3,4-dihydro-6-methyl-7-methoxy-2(1H)-naphthalenone | 122334-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3,4-dihydro-6-methyl-7-methoxy-2(1H)-naphthalenone
• 英文别名: 7-methoxy-6-methyl-3,4-dihydro-1H-naphthalen-2-one
• CAS: 122334-07-0
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: PDPWGPQGWRXIBR-UHFFFAOYSA-N

物化性质

• 沸点：
  325.7±42.0 °C(predicted)
• 密度：
  1.099±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：

  3,4-dihydro-6-methyl-7-methoxy-2(1H)-naphthalenone 在 铂 氢溴酸 、 氢气 、 对甲苯磺酸 、 溶剂黄146 作用下， 反应 73.5h， 生成 2-(di-n-propylamino)-6-methyl-7-hydroxytetralin
  参考文献：
  名称：

  Introduction of a putative dopaminergic prodrug moiety into a 6,7-substitution pattern characteristic of certain 2-aminotetralin dopaminergic agonists

  摘要：

  On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substitution pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.

  DOI：

  10.1021/jm00129a029
• 作为产物：
  描述：

  1,2,3,4-tetrahydro-6-methyl-7-methoxy-1-naphthalenol 在 盐酸 、 potassium hydrogensulfate 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 3,4-dihydro-6-methyl-7-methoxy-2(1H)-naphthalenone
  参考文献：
  名称：

  Introduction of a putative dopaminergic prodrug moiety into a 6,7-substitution pattern characteristic of certain 2-aminotetralin dopaminergic agonists

  摘要：

  On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substitution pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.

  DOI：

  10.1021/jm00129a029

文献信息

• The First Synthesis of Natural Occurring Juncaceae Coumarin, 9-Hydroxy-8-methyl-3H-benzo[f]chromen-3-one, Featuring a One-pot Rearrangement and Aromatization Cascade
  作者：Yung-Son Hon、Ya-Chun Hong、Bor-Cherng Hong、Ju-Hsiou Liao

  DOI：10.1002/jccs.201100481

  日期：2012.3

  The synthesis of benzocoumarins from β‐tetralones has been achieved via two pathways in the first total synthesis of the Juncaceae natural product, 9‐hydroxy‐8‐methyl‐3H‐benzo[f]chromen‐3‐one, featuring a one‐pot rearrangement and aromatization cascade.

  从β四氢萘酮benzocoumarins的合成已经在第一全合成通过两条途径达到灯心草科天然产物，9-羟基-8-甲基-3- ħ -苯并[ ˚F ]色烯-3-酮，设有一个单锅重排和芳香化级联。
• Introduction of a putative dopaminergic prodrug moiety into a 6,7-substitution pattern characteristic of certain 2-aminotetralin dopaminergic agonists
  作者：Joseph G. Cannon、Claire Diane True、John Paul Long、Ranbir K. Bhatnagar、Paul Leonard、Jan R. Flynn

  DOI：10.1021/jm00129a029

  日期：1989.9

  On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substitution pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.