(2-(pent-1-yn-1-yl)phenyl)methanol

• 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: (2-(pent-1-yn-1-yl)phenyl)methanol
• 英文别名: 2-pent-1-ynylbenzyl alcohol；(2-Pent-1-ynylphenyl)methanol；(2-pent-1-ynylphenyl)methanol
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: SBLPOFSBASCEQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (2-(pent-1-yn-1-yl)phenyl)methanol 在 吡啶 、 三溴化磷 作用下， 以 氯仿 为溶剂， 以79%的产率得到2-pent-1-ynylbenzyl bromide
  参考文献：
  名称：

  串联吲哚CH烯基化/芳基化反应，用于四取代烯烃的合成。

  摘要：

  炔基吲哚经历了Pd催化的吲哚CH活化/炔烃碳钯/芳基化的新序列，其中二芳基碘鎓盐提供了芳基组分。已经以良好至优异的产率制备了一系列官能化的吲哚烯烃，其中该反应对Z-烯烃是选择性的。

  DOI：

  10.1039/c1cc13094c
• 作为产物：
  描述：

  1-戊炔 、 2-碘苄醇 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 甲苯 为溶剂， 生成 (2-(pent-1-yn-1-yl)phenyl)methanol
  参考文献：
  名称：

  环丁烷酮和炔烃之间的分子内“剪切和缝合”反应融合环形成

  摘要：

  本文描述了在环丁酮和炔烃之间进行分子内“切割和缝合”催化转化以构建环己烯酮稠合环的过程。挑战来自在空间上受阻较大的近端位置进行选择性偶联的需求，可以通过使用富含电子但体积较小的膦配体来解决。对照实验和13 C标记研究表明，该反应可能始于裂解环丁烯酮受阻较少的远端C-C键，然后脱羰和CO重新插入以使Rh插入受阻较近的位置开始。

  DOI：

  10.1002/anie.201712487

文献信息

• Palladium and copper catalyzed Sonogashira decarboxylative coupling of aryl iodides and alkynyl carboxylic acids
  作者：Carine Maaliki、Yoan Chevalier、Emilie Thiery、Jérôme Thibonnet

  DOI：10.1016/j.tetlet.2016.06.073

  日期：2016.7

  A mild procedure of palladium and copper catalyzed decarboxylative cross-coupling reaction of aryl halides and alkynyl carboxylic acids has been developed. Low molecular weight acids, to introduce small building blocks, were specifically used. This methodology is easy to implement and uses common reactants and catalysts.

  已经开发了温和的钯和铜催化的芳基卤化物和炔基羧酸的脱羧交叉偶联反应的方法。特别引入了低分子量的酸，以引入小的结构单元。该方法易于实施，并使用常见的反应物和催化剂。
• Intramolecular Alkyne Hydroalkoxylation and Hydroamination Catalyzed by Iridium Hydrides
  作者：Xingwei Li、Anthony R. Chianese、Tiffany Vogel、Robert H. Crabtree

  DOI：10.1021/ol052186i

  日期：2005.11.1

  [reaction: see text] Iridium(III) hydrides prove to be air-stable active catalysts for intramolecular hydroalkoxylation and hydroamination of internal alkynes with proximate nucleophiles. The cyclization follows highly selective 6-endo-dig regiochemistry when regioselectivity is an issue.

  [反应：见正文]氢化铱（III）被证明是空气稳定的活性催化剂，用于分子内加氢烷氧基化和内部炔烃与近亲核试剂的加氢胺化反应。当区域选择性成为一个问题时，环化反应遵循高度选择性的6-endo-dig区域化学。
• Triaryl-Like MONO-, BIS-, and TRISKITPHOS Phosphines: Synthesis, Solution NMR Studies, and a Comparison in Gold-Catalyzed Carbon–Heteroatom Bond Forming 5-<i>exo</i>-dig and 6-<i>endo</i>-dig Cyclizations
  作者：Simon Doherty、Julian G. Knight、Daniel O. Perry、Nicholas A. B. Ward、Dror M. Bittner、William McFarlane、Corinne Wills、Michael R. Probert

  DOI：10.1021/acs.organomet.6b00146

  日期：2016.5.9

  A homologous series of triaryl-like KITPHOS-type monophosphines containing one, two, or three bulky 12-phenyl-9,10-dihydro-9,10-ethenoanthracene (KITPHOS) units have been developed, and the influence of increasing steric bulk on their efficacy as ligands in gold(I)-catalyzed carbon-heteroatom bond-forming cyclizations has been investigated. Detailed solution NMR studies on Ph-TRISKITPHOS, its oxide, and the corresponding gold(I) chloride adduct identified a conformational exchange process involving a concerted librational motion of the individual anthracene-derived organic substituents about their P-C bonds. The cessation of this motion at reduced temperatures lowers the molecular symmetry such that the two C6H4 rings in each of the KITPHOS units become inequivalent; a lower energy process involving restricted rotation of the biaryl-like phenyl ring has also been identified. Electrophilic gold(I) complexes of these triaryl-like KITPHOS monophosphines catalyze the 5-exo-dig cycloisomerization of propargyl amides to afford the corresponding methylene oxazolines, which were used in a subsequent tandem carbonyl-ene reaction to afford functionalized 2 -substituted oxazolines. A comparative survey revealed that catalyst efficiency for cycloisomerization decreases in the order MONOKITPHOS = BISKITPHOS > PPh3 > TRISKITPHOS. The optimum system also catalyzes the selective 6-endo-dig cyclization of 2-alkynylbenzyl alcohols, 2-alkynylbenzoic acid, and 2-phenylethynyl benzamides; gratifyingly, in several cases the yields obtained are markedly higher and/or reaction times significantly shorter than those previously reported for related gold catalysts. Moreover, these are the first examples of gold(I)-catalyzed 6-endo-dig cycloisomerizations involving 2-phenylethynyl benzamides and, reassuringly, the optimum gold(I)/MONOKITPHOS systems either rivaled or outperformed existing silver or palladium based catalysts. The steric parameters of this homologous series of phosphines have been quantified and compared with selected triarylphosphines using a combination of Solid -G calculations, to determine the percentage of the metal coordination sphere shielded by the phosphine (the G parameter), and Salerno molecular buried volume calculations (SambVca) to determine the percent buried volume (%V-bur); the corresponding Tolman cone angles have also been determined from correlations.
• Gold-Catalyzed Benzylic CH Activation at Room Temperature
  作者：A. Stephen K. Hashmi、Sascha Schäfer、Michael Wölfle、Cesar Diez Gil、Peter Fischer、Antonio Laguna、M. Carmen Blanco、M. Concepción Gimeno

  DOI：10.1002/anie.200701521

  日期：2007.8.13