cinnamyl-phosphinic acid ethyl ester | 1207192-25-3

• 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: cinnamyl-phosphinic acid ethyl ester
• 英文别名: ethyl cinnamyl-H-phosphinate
• CAS: 1207192-25-3
• 化学式: C₁₁H₁₅O₂P
• 分子量: 210.213
• InChiKey: NKAIJALQSJKHON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 cinnamyl-phosphinic acid ethyl ester 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以866 mg的产率得到ethyl cinnamyl (hydroxymethyl)phosphinate
  参考文献：
  名称：

  Chemistry of the Versatile (Hydroxymethyl)phosphinyl P(O)CH₂OH Functional Group

  摘要：

  (Hydroxymethyl)phosphorus compounds are well-known and valuable compounds in general; however the use of (hydroxymethyl)phosphinates (RP)-P-1(O)(OR2)CH2OH in particular has been much more limited. The potential of this functionality has not yet been fully realized because the mild unmasking of the hydroxymethyl group was not available. The mild oxidative conversion of (RP)-P-1(O)(OR2)CH2OH into (RP)-P-1(O)(OR2)H using the Corey-Kim oxidation is described. Other reactions preserving the methylene carbon are also reported.

  DOI：

  10.1021/ol3013793
• 作为产物：
  描述：

  ethyl cinnamyl (hydroxymethyl)phosphinate 在 N-氯代丁二酰亚胺 、 二甲基硫 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.58h， 生成 cinnamyl-phosphinic acid ethyl ester
  参考文献：
  名称：

  Chemistry of the Versatile (Hydroxymethyl)phosphinyl P(O)CH₂OH Functional Group

  摘要：

  (Hydroxymethyl)phosphorus compounds are well-known and valuable compounds in general; however the use of (hydroxymethyl)phosphinates (RP)-P-1(O)(OR2)CH2OH in particular has been much more limited. The potential of this functionality has not yet been fully realized because the mild unmasking of the hydroxymethyl group was not available. The mild oxidative conversion of (RP)-P-1(O)(OR2)CH2OH into (RP)-P-1(O)(OR2)H using the Corey-Kim oxidation is described. Other reactions preserving the methylene carbon are also reported.

  DOI：

  10.1021/ol3013793

文献信息

• DBU-promoted alkylation of alkyl phosphinates and H-phosphonates
  作者：Laurent Gavara、Christelle Petit、Jean-Luc Montchamp

  DOI：10.1016/j.tetlet.2012.07.019

  日期：2012.9

  phosphinates and some H-phosphonate diesters is promoted by the base DBU. Only more reactive alkyl halides react in preparatively useful yields. However, the method provides easy access to important H-phosphinate building blocks, without the need for a protecting group strategy or metal catalysts. The reaction is conveniently conducted at, or below, room temperature. The preparation of methyl-H-phosphinate

  DBU碱促进烷基次膦酸酯和一些H-膦酸酯二酯的烷基化。只有更多的反应性烷基卤化物以制备有用的产率反应。但是，该方法无需重要的保护基策略或金属催化剂即可轻松获得重要的H-次膦酸酯结构单元。该反应方便地在室温或低于室温下进行。甲基的制备ħ -phosphinate酯是特别令人感兴趣的，因为它避免了以往更普遍使用methyldichlorophosphine MePCl的2。
• Facile P,N-heterocycle synthesis via tandem aminomethylation–cyclization of H-phosphinate building blocks
  作者：Clémence Queffélec、Jean-Luc Montchamp

  DOI：10.1039/b917428a

  日期：——

  Various heterocycles containing phosphorus and nitrogen are easily synthesized from readily available H-phosphinate building blocks. Aminomethylation of these H-phosphinates is followed by in situ cyclization through substitution or cross-coupling to produce novel heterocycles in moderate to good yields.

  含磷和氮的多种杂环化合物能够容易地从易得的H-膦酸酯砌块合成。对这些H-膦酸酯进行胺甲基化后，通过取代或交叉耦合进行原位环化，以中等至良好的产率得到新型杂环化合物。
• Temporary Protection of<i>H</i>-Phosphinic Acids as a Synthetic Strategy
  作者：Laëtitia Coudray、Jean-Luc Montchamp

  DOI：10.1002/ejoc.200900694

  日期：2009.9

  H-Phosphinates obtained through various methodologies are protected directly via reaction with triethyl orthoacetate. The resulting products can be manipulated easily, and various synthetic reactions are presented. For example, application to the synthesis of aspartate transcarbamoylase (ATCase) or kynureninase inhibitors are illustrated. Other reactions, such as Sharpless' asymmetric dihydroxylation

  通过各种方法获得的H-膦酸酯可通过与原乙酸三乙酯反应直接得到保护。所得产物易于操作，并提出了各种合成反应。例如，举例说明了在天冬氨酸转氨甲酰酶（ATCase）或犬尿氨酸酶抑制剂的合成中的应用。还展示了其他反应，例如Sharpless的不对称二羟基化反应或Grubbs的烯烃交叉复分解反应。