Propan-1,2-diol-acetat-tosylat | 26923-94-4

• 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: Propan-1,2-diol-acetat-tosylat
• 英文别名: 2-(4-Methylphenyl)sulfonyloxypropyl acetate
• CAS: 26923-94-4
• 化学式: C₁₂H₁₆O₅S
• 分子量: 272.322
• InChiKey: IUGGOMCYHSJROM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2-丙二醇 、 乙酸酐 、 对甲苯磺酰氯 在 二正丁基氧化锡 、 三乙胺 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Propan-1,2-diol-acetat-tosylat 、 2-乙酰氧基丙基甲苯磺酸酯
  参考文献：
  名称：

  Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine

  摘要：

  The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.005

文献信息

• 1,3-Dioxolan-2-ylium cations from acylfurans: Conversion of furyl ketones to esters under nonoxidative conditions
  作者：John A. Bender、Samantha Daves、F.G. West

  DOI：10.1016/s0040-4039(98)00185-3

  日期：1998.4

  Acylfurans 3 furnished tosylated glycol monoesters 5 when treated with 1,2-diols in the presence of an equivalent of TsOH. This process likely occurs via protiodefuranation of the intermediate furyl ketals to form 1,3-dioxolan-2-ylium cations 8. Subsequent ring-opening via SN2 nucleophilic displacement by p-toluenesulfonate then provides esters 5. When a 1,3-diol was employed, furan-containing ester

  当在等价的TsOH存在下用1,2-二醇处理时，酰基呋喃3提供了甲苯磺酸化的二醇单酯5。此过程可能通过中间呋喃基缩酮的Protoodefuranation形成1，3-dioxolan-2-ylium阳离子8发生。随后通过对甲苯磺酸的S N 2亲核取代而开环，然后提供酯5。当使用1，3-二醇时，通过表观的醇醛二聚/片段化途径形成了含呋喃的酯9而不是标准产物。