(4R,αR)-(3-α-methylbenzyl-2-oxazolidinon-4-yl)methyl 4-nitrobenzoate | 609826-53-1

• 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: (4R,αR)-(3-α-methylbenzyl-2-oxazolidinon-4-yl)methyl 4-nitrobenzoate
• CAS: 609826-53-1
• 化学式: C₁₉H₁₈N₂O₆
• 分子量: 370.362
• InChiKey: YTLZBBZCAOETHJ-CXAGYDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  98.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,αR)-(3-α-methylbenzyl-2-oxazolidinon-4-yl)methyl 4-nitrobenzoate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以92%的产率得到(4R)-4-hydroxymethyl-N-[(αR)-α-methylbenzyl]-2-oxazolidinone
  参考文献：
  名称：

  One-pot acylation and fractional crystallization: preparation of optically active serinol monobenzoates

  摘要：

  Mono-O-acylation of (R)-2-(alpha-methylbenzyl)amino-1,3-propanediol 1 with 4-nitrobenzoyl chloride and DMAP in dichloromethane at room temperature gave crystals of optically active (2S,alphaR)-3-hydroxy-2-(alpha-methylbenzyl)aminopropyl 4-nitrobenzoate hydrochloride [(2S)-2a(.)HCl] in 33% yield by fractional crystallization. Optically active oxazolidinones, aziridines, and serinol derivatives were synthesized from the benzoate (2S)-2a. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00410-5
• 作为产物：
  描述：

  (R)-2-[(α-methylbenzyl)amino]-1,3-propanediol 在 4-二甲氨基吡啶 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 38.0h， 生成 (4R,αR)-(3-α-methylbenzyl-2-oxazolidinon-4-yl)methyl 4-nitrobenzoate
  参考文献：
  名称：

  One-pot acylation and fractional crystallization: preparation of optically active serinol monobenzoates

  摘要：

  Mono-O-acylation of (R)-2-(alpha-methylbenzyl)amino-1,3-propanediol 1 with 4-nitrobenzoyl chloride and DMAP in dichloromethane at room temperature gave crystals of optically active (2S,alphaR)-3-hydroxy-2-(alpha-methylbenzyl)aminopropyl 4-nitrobenzoate hydrochloride [(2S)-2a(.)HCl] in 33% yield by fractional crystallization. Optically active oxazolidinones, aziridines, and serinol derivatives were synthesized from the benzoate (2S)-2a. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00410-5

文献信息

• One-pot acylation and fractional crystallization: preparation of optically active serinol monobenzoates
  作者：Shigeo Sugiyama、Takayuki Inoue、Keitaro Ishii

  DOI：10.1016/s0957-4166(03)00410-5

  日期：2003.8

  Mono-O-acylation of (R)-2-(alpha-methylbenzyl)amino-1,3-propanediol 1 with 4-nitrobenzoyl chloride and DMAP in dichloromethane at room temperature gave crystals of optically active (2S,alphaR)-3-hydroxy-2-(alpha-methylbenzyl)aminopropyl 4-nitrobenzoate hydrochloride [(2S)-2a(.)HCl] in 33% yield by fractional crystallization. Optically active oxazolidinones, aziridines, and serinol derivatives were synthesized from the benzoate (2S)-2a. (C) 2003 Elsevier Ltd. All rights reserved.