(8S)-1,1-dioxo-2,3,5a,6,7,8-hexahydro-1H-1λ⁶-pyrrolo[1,2-b][1,2]thiazepine-8-carboxylic acid benzyl ester | 608128-59-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (8S)-1,1-dioxo-2,3,5a,6,7,8-hexahydro-1H-1λ⁶-pyrrolo[1,2-b][1,2]thiazepine-8-carboxylic acid benzyl ester
• 英文别名: benzyl (5aS,8S)-1,1-dioxo-2,3,5a,6,7,8-hexahydropyrrolo[1,2-b]thiazepine-8-carboxylate
• CAS: 608128-59-2
• 化学式: C₁₆H₁₉NO₄S
• 分子量: 321.397
• InChiKey: BLLFEXCAPLPDPY-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (8S)-1,1-dioxo-2,3,5a,6,7,8-hexahydro-1H-1λ⁶-pyrrolo[1,2-b][1,2]thiazepine-8-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以86%的产率得到(8S)-1,1-dioxo-octahydro-1λ⁶-pyrrolo[1,2-b][1,2]thiazepine-8-carboxylic acid
  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)-((Z)-5-Propenyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester 在 Grubbs catalyst first generation 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (8S)-1,1-dioxo-2,3,5a,6,7,8-hexahydro-1H-1λ⁶-pyrrolo[1,2-b][1,2]thiazepine-8-carboxylic acid benzyl ester
  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