戊酸,2-(二乙氧基氧膦基)-4-羰基-,乙基酯 | 114929-91-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 戊酸,2-(二乙氧基氧膦基)-4-羰基-,乙基酯
• 英文名称: 2-(diethoxyphosphoryl)-4-oxopentanoic acid ethyl ester
• 英文别名: ethyl 2-diethoxyphosphoryl-4-oxopentanoate；Pentanoic acid, 2-(diethoxyphosphinyl)-4-oxo-, ethyl ester
• CAS: 114929-91-8
• 化学式: C₁₁H₂₁O₆P
• 分子量: 280.258
• InChiKey: PYYUVOOVTMGHRU-UHFFFAOYSA-N

物化性质

• 沸点：
  382.5±32.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  戊酸,2-(二乙氧基氧膦基)-4-羰基-,乙基酯 在 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以94%的产率得到4-diethoxyphosphoryl-6-methylpyridazin-3(2H)-one
  参考文献：
  名称：

  新的，简单的和通用的4,6-二取代哒嗪-3（2H）-one的合成。

  摘要：

  描述了由2-二乙氧基磷酰基-4-氧代链烷酸酯和肼开始的4,6-二取代哒嗪-3（2H）-ones的简单，两步合成方法。以这种方式获得的中间体4-二乙氧基磷酰基-4，5-二氢哒嗪-3（2H）-酮用于醛的霍纳-沃兹沃思-埃蒙斯烯化反应以得到各种二取代的哒嗪-3（2H）-酮。

  DOI：

  10.1039/b718734c
• 作为产物：
  描述：

  ethyl 2-diethoxyphosphinoylacrylate 在 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 27.17h， 生成 戊酸,2-(二乙氧基氧膦基)-4-羰基-,乙基酯
  参考文献：
  名称：

  2-Diethoxyphosphoryl-4-nitroalkanoates - Versatile Intermediates in the ­Synthesis of α-Alkylidene-γ-lactones and Lactams

  摘要：

  将各种硝基烷烃 7a-f 与(2-二乙氧基磷酰)丙烯酸乙酯 (6) 迈克尔加成，可得到 2-二乙氧基磷酰-4-硝基烷酸酯 8a-f。将硝基官能团转化为羟基或氨基并环化后，分别得到 3-(二乙氧基磷酰)四氢-2-呋喃酮 11a-e 或 3-(二乙氧基磷酰)吡咯烷-2-酮 14a-e。然后将这些化合物用于霍纳-沃兹沃斯-艾蒙斯醛的烯化反应，得到 3-亚烷基二氢呋喃-2-酮 12a-e 或 17a-c，以及 3-亚甲基吡咯烷-2-酮 15a-e。

  DOI：

  10.1055/s-2004-835656

文献信息

• A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner–Wadsworth–Emmons reaction
  作者：Henryk Krawczyk、Katarzyna Wąsek、Jacek Kędzia、Jakub Wojciechowski、Wojciech M. Wolf

  DOI：10.1039/b712145h

  日期：——

  The synthesis of α-, β- and γ-substituted α-phosphono-γ-lactones was accomplished using different ring closure and ring homologation strategies. It was found that the lactones could be selectively transformed into the corresponding ethyl cyclopropanecarboxylates by treatment with sodium ethoxide in boiling THF. The reported reaction provides an attractive alternative to the classical homologous Horner–Wadsworth–Emmons approach to the construction of cyclopropanes with electron-withdrawing functionalities.

  通过不同的环闭合和环同系化策略，成功合成了α-、β-和γ-取代的α-磷酸-γ-内酯。研究发现，这些内酯可以通过在沸腾的四氢呋喃中用乙醇钠处理，选择性地转化为相应的乙基环丙烷羧酸酯。所报道的反应为构建带有吸电子功能的环丙烷提供了一种吸引人的替代方法，超越了经典的同系化Horner-Wadsworth-Emmons方法。
• ACTION DU DIETHYLPHOSPHITE ET DE LA P-CHLORODIPHENYLPHOSPHINE SUR LES β-ACYLACRYLATES ET LES 2-ENE-1,4-DIONES: SYNTHESE DE γβ'-CETOESTERPHOSPHONATES ET DE 3-(DIPHENYLPHOSPHINEOXDE)-FURANES
  作者：Soufiane Touil、Hedi Zantour

  DOI：10.1080/10426509708031606

  日期：1997.12.1

  p-chlorodiphenylphosphine react with β-acylacrylates to give γ,β'-ketoester-phosphonates 2 and 2′. When reacted with 2-ene-1,4-diones, in the same conditions, p-chlorodiphenylphosphine leads directely to 3-(diphenylphosphineoxide)-furans 4. The structure of all obtained products is confirmed by NMR and IR spectroscopy.

  摘要 亚磷酸二乙酯和对氯二苯基膦与 β-丙烯酸酯反应生成 γ,β'-酮酯膦酸酯 2 和 2'。当与 2-ene-1,4-二酮反应时，在相同条件下，对氯二苯基膦直接生成 3-(二苯基氧化膦)-呋喃 4。所有所得产物的结构均通过 NMR 和 IR 光谱证实。
• A Simple and Efficient Synthesis of 2-Substituted 3-Diethylphosphono 5-Methylfurans
  作者：Isabelle Truel、Abdourahman Mohamed-Hachi、Elie About-Jaudet、Noël Collignon

  DOI：10.1080/00397919708003353

  日期：1997.4

  An efficient carbanionic synthesis of the phosphonic dicarbonylated compounds 2 was achieved and used as key intermediates in the synthesis of the phosphonic furans 4 by acid-induced Paal-Knorr cyclization reaction.
• Novel Synthesis, Cytotoxic Evaluation, and Structure−Activity Relationship Studies of a Series of α-Alkylidene-γ-lactones and Lactams
  作者：Tomasz Janecki、Edyta Błaszczyk、Kazimierz Studzian、Anna Janecka、Urszula Krajewska、Marek Różalski

  DOI：10.1021/jm048970a

  日期：2005.5.1

  5-Alkyl- and 5-arylalkyl-3-methylenedihydrofuran-2-ones 13a-e, 3-alkylidenedihydrofuran-2-ones 18a-c, and 3-methylenepyrrolidin-2-ones 16a-e were synthesized utilizing ethyl 2-diethoxyphosphoryl-4-nitroalkanoates 9a-e as common intermediates. All obtained compounds were tested against L-1210, HL-60, and NALM-6 leukemia cells. The highest cytotoxic activity was observed for 3-methylenefuranones 13d,e bearing benzyl or 3,4-dimethoxyphenylmethyl substituents at position 5, with IC50 values of 5.4 and 6.0 mu M, respectively. Contrary to the literature reports, no enhancement in activity due to the presence of a hydroxy group was found when the cytotoxicity of furanones 13a,b,d and 5-(1'-hydroxyalkyl)-3-methylenedihydrofuran-2-ones 6a,b,d was compared. The anticancer activity of pyrrolidinones 16a-e and 3-alkylidenefuranones 18a-c was much weaker than that of furanones 13a-e.
• ACTION DES HYDRAZINES SUR LES γ,β'-DICARBONYLPHOSPHONATES ET PHOSPHINEOXIDES: SYNTHESE DE 4-PHOSPHOPYRIDAZINES ET PYRIDAZIN-3-ONES
  作者：Soufiane Touil、Hedi Zantour

  DOI：10.1080/10426509808043626

  日期：1998.3.1

  gamma,beta'-Dicarbonylphosphonates and phosphincoxides 1 and 2 react with hydrazines to give 4-phosphopyridazine and pyridazin-3-one derivatives 3, 4 and 5, 4-Phosphodihydro-pyridazin-3-ones 5 were dehydrogenated by the action of bromine in acetic acid to give phosphopyridazinones 6. The structure of all obtained products is confirmed by NMR and IR spectroscopy.