6-(2-Ethynylphenyl)-5-hexyn-2-ol | 159306-05-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-(2-Ethynylphenyl)-5-hexyn-2-ol
• 英文别名: 6-(2-ethynylphenyl)hex-5-yn-2-ol
• CAS: 159306-05-5
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: UCKJJUQPUXQXER-UHFFFAOYSA-N

物化性质

• 沸点：
  348.3±27.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(2-Ethynylphenyl)-5-hexyn-2-ol 在 1,4-环己二烯 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 10.0h， 生成 4-(naphthalen-2-yl)butan-2-one
  参考文献：
  名称：

  Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

  摘要：

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.

  DOI：

  10.1021/jo00104a053
• 作为产物：
  描述：

  1,2-二碘苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 6-(2-Ethynylphenyl)-5-hexyn-2-ol
  参考文献：
  名称：

  Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

  摘要：

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.

  DOI：

  10.1021/jo00104a053

文献信息

• Dual Gold-Catalyzed Three-Component Reaction: Efficient Synthesis of Indene-Fused Esters, Acids, and Lactones through Gold Vinylidene Intermediates
  作者：Congjun Yu、Xiaodong Ma、Bin Chen、Bencan Tang、Robert S. Paton、Guozhu Zhang

  DOI：10.1002/ejoc.201700084

  日期：2017.3.17

  A dual gold(I)‐catalyzed three‐component reaction is developed to prepare indene‐fused carboxylic acid derivatives from diynes, alcohols, and pyridine N‐oxides in both inter‐ and intramolecular fashions. Pyridine N‐oxides exhibit unique reactivity and selectivity to oxidize the gold vinylidene. Experimental studies and DFT calculations support ketene formation as the key step.

  开发了一种双金（I）催化的三组分反应，以分子间和分子内方式由二炔，醇和吡啶N-氧化物制备茚稠合的羧酸衍生物。吡啶N-氧化物具有独特的反应性和选择性，可以氧化亚乙烯基金。实验研究和DFT计算支持乙烯酮的形成为关键步骤。