1-amino-2-phenylpropane-2-sulfonic acid | 1198184-72-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-amino-2-phenylpropane-2-sulfonic acid
• 英文别名: H2NCH2C(Me)PhSO3H；1-Methyl-1-phenyltaurine
• CAS: 1198184-72-3
• 化学式: C₉H₁₃NO₃S
• 分子量: 215.273
• InChiKey: AOAVXQHPJBWZQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  S-2-nitro-1-methyl-1-phenylethyl thiolacetate 在 甲酸 、 palladium 10% on activated carbon 、 氢气 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 1-amino-2-phenylpropane-2-sulfonic acid
  参考文献：
  名称：

  Facile synthesis of various substituted taurines, especially syn- and anti-1,2-disubstituted taurines, from nitroolefins

  摘要：

  Taurine and substituted taurines present a group of important structural elements in many natural products. Various substituted taurines, including 1- and 2-substituted, 1,1-, syn-1,2-, and anti-1,2-disubstituted taurines, were synthesized from the corresponding nitroolefins via Michael addition with thioacetic acid, oxidation with peroxyformic acid, and the catalytic hydrogenation under the catalysis of palladium on carbon or platinum dioxide. It is a general, versatile, and salt-free method for the preparation of substituted taurines, especially for syn- and anti-1,2-disubstituted taurines and some taurines with more bulky substituents. The stereostructures of both syn- and anti-1,2-disubstituted taurines were deduced from the nitroalkyl thioacetates in the Michael addition, which were identified via the Karplus equation analysis and computational analysis, and finally confirmed by the XRD single crystal analysis. The diastereoselectivity in the Michael addition was rationalized with the Cram rule. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.031

文献信息

• Versatile synthesis of α-substituted taurines from nitroolefins
  作者：Chuanxiang Xu、Jiaxi Xu

  DOI：10.1007/s00726-010-0655-7

  日期：2011.6

  1-substituted and 1,1-disubstituted taurines were synthesized from nitroolefins via the Michael addition with sodium ethylxanthate, oxidation with performic acid, and reduction with hydrogen in the presence of palladium on carbon powder. The current route is a versatile and salt-free method for synthesis of both aliphatic and aromatic 1-substituted and 1,1-disubstituted taurines.

  由硝基烯烃通过与乙基黄原酸钠钠的迈克尔加成反应，用过甲酸酸氧化并在钯/碳粉存在下用氢还原反应，由硝基烯烃合成一系列1-取代和1,1-二取代的牛磺酸。目前的路线是一种通用且无盐的方法，用于合成脂族和芳族1取代和1,1-二取代的牛磺酸。
• Facile synthesis of various substituted taurines, especially syn- and anti-1,2-disubstituted taurines, from nitroolefins
  作者：Ning Chen、Jiaxi Xu

  DOI：10.1016/j.tet.2012.01.031

  日期：2012.3

  Taurine and substituted taurines present a group of important structural elements in many natural products. Various substituted taurines, including 1- and 2-substituted, 1,1-, syn-1,2-, and anti-1,2-disubstituted taurines, were synthesized from the corresponding nitroolefins via Michael addition with thioacetic acid, oxidation with peroxyformic acid, and the catalytic hydrogenation under the catalysis of palladium on carbon or platinum dioxide. It is a general, versatile, and salt-free method for the preparation of substituted taurines, especially for syn- and anti-1,2-disubstituted taurines and some taurines with more bulky substituents. The stereostructures of both syn- and anti-1,2-disubstituted taurines were deduced from the nitroalkyl thioacetates in the Michael addition, which were identified via the Karplus equation analysis and computational analysis, and finally confirmed by the XRD single crystal analysis. The diastereoselectivity in the Michael addition was rationalized with the Cram rule. (C) 2012 Elsevier Ltd. All rights reserved.