N-((R)-7,7-Dioxo-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-4-yl)-acetamide | 147086-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-((R)-7,7-Dioxo-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-4-yl)-acetamide
• CAS: 147086-86-0
• 化学式: C₉H₁₁NO₃S₂
• 分子量: 245.323
• InChiKey: DPXZOBBUXGGUFW-MRVPVSSYSA-N

物化性质

• 沸点：
  544.5±50.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.24
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-((R)-7,7-Dioxo-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-4-yl)-acetamide 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 生成 5,6-dihydro-4-(ethylamino)-4H-thieno<2,3-b>thiopyran 7,7-dioxide
  参考文献：
  名称：

  An enantioselective synthesis of the topically-active carbonic anhydrase inhibitor MK-0507: 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride

  摘要：

  The key feature in the synthesis of topically-active carbonic anhydrase inhibitor MK-0507 (13b) is a Ritter reaction that exhibits an unexpected tendency to proceed with retention of chirality. This phenomenon was further studied on model compounds free from potential diastereomeric effects. A mechanism involving transannular stabilization of the sp2-hybridized center by sulfone oxygen is proposed with the net result of double inversion. A second key feature in the preferred sequence to MK-0507 involves the classic problem of how to maximize substitution over elimination. This problem manifests itself in the stereospecific alkylation of 2-mercaptothiophene with derivatized methyl (R)-3-hydroxybutyrate and is compounded by a subsequent Michael reaction leading to a loss of product chirality. Results are presented that eliminate this problem.

  DOI：

  10.1021/jo00059a013
• 作为产物：
  描述：

  (R)-(+)-5,6-Dihydro-4H-thieno<2,3-b>thiopyran-4-ol 7,7-Dioxide 、 乙腈 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-((R)-7,7-Dioxo-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-4-yl)-acetamide
  参考文献：
  名称：

  An enantioselective synthesis of the topically-active carbonic anhydrase inhibitor MK-0507: 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride

  摘要：

  The key feature in the synthesis of topically-active carbonic anhydrase inhibitor MK-0507 (13b) is a Ritter reaction that exhibits an unexpected tendency to proceed with retention of chirality. This phenomenon was further studied on model compounds free from potential diastereomeric effects. A mechanism involving transannular stabilization of the sp2-hybridized center by sulfone oxygen is proposed with the net result of double inversion. A second key feature in the preferred sequence to MK-0507 involves the classic problem of how to maximize substitution over elimination. This problem manifests itself in the stereospecific alkylation of 2-mercaptothiophene with derivatized methyl (R)-3-hydroxybutyrate and is compounded by a subsequent Michael reaction leading to a loss of product chirality. Results are presented that eliminate this problem.

  DOI：

  10.1021/jo00059a013