1-[(3-甲氧基-2-硝基苯基)甲基]异喹啉 | 53055-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 1-[(3-甲氧基-2-硝基苯基)甲基]异喹啉
• 英文名称: 1-(3-Methoxy-2-nitrobenzyl)-isochinolin
• 英文别名: 1-(3-Methoxy-2-nitrobenzyl)isoquinoline；1-[(3-methoxy-2-nitrophenyl)methyl]isoquinoline
• CAS: 53055-08-6
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: XCXHDQXXPOJGDA-UHFFFAOYSA-N

物化性质

• 沸点：
  477.6±35.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(3-甲氧基-2-硝基苯基)甲基]异喹啉 在 palladium on activated charcoal 钾硼氢 、 氢气 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 1-(2-amino-3-methoxybenzyl)-2-propyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine

  摘要：

  The R-(-) and S-(+) enantiomers of 11-hydroxy-N-n-propylnoraporphine, (R)-3 and (S)-3, were synthesized in six steps from 1-(3-methoxy-2-nitrobenzyl)isoquinoline. Neuropharmacological evaluation of the R and S isomers (by affinity to dopamine receptor sites in rat brain tissues, induction of stereotyped behavior, and interaction with motor arousal induced by (R)-apomorphine in the rat) indicated that, similar to the 10,11-dihydroxy congener 2, both enantiomers can bind to dopamine receptors but that only (R)-3 activates them, whereas (S)-3 shows activity as a dopaminergic antagonist.

  DOI：

  10.1021/jm00402a024

文献信息

• Isoquinolines. 8. Ethylene oxide mediated conversion of isoquinolines to isoquinolones and oxazolidines. Its extension to related nitrogen heterocycles
  作者：Crist N. Filer、Felix E. Granchelli、Peter Perri、John L. Neumeyer

  DOI：10.1021/jo01316a026

  日期：1979.1
• GAO, YIGONG;ZONG, RUSHI;CAMPBELL, ALEXANDER;KULA, NORA S.;BALDESSARINI, R+, J. MED. CHEM., 31,(1988) N 7, 1392-1396
  作者：GAO, YIGONG、ZONG, RUSHI、CAMPBELL, ALEXANDER、KULA, NORA S.、BALDESSARINI, R+

  DOI：——

  日期：——
• FILER C. N.; GRANCHELLI F. E.; PERRI P.; NEUMEYER J. L., J. ORG. CHEM., 1979, 44, NO 2, 285-287
  作者：FILER C. N.、 GRANCHELLI F. E.、 PERRI P.、 NEUMEYER J. L.

  DOI：——

  日期：——
• Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine
  作者：Yigong Gao、Rushi Zong、Alexander Campbell、Nora S. Kula、Ross J. Baldessarini、John L. Neumeyer

  DOI：10.1021/jm00402a024

  日期：1988.7

  The R-(-) and S-(+) enantiomers of 11-hydroxy-N-n-propylnoraporphine, (R)-3 and (S)-3, were synthesized in six steps from 1-(3-methoxy-2-nitrobenzyl)isoquinoline. Neuropharmacological evaluation of the R and S isomers (by affinity to dopamine receptor sites in rat brain tissues, induction of stereotyped behavior, and interaction with motor arousal induced by (R)-apomorphine in the rat) indicated that, similar to the 10,11-dihydroxy congener 2, both enantiomers can bind to dopamine receptors but that only (R)-3 activates them, whereas (S)-3 shows activity as a dopaminergic antagonist.