2,2,2-trichloro-N-[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enyl]acetamide | 1071467-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-trichloro-N-[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enyl]acetamide
• CAS: 1071467-97-4
• 化学式: C₁₀H₁₄Cl₃NO₃
• 分子量: 302.585
• InChiKey: LDKNCMVFKYLURS-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2,2,2-trichloro-N-[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enyl]acetamide 在 ruthenium trichloride sodium periodate 、 盐酸 作用下， 以 四氯化碳 、 乙腈 为溶剂， 以47%的产率得到羟基苏氨酸
  参考文献：
  名称：

  Studies on the aza-Claisen rearrangement of 4,5-dihydroxylated allylic trichloroacetimidates: the stereoselective synthesis of (2R,3S)- and (2S,3S)-2-amino-3,4-dihydroxybutyric acids

  摘要：

  Two new synthetic approaches, involving substrate directed aza-Claisen rearrangements and aza-Claisen rearrangements mediated by chiral Pd(II) catalysts, have been developed for the stereoselective synthesis of (2R,3S)-2-amino-3,4-dihydroxybutyric acid, a dihydroxylated alpha-amino acid from the edible mushroom, Lyophyllum ulmarium and its (2S,3S)-unnatural diastereomer. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.062
• 作为产物：
  描述：

  4,5-O-isopropylidenedioxy-2(E)-propenyl 2,2,2-trichloroacetimidate 在 双(乙腈)氯化钯(II) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2E,4S)-1-(trichloromethylcarbonylamino)-4,5-dihydroxypent-1-ene 、 2,2,2-trichloro-N-((S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl)acetamide 、 2,2,2-trichloro-N-[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enyl]acetamide
  参考文献：
  名称：

  Studies on the aza-Claisen rearrangement of 4,5-dihydroxylated allylic trichloroacetimidates: the stereoselective synthesis of (2R,3S)- and (2S,3S)-2-amino-3,4-dihydroxybutyric acids

  摘要：

  Two new synthetic approaches, involving substrate directed aza-Claisen rearrangements and aza-Claisen rearrangements mediated by chiral Pd(II) catalysts, have been developed for the stereoselective synthesis of (2R,3S)-2-amino-3,4-dihydroxybutyric acid, a dihydroxylated alpha-amino acid from the edible mushroom, Lyophyllum ulmarium and its (2S,3S)-unnatural diastereomer. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.062