3-bromo-1-(but-2-ynyl)benzene | 411242-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-1-(but-2-ynyl)benzene
• 英文别名: O-(2-butynyl)-3-bromophenol；Uojihxhufoqoqj-uhfffaoysa-；1-bromo-3-but-2-ynoxybenzene
• CAS: 411242-54-1
• 化学式: C₁₀H₉BrO
• 分子量: 225.085
• InChiKey: UOJIHXHUFOQOQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(but-2-ynyl)benzene 在 盐酸 、 甲醇 、 叔丁基锂 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 177.5h， 生成 3-[3-(butyn-2-yloxy)phenyl]propanal
  参考文献：
  名称：

  Doetz, K. H.; Mittenzwey, S., European Journal of Organic Chemistry, 2002, # 1, p. 39 - 48

  摘要：

  DOI：
• 作为产物：
  描述：

  间溴苯酚 、 but-2-yn-1-yl methanesulfonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以99%的产率得到3-bromo-1-(but-2-ynyl)benzene
  参考文献：
  名称：

  Pt^IV-Catalyzed Cyclization of Arene−Alkyne Substrates via Intramolecular Electrophilic Hydroarylation

  摘要：

  [GRAPHICS]We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.

  DOI：

  10.1021/ol034177k

文献信息

• Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalization
  作者：Stefan J Pastine、So Won Youn、Dalibor Sames

  DOI：10.1016/j.tet.2003.05.003

  日期：2003.11

  We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.

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