(1R,4S)-(S)-1-phenylethyl 1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylate | 1244954-25-3

• 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: (1R,4S)-(S)-1-phenylethyl 1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylate
• CAS: 1244954-25-3
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: IINHKDPQAIVSEM-SOVGHPHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S)-(-)-1-苯乙醇 、 (R)-tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid chloride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以87%的产率得到(1R,4S)-(S)-1-phenylethyl 1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylate
  参考文献：
  名称：

  Tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid: a chiral derivatizing agent for the determination of the absolute configuration of secondary alcohols

  摘要：

  A new chiral derivatizing agent, tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid (THENA), with a represented syn-periplanar disposition of O-C(alpha)-C=O as a part of the bicyclic system to lock the aromatic residue conformation and the availability of an internal reference proton for (1)H NMR spectral alignment, is introduced. In the determination of the absolute configuration of chiral secondary alcohols, THENA offered good uniformity of Delta delta with high reliability, resulting in unambiguous assignment of the absolute configuration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.062