(1S,2S,4S,5R)-2-iodomethyl-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester | 286368-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1S,2S,4S,5R)-2-iodomethyl-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester
• 英文别名: methyl (3R,4S,6S)-6-(iodomethyl)-1-azabicyclo[2.2.2]octane-3-carboxylate
• CAS: 286368-20-5
• 化学式: C₁₀H₁₆INO₂
• 分子量: 309.147
• InChiKey: WSMAKWUJUGMMLY-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,4S,5R)-2-iodomethyl-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester 、 甲醇 在 silver benzoate 作用下， 反应 40.0h， 以75%的产率得到(1S,2R,5R,6R)-2-methoxy-1-azabicyclo[3.2.2]nonane-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Enantiopure 1-Azabicyclo[3.2.2]nonanes via Stereoselective Capture of Chiral Carbocations

  摘要：

  [GRAPHICS]A new class of doubly functionalized and enantiomerically pure 1-azabicyclo[3.2.2]nonanes derived from quincorine and quincoridine is described. 2,5-Disubstituted quinuclidines with a C9-mesyloxy group were easily transformed into the corresponding halides upon treatment with lithium salts. Subsequent silver salt-mediated ring expansion stereoselectively furnished the title azabicyclics. Chiral carbocations which are configurationally stable and nonplanar are postulated to account for the striking stereoselectivity of the capture of external nucleophile. 5-Ethynyl-2-iodomethylquinuclidines afford the alpha-benzoyloxy amines rather than alpha-methoxy amines, even in MeOH.

  DOI：

  10.1021/ol0057378
• 作为产物：
  描述：

  (1S,3R,4S,6S)-6-Methanesulfonyloxymethyl-1-aza-bicyclo[2.2.2]octane-3-carboxylic acid methyl ester 在 lithium iodide 作用下， 以 1,4-二氧六环 为溶剂， 以81%的产率得到(1S,2S,4S,5R)-2-iodomethyl-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Enantiopure 1-Azabicyclo[3.2.2]nonanes via Stereoselective Capture of Chiral Carbocations

  摘要：

  [GRAPHICS]A new class of doubly functionalized and enantiomerically pure 1-azabicyclo[3.2.2]nonanes derived from quincorine and quincoridine is described. 2,5-Disubstituted quinuclidines with a C9-mesyloxy group were easily transformed into the corresponding halides upon treatment with lithium salts. Subsequent silver salt-mediated ring expansion stereoselectively furnished the title azabicyclics. Chiral carbocations which are configurationally stable and nonplanar are postulated to account for the striking stereoselectivity of the capture of external nucleophile. 5-Ethynyl-2-iodomethylquinuclidines afford the alpha-benzoyloxy amines rather than alpha-methoxy amines, even in MeOH.

  DOI：

  10.1021/ol0057378