8-methoxy-4-methyl-3,4-dihydro-2H-naphthalen-1-one | 958458-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 8-methoxy-4-methyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 3,4-dihydro-8-methoxy-4-methylnaphthalen-1(2H)-one
• CAS: 958458-98-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: QARALFBCBNRONH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：

  8-methoxy-4-methyl-3,4-dihydro-2H-naphthalen-1-one 、 异丙基氯化镁 以 四氢呋喃 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Total Synthesis of (±)- Cis -5-Hydroxycalamenene

  摘要：

  A total synthesis of (+/-)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-alpha-tetralone 3. Grignard reaction of compound 5 with isopropylmagnesium chloride, followed by dehydration and aromatization, provided the substituted naphthalene 7 whose conversion to (+/-)-cis-5-hydroxycalamenene 1 was accomplished by demethylation, formylation, and hydrogenation.

  DOI：

  10.1080/00397910802026204
• 作为产物：
  描述：

  1-methyl-5-methoxytetralin 在 叔丁基过氧化氢 、 sodium chlorite 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以60%的产率得到8-methoxy-4-methyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Total Synthesis of (±)- Cis -5-Hydroxycalamenene

  摘要：

  A total synthesis of (+/-)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-alpha-tetralone 3. Grignard reaction of compound 5 with isopropylmagnesium chloride, followed by dehydration and aromatization, provided the substituted naphthalene 7 whose conversion to (+/-)-cis-5-hydroxycalamenene 1 was accomplished by demethylation, formylation, and hydrogenation.

  DOI：

  10.1080/00397910802026204

文献信息

• Activation of 1,1-Difluoro-1-alkenes with a Transition-Metal Complex:  Palladium(II)-Catalyzed Friedel–Crafts-Type Cyclization of 4,4-(Difluorohomoallyl)arenes
  作者：Misaki Yokota、Daishi Fujita、Junji Ichikawa

  DOI：10.1021/ol702279w

  日期：2007.10.1

  Cationic palladium(II) ([Pd(MeCN)(4)](BF4)(2)) provides the first transition-metal-catalyzed method for electrophilic activation of electron-deficient 1,1-difluoro-1-alkenes, which allows their Friedel-Crafts-type cyclization with an intramolecular aryl group via a Wacker-type process. By using BF3 center dot OEt2, the cyclization was effected by a catalytic amount of the palladium without its reoxidation.
• Total Synthesis of (±)-<b> <i>Cis</i> </b>-5-Hydroxycalamenene
  作者：Po S. Poon Ng、Ajoy K. Banerjee

  DOI：10.1080/00397910802026204

  日期：2008.6.20

  A total synthesis of (+/-)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-alpha-tetralone 3. Grignard reaction of compound 5 with isopropylmagnesium chloride, followed by dehydration and aromatization, provided the substituted naphthalene 7 whose conversion to (+/-)-cis-5-hydroxycalamenene 1 was accomplished by demethylation, formylation, and hydrogenation.