(R)-allyl butyl sulfoxide | 20580-81-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: (R)-allyl butyl sulfoxide
• 英文别名: (+)-(R)-Allyl-butyl-sulfoxid；3-((R)-butane-1-sulfinyl)-propene
• CAS: 20580-81-8
• 化学式: C₇H₁₄OS
• 分子量: 146.254
• InChiKey: WLWFLBIRSYUQOE-VIFPVBQESA-N

物化性质

• 沸点：
  258.6±19.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  9.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  烯丙基溴化镁 、 1,2:5,6-di-O-isopropylidene-D-glucofuranosyl-(R)-butyl-sulfinate 以 乙醚 、 甲苯 为溶剂， 以73%的产率得到(R)-allyl butyl sulfoxide
  参考文献：
  名称：

  Chiral homoallylic and allylic sulfoxides as models for the stereochemical analysis of sulfoxide thiaoleates

  摘要：

  Both enantiomers of n-butyl allyl sulfoxide have been synthesized and are reported as models of bio-oxidized thiafatty acid analogues. The stereochemical analysis of these aliphatic sulfoxides as well as their homoallylic counterparts, were performed by the use of chiral NMR shift reagents. We first checked the validity of the chiral solvating NMR reagents method using the alpha-methoxyphenylacetic acid (MPA) and the Pirkle-like alcohol 1-(9-anthryl)-2,2,2,-trifluoroethanol (TAE). We then compared the relative efficiency of these reagents in the enantiomeric discrimination of our sulfoxide models and determination of their enantiomeric excess. On the basis of experiments conducted on our real targets, optically enriched sulfoxides from the Chlorella incubations of 12- and 13-thiastearic acids, the versatality of these NMR reagents for the ee determination as well as the assignment of the absolute configuration at sulfur, are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.018