(R)-2-heptyl 2,4-dinitrobenzenesulfenate

• 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: (R)-2-heptyl 2,4-dinitrobenzenesulfenate
• 英文别名: 1-[(2R)-heptan-2-yl]oxysulfanyl-2,4-dinitrobenzene
• 化学式: C₁₃H₁₈N₂O₅S
• 分子量: 314.362
• InChiKey: UVNZDQCVIMZGGK-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-(-)-2-庚醇 、 2,4-二硝基苯硫氯 在 吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以61.5%的产率得到(R)-2-heptyl 2,4-dinitrobenzenesulfenate
  参考文献：
  名称：

  A correlation between the absolute configurations of acyclic aliphatic and benzylic secondary alcohols and the optical rotations of their 2,4-dinitrobenzenesulfenyl derivatives

  摘要：

  The 2,4-dinitrobenzenesulfenate esters 2a-v of 11 acyclic aliphatic and 11 benzylic chiral secondary alcohols of known configuration were synthesized, and their sodium D line optical rotations and CD spectra were determined. The sign of the sodium D line rotations of the derivatives was consistently correlated with the absolute configuration of the carbinol carbon in the original alcohols. The CD spectra exhibited optically active transitions in the 320-400-nm region that corresponded in sign to the sodium D line optical rotations and were strong enough to dominate the sign of rotation at the sodium D line. Thus the optical rotations and CD spectra of these sulfenate ester derivatives are diagnostic for the absolute configurations of chiral secondary acyclic aliphatic and benzylic alcohols.

  DOI：

  10.1021/jo00057a044