(3S)-6-benzoyl-3-methyl-3,4-dihydrothieno[2,3-b]pyrazin-2(1H)-one | 433212-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-6-benzoyl-3-methyl-3,4-dihydrothieno[2,3-b]pyrazin-2(1H)-one
• CAS: 433212-95-4
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: HEPWFSYXWYARTN-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  氯甲酸乙烯酯 、 (3S)-6-benzoyl-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72%的产率得到(3S)-vinyl 6-benzoyl-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：

  (5-Chlor-4-nitro-2-thienyl)-phenylmethanon 在 铁粉 、 potassium carbonate 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 7.5h， 生成 (3S)-6-benzoyl-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

• 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).