2(R),3(R),4(S) 2-isopropyl-3,4-(N-phenyl dicarboximido)pyrrolidine-2-carboxylic acid | 139406-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2(R),3(R),4(S) 2-isopropyl-3,4-(N-phenyl dicarboximido)pyrrolidine-2-carboxylic acid
• 英文别名: (3R,3aR,6aS)-4,6-dioxo-5-phenyl-3-propan-2-yl-1,2,3a,6a-tetrahydropyrrolo[3,4-c]pyrrole-3-carboxylic acid
• CAS: 139406-21-6
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: JLICTLOKOUEHNF-BFQNTYOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-phenyl 2(R),6(R),7(R),8(S) 6-isopropyl-2-phenyl-1-aza-4-oxa<4.3.0^1,6>bicyclononan-5-one-7,8-dicarboximide 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以74%的产率得到2(R),3(R),4(S) 2-isopropyl-3,4-(N-phenyl dicarboximido)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Development of chiral stabilised azomethine ylids: A chiral memory relay system.

  摘要：

  Chiral, stabilised azomethine ylids incorporated in cyclic templates derived from (R)- or (S)-2-phenylglycinol and (S)-valine undergo enantioselective 1,3-dipolar cycloaddition reactions with a variety of dipolarophiles. Removal of the template in the case of adducts derived originally from (S)-valine furnishes enantiomerically pure alpha-substituted proline derivatives.

  DOI：

  10.1016/s0957-4166(00)80031-2

文献信息

• Development of chiral stabilised azomethine ylids: A chiral memory relay system.
  作者：Amberley S. Anslow、Laurence M. Harwood、Helen Phillips、David Watkin、Ling F. Wong

  DOI：10.1016/s0957-4166(00)80031-2

  日期：1991.1

  Chiral, stabilised azomethine ylids incorporated in cyclic templates derived from (R)- or (S)-2-phenylglycinol and (S)-valine undergo enantioselective 1,3-dipolar cycloaddition reactions with a variety of dipolarophiles. Removal of the template in the case of adducts derived originally from (S)-valine furnishes enantiomerically pure alpha-substituted proline derivatives.
• Development of chiral stabilised azomethine ylids: completing the memory relay
  作者：Amberley S. Anslow、Laurence M. Harwood、Helen phillips、David Watkin

  DOI：10.1016/s0957-4166(00)86146-7

  日期：1991.1

  We report how the alpha-chirality of L-valine can be "memorised" through a sequence involving chirality transfer to a cyclic template, followed by azomethine ylid generation and enantiospecific cycloaddition to regenerate the centre lost during ylid formation. Subsequent removal of the chiral template furnishes alpha-substituted D-proline derivatives.