diethyl (2-methyl-5-cyanofuran-3-yl)methylphosphonate

• 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: diethyl (2-methyl-5-cyanofuran-3-yl)methylphosphonate
• 英文别名: diethyl (2-methyl-5-cyanofur-3-yl)methanephosphonate；4-(Diethoxyphosphorylmethyl)-5-methylfuran-2-carbonitrile
• 化学式: C₁₁H₁₆NO₄P
• 分子量: 257.226
• InChiKey: XELAAXHBDSKWFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  72.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (2-methyl-5-cyanofuran-3-yl)methylphosphonate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以96%的产率得到diethyl (2-bromomethyl-5-cyanofur-3-yl)methanephosphonate
  参考文献：
  名称：

  Synthesis of 2-substituted 3,4-bis(diethoxyphosphorylmethyl)furans

  摘要：

  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.

  DOI：

  10.1134/s1070363215020139
• 作为产物：
  描述：

  sodium diethyl phosphite 、 2-methyl-3-chloromethyl-5-cyanofuran 以 苯 为溶剂， 反应 5.0h， 以23%的产率得到diethyl (2-methyl-5-cyanofuran-3-yl)methylphosphonate
  参考文献：
  名称：

  Pevzner, L. M.; Ignat'ev, V. M.; Ionin, B. I., Russian Journal of General Chemistry, 1994, vol. 64, # 1.2, p. 125 - 128

  摘要：

  DOI：

文献信息

• Formylation of alkyl cyanofurylmethanphosphonates at the active methylene group
  作者：L. M. Pevzner

  DOI：10.1134/s1070363213090107

  日期：2013.9

  Alkyl cyanofurylmethanephosphonates are formylated with ethyl formate in the presence of sodium foil to form sodium derivatives of phosphonoacetic aldehyde. If phosphonoacetic aldehyde and nitrile groups occupy remote positions in the furan ring, the sodium derivative in DMSO solution exists in the form of carbanion carrying charge on the carbon atom adjacent to the aldehyde group. If the substituents are located at the adjacent carbons of furan ring, the solution equilibrium between the carbanionic (major product) and Z-enolate forms of salts is established. Alkylation of the formed salts with methyl iodide occurs exclusively at the oxygen atom to give methyl enolates. In most cases, a mixture of E-and Z-isomers is formed, the E one being prevailing. In the case of 2,5-location of the substituents in furan ring, the sodium salt is inactive, and the alkylation does not occur.
• Pevzner, L. M.; Ignat'ev, V. M.; Ionin, B. I., Russian Journal of General Chemistry, 1994, vol. 64, # 1.2, p. 125 - 128
  作者：Pevzner, L. M.、Ignat'ev, V. M.、Ionin, B. I.

  DOI：——

  日期：——
• 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.