丙烷-1-磺酸乙酯 | 91284-43-4

• 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: 丙烷-1-磺酸乙酯
• 英文名称: ethyl 1-propanesulfonate
• 英文别名: ethyl propanesulfonate；1-Propanesulfonic acid, ethyl ester；ethyl propane-1-sulfonate
• CAS: 91284-43-4
• 化学式: C₅H₁₂O₃S
• 分子量: 152.214
• InChiKey: DABYSJMCEKEQKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  4
• 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：

  N-甲基咪唑 、 丙烷-1-磺酸乙酯 以 乙酸乙酯 为溶剂， 反应 48.0h， 以42%的产率得到3-ethyl-1-methyl-1H-imidazol-3-ium propane-1-sulfonate
  参考文献：
  名称：

  1-Alkyl-3-methylimidazolium alkanesulfonate ionic liquids, [CnH2n+1mim][CkH2k+1SO3]: synthesis and physicochemical properties

  摘要：

  合成了一系列1-烷基-3-甲基咪唑硫酸烷基酯离子液体[Cnmim][CkSO3]，其中阳离子和阴子的烷基链长度均可变（n = 1-6，8 或 10；k = 1-4 或 6），其中有16种为新型离子液体。通过1H和13C核磁共振波谱学以及质谱分析表征了这些离子液体。测定了它们的粘度和密度随温度变化的函数关系、熔点和分解温度。无论是实验测得的分子体积还是计算得出的，都发现与烷基链长度之和（n + k）呈线性相关。

  DOI：

  10.1039/b910177m
• 作为产物：
  描述：

  乙醇 、 丙基磺酰氯 在 2,6-二甲基吡啶 、 硫酸 作用下， 反应 2.5h， 以55%的产率得到丙烷-1-磺酸乙酯
  参考文献：
  名称：

  Studies on chemical carcinogens and mutagens. XXV. Chemoselectivity of alkyl sulfonates toward 4-(p-nitrobenzyl)pyridine (NBP) in phosphate buffer.

  摘要：

  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。

  DOI：

  10.1248/cpb.32.1326

文献信息

• Cytotoxicity of fluorine-containing alkyl alkanesulfonates to cultured leukemia L1210 cells.
  作者：YUKO OHTA、KOHFUKU KOHDA、HIROSHI KIMOTO、TAKASHI OKANO、YUTAKA KAWAZOE

  DOI：10.1248/cpb.36.2410

  日期：——

  Ethyl esters of alkanesulfonic acids, isethionic acid, trifluoromethanesulfonic acid, and 2, 2, 2-trifluoroethanesulfonic acid were synthesized and tested for inhibitory activity toward the growth of cultured leukemia L1210 cells. A quantitative correlation with the rate of hydrolysis and the capacity factor (partition property) was demonstrated by a multiple linear regression analysis; the more reactive and more lipophilic, the more cytotoxic they are. Interestingly, fluorine substitution on the alcoholic moiety resulted in remarkable deviations of the toxicity from those expected from the correlation found for the ethyl esters without fluorine substitution. Then, some fluorine derivatives of busulfan, a clinically used bifunctional sulfonate, were synthesized and tested. 2, 2-Difluoroethyl 2, 2, 2-trifluoroethanesulfonate was several times more cytotoxic than busulfan.

  烷基磺酸乙酯、异硫羟酸、三氟甲磺酸和2,2,2-三氟乙磺酸的乙酯被合成并用于测试对培养的白血病L1210细胞生长的抑制活性。通过多元线性回归分析，证明了它们与水解速率和容量因子（分配性质）之间的量化相关性；越活泼、越亲脂性，它们的细胞毒性就越大。有趣的是，醇部分上的氟取代导致毒性显著偏离了预期，这种预期是基于不含氟取代的乙酯的相关性得出的。然后，合成了一些临床使用的双功能磺酸盐-白消安的氟化衍生物并进行了测试。2,2-二氟乙基2,2,2-三氟乙磺酸盐的细胞毒性比白消安高出数倍。
• 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。
• KAWAZOE YUTAKA; NINOMIYA SHIN-ICHI; KOHDA KOHFUKU; KIMOTO HIROSHI, TETRAHEDRON LETT., 27,(1986) N 25, 2897-2900
  作者：KAWAZOE YUTAKA、 NINOMIYA SHIN-ICHI、 KOHDA KOHFUKU、 KIMOTO HIROSHI

  DOI：——

  日期：——
• 1-Alkyl-3-methylimidazolium alkanesulfonate ionic liquids, [CnH2n+1mim][CkH2k+1SO3]: synthesis and physicochemical properties
  作者：Marijana Blesic、Małgorzata Swadźba-Kwaśny、Tayeb Belhocine、H. Q. Nimal Gunaratne、José N. Canongia Lopes、Margarida F. Costa Gomes、Agílio A. H. Pádua、Kenneth R. Seddon、Luís Paulo N. Rebelo

  DOI：10.1039/b910177m

  日期：——

  A set of 1-alkyl-3-methylimidazolium alkanesulfonate ionic liquids, [Cnmim][CkSO3], formed by the variation of the alkyl chain lengths both in the cation and the anion (n = 1–6, 8, or 10; k = 1–4, or 6), was synthesised, with sixteen of them being novel. The ionic liquids were characterised by 1H and 13C NMR spectroscopy, and mass spectrometry. Their viscosities and densities as a function of temperature, as well as melting points and decomposition temperatures, were determined. The molecular volumes, both experimental and calculated, were found to depend linearly on the sum (n + k).

  合成了一系列1-烷基-3-甲基咪唑硫酸烷基酯离子液体[Cnmim][CkSO3]，其中阳离子和阴子的烷基链长度均可变（n = 1-6，8 或 10；k = 1-4 或 6），其中有16种为新型离子液体。通过1H和13C核磁共振波谱学以及质谱分析表征了这些离子液体。测定了它们的粘度和密度随温度变化的函数关系、熔点和分解温度。无论是实验测得的分子体积还是计算得出的，都发现与烷基链长度之和（n + k）呈线性相关。