7,8-dihydronaphthalen-2-yl acetate | 197505-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7,8-dihydronaphthalen-2-yl acetate
• 英文别名: 6-acetoxy-3,4-dihydronaphthalene
• CAS: 197505-40-1
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: AHRHOGXDIJJCAB-UHFFFAOYSA-N

物化性质

• 沸点：
  293.1±29.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟乙醇 、 7,8-dihydronaphthalen-2-yl acetate 在 羟基甲苯磺酰碘苯 作用下， 反应 0.08h， 以60%的产率得到1-(bis(2,2,2-trifluoroethoxy)methyl)-2,3-dihydro-1H-inden-5-yl acetate
  参考文献：
  名称：

  Iodine(III)-Mediated Ring Contraction Reactions: Synthesis of Oxygen- and Nitrogen-Substituted Indanes

  摘要：

  The synthesis of oxygen-and nitrogen-substituted indanes was successfully performed by iodine(III)-mediated ring contraction of 1,2-dihydronaphthalenes. Acetoxy and benzoyloxy alkenes afforded indanes in 60-71% yield, irrespective of their position on aromatic ring. Similarly, the nitrogen containing substrates protected with 9-fluorenylmethyloxycarbonyl (Fmoc) and benzoyl (Bz) groups smoothly undergoes ring contraction giving indanes in 64-77% yield. The tosyl-protected substrate resulted only in addition products.

  DOI：

  10.5935/0103-5053.20160065
• 作为产物：
  描述：

  (5-Hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl) acetate 在 草酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以76.6 mg的产率得到7,8-dihydronaphthalen-2-yl acetate
  参考文献：
  名称：

  Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins

  摘要：

  An enantioselective synthesis of substituted 2-aminotetralins from dihydronaphthalenes in four steps is described. The key step is the Jacobsen's (diimine)copper-catalyzed asymmetric aziridination of dihydronaphthalenes to the respective aziridines in 33-82% yields and 60-87% enantiomeric excess. The enantioselectivity and the yield were dependent on the properties of the nitrene precursor. pTs=NIPh appeared in general to give better results than pNsN=IPh. Aziridines were ring-opened in the benzylic position by catalytic hydrogenolysis in quantitative yields, and deprotected in two steps to the respective 2-aminotetralins in 66-85% yields. The synthesis of (S)-2-aminotetralin (>98% ee) and (S)-2-amino-7-methoxytetralin (56% ee) were accomplished in 30 and 52% overall yields, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.010

文献信息

• Metal-Free Asymmetric Synthesis of Indanes through Chiral Hypervalent Iodine(III)-Mediated Ring Contraction
  作者：Anees Ahmad、Luiz F. Silva

  DOI：10.1021/acs.joc.5b02803

  日期：2016.3.4

  The iodine(III)-mediated asymmetric oxidative rearrangement of 1,2-dihydronaphthalenes was investigated to prepare optically active 1-substituted indanes. The chiral hypervalent iodine species is generated in situ from a chiral aryl iodide, prepared in 94% yield in one step. This metal-free protocol was applied to different cyclic alkenes, substituted with oxygen, with nitrogen, or at position 1 with

  研究了碘（III）介导的1,2-二氢萘的不对称氧化重排，以制备旋光性1取代的茚满。手性高价碘物质是从一个步骤中以94％的收率制备的手性芳基碘原位生成的。将此无金属方案应用于不同的环状烯烃，这些环状烯烃被氧，氮取代或在1位被芳基或甲基取代。茚满可以分离为乙缩醛或乙醇，最高含量为78％ee。
• Iodine(III)-Mediated Ring Contraction Reactions: Synthesis of Oxygen- and Nitrogen-Substituted Indanes
  作者：Anees Ahmad、Luiz F. Silva Júnior

  DOI：10.5935/0103-5053.20160065

  日期：——

  The synthesis of oxygen-and nitrogen-substituted indanes was successfully performed by iodine(III)-mediated ring contraction of 1,2-dihydronaphthalenes. Acetoxy and benzoyloxy alkenes afforded indanes in 60-71% yield, irrespective of their position on aromatic ring. Similarly, the nitrogen containing substrates protected with 9-fluorenylmethyloxycarbonyl (Fmoc) and benzoyl (Bz) groups smoothly undergoes ring contraction giving indanes in 64-77% yield. The tosyl-protected substrate resulted only in addition products.
• Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins
  作者：Jon Erik Aaseng、Silje Melnes、Gard Reian、Odd R. Gautun

  DOI：10.1016/j.tet.2010.11.010

  日期：2010.12

  An enantioselective synthesis of substituted 2-aminotetralins from dihydronaphthalenes in four steps is described. The key step is the Jacobsen's (diimine)copper-catalyzed asymmetric aziridination of dihydronaphthalenes to the respective aziridines in 33-82% yields and 60-87% enantiomeric excess. The enantioselectivity and the yield were dependent on the properties of the nitrene precursor. pTs=NIPh appeared in general to give better results than pNsN=IPh. Aziridines were ring-opened in the benzylic position by catalytic hydrogenolysis in quantitative yields, and deprotected in two steps to the respective 2-aminotetralins in 66-85% yields. The synthesis of (S)-2-aminotetralin (>98% ee) and (S)-2-amino-7-methoxytetralin (56% ee) were accomplished in 30 and 52% overall yields, respectively. (C) 2010 Elsevier Ltd. All rights reserved.