(E)-3-(2-phenoxy-1-phenylselenenylmethyl-ethoxy)-acrylic acid ethyl ester | 396714-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-(2-phenoxy-1-phenylselenenylmethyl-ethoxy)-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-(1-phenoxy-3-phenylselanylpropan-2-yl)oxyprop-2-enoate
• CAS: 396714-87-7
• 化学式: C₂₀H₂₂O₄Se
• 分子量: 405.352
• InChiKey: UBDJYVXYDUCNGT-BUHFOSPRSA-N

物化性质

• 沸点：
  514.1±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (E)-3-(2-phenoxy-1-phenylselenenylmethyl-ethoxy)-acrylic acid ethyl ester 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 作用下， 以 苯 为溶剂， 80.0 ℃ 、8.11 MPa 条件下， 以6%的产率得到(E)-3-(1-methyl-2-phenoxy-ethoxy)-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
• 作为产物：
  描述：

  苯基缩水甘油醚 在 N-甲基吗啉 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(2-phenoxy-1-phenylselenenylmethyl-ethoxy)-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

• 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).