Ethyl 3-(1-phenylethoxy)acrylate | 146176-68-3

• 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: Ethyl 3-(1-phenylethoxy)acrylate
• 英文别名: (E)-3-(1-phenyl-ethoxy)-acrylic acid ethyl ester；ethyl (E)-3-(1-phenylethoxy)prop-2-enoate
• CAS: 146176-68-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: CXHHIFFZQWATDB-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 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：

  ethyl (E)-3-(phenylsulfonyl)-2-propenoate 、 Ethyl 3-(1-phenylethoxy)acrylate 在 lithium diisopropyl amide 作用下， 生成 (1R,5R)-5-Benzenesulfonyl-4-oxo-2-(1-phenyl-ethoxy)-cyclopent-2-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Chiral β-C-lithiated β-alkoxy acrylates: Efficient synthons for highly functionalized cyclopentenones

  摘要：

  A one step synthesis of highly functionalized cyclopentenones has been developed by the Michael addition of the readily available beta-lithiated acrylate 1A with suitable acceptors.

  DOI：

  10.1016/s0040-4039(00)60517-8
• 作为产物：
  描述：

  1-phenyl-2-(phenylselanyl)ethanol 在 N-甲基吗啉 、 偶氮二异丁腈 、 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 Ethyl 3-(1-phenylethoxy)acrylate
  参考文献：
  名称：

  Radical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones

  摘要：

  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).

  DOI：

  10.1021/jo030153f

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.

  该发明涉及香气前体，具体来说，该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洗衣产品如洗涤剂和织物柔顺剂中的应用。这些化合物本身是无味的，但当接触皮肤时，例如在护肤品或个人护理品中，会产生香气。这些化合物在存在脂肪酶时也会产生香气，例如在（洗衣）洗涤剂中使用，从而延长织物的香气效果。所考虑的化合物是符合式I的化合物：其中取代基在说明书中有定义。
• Stereoselective synthesis of β-alkoxy- and β-alkylthio-acrylic esters and amides from β-tosylacrylic derivatives
  作者：Salvador Blaya、Rafael Chinchilla、Carmen Nájera

  DOI：10.1016/0040-4020(95)00077-l

  日期：1995.3

  A simple and stereoselective synthesis of β-alkoxy- and β-alkylthio-acrylic esters and amides (8) by nucleophilic vinylic substitution of the tosyl group by sodium alcoholates and thiolates of (E)-β-tosylacrylic derivatives (7), prepared by iodosulfonylation-dehydroiodination of acrylic compounds, is described. This methodology is applied to the synthesis of sinharine (8eh) a natural antifungal isolated

  通过（E）-β-甲苯磺酰基丙烯酸衍生物（7）的醇盐和硫醇酸钠的亲核乙烯基取代甲苯磺酰基的简单立体立体合成β-烷氧基-和β-烷硫基丙烯酸酯和酰胺（8）描述了丙烯酸化合物的碘磺酰化-脱氢碘化。这种方法被施加到sinharine（合成8EH）天然抗真菌分离自山小桔属cyanocarpa。
• A convenient stereoselective synthesis of a (−)-vertinolide precursor
  作者：Apurba Datta、Dinah Datta、Richard R. Schmidt

  DOI：10.1016/s0040-4039(00)74710-1

  日期：1992.12

  A short practical method for the enantioselective synthesis of (−)-vertinolide precursor 2 is described. The readily available chiral β-alkoxy substituted acrylate 7 has been reacted with the ethyl levulinate to form the tetronic acid nucleus 8, which in three subsequent steps was converted to the known precursor 2 in high overall yield.

  描述了用于（-）-眩晕内酯前体2的对映选择性合成的简短实用方法。容易获得的手性β-烷氧基取代的丙烯酸酯7已经与乙酰丙酸乙酯反应形成四氢代酸核8，其在随后的三个步骤中以高总收率转化为已知的前体2。
• 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