(1-aminocyclopentyl)methanesulfonic acid | 1016988-49-0

• 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: (1-aminocyclopentyl)methanesulfonic acid
• CAS: 1016988-49-0
• 化学式: C₆H₁₃NO₃S
• 分子量: 179.24
• InChiKey: XAEPEDSJPDMVDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  (1-aminocyclopentyl)methanesulfonic acid 在 sodium hypochlorite 、 磷酸 作用下， 以 水 为溶剂， 以34.1%的产率得到sodium 1-(dichloroamino)cyclopentylmethanesulfonate
  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
• 作为产物：
  描述：

  (1-氨基环戊基)甲基氢硫酸盐 在 sodium sulfite 作用下， 以 水 为溶剂， 生成 (1-aminocyclopentyl)methanesulfonic acid
  参考文献：
  名称：

  从氨基醇中快速实用合成各种取代牛磺酸

  摘要：

  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。

  DOI：

  10.1055/s-2007-1000861

文献信息

• Stieglitz rearrangement of N,N-dichloro-β,β-disubstituted taurines under mild aqueous conditions
  作者：Timothy P. Shiau、Ashley Houchin、Satheesh Nair、Ping Xu、Eddy Low、Ramin (Ron) Najafi、Rakesh Jain

  DOI：10.1016/j.bmcl.2008.12.109

  日期：2009.2

  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.
• 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。