2-phenyl-hex-5-yn-3-ol | 78808-40-9

• 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-phenyl-hex-5-yn-3-ol
• 英文别名: 2-Phenylhex-5-yn-3-ol
• CAS: 78808-40-9
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: JYWNDFNWLADDFN-UHFFFAOYSA-N

物化性质

• 沸点：
  291.3±28.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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

• 作为产物：
  描述：

  2-苯基-1,2-环氧丙烷 、 3-溴丙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 tin(II) trifluoromethanesulfonate lithium hydroxide 、 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 以43%的产率得到2-phenyl-hex-5-yn-3-ol
  参考文献：
  名称：

  Tuning the reactivity of organotin(IV) by LiOH: allylation and propargylation of epoxides via redox transmetalation

  摘要：

  In presence of catalytic Pd(0) or Pt(II), a reagent combination of SnCl2-LiOH promotes the reaction of organic halides and epoxides in dichloromethane leading to the regioselective formation of corresponding homoallyl and homopropargyl alcohols in good yields. This 2-carbon extension strategy adds to the repertoire of Barbier reactions via metal salts and reinforces views on the enhanced reactivity of organotin having -OH pendant. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.12.008

文献信息

• Synthesis, characterization of active Sn(0), and its application in selective propargylation of aldehyde at room temperature in water
  作者：Paresh Nath Chatterjee、Dipankar Paul、Micky Lanster Sawkmie、Arun Kumar Sinha、Snehadrinarayan Khatua

  DOI：10.1139/cjc-2017-0745

  日期：2019.1

  synthesized in high yields by the chemical reduction of the blue–black stannous oxide using freshly prepared sodium stannite solution as reducing agent at 40 °C and 60 °C. The Sn(0) particles are characterized using powder XRD, SEM, and DSC. The as-synthesized Sn(0) particles are applied as reagent for the regioselective synthesis of homopropargyl alcohols from propargyl bromide and aldehydes in distilled water

  在 40 °C 和 60 °C 下，使用新鲜制备的亚锡酸钠溶液作为还原剂，通过化学还原蓝黑色氧化亚锡，以高产率合成活性 Sn(0) 颗粒。使用粉末 XRD、SEM 和 DSC 对 Sn(0) 颗粒进行表征。合成的 Sn(0) 颗粒用作试剂，用于在室温下在蒸馏水中由炔丙基溴和醛类区域选择性合成高炔丙基醇（产率 50%–84%）。该反应不需要热、微波、超声波、有机助溶剂、助试剂或惰性气氛的帮助。与其他亲电性较低的羰基官能团（如酮、酰胺和羧酸）相比，炔丙基化反应对醛具有高度化学选择性。
• A CONVENIENT SYNTHESIS OF α-HYDROXYALLENES BY THE REACTION OF PROPARGYL IODIDES WITH ALDEHYDES IN THE PRESENCE OF STANNOUS HALIDE
  作者：Teruaki Mukaiyama、Taira Harada

  DOI：10.1246/cl.1981.621

  日期：1981.5.5

  In the presence of stannous halide, propargyl iodides react with aldehydes in an aprotic solvent to yield α-hydroxyallenes as major products, particularly in the cases of γ-substituted propargyl iodides, along with β-hydroxyacetylenes.

  在卤化亚锡存在下，炔丙基碘与醛在非质子溶剂中反应，生成 α-羟基丙二烯作为主要产物，特别是在 γ-取代的炔丙基碘和 β-羟基乙炔的情况下。
• Carbonyl Propargylation and Allenylation with 2-Propynyl Mesylates, Tin(IV) Iodide, and Tetrabutylammonium Iodide Controlled by Either a Steric Effect or Coordination Effect
  作者：Yoshiro Masuyama、Ryouichi Yamazuki、Masaru Ohtsuka、Yasuhiko Kurusu

  DOI：10.1055/s-2006-944222

  日期：2006.7

  A combination of tin(IV) iodide and tetrabutylammonium iodide can be used for propargylation or allenylation of aldehydes with 2-propynyl mesylates in dichloromethane. 1-Methyl-2-propynyl mesylate or 2-butynyl mesylate results in propargylation or allenylation controlled by the steric effect of the 1- or 3-methyl group, and 3-trimethylsilyl-2-propynyl mesylate results in propargylation controlled by the coordination of triiodostannate to silane.

  碘化锡(IV)和碘化四丁基铵的组合可用于在二氯甲烷中用甲磺酸2-丙炔酯进行醛的炔丙基化或丙烯基化。 1-甲基-2-丙炔基甲磺酸酯或2-丁炔基甲磺酸酯导致由1-或3-甲基的空间效应控制的炔丙基化或联烯基化，而3-三甲基甲硅烷基-2-丙炔基甲磺酸酯导致由配位控制的炔丙基化。三碘锡酸盐转化为硅烷。
• Highly efficient water promoted allylation and propargylation of arylepoxides via rearrangement-carbonyl addition
  作者：Ujjal Kanti Roy、Sujit Roy

  DOI：10.1016/j.tet.2005.10.005

  日期：2006.1

  A simple and highly efficient one-pot procedure for allylation and propargylation of arylepoxides has been developed. A combination of SnCl2 and catalytic Pd(0) or Pd(II) promotes the reaction of organic halides and epoxides in DMSO with controlled water addition, leading to the regioselective formation of the corresponding homoallyl and homopropargyl alcohols in good yields. (c) 2005 Elsevier Ltd. All rights reserved.
• MUKAIYAMA TERUAKI; HARADA TAIRA, CHEM. LETT., 1981, NO 5, 621-624
  作者：MUKAIYAMA TERUAKI、 HARADA TAIRA

  DOI：——

  日期：——