α-phenyl-3-quinolinemethanol | 1375064-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: α-phenyl-3-quinolinemethanol
• 英文别名: phenyl(3-quinolinyl)methanol；3-quinolinyl-phenylmethanol；(Phenyl)(3-quinolyl)methanol；phenyl(quinolin-3-yl)methanol
• CAS: 1375064-64-4
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: XMNFKVLKFQTJCA-UHFFFAOYSA-N

物化性质

• 沸点：
  387.2±32.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  α-(2-bromophenyl)-3-quinolinemethanol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以50%的产率得到α-phenyl-3-quinolinemethanol
  参考文献：
  名称：

  喹啉的分子内自由基加成

  摘要：

  本文涉及喹啉的分子内自由基加成。已证明向喹啉的C-2，C-3和C-4自由基加成均在中性条件下进行。在每种情况下，都观察到形成了杂芳族产物而不是二氢喹啉（暗示了所谓的氧化锡氢化物途径）。

  DOI：

  10.1016/s0040-4039(01)00321-5

文献信息

• Intramolecular radical additions to quinolines
  作者：David C Harrowven、Benjamin J Sutton、Steven Coulton

  DOI：10.1016/s0040-4039(01)00321-5

  日期：2001.4

  This paper is concerned with intramolecular radical additions to quinolines. Radical additions to C-2, C-3 and C-4 of a quinoline have all been shown to proceed under neutral conditions. In each case formation of heteroaromatic products, rather than dihydroquinolines, was observed (implicating the so called oxidative tin hydride pathway).

  本文涉及喹啉的分子内自由基加成。已证明向喹啉的C-2，C-3和C-4自由基加成均在中性条件下进行。在每种情况下，都观察到形成了杂芳族产物而不是二氢喹啉（暗示了所谓的氧化锡氢化物途径）。
• Efficient 1,2-Addition of Aryl- and Alkenylboronic Acids to Aldehydes Catalyzed by the Palladium/Thioether−Imidazolinium Chloride System
  作者：Masami Kuriyama、Rumiko Shimazawa、Ryuichi Shirai

  DOI：10.1021/jo7020983

  日期：2008.2.1

  [GRAPHICS]The high level of catalyst performance was attainable in the palladium-catalyzed 1,2-addition of aryl-, heteroaryl-, and alkenylboronic acids to aromatic, heteroaromatic, and aliphatic aldehydes using thioether-imidazolinium chloride L5 as a heterobidentate carbene ligand precursor.
• Synthesis and reactivity of lithium tri(quinolinyl)magnesates
  作者：Sylvain Dumouchel、Florence Mongin、François Trécourt、Guy Quéguiner

  DOI：10.1016/j.tet.2003.06.001

  日期：2003.10

  2-, 3- and 4-Bromoquinolines, were converted to the corresponding lithium tri(quinolinyl)magnesates at -10degreesC when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines. (C) 2003 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed 1,2-Addition of Potassium Aryl- and Alkenyltrifluoroborates to Aldehydes using Thioether−Imidazolinium Carbene Ligands
  作者：Masami Kuriyama、Rumiko Shimazawa、Terumichi Enomoto、Ryuichi Shirai

  DOI：10.1021/jo801352h

  日期：2008.9.1

  Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether-imidazolinium carbene ligands proceeded readily under aqueous conditions. This process tolerated a diverse range of potassium trifluoroborate salts and aldehydes, giving a variety of carbinol derivatives with good to excellent yields.
• Tributylmagnesium ate complex-mediated bromine–magnesium exchange of bromoquinolines: a convenient access to functionalized quinolines
  作者：S DUMOUCHEL、F MONGIN、F TRECOURT、G QUEGUINER

  DOI：10.1016/s0040-4039(03)00183-7

  日期：2003.3.3

  2-, 3- and 4-bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10degreesC by treatment with Bu3MgLi in THF or toluene. The resulting organomagnesium derivatives were quenched by various electrophiles to afford functionalized quinolines. (C) 2003 Elsevier Science Ltd. All rights reserved.