(E)-3-phenethyloxy-acrylic acid ethyl ester

• 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: (E)-3-phenethyloxy-acrylic acid ethyl ester
• 英文别名: (E)-phenethyloxy-acrylic acid ethyl ester；ethyl (E)-3-phenethoxyacrylate；(E)-3-Phenylethyloxy-acrylic acid ethyl ester；ethyl (E)-3-(2-phenylethoxy)prop-2-enoate
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: WISASEKIBJBUHU-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (E)-3-phenethyloxy-acrylic acid ethyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到ethyl 1-isochromanylacetate
  参考文献：
  名称：

  通过乙烯基酯的Oxa-Pictet-Spengler反应合成异色满衍生物

  摘要：

  摘要 三氟甲磺酸三甲基甲硅烷基酯（TMSOTf）可通过Pictet-Spengler型乙烯基酯类反应以高收率有效地用于异氰酸酯的合成。该方法适用于正式的关键中间体醇的合成，用于合成D 4拮抗剂索尼派拉唑（±）-U-101387和异色满（±）-U-54537。 三氟甲磺酸三甲基甲硅烷基酯（TMSOTf）可通过Pictet-Spengler型乙烯基酯类反应以高收率有效地用于异氰酸酯的合成。该方法适用于正式的关键中间体醇的合成，用于合成D 4拮抗剂索尼派拉唑（±）-U-101387和异色满（±）-U-54537。

  DOI：

  10.1055/s-0035-1561581
• 作为产物：
  描述：

  2-hydroxy-1-phenylethyl phenyl selenide 在 N-甲基吗啉 、 偶氮二异丁腈 、 一氧化碳 、 三(三甲基硅基)硅烷 作用下， 以 二氯甲烷 、 苯 为溶剂， 20.0 ℃ 、8.11 MPa 条件下， 生成 (E)-3-phenethyloxy-acrylic acid ethyl ester
  参考文献：
  名称：

  Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization

  摘要：

  [GRAPHICS]b-Hydroxyalkyl aryl chalcogenides, readily available by regioselective ring-opening of epoxides with nucleophilic benzeneselenolate or tellurolate, were O-alkylated by treatment with ethyl propiolate or (E)-1,2-bis(phenylsulfonyl)ethylene. Subsequent carbonylation/reductive cyclization in the presence of AIBN/TTMSS and carbon monoxide (80 atm) afforded tetrahydrofuran-3-ones in moderate to good yields.

  DOI：

  10.1021/ol016127q

文献信息

• Fragrance precursors
  申请人：Givaudan Roure (International) SA

  公开号：US06306818B1

  公开（公告）日：2001-10-23

  The invention relates to fragrance precursors, In particular, the invention relates to the use of several classes of compounds which may act as fragrance precursors, e,g., in cosmetic products such as deodorants and antiperspirants and in laundry products such as detergents and fabric softners. These compounds are odorless, but upon contacting the skin as example, in skin care compositions or in personal care compositions, produce fragrances. The compounds also produce fragrances when used in the presence of lipases, e.g. as used in (laundry) detergents, thus providing a prolongation of the fabric scenting effect. The compounds under consideration are compounds of the formula I: The substituents are defined in the specification.

  本发明涉及香气前体，具体而言，本发明涉及使用几类化合物作为香气前体，例如在化妆品产品如除臭剂和止汗剂，以及在洗涤产品如洗涤剂和柔顺剂中。这些化合物是无味的，但是当接触皮肤时，例如在皮肤护理组合物或个人护理组合物中，会产生香气。当这些化合物在脂肪酶存在下使用时，例如在（洗涤）洗涤剂中使用时，它们也会产生香气，从而提供织物香气效果的延长。所考虑的化合物是I式化合物：其中取代基在说明书中有定义。
• Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization
  作者：Stefan Berlin、Cecilia Ericsson、Lars Engman

  DOI：10.1021/ol016127q

  日期：2002.1.1

  [GRAPHICS]b-Hydroxyalkyl aryl chalcogenides, readily available by regioselective ring-opening of epoxides with nucleophilic benzeneselenolate or tellurolate, were O-alkylated by treatment with ethyl propiolate or (E)-1,2-bis(phenylsulfonyl)ethylene. Subsequent carbonylation/reductive cyclization in the presence of AIBN/TTMSS and carbon monoxide (80 atm) afforded tetrahydrofuran-3-ones in moderate to good yields.
• US6306818B1
  申请人：——

  公开号：US6306818B1

  公开（公告）日：2001-10-23
• Radical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones
  作者：Stefan Berlin、Cecilia Ericsson、Lars Engman

  DOI：10.1021/jo030153f

  日期：2003.10.1

  beta-Hydroxyalkyl aryl chalcogenides obtained by regioselective ring-opening of epoxides with benzeneselenolate or -tellurolate were found to undergo efficient hetero-Michael addition when treated with ethyl propiolate. Subsequent carbonylation/reductive cyclization of the resulting vinylogous carbonates in the presence of AIBN/TTMSS and carbon monoxide (80 atm) afforded 2,5-disubstituted tetrahydrofuran-3-ones, predominantly as cis isomers (cis/trans = 4/1-9/1). Starting from a polymer-supported diaryl diselenide, the methodology was also successfully extended to solid-phase synthesis. Vinylogous carbamates prepared by hetero-Michael addition of aziridines to electron-deficient alkynes were regioselectively ring-opened with benzeneselenolate from the sterically least hindered side. Radical carbonylation/reductive cyclization of the resulting N-vinyl-beta-amino-alkyl phenyl selenides afforded 2,5-disubstituted pyrrolidin-3-ones, predominantly as cis isomers (cis/trans = 3/1-12/1).
• Synthesis of Isochroman Derivatives via Oxa-Pictet–Spengler Reaction of Vinylogous Esters
  作者：Anil Saikia、Sujit Sarkar、Sabera Sultana、Kiran Indukuri、Ramanjaneyulu Unnava

  DOI：10.1055/s-0035-1561581

  日期：——

  Pictet–Spengler type reaction of vinylogous esters in good yields. The methodology is applied for the formal synthesis of key intermediate alcohols for the synthesis of D4 antagonist sonepiprazole (±)-U-101387 and the isochroman (±)-U-54537. Trimethylsilyl triflate (TMSOTf) can be efficiently used for the synthesis of isochromans via Pictet–Spengler type reaction of vinylogous esters in good yields. The methodology

  摘要 三氟甲磺酸三甲基甲硅烷基酯（TMSOTf）可通过Pictet-Spengler型乙烯基酯类反应以高收率有效地用于异氰酸酯的合成。该方法适用于正式的关键中间体醇的合成，用于合成D 4拮抗剂索尼派拉唑（±）-U-101387和异色满（±）-U-54537。 三氟甲磺酸三甲基甲硅烷基酯（TMSOTf）可通过Pictet-Spengler型乙烯基酯类反应以高收率有效地用于异氰酸酯的合成。该方法适用于正式的关键中间体醇的合成，用于合成D 4拮抗剂索尼派拉唑（±）-U-101387和异色满（±）-U-54537。