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

中文名称
——
中文别名
——
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
(E)-3-(2-phenoxy-1-phenylselenenylmethyl-ethoxy)-acrylic acid ethyl ester化学式
CAS
396714-87-7
化学式
C20H22O4Se
mdl
——
分子量
405.352
InChiKey
UBDJYVXYDUCNGT-BUHFOSPRSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

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偶氮二异丁腈三(三甲基硅基)硅烷 作用下, 以 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:
    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
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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).
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