2-丁磺酸甲酯 | 2697-52-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 2-丁磺酸甲酯
• 英文名称: 2-butanesulfonic acid methyl ester
• 英文别名: Butansulfonsaeure-(2)-methylester；Butan-2-sulfonsaeure-methylester；Methyl butane-2-sulfonate
• CAS: 2697-52-1
• 化学式: C₅H₁₂O₃S
• 分子量: 152.214
• InChiKey: DXMQATXWZITLLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-丁磺酸甲酯 、 2-[2-(2-Methoxyethoxy)ethoxy]ethyl 3-[2-[4-(dimethylamino)-6-[2-[3-[2-[2-(2-methoxyethoxy)ethoxy]ethoxycarbonyl]phenyl]ethynyl]pyridin-2-yl]ethynyl]benzoate 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Sequence dependence of methylation rate enhancement in meta-phenyleneethynylene foldamers

  摘要：

  报告了一系列线性和支链甲基磺酸盐的具有末端连接的 4-二甲基氨基吡啶（DMAP）残基的偏苯乙炔（mPE）低聚物的甲基化率；这些数据表明，将 DMAP 单元置于序列的中点，可使折叠体腔起到反应筛的作用，从而增强选择性甲基化。

  DOI：

  10.1039/b716122k
• 作为产物：
  描述：

  2-丁基磺酸 、 原甲酸三甲酯 以3.10 g的产率得到2-丁磺酸甲酯
  参考文献：
  名称：

  Foldamers as Reactive Sieves:  Reactivity as a Probe of Conformational Flexibility

  摘要：

  A series of m-phenyleneethynylene (mPE) oligomers modified with a dimethylaminopyridine (DMAP) unit were treated with methyl sulfonates of varying sizes and shapes, and the relative reactivities were measured by UV spectrophotometry. Using a small-molecule DMAP analogue as a reference, each of the methyl sulfonates was shown to react at nearly identical rate. In great contrast, oligomers that are long enough to fold, and hence capable of binding the methyl sulfonate, experience rate enhancements of 18-1600-fold relative to that of the small-molecule analogue, depending on the type of alkyl chain attached to the guest. Three different oligomer lengths were studied, with the longest oligomers exhibiting the fastest rate and greatest substrate specificity. Even large, bulky guests show slightly enhanced methylation rates compared to that with the reference DMAP, which suggests a dynamic nature to the oligomer's binding cavity. Several mechanistic models to describe this behavior are discussed.

  DOI：

  10.1021/ja067670a

文献信息

• Asinger,F. et al., Chemische Berichte, 1965, vol. 98, p. 2154 - 2158
  作者：Asinger,F. et al.

  DOI：——

  日期：——
• Mass spectral study of alkyl alkanesulfonates
  作者：William E. Truce、Robert W. Campbell、Gary D. Madding

  DOI：10.1021/jo01288a013

  日期：1967.2
• Foldamers as Reactive Sieves:  Reactivity as a Probe of Conformational Flexibility
  作者：Ronald A. Smaldone、Jeffrey S. Moore

  DOI：10.1021/ja067670a

  日期：2007.5.1

  A series of m-phenyleneethynylene (mPE) oligomers modified with a dimethylaminopyridine (DMAP) unit were treated with methyl sulfonates of varying sizes and shapes, and the relative reactivities were measured by UV spectrophotometry. Using a small-molecule DMAP analogue as a reference, each of the methyl sulfonates was shown to react at nearly identical rate. In great contrast, oligomers that are long enough to fold, and hence capable of binding the methyl sulfonate, experience rate enhancements of 18-1600-fold relative to that of the small-molecule analogue, depending on the type of alkyl chain attached to the guest. Three different oligomer lengths were studied, with the longest oligomers exhibiting the fastest rate and greatest substrate specificity. Even large, bulky guests show slightly enhanced methylation rates compared to that with the reference DMAP, which suggests a dynamic nature to the oligomer's binding cavity. Several mechanistic models to describe this behavior are discussed.
• Sequence dependence of methylation rate enhancement in meta-phenyleneethynylene foldamers
  作者：Ronald A. Smaldone、Jeffrey S. Moore

  DOI：10.1039/b716122k

  日期：——

  The methylation rates of a meta-phenyleneethynylene (mPE) oligomer with a terminally-attached 4-dimethylaminopyridine (DMAP) residue are reported for a series of linear and branched methyl sulfonates; these data show that selective methylation is enhanced by locating the DMAP unit at the midpoint of the sequence, allowing the foldamer cavity to function as a reactive sieve.

  报告了一系列线性和支链甲基磺酸盐的具有末端连接的 4-二甲基氨基吡啶（DMAP）残基的偏苯乙炔（mPE）低聚物的甲基化率；这些数据表明，将 DMAP 单元置于序列的中点，可使折叠体腔起到反应筛的作用，从而增强选择性甲基化。