2-methyl-4-chloromethyl-5-tert-butylfuran-3-carbonitrile | 502990-88-7

• 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: 2-methyl-4-chloromethyl-5-tert-butylfuran-3-carbonitrile
• 英文别名: 5-tert-butyl-4-(chloromethyl)-2-methylfuran-3-carbonitrile
• CAS: 502990-88-7
• 化学式: C₁₁H₁₄ClNO
• 分子量: 211.691
• InChiKey: RIQYIONWGPYZPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  36.93
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  sodium diethyl phosphite 、 2-methyl-4-chloromethyl-5-tert-butylfuran-3-carbonitrile 以 苯 为溶剂， 反应 10.0h， 以39%的产率得到2-methyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carbonitrile
  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
• 作为产物：
  描述：

  5-叔丁基-4-羟基甲基-2-甲基-呋喃-3-羧酸 在 氯化亚砜 、 五氯化磷 、 氨 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 11.5h， 生成 2-methyl-4-chloromethyl-5-tert-butylfuran-3-carbonitrile
  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