N-[(1R,2R)-2-[[4-(dimethylamino)pyridin-2-yl]amino]cyclohexyl]-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide | 1421748-73-3

• 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: N-[(1R,2R)-2-[[4-(dimethylamino)pyridin-2-yl]amino]cyclohexyl]-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
• CAS: 1421748-73-3
• 化学式: C₂₃H₃₆N₄O₃S
• 分子量: 448.63
• InChiKey: MBQSXXWGMDTBFE-DYVMYPEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(1R,2R)-2-[[4-(dimethylamino)pyridin-2-yl]amino]cyclohexyl]-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以85%的产率得到N-[(1R,2R)-2-[[4-(dimethylamino)pyridin-2-yl]amino]cyclohexyl]-1-[(1S,2R,4R)-2-hydroxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
  参考文献：
  名称：

  Cu-Catalyzed Selective Mono-N-pyridylation: Direct Access to 2-AminoDMAP/Sulfonamides as Bifunctional Organocatalysts

  摘要：

  Direct and selective mono-N-pyridylation of trans-(R,R)-cyclohexane-1,2-diamine is described here. Facile preparation of a novel chiral 2-aminoDMAP core catalaphore via Cu catalysis has led to the development of various sulfonamide/2-aminoDMAPs as bifunctional acid/base organocatalysts (most in two steps overall), which have been shown to very effectively promote asymmetric conjugate addition of acetylacetone to trans-beta-nitroolefins with good to excellent yields (87-93%) and enantioselectivites (up to 99%).

  DOI：

  10.1021/jo302713b
• 作为产物：
  描述：

  2-((1R,2R)-2-aminocyclohexyl)isoindoline-1,3-dione 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 氘代甲苯 为溶剂， 反应 63.0h， 生成 N-[(1R,2R)-2-[[4-(dimethylamino)pyridin-2-yl]amino]cyclohexyl]-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
  参考文献：
  名称：

  Cu-Catalyzed Selective Mono-N-pyridylation: Direct Access to 2-AminoDMAP/Sulfonamides as Bifunctional Organocatalysts

  摘要：

  Direct and selective mono-N-pyridylation of trans-(R,R)-cyclohexane-1,2-diamine is described here. Facile preparation of a novel chiral 2-aminoDMAP core catalaphore via Cu catalysis has led to the development of various sulfonamide/2-aminoDMAPs as bifunctional acid/base organocatalysts (most in two steps overall), which have been shown to very effectively promote asymmetric conjugate addition of acetylacetone to trans-beta-nitroolefins with good to excellent yields (87-93%) and enantioselectivites (up to 99%).

  DOI：

  10.1021/jo302713b

文献信息

• Cu-Catalyzed Selective Mono-<i>N</i>-pyridylation: Direct Access to 2-AminoDMAP/Sulfonamides as Bifunctional Organocatalysts
  作者：Murat Isik、Cihangir Tanyeli

  DOI：10.1021/jo302713b

  日期：2013.2.15

  Direct and selective mono-N-pyridylation of trans-(R,R)-cyclohexane-1,2-diamine is described here. Facile preparation of a novel chiral 2-aminoDMAP core catalaphore via Cu catalysis has led to the development of various sulfonamide/2-aminoDMAPs as bifunctional acid/base organocatalysts (most in two steps overall), which have been shown to very effectively promote asymmetric conjugate addition of acetylacetone to trans-beta-nitroolefins with good to excellent yields (87-93%) and enantioselectivites (up to 99%).