4-((R)-Butane-1-sulfinyl)-but-1-ene | 188954-51-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: 4-((R)-Butane-1-sulfinyl)-but-1-ene
• 英文别名: 4-[(R)-Butane-1-sulfinyl]but-1-ene；1-[(R)-but-3-enylsulfinyl]butane
• CAS: 188954-51-0
• 化学式: C₈H₁₆OS
• 分子量: 160.28
• InChiKey: AZTGNJMIQFLBGY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-Butenylmagnesium bromide 、 Butane-1-sulfinic acid (3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 以 甲苯 为溶剂， 生成 4-((R)-Butane-1-sulfinyl)-but-1-ene
  参考文献：
  名称：

  NMR Stereochemical analysis of chiral alkylsulfoxides with α-methoxyaryl acetic acids

  摘要：

  (S)-alpha-methoxyphenyl and (S)-alpha-methoxy-2-naphthyl acetic acids (MPA and 2-NMA) were used as NMR chiral shift reagents for the stereochemical analysis of alkylsulfoxides. It was shown that the use of C6D6 as NMR solvent increased the magnitude of the observed effects for both H-1- and C-13-NMR spectra. Moreover, 2-NMA led to a much longer range effect on the chain but lowered the signal splitting of the alpha-methylene groups. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00536-8

文献信息

• Chiral homoallylic and allylic sulfoxides as models for the stereochemical analysis of sulfoxide thiaoleates
  作者：Franck Daligault、Amélie Arboré、Caroline Nugier-Chauvin、Henri Patin

  DOI：10.1016/j.tetasy.2004.01.018

  日期：2004.3

  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.