1-(3-nitrophenyl)but-3-yn-1-ol | 132927-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-nitrophenyl)but-3-yn-1-ol
• 英文别名: 1-(m-nitrophenyl)but-3-yn-1-ol
• CAS: 132927-18-5
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: ASJMYJGLGJOKEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-nitrophenyl)but-3-yn-1-ol 在 gold(III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 水 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 20.0h， 生成 5-(3-nitro-phenyl)-tetrahydrofuran-2-one
  参考文献：
  名称：

  A New Synthesis of γ-Butyrolactones via AuCl₃- or Hg(II)-Catalyzed Intramolecular Hydroalkoxylation of 4-Bromo-3-yn-1-ols

  摘要：

  An efficient conversion of 4-bromo-3-yn-1-ols to gamma-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.

  DOI：

  10.1021/ol2033493
• 作为产物：
  描述：

  allenylmagnesium bromide 、 间硝基苯甲醛 以 乙醚 为溶剂， 生成 1-(3-nitrophenyl)but-3-yn-1-ol
  参考文献：
  名称：

  A New Synthesis of γ-Butyrolactones via AuCl₃- or Hg(II)-Catalyzed Intramolecular Hydroalkoxylation of 4-Bromo-3-yn-1-ols

  摘要：

  An efficient conversion of 4-bromo-3-yn-1-ols to gamma-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.

  DOI：

  10.1021/ol2033493

文献信息

• Regioselective propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil
  作者：Jucleiton J.R. Freitas、Tulio R. Couto、Italo H. Cavalcanti、Juliano C.R. Freitas、Queila P.S. Barbosa、Roberta A. Oliveira

  DOI：10.1016/j.tetlet.2016.01.017

  日期：2016.2

  The propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil, an inexpensive and readily available clay, in a chemo- and regioselective way is described. The method is simple and avoids the use of air and moisture sensitive organometallics and products were obtained in good to moderate yields. (C) 2016 Elsevier Ltd. All rights reserved.
• Propargylation of Aldehydes Using Potassium Allenyltrifluoroborate
  作者：Roberta Oliveira、Túlio Couto、Jucleiton Freitas、Juliano Freitas、Italo Cavalcanti、Paulo Menezes

  DOI：10.1055/s-0034-1379163

  日期：——

  The commercially available resin Amberlyst A-31 was efficiently used to promote the propargylation of aldehydes using potassium allenyltrifluoroborate. The method is simple and fast, and the products were obtained in short reaction times in high yields and purity at room temperature in a regio- and chemoselective manner.
• Wu, Shihui; Huang, Bangzhou; Gao, Xiang, Synthetic Communications, 1990, vol. 20, # 9, p. 1279 - 1286
  作者：Wu, Shihui、Huang, Bangzhou、Gao, Xiang

  DOI：——

  日期：——
• WU, SHIHU;HUANG, BANGZHOU;GAO, XIANG, SYNTH. COMMUN., 20,(1990) N, C. 1279-1286
  作者：WU, SHIHU、HUANG, BANGZHOU、GAO, XIANG

  DOI：——

  日期：——
• SHAO, QIU-YI;GAO, XIANG;SHUN, PEI-DONG, YUTSZI XUASYUEH, 11,(1991) N, S. 195-198
  作者：SHAO, QIU-YI、GAO, XIANG、SHUN, PEI-DONG

  DOI：——

  日期：——