5-methoxy-3-methyl-2-tetralone | 105372-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-methoxy-3-methyl-2-tetralone
• 英文别名: 5-methoxy-3-methyl-3,4-dihydro-1H-naphthalen-2-one
• CAS: 105372-20-1
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: FZRLJCQWXWQTGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-methyl-2-tetralone 在 lithium aluminium tetrahydride 、 盐酸羟胺 、 sodium acetate 、 sodium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 异丙醇 为溶剂， 反应 5.0h， 生成 trans-5-methoxy-3-methyl-2-(n-propylamino)tetralin
  参考文献：
  名称：

  C3-Methylated 5-hydroxy-2-(dipropylamino)tetralins: conformational and steric parameters of importance for central dopamine receptor activation

  摘要：

  C3-Methyl-substituted derivatives of the potent dopamine (DA) receptor agonist 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH-DPAT) have been synthesized and their conformational preferences have been studied by use of NMR spectroscopy, X-ray crystallography, and molecular mechanics calculations (MMP2). The compounds were tested for activity at central DA receptors, by use of biochemical and behavioral tests in rats. (2R,3S)-5-Hydroxy-3-methyl-2-(di-n-propylamino)tetralin [(-)-8] was demonstrated to be a highly potent DA receptor agonist, while the other new compounds were of low potency or inactive. Results obtained confirmed the hypothesis that the tetralin inversion angle phi and the direction of the N-electron pair (N-H) tau N are conformational parameters of critical importance for DA D2 receptor activation in the 2-aminotetralin series. The high potency of (-)-8 allowed an extension of a previously defined "partial DA D2 receptor excluded volume".

  DOI：

  10.1021/jm00390a004
• 作为产物：
  描述：

  1,2,3,4-tetrahydro-2,3-methano-2,5-dimethoxynaphthalene 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以85%的产率得到5-methoxy-3-methyl-2-tetralone
  参考文献：
  名称：

  Lundkvist, J. R. Michael; Johansson, Anette M.; Arvidson, Lars-Erik, Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry, 1986, vol. 40, # 6, p. 508 - 511

  摘要：

  DOI：

文献信息

• Syntheses of 5-, 7-, and 8-methoxy-3-methyl-2-tetralones
  作者：Anette M. Johansson、Charlotta Mellin、Uli Hacksell

  DOI：10.1021/jo00376a038

  日期：1986.12
• LUNDKVIST J. R. M.; JOHANSSON A. M.; ARVIDSSON L. -E.; HACKSELL U., ACTA CHEM. SCAND., 40,(1986) N 6, 508-511
  作者：LUNDKVIST J. R. M.、 JOHANSSON A. M.、 ARVIDSSON L. -E.、 HACKSELL U.

  DOI：——

  日期：——
• JOHANSSON A. M.; MELLIN CH.; HACKSELL U., J. ORG. CHEM., 51,(1986) N 26, 5252-5258
  作者：JOHANSSON A. M.、 MELLIN CH.、 HACKSELL U.

  DOI：——

  日期：——
• JOHANSSON A. M.; NILSSON J. L. G.; KARLEN A.; HACKSELL U.; SVENSSON K.; C+, J. MED. CHEM., 30,(1987) N 7, 1135-1144
  作者：JOHANSSON A. M.、 NILSSON J. L. G.、 KARLEN A.、 HACKSELL U.、 SVENSSON K.、 C+

  DOI：——

  日期：——
• C3-Methylated 5-hydroxy-2-(dipropylamino)tetralins: conformational and steric parameters of importance for central dopamine receptor activation
  作者：Anette M. Johansson、J. Lars G. Nilsson、Anders Karlen、Uli Hacksell、Kjell Svensson、Arvid Carlsson、Lennart Kenne、Staffan Sundell

  DOI：10.1021/jm00390a004

  日期：1987.7

  C3-Methyl-substituted derivatives of the potent dopamine (DA) receptor agonist 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH-DPAT) have been synthesized and their conformational preferences have been studied by use of NMR spectroscopy, X-ray crystallography, and molecular mechanics calculations (MMP2). The compounds were tested for activity at central DA receptors, by use of biochemical and behavioral tests in rats. (2R,3S)-5-Hydroxy-3-methyl-2-(di-n-propylamino)tetralin [(-)-8] was demonstrated to be a highly potent DA receptor agonist, while the other new compounds were of low potency or inactive. Results obtained confirmed the hypothesis that the tetralin inversion angle phi and the direction of the N-electron pair (N-H) tau N are conformational parameters of critical importance for DA D2 receptor activation in the 2-aminotetralin series. The high potency of (-)-8 allowed an extension of a previously defined "partial DA D2 receptor excluded volume".