ethyl 2-methyl-3-<(diethoxyphosphinyl)methyl>furan-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 2-methyl-3-<(diethoxyphosphinyl)methyl>furan-5-carboxylate
• 英文别名: diethyl (2-methyl-5-ethoxycarbonylfur-3-yl)methanephosphonate；ethyl 4-diethoxyphosphinoylmethyl-5-methylfuran-2-carboxylate；diethyl <(3-furyl)methyl>phosphonate；Ethyl 4-(diethoxyphosphorylmethyl)-5-methylfuran-2-carboxylate
• 化学式: C₁₃H₂₁O₆P
• 分子量: 304.28
• InChiKey: IXWZBJPZMDSVAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-3-<(diethoxyphosphinyl)methyl>furan-5-carboxylate 在 sodium 、 碳酸二乙酯 、 盐酸 、 水 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以0.2 g的产率得到4-(diethoxyphosphorylmethyl)-5-methylfuran-2-carboxylic acid
  参考文献：
  名称：

  在钠箔存在下（乙氧基羰基呋喃基）甲烷膦酸酯与碳酸二乙酯的反应

  摘要：

  研究了钠箔存在下（乙氧基羰基呋喃基）甲烷膦酸酯与碳酸二乙酯的反应。结果表明，如果酸化基团与2-呋喃基甲烷膦酸酯的碳负离子中心共轭，则将碳负离子加到碳酸二乙酯的羰基上可以高产率地得到2-呋喃基乙酸衍生物。合成，分离和表征这些CH-酸的钠盐。用溴乙酸烷基酯进行它们的烷基化。如果乙氧羰基不与碳负离子中心共轭，则起始膦酸酯的转化率和加合物的产率急剧降低。在用碳酸二乙酯酰化之后，立即将烷基（2-和4-乙氧基羰基糠-3-基）甲烷膦酸酯用碳酸二乙酯钠系统还原，以形成烷基1-（2-和4-乙氧基羰基糠-3-基）乙烷膦酸酯。中间还原产物的形成，磷酸化的呋喃基乙醛也经光谱固定。与起始膦酸酯和1-（3-呋喃基）乙烷膦酸酯烷基酯的酯基的还原脱烷基同时发生，得到羧酸盐。（2-甲基-5-乙氧基羰基呋喃-3-基）甲烷膦烷基酯不参与缩合反应。它仅产生在碳酸二乙酯形成的乙醇酸钠作用下的脱烷基化产物。与起始膦酸酯和1-（3-呋

  DOI：

  10.1134/s1070363214070159
• 作为产物：
  描述：

  ethyl 4-acetoxymethyl-5-bromomethylfuran-2-carboxylate 以 苯 为溶剂， 反应 13.0h， 生成 ethyl 2-methyl-3-<(diethoxyphosphinyl)methyl>furan-5-carboxylate
  参考文献：
  名称：

  Pevzner, L. M.; Ignat'ev, V. M.; Ionin, B. I., Russian Journal of General Chemistry, 1994, vol. 64, # 7.1, p. 1000 - 1004

  摘要：

  DOI：

文献信息

• Pevzner, L. M.; Ignat'ev, V. M.; Ionin, B. I., Journal of general chemistry of the USSR, 1992, vol. 62, # 4.1, p. 658 - 662
  作者：Pevzner, L. M.、Ignat'ev, V. M.、Ionin, B. I.

  DOI：——

  日期：——
• Enol phosphates of phosphorylated derivatives of furylacetic aldehyde and furylpiruvic acid
  作者：L. M. Pevzner

  DOI：10.1134/s1070363214110188

  日期：2014.11

  Phosphorylated derivatives of isomeric furylacetic aldehydes and furylpiruvic acids have been synthesized via formylation and oxalylation of dialkyl (ethoxycarbonylfuryl)methanephosphonates under conditions of the Claisen reaction. H-1, C-13, and P-31 NMR spectroscopy studies have shown that the products exist as equilibrium mixtures of the carbonyl compounds and its E- and Z-enol forms in chloroform solutions. Acylation of these substances with diethyl chlorophosphate has yielded the corresponding enol phosphates. Influence of the substituents location in the furan ring on predominance of cis- or trans-configuration has been demonstrated.
• Acylation of diethyl (ethoxycarbonylfuryl)methanephosphonates under the conditions of claisen reaction
  作者：L. M. Pevzner

  DOI：10.1134/s1070363212120067

  日期：2012.12

  O,O-Diethyl (ethoxycarbonylfuryl)methanephosphonates are formylated with ethyl formate in the presence of sodium foil at the methylene group adjacent to phosphorus atom to form sodium salts of phosphonoacetic aldehyde. When the substituents in the furan ring are remote from one another, and also in the case of 3, 4-disubstituted isomer these salts in DMSO solution exist in the carbanion form. Anions of salts of (2-ethoxycarbonylfur-3-yl)phosphonoacetic aldehyde and the isomer with the reversed location of substituents in DMSO solution take part in the dynamic equilibrium between the carbanion and the enolate form. The alkylation of all salts obtained with allyl bromide and dimethyl sulfate proceeds exclusively at the oxygen to form a mixture of Z- and E-isomers of phosphorylated vinyl ethers.
• Synthesis of 2-substituted 3,4-bis(diethoxyphosphorylmethyl)furans
  作者：L. M. Pevzner

  DOI：10.1134/s1070363215020139

  日期：2015.2

  Bromination of ethyl 4-(diethoxyphosphorylmethyl)-5-methylfuran-2-carboxylate and 4-(diethoxyphosphorylmethyl)-5-methylfuran-2-carbonitrile with N-bromosuccinimide followed by phosphorylation via the Arbuzov reaction have yielded the corresponding 2-substituted 4,5-bis(diethoxyphosphorylmethyl)furans. Synthesis and transformations of bisphosphorylated 2-furoic acid and its derivatives are described.
• Pevzner, L. M.; Ignat'ev, V. M.; Ionin, B. I., Russian Journal of General Chemistry, 1994, vol. 64, # 7.1, p. 1000 - 1004
  作者：Pevzner, L. M.、Ignat'ev, V. M.、Ionin, B. I.

  DOI：——

  日期：——