(1S,3R,5aS,7aS,7bR)-octahydro-1-hydroxy-7b-methyl-3-(1-naphthylmethyl)cyclopenta[gh]pyrrolizinium bromide | 1304686-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,3R,5aS,7aS,7bR)-octahydro-1-hydroxy-7b-methyl-3-(1-naphthylmethyl)cyclopenta[gh]pyrrolizinium bromide
• 英文别名: (1R,3S,4S,7S,10R)-10-methyl-1-(naphthalen-1-ylmethyl)-1-azoniatricyclo[5.2.1.04,10]decan-3-ol;bromide
• CAS: 1304686-06-3
• 化学式: Br*C₂₁H₂₆NO
• 分子量: 388.348
• InChiKey: CASFEJJFGUVXJP-KIIOHFOZSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  rel-(1R,3S,5aR,7aR,7bS)-1-hydroxy-7b-methyl-2-oxo-5a,6,7,7a-tetrahydrocyclopenta<1,2,3-gi>pyrrolidino<1,2-a>pyrrolidine 在 盐酸 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 26.16h， 生成 (1S,3R,5aS,7aS,7bR)-octahydro-1-hydroxy-7b-methyl-3-(1-naphthylmethyl)cyclopenta[gh]pyrrolizinium bromide
  参考文献：
  名称：

  A Systematic Investigation of Quaternary Ammonium Ions as Asymmetric Phase-Transfer Catalysts. Synthesis of Catalyst Libraries and Evaluation of Catalyst Activity

  摘要：

  Despite over three decades of research into asymmetric phase-transfer catalysis (APTC), a fundamental understanding of the factors that affect the rate and stereoselectivity of this important process are still obscure. This paper describes the initial stages of a long-term program aimed at elucidating the physical organic foundations of APTC employing a chemoinformatic analysis of the alkylation of a protected glycine imine with libraries of enantiomerically enriched quaternary ammonium ions. The synthesis of the quaternary ammonium ions follows a diversity:oriented approach wherein the tandem inter [4 + 2]/intra[3 + 2] cycloaddition of nitroalkenes serves as the key transformation. A two-part synthetic strategy comprised of (1) preparation of enantioenriched scaffolds and (2) development of parallel synthesis procedures is described. The strategy allows for the facile introduction of four variable groups in the vicinity of a stereogenic quaternary ammonium ion. The quaternary ammonium ions exhibited a wide range of activity and to a lesser degree enantioselectivity. Catalyst activity and selectivity are rationalized in a qualitative way on the basis of the effective positive potential of the ammonium ion.

  DOI：

  10.1021/jo2005445

文献信息

• A Systematic Investigation of Quaternary Ammonium Ions as Asymmetric Phase-Transfer Catalysts. Synthesis of Catalyst Libraries and Evaluation of Catalyst Activity
  作者：Scott E. Denmark、Nathan D. Gould、Larry M. Wolf

  DOI：10.1021/jo2005445

  日期：2011.6.3

  Despite over three decades of research into asymmetric phase-transfer catalysis (APTC), a fundamental understanding of the factors that affect the rate and stereoselectivity of this important process are still obscure. This paper describes the initial stages of a long-term program aimed at elucidating the physical organic foundations of APTC employing a chemoinformatic analysis of the alkylation of a protected glycine imine with libraries of enantiomerically enriched quaternary ammonium ions. The synthesis of the quaternary ammonium ions follows a diversity:oriented approach wherein the tandem inter [4 + 2]/intra[3 + 2] cycloaddition of nitroalkenes serves as the key transformation. A two-part synthetic strategy comprised of (1) preparation of enantioenriched scaffolds and (2) development of parallel synthesis procedures is described. The strategy allows for the facile introduction of four variable groups in the vicinity of a stereogenic quaternary ammonium ion. The quaternary ammonium ions exhibited a wide range of activity and to a lesser degree enantioselectivity. Catalyst activity and selectivity are rationalized in a qualitative way on the basis of the effective positive potential of the ammonium ion.