2,2-Dimethyl-propionic acid (3aR,5S,6S,6aR)-2,2-dimethyl-6-(2,2,2-trichloro-acetylamino)-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester | 906357-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-propionic acid (3aR,5S,6S,6aR)-2,2-dimethyl-6-(2,2,2-trichloro-acetylamino)-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
• 英文别名: [(3aR,5S,6S,6aR)-6-ethenyl-2,2-dimethyl-6-[(2,2,2-trichloroacetyl)amino]-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methyl 2,2-dimethylpropanoate
• CAS: 906357-08-2
• 化学式: C₁₇H₂₄Cl₃NO₆
• 分子量: 444.74
• InChiKey: SUDVJMVKXKTARX-IDYSPNNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (3aR,5S,6S,6aR)-2,2-dimethyl-6-(2,2,2-trichloro-acetylamino)-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 在 sodium carbonate 、 四丁基氯化铵 、 copper(l) chloride 、 苯甲醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到2,2-Dimethyl-propionic acid (3aR,5S,6S,6aR)-6-amino-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl 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 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 高碘酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 2,2-Dimethyl-propionic acid (3aR,5S,6S,6aR)-2,2-dimethyl-6-(2,2,2-trichloro-acetylamino)-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl 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

文献信息

• 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.