(2R,αR)-3-benzyloxy-2-(α-methylbenzyl)aminopropanol | 592531-14-1

• 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: (2R,αR)-3-benzyloxy-2-(α-methylbenzyl)aminopropanol
• 英文别名: (2R)-2-[[(1R)-1-phenylethyl]amino]-3-phenylmethoxypropan-1-ol
• CAS: 592531-14-1
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: GDEMRACRVFBIFQ-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,αR)-3-benzyloxy-2-(α-methylbenzyl)aminopropanol 在 吡啶 、 二甲基硫 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 2-chloroethyl (2S,αR)-3-hydroxy-2-(α-methylbenzyl)aminopropyl carbonate
  参考文献：
  名称：

  A novel dynamic kinetic resolution accompanied by intramolecular transesterification: asymmetric synthesis of a 4-hydroxymethyl-2-oxazolidinone from serinol derivatives

  摘要：

  Reaction paths of the one-pot reaction of (R)-2-(alpha-methylbenzyl)amino-1,3-propanediol (1) and 2-chloroethyl chloroformate with DBU giving (4S,alphaR)-4-hydroxymethyl-3-(alpha-methylbenzyl)-2-oxazolidinone [(4S)-2] (94% de) were investigated. Intermediates of this reaction, 2-chloroethyl (2S)- and 2-chloroethyl (2R)-3-hydroxy-2-[(alphaR)-alpha-methylbenzyl]aminopropyl carbonates [(2S)-4 and (2R)-4], were synthesized individually. After the addition of DBU to the respective solution of the carbonate (2S)-4 and that of (2R)-4 in dichloromethane, the intramolecular transesteritication between (2S)-4 and (2R)-4 and the diastereoselective intramolecular cyclization proceeded to afford (4S)-2 in high diastereomeric excess. Therefore, two monocarbonates (2S)-4 and (2R)-4 were kinetically resolved by this cyclization during the intramolecular transesterification between (2S)-4 and (2R)-4. We found that this process involved dynamic kinetic resolution accompanied by intramolecular transesterification. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00477-0
• 作为产物：
  描述：

  (2R,αR)-1-[(α-methylbenzyl)aziridin-2-yl]methyl benzyl ether 在 氢氧化钾 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.5h， 生成 (2R,αR)-3-benzyloxy-2-(α-methylbenzyl)aminopropanol
  参考文献：
  名称：

  A novel dynamic kinetic resolution accompanied by intramolecular transesterification: asymmetric synthesis of a 4-hydroxymethyl-2-oxazolidinone from serinol derivatives

  摘要：

  Reaction paths of the one-pot reaction of (R)-2-(alpha-methylbenzyl)amino-1,3-propanediol (1) and 2-chloroethyl chloroformate with DBU giving (4S,alphaR)-4-hydroxymethyl-3-(alpha-methylbenzyl)-2-oxazolidinone [(4S)-2] (94% de) were investigated. Intermediates of this reaction, 2-chloroethyl (2S)- and 2-chloroethyl (2R)-3-hydroxy-2-[(alphaR)-alpha-methylbenzyl]aminopropyl carbonates [(2S)-4 and (2R)-4], were synthesized individually. After the addition of DBU to the respective solution of the carbonate (2S)-4 and that of (2R)-4 in dichloromethane, the intramolecular transesteritication between (2S)-4 and (2R)-4 and the diastereoselective intramolecular cyclization proceeded to afford (4S)-2 in high diastereomeric excess. Therefore, two monocarbonates (2S)-4 and (2R)-4 were kinetically resolved by this cyclization during the intramolecular transesterification between (2S)-4 and (2R)-4. We found that this process involved dynamic kinetic resolution accompanied by intramolecular transesterification. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00477-0