(2S,3R,4S,5S)-methyl 3-(4-(2-hydroxyethoxy)phenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate | 1223020-46-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R,4S,5S)-methyl 3-(4-(2-hydroxyethoxy)phenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate
• 英文别名: methyl (2S,3R,4S,5S)-3-[4-(2-hydroxyethoxy)phenyl]-4-nitro-5-phenylpyrrolidine-2-carboxylate
• CAS: 1223020-46-9
• 化学式: C₂₀H₂₂N₂O₆
• 分子量: 386.404
• InChiKey: DDSVZHVYSUIKKH-XWSJACJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(苯基甲亚基)氨基]乙酸甲酯 、 2-<4-<(E)-2-nitroethenyl>phenyloxy>ethan-1-ol 在 2,6-双[(2R,4S,5S)-1-苄基-4,5-二苯基咪唑烷-2-基]吡啶 、 copper(II) bis(trifluoromethanesulfonate) 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 (2S,3R,4S,5S)-methyl 3-(4-(2-hydroxyethoxy)phenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate 、 (2R,3S,4R,5R)-methyl 3-(4-(2-hydroxyethoxy)phenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Chiral Bis(imidazolidine)pyridine−Cu(OTf)₂: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes

  摘要：

  The novel C-2-symmetric bis(imidazolidine)pyridine (PyBidine) ligand was easily synthesized in a single condensation of 2,6-pyridyl aldehyde and optically active (S,S)diphenylethylenediamine. In the C-2-symmetric PyBidine-Cu(OTf)(2) complex, imidazolidine rings act as "chiral fences" to shield the first and third quadrants. Use of the PyBidine-Cu(OTf)(2) complex as a catalyst enabled the highly endo-selective reaction of imino esters and nitroalkenes to give the adducts in up to 99% ee.

  DOI：

  10.1021/ja100265j

文献信息

• Chiral Bis(imidazolidine)pyridine−Cu(OTf)₂: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes
  作者：Takayoshi Arai、Asami Mishiro、Naota Yokoyama、Kuniko Suzuki、Hiroyasu Sato

  DOI：10.1021/ja100265j

  日期：2010.4.21

  The novel C-2-symmetric bis(imidazolidine)pyridine (PyBidine) ligand was easily synthesized in a single condensation of 2,6-pyridyl aldehyde and optically active (S,S)diphenylethylenediamine. In the C-2-symmetric PyBidine-Cu(OTf)(2) complex, imidazolidine rings act as "chiral fences" to shield the first and third quadrants. Use of the PyBidine-Cu(OTf)(2) complex as a catalyst enabled the highly endo-selective reaction of imino esters and nitroalkenes to give the adducts in up to 99% ee.