N-[(3aR,5S,6S,6aR)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-2,2,2-trichloro-acetamide | 906357-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(3aR,5S,6S,6aR)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-2,2,2-trichloro-acetamide
• 英文别名: N-[(3aR,5S,6S,6aR)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-ethenyl-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]-2,2,2-trichloroacetamide
• CAS: 906357-07-1
• 化学式: C₁₈H₃₀Cl₃NO₅Si
• 分子量: 474.884
• InChiKey: CQMMHWKJIPMRSZ-ZHRONYKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(3aR,5S,6S,6aR)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-2,2,2-trichloro-acetamide 在 四丁基氯化铵 、 sodium carbonate 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(3aR,5S,6S,6aR)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester
  参考文献：
  名称：

  One-Pot Transformation of Trichloroacetamide into Readily Deprotectable Carbamates

  摘要：

  A trichloroacetamide group was converted to an isocyanate, which was in situ captured by a variety of alcohols in the presence of CuCl and n-BuN4Cl to afford the corresponding carbamates. The scope and limitation of this transformation are also described.

  DOI：

  10.1021/ol061123c
• 作为产物：
  描述：

  2,2,2-Trichloro-N-[(3aR,5S,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetamide 在 咪唑 、 sodium tetrahydroborate 、 高碘酸 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(3aR,5S,6S,6aR)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-2,2,2-trichloro-acetamide
  参考文献：
  名称：

  One-Pot Transformation of Trichloroacetamide into Readily Deprotectable Carbamates

  摘要：

  A trichloroacetamide group was converted to an isocyanate, which was in situ captured by a variety of alcohols in the presence of CuCl and n-BuN4Cl to afford the corresponding carbamates. The scope and limitation of this transformation are also described.

  DOI：

  10.1021/ol061123c

文献信息

• Microwave accelerated aza-Claisen rearrangements
  作者：Jozef Gonda、Miroslava Martinková、Andrea Zadrošová、Monika Šoteková、Jana Raschmanová、Patrik Čonka、Eva Gajdošíková、C. Oliver Kappe

  DOI：10.1016/j.tetlet.2007.07.157

  日期：2007.9

  The microwave-assisted thermal aza-Claisen rearrangement of allylic imidates and thiocyanates to the corresponding amides and isothiocyanates is investigated. Significant accelerations of the rearrangement of allylic imidates to amides and of allylic thiocyanates to isothiocyanates in comparison with standard thermal reactions is observed.

  研究了烯丙基酰亚胺和硫氰酸酯在微波辅助下的热氮杂-克莱森重排成相应的酰胺和异硫氰酸酯的过程。与标准的热反应相比，观察到烯丙基酰亚胺化成酰胺和烯丙基硫氰酸酯化成异硫氰酸酯的明显加速。
• One-Pot Transformation of Trichloroacetamide into Readily Deprotectable Carbamates
  作者：Toshio Nishikawa、Daisuke Urabe、Miho Tomita、Takashi Tsujimoto、Tomoko Iwabuchi、Minoru Isobe

  DOI：10.1021/ol061123c

  日期：2006.7.1

  A trichloroacetamide group was converted to an isocyanate, which was in situ captured by a variety of alcohols in the presence of CuCl and n-BuN4Cl to afford the corresponding carbamates. The scope and limitation of this transformation are also described.