5-Tert-butyl-3-(chloromethyl)-2-methylfuran | 442686-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 5-Tert-butyl-3-(chloromethyl)-2-methylfuran
• CAS: 442686-59-1
• 化学式: C₁₀H₁₅ClO
• 分子量: 186.681
• InChiKey: PCSVEQOYQFECFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二乙基亚磷酸氢酯 、 5-Tert-butyl-3-(chloromethyl)-2-methylfuran 在 sodium 作用下， 以 苯 为溶剂， 反应 16.0h， 以48%的产率得到5-tert-butyl-3-(diethoxyphosphorylmethyl)-2-methylfuran
  参考文献：
  名称：

  摘要：

  2-Halomethyl derivatives of 3-functionalized 5-tert-butylfurans are phosphorylated under conditions of the Michaelis-Becker and Arbuzov reactions similarly to other halomethylfurans. No effect of the tert-butyl substituent on the yield of the reaction products was found in this case. Contrary to that, the 2-methoxymethyl derivative of 3-chloromethyl-5-tert-butylfuran proved to be more thermostable than its analog containing no tert-butyl substituent. As a result, the yield of phosphonate in the Michaelis-Becker reaction under similar conditions increases 2.5 times. The observed stabilization of the furan ring is explained by shielding of its oxygen atom by the tert-butyl group.

  DOI：

  10.1023/a:1015324824425
• 作为产物：
  描述：

  (5-tert-Butyl-2-methyl-3-furyl)methyl alcohol 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 5-Tert-butyl-3-(chloromethyl)-2-methylfuran
  参考文献：
  名称：

  摘要：

  2-Halomethyl derivatives of 3-functionalized 5-tert-butylfurans are phosphorylated under conditions of the Michaelis-Becker and Arbuzov reactions similarly to other halomethylfurans. No effect of the tert-butyl substituent on the yield of the reaction products was found in this case. Contrary to that, the 2-methoxymethyl derivative of 3-chloromethyl-5-tert-butylfuran proved to be more thermostable than its analog containing no tert-butyl substituent. As a result, the yield of phosphonate in the Michaelis-Becker reaction under similar conditions increases 2.5 times. The observed stabilization of the furan ring is explained by shielding of its oxygen atom by the tert-butyl group.

  DOI：

  10.1023/a:1015324824425