1-[4-(2-(1-羟基环己基)乙炔基)苯基]乙酮 | 853782-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[4-(2-(1-羟基环己基)乙炔基)苯基]乙酮
• 英文名称: 1-[4-(2-(1-hydroxycyclohexyl)ethynyl)phenyl]ethanone
• 英文别名: 1-[4-(1'-hydroxy-cyclohexylethynyl)-phenyl]ethanone；1-(4'-acetylphenyl)ethynylcyclohexan-1-ol；1-(4-acetylphenylethynyl)cyclohexanol；1-[4-[2-(1-Hydroxycyclohexyl)ethynyl]phenyl]ethanone
• CAS: 853782-97-5
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: LFEQJORNUASFHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  410.7±30.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(2-(1-羟基环己基)乙炔基)苯基]乙酮 、 4-碘苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二异丙胺 作用下， 以33%的产率得到1-(4-((4-methoxyphenyl)ethynyl)phenyl)ethanone
  参考文献：
  名称：

  Ethynyl-cyclohexanol: an efficient acetylene surrogate in Sonogashira coupling

  摘要：

  The Sonogashira coupling of aryl halides in the presence of 1-ethynyl-cyclohexanol as an acetylene source provides an efficient method for the synthesis of diarylacetylenes without the isolation of the appropriate arylacetylenes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.031
• 作为产物：
  描述：

  4-碘代苯乙酮 、 炔环己醇 在 四氢吡咯 作用下， 以 水 为溶剂， 反应 14.0h， 以92%的产率得到1-[4-(2-(1-羟基环己基)乙炔基)苯基]乙酮
  参考文献：
  名称：

  Alkynylation of aryl halides with perfluoro-tagged palladium nanoparticles immobilized on silica gel under aerobic, copper- and phosphine-free conditions in water

  摘要：

  描述了通过氟-氟相互作用将全氟标记的钯纳米粒子固定在氟化硅胶上（Pdnp-A/FSG），或通过共价键链接到硅胶上（Pdnp-B），在水中以有氧、无铜和无膦条件下实现末端炔烃与芳基卤化物的炔化反应，以及其回收和再利用。

  DOI：

  10.1039/b903233a

文献信息

• Perfluoro-tagged, phosphine-free palladium nanoparticles supported on silica gel: application to alkynylation of aryl halides, Suzuki–Miyaura cross-coupling, and Heck reactions under aerobic conditions
  作者：Roberta Bernini、Sandro Cacchi、Giancarlo Fabrizi、Giovanni Forte、Francesco Petrucci、Alessandro Prastaro、Sandra Niembro、Alexandr Shafir、Adelina Vallribera

  DOI：10.1039/b915465e

  日期：——

  cross-coupling, as well as in the Heck reaction between methyl acrylate and aryl iodides is described. The reactions are carried out under aerobic and phosphine-free conditions with excellent to quantitative product yields in each case. The catalysts are easily recovered and reused several times without significant loss of activity. The alkynylation of aryl halides (under copper-free conditions) and the Suzuki–Miyaura

  的利用 全氟标记的 钯纳米粒子通过氟-氟相互作用（Pd np - A / FSG）或通过芳基卤化物的炔基化，铃木-宫浦交叉偶联以及与硅胶（Pd np - B）的共价键固定在氟硅胶上在里面赫克反应 之间 丙烯酸甲酯描述了芳基碘化物。反应在有氧条件下进行膦在每种情况下均具有无与伦比的条件，具有极好的定量产品产量。这催化剂可以轻松恢复并重复使用几次，而不会造成大量活动损失。芳基卤化物的炔基化（在铜自由条件）和铃木-宫浦的交叉耦合是在 水。这赫克反应 的 丙烯酸甲酯 芳基碘化物最好在 机械化。也有报道称Pd np – B在由2-（炔基）三氟乙酰苯胺和芳基卤化物合成2，3-二取代的吲哚中的应用。
• Efficient copper-free Sonogashira coupling of aryl chlorides with palladium on charcoal
  作者：Anna Komáromi、Zoltán Novák

  DOI：10.1039/b810928a

  日期：——

  Palladium on charcoal serves as an efficient and reusable solid supported catalyst for the Sonogashira coupling of aryl chlorides with terminal acetylenes in the presence of a bulky, electron-rich biphenyl type ligand (XPhos), without copper co-catalyst.

  活性炭负载钯作为高效且可重复使用的固载催化剂，在无铜共催化剂存在下，通过体积庞大、电子丰富的联苯型配体（XPhos）促进芳基氯与末端炔烃的Sonogashira偶联反应。
• Copper- and Ligand-Free Sonogashira Reaction Catalyzed by Pd(0) Nanoparticles at Ambient Conditions under Ultrasound Irradiation
  作者：Atul R. Gholap、K. Venkatesan、Renu Pasricha、Thomas Daniel、Rajgopal J. Lahoti、Kumar V. Srinivasan

  DOI：10.1021/jo0503815

  日期：2005.6.1

  The Sonogashira reaction proceeds at ambient temperature (30 degrees C) in acetone or room-temperature ionic liquid, 1,3-di-n-butylimidazolium tetrafluoroborate ([bbim]BF4), as solvent under ultrasound irradiation to give enhanced reaction rates, excellent chemoselectivity, and high yields in the absence of a copper cocatalyst and a phosphine ligand. TEM analysis showed the formation of stable, crystalline, and polydispersed Pd(0) nanoparticles as catalyst for the reaction.
• Copper- and Phosphine-Free<i>Sonogashira</i>Coupling Reaction Catalyzed by Polyurea-Encapsulated Palladi­um(II)
  作者：Yun-Yan Kuang、Fen-Er Chen

  DOI：10.1002/hlca.200800385

  日期：2009.5

  Abstractmagnified imageA polyurea‐encapsulated palladium catalyst (Pd EnCatTM 30) was first applied to Sonogashira cross‐coupling reactions in the absence of a copper salt co‐catalyst and under phosphine‐free conditions. This polymer‐anchored homogeneous palladium catalyst efficiently catalyzed the Sonogashira reaction of various iodoarenes with terminal alkynes in H2O/MeCN, and good yields were obtained at 40° after 3–7 h in the presence of piperidine. Moreover, this catalyst maintains its efficiency through three recycle runs.