1-(4-氯苯基)壬-2-炔-1-酮 | 603129-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-氯苯基)壬-2-炔-1-酮
• 英文名称: 1-(4-chlorophenyl)-2-nonyn-1-one
• 英文别名: 2-Nonyn-1-one, 1-(4-chlorophenyl)-；1-(4-chlorophenyl)non-2-yn-1-one
• CAS: 603129-04-0
• 化学式: C₁₅H₁₇ClO
• 分子量: 248.752
• InChiKey: JKTSTUWBZJQFNV-UHFFFAOYSA-N

物化性质

• 沸点：
  358.9±44.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)壬-2-炔-1-酮 在 JandaJel resin-supported Ph₃P 作用下， 反应 12.0h， 以72%的产率得到(E,E)-1-(4-chlorophenyl)-nona-2,4-dien-1-one
  参考文献：
  名称：

  Solvent-free heterogeneous organocatalysis: stereoselective isomerization of α,β-ynones to (E,E)-α,β-γ,δ-dienones catalyzed by polymer-supported tertiaryphosphines

  摘要：

  Stereoselective isomerization of alpha, beta-ynones was catalyzed by polymer-supported tertiaryphosphines under solvent-free conditions. (E, E)-alpha, beta-gamma, delta-Dienones were obtained with up to 93% isolated yields when JJ-TPP was employed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.093
• 作为产物：
  描述：

  1-辛炔 、 4-氯苯甲酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以78%的产率得到1-(4-氯苯基)壬-2-炔-1-酮
  参考文献：
  名称：

  聚苯乙烯负载的溴化锌-乙二胺配合物是可重复使用且高效的多相催化剂，用于合成α，β-乙炔酮

  摘要：

  聚苯乙烯负载的溴化锌-乙二胺络合物已显示出可作为可循环利用的非均相催化剂，用于通过酰基氯与末端炔烃的交叉偶联快速有效地合成α，β-炔酮。该催化剂在反应条件下易于制备，稳定，可重复使用和有效。 多相催化-交叉偶联-酰氯-炔烃-酮

  DOI：

  10.1055/s-0030-1258365

文献信息

• Aqueous Ammonia as a New Activator for Sonogashira Coupling
  作者：Mohamed S. Mohamed Ahmed、Akitoshi Sekiguchi、Kentaro Masui、Atsunori Mori

  DOI：10.1246/bcsj.78.160

  日期：2005.1

  Sonogashira coupling, which is a coupling reaction of terminal alkynes with organic halides, takes place with dilute aqueous ammonia as an activator. The reaction of several terminal alkynes and aryl iodides in the presence of small excess of aqueous ammonia at room temperature furnishes the cross-coupling product in good-to-excellent yields. A water-soluble amine with a high boiling point is alternatively employed for reactions at higher temperatures. A related coupling reaction in the presence of carbon monoxide also proceeded at room temperature and under ambient pressure to afford α,β-alkynyl ketones efficiently.

  Sonogashira偶联反应，是一种端炔与有机卤化物的偶联反应，在稀释的氨水溶液中作为活化剂的情况下进行。在室温下，少量过量的氨水存在时，几种端炔与芳基碘的反应能以良好的至极佳的产率得到交叉偶联产物。另一种选择是在较高温度下的反应中使用高沸点的水溶性胺。类似的在二氧化碳存在下的偶联反应也能在室温和常压下高效地进行，生成α,β-炔基酮。
• Photoinduced Synthesis of<i>P</i>-Perfluoroalkylated Phosphines from Triarylphosphines and Their Application in the Copper-Free Cross-Coupling of Acid Chlorides and Terminal Alkynes
  作者：Shin-ichi Kawaguchi、Yoshiaki Minamida、Takumi Okuda、Yuki Sato、Tomokazu Saeki、Aya Yoshimura、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1002/adsc.201500294

  日期：2015.8.10

  P‐perfluoroalkylated phosphines from triarylphosphines and perfluoroalkyl iodides has been developed. The photoinduced reaction involves the substitution of aryl groups on the phosphorus atom with perfluoroalkyl groups to successfully afford P‐perfluoroalkylated phosphines. In addition, the P‐perfluoroalkylated phosphines were found to promote the Cu‐free cross‐coupling reaction of acid chlorides with terminal

  已开发出一种实用的合成方法，该方法可从三芳基膦和全氟烷基碘化物生成P-全氟烷基化膦。光诱导反应涉及用全氟烷基取代磷原子上的芳基，从而成功制得P-全氟烷基化的膦。此外，发现P-全氟烷基化的膦可促进酰基氯与末端炔烃的无Cu交叉偶联反应。
• Pd-catalyzed coupling reaction of acid chlorides with terminal alkynes using 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene ligand
  作者：Shingo Atobe、Haruna Masuno、Motohiro Sonoda、Yuki Suzuki、Hiroyuki Shinohara、Satoshi Shibata、Akiya Ogawa

  DOI：10.1016/j.tetlet.2012.01.105

  日期：2012.4

  In the presence of 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene as a ligand, the direct synthesis of alkynones has accomplished by a Pd-catalyzed coupling reaction of acid chlorides with terminal acetylenes under mild conditions.

  在1-（2-吡啶基乙炔基）-2-（2-噻吩基乙炔基）苯作为配体的存在下，炔烃的直接合成是通过在温和的条件下，Pd催化酰氯与末端乙炔的偶联反应而完成的。
• A phosphine-free heterogeneous coupling of acyl chlorides with terminal alkynes catalyzed by an MCM-41-immobilized palladium complex
  作者：Bin Huang、Lin Yin、Mingzhong Cai

  DOI：10.1039/c3nj00425b

  日期：——

  The phosphine-free heterogeneous coupling of acyl chlorides with terminal alkynes was achieved in triethylamine at 50 °C in the presence of a 0.2 mol% 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium complex [MCM-41-2N-Pd(OAc)2], yielding a variety of ynones in good to excellent yields. This novel heterogeneous palladium catalyst can be conveniently prepared from commercially

  酰基氯与末端炔烃的无膦非均相偶联是在 三乙胺在50°C下，在0.2 mol％3-（2-氨基乙基氨基）丙基官能化的MCM-41固定的钯配合物[MCM-41-2N-Pd（OAc）2 ]的存在下，生成多种良好的炔酮达到优异的产量。这种新型的多相钯催化剂可以方便地由市售的廉价试剂制备，并通过简单过滤反应溶液进行再循环，并用于至少10次连续试验而活性没有降低。我们的系统不仅避免使用膦配体，而且解决了钯催化剂回收和再利用的基本问题。
• Using Pd–salen complex as an efficient catalyst for the copper- and solvent-free coupling of acyl chlorides with terminal alkynes under aerobic conditions
  作者：Mohammad Bakherad、Amir Hossein Amin、Ali Keivanloo、Bahram Bahramian、Mersad Raessi

  DOI：10.1016/j.cclet.2010.01.010

  日期：2010.6

  palladium(II) N,N′-bis[5-(triphenylphosphonium)-methyl]salicylidene}-1,2-ethanediamine chloride was found to be a highly active catalyst for the copper- and solvent-free coupling reaction of terminal alkynes with different acyl chlorides in the presence of triethylamine as base, giving excellent ynones under aerobic conditions.

  摘要发现钯-salen络合物钯（II）N，N'-双[5-（三苯基-）-甲基]水杨亚基} -1，2-乙二胺氯化物是铜和溶剂-的高活性催化剂。在三乙胺作为碱的存在下，末端炔烃与不同的酰氯的自由偶联反应，在有氧条件下提供了出色的炔酮。