2-(N-吗啉）乙烷磺酸 | 1912-28-3

• 物质功能分类: 分析化学 - 标准品 - 挥发性有机化合物(VOCs)
• 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-(N-吗啉）乙烷磺酸
• 中文别名: 2-(N-吗啉)乙烷磺酸
• 英文名称: methyl ethanesulfonate
• 英文别名: ethanesulfonic acid methyl ester；Aethansulfonsaeure-methylester；methyl ethyl sulfonate；Aethansulfonsaeuremethylester；Ethansulfonsaeure-methylester；Methyl ethansulfonat；Ethanesulfonic acid, methyl ester
• CAS: 1912-28-3
• 化学式: C₃H₈O₃S
• 分子量: 124.161
• InChiKey: YLJRCXSSKLWCDE-UHFFFAOYSA-N

物化性质

• 沸点：
  214℃
• 密度：
  1.177
• 闪点：
  84℃
• 溶解度：
  可溶于氯仿（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  7
• 可旋转键数：
  2
• 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

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  1,3
• 海关编码：
  2905199090

制备方法与用途

甲酯乙磺酸甲酯可作为有机合成中间体和医药中间体，主要应用于实验室研发和化工生产过程中。

反应信息

• 作为反应物：
  描述：

  2-(N-吗啉）乙烷磺酸 、 phenylmagnesium bromide 在 乙醚 作用下， 生成 乙基苯基砜
  参考文献：
  名称：

  Gilman; Robinson, Bulletin de la Societe Chimique de France, 1929, vol. <4> 45, p. 640

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基磺酸 、 原甲酸三甲酯 反应 14.0h， 以83%的产率得到2-(N-吗啉）乙烷磺酸
  参考文献：
  名称：

  Padmapriya, A. A.; Just, G.; Lewis, N. G., Synthetic Communications, 1985, vol. 15, # 12, p. 1057 - 1062

  摘要：

  DOI：

文献信息

• Solvent and Steric Effects on the Solvolysis of Polyvinylsulfonic Acid Esters
  作者：Sadao Yoshikawa、Oh-Kil Kim、Takeshi Hori

  DOI：10.1246/bcsj.39.1937

  日期：1966.9

  which contributed to the initial rate enhancement, while the latter indicates the aggregation of the polymer molecules owing to their strong hydrophobic character. The solvolysis rates, kp, for polymeric sulfonic esters were much greater than those, km, for monomeric analogs in all cases except isopropyl and n-butyl esters in 20% aqueous acetone. The relative rate (kp/km) increased with an increase

  乙磺酸酯的溶剂分解遵循密切的一级动力学，而聚乙烯磺酸酯的情况根据溶剂组成给出强烈弯曲的一级曲线。丙酮含量高时，聚磺酸酯的溶剂分解速率随着时间的推移逐渐降低，而含水量高时，溶剂分解在反应开始时受到抑制，但随着反应时间的延长而显着加速。前一个发现表明空间拥挤的释放有助于初始速率提高，而后者表明聚合物分子由于其强疏水性而聚集。聚合磺酸酯的溶剂分解速率 kp 远大于那些，km，对于所有情况下的单体类似物，除了异丙酯和正丁酯在 20% 丙酮水溶液中。相对速率（kp/km）随着丙酮含量的增加而增加，并且随着甲基酯的增加而明显增加。
• Studies on chemical carcinogens and mutagens. XXV. Chemoselectivity of alkyl sulfonates toward 4-(p-nitrobenzyl)pyridine (NBP) in phosphate buffer.
  作者：SHINICHI NINOMIYA、KOHFUKU KOHDA、YUTAKA KAWAZOE

  DOI：10.1248/cpb.32.1326

  日期：——

  Methyl, ethyl, and isopropyl esters of six alkanesulfonic acids and five p-substituted benzenesulfonic acids were synthesized and their alkylating abilities were evaluated in terms of the chemoselectivity toward 4-(p-nitrobenzyl) pyridine (NBP) in phosphate buffer (pH 6.0) containing 60% acetone. The chemoselectivity constant toward NBP, SNBP, was defined as the logarithm of the ratio of the molar fraction of an alkylating sulfonate which is consumed for alkylation of NBP versus the molar fraction of the residual alkylating agent which is hydrolyzed in the buffer medium. It was found that SNBP was not only markedly dependent on the structure of the alkyl moiety of the molecule, but also appreciably dependent on the electronic nature of the leaving sulfonic acid moiety. The structure-chemoselectivity relationship is discussed.

  合成了六种烷基磺酸和五种对取代苯磺酸的甲基、乙基和异丙基酯，并评估了它们在含有60%丙酮的磷酸盐缓冲液（pH 6.0）中对4-(对硝基苄基)吡啶（NBP）的烷基化能力。对NBP的化学选择性常数SNBP被定义为用于NBP烷基化的烷基磺酸的摩尔分数与在缓冲介质中水解的剩余烷基化试剂的摩尔分数之比的对数。研究发现，SNBP不仅显著依赖于分子中烷基部分的结构，还明显依赖于离去的磺酸部分的电子性质。讨论了结构与化学选择性之间的关系。
• 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。
• Shipov, A. G.; Baukov, Yu. I., Journal of general chemistry of the USSR, 1984, vol. 54, # 8, p. 1642 - 1657
  作者：Shipov, A. G.、Baukov, Yu. I.

  DOI：——

  日期：——
• 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.

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