2-(5-isopropoxy-4-(isopropoxycarbonyl)-5-oxo-3-phenylpentanoyl)pyridine 1-oxide | 1338699-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-isopropoxy-4-(isopropoxycarbonyl)-5-oxo-3-phenylpentanoyl)pyridine 1-oxide
• CAS: 1338699-03-8
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: IJIKEHGGFYKEOL-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  96.61
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  丙二酸二异丙酯 、 2-cinnamoylpyridine 1-oxide 在 C₆₄H₇₉N₂O₄Sc 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 以40%的产率得到
  参考文献：
  名称：

  Asymmetric Michael addition of malonates to unsaturated ketones catalyzed by rare earth metal complexes bearing phenoxy functionalized chiral diphenylprolinolate ligands

  摘要：

  A simple, efficient catalytic asymmetric Michael addition of malonates to unsaturated ketones has been successfully developed. This process was promoted by rare earth metal complexes 1-4 bearing a chiral phenoxy functionalized prolinol ligand at room temperature [(LRE)-R-1((LH)-H-1) (H2L1 = (S)-2,4-di-tert-butyl-6-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)phenol, RE = Yb 1, Y 2, Sc 3 and (LSc)-Sc-2((LH)-H-2) 4 (H2L2 = (S)-2,4-di-dimethylbenzy1-6-(2-(hydroxydiphenylmethyl)-pyrrolidin-1-yl)methyl)phenol)]. Complex 3 was the best catalyst in the transformation and the products were obtained in,up to 99% yield and with 90% ee. In addition, the molecular structures of the catalysts were well characterized, including X-ray determination of complex 3. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.07.014

文献信息

• Enantioselective Michael Addition of Malonates to 2-Enoylpyridine <i>N</i>-Oxides Catalyzed by Chiral Bisoxazoline–Zn(II) Complex
  作者：Sumit K. Ray、Pradeep K. Singh、Vinod K. Singh

  DOI：10.1021/ol202405v

  日期：2011.11.4

  An enantioselective Michael addition of malonates to 2-enoylpyridine N-oxides catalyzed by a chiral bisoxazoline–Zn(II) complex has been developed. The corresponding Michael adducts have been obtained in high yields with up to 96% ee. A plausible transition-state model has been proposed to explain the stereochemical outcome of the reaction.

  已开发了由手性双恶唑啉-Zn（II）络合物催化的丙二酸酯向2-烯酰基吡啶N-氧化物的对映选择性迈克尔加成反应。已经以高达96％ee的高收率获得了相应的迈克尔加合物。已经提出了一个合理的过渡态模型来解释反应的立体化学结果。