyrazin-2(1H)-one
• 英文别名: (3S)-6-acetyl-3-methyl-3,4-dihydro-1H-thieno[2,3-b]pyrazin-2-one
• CAS: 433212-79-4
• 化学式: C₉H₁₀N₂O₂S
• 分子量: 210.257
• InChiKey: LBBYQVGCIFFBNO-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲酸乙烯酯 、 (3S)-6-acetyl-3-methyl-3,4-dihydrothieno[2,3-b]pyrazin-2(1H)-one 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以46%的产率得到(3S)-vinyl 6-acetyl-3-methyl-2-oxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine-4-carboxylate
  参考文献：
  名称：

  Preparation of Thieno[2,3-b]pyrazines as Bioisosteres for Quinoxaline Derivatives wiht Reverse Transcriptase Inhibition

  摘要：

  Replacement of the fused aromatic moiety in GW-420867X, a HIV-1 specific nonnucleoside reverse transcriptase inhibitor, with thiophene provided 2-oxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine derivatives. The synthesis starts with the reaction of 5-acyl-2-chloro-3-nitrothiophene and different amino acid derivatives. The resulting substitution products are reduced, cyclized and N-acylated to give the desired compounds (27 - 33).

  DOI：

  10.3987/com-01-9371
• 作为产物：
  描述：

  1-(5-氯-4-硝基-2-噻吩)-1-乙酮 在 铁粉 、 potassium carbonate 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 17.5h， 生成 (3S)-6-acetyl-3-methyl-3,4-dihydrothieno[2,3-b]pyrazin-2(1H)-one
  参考文献：
  名称：

  Preparation of Thieno[2,3-b]pyrazines as Bioisosteres for Quinoxaline Derivatives wiht Reverse Transcriptase Inhibition

  摘要：

  Replacement of the fused aromatic moiety in GW-420867X, a HIV-1 specific nonnucleoside reverse transcriptase inhibitor, with thiophene provided 2-oxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine derivatives. The synthesis starts with the reaction of 5-acyl-2-chloro-3-nitrothiophene and different amino acid derivatives. The resulting substitution products are reduced, cyclized and N-acylated to give the desired compounds (27 - 33).

  DOI：

  10.3987/com-01-9371

文献信息

• Synthesis of Thieno[2,3-b]pyrazines via an Acylation - Deacylation Process of 3,4-Dihydro Precursors
  作者：Thomas Erker、Karin Trinkl、Franz Pertlik

  DOI：10.3987/com-02-9638

  日期：——

  In the first step 3, 4-dihydrothieno[2,3-h]pyrazines (1, 2 and 4) were N-acylated by the acyl chlorides followed by a deacylation process mediated by triethylamine to give thieno[2,3-b]pyrazines. In a final rection the excess of the appropriate acyl chlorides react with the free hydroxy residue to afford compounds (15, 16 or 17).

  在第一步 3 中，4-二氢噻吩并[2,3-h]吡嗪（1, 2 和 4）被酰氯 N-酰化，然后由三乙胺介导的脱酰过程得到噻吩并[2,3-b]吡嗪类。在最后一个反应中，过量的适当酰氯与游离羟基残基反应，得到化合物(15、16或17)。
• Preparation of Thieno[2,3-b]pyrazines as Bioisosteres for Quinoxaline Derivatives wiht Reverse Transcriptase Inhibition
  作者：Thomas Erker、Karin Trinkl

  DOI：10.3987/com-01-9371

  日期：——

  Replacement of the fused aromatic moiety in GW-420867X, a HIV-1 specific nonnucleoside reverse transcriptase inhibitor, with thiophene provided 2-oxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine derivatives. The synthesis starts with the reaction of 5-acyl-2-chloro-3-nitrothiophene and different amino acid derivatives. The resulting substitution products are reduced, cyclized and N-acylated to give the desired compounds (27 - 33).