(2S,4R)-di-tert-butyl 4-{[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methylsulfonyloxy}pyrrolidine-1,2-dicarboxylate | 865303-08-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2S,4R)-di-tert-butyl 4-{[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methylsulfonyloxy}pyrrolidine-1,2-dicarboxylate
• 英文别名: ditert-butyl (2S,4R)-4-[[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methylsulfonyloxy]pyrrolidine-1,2-dicarboxylate
• CAS: 865303-08-8
• 化学式: C₂₄H₃₉NO₈S
• 分子量: 501.642
• InChiKey: YUOAXQXWINIPTK-MJZOOFNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4R)-di-tert-butyl 4-{[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methylsulfonyloxy}pyrrolidine-1,2-dicarboxylate 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以95%的产率得到(2S,4R)-4-{[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methylsulfonyloxy}pyrrolidine-2-carboxylic acid hydrochloride
  参考文献：
  名称：

  4-Substituted prolines as organocatalysts for aldol reactions

  摘要：

  A series of 4-substituted prolines were prepared and evaluated as organocatalysts for asymmetric aldol reactions. Using (2S,4R)4-camphorsulfonyloxy-proline, the aldol products were obtained in much higher enantiomeric excess in comparison to that observed using proline itself. In addition, the improved solubility of these new catalysts in organic solvents permits their use in lower sub-stoichiometric amounts compared to proline. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.113
• 作为产物：
  描述：

  N-叔丁氧羰基-O-苄基-反式-4-羟基-L-脯氨酸 在 palladium on activated charcoal N-甲基吗啉 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 环己烷 为溶剂， 反应 72.5h， 生成 (2S,4R)-di-tert-butyl 4-{[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methylsulfonyloxy}pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  4-Substituted prolines as organocatalysts for aldol reactions

  摘要：

  A series of 4-substituted prolines were prepared and evaluated as organocatalysts for asymmetric aldol reactions. Using (2S,4R)4-camphorsulfonyloxy-proline, the aldol products were obtained in much higher enantiomeric excess in comparison to that observed using proline itself. In addition, the improved solubility of these new catalysts in organic solvents permits their use in lower sub-stoichiometric amounts compared to proline. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.113