1-(5-chloro-2-nitrophenyl)-3-phenylprop-2-yn-1-ol | 1072913-31-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(5-chloro-2-nitrophenyl)-3-phenylprop-2-yn-1-ol
• CAS: 1072913-31-5
• 化学式: C₁₅H₁₀ClNO₃
• 分子量: 287.702
• InChiKey: AUNTZHHJJJFUQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2-丁酮酸乙酯 、 1-(5-chloro-2-nitrophenyl)-3-phenylprop-2-yn-1-ol 在 iron(III) chloride 、 tin(II) chloride dihdyrate 作用下， 以 氯苯 为溶剂， 反应 12.0h， 以63%的产率得到ethyl 6-chloro-2-methyl-4-(phenylethynyl)quinoline-3-carboxylate
  参考文献：
  名称：

  Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/ Propargylation−Cyclization

  摘要：

  Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.

  DOI：

  10.1021/jo8017654
• 作为产物：
  描述：

  5-氯-2-硝基苯甲醛 、 苯乙炔 在 正丁基锂 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1-(5-chloro-2-nitrophenyl)-3-phenylprop-2-yn-1-ol
  参考文献：
  名称：

  Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/ Propargylation−Cyclization

  摘要：

  Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.

  DOI：

  10.1021/jo8017654

文献信息

• Spontaneous resolution upon crystallization of allenyl-bis-phosphine oxides
  作者：G. Gangadhararao、R. N. Prasad Tulichala、K. C. Kumara Swamy

  DOI：10.1039/c5cc00232j

  日期：——

  The first example of ‘spontaneous resolution by crystallization’ in allene chemistry, by means of crystal structures and solid state CD spectra of the R and S enantiomers, is presented.

  在所有烯烃化学中，通过晶体结构和固态CD光谱展示了第一个关于“结晶自发分辨”的例子，包括R和S对映体。
• Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/ Propargylation−Cyclization
  作者：Jinmin Fan、Changfeng Wan、Gaojun Sun、Zhiyong Wang

  DOI：10.1021/jo8017654

  日期：2008.11.7

  Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.