N-methyl-N-<(trimethylsilyl)methyl>-2-furanamide | 143266-39-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methyl-N-<(trimethylsilyl)methyl>-2-furanamide
• 英文别名: N-methyl-N-(trimethylsilylmethyl)furan-2-carboxamide
• CAS: 143266-39-1
• 化学式: C₁₀H₁₇NO₂Si
• 分子量: 211.336
• InChiKey: FIFBHMIDIMDGOY-UHFFFAOYSA-N

物化性质

• 沸点：
  282.0±20.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-N-<(trimethylsilyl)methyl>-2-furanamide 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 正丁基锂 、 cesium fluoride 作用下， 以 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 3.5h， 生成 3-<(dimethylamino)methyl>-4-(α-hydroxybenzyl)-2-methylfuran
  参考文献：
  名称：

  Rearrangement of dimethyl(furylmethyl)ammonium and dimethyl(thienylmethyl)ammonium N-methylides. Isolation and reaction of nonaromatic intermediates

  摘要：

  3-[(Dimethylamino)methyl]-2-methylene-2,3-dihydrofuran (5o) and 2-[(dimethylamino)methyl]-3-methylene-2,3-dihydrofuran (12o) and their thiophene analogues 5s and 12s were prepared in high yields by fluoride-ion induced desilylation of NN-dimethyl-N-[(trimethylsilyl)methyl](2-furylmethyl)ammonium (3o) and -(3-furylmethyl)ammonium iodides (10o) and their thienylmethyl analogues 3s and 10s. Compound 59 or 12s was successfully converted to 3-[(dimethylamino)methyl](2-thienylmethyl)lithium (23s) or 2-[(dimethyl-amino)methyl](3-thienylmethyl)lithium (26s), which reacted with aldehydes to give [(dimethylamino)-methyl)(2-hydroxyalkyl)thiophenes 259 or 27s, respectively.

  DOI：

  10.1021/jo00046a025
• 作为产物：
  描述：

  呋喃甲酰氯 、 N-(trimethylsilylmethyl)methylamine 在 sodium hydroxide 作用下， 反应 1.0h， 以92%的产率得到N-methyl-N-<(trimethylsilyl)methyl>-2-furanamide
  参考文献：
  名称：

  Rearrangement of dimethyl(furylmethyl)ammonium and dimethyl(thienylmethyl)ammonium N-methylides. Isolation and reaction of nonaromatic intermediates

  摘要：

  3-[(Dimethylamino)methyl]-2-methylene-2,3-dihydrofuran (5o) and 2-[(dimethylamino)methyl]-3-methylene-2,3-dihydrofuran (12o) and their thiophene analogues 5s and 12s were prepared in high yields by fluoride-ion induced desilylation of NN-dimethyl-N-[(trimethylsilyl)methyl](2-furylmethyl)ammonium (3o) and -(3-furylmethyl)ammonium iodides (10o) and their thienylmethyl analogues 3s and 10s. Compound 59 or 12s was successfully converted to 3-[(dimethylamino)methyl](2-thienylmethyl)lithium (23s) or 2-[(dimethyl-amino)methyl](3-thienylmethyl)lithium (26s), which reacted with aldehydes to give [(dimethylamino)-methyl)(2-hydroxyalkyl)thiophenes 259 or 27s, respectively.

  DOI：

  10.1021/jo00046a025

文献信息

• Rearrangement of dimethyl(furylmethyl)ammonium and dimethyl(thienylmethyl)ammonium N-methylides. Isolation and reaction of nonaromatic intermediates
  作者：Takeshi Usami、Naohiro Shirai、Yoshiro Sato

  DOI：10.1021/jo00046a025

  日期：1992.9

  3-[(Dimethylamino)methyl]-2-methylene-2,3-dihydrofuran (5o) and 2-[(dimethylamino)methyl]-3-methylene-2,3-dihydrofuran (12o) and their thiophene analogues 5s and 12s were prepared in high yields by fluoride-ion induced desilylation of NN-dimethyl-N-[(trimethylsilyl)methyl](2-furylmethyl)ammonium (3o) and -(3-furylmethyl)ammonium iodides (10o) and their thienylmethyl analogues 3s and 10s. Compound 59 or 12s was successfully converted to 3-[(dimethylamino)methyl](2-thienylmethyl)lithium (23s) or 2-[(dimethyl-amino)methyl](3-thienylmethyl)lithium (26s), which reacted with aldehydes to give [(dimethylamino)-methyl)(2-hydroxyalkyl)thiophenes 259 or 27s, respectively.