2-(1,4-dihydronaphthalen-1-yl)-2-methylpropionic acid methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1,4-dihydronaphthalen-1-yl)-2-methylpropionic acid methyl ester
• 英文别名: Methyl 2-(1,4-dihydronaphthalen-1-yl)-2-methylpropanoate
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: KIIJHJJLNDNSAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氟甲基磺酰氟 、 silver trifluoromethanesulfonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.5h， 以77%的产率得到2-(1,4-dihydronaphthalen-1-yl)-2-methylpropionic acid methyl ester
  参考文献：
  名称：

  Dearomatization of Naphthalene:  Stereoselective cis-1,4 Tandem Additions Promoted by Osmium(II)

  摘要：

  The naphthalene complex of pentaammineosmium(II) (1) reacts with four different classes of electrophiles to form 1-naphthalenium species 2-5. These eta(3)-allyl complexes react stereospecifically with a variety of nucleophiles to form cis-1,4-dihydronaphthalene complexes. The entire reaction sequence may be performed outside a glovebox in two steps using conventional techniques.

  DOI：

  10.1021/ja980624t

文献信息

• Diastereo- and Enantioselective Dearomatization of Rhenium-Bound Naphthalenes
  作者：Fei Ding、Mark T. Valahovic、Joseph M. Keane、Mitchell R. Anstey、Michal Sabat、Carl O. Trindle、W. Dean Harman

  DOI：10.1021/jo030318k

  日期：2004.4.1

  Dihapto-coordinated naphthalene complexes of the form TpRe(CO)(L)(eta(2) -naphthalene) (L = PMe3, pyridine, or 1-methylimidazole) undergo electrophilic addition with dimethoxymethane and with various Michael acceptors to generate 1H-naphthalenium species. These naphthalenium. complexes undergo intra- or intermolecular nucleophilic addition reactions with stabilized enolates, silyl ketene acetals, or enols to form the corresponding dihydronaphthalene complexes. Oxidative decomplexation generates the free dihydronaphthalene. When a resolved form of the rhenium dearomatization agent is used, these reactions can be performed enantioselectively. DFT calculations provide a useful guide in explaining the observed stereochemistry. Depending on reaction conditions, a Michael-Michael ring-closure sequence (MIMIRC) or a net [2 + 4] cycloaddition with the bound naphthalene is also observed, and the corresponding tricyclic molecules can be removed from the metal in high yield.
• Ligand-Modulated Stereo- and Regioselective Tandem Addition Reactions of Rhenium-Bound Naphthalene
  作者：Mark T. Valahovic、T. Brent Gunnoe、Michal Sabat、W. Dean Harman

  DOI：10.1021/ja012066f

  日期：2002.4.1

  A series of complexes of the form TpRe(CO)(L)(eta(2)-naphthalene) (Tp = hydridotris(pyrazolyl)borate) undergoes tandem electrophile/nucleophile addition reactions with a high degree of regiocontrol depending on the auxiliary ligand, L. When L = PMe3, the reaction of the eta(2)-naphthalene complex with triflic acid followed by a silyl ketene acetal favors the 1,4-addition product, whereas when L = pyridine, N,N-dimethylaminopyridine, N-methylimidazole, or NH3 the 1,2-addition product is favored. These reactions proceed with excellent stereocontrol: both electrophile (H+, D+) and nucleophile (silyl ketene acetal) add anti to the face of metal coordination, and a single coordination diastereomer can be isolated for each reaction. one-electron oxidation of the Re complex affords the corresponding free dihydronaphthalene in good yield.