(+)-3-<(S)-2-methylbutyl>-1,2-benzisothiazole 1,1-dioxide | 131759-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (+)-3-<(S)-2-methylbutyl>-1,2-benzisothiazole 1,1-dioxide
• 英文别名: 3-[(2S)-2-methylbutyl]-1,2-benzothiazole 1,1-dioxide
• CAS: 131759-31-4
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: IWBDQKIRKFMMPC-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-3-<(S)-2-methylbutyl>-1,2-benzisothiazole 1,1-dioxide 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以34%的产率得到(+)-(2R,3S)-3-<(S)-2-methylbutyl>-1,2-benzisothiazole 1,1-dioxide oxide
  参考文献：
  名称：

  Chemistry of oxaziridines. 15. Asymmetric oxidations using 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides

  摘要：

  The synthesis and asymmetric oxidations of chiral nonracemic 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides (6) are described. These new N-sulfonyloxaziridines are prepared by oxidation of the corresponding enantiomerically pure sulfonimines 5. These reagents oxidize sulfides to sulfoxides (11-52% ee), epoxidize nonfunctionalized alkenes (17-61% ee), and oxidize enolates to alpha-hydroxy carbonyl compounds (11-81% ee). Epoxidation of (-)-(S)-limonene with (+)-(2R,3S)-6a, a double asymmetric synthesis, affords a 93:7 cis/trans mixture of limonene oxides. Evaluation of possible transition-state structures suggests that the molecular recognition is primarily determined by steric factors. These reagents are less effective than N-sulfonyloxaziridines 1-3 in their asymmetric oxidations because they lack well-defined regions that are topologically dissimilar near the active site.

  DOI：

  10.1021/jo00002a056
• 作为产物：
  描述：

  3-乙氧基-1,2-苯并噻唑1,1-二氧化物 、 (S)-(+)-1-氯-2-甲基丁烷 在 lithium 作用下， 生成 (+)-3-<(S)-2-methylbutyl>-1,2-benzisothiazole 1,1-dioxide
  参考文献：
  名称：

  Chemistry of oxaziridines. 15. Asymmetric oxidations using 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides

  摘要：

  The synthesis and asymmetric oxidations of chiral nonracemic 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides (6) are described. These new N-sulfonyloxaziridines are prepared by oxidation of the corresponding enantiomerically pure sulfonimines 5. These reagents oxidize sulfides to sulfoxides (11-52% ee), epoxidize nonfunctionalized alkenes (17-61% ee), and oxidize enolates to alpha-hydroxy carbonyl compounds (11-81% ee). Epoxidation of (-)-(S)-limonene with (+)-(2R,3S)-6a, a double asymmetric synthesis, affords a 93:7 cis/trans mixture of limonene oxides. Evaluation of possible transition-state structures suggests that the molecular recognition is primarily determined by steric factors. These reagents are less effective than N-sulfonyloxaziridines 1-3 in their asymmetric oxidations because they lack well-defined regions that are topologically dissimilar near the active site.

  DOI：

  10.1021/jo00002a056

文献信息

• DAVIS, FRANKLIN;REDDY, R. THIMMA;MCCAULEY, JOHN P. (JR);PRZESLAWSKI, ROBE+, J. ORG. CHEM., 56,(1991) N, C. 809-815
  作者：DAVIS, FRANKLIN、REDDY, R. THIMMA、MCCAULEY, JOHN P. (JR)、PRZESLAWSKI, ROBE+

  DOI：——

  日期：——