diethyl (Z)-4-phenylbut-1-en-3-ynylphosphonate | 169230-17-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl (Z)-4-phenylbut-1-en-3-ynylphosphonate
• 英文别名: [(Z)-4-diethoxyphosphoryl-but-3-en-1-ynyl]-benzene；[(Z)-4-diethoxyphosphorylbut-3-en-1-ynyl]benzene
• CAS: 169230-17-5
• 化学式: C₁₄H₁₇O₃P
• 分子量: 264.261
• InChiKey: GEBVXJLTJDVQQO-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  diethyl (Z)-4-phenylbut-1-en-3-ynylphosphonate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 ethyl hydrogen (Z)-4-phenylbut-1-en-3-ynylphosphonate
  参考文献：
  名称：

  Synthesis of 2H-1,2-Oxaphosphorin 2-Oxides via Ag₂CO₃-Catalyzed Cyclization of (Z)-2-Alken-4-ynylphosphonic Monoesters

  摘要：

  Six new 2-ethoxy-2H-1,2-oxaphosphorin 2-oxides were synthesized with high regioselectivity in good yields via Ag2CO3-Catalyzed cyclization of (2)-2-alken-4-ynylphosphonic monoesters in CH2Cl2 at room temperature. This cyclization of P-OH to substituted alkynes is reported for the first time. The products are a class of phosphorus heterocycles with potential use and are heretofore prepared with difficulty.

  DOI：

  10.1021/ol051126+
• 作为产物：
  描述：

  苯基乙炔三丁基锡 、 diethyl (Z)-2-iodovinylphosphonate 在 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以56%的产率得到diethyl (Z)-4-phenylbut-1-en-3-ynylphosphonate
  参考文献：
  名称：

  Suzuki and Stille Cross-Coupling Reactions from β-Iodovinylphosphonate: Stereoselective Access to Various Substituted Vinylphosphonates

  摘要：

  Stereoselective synthesis of beta-arylvinyl, dienyl, and enynylphosphonates was achieved from diethyl 2-iodovinylphosphonate via Suzuki or Stille cross-coupling reactions in good yields.

  DOI：

  10.1055/s-0034-1378360

文献信息

• A Convenient Stereoselective Synthesis of 1,3-Dienylphosphonates and 1-En-3-ynylphosphonates and Their Phosphine Oxide Analogs
  作者：Xiaoling Huang、Chunming Zhang、Xiyan Lu

  DOI：10.1055/s-1995-4000

  日期：1995.7

  Ethynylphosphonates (or phosphine oxides) react with a lithium halide in acetic acid at 70°C to yield (Z)-2-halovinylphosphonates (or phosphine oxides), which give (1Z,3E)-dienylphosphonates and (1Z)-en-3-ynylphosphonates (phosphine oxides) after coupling with alkenes and alkynes, respectively, in the presence of a palladium catalyst.

  乙炔基膦酸酯（或膦氧化物）在70°C的醋酸中与锂卤化物反应，生成(Z)-2-卤烯基膦酸酯（或膦氧化物），这些反应产物在钯催化剂的存在下，分别与烯烃和炔烃偶联，生成(1Z,3E)-二烯基膦酸酯和(1Z)-en-3-炔基膦酸酯（膦氧化物）。
• Synthesis of 2<i>H</i>-1,2-Oxaphosphorin 2-Oxides via Ag₂CO₃-Catalyzed Cyclization of (<i>Z</i>)-2-Alken-4-ynylphosphonic Monoesters
  作者：Ai-Yun Peng、Yi-Xiang Ding

  DOI：10.1021/ol051126+

  日期：2005.7.1

  Six new 2-ethoxy-2H-1,2-oxaphosphorin 2-oxides were synthesized with high regioselectivity in good yields via Ag2CO3-Catalyzed cyclization of (2)-2-alken-4-ynylphosphonic monoesters in CH2Cl2 at room temperature. This cyclization of P-OH to substituted alkynes is reported for the first time. The products are a class of phosphorus heterocycles with potential use and are heretofore prepared with difficulty.
• Suzuki and Stille Cross-Coupling Reactions from β-Iodovinylphosphonate: Stereoselective Access to Various Substituted Vinylphosphonates
  作者：Mohamed Abarbri、Emilie Thiery

  DOI：10.1055/s-0034-1378360

  日期：——

  Stereoselective synthesis of beta-arylvinyl, dienyl, and enynylphosphonates was achieved from diethyl 2-iodovinylphosphonate via Suzuki or Stille cross-coupling reactions in good yields.