(+/-)-erythro-2-Amino-1,2-diphenylethanesulfonic acid | 123191-68-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+/-)-erythro-2-Amino-1,2-diphenylethanesulfonic acid
• 英文别名: (1RS,2SR)-2-amino-1,2-diphenylethanesulfonic acid；2-amino-1,2-diphenylethanesulfonic acid；(1R,2S)-2-amino-1,2-diphenylethanesulfonic acid
• CAS: 123191-68-4；123191-69-5
• 化学式: C₁₄H₁₅NO₃S
• 分子量: 277.344
• InChiKey: JZCNDWNXHKTIIR-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (1-硝基-2-苯乙烯基)苯 在 甲酸 、 三正丁胺 、 palladium 10% on activated carbon 、 氢气 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 1.0h， 生成 (+/-)-erythro-2-Amino-1,2-diphenylethanesulfonic 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

• Synthesis of (±)-<i>erythro</i>- and (±)-<i>threo</i>-1,2-Diphenyltaurines by Diastereoselective Hydrolysis of Thiazetidine 1,1-Dioxides
  作者：Evelyne Grunder、Gérard Leclerc

  DOI：10.1055/s-1989-27176

  日期：——

  The disubstituted analogs of taurine, (±)-erythro- and (±)-threo-2-amino-1,2-diphenyl-ethanesulfonic acids were prepared from (±)-cis- and (±)-trans-2-benzyl-3,4-diphenyl-1,2-thiazetidine 1,1-dioxides, respectively, by diastereoselective hydrolysis of the sulfonamide bond, followed by N-debenzylation.

  通过非对映选择性水解磺酰胺键，然后进行 N-脱苄基反应，分别从(±)-顺式和(±)-反式-2-苄基-3,4-二苯基-1,2-噻嗪-1,1-二氧杂环丁烷制备了牛磺酸的二取代类似物--(±)-赤式和(±)-苏式-2-氨基-1,2-二苯基乙磺酸。
• Amino-Sulfonation of Alkenes in a Three-Component Reaction
  作者：Franca M. Cordero、Martina Cacciarini、Fabrizio Machetti、Francesco De Sarlo

  DOI：10.1002/1099-0690(200204)2002:8<1407::aid-ejoc1407>3.0.co;2-i

  日期：2002.4

  2-Aminoalkanesulfonic acids have been synthesized by a three-component alkene/(SO3DMF)-D-./acetonitrile reaction, followed by hydrolysis, Trifluoromethanesulfonic acid was added to the amino-sulfonation mixture to accelerate the reaction and prevent the competitive formation of by-products. The reported two-step procedure provided a concise and versatile approach to new analogues of the natural amino acid taurine.((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
• GRUNDER, EVELYNE;LECLERC, GERARD, SYNTHESIS,(1989) N, C. 135-137
  作者：GRUNDER, EVELYNE、LECLERC, GERARD

  DOI：——

  日期：——