7,8-dihydronaphthalen-1-yl acetate | 51927-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7,8-dihydronaphthalen-1-yl acetate
• 英文别名: 1-acetoxy-7,8-dihydronaphthalene
• CAS: 51927-50-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: TUTZPBSDZXAOBL-UHFFFAOYSA-N

物化性质

• 沸点：
  302.2±31.0 °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：

  7,8-dihydronaphthalen-1-yl acetate 在 羟基甲苯磺酰碘苯 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以55%的产率得到罗替戈汀EP杂质K
  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：

  1,5-二羟基-1,2,3,4-四氢萘 在 4-二甲氨基吡啶 、 磷酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 7,8-dihydronaphthalen-1-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。
• Lipase-catalyzed resolution of 5-acetoxy-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene. Application to the synthesis of (+)-(3R,4S)-cis-4-hydroxy-6-deoxyscytalone, a metabolite isolated from Colletotrichum acutatum
  作者：Daniel Jiménez-Teja、Mourad Daoubi、Isidro G. Collado、Rosario Hernández-Galán

  DOI：10.1016/j.tet.2009.02.054

  日期：2009.4

  (+)-cis-4-Hyd Foxy-6-deoxyscytalone, a natural product bio-synthesized by Colletotrichum sp., has been prepared and its absolute configuration confirmed as 3R,4S, the key step being a kinetic racemic resolution of a cis-diol easily obtained from commercial 1,2,3.4-tetrahydronaphthalen-1,5-diol. Four lip ases and different reaction conditions were tested in order to obtain the best yield and enantiomeric excess. Confirmation of absolute configuration was made by NMR using a single-derivatization low-temperature Procedure and MPA as the auxiliary reagent. (C) 2009 Elsevier Ltd. All rights reserved.

  **(+)-顺式-4-羟基福烯-6-脱氧赛肽酮**，一种由Colletotrichum sp.生物合成的天然产物，已被成功制备，其绝对构型经确认为3R,4S。关键步骤在于对易从商业1,2,3,4-四氢萘-1,5-二醇获取的顺式二醇进行动力学消旋拆分。同时测试了四种脂肪酶和不同反应条件，以获得最优产率和对映体过量。绝对构型的确证通过核磁共振（NMR）完成，采用了单一步骤衍生化低温方法，并以MPA作为辅助试剂。 （C）2009 Elsevier Ltd. 保留所有权利。
• US3943149A
  申请人：——

  公开号：US3943149A

  公开（公告）日：1976-03-09
• 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.