(4R,αS)-4-(hexadecyloxymethyl)-3-(α-methylbenzyl)oxazolidin-2-one | 1353577-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,αS)-4-(hexadecyloxymethyl)-3-(α-methylbenzyl)oxazolidin-2-one
• 英文别名: (4R)-4-(hexadecoxymethyl)-3-[(1S)-1-phenylethyl]-1,3-oxazolidin-2-one
• CAS: 1353577-09-9
• 化学式: C₂₈H₄₇NO₃
• 分子量: 445.686
• InChiKey: IXCIHCLNTZXVNQ-AHKZPQOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,αS)-4-(hexadecyloxymethyl)-3-(α-methylbenzyl)oxazolidin-2-one 在 吡啶 、 甲烷磺酸 、 lithium hydroxide monohydrate 、 苯甲醚 作用下， 以 硝基甲烷 、 乙醇 为溶剂， 反应 8.0h， 生成 N-((R)-1-acetyl-3-(1-hexadecyloxy)propan-2-yl)formamide
  参考文献：
  名称：

  Total synthesis of (R)-(−)-actisonitrile via O-alkylation of optically active 4-hydroxymethyloxazolidin-2-one derivative

  摘要：

  The enantioselective synthesis of (R)-(-)-actisonitrile 1 has been achieved via O-alkylation of (4R,alpha S)-4-hydroxymethyl-3-(alpha-methylbenzyl)oxazolidin-2-one (alpha S)-4 with 1-iodohexadecane in the presence of CsOH in DMF. Under these reaction conditions, the O-alkylation was much faster than the intramolecular acyl transfer of (alpha S)-4. (C)2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.002
• 作为产物：
  描述：

  碘十六烷 、 (4R,αS)-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone 在 cesiumhydroxide monohydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以59%的产率得到(4R,αS)-4-(hexadecyloxymethyl)-3-(α-methylbenzyl)oxazolidin-2-one
  参考文献：
  名称：

  Total synthesis of (R)-(−)-actisonitrile via O-alkylation of optically active 4-hydroxymethyloxazolidin-2-one derivative

  摘要：

  The enantioselective synthesis of (R)-(-)-actisonitrile 1 has been achieved via O-alkylation of (4R,alpha S)-4-hydroxymethyl-3-(alpha-methylbenzyl)oxazolidin-2-one (alpha S)-4 with 1-iodohexadecane in the presence of CsOH in DMF. Under these reaction conditions, the O-alkylation was much faster than the intramolecular acyl transfer of (alpha S)-4. (C)2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.002

文献信息

• Total synthesis of (R)-(−)-actisonitrile via O-alkylation of optically active 4-hydroxymethyloxazolidin-2-one derivative
  作者：Shigeo Sugiyama、Akihiro Ishida、Moeko Tsuchida、Keitaro Ishii

  DOI：10.1016/j.tetasy.2011.11.002

  日期：2011.11

  The enantioselective synthesis of (R)-(-)-actisonitrile 1 has been achieved via O-alkylation of (4R,alpha S)-4-hydroxymethyl-3-(alpha-methylbenzyl)oxazolidin-2-one (alpha S)-4 with 1-iodohexadecane in the presence of CsOH in DMF. Under these reaction conditions, the O-alkylation was much faster than the intramolecular acyl transfer of (alpha S)-4. (C)2011 Elsevier Ltd. All rights reserved.