6-methyl-2,3,3a,6,7,7a-hexahydrobenzo[d]isothiazole-1,1-dioxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 6-methyl-2,3,3a,6,7,7a-hexahydrobenzo[d]isothiazole-1,1-dioxide
• 英文别名: (3aR,6S,7aR)-6-methyl-2,3,3a,6,7,7a-hexahydro-1,2-benzothiazole 1,1-dioxide
• 化学式: C₈H₁₃NO₂S
• 分子量: 187.263
• InChiKey: LCGSQYFJUJYIMQ-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-2,3,3a,6,7,7a-hexahydrobenzo[d]isothiazole-1,1-dioxide 、 溴代异丁烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以36%的产率得到2-isobutyl-6-methyl-2,3,3a,6,7,7a-hexahydrobenzo[d]isothiazole-1,1-dioxide
  参考文献：
  名称：

  Studies concerning the double reduction of Diels–Alder derived bicylic sulfonamides

  摘要：

  A series of bicyclic sulfonamides, 14-17, was prepared by thermal, intramolecular Diels-Alder cycloaddition. The ratio of exo:endo-diastereoisomers formed following this process was found to be dependent on the substitution pattern of the dienophile. Styryl substituted sulfonamides preferentially formed the corresponding exo-adducts, whereas vinyl substituted sulfonamides preferentially gave the endo-adducts. These adducts were treated under dissolved metal reduction conditions and it was found that compounds possessing an N-benzyl substituent underwent preferential debenzylation and resisted further reduction. The complementary N-isobutyl functionalised materials only underwent the double reduction when a phenyl substituent was present. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.015
• 作为产物：
  描述：

  2-benzyl-6-methyl-2,3,3a,6,7,7a-hexahydrobenzo[d]isothiazole-1,1-dioxide 在 氨 、 lithium 、 氯化铵 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 1.0h， 以65%的产率得到6-methyl-2,3,3a,6,7,7a-hexahydrobenzo[d]isothiazole-1,1-dioxide
  参考文献：
  名称：

  Studies concerning the double reduction of Diels–Alder derived bicylic sulfonamides

  摘要：

  A series of bicyclic sulfonamides, 14-17, was prepared by thermal, intramolecular Diels-Alder cycloaddition. The ratio of exo:endo-diastereoisomers formed following this process was found to be dependent on the substitution pattern of the dienophile. Styryl substituted sulfonamides preferentially formed the corresponding exo-adducts, whereas vinyl substituted sulfonamides preferentially gave the endo-adducts. These adducts were treated under dissolved metal reduction conditions and it was found that compounds possessing an N-benzyl substituent underwent preferential debenzylation and resisted further reduction. The complementary N-isobutyl functionalised materials only underwent the double reduction when a phenyl substituent was present. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.015