6-methoxy-1-methyl-3,4-dihydro-2H-naphthalene-1-carboxylic acid | 113967-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methoxy-1-methyl-3,4-dihydro-2H-naphthalene-1-carboxylic acid
• CAS: 113967-22-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: IBMFBRDWGCBHPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  375.1±42.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  6-methoxy-1-methyl-3,4-dihydro-2H-naphthalene-1-carboxylic acid 在 dirhodium tetraacetate 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-Methoxy-8a-methyl-2,6,7,8-tetrahydroacenaphthylen-1-one
  参考文献：
  名称：

  Regiocontrol in the rhodium (II) catalysed reactions of 1,2,3,4-tetrahydro-1-naphthyl diazomethyl ketones: Potential applications to the synthesis of Galbulimima alkaloids

  摘要：

  The selectivity of diazoketone derived rhodium-carbenoid insertions into aromatic and aliphatic C-H bonds has been shown to be sensitive to the total steric environment of the participating groups and may be controlled by varying the steric bulk of the ligands on rhodium. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01252-5
• 作为产物：
  描述：

  1-methyl-1-methoxycarbonyl-6-methoxy-1,2,3,4-tetrahydronaphthalene 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.5h， 以93%的产率得到6-methoxy-1-methyl-3,4-dihydro-2H-naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Lewis Acid-Promoted Favorskii-Type Ring Contraction of Some Cyclic α-Bromo Ketones and Their Acetals

  摘要：

  加热α-溴环烷基芳基酮2a-d与氯化锌在甲醇中反应，获得了中等到良好的产率的环收缩产物3a-d，具有gem-甲基碳甲氧基功能。相关的α-溴酮7a-c的醇醚，缺乏氯原子邻近的甲基，经过加热在质子溶剂中反应，获得了可接受产率的环收缩酯8a-c。对目前的环收缩反应程序的局限性进行了讨论。

  DOI：

  10.1055/s-1987-28079

文献信息

• Lewis Acid-Promoted Favorskii-Type Ring Contraction of Some Cyclic α-Bromo Ketones and Their Acetals
  作者：Swaraj B. Maiti、S. R. Ray Chaudhuri、Amareshwar Chatterjee

  DOI：10.1055/s-1987-28079

  日期：——

  The α-bromo cycloalkyl aryl ketones 2a-d on heating with zinc chloride in methanol furnished in moderate to good yields the ring-contracted products 3a-d having gem methyl carbomethoxy function. The acetals of the related α-bromo ketones 7a-c, lacking the methyl group on the halogen-bearing carbon atom, afforded in acceptable yields the ring-contracted esters 8a-c when heated in protic solvent. The limitation of the present ring-contraction procedure has been discussed.

  加热α-溴环烷基芳基酮2a-d与氯化锌在甲醇中反应，获得了中等到良好的产率的环收缩产物3a-d，具有gem-甲基碳甲氧基功能。相关的α-溴酮7a-c的醇醚，缺乏氯原子邻近的甲基，经过加热在质子溶剂中反应，获得了可接受产率的环收缩酯8a-c。对目前的环收缩反应程序的局限性进行了讨论。
• MAITI, SWARAJ B.;RAY, CHAUDHURI S. R.;CHATTERJEE, AMARESHWAR, SYNTHESIS,(1987) N 9, 806-809
  作者：MAITI, SWARAJ B.、RAY, CHAUDHURI S. R.、CHATTERJEE, AMARESHWAR

  DOI：——

  日期：——
• Regiocontrol in the rhodium (II) catalysed reactions of 1,2,3,4-tetrahydro-1-naphthyl diazomethyl ketones: Potential applications to the synthesis of Galbulimima alkaloids
  作者：Lewis N. Mander、Adam P. Wells

  DOI：10.1016/s0040-4039(97)01252-5

  日期：1997.8

  The selectivity of diazoketone derived rhodium-carbenoid insertions into aromatic and aliphatic C-H bonds has been shown to be sensitive to the total steric environment of the participating groups and may be controlled by varying the steric bulk of the ligands on rhodium. (C) 1997 Elsevier Science Ltd.