p-Nitrophenyl-1-methylpropargylether | 33143-86-1

• 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: p-Nitrophenyl-1-methylpropargylether
• 英文别名: 1-[(1-methyl-2-propynyl)oxy]-4-nitro-benzene；1-but-3-yn-2-yloxy-4-nitrobenzene
• CAS: 33143-86-1
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: YRUKDXJQRRQKEL-UHFFFAOYSA-N

物化性质

• 沸点：
  317.0±22.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  p-Nitrophenyl-1-methylpropargylether 、 methyl 2-(bromomethyl)-3-phenylacrylate 在 copper(l) iodide 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以65%的产率得到
  参考文献：
  名称：

  Controlled synthesis of 1-vinylnaphthalenes versus (E)-α-(1,3-enyn-4-yl)-α,β-unsaturated esters from Morita–Baylis–Hillman bromides: a sequential alkynylation and competitive 6π-electrocyclization versus conjugative transposition of a triple bond

  摘要：

  An expedient controlled synthesis of 1-vinylnaphthalenes and various dienyne derivatives has been carried out from the Morita-Baylis-Hillman bromides and propargyl acetate or p-nitrophenyl propargyl ether. By judicious choice of base, reaction temperature, and leaving group, a selective synthesis of 1-vinylnaphthalenes and dienynes, (E)-alpha-(1,3-enyn-4-yl)-alpha,beta-unsaturated esters, could be performed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.007
• 作为产物：
  描述：

  对硝基苯酚 、 3-丁炔-2-醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以68%的产率得到p-Nitrophenyl-1-methylpropargylether
  参考文献：
  名称：

  Controlled synthesis of 1-vinylnaphthalenes versus (E)-α-(1,3-enyn-4-yl)-α,β-unsaturated esters from Morita–Baylis–Hillman bromides: a sequential alkynylation and competitive 6π-electrocyclization versus conjugative transposition of a triple bond

  摘要：

  An expedient controlled synthesis of 1-vinylnaphthalenes and various dienyne derivatives has been carried out from the Morita-Baylis-Hillman bromides and propargyl acetate or p-nitrophenyl propargyl ether. By judicious choice of base, reaction temperature, and leaving group, a selective synthesis of 1-vinylnaphthalenes and dienynes, (E)-alpha-(1,3-enyn-4-yl)-alpha,beta-unsaturated esters, could be performed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.007

文献信息

• Controlled synthesis of 1-vinylnaphthalenes versus (E)-α-(1,3-enyn-4-yl)-α,β-unsaturated esters from Morita–Baylis–Hillman bromides: a sequential alkynylation and competitive 6π-electrocyclization versus conjugative transposition of a triple bond
  作者：Jin Woo Lim、Ko Hoon Kim、Se Hee Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2013.03.007

  日期：2013.5

  An expedient controlled synthesis of 1-vinylnaphthalenes and various dienyne derivatives has been carried out from the Morita-Baylis-Hillman bromides and propargyl acetate or p-nitrophenyl propargyl ether. By judicious choice of base, reaction temperature, and leaving group, a selective synthesis of 1-vinylnaphthalenes and dienynes, (E)-alpha-(1,3-enyn-4-yl)-alpha,beta-unsaturated esters, could be performed. (C) 2013 Elsevier Ltd. All rights reserved.