methyl isethionate | 81171-21-3

• 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
• 英文名称: methyl isethionate
• 英文别名: isethionic acid methyl ester；Ethanesulfonic acid, 2-hydroxy-, methyl ester；methyl 2-hydroxyethanesulfonate
• CAS: 81171-21-3
• 化学式: C₃H₈O₄S
• 分子量: 140.16
• InChiKey: ARDOMBFXFIFOFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  8
• 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：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hexadecyl 2-(dimethylamino)ethanesulfonate 、 methyl isethionate 生成 2-<(hexadecyloxy)sulfonyl>-N,N,N-trimethylethanaminium 2-hydroxyethanesulfonate
  参考文献：
  名称：

  Alkylation of sulfonate anions via substrate-reagent ion-pair (srip) reactions of [2]betylates. Preparation of alkyl esters of hydroxyalkanesulfonic acids

  摘要：

  DOI：

  10.1016/s0040-4039(01)81961-4

文献信息

• 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。
• KING, J. F.;ASLAM, M., TETRAHEDRON LETT., 1981, 22, N 37, 3573-3576
  作者：KING, J. F.、ASLAM, M.

  DOI：——

  日期：——
• Alkylation of sulfonate anions via substrate-reagent ion-pair (srip) reactions of [2]betylates. Preparation of alkyl esters of hydroxyalkanesulfonic acids
  作者：J.F. King、M. Aslam

  DOI：10.1016/s0040-4039(01)81961-4

  日期：1981.1