N-(对甲苯磺酰基)苏氨酸 | 34235-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(对甲苯磺酰基)苏氨酸
• 英文名称: N-(toluene-4-sulfonyl)-allothreonine
• 英文别名: N-(Toluol-4-sulfonyl)-allothreonin；(2S,3S)-3-hydroxy-2-[(4-methylphenyl)sulfonylamino]butanoic acid
• CAS: 34235-88-6；43188-50-7；43188-51-8；43188-52-9；70275-29-5；91280-33-0
• 化学式: C₁₁H₁₅NO₅S
• 分子量: 273.31
• InChiKey: SZILOGOOPIXJAQ-WPRPVWTQSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  489.4±55.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(对甲苯磺酰基)苏氨酸 在 palladium on activated charcoal 吡啶 、 氢气 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 54.0h， 生成 ((S)-2-naphthylCO2CH(CH3))C2HO2B(C6H5)N(SO2-p-tolyl)
  参考文献：
  名称：

  对映选择性路易斯酸催化无环烯酮的Mukaiyama-Michael反应。异苏氨酸衍生的草氮杂硼烷酮催化。

  摘要：

  异苏氨酸衍生的O-芳酰基-B-苯基-N-甲苯磺酰基-1,3,2-氧杂硼硼烷-5-酮1g，n催化无环烯酮与三甲基甲硅烷基乙烯酮S，O-乙缩醛的不对称Mukaiyama-Michael反应具有高对映选择性。通过使用10 mol％的催化剂，一系列烯基甲基酮被成功用作Michael受体，ee值为85-90％。已发现使用2，6-二异丙基苯酚和叔丁基甲基醚作为添加剂对于在这些反应中实现高对映选择性是必不可少的。根据阻滞Si（+）催化的外消旋途径来讨论添加剂的作用，这会严重恶化不对称Mukaiyama-Michael反应的对映选择性。基于催化剂结构与对映选择性之间的相关性，提出了一种不对称诱导的工作模型。

  DOI：

  10.1021/jo035379x
• 作为产物：
  描述：

  L-别苏氨酸 生成 N-(对甲苯磺酰基)苏氨酸
  参考文献：
  名称：

  Izumiya, Nippon Kagaku Zasshi, 1949, vol. 70, p. 447

  摘要：

  DOI：

文献信息

• Development of amino acid conjugated sulfonamides as potent antiulcer agent
  作者：Shakti Prasanna Sahoo、Bharat Bhusan Subudhi

  DOI：10.1007/s00044-013-0891-y

  日期：2014.6

  A series of 2-[(4-methylphenyl) sulfonyl] amino}-3-sulfanylpropanoic acid (1a) and its analogs 1b-j have been synthesized. These compounds were screened for their in vivo efficacy in pyloric ligation model. Compounds 1a and 1b with higher antiulcer potential were further screened in other gastric models to explore the mode of antiulcer action. To further understand the mode of action, in vitro inhibition of H+/K+ ATPase activity in gastric microsome isolated from rat stomach was studied. This was rationalized by in silico experiments.
• Synthesis, characterization, and cytotoxicity of platinum(II)/palladium(II) complexes with 4-toluenesulfonyl-L-amino acid dianion and diimine/diamine
  作者：Luwei Li、Jinchao Zhang、Lili Ma、Zhilei Zhang、Shuxiang Wang、Shenghui Li、Guoqiang Zhou

  DOI：10.1080/00958972.2013.767447

  日期：2013.2.1

  Eight new platinum(II)/palladium(II) complexes with 4-toluenesulfonyl-L-amino acid dianion and diimine/diamine ligands, [Pd(en)(Tsile)]center dot H2O (1), [Pd(bipy)(Tsile)] (2), [Pd(bipy)(Tsthr)]center dot 0.5H2O (3), [Pd(phen)(Tsile)]center dot 0.5H2O (4), [Pd(phen)(Tsthr)]center dot H2O (5), [Pd(bqu)(Tsthr)]center dot 1.5H2O (6), [Pt(en)(Tsser)] (7), and [Pt(en)(Tsphe)]center dot H2O (8), have been synthesized and characterized by elemental analyses, 1H NMR and mass spectrometry. The crystal structure of 7 has been determined by X-ray diffraction. Cytotoxicities were tested by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide and sulforhodamine B assays. The complexes exert cytotoxicity against HL-60, Bel-7402, BGC-823, and KB cell lines with 4 having the best cytotoxicity against HL-60, Bel-7402, and BGC-823 cell lines; the compounds are less cytotoxic than cisplatin.
• Synthesis of the Four Stereoisomeric Forms of α,β-Diaminobutyric Acid and Some Derivatives Suitable for Peptide Synthesis
  作者：Eric Atherton、Johannes Meienhofer

  DOI：10.1515/bchm2.1973.354.2.689

  日期：1973.1
• Asymmetric Mukaiyama−Michael Addition of Acyclic Enones Catalyzed by <i>a</i><i>llo</i>-Threonine-Derived <i>B</i>-Aryloxazaborolidinones
  作者：Toshiro Harada、Hiroyoshi Iwai、Hiroshi Takatsuki、Katsuhiro Fujita、Mikako Kubo、Akira Oku

  DOI：10.1021/ol016062r

  日期：2001.6.1

  [GRAPHICS]O-(2-Naphthoyl)-N-tosyl-L-allo-threonine B-phenyloxazaborolidinone catalyzes the asymmetric Mukaiyama-Michael addition of simple acyclic enones to give adducts of 54-85% ee, 2,6-Diisopropylphenal as an additive is demonstrated to effectively retard the undesirable Si+-catalyzed racemic pathway.
• Izumiya, Nippon Kagaku Zasshi, 1949, vol. 70, p. 447
  作者：Izumiya

  DOI：——

  日期：——