3-(1-methyl-2-naphthyl)acrylic acid methyl ester | 194918-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1-methyl-2-naphthyl)acrylic acid methyl ester
• 英文别名: methyl 3-(1-methylnaphthalen-2-yl)prop-2-enoate
• CAS: 194918-72-4
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: PAXMAAIKVIZQSG-UHFFFAOYSA-N

物化性质

• 沸点：
  369.9±11.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(1-methyl-2-naphthyl)acrylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 23.0 ℃ 、101.32 kPa 条件下， 反应 4.0h， 以72%的产率得到3-(1-Methyl-naphthalen-2-yl)-propionic acid
  参考文献：
  名称：

  Rhodium(II)-Catalyzed Decomposition of 1-Diazo-4-(1- or 2-naphthyl)-2-butanones as a New Route to Rearranged Pimarane and Abietane Skeleta. Synthesis of Umbrosone

  摘要：

  The Rh-2(OAc)(4)-catalyzed intramolecular Buchner reaction of 1-diazo-4-(1- or 2-naphthyl)butan-2-ones was examined as a potential route to abietane and rearranged abietane derivatives. Treatment of the alpha-diazo ketone 26 with catalytic amount of dirhodium tetraacetate in CH2Cl2 at 0 degrees C furnished the tetracyclic derivative 27 in good yield. Addition of TFA to 27 (in CH2Cl2) resulted in an acid-induced opening of the cyclopropane ring to give the 4a- and 10a-methyldihydrophenanthrenones 28 and 29 in nearly equal amounts. These compounds and their analogs appear to be suitable intermediates for the synthesis of diterpenoids containing aromatic A or C rings. When the diazo ketone 34 was decomposed under Rh(II) catalysis, a 10-methyldihydroanthracenone (i.e., 36) was obtained as the main product, besides minor amounts of the expected tetracyclic ketone 35. The extension of this result to the preparation of the methoxy-substituted dihydroanthracenone 39 (52% yield) was exploited in a new total synthesis of umbrosone (6), an unusual diterpenoid possessing a rearranged linear skeleton.

  DOI：

  10.1021/jo970631k
• 作为产物：
  描述：

  2-溴-1-甲基萘 、 丙烯酸甲酯（MA） 在 bis(triphenylphosphine) palladium (Il) acetate 、 三乙胺 作用下， 以71%的产率得到3-(1-methyl-2-naphthyl)acrylic acid methyl ester
  参考文献：
  名称：

  Rhodium(II)-Catalyzed Decomposition of 1-Diazo-4-(1- or 2-naphthyl)-2-butanones as a New Route to Rearranged Pimarane and Abietane Skeleta. Synthesis of Umbrosone

  摘要：

  The Rh-2(OAc)(4)-catalyzed intramolecular Buchner reaction of 1-diazo-4-(1- or 2-naphthyl)butan-2-ones was examined as a potential route to abietane and rearranged abietane derivatives. Treatment of the alpha-diazo ketone 26 with catalytic amount of dirhodium tetraacetate in CH2Cl2 at 0 degrees C furnished the tetracyclic derivative 27 in good yield. Addition of TFA to 27 (in CH2Cl2) resulted in an acid-induced opening of the cyclopropane ring to give the 4a- and 10a-methyldihydrophenanthrenones 28 and 29 in nearly equal amounts. These compounds and their analogs appear to be suitable intermediates for the synthesis of diterpenoids containing aromatic A or C rings. When the diazo ketone 34 was decomposed under Rh(II) catalysis, a 10-methyldihydroanthracenone (i.e., 36) was obtained as the main product, besides minor amounts of the expected tetracyclic ketone 35. The extension of this result to the preparation of the methoxy-substituted dihydroanthracenone 39 (52% yield) was exploited in a new total synthesis of umbrosone (6), an unusual diterpenoid possessing a rearranged linear skeleton.

  DOI：

  10.1021/jo970631k