(1S,2R,4R)-7-tosyl-7-azabicyclo[2.2.1]heptane-2-carboxylic acid | 1156453-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,4R)-7-tosyl-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
• 英文别名: (1S,2R,4R)-7-(4-methylphenyl)sulfonyl-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 1156453-14-3
• 化学式: C₁₄H₁₇NO₄S
• 分子量: 295.359
• InChiKey: HYCWQNSQLCBARO-RTXFEEFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R)-7-tosyl-7-azabicyclo[2.2.1]heptane-2-carboxylic acid 在 水 、 氢溴酸 、 苯酚 、 DOWEX 50WX₈-100 ion-exchange resin 、 氨 作用下， 以 水 为溶剂， 反应 5.0h， 以72%的产率得到(1S,2R,4R)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
  参考文献：
  名称：

  Constrained β-Proline Analogues in Organocatalytic Aldol Reactions: The Influence of Acid Geometry

  摘要：

  7-Azabicyclo[2.2.1]heptane-2-carboxylic acid 11 was prepared in enantiopure form, and its catalytic potential in the direct aldol reaction between acetone and 4-nitrobenzaldehyde was assessed. The bicyclic system was found to be more selective than its monocyclic analogue beta-proline 5b. A comparative density functional theory study of proline 1, beta-proline 5b, and 11 in the latter reaction revealed the origin of the improved enantioselectivity of 11 over 5b. The geometry of the carboxylic acid group in the transition states, which depended critically on pyrrolidine ring conformation, was found to play a key role.

  DOI：

  10.1021/jo900840v
• 作为产物：
  描述：

  (S)-4-isopropyl-3-((1S,2R,4R)-7-tosyl-7-azabicyclo[2.2.1]heptane-2-carbonyl)oxazolidin-2-one 在 lithium hydroxide monohydrate 、 水 、 双氧水 、 碳酸氢钠 、 sodium sulfite 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以71%的产率得到(1S,2R,4R)-7-tosyl-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
  参考文献：
  名称：

  Constrained β-Proline Analogues in Organocatalytic Aldol Reactions: The Influence of Acid Geometry

  摘要：

  7-Azabicyclo[2.2.1]heptane-2-carboxylic acid 11 was prepared in enantiopure form, and its catalytic potential in the direct aldol reaction between acetone and 4-nitrobenzaldehyde was assessed. The bicyclic system was found to be more selective than its monocyclic analogue beta-proline 5b. A comparative density functional theory study of proline 1, beta-proline 5b, and 11 in the latter reaction revealed the origin of the improved enantioselectivity of 11 over 5b. The geometry of the carboxylic acid group in the transition states, which depended critically on pyrrolidine ring conformation, was found to play a key role.

  DOI：

  10.1021/jo900840v

文献信息

• Constrained β-Proline Analogues in Organocatalytic Aldol Reactions: The Influence of Acid Geometry
  作者：Alan Armstrong、Yunas Bhonoah、Andrew J. P. White

  DOI：10.1021/jo900840v

  日期：2009.7.17

  7-Azabicyclo[2.2.1]heptane-2-carboxylic acid 11 was prepared in enantiopure form, and its catalytic potential in the direct aldol reaction between acetone and 4-nitrobenzaldehyde was assessed. The bicyclic system was found to be more selective than its monocyclic analogue beta-proline 5b. A comparative density functional theory study of proline 1, beta-proline 5b, and 11 in the latter reaction revealed the origin of the improved enantioselectivity of 11 over 5b. The geometry of the carboxylic acid group in the transition states, which depended critically on pyrrolidine ring conformation, was found to play a key role.