(4R,1'S)-4-[1'-(dibenzylamino)ethyl]-2,2-diethyl-1,3-dioxolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,1'S)-4-[1'-(dibenzylamino)ethyl]-2,2-diethyl-1,3-dioxolane
• 英文别名: (1S)-N,N-dibenzyl-1-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]ethanamine
• 化学式: C₂₃H₃₁NO₂
• 分子量: 353.505
• InChiKey: GBMODKUIAABLSY-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R)-[(1S)-1-(dibenzylamino)ethyl]oxirane 、 3-戊酮 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(4R,1'S)-4-[1'-(dibenzylamino)ethyl]-2,2-diethyl-1,3-dioxolane
  参考文献：
  名称：

  Totally Selective Ring-Opening of Amino Epoxides with Ketones:  A General Entry to Enantiopure (2R,3S)- and (2S,3S)-3-Aminoalkano-1,2-diols

  摘要：

  Transformation of enantiopure diastereoisomers (2R,1'S)- and (2S,1'S)-2-(1-aminoalkyl)epoxides into the corresponding 4-(1-aminoalkyl)-1,3-dioxolanes is achieved by reaction with different ketones in the presence of (BF3Et2O)-Et-.. The conversion takes place in very high yields. total selectivity, and without epimerization. A mechanism to explain this transformation is proposed. The obtained 1.3-dioxolanes can be deprotected. and (2R,3S)- and (2S,3S)-3-aminoalkano-1,2-diols were isolated.

  DOI：

  10.1021/ol047785o

文献信息

• Totally Selective Ring-Opening of Amino Epoxides with Ketones:  A General Entry to Enantiopure (2<i>R</i>,3<i>S</i>)- and (2<i>S</i>,3<i>S</i>)-3-Aminoalkano-1,2-diols
  作者：José M. Concellón、José Ramón Suárez、Santiago García-Granda、M. Rosario Díaz

  DOI：10.1021/ol047785o

  日期：2005.1.1

  Transformation of enantiopure diastereoisomers (2R,1'S)- and (2S,1'S)-2-(1-aminoalkyl)epoxides into the corresponding 4-(1-aminoalkyl)-1,3-dioxolanes is achieved by reaction with different ketones in the presence of (BF3Et2O)-Et-.. The conversion takes place in very high yields. total selectivity, and without epimerization. A mechanism to explain this transformation is proposed. The obtained 1.3-dioxolanes can be deprotected. and (2R,3S)- and (2S,3S)-3-aminoalkano-1,2-diols were isolated.