trifluoromethanesulfonic acid 3-phenylpropenyl ester | 872214-87-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trifluoromethanesulfonic acid 3-phenylpropenyl ester
• 英文别名: 3-phenyl-1-(((trifluoromethyl)sulfonyl)oxy)propene；3-phenylprop-1-en-1-yl trifluoromethanesulfonate；3-phenyl-1-propen-1-yl triflate；3-phenyl-1-{[(trifluoromethyl)sulfonyl]oxy}propene
• CAS: 872214-87-4
• 化学式: C₁₀H₉F₃O₃S
• 分子量: 266.241
• InChiKey: SXSTXLMRTUSKCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  318.3±42.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 3-phenylpropenyl ester 在 palladium dihydroxide 吡啶 、 acetate buffer 、 氢气 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 4-ethyl-10-(3-hydroxy-6-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-11-methoxy-3a,7,9,11,13,15-hexamethyl-octahydro-1,3,5-trioxa-cyclopentacyclotetradecene-2,6,8,14-tetraone 14-[O-(6-phenyl-hexyl)-oxime]
  参考文献：
  名称：

  A new type of ketolides bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether synthesis and structure–activity relationships

  摘要：

  A new type of ketolides, bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether and a cyclic carbonate at the G 11, 12 position was prepared and the antibacterial activities of the compounds were evaluated. Some of the derivatives showed potent antibacterial activity against both Haemophilus influenzae and Streptococcus pneumoniae, which are clinically important respiratory tract pathogens. Among the derivatives prepared, compound 5s with a quinolin-4-yl moiety was found to have potent and well-balanced activity against S. pneumoniae and H. influenzae including erythromycin-resistant strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.041
• 作为产物：
  描述：

  苯丙醛 、 三氟甲磺酸酐 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 trifluoromethanesulfonic acid 3-phenylpropenyl ester
  参考文献：
  名称：

  烯醛三氟甲磺酸酯还原法从醛类中制得末端烯烃

  摘要：

  描述了通过还原相应的烯醇三氟甲磺酸酯将醛转化为末端烯烃的方法。该方法对线性和α-支化醛均有效。

  DOI：

  10.1021/jo071151o

文献信息

• Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers
  作者：Harshkumar H. Patel、Matthew S. Sigman

  DOI：10.1021/jacs.6b09649

  日期：2016.11.2

  In this report, we describe the generation of remote allylic quaternary stereocenters β, γ, and δ relative to a carbonyl in high enantioselectivity. We utilize a redox-relay Heck reaction between alkenyl triflates and acyclic trisubstituted alkenols of varying chain-lengths. A wide array of terminal (E)-alkenyl triflates are suitable for this process. The utility of this functionalization is validated

  在本报告中，我们描述了相对于羰基以高对映选择性生成远程烯丙基四元立体中心 β、γ 和 δ。我们利用链烯基三氟甲磺酸酯和不同链长的无环三取代烯醇之间的氧化还原中继 Heck 反应。多种末端 (E)-烯基三氟甲磺酸酯适用于该过程。这种功能化的效用通过产品的转化得到进一步验证，通过简单的有机过程获得远程功能化的手性叔酸、胺和醇产品。
• Synthesis of <i>N</i> -alkyl-<i>N</i> ′-aryl or Alkenylpiperazines: A Copper-Catalyzed C-N Cross-Coupling in the Presence of Aryl and Alkenyl Triflates and DABCO
  作者：Majid Ghazanfarpour-Darjani、Forugh Barat-Seftejani、Mehdi Khalaj、Seyed Mahmoud Mousavi-Safavi

  DOI：10.1002/hlca.201700082

  日期：2017.8

  introduction of an aryl and alkyl motif onto the piperazine is not always straightforward, direct arylation and alkenylation of 1,4‐diaza‐bicyclo[2.2.2]octane would obviate the inefficiencies associated with the preparation of these target molecules. We have utilized alkyl halides, aryl or alkenyl triflates, and 1,4‐diaza‐bicyclo[2.2.2]octane for the synthesis of N‐alkyl‐N′‐aryl or alkenylpiperazines

  不对称哌嗪是许多药物的关键成分。鉴于将芳基和烷基基序选择性引入哌嗪并不总是那么简单，因此1,4-二氮杂双环[2.2.2]辛烷的直接芳基化和烯基化将消除与这些目标分子制备相关的低效率。我们利用卤代烷，芳基或烯基三氟甲磺酸酯和1,4-二氮杂双环[2.2.2]辛烷来合成N-烷基-N'-芳基或烯基哌嗪。在NMP中使用CuCl，t- BuOLi来确定最佳条件。烯基三氟甲磺酸盐需要N，N'-二甲基乙二胺和更高的温度提供所需的交叉偶联产物。在最佳反应条件下，成功地偶联了具有缺电子和富电子基团的底物。
• Nickel‐Catalyzed Reductive Coupling of Vinyl Triflates and 1,4‐Dicyanobenzene to Access Alkenyl Nitriles
  作者：Le‐Le Wang、Zhong‐Xian Li、Jun Zhu

  DOI：10.1002/adsc.202301072

  日期：2024.2.19

  We report a vinyl cyanation reaction of vinyl triflates and readily available 1,4-dicyanobenzene through a nickel-catalyzed reductive coupling process. The reaction is operated under mild conditions with remarkable functional-group compatibility. Cyclic vinyl triflates with various ring sizes and substituents at different positions all reacted smoothly. The synthetic utility is demonstrated by the

  我们报告了乙烯基三氟甲磺酸酯和容易获得的 1,4-二氰基苯通过镍催化还原偶联过程的乙烯基氰化反应。该反应条件温和，官能团相容性好。不同环尺寸和不同位置取代基的环状乙烯基三氟甲磺酸酯均能顺利反应。合成效用通过药物和天然化合物的衍生化、放大合成和各种官能团转化来证明。初步机理研究表明，三氟甲磺酸乙烯酯对镍催化剂的氧化加成反应比 1,4-二氰基苯更具反应性。
• Ruthenium-Catalyzed Transformation of Aryl and Alkenyl Triflates to Halides
  作者：Yusuke Imazaki、Eiji Shirakawa、Ryota Ueno、Tamio Hayashi

  DOI：10.1021/ja307771d

  日期：2012.9.12

  Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)(3)]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition to a ruthenium(II) complex to form eta(1)-arylruthenium and 1-ruthenacyclopropene intermediates, respectively, which are transformed to the corresponding halides.
• Intermolecular couplings between vinyl triflates and allylic cuprates: a mild and rapid atypical route to 1,4-dienes
  作者：Bruce H. Lipshutz、Todd R. Elworthy

  DOI：10.1021/jo00293a002

  日期：1990.3