2-methoxyethyl propiolate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methoxyethyl propiolate
• 英文别名: Ldjbuerbdccuie-uhfffaoysa-；2-methoxyethyl prop-2-ynoate
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: LDJBUERBDCCUIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxyethyl propiolate 在 水 、 potassium thioacyanate 作用下， 反应 10.0h， 以91%的产率得到2-methoxyethyl (Z)-3-thiocyanatoacrylate
  参考文献：
  名称：

  Deep eutectic solvent promoted hydrothiocyanation of alkynoates leading to Z-3-thiocyanatoacrylates

  摘要：

  A mild and efficient protocol for the selective construction of Z-3-thiocyanatoacrylates is described. Various alkynoates reacted with KSCN and H2O by using cheap and recyclable deep eutectic solvent as the catalyst and reaction media to produce the corresponding products in excellent yields with mild reaction conditions and wide substrate scope. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2019.07.014
• 作为产物：
  描述：

  乙二醇甲醚 、 丙炔酸 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以42%的产率得到2-methoxyethyl propiolate
  参考文献：
  名称：

  炔烃与环烷烃的光导反应。

  摘要：

  在光介体如二苯甲酮的存在下，具有吸电子基团的炔烃与环烷烃反应生成乙烯基环烷烃。该反应涉及将光化学产生的环烷基的区域特异性加成到炔烃的β-碳上。反应的立体化学结果取决于所使用的光介体和炔烃的性质。

  DOI：

  10.1039/b517631j

文献信息

• The photomediated reaction of alkynes with cycloalkanes
  作者：Roísín A. Doohan、John J. Hannan、Niall W. A. Geraghty

  DOI：10.1039/b517631j

  日期：——

  of a photomediator such as benzophenone, alkynes with electron-withdrawing groups react with cycloalkanes to give vinyl cycloalkanes. The reaction involves the regiospecific addition of a photochemically generated cycloalkyl radical to the beta-carbon of the alkyne. The stereochemical outcome of the reaction depends on the nature of the photomediator and alkyne used.

  在光介体如二苯甲酮的存在下，具有吸电子基团的炔烃与环烷烃反应生成乙烯基环烷烃。该反应涉及将光化学产生的环烷基的区域特异性加成到炔烃的β-碳上。反应的立体化学结果取决于所使用的光介体和炔烃的性质。
• Synthesis of Isocoumarins via Silver(I)-Mediated Annulation of Enol Esters
  作者：Niranjan Panda、Priyadarshini Mishra、Irshad Mattan

  DOI：10.1021/acs.joc.5b02602

  日期：2016.2.5

  annulation of 2-iodo enol esters leading to 4- and 3,4-substituted isocoumarins was accomplished selectively at room temperature. Coupling of 2-iodo benzoic acids with enolates that were produced in situ from the simple esters was also performed to produce isocoumarins under analogous reaction conditions. Owing to the mildness of the current protocol, 4-acyl 3-substituted isocoumarins were efficiently produced

  在室温下选择性地完成了银介导的2-碘烯醇酯的环化反应，产生4-和3,4-取代的异香豆素。在类似的反应条件下，还进行了2-碘苯甲酸与由简单酯原位生成的烯醇盐的偶联，以生产异香豆素。由于当前方案的温和性，有效地生产了4-酰基3-取代的异香豆素，而没有任何脱酰作用。
• A direct catalyst-free and stereoselective sulfonylation of propargyl esters for efficient synthesis of (Z)-β-sulfonyl enoates in water
  作者：Jun Jiang、Yundong Wu、Ruijia Wang、Yongzhao He、Chonghui Xu、Wei Deng、Zebing Zeng、Jiannan Xiang

  DOI：10.1016/j.tet.2016.09.037

  日期：2016.12

  Water-promoted sulfonylation of propargyl esters leading to highly regioselective and stereoselective formation of (Z)-β-sulfonyl enoates in excellent yields, by a simple, mild, and environmentally benign reaction procedure without employing any ligand or additive is reported.

  据报道，通过简单，温和且对环境无害的反应程序，无需使用任何配体或添加剂，丙炔酸酯的水促进的磺酰化导致（Z）-β-磺酰基烯酸酯的高度区域选择性和立体选择性的形成，产率极高。
• Deep eutectic solvent promoted hydrothiocyanation of alkynoates leading to Z-3-thiocyanatoacrylates
  作者：Meng Sun、Jun Jiang、Jialiang Chen、Qiao Yang、Xianyong Yu

  DOI：10.1016/j.tet.2019.07.014

  日期：2019.8

  A mild and efficient protocol for the selective construction of Z-3-thiocyanatoacrylates is described. Various alkynoates reacted with KSCN and H2O by using cheap and recyclable deep eutectic solvent as the catalyst and reaction media to produce the corresponding products in excellent yields with mild reaction conditions and wide substrate scope. (C) 2019 Elsevier Ltd. All rights reserved.
• Radical copolymerization of alkyl cyclobutenecarboxylates fused with cycloaliphatic framework with alkyl (meth)acrylates
  作者：Eiji Ihara、Takafumi Ueda、Kotaro Yokoyama、Yuka Fujiwara、Kenzo Inoue、Tomomichi Itoh、Hiroaki Shimomoto、Hikaru Momose、Mitsufumi Nodono

  DOI：10.1002/pola.26668

  日期：2013.6.15

  Radical copolymerization behavior of alkyl cyclobutenecarboxylate‐derivatives 4‐6 and related norbornene‐derived compounds 7–9 is described. A variety of alkyl cyclobutenecarboxylates fused with cycloaliphatic framework (4–6) were prepared by [2 + 2] cycloaddition of five, six, and eight‐membered cycloolefins with alkyl propiolates [alkyl = Me, 2‐hydroxyethyl, and 3‐γ‐butyrolactonyl (γ‐BL)]. The fused

  描述了烷基环丁烯羧酸酯衍生物4-6和相关降冰片烯衍生化合物7-9的自由基共聚行为。各种具有脂环族骨架（稠合的烷基cyclobutenecarboxylates的4-6）通过环加成5的[2 + 2]制备，六，八元的环烯烃与烷基的丙炔酸酯[烷基= Me中，2-羟乙基，和3-γ-丁内酯（γ-BL）]。稠合的环丁烯羧酸盐4-6与丙烯酸正丁酯（nBA）提供无规共聚物，并与具有庞大酯基[烷基=γ-BL和3-（3-甲基金刚烷基）]的甲基丙烯酸烷基酯进行三元聚合。包含在所得聚合物主链中的含环丁烷双环骨架有助于提高所得共聚物的T g。当使用相关的降冰片烯衍生化合物的混合物作为单体时，与n BA共聚时，T g的升高作用明显增强，获得了相似的结果。©2013 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学 2013，51，2716–2724

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