1-戊烷磺酸 | 35452-30-3

• 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
• 中文名称: 1-戊烷磺酸
• 英文名称: 1-pentanesulfonic acid
• 英文别名: pentane sulfonic acid；Pentan-1-sulfonsaeure；n-Pentylsulfonsaeure；n-pentane-1-sulfonic acid；pentane-1-sulfonic acid
• CAS: 35452-30-3
• 化学式: C₅H₁₂O₃S
• mdl: MFCD00066394
• 分子量: 152.214
• InChiKey: RJQRCOMHVBLQIH-UHFFFAOYSA-N

物化性质

• 熔点：
  15.9 °C

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：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2904100000

反应信息

• 作为反应物：
  描述：

  1-戊烷磺酸 在 diphosphorus pentasulfide 、 水 作用下， 生成 1-戊硫醇
  参考文献：
  名称：

  五硫化二磷还原磺酸

  摘要：

  通过用五硫化二磷处理，容易将芳烃和链烷磺酸还原为相应的多硫化物R-（S）n -R（n =2.9≈3.3）。在该反应中，POS和PSH键的形成均被认为是还原的关键步骤。

  DOI：

  10.1016/s0040-4039(00)85691-9
• 作为产物：
  描述：

  1-溴戊烷 在 sodium sulfite 作用下， 以 水 为溶剂， 反应 12.0h， 生成 1-戊烷磺酸
  参考文献：
  名称：

  碰撞诱导的有机磺酸阴离子的离解，形成亚硫酸氢根阴离子（HSO3-，m / z 81）

  摘要：

  在大多数有机磺酸盐的负离子碰撞诱导的离解质谱图中，三氧化硫自由基阴离子（SO 3 –·）的基峰在m / z 80处观察到。相反，一些磺酸盐（如半胱氨酸，氨基甲磺酸盐和2-苯基乙烷磺酸盐）的产物离子谱图显示了亚硫酸氢根阴离子（HSO 3 –）在m / z 81处的基峰。对大量磺酸盐的研究表明，相对于硫原子，β位上存在氢原子是亚硫酸氢根阴离子形成的先决条件。HSO 3的形成–当原子在β位是氮，或剩下的中性物质是高度共轭的分子，例如苯乙烯或丙烯酸。与aminomethanesulfonate氘交换的实验表明，对于HSO氢3 -形成从传送β位上。与2-磺基丙酸的m / z 81处的峰相反，在2-磺基乙酸的光谱中存在于m / z 80的峰，证实了所提出的氢转移机理。对于二酸化合物，例如4-磺基丁酸和半胱氨酸，m / z 81离子可以通过另一种机理形成，其中羧酸根部分的负电荷攻击α相对于硫原子的碳。用

  DOI：

  10.1002/jms.2975

文献信息

• Reduction of Sulfonic Acids and Related Organosulfur Compounds with Triphenylphosphine–Iodine System
  作者：Shigeru Oae、Hideo Togo

  DOI：10.1246/bcsj.56.3802

  日期：1983.12

  excess iodine, however, these aliphatic sulfur compounds are converted eventually to the corresponding alkyl iodides. The relative reactivities of these sulfonyl derivatives in the reaction with the triphenylphosphine–iodine system are the following. Aromatic series: ArSO2Cl, ArSO2SAr′>ArSO2H>ArSO3R>ArSO3−HNBu3+ (or PyH+)>ArSO3H>ArSO2SO2Ar>>ArSO2CH2C(CH3)3, ArSO3Ar′. Aliphatic series: RSO2Cl, RSO2SR′,

  通过用三苯基膦和催化量的碘的混合物处理，芳烃磺酸、它们的钠盐和烷基芳烃磺酸盐可以很容易地还原成相应的芳烃硫醇，而烷烃磺酸、亚磺酸、二硫化物、硫代磺酸测试剂和磺酸盐也很容易类似地还原为相应的硫醇。然而，在用三苯基膦和过量碘的混合物处理后，这些脂肪族硫化合物最终转化为相应的烷基碘。这些磺酰基衍生物在与三苯基膦-碘体系反应中的相对反应性如下。芳族系列​​：ArSO2Cl、ArSO2SAr′>ArSO2H>ArSO3R>ArSO3−HNBu3+（或PyH+）>ArSO3H>ArSO2SO2Ar>>ArSO2CH2C(CH3)3、ArSO3Ar′。脂肪族系列：RSO2Cl、RSO2SR'、RSO2-HNBu3+>RSO3-HNBu3+>RSSR，RSO2H>RSO3H>RSH>RSO3R'。在这些反应中，带有供电子取代基的芳烃磺酸比具有供电子取代基的芳烃磺酸更容易被还原。
• Reduction of Sulfonic Acids with Triphenylphosphine–Diaryl Disulfide System
  作者：Shigeru Oae、Hideo Togo

  DOI：10.1246/bcsj.57.232

  日期：1984.1

  Diaryl disulfides are effective catalysts to reduce arenesulfonic acids with triphenylphosphine to the corresponding arenethiols in good yields, while alkanesulfonic acids are transferred into the corresponding alkyl aryl sulfides. Arenesulfonic acids bearing electron-donating substituents can be reduced more readily than those having electron-withdrawing substituents, while diaryl disulfides bearing electron-withdrawing substituents are more effective catalysts than diaryl disulfides with electron-donating ring substituents.

  二芳基二硫化合物是有效的催化剂，能与三苯基膦共用，将芳基磺酸还原为相应产率良好的芳基硫醇，同时将烷基磺酸转化为相应的烷基芳基硫醚。电子供体取代的芳基磺酸比电子受体取代的芳基磺酸更容易被还原，而具有电子受体取代基的二芳基二硫化合物比具有电子供体环取代基的二芳基二硫化合物更有效作为催化剂。
• 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 of hypolipidemic agents. I. Syntheses and hypolipidemic activities of 1-substituted 2-alkanone derivatives.
  作者：KAZUO OGAWA、TADAFUMI TERADA、YOSHIYUKI MURANAKA、TOSHIHIRO HAMAKAWA、SADAO HASHIMOTO、SETSURO FUJII

  DOI：10.1248/cpb.34.1118

  日期：——

  Many 1-substituted 2-alkanone derivatives were synthesized and their inhibitory activities toward pancreatic lipase and esterase were examined in order to obtain hypolipidemic agents. 1-Benzenesulfonyloxy-2-pentanone (VI-2a) and 1-(2, 4, 6-trimethylbenzenesulfonyloxy)-2-pentanone (VI-2q) exhibited not only potent and selective esterase inhibitions (IC50 : 9.0×10-7M and 1.0×10-6M, respectively), but also potent hypolipidemic action (90 and 92% reductions of plasma triglyceride, and 53 and 90% reductions of plasma total cholesterol, respectively). A novel working hypothesis is presented to account for the lowering of the plasma lipids level, i.e., that inhibition of esterase and lipase activities in the small intestinal lumen may be responsible for the decrease in the plasma lipids level.

  合成了许多1-取代的2-酮烷基衍生物，并考察了它们对胰脂肪酶和酯酶的抑制活性，以期获得降脂药物。1-苯磺酰氧基-2-戊酮（VI-2a）和1-(2, 4, 6-三甲基苯磺酰氧基)-2-戊酮（VI-2q）不仅表现出显著且具有选择性的酯酶抑制（IC50：9.0×10^-7M 和 1.0×10^-6M），而且还具有强效的降脂作用（血浆甘油三脂分别减少90%和92%，血浆总胆固醇分别减少53%和90%）。提出了一个新的工作假设来解释血浆脂质水平的降低，即小肠腔内酯酶和脂肪酶活性的抑制可能是导致血浆脂质水平下降的原因。
• 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。