dimethyl 2-((R)-2-formyl-1-(2-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)ethyl)malonate | 1407535-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: dimethyl 2-((R)-2-formyl-1-(2-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)ethyl)malonate
• 英文别名: dimethyl 2-[(1R)-1-[2-(3,4-dihydro-1H-isoquinolin-2-yl)phenyl]-3-oxopropyl]propanedioate
• CAS: 1407535-53-8
• 化学式: C₂₃H₂₅NO₅
• 分子量: 395.455
• InChiKey: LVTYKZAEQJCASP-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-((R)-2-formyl-1-(2-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)ethyl)malonate 在 碳酸氢钠 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以35%的产率得到(13R)-dimethyl 13-(formylmethyl)-6,7-dihydro-11bH-isoquinolino[2,1-a]quinoline-12,12(13H)-dicarboxylate
  参考文献：
  名称：

  Asymmetric synthesis of ring-fused tetrahydroquinolines using organocatalytic enantioselective conjugate addition and cross-dehydrogenative coupling

  摘要：

  Enantioenriched ring-fused tetrahydroquinolines were synthesized by a facile and straightforward process involving the organocatalytic enantioselective conjugate addition reaction of malonates with o-N-tetrahydroisoquinolinyl-substituted cinnamaldehyde, followed by intramolecular cross-dehydrogenative coupling. Diphenylprolinol TMS ether was used as an organocatalyst in the asymmetric catalytic conjugate addition reaction and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was used as an oxidant in the cross-dehydrogenative coupling (CDC) reaction. The desired ring-fused tetrahydroquinolines were obtained in moderate yields and with high enantioselectivities (up to 97% ee). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.08.004
• 作为产物：
  描述：

  3-[2-(3,4-dihydro-1H-isoquinolin-2-yl)phenyl]prop-2-enal 、 丙二酸二甲酯 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以45%的产率得到dimethyl 2-((R)-2-formyl-1-(2-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)ethyl)malonate
  参考文献：
  名称：

  Asymmetric synthesis of ring-fused tetrahydroquinolines using organocatalytic enantioselective conjugate addition and cross-dehydrogenative coupling

  摘要：

  Enantioenriched ring-fused tetrahydroquinolines were synthesized by a facile and straightforward process involving the organocatalytic enantioselective conjugate addition reaction of malonates with o-N-tetrahydroisoquinolinyl-substituted cinnamaldehyde, followed by intramolecular cross-dehydrogenative coupling. Diphenylprolinol TMS ether was used as an organocatalyst in the asymmetric catalytic conjugate addition reaction and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was used as an oxidant in the cross-dehydrogenative coupling (CDC) reaction. The desired ring-fused tetrahydroquinolines were obtained in moderate yields and with high enantioselectivities (up to 97% ee). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.08.004

文献信息

• Asymmetric synthesis of ring-fused tetrahydroquinolines using organocatalytic enantioselective conjugate addition and cross-dehydrogenative coupling
  作者：Sung Hyuk Gwon、Sung-Gon Kim

  DOI：10.1016/j.tetasy.2012.08.004

  日期：2012.9

  Enantioenriched ring-fused tetrahydroquinolines were synthesized by a facile and straightforward process involving the organocatalytic enantioselective conjugate addition reaction of malonates with o-N-tetrahydroisoquinolinyl-substituted cinnamaldehyde, followed by intramolecular cross-dehydrogenative coupling. Diphenylprolinol TMS ether was used as an organocatalyst in the asymmetric catalytic conjugate addition reaction and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was used as an oxidant in the cross-dehydrogenative coupling (CDC) reaction. The desired ring-fused tetrahydroquinolines were obtained in moderate yields and with high enantioselectivities (up to 97% ee). (C) 2012 Elsevier Ltd. All rights reserved.