1-phenylprop-1-en-1-yl trifluoromethanesulfonate

• 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: 1-phenylprop-1-en-1-yl trifluoromethanesulfonate
• 英文别名: (Z)-1-Phenylpropen-1-yl triflate；[(Z)-1-phenylprop-1-enyl] trifluoromethanesulfonate
• 化学式: C₁₀H₉F₃O₃S
• 分子量: 266.241
• InChiKey: ZPWSRHZLIGENIN-MBXJOHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 (Z)-tert-butyldimethyl((1-phenylprop-1-en-1-yl)oxy)silane 在 cesium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 以78%的产率得到1-phenylprop-1-en-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  通过四组分偶联和四环化步骤分四步全合成 (+)-α-Onocerin

  摘要：

  结构独特的 C2 对称四环三萜 (+)-α-橙黄素 (1) 的对映选择性合成非常短（四步，总产率为 31%）。这种机制的简洁性取决于四个片段（两个手性环氧酮分子和两个乙烯基锂分子）的组装以一步生成手性双环氧化物 4，以及所有四个碳环在一个步骤中的有效形成逐步进行阳离子-烯烃四环化。在 1 的合成中也使用了将乙烯基叔丁基二甲基甲硅烷基醚转化为乙烯基三氟甲磺酸酯的新通用方法，同时保留了 E 或 Z 烯烃几何结构。还描述了 1 的非 C2 对称非对映异构体的短对映选择性合成它使用了新的方法论。

  DOI：

  10.1021/ja027373f

文献信息

• Copper-Catalyzed Regioselective Reaction of Internal Alkynes and Diaryliodonium Salts
  作者：Ze-Feng Xu、Chen-Xin Cai、Jin-Tao Liu

  DOI：10.1021/ol4003543

  日期：2013.5.3

  The copper-catalyzed highly regioselective reaction of internal alkynes with diaryliodonium salts was achieved for the first time. α-Arylketones were obtained in moderate to good yields from arylpropargylic alcohols or aryl alkyl alkynes under mild conditions. It was found that the two kinds of substrates underwent two different arylation–oxygenation pathways under different reaction conditions based

  首次实现了内部炔烃与二芳基碘鎓盐的铜催化的高度区域选择性反应。在温和的条件下，从芳基炔丙醇或芳基烷基炔烃以中等至良好的产率获得α-芳基酮。基于氘代实验，控制实验和反应中间体的光谱分析，发现两种底物在不同的反应条件下经历了两种不同的芳构化-加氧途径。
• Zinc(II) Catalyzed Conversion of Alkynes to Vinyl Triflates in the Presence of Silyl Triflates
  作者：Mohammed H. Al-huniti、Salvatore D. Lepore

  DOI：10.1021/ol501852n

  日期：2014.8.15

  The conversion of alkynes to their corresponding vinyl triflates in the presence of stoichiometric TMS-triflate was greatly facilitated by the triflate salt of several transition metal catalysts most especially Zn(OTf)2. Products are formed in high regioselectivity under mild conditions. Internal alkynes bearing an aryl substituent afford vinyl triflates with a modest preference for the Z-isomer especially with larger substituents. A mechanism is put forward to explain the unique role of silicon in this system.
• Ionic Hydrogenation of Alkynes by HOTf and Cp(CO)3WH
  作者：Li Luan、Jeong-Sup Song、R. Morris Bullock

  DOI：10.1021/jo00127a023

  日期：1995.11

  Alkynes can be hydrogenated at room temperature by an ionic hydrogenation method using triflic acid (CF3SO3H) as the proton donor and a transition metal hydride (Cp(CO)(3)WH) as the hydride donor. Reaction of PhC=CH with HOTf and Cp(CO)(3)WH gives ethylbenzene as the final product in high yield. Intermediates observed in this reaction are the vinyl triflate CH2=C(Ph)(OTf) and the geminal ditriflate Ph(CH3)C(OTf)(2), which result from the addition of 1 or 2 equiv of HOTf to the C=C triple bond of the alkyne. Hydrogenation of PhC=CMe by HOTf and Cp(CO)(3)WH similarly produces propylbenzene as the ultimate product. Along with vinyl triflates, additional intermediates observed in this reaction were the cis and trans isomers of the beta-methylstyrene complex [Cp(CO)(3)W-(eta(2)-PhHC=CHCH3)](+)[OTf](-). Hydrogenation of n-butylacetylene to n-hexane does occur upon reaction with HOTf/Cp(CO)(3)WH, but is very slow. In the absence of metal hydrides, 2-methyl-1-buten-3-yne reacts with HOTf to give the vinyl triflate CH2=CMeC(OTf)=CH2, but reaction with HOTf and Cp(CO)(3)WH gives Me(2)C=C(OTf)Me. The key characteristics required for the metal hydride used in these hydrogenations are the ability to donate hydride in the presence of strong acid, and the absence of rapid decomposition of the hydride through reaction with the strong acid. Cp(CO)(3)WH meets these requirements, but HSiEt(3), while an effective hydride donor, is decomposed by HOTf on the time scale of these alkyne hydrogenation reactions.
• Total Synthesis of (+)-α-Onocerin in Four Steps via Four-Component Coupling and Tetracyclization Steps
  作者：Yuan Mi、Jürg V. Schreiber、E. J. Corey

  DOI：10.1021/ja027373f

  日期：2002.9.1

  rings in one step by cation-olefin tetracyclization. New and general methodology for the conversion of vinyl tert-butyldimethylsilyl ethers to vinyl triflates with retention of E or Z olefinic geometry also was utilized in the synthesis of 1. A short enantioselective synthesis of a non-C2-symmetric diastereomer of 1 is also described which uses the new methodology.

  结构独特的 C2 对称四环三萜 (+)-α-橙黄素 (1) 的对映选择性合成非常短（四步，总产率为 31%）。这种机制的简洁性取决于四个片段（两个手性环氧酮分子和两个乙烯基锂分子）的组装以一步生成手性双环氧化物 4，以及所有四个碳环在一个步骤中的有效形成逐步进行阳离子-烯烃四环化。在 1 的合成中也使用了将乙烯基叔丁基二甲基甲硅烷基醚转化为乙烯基三氟甲磺酸酯的新通用方法，同时保留了 E 或 Z 烯烃几何结构。还描述了 1 的非 C2 对称非对映异构体的短对映选择性合成它使用了新的方法论。