N-Methyl-N-<(trimethylsilyl)methyl>acetamide | 164024-96-8

• 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>acetamide
• 英文别名: N-methyl-N-((trimethylsilyl)methyl)acetamide；N-methyl-N-(trimethylsilylmethyl)acetamide
• CAS: 164024-96-8
• 化学式: C₇H₁₇NOSi
• 分子量: 159.304
• InChiKey: WJZGTKRVCVBPME-UHFFFAOYSA-N

物化性质

• 沸点：
  196.4±23.0 °C(Predicted)
• 密度：
  0.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丙烯酸丁酯 、 N-Methyl-N-<(trimethylsilyl)methyl>acetamide 在 palladium diacetate 、 溶剂黄146 、 对苯醌 作用下， 反应 6.0h， 以90%的产率得到巴豆酸丁酯
  参考文献：
  名称：

  在藤原-莫里塔尼氧化偶联反应中，催化酰胺介导的从硅烷到烯烃的甲基转移。

  摘要：

  DOI：

  10.1002/anie.200800815
• 作为产物：
  描述：

  N-甲基乙酰胺 、 碘甲基三甲基硅烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以46%的产率得到N-Methyl-N-<(trimethylsilyl)methyl>acetamide
  参考文献：
  名称：

  Investigations of Novel Azomethine Ylide-Forming Photoreactions of N-Silylmethylimides

  摘要：

  The scope of a recently discovered (Yoon, E. C. et al. J. Am. Chem. Sec. 1995, 117, 2698), azomethine ylide-forming photoreaction has been explored by probing the excited state chemistry of several N-trimethylsilylmethyl substituted cyclic and acyclic imides and amide analogs. Photolysis of N-[(trimethylsilyl)methyl]maleimide (4) in acetonitrile leads to efficient production of the tricyclic product 16, formed by trapping of the photogenerated azomethine ylide intermediate 15 through cydoaddition with 4. Irradiation 4 in solutions containing high concentrations of the dipolarophiles, acrylonitrile or fumaronitrile, results in production of the products (19-21 and 23-24, respectively) arising by cycloaddition of the ylide 15 with the added dipolarophiles. In contrast, photolysis of the nonconjugated cyclic imide, N-[(trimethylsilyl)methyl]succinimide (5), brings about N-acyl migration resulting in the exclusive production of the unstable, iminolactone 30. On the other hand, acyclic, N-trimethylsilylmethyl aroyl imides 6-8 undergo the excited state C to O silyl migration reaction to produce azomethine ylide intermediates 35. Both in the presence or absence of added dipolarophiles, these ylides undergo electrocyclization to form transient aziridine intermediates 36 which react further by ring opening to generate N-phenacylamide products 32-34. In contrast, the nonconjugated imide, N-[(trimethylsilyl)methyl]-N-acetylacetamide (9), is unreactive upon irradiation. Similarly, simple N-[(trimethylsilyl)methyl] amides 10-13, while being photochemically labile, do not react to form ''trappable'' ylide intermediates upon irradiation. The results outlined above are presented and discussed in terms of the scope and limitations of the new, azomethine ylide-forming photoreaction of silylmethyl imides.

  DOI：

  10.1021/jo00113a012

文献信息

• Tetrabutylammonium Decatungstate (Chemo)selective Photocatalyzed, Radical CH Functionalization in Amides
  作者：Simone Angioni、Davide Ravelli、Daniele Emma、Daniele Dondi、Maurizio Fagnoni、Angelo Albini

  DOI：10.1002/adsc.200800378

  日期：2008.10.6

  Photoamidation of electron-poor olefins has been achieved by means of a radical-induced CH functionalization in amides. Tetrabutylammonium decatungstate was used as photocatalyst of the reaction and allowed the smooth generation of different carbon-centered radicals depending on the amide structure.

  贫电子烯烃的光酰胺化是通过酰胺中自由基诱导的CH官能化实现的。使用四丁基癸酸铵作为反应的光催化剂，根据酰胺的结构，可以平稳地生成不同的以碳为中心的自由基。
• Investigations of Novel Azomethine Ylide-Forming Photoreactions of N-Silylmethylimides
  作者：Ung Chan Yoon、Sung Ju Cho、Yean-Jang Lee、Maria J. Mancheno、Patrick S. Mariano

  DOI：10.1021/jo00113a012

  日期：1995.4

  The scope of a recently discovered (Yoon, E. C. et al. J. Am. Chem. Sec. 1995, 117, 2698), azomethine ylide-forming photoreaction has been explored by probing the excited state chemistry of several N-trimethylsilylmethyl substituted cyclic and acyclic imides and amide analogs. Photolysis of N-[(trimethylsilyl)methyl]maleimide (4) in acetonitrile leads to efficient production of the tricyclic product 16, formed by trapping of the photogenerated azomethine ylide intermediate 15 through cydoaddition with 4. Irradiation 4 in solutions containing high concentrations of the dipolarophiles, acrylonitrile or fumaronitrile, results in production of the products (19-21 and 23-24, respectively) arising by cycloaddition of the ylide 15 with the added dipolarophiles. In contrast, photolysis of the nonconjugated cyclic imide, N-[(trimethylsilyl)methyl]succinimide (5), brings about N-acyl migration resulting in the exclusive production of the unstable, iminolactone 30. On the other hand, acyclic, N-trimethylsilylmethyl aroyl imides 6-8 undergo the excited state C to O silyl migration reaction to produce azomethine ylide intermediates 35. Both in the presence or absence of added dipolarophiles, these ylides undergo electrocyclization to form transient aziridine intermediates 36 which react further by ring opening to generate N-phenacylamide products 32-34. In contrast, the nonconjugated imide, N-[(trimethylsilyl)methyl]-N-acetylacetamide (9), is unreactive upon irradiation. Similarly, simple N-[(trimethylsilyl)methyl] amides 10-13, while being photochemically labile, do not react to form ''trappable'' ylide intermediates upon irradiation. The results outlined above are presented and discussed in terms of the scope and limitations of the new, azomethine ylide-forming photoreaction of silylmethyl imides.
• Catalytic Amide-Mediated Methyl Transfer from Silanes to Alkenes in Fujiwara–Moritani Oxidative Coupling
  作者：Waqar Rauf、John M. Brown

  DOI：10.1002/anie.200800815

  日期：2008.5.19