ethyl 2-{[methoxy(phenyl)phosphoryl]methyl}acrylate

• 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 2-{[methoxy(phenyl)phosphoryl]methyl}acrylate
• 英文别名: Ethyl 2-[[methoxy(phenyl)phosphoryl]methyl]prop-2-enoate
• 化学式: C₁₃H₁₇O₄P
• 分子量: 268.249
• InChiKey: VDCHRTHCZMOMNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-{[methoxy(phenyl)phosphoryl]methyl}acrylate 在 偶氮二异丁腈 、 sodium cyanoborohydride 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 25.0h， 生成 C₂₂H₂₈NO₆P
  参考文献：
  名称：

  Late-Stage Diversification of Phosphinic Dehydroalanine Pseudopeptides Based on a Giese-Type Radical C-Alkylation Strategy

  摘要：

  A straightforward, late-stage diversification strategy for the installation of side chains on readily accessible unsaturated phosphinopeptidic scaffolds based on a Giese-type addition of alkyl radicals has been investigated. Among different alternatives, the preferred methodology is operationally simple as it can be carried out in an open flask with no need for protection of acidic moieties. Direct application to the synthesis of SPPS-compatible building blocks or to longer peptides is also reported.

  DOI：

  10.1021/acs.orglett.9b00857
• 作为产物：
  描述：

  2-(morpholin-4-ylmethyl)acrylate d'ethyle 以 甲醇 、 苯 为溶剂， 反应 6.0h， 生成 ethyl 2-{[methoxy(phenyl)phosphoryl]methyl}acrylate
  参考文献：
  名称：

  NOUVELLES VOIES D'ACCES AUX 2-ETHOXYCARBONYLALLYLPHONATES

  摘要：

  Michaelis-Arbusov 反应（方法 A）和亚磷酸二烷基酯的亲核加成，然后是 Hoffman 烯化（方法 B）代表了两种合成方法，从容易获得的乙基 2-(N ,N-二烷基氨基甲基)丙烯酸酯 1.

  DOI：

  10.1080/10426500490257005

文献信息

• Late-Stage Diversification of Phosphinic Dehydroalanine Pseudopeptides Based on a Giese-Type Radical C-Alkylation Strategy
  作者：Kostas Voreakos、Laurent Devel、Dimitris Georgiadis

  DOI：10.1021/acs.orglett.9b00857

  日期：2019.6.21

  A straightforward, late-stage diversification strategy for the installation of side chains on readily accessible unsaturated phosphinopeptidic scaffolds based on a Giese-type addition of alkyl radicals has been investigated. Among different alternatives, the preferred methodology is operationally simple as it can be carried out in an open flask with no need for protection of acidic moieties. Direct application to the synthesis of SPPS-compatible building blocks or to longer peptides is also reported.
• NOUVELLES VOIES D'ACCES AUX 2-ETHOXYCARBONYLALLYLPHOSPHONATES
  作者：Hédi Mrabet、Hédi Zantour

  DOI：10.1080/10426500490257005

  日期：2004.1

  The Michaelis-Arbusov reaction (method A) and the nucleophilic addition of dialkylphosphites followed by Hoffman olefination (method B) represent two synthetic methods giving a variety of 2-ethoxycarbonylallyl-phosphonates 2, in good yields, from readily accessible ethyl 2-(N,N-dialkylaminomethyl) acrylates 1.

  Michaelis-Arbusov 反应（方法 A）和亚磷酸二烷基酯的亲核加成，然后是 Hoffman 烯化（方法 B）代表了两种合成方法，从容易获得的乙基 2-(N ,N-二烷基氨基甲基)丙烯酸酯 1.