6-methoxy-5-methyl-3,4-dihydro-2(1H)-naphthalenone | 17215-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-methoxy-5-methyl-3,4-dihydro-2(1H)-naphthalenone
• 英文别名: 6-methoxy-5-methyl-2-tetralone；3,4-Dihydro-6-methoxy-5-methyl-2(1H)-naphthalenon；6-methoxy-5-methyl-3,4-dihydro-1H-naphthalen-2-one
• CAS: 17215-86-0
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: UXHPOKGCRFNMIK-UHFFFAOYSA-N

物化性质

• 沸点：
  328.2±42.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(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：

  6-methoxy-5-methyl-3,4-dihydro-2(1H)-naphthalenone 在 四氢吡咯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙腈 为溶剂， 生成 1-(3,4-二氢-6-甲氧基-5-甲基-1-(2-丙烯基)-2-萘基)-3-丁炔-3-酮
  参考文献：
  名称：

  juncusol的新型合成

  摘要：

  Juncusol（7）已通过新颖的电环化工艺从已知的β-四氢萘酮衍生物9开始制备。

  DOI：

  10.1016/s0040-4039(00)79645-6
• 作为产物：
  描述：

  2,6-dimethoxy-1-naphthalenecarbaldehyde 在 sodium tetrahydroborate 、 乙醇 、 sodium 作用下， 以 乙醇 为溶剂， 生成 6-methoxy-5-methyl-3,4-dihydro-2(1H)-naphthalenone
  参考文献：
  名称：

  Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists

  摘要：

  A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.

  DOI：

  10.1021/jm00238a008

文献信息

• Inverse electron demand diels-alder reaction of 3-carbomethoxy-2-pyrones with 1,1-dimethoxyethylene: a simple and mild method of aryl annulation
  作者：Dale L. Boger、Michael D. Mullican

  DOI：10.1016/s0040-4039(00)85651-8

  日期：1982.1

  A simple process for aryl annulation based on the inverse electron demand Diels-Alder reaction of 5,6-substituted-3-carbomethoxy-2-pyrones with 1,1-dimethoxyethylene is described.

  描述了基于5,6-取代的-3-羰基甲氧基-2-吡喃酮与1,1-二甲氧基乙烯的电子反需求Diels-Alder反应的芳基环化的简单方法。
• Aromatic ring synthesis by -aminopyrrole diels-alder reaction. Total synthesis of juncusol
  作者：Arthur G. Schultz、Ming Shen

  DOI：10.1016/s0040-4039(01)90436-8

  日期：1981.1

  A total synthesis of the cytotoxic phytoalexin juncusol (1) is described.

  描述了细胞毒性植物抗毒素juncusol（1）的全合成。
• Inverse electron demand Diels-Alder reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of oxygenated aromatics: benzene, phenol, catechol, resorcinol, and pyrogallol annulation. Regiospecific total synthesis of sendaverine and a preparation of 6,7-benzomorphans
  作者：Dale L. Boger、Michael D. Mullican

  DOI：10.1021/jo00195a033

  日期：1984.10
• Enynones in Organic Synthesis. 8. Synthesis of the Antimicrobial-Cytotoxic Agent Juncusol and Members of the Effusol Class of Phenols
  作者：Peter A. Jacobi、Joseph I. Kravitz、Wanjun Zheng

  DOI：10.1021/jo00107a017

  日期：1995.1

  Two new syntheses of phenols have been developed which have been utilized in an efficient preparation of the antimicrobial-cytotoxic agent juncusol (22) and several members of the effusol (23) class of phenols. These results complement our earlier studies with enynones of type 42 and provide for the highly efficient conversion of 42 to either methylenecyclopentenones 45 or phenols of type 47 or 54 with virtually 100% selectivity.
• Regiospecific total synthesis of juncusol
  作者：Dale L. Boger、Michael D. Mullican

  DOI：10.1021/jo00195a034

  日期：1984.10

表征谱图