(1S,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-benzyl ester | 700867-05-6

• 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,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-benzyl ester
• 英文别名: (1S,3R,4R)-2-phenylmethoxycarbonyl-2-azabicyclo[2.2.1]heptane-3-carboxylic acid
• CAS: 700867-05-6
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: HBYDEUGDUPDHMT-FRRDWIJNSA-N

物化性质

• 沸点：
  461.6±38.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-benzyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 甲基磺酰氯 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 (1S,3R,4R)-3-(4',5'-dihydro-5'(R)-isopropyl-1',3'-oxazol-2'-yl)-2-aza-bicyclo-[2.2.1]-heptane
  参考文献：
  名称：

  Development of a new class of (1S,3R,4R)-2-azabicyclo[2.2.1]heptane-oxazoline ligands and their application in asymmetric transfer hydrogenation

  摘要：

  New 2-aza-norbomane-oxazoline compounds were synthesized and evaluated as ligands in the transfer hydrogenation of acetophenone. The best catalyst prepared in situ from [IrCl2(COD)](2) and a ligand afforded 1-(S)-phenylethanol in good yields and 79% ee. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.01.102
• 作为产物：
  描述：

  氯甲酸苄酯 、 (1S,3R,4R)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 3.0h， 生成 (1S,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-benzyl ester
  参考文献：
  名称：

  Development of a new class of (1S,3R,4R)-2-azabicyclo[2.2.1]heptane-oxazoline ligands and their application in asymmetric transfer hydrogenation

  摘要：

  New 2-aza-norbomane-oxazoline compounds were synthesized and evaluated as ligands in the transfer hydrogenation of acetophenone. The best catalyst prepared in situ from [IrCl2(COD)](2) and a ligand afforded 1-(S)-phenylethanol in good yields and 79% ee. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.01.102

文献信息

• Development of a new class of (1S,3R,4R)-2-azabicyclo[2.2.1]heptane-oxazoline ligands and their application in asymmetric transfer hydrogenation
  作者：Anna Trifonova、Klas E Källström、Pher G Andersson

  DOI：10.1016/j.tet.2004.01.102

  日期：2004.4

  New 2-aza-norbomane-oxazoline compounds were synthesized and evaluated as ligands in the transfer hydrogenation of acetophenone. The best catalyst prepared in situ from [IrCl2(COD)](2) and a ligand afforded 1-(S)-phenylethanol in good yields and 79% ee. (C) 2004 Published by Elsevier Ltd.