1-Naphthol 2-cyanoethyl ether | 58889-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Naphthol 2-cyanoethyl ether
• 英文别名: 3-(1-Naphthoxy)-propanenitrile；α-naphthyl 2-cyanoethyl ether；<2-Cyan-ethyl>-naphthyl-(1)-ether；β-(1-Naphthoxy)-propionitril；α-Naphthol-<2-cyano-ethyl>-ether；β-(α-Naphthyloxy)-propionitril；α-Naphthol-(2-cyan-ethyl)-ether；3-(naphthalen-1-yloxy)propanenitrile；3-[1]naphthyloxy-propionitrile；3-(1-Naphthyloxy)propanenitrile；3-naphthalen-1-yloxypropanenitrile
• CAS: 58889-08-0
• 化学式: C₁₃H₁₁NO
• mdl: MFCD09930838
• 分子量: 197.236
• InChiKey: AJFRMLXENQDQIK-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C
• 沸点：
  394.3±25.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Naphthol 2-cyanoethyl ether 在 PPA 、 溴 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 3-溴-2,3-二氢-苯并[h]色烯-4-酮
  参考文献：
  名称：

  Sharma, S. D.; Kaur, Sukhjinder, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 6, p. 518 - 521

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-溴乙氧基)萘 以73%的产率得到
  参考文献：
  名称：

  Romanelli Gustavo P., Autino Juan C., Vitale Arturo A., Pomilio Alicia B., J. Chem. Res. Synop, (1993) N 9, S 386-387

  摘要：

  DOI：

文献信息

• Acid activated montmorillonite K-10 mediated intramolecular acylation: Simple and convenient synthesis of 4-chromanones
  作者：Ayisha F. Begum、Kalpattu K. Balasubramanian、Bhagavathy Shanmugasundaram

  DOI：10.1016/j.tetlet.2021.153372

  日期：2021.10

  in toluene under reflux for 30–45 min in good to excellent yields. Phenyl ring bearing various substituents at the ortho, meta, para positions undergo this cyclization reaction. This method involves simple work up and amenable for large scale preparations. The heterogeneous acid treated catalyst can be regenerated and used for up to three cycles with minimum loss of activity.

  3-芳氧基丙酸在 AA.Mont.K-10 的存在下在甲苯中回流 30-45 分钟，以良好到极好的产率进行分子内环化。在邻位、间位、对位带有各种取代基的苯基环会发生这种环化反应。该方法涉及简单的后处理，适用于大规模制备。经多相酸处理的催化剂可以再生并最多使用三个循环，而活性损失最小。
• Colonge; Guyot, Bulletin de la Societe Chimique de France, 1957, p. 1228
  作者：Colonge、Guyot

  DOI：——

  日期：——
• Areschka; Mahaux; Verbruggen, European Journal of Medicinal Chemistry, 1975, vol. 10, # 5, p. 463 - 469
  作者：Areschka、Mahaux、Verbruggen、et al.

  DOI：——

  日期：——
• Synthesis, characterization, and antimicrobial activity of novel substituted 2H-chromenyl acrylates
  作者：N. J. P. Subhashini、M. Ravi、D. Cherupally、B. China Raju、E. V. Reddy、H. Bee

  DOI：10.1134/s1070363216120586

  日期：2016.12

  The present study deals with conventional Witting olefination of 2H-chromene-3-carbaldehydes with stabilized ylide in the presence of dichloromethane to afford (2E)-ethyl-3-(4-chloro-2H-chromen-3-yl) acrylate derivatives. All the products were found to have E-geometry at C=C bond. The synthesized compounds were characterized by spectral data such as IR, H-1 NMR and MS. Compounds were screened for antimicrobial activity against strains of gram positive, gram negative bacterial and fungal strains. All compounds showed good antibacterial and antifungal activity.
• An efficient synthesis of 4-chromanones
  作者：Yong-Li Zhong、David T. Boruta、Donald R. Gauthier、David Askin

  DOI：10.1016/j.tetlet.2011.07.018

  日期：2011.9

  A two step efficient and practical synthesis of a variety of 4-chromanones is described. Phenols undergo a Michael addition to acrylonitriles in the presence of catalytic amounts of potassium carbonate and tert-butanol to generate the corresponding 3-aryloxypropanenitriles in 50-93% yields. Treatment of the resulting aryloxypropionitriles with 1.5 equiv of TfOH and 5 equiv of TFA, followed by an aqueous work up afforded 4-chromanones in moderate to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.