2-amino-2-methylpropanesulfonic acid | 86311-35-5

• 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: 2-amino-2-methylpropanesulfonic acid
• 英文别名: 2-Amino-2-methylpropane-1-sulfonic acid
• CAS: 86311-35-5
• 化学式: C₄H₁₁NO₃S
• 分子量: 153.202
• InChiKey: DRNNATGSBCVJBN-UHFFFAOYSA-N

物化性质

• 溶解度：
  少量溶于甲醇和水

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  9
• 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：
  88.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-2-methylpropanesulfonic acid 以100的产率得到Auriclosene
  参考文献：
  名称：

  Bioorg. Med. Chem. Lett. 2009, 19, 1110-1114

  摘要：

  DOI：
• 作为产物：
  描述：

  2-((叔丁基亚磺酰基)氨基)-2-甲基丙烷-1-磺酸乙酯 在 lithium hydroxide 、 水 、 盐酸 、 甲醇 作用下， 以 四氢呋喃 、 甲醇 、 1,4-二氧六环 、 水 为溶剂， 反应 0.25h， 生成 2-amino-2-methylpropanesulfonic acid
  参考文献：
  名称：

  Stieglitz rearrangement of N,N-dichloro-β,β-disubstituted taurines under mild aqueous conditions

  摘要：

  New topical anti-infectives comprised of N,N-dichloro-beta,beta-disubstituted taurines [Tetrahedron Lett. 2008, 49, 2193; Biorg. Med. Chem. Lett. 2009, 19, 196] have been examined for structure-stability relationships (SSR) based upon various alkyl, heteroalkyl and cycloalkyl beta-substitutions. These substitutions affect order-of-magnitude changes in the aqueous stability of these N,N-dichloroamines which can undergo Stieglitz rearrangement of alkyl groups under extremely mild conditions (H(2)O, pH 4-7, 0-20 mM acetate or phosphate buffer, 20-40 degrees C). This process produces b-ketosulfonic acids which function as substrates for chlorination by the N-chlorotaurines which leads to their further degradation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.109

文献信息

• Efficient Synthesis of Taurine and Structurally Diverse Substituted Taurines from Aziridines
  作者：Libo Hu、Hui Zhu、Da-Ming Du、Jiaxi Xu

  DOI：10.1021/jo070470c

  日期：2007.6.1

  Taurine and substituted taurines were synthesized efficiently from aziridines via ring-opening reaction with thioacetic acid, oxidation with performic acid, and hydrolysis in hydrochloric acid. The current method shows more benefit in purification and efficiency in the preparation of taurine and structurally diverse 2-substituted, 2,2-disubstituted, and 1,2-, 2,2-, and 2,N-alkylene taurines.

  通过与硫代乙酸的开环反应，过甲酸的氧化和在盐酸中的水解，由氮丙啶有效地合成了牛磺酸和取代的牛磺酸。当前的方法在制备牛磺酸和结构上不同的2-取代的，2，2-二取代的和1，2-，2，2-和2，N-亚烷基牛磺酸中，在纯化和效率上显示出更多的益处。
• New methods for the preparation of 2-amino-2-methylpropanesulfonic acid
  作者：Daniela Braghiroli、Maria Di Bella

  DOI：10.1016/0040-4039(96)01597-3

  日期：1996.9

  2-Amino-2-methylpropanesulfonic acid 3 was prepared either from 2-N-[(1,1-dimethylethoxy)carbonyl]amino-2-methyl-1-propanol 4 or from 1-N-[(1,1-dimethyl-ethoxy)carbonyl]amino-2-methyl-2-propanol 5 in good overall yields.

  2-氨基-2-甲基丙烷磺酸3可由2-N-[（（1,1-二甲基乙氧基）羰基]氨基-2-甲基-1-丙醇4或1-N-[（1,1-二甲基） -乙氧基）羰基]氨基-2-甲基-2-丙醇5的总收率良好。
• A Versatile Synthesis of Various Substituted Taurines from Vicinal Amino Alcohols and Aziridines
  作者：Ning Chen、Weiyi Jia、Jiaxi Xu

  DOI：10.1002/ejoc.200900759

  日期：2009.11

  Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid oxidation of the thiazolidine-2-thione intermediates generated from vicinal amino alcohols or aziridines and carbon disulfide. Thestereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize

  牛磺酸和结构不同的取代牛磺酸已经通过由邻氨基醇或氮丙啶和二硫化碳产生的噻唑烷-2-硫酮中间体的过氧甲酸氧化合成。讨论了反应的立体化学和机理。该方法为无盐通用路线，纯化方便，可用于合成光学活性取代牛磺酸。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Versatile Synthesis of Free andN-Benzyloxycarbonyl-Protected 2,2-Disubstituted Taurines
  作者：Boyuan Wang、Wei Zhang、Leilei Zhang、Da-Ming Du、Gang Liu、Jiaxi Xu

  DOI：10.1002/ejoc.200700791

  日期：2008.1

  An effective and versatile method was developed to synthesize N-benzyloxycarbonyl-protected and free 2,2-disubstituted taurines. Several novel 2,2-disubstituted taurines, including aliphatic/aromatic and cyclic/acyclic derivatives, were obtained, which demonstrates the generality of this method. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  开发了一种有效且通用的方法来合成 N-苄氧羰基保护的游离 2,2-二取代牛磺酸。获得了几种新的 2,2-二取代牛磺酸，包括脂肪族/芳香族和环状/无环衍生物，这证明了该方法的通用性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Expeditious and Practical Synthesis of Various Substituted Taurines from Amino Alcohols
  作者：Jiaxi Xu、Wei Zhang、Boyuan Wang、Ning Chen、Da-Ming Du

  DOI：10.1055/s-2007-1000861

  日期：2008.1

  Various substituted taurines have been synthesized expeditiously and practically in satisfactory to good yields directly from amino alcohols using a two-step, one-pot procedure, in which the amino alcohols undergo sulfuric acid esterification and subsequent sodium sulfite substitution. Treatment of amino-substituted secondary alcohols using the same procedure gave 2-substituted or 1,2-di-substituted

  使用两步一锅法直接从氨基醇中快速且实际地以令人满意的高产率合成各种取代的牛磺酸，其中氨基醇经历硫酸酯化和随后的亚硫酸钠取代。使用相同程序处理氨基取代的仲醇得到 2-取代或 1,2-二-取代的牛磺酸，表明在取代步骤期间形成了作为中间体的氮丙啶。该方法是制备结构多样的 2-取代和 1,2-和 2,2-二取代牛磺酸的最有效途径之一。