3-(7-methoxy-1-methyl-3,4-dihydro-2-naphthyl)propionic acid | 194918-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(7-methoxy-1-methyl-3,4-dihydro-2-naphthyl)propionic acid
• 英文别名: 3-(7-Methoxy-1-methyl-3,4-dihydronaphthalen-2-yl)propanoic acid
• CAS: 194918-68-8
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: IJMSCEBVKIAPAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(7-methoxy-1-methyl-3,4-dihydro-2-naphthyl)propionic acid 在 dirhodium tetraacetate 、 草酰氯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 二氯甲烷 、 三氟乙酸 、 苯 为溶剂， 反应 4.67h， 生成
  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：

  7-甲氧基-1-萘满酮 在 氢氧化钾 、 硫酸 、 sodium ethanolate 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 水 为溶剂， 反应 13.0h， 生成 3-(7-methoxy-1-methyl-3,4-dihydro-2-naphthyl)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

文献信息

• 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
  作者：Paolo Manitto、Diego Monti、Giovanna Speranza

  DOI：10.1021/jo970631k

  日期：1997.9.1

  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.