(E)-ethyl 3-(trifluoromethylsulfonyloxy)pent-2-enoate | 353744-10-2

• 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: (E)-ethyl 3-(trifluoromethylsulfonyloxy)pent-2-enoate
• 英文别名: ethyl (E)-3-(trifluoromethylsulfonyloxy)pent-2-enoate；ethyl (E)-3-trifluoromethanesulfonyloxy-2-pentenoate；3-(Trifluoromethylsulfonyloxy)-2-pentenoic acid ethyl ester
• CAS: 353744-10-2
• 化学式: C₈H₁₁F₃O₅S
• 分子量: 276.234
• InChiKey: GQRIHLWYTCXOFF-AATRIKPKSA-N

物化性质

• 沸点：
  283.5±40.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(trifluoromethylsulfonyloxy)pent-2-enoate 在 4-二甲氨基吡啶 、 potassium phosphate 、 四丁基氟化铵 、 palladium diacetate 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 三乙胺 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 23.58h， 生成 (E)-3-(3-[(8-formyl)oct-5-ynyl]phenoxy)pent-2-enyl acetate
  参考文献：
  名称：

  Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems

  摘要：

  使用Pd催化的交叉偶联、Wittig烯化和锂化/烷基化方法构建了具有跳跃不饱和度的新型大环聚炔化合物1；最终的Stille大环化反应利用了有前景的预催化剂AsCat。

  DOI：

  10.1039/c5cc02091c
• 作为产物：
  描述：

  三氟甲磺酸酐 、 丙酰乙酸乙酯 在 四甲基氢氧化铵 作用下， 以 正己烷 、 水 为溶剂， 反应 0.5h， 以63%的产率得到(E)-ethyl 3-(trifluoromethylsulfonyloxy)pent-2-enoate
  参考文献：
  名称：

  Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems

  摘要：

  使用Pd催化的交叉偶联、Wittig烯化和锂化/烷基化方法构建了具有跳跃不饱和度的新型大环聚炔化合物1；最终的Stille大环化反应利用了有前景的预催化剂AsCat。

  DOI：

  10.1039/c5cc02091c

文献信息

• Stereocontrolled Synthesis of 13-Substituted Retinoic Acids by Palladium-Catalyzed Coupling Reaction of Alkenyl Stannane with Vinyl Triflate
  作者：Akimori Wada、Kouki Fukunaga、Masayoshi Ito

  DOI：10.1055/s-2001-14908

  日期：——

  A novel method for the stereoselective synthesis of all-E-, 13Z- and 9Z-retionic acid esters was developed by palladium-catalyzed cross coupling reactions of tetraenyl stannanes with E- or Z-vinyl triflates in good yields. Applying this methodology, 13-substituted all-E- and 9Z-retionic acids were prepared in satisfactory yields.

  一种新的立体选择性合成全E-、13Z-和9Z-维甲酸酯的方法，通过钯催化的四烯基锡与E型或Z型乙烯基三氟甲磺酸酯的交叉耦合反应，产率良好。应用此方法，成功以满意的产率制备了13-取代的全E-和9Z-维甲酸。
• Stereoselective Synthesis of Acetoacetate-Derived Enol Triflates
  作者：David Babinski、Omid Soltani、Doug E. Frantz

  DOI：10.1021/ol8010002

  日期：2008.7.3

  A highly stereoselective method for preparing ( Z)- and ( E)-enol triflates derived from substituted acetoacetate derivatives is described. The salient feature of this methodology is the use of Schotten-Baumann-type conditions to control enolate geometry using either aqueous LiOH ( Z-selective) or aqueous (Me)(4)NOH ( E-selective) in combination with triflic anhydride to provide a practical and predictable

  描述了用于制备衍生自取代的乙酰乙酸酯衍生物的（Z）-和（E）-烯醇三氟甲磺酸酯的高度立体选择性的方法。该方法的显着特征是使用Schotten-Baumann型条件通过使用LiOH水溶液（Z选择性）或（Me）（4）NOH水溶液（E选择性）与三氟甲磺酸酐组合来控制烯醇几何形状，以提供这些有价值的基材的实用且可预测的方法。
• Chemoenzymatic Asymmetric Synthesis of Pregabalin Precursors via Asymmetric Bioreduction of β-Cyanoacrylate Esters Using Ene-Reductases
  作者：Christoph K. Winkler、Dorina Clay、Simon Davies、Pat O’Neill、Paul McDaid、Sebastien Debarge、Jeremy Steflik、Mike Karmilowicz、John W. Wong、Kurt Faber

  DOI：10.1021/jo302484p

  日期：2013.2.15

  The asymmetric bioreduction of a library of beta-cyanoacrylate esters using ene-reductases was studied with the aim to provide a biocatalytic route to precursors for GABA analogues, such as pregabalin. The stereochemical outcome could be controlled by substrate-engineering through size-variation of the ester moiety and by employing stereochemically pure (E)- or (Z)-isomers, which allowed to access both enantiomers of each product in up to quantitative conversion in enantiomerically pure form. In addition, stereoselectivities and conversions could be improved by mutant variants of OPR1, and the utility of the system was demonstrated by preparative-scale applications.
• Preparation and biological activity of 13-substituted retinoic acids
  作者：Akimori Wada、Kouki Fukunaga、Masayoshi Ito、Yukari Mizuguchi、Kimie Nakagawa、Toshio Okano

  DOI：10.1016/j.bmc.2004.04.047

  日期：2004.7

  13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity. (C) 2004 Elsevier Ltd. All rights reserved.
• Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems
  作者：Thomas O. Ronson、Martin H. H. Voelkel、Richard J. K. Taylor、Ian J. S. Fairlamb

  DOI：10.1039/c5cc02091c

  日期：——

  Novel macrocyclic polyenyne 1, with skipped unsaturation, has been constructed using Pd-catalysed cross-coupling, Wittig olefination and lithiation/alkylation methodologies; the final Stille macrocyclisation utilised the promising precatalyst, AsCat.

  使用Pd催化的交叉偶联、Wittig烯化和锂化/烷基化方法构建了具有跳跃不饱和度的新型大环聚炔化合物1；最终的Stille大环化反应利用了有前景的预催化剂AsCat。