4-(4-Methoxy-1-naphthyl)butan-2-one | 68427-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(4-Methoxy-1-naphthyl)butan-2-one
• 英文别名: 4-(4-Methoxynaphthalen-1-yl)butan-2-one
• CAS: 68427-28-1
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: AYKLAYHHDBNQGW-UHFFFAOYSA-N

物化性质

• 沸点：
  372.9±17.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-羟基-2-丁酮 、 1-甲氧基萘 在 Al⁽³⁺⁾-montmorillonite 作用下， 反应 48.0h， 以58%的产率得到4-(4-Methoxy-1-naphthyl)butan-2-one
  参考文献：
  名称：

  Cation-Exchanged Montmorillonite-Catalyzed Facile Friedel-Crafts Alkylation of Hydroxy and Methoxy Aromatics with 4-Hydroxybutan-2-one To Produce Raspberry Ketone and Some Pharmaceutically Active Compounds

  摘要：

  The Friedel-Crafts alkylation of hydroxy and methoxy aromatics with 4-hydroxybutan-2-one (gamma-KB) in the presence of a cation-exchanged montmorillonite (M(n+)-mont; M(n+) = Zr4+, Al3+, Fe3+, and Zn2+) was investigated. Phenol was C-alkylated regiospecifically with gamma-KB in the presence of Zr4+-, Al3+-, or Fe3+-mont to produce 4-(4-hydroxyphenyl)butan-2-one (raspberry ketone) in 31-35% GLC yield. Anisole, 2-methoxynaphthalene, and 1-methoxynaphthalene were regiospecifically C-alkylated to produce 4-(4-methoxyphenyl)butan-2-one, 4-(2-methoxy-1-naphthyl)butan-2-one (pharmaceutically active), and 4-(4-methoxy-1-naphthyl)butan-2-one, respectively. Al3+- and Fe3+-mont were the most effective catalysts in these cases (13-58%; isolated yield). gamma-KB could be used as an alkylating agent instead of the highly toxic 3-buten-2-one (MVK) which also polymerizes easily.

  DOI：

  10.1021/jo00099a017

文献信息

• 4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds
  作者：Alexander C. Goudie、Laramie M. Gaster、Antony W. Lake、Carl J. Rose、Patricia C. Freeman、Bryn O. Hughes、David Miller

  DOI：10.1021/jm00210a016

  日期：1978.12

  A series of compounds related to 4-(6-methoxy-2-naphthyl)butan-2-one has been prepared and tested for antiinflammatory activity by the cotton pellet granuloma method. Compounds possessing a small lipophilic group such as methoxyl, methyl, or chloro in the 6 position in conjunction with a butan-2-one side chain in the 2 position of the naphthalene ring were most active. The indtroduction of a methyl

  已经制备了一系列与4-（6-甲氧基-2-萘基）丁酮-2-酮有关的化合物，并通过棉粒肉芽肿法测试了其抗炎活性。在6位具有小亲脂性基团（如甲氧基，甲基或氯）并在萘环2位具有丁2-侧链的化合物最具活性。沿侧链引入甲基总是有害的。通常通过形成丁-2-醇侧链的酯来保持良好的活性。
• Tateiwa Jun-ichi, Horiuchi Hiroki, Hashimoto Keiji, Yamauchi Takayoshi, U+, J. Org. Chem, 59 (1994) N 20, S 5901-5904
  作者：Tateiwa Jun-ichi, Horiuchi Hiroki, Hashimoto Keiji, Yamauchi Takayoshi, U+

  DOI：——

  日期：——
• Cation-Exchanged Montmorillonite-Catalyzed Facile Friedel-Crafts Alkylation of Hydroxy and Methoxy Aromatics with 4-Hydroxybutan-2-one To Produce Raspberry Ketone and Some Pharmaceutically Active Compounds
  作者：Jun-ichi Tateiwa、Hiroki Horiuchi、Keiji Hashimoto、Takayoshi Yamauchi、Sakae Uemura

  DOI：10.1021/jo00099a017

  日期：1994.10

  The Friedel-Crafts alkylation of hydroxy and methoxy aromatics with 4-hydroxybutan-2-one (gamma-KB) in the presence of a cation-exchanged montmorillonite (M(n+)-mont; M(n+) = Zr4+, Al3+, Fe3+, and Zn2+) was investigated. Phenol was C-alkylated regiospecifically with gamma-KB in the presence of Zr4+-, Al3+-, or Fe3+-mont to produce 4-(4-hydroxyphenyl)butan-2-one (raspberry ketone) in 31-35% GLC yield. Anisole, 2-methoxynaphthalene, and 1-methoxynaphthalene were regiospecifically C-alkylated to produce 4-(4-methoxyphenyl)butan-2-one, 4-(2-methoxy-1-naphthyl)butan-2-one (pharmaceutically active), and 4-(4-methoxy-1-naphthyl)butan-2-one, respectively. Al3+- and Fe3+-mont were the most effective catalysts in these cases (13-58%; isolated yield). gamma-KB could be used as an alkylating agent instead of the highly toxic 3-buten-2-one (MVK) which also polymerizes easily.