2,2-dimethylpropionic acid 1S-8,8-dioxo-8λ⁶-thia-9-azatricyclo[7.2.1.0^2,7]dodeca-2,4,6-trien-10R-yl methyl ester | 929556-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2,2-dimethylpropionic acid 1S-8,8-dioxo-8λ⁶-thia-9-azatricyclo[7.2.1.0^2,7]dodeca-2,4,6-trien-10R-yl methyl ester
• 英文别名: [(1S,10R)-8,8-dioxo-8lambda6-thia-9-azatricyclo[7.2.1.02,7]dodeca-2,4,6-trien-10-yl]methyl 2,2-dimethylpropanoate；[(1S,10R)-8,8-dioxo-8λ6-thia-9-azatricyclo[7.2.1.02,7]dodeca-2,4,6-trien-10-yl]methyl 2,2-dimethylpropanoate
• CAS: 929556-10-5
• 化学式: C₁₆H₂₁NO₄S
• 分子量: 323.413
• InChiKey: PRYRYROSYPQTRZ-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpropionic acid 1S-8,8-dioxo-8λ⁶-thia-9-azatricyclo[7.2.1.0^2,7]dodeca-2,4,6-trien-10R-yl methyl ester 在 氨 、 lithium 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 [4S-phenyl-1-(toluene-4-sulfonyl)pyrrolidin-2R-yl]methanol
  参考文献：
  名称：

  The Double Reduction of Cyclic Sulfonamides for the Synthesis of (4S-Phenylpyrrolidin-2R-yl)methanol and 2S-Methyl-4S-phenylpyrrolidine

  摘要：

  The synthesis of (4S-phenylpyrrolidin-2R-yl)methanol and 2S-methyl-4S-phenylpyrrolidine has been achieved via the double reduction of their cyclic sulfonamide precursors which themselves were prepared following the stereoselective intramolecular Heck reaction of a chiral pool derived 2,5-dihydropyrrole. We have recently described a process whereby cyclic aryl sulfonamides, such as 2, are reductively ring-opened to furnish amino products in which the aryl group is incorporated in the final compound. (Evans, P.; McCabe, T.; Morgan, B. S.; Reau, S. Org. Lett. 2005, 7, 43.) The precursors for this reaction were assembled using an intramolecular Heck reaction followed by reduction of the alkene. Overall, this sequence represents an efficient means to construct molecules of this type in which the aryl sulfonyl moiety acts as both an N-protecting group and as an aryl donor. Use of Benkeser's stronger reducing conditions enables molecules such as 4 to be prepared in which both the sulfonamide functional group and the aromaticity of the aryl substituent have been destroyed.

  DOI：

  10.1021/jo062189o
• 作为产物：
  描述：

  1-(2-bromobenzenesulfonyl)-2,5-dihydro-1H-pyrrole-2S-carboxylic acid ethyl ester 在 palladium diacetate 、 palladium on activated charcoal 氢气 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -78.0~60.0 ℃ 、101.33 kPa 条件下， 反应 46.0h， 生成 2,2-dimethylpropionic acid 1S-8,8-dioxo-8λ⁶-thia-9-azatricyclo[7.2.1.0^2,7]dodeca-2,4,6-trien-10R-yl methyl ester
  参考文献：
  名称：

  The Double Reduction of Cyclic Sulfonamides for the Synthesis of (4S-Phenylpyrrolidin-2R-yl)methanol and 2S-Methyl-4S-phenylpyrrolidine

  摘要：

  The synthesis of (4S-phenylpyrrolidin-2R-yl)methanol and 2S-methyl-4S-phenylpyrrolidine has been achieved via the double reduction of their cyclic sulfonamide precursors which themselves were prepared following the stereoselective intramolecular Heck reaction of a chiral pool derived 2,5-dihydropyrrole. We have recently described a process whereby cyclic aryl sulfonamides, such as 2, are reductively ring-opened to furnish amino products in which the aryl group is incorporated in the final compound. (Evans, P.; McCabe, T.; Morgan, B. S.; Reau, S. Org. Lett. 2005, 7, 43.) The precursors for this reaction were assembled using an intramolecular Heck reaction followed by reduction of the alkene. Overall, this sequence represents an efficient means to construct molecules of this type in which the aryl sulfonyl moiety acts as both an N-protecting group and as an aryl donor. Use of Benkeser's stronger reducing conditions enables molecules such as 4 to be prepared in which both the sulfonamide functional group and the aromaticity of the aryl substituent have been destroyed.

  DOI：

  10.1021/jo062189o

文献信息

• The Double Reduction of Cyclic Sulfonamides for the Synthesis of (4<i>S</i>-Phenylpyrrolidin-2<i>R</i>-yl)methanol and 2<i>S</i>-Methyl-4<i>S</i>-phenylpyrrolidine
  作者：Paul Evans

  DOI：10.1021/jo062189o

  日期：2007.3.1

  The synthesis of (4S-phenylpyrrolidin-2R-yl)methanol and 2S-methyl-4S-phenylpyrrolidine has been achieved via the double reduction of their cyclic sulfonamide precursors which themselves were prepared following the stereoselective intramolecular Heck reaction of a chiral pool derived 2,5-dihydropyrrole. We have recently described a process whereby cyclic aryl sulfonamides, such as 2, are reductively ring-opened to furnish amino products in which the aryl group is incorporated in the final compound. (Evans, P.; McCabe, T.; Morgan, B. S.; Reau, S. Org. Lett. 2005, 7, 43.) The precursors for this reaction were assembled using an intramolecular Heck reaction followed by reduction of the alkene. Overall, this sequence represents an efficient means to construct molecules of this type in which the aryl sulfonyl moiety acts as both an N-protecting group and as an aryl donor. Use of Benkeser's stronger reducing conditions enables molecules such as 4 to be prepared in which both the sulfonamide functional group and the aromaticity of the aryl substituent have been destroyed.