5,6-dihydronaphthalen-2-yl acetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,6-dihydronaphthalen-2-yl acetate
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: GPJIFVRVSCRAKD-UHFFFAOYSA-N

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 、 5,6-dihydronaphthalen-2-yl acetate 在 羟基甲苯磺酰碘苯 作用下， 反应 0.08h， 以65%的产率得到3-(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：

  7-甲氧基-1-萘满酮 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 、 乙硫醇 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 3.0h， 生成 5,6-dihydronaphthalen-2-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

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。
• [EN] NOVEL SUBSTITUTED NAPHTHOPYRANS<br/>[FR] NOUVEAUX NAPHTOPYRANNES SUBSTITUES
  申请人：PPG INDUSTRIES, INC.

  公开号：WO1995016215A1

  公开（公告）日：1995-06-15

  (EN) Novel photochromic 2H-naphtho[1,2-b]pyrans with a 5-carboxyl or amido substituent and having an acceptable fade rate, high activated intensity and a high coloration rate are useful in photochromic articles such as ophthalmic lens.(FR) Des nouveaux 2H-naphto(1,2-b)pyrannes photochromes ayant un substituant 5-carboxyle ou amido et comportant un taux de décoloration acceptable, une forte intensité activée ainsi qu'un taux de coloration élevé, sont utiles dans des articles photochromes tels que des verres de contact ophtalmiques.
• 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.