Methanesulfonic acid 2-amino-2-methyl-propyl ester | 736910-12-6

• 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: Methanesulfonic acid 2-amino-2-methyl-propyl ester
• 英文别名: (2-Amino-2-methylpropyl) methanesulfonate
• CAS: 736910-12-6
• 化学式: C₅H₁₃NO₃S
• 分子量: 167.229
• InChiKey: XAJBFXKSDGSGIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 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：
  77.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 2-amino-2-methyl-propyl ester 在 水 、 sodium sulfite 作用下， 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
• 作为产物：
  描述：

  tert-butyl N-[1-(methanesulfonyloxy)-2-methylpropan-2-yl]carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以91.5%的产率得到Methanesulfonic acid 2-amino-2-methyl-propyl ester
  参考文献：
  名称：

  制备2-氨基-2-甲基丙烷磺酸的新方法

  摘要：

  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。

  DOI：

  10.1016/0040-4039(96)01597-3

文献信息

• 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。
• 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.