N-(5,6-dihydro-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-(R)-4-yl)acetamide 7,7-dioxide | 148810-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: N-(5,6-dihydro-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-(R)-4-yl)acetamide 7,7-dioxide
• 英文别名: N-((4R,6S)-6-Methyl-7,7-dioxido-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl)acetamide；N-[(4R,6S)-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl]acetamide
• CAS: 148810-83-7
• 化学式: C₁₀H₁₃NO₃S₂
• 分子量: 259.35
• InChiKey: WJXLCNFSFHSWMJ-IMTBSYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,6-dihydro-(R,S)-4-acetoxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide 、 乙腈 在 硫酸 作用下， 生成 N-(5,6-dihydro-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-(R)-4-yl)acetamide 7,7-dioxide 、 N-[(4S,6S)-5,6-二氢-6-甲基-4H-噻吩并[2,3-b]噻喃-4-基]乙酰胺-7,7-二氧化物
  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

文献信息

• 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
  作者：Thomas J. Blacklock、Paul Sohar、John W. Butcher、T. Lamanec、E. J. J. Grabowski

  DOI：10.1021/jo00059a013

  日期：1993.3

  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.