(6S)-6-(tert-butyl-diphenylsilanyloxymethyl)-3a,4,5,6-tetrahydro-pyrrolo[1,2-b]isothiazole 1,1-dioxide | 608128-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (6S)-6-(tert-butyl-diphenylsilanyloxymethyl)-3a,4,5,6-tetrahydro-pyrrolo[1,2-b]isothiazole 1,1-dioxide
• 英文别名: [(3aS,6S)-1,1-dioxo-3a,4,5,6-tetrahydropyrrolo[1,2-b][1,2]thiazol-6-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 608128-51-4
• 化学式: C₂₃H₂₉NO₃SSi
• 分子量: 427.64
• InChiKey: SEQBTWVXGHQVRV-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6S)-6-(tert-butyl-diphenylsilanyloxymethyl)-3a,4,5,6-tetrahydro-pyrrolo[1,2-b]isothiazole 1,1-dioxide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以57%的产率得到(6S)-(1,1-dioxo-3a,4,5,6-tetrahydro-1H-1λ⁶-pyrrolo[1,2-b]isothiazol-6-yl)methanol
  参考文献：
  名称：

  Synthesis of functionally diverse bicyclic sulfonamides as constrained proline analogues and application to the design of potential thrombin inhibitors

  摘要：

  Bicyclic sulfonamides were synthesized from 4-alkenyl N-alkenylsulfonyl L-prolines using a ring-closure metathesis reaction. Three types of bicyclic sulfonamides varying in the size of the second ring (5,5; 5,6; 5,7) were synthesized. A sulfonamide counterpart of an indolizidinone 2-carboxylic acid was synthesized and evaluated for its activity against the enzyme thrombin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00919-0
• 作为产物：
  描述：

  (2S,5S)-2-(tert-butyl-diphenylsilanyloxymethyl)-5-cis-propenyl-pyrrolidine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 64.5h， 生成 (6S)-6-(tert-butyl-diphenylsilanyloxymethyl)-3a,4,5,6-tetrahydro-pyrrolo[1,2-b]isothiazole 1,1-dioxide
  参考文献：
  名称：

  Synthesis of functionally diverse bicyclic sulfonamides as constrained proline analogues and application to the design of potential thrombin inhibitors

  摘要：

  Bicyclic sulfonamides were synthesized from 4-alkenyl N-alkenylsulfonyl L-prolines using a ring-closure metathesis reaction. Three types of bicyclic sulfonamides varying in the size of the second ring (5,5; 5,6; 5,7) were synthesized. A sulfonamide counterpart of an indolizidinone 2-carboxylic acid was synthesized and evaluated for its activity against the enzyme thrombin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00919-0