N-((1R,2R)-5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-propionamide | 85378-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: N-((1R,2R)-5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-propionamide
• CAS: 85378-74-1；85378-80-9
• 化学式: C₁₈H₂₇NO₂
• 分子量: 289.418
• InChiKey: XWKHYURNXGVOEI-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-((1R,2R)-5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-propionamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 顺-(+)-5-甲氧基-1-甲基-2-(二正丙基氨基)萘满马来酸
  参考文献：
  名称：

  A short and efficient asymmetric synthesis of (1S,2R)-(+)-5-methoxy-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232)

  摘要：

  A general practical asymmetric synthesis of (1S,2R)-(+)-5-methoxyl-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232) was developed in a short and efficient method in high optical purity starting from commercially available 5-methoxy-1-tetralone. Asymmetric hydroboration of 5-methoxy-1-methyl-3,4-dihydronaphthalene with monoisopinocampheylborane followed by treatment with NaOH/H2O2 afforded key intermediate tetrahydronaphthol 4. Compound 4 was converted to the target molecule 1 using straightforward reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00333-x
• 作为产物：
  描述：

  1-methyl-5-methoxy-2-tetralone 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 24.5h， 生成 N-((1R,2R)-5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-propionamide
  参考文献：
  名称：

  C1-Methylated 5-hydroxy-2-(dipropylamino)tetralins: central dopamine-receptor stimulating activity

  摘要：

  C1-Methylated derivatives of the potent dopaminergic agonist 5-hydroxy-2-(di-n-propylamino)tetralin (6) have been synthesized and tested for central dopamine (DA) receptor stimulating activity, by using biochemical and behavioral tests in rats. Both cis- and trans-5-hydroxy-1-methyl-2-(di-n-propylamino) tetralin (4 and 3) may be classified as central DA-receptor agonists, albeit of lower potency than 6. The results obtained indicate that both 4 and 3 display DA-autoreceptor stimulation capacity. However, only one of the isomers, trans-3, is able to elicit clear-cut postsynaptic DA receptor agonist actions at larger doses. 5-Hydroxy-1,1-dimethyl-2-(n-propylamino) tetralin (5) was found to be inactive.

  DOI：

  10.1021/jm00374a012