(E)-1-ethyl-3-trimethylsilyl-2-propenylphosphonate | 282534-05-8

• 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: (E)-1-ethyl-3-trimethylsilyl-2-propenylphosphonate
• 英文别名: [(E)-3-diethoxyphosphorylpent-1-enyl]-trimethylsilane
• CAS: 282534-05-8
• 化学式: C₁₂H₂₇O₃PSi
• 分子量: 278.404
• InChiKey: VWLGLVRZRVRJBV-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  乙酰氯 、 (E)-1-ethyl-3-trimethylsilyl-2-propenylphosphonate 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到diethyl (E)-1-ethyl-4-oxo-2-pentenylphosphonate
  参考文献：
  名称：

  Efficient Approach to 4-Oxo-2-alkenylphosphonates via Regiospecific Friedel−Crafts Acylation

  摘要：

  Treatment of allylic and vinylic phosphonates with excess LiHMDS, followed by addition of chlorotrimethylsilane, afforded alpha- and gamma- silylated allylic phosphonate mixtures. Without separation, these mixtures underwent the Friedel-Crafts reaction and base-promoted isomerization to give 4-oxo-2-alkenylphosphonates, which can serve as building blocks for the construction of polyethylenic chains.

  DOI：

  10.1021/jo0003504
• 作为产物：
  描述：

  烯丙基磷酸二乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (E)-1-ethyl-3-trimethylsilyl-2-propenylphosphonate
  参考文献：
  名称：

  Efficient Approach to 4-Oxo-2-alkenylphosphonates via Regiospecific Friedel−Crafts Acylation

  摘要：

  Treatment of allylic and vinylic phosphonates with excess LiHMDS, followed by addition of chlorotrimethylsilane, afforded alpha- and gamma- silylated allylic phosphonate mixtures. Without separation, these mixtures underwent the Friedel-Crafts reaction and base-promoted isomerization to give 4-oxo-2-alkenylphosphonates, which can serve as building blocks for the construction of polyethylenic chains.

  DOI：

  10.1021/jo0003504

文献信息

• Regioselective alkylation and olefination of allylic carbanion stabilized by two different heteroatoms: phosphorus and silicon
  作者：Bum Sung Lee、Jun Mo Gil、Dong Young Oh

  DOI：10.1016/s0040-4039(01)00170-8

  日期：2001.3

  with LiHMDS, followed by successive addition of chlorotrimethylsilane and carbonyl reagent, afforded dienylsilanes in good yields. 3-Substituted dienylsilanes were obtained by alkylation and olefination of allylic carbanion of 3-trimethylsilylallylphosphonates.

  用LiHMDS处理烯丙基膦酸酯，然后连续加入氯代三甲基硅烷和羰基试剂，以高收率得到二烯基硅烷。通过3-三甲基甲硅烷基烯丙基膦酸酯的烯丙基碳负离子的烷基化和烯化获得3-取代的二烯基硅烷。
• Efficient Approach to 4-Oxo-2-alkenylphosphonates via Regiospecific Friedel−Crafts Acylation
  作者：Bum Sung Lee、Shi Yong Lee、Dong Young Oh

  DOI：10.1021/jo0003504

  日期：2000.6.1

  Treatment of allylic and vinylic phosphonates with excess LiHMDS, followed by addition of chlorotrimethylsilane, afforded alpha- and gamma- silylated allylic phosphonate mixtures. Without separation, these mixtures underwent the Friedel-Crafts reaction and base-promoted isomerization to give 4-oxo-2-alkenylphosphonates, which can serve as building blocks for the construction of polyethylenic chains.