3-[2-(3,4-dihydro-1H-isoquinolin-2-yl)phenyl]prop-2-enal | 1240591-76-7

• 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: 3-[2-(3,4-dihydro-1H-isoquinolin-2-yl)phenyl]prop-2-enal
• CAS: 1240591-76-7
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: SUTQPYKGRWJQBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  二苄基马来酸酯 、 3-[2-(3,4-dihydro-1H-isoquinolin-2-yl)phenyl]prop-2-enal 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， 以63%的产率得到dibenzyl 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

• Microwave-Assisted Organocatalytic Synthesis of Tetrahydroquinolines via Hydride Transfer and Cyclization
  作者：You-Kyung Kwon、Young-Ku Kang、Dae-Young Kim

  DOI：10.5012/bkcs.2011.32.5.1773

  日期：2011.5.20

  E-mail: [e-mail] February 25, 2011, Accepted March 31, 2011Key Words : Tetrahydroquinolines, Microwave activation, Hydride transfer, Organocatalysis, Imminium ca-talysisTetrahydroquinoline derivatives have attracted conside-rable attention from organic and medicinal chemists pri-marily because they display a wide range of physiologicalactivities.

  E-mail: [e-mail] February 25, 2011, Accepted March 31, 2011 关键词：四氢喹啉、微波活化、氢化物转移、有机催化、亚胺催化- 主要是因为它们表现出广泛的生理活动。