C-((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-N-{(4S,5S)-5-[((1S,4R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonylamino)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-methanesulfonamide | 910541-43-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: C-((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-N-{(4S,5S)-5-[((1S,4R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonylamino)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-methanesulfonamide
• CAS: 910541-43-4
• 化学式: C₂₇H₄₄N₂O₈S₂
• 分子量: 588.787
• InChiKey: LRPQCESVCADKGO-XCUHCJQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  144.94
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  C-((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-N-{(4S,5S)-5-[((1S,4R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonylamino)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-methanesulfonamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以40%的产率得到1-[(1S,2R,4R)-2-hydroxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]-N-[[(4S,5S)-5-[[[(1S,2R,4R)-2-hydroxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]methylsulfonylamino]methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]methanesulfonamide
  参考文献：
  名称：

  A new chiral sulfonamide ligand based on tartaric acid: synthesis and application in the enantioselective addition of diethylzinc to aldehydes and ketones

  摘要：

  A new sulfonamide ligand based on L-tartaric acid was synthesized and was employed as a chiral ligand in the enantioselective addition of diethylzinc to aldehydes, giving rise to the best enantiomeric excess up to 83% with 5 mol % of catalyst loading. Moreover, the addition of diethylzinc to ketones can also be achieved with good to excellent enantioselectivities by employing 7 mol % of the catalyst under mild conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.040
• 作为产物：
  描述：

  (4R,5R)-N⁴,N⁴,N⁵,N⁵,2,2-hexamethyl-1,3-dioxolane-4,5-dicarboxamide 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 C-((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-N-{(4S,5S)-5-[((1S,4R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonylamino)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-methanesulfonamide
  参考文献：
  名称：

  A new chiral sulfonamide ligand based on tartaric acid: synthesis and application in the enantioselective addition of diethylzinc to aldehydes and ketones

  摘要：

  A new sulfonamide ligand based on L-tartaric acid was synthesized and was employed as a chiral ligand in the enantioselective addition of diethylzinc to aldehydes, giving rise to the best enantiomeric excess up to 83% with 5 mol % of catalyst loading. Moreover, the addition of diethylzinc to ketones can also be achieved with good to excellent enantioselectivities by employing 7 mol % of the catalyst under mild conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.040