N-(7,8-dihydronaphthalen-2-yl)benzamide | 107275-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(7,8-dihydronaphthalen-2-yl)benzamide
• 英文别名: N-(7,8-dihydro-[2]naphthyl)-benzamide；N-(7,8-Dihydro-[2]naphthyl)-benzamid；2-Benzoylamino-7,8-dihydronaphthalin
• CAS: 107275-03-6
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: IQNQIJBPENYNLD-UHFFFAOYSA-N

物化性质

• 熔点：
  170.2-172 °C
• 沸点：
  324.2±31.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-(7,8-dihydronaphthalen-2-yl)benzamide 在 羟基甲苯磺酰碘苯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以77%的产率得到N-(1-(dimethoxymethyl)-2,3-dihydro-1H-inden-5-yl)benzamide
  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：

  N-(5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)benzamide 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以0.735 g的产率得到N-(7,8-dihydronaphthalen-2-yl)benzamide
  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。