ethyl 2-methyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylate | 502990-90-1

• 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-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylate
• 英文别名: Ethyl 2-methyl-4-(diethoxyphosphorylmethyl)-5-t-butylfuran-3-carboxylate；ethyl 5-tert-butyl-4-(diethoxyphosphorylmethyl)-2-methylfuran-3-carboxylate
• CAS: 502990-90-1
• 化学式: C₁₇H₂₉O₆P
• 分子量: 360.387
• InChiKey: ZZGSPZUTJACKEG-UHFFFAOYSA-N

物化性质

• 沸点：
  443.2±45.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylate 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 1.0h， 以90%的产率得到ethyl 2-bromomethyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylate
  参考文献：
  名称：

  摘要：

  Alkyl 2-methyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylates are selectively brominated with N-bromosuccinimide at the methyl group in position 2 of the ring. The resulting bromomethyl derivatives react with secondary amines to form tertiary amines and with sodium butylthiolate in methanol to form the corresponding sulfide. The reaction with potassium thiocyanate in DMF at 80degreesC gives a mixture of thiocyanate and isothiocyanate. When treated with phenolate or alcoholate ions, the bromo-methylfurans decompose.

  DOI：

  10.1023/a:1025669326432
• 作为产物：
  描述：

  2-methyl-5-(tert-butyl)furan-3-carboxylic acid ethyl ester 在 盐酸 、 zinc(II) chloride 作用下， 以 氯仿 、 苯 为溶剂， 反应 16.0h， 生成 ethyl 2-methyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylate
  参考文献：
  名称：

  摘要：

  3-Ethoxycarbonyl- and 3-acetyl-2-methyl-5-tert-butylfurans undergo chloromethylation under the unusually rigorous conditions (55-60degreesC, 3-3.5 h). The corresponding diethylamide and nitrite were prepared by standard modification of the carboxy group. In phosphorylation of the resulting chloromethylfurans under the conditions of the Michaelis-Becker reaction, in the case of the ester and diethylamide, the phosphonate yields were close to those obtained with compounds containing no tert-butoxy group, and in the case of acetylfuran the yield was even somewhat higher. On the contrary, the chloromethylated nitrite reacts considerably more slowly than all the other compounds under consideration and than the similar compound containing no tert-butyl substituent. Thus,,the effect of the tert-butyl group in the a-position of the furan ring is clearly pronounced in the electrophilic substitutions in the neighboring position of the heteroring. When the reaction center is located in the side chain (substitution of chlorine), the effect of the bulky substituent is manifested only in special cases and can be attributed to the presence of a conformation in which the chloromethyl group is shielded.

  DOI：

  10.1023/a:1020750715942