6-[Methyl(propan-2-yloxy)sulfonio]hexanoate;hydrochloride

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-[Methyl(propan-2-yloxy)sulfonio]hexanoate;hydrochloride
• 化学式: C₁₀H₂₁O₃S*Cl
• 分子量: 256.794
• InChiKey: NINJLOWLYOGPFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.78
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  47.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异丙醇 、 5-Carboxypentyl-chloro-methylsulfanium;chloride 生成 6-[Methyl(propan-2-yloxy)sulfonio]hexanoate;hydrochloride
  参考文献：
  名称：

  Modification of the Swern Oxidation:  Use of Stoichiometric Amounts of an Easily Separable, Recyclable, and Odorless Sulfoxide That Can Be Polymer-Bound

  摘要：

  Readily available 6-(methylsulfinyl)hexanoic acid (1) is employed as a substitute for DMSO in Swern oxidation reactions using oxalyl chloride to smoothly convert primary or secondary alcohols to corresponding aldehydes or ketones in high yield. The resulting 6-(methylthio)hexanoic acid (2) is easily separable by aqueous extraction or by filtration through silica gel and can be reoxidized to 1 with sodium metaperiodate in 97% yield, Low temperature (-60 degrees C) C-13 NMR spectrometry is used to examine the intermediates of this Swern process, The results indicate that any residual unoxidized alcohol is generated during Pummerer elimination of the alkoxysulfonium intermediate and can be minimized by extended exposure to triethylamine at -40 degrees C. Reaction of the potassium salt of 1 with cross-linked chloromethyl polystyrene affords a polymer-bound reagent 12 that quantitatively oxidizes borneol to camphor when used in two-fold excess.

  DOI：

  10.1021/jo961438d

文献信息

• Modification of the Swern Oxidation:  Use of Stoichiometric Amounts of an Easily Separable, Recyclable, and Odorless Sulfoxide That Can Be Polymer-Bound
  作者：Yaoquan Liu、John C. Vederas

  DOI：10.1021/jo961438d

  日期：1996.1.1

  Readily available 6-(methylsulfinyl)hexanoic acid (1) is employed as a substitute for DMSO in Swern oxidation reactions using oxalyl chloride to smoothly convert primary or secondary alcohols to corresponding aldehydes or ketones in high yield. The resulting 6-(methylthio)hexanoic acid (2) is easily separable by aqueous extraction or by filtration through silica gel and can be reoxidized to 1 with sodium metaperiodate in 97% yield, Low temperature (-60 degrees C) C-13 NMR spectrometry is used to examine the intermediates of this Swern process, The results indicate that any residual unoxidized alcohol is generated during Pummerer elimination of the alkoxysulfonium intermediate and can be minimized by extended exposure to triethylamine at -40 degrees C. Reaction of the potassium salt of 1 with cross-linked chloromethyl polystyrene affords a polymer-bound reagent 12 that quantitatively oxidizes borneol to camphor when used in two-fold excess.