N-dichloroacetyl-2,2-dimethoxyethylamine | 39106-23-5

• 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-dichloroacetyl-2,2-dimethoxyethylamine
• 英文别名: 2,2-Dichloro-N-(2,2-dimethoxyethyl)acetamide；2,2-dichloro-N-(2,2-dimethoxyethyl)acetamide
• CAS: 39106-23-5
• 化学式: C₆H₁₁Cl₂NO₃
• 分子量: 216.064
• InChiKey: CQMJQSWUVQYYSC-UHFFFAOYSA-N

物化性质

• 沸点：
  314.9±42.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-(+)-苏-2-氨基-1-(4-硝基苯基)-1,3-丙二醇 、 N-dichloroacetyl-2,2-dimethoxyethylamine 在 硫酸 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 25.0h， 以58%的产率得到(2R,4S,5S)-5-amino-2-dichloroacetylaminomethyl-4-(4-nitrophenyl)-1,3-dioxane
  参考文献：
  名称：

  Synthesis of Some SelectivelyN-Protected (1S,2S)-p-Nitrophenylserinol–Based Diamino-1,3-dioxanes and Tripodands

  摘要：

  The unconventional methodology for the non-epimerizable cycloacetalization of optically active (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (p-nitrophenylserinol) (condensed H2SO4 96% as solvent and catalyst, i.e., sulfuric transacetalization) producing (2R,4S,5S) diamino-1,3-dioxanes was enlarged by the use of N-protected forms of 2,2-dimethoxyethylamine (DMEA, aminoacetaldehyde dimethylacetal). Conversely, N-protected derivatives of p-nitrophenylserinol were successfully cyclocondensed with DMEA in the same sulfuric conditions. N-Functionalization of DMEA upon treatment with trimesic acid trichloride and cyanuric chloride yielded the corresponding triple amide and melamine, respectively. Their adapted sulfuric transacetalization in triplicate in reaction with arylserinols (aryl: phenyl, p-nitrophenyl) afforded a new series of optically active tripodands.

  DOI：

  10.1080/00397911.2015.1078360
• 作为产物：
  描述：

  二氯乙酸甲酯 、 氨基乙醛缩二甲醇 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 N-dichloroacetyl-2,2-dimethoxyethylamine
  参考文献：
  名称：

  Synthesis of Some SelectivelyN-Protected (1S,2S)-p-Nitrophenylserinol–Based Diamino-1,3-dioxanes and Tripodands

  摘要：

  The unconventional methodology for the non-epimerizable cycloacetalization of optically active (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (p-nitrophenylserinol) (condensed H2SO4 96% as solvent and catalyst, i.e., sulfuric transacetalization) producing (2R,4S,5S) diamino-1,3-dioxanes was enlarged by the use of N-protected forms of 2,2-dimethoxyethylamine (DMEA, aminoacetaldehyde dimethylacetal). Conversely, N-protected derivatives of p-nitrophenylserinol were successfully cyclocondensed with DMEA in the same sulfuric conditions. N-Functionalization of DMEA upon treatment with trimesic acid trichloride and cyanuric chloride yielded the corresponding triple amide and melamine, respectively. Their adapted sulfuric transacetalization in triplicate in reaction with arylserinols (aryl: phenyl, p-nitrophenyl) afforded a new series of optically active tripodands.

  DOI：

  10.1080/00397911.2015.1078360