3-(diethoxyphosphorylmethyl)-5-tert-butylfuran | 790713-47-2

• 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: 3-(diethoxyphosphorylmethyl)-5-tert-butylfuran
• 英文别名: Phosphonic acid, [[5-(1,1-dimethylethyl)-3-furanyl]methyl]-, diethyl ester；2-tert-butyl-4-(diethoxyphosphorylmethyl)furan
• CAS: 790713-47-2
• 化学式: C₁₃H₂₃O₄P
• 分子量: 274.297
• InChiKey: MDMRBTFLLNCBBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二甲基氯烯亚胺 、 3-(diethoxyphosphorylmethyl)-5-tert-butylfuran 以 乙腈 为溶剂， 以44%的产率得到5-tert-butyl-3-(diethoxyphosphorylmethyl)-2-(dimethylaminomethyl)furan
  参考文献：
  名称：

  Aminomethylation of 2- and 3-(Diethoxyphosphorylmethyl)furans

  摘要：

  Dimethyl(methylene)ammonium chloride reacts with 2- and 3-(diethoxyphosphorylmethyl)furans by the free alpha position of the furan ring to give the corresponding aminomethyl derivatives. 2,5-Disubstituted furans do not enter this reaction.

  DOI：

  10.1023/b:rugc.0000039082.14939.56
• 作为产物：
  描述：

  methyl 3-bromomethyl-5-tert-butylfuran-2-carboxylate 在 氢氧化钾 、 溴 、 sodium methylate 、 三苯基膦 、 copper(II) oxide 作用下， 以 喹啉 、 水 、 乙腈 、 苯 为溶剂， 反应 17.0h， 生成 3-(diethoxyphosphorylmethyl)-5-tert-butylfuran
  参考文献：
  名称：

  Synthesis and Phosphorylation of 2-, 3-, and 4-Halomethyl-5-tert-butylfurans

  摘要：

  Synthetic methods for preparing of 2-, 3-, and 4-halomethyl-5-tert-butylfurans are developed. It was established that the bromination of 3- and 4-methyl-2-tert-butylfurans with N-bromosuccinimide proceeds mainly at the free alpha-position of the furan ring, and not at the methyl group. Therefore, the target halomethylfurans were prepared through the corresponding 3- and 4-methoxymethyl derivatives. The obtained five products were phosphorylated with sodium diethyl phosphite under the conditions of the Michaelis-Becker reaction to give the corresponding phosphonates.

  DOI：

  10.1023/b:rugc.0000031868.97123.e1

文献信息

• Synthesis and Phosphorylation of 2-, 3-, and 4-Halomethyl-5-tert-butylfurans
  作者：L. M. Pevzner

  DOI：10.1023/b:rugc.0000031868.97123.e1

  日期：2004.4

  Synthetic methods for preparing of 2-, 3-, and 4-halomethyl-5-tert-butylfurans are developed. It was established that the bromination of 3- and 4-methyl-2-tert-butylfurans with N-bromosuccinimide proceeds mainly at the free alpha-position of the furan ring, and not at the methyl group. Therefore, the target halomethylfurans were prepared through the corresponding 3- and 4-methoxymethyl derivatives. The obtained five products were phosphorylated with sodium diethyl phosphite under the conditions of the Michaelis-Becker reaction to give the corresponding phosphonates.
• Aminomethylation of 2- and 3-(Diethoxyphosphorylmethyl)furans
  作者：L. M. Pevzner

  DOI：10.1023/b:rugc.0000039082.14939.56

  日期：2004.5

  Dimethyl(methylene)ammonium chloride reacts with 2- and 3-(diethoxyphosphorylmethyl)furans by the free alpha position of the furan ring to give the corresponding aminomethyl derivatives. 2,5-Disubstituted furans do not enter this reaction.