2-[(2-mercaptoethyl)amino]ethanoic acid hydrochloride | 6940-79-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(2-mercaptoethyl)amino]ethanoic acid hydrochloride
• 英文别名: 2-mercaptoethyl-N-glycine hydrochloride；mercaptoethylglycine hydrochloride；2-[(thioethyl)amino]acetic acid hydrochloride；N-Carboxymethyl-2-aminoethane thiol hydrochloride；2-(2-sulfanylethylamino)acetic acid;hydrochloride
• CAS: 6940-79-0
• 化学式: C₄H₉NO₂S*ClH
• 分子量: 171.648
• InChiKey: YXTHZMMMPYIAJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.43
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-联吡啶 、 [ReOCl₃(PPh₃)₂] 、 水 、 2-[(2-mercaptoethyl)amino]ethanoic acid hydrochloride 在 sodium acetate 作用下， 以 甲醇 为溶剂， 以54%的产率得到[ReO(2-mercaptoethyl-N-glycine(-3H))(2,2'-bipyridine)]*H2O
  参考文献：
  名称：

  Synthesis and structural characterization of neutral “3+2” oxorhenium and oxotechnetium complexes of the 2-mercaptoethyl-N-glycine (SNO)/2,2′-bipyridine (NN) mixed ligand system

  摘要：

  Neutral. hexacoordinated "3 + 2" mixed ligand oxorhenium (1) and oxotechnetium (2) complexes of the general formula MO [SNO][NN]. where M = Re or Tc-99, SNO is 2-mercaptoethyl-N-glycine and NN is 2,2'-bipyridine (bpy), were synthesized by simultaneous action of the tridentate SNO and the bidentate NN ligand on ReOCl3(PPh3)(2) or (TcO)-Tc-99-gluconate precursors in a 1: 1: 1 molar ratio. Both complexes were characterized by elemental analysis, IR and NMR spectroscopy. X-ray structure determination of rhenium complex I revealed a distorted octahedral coordination geometry where the SNO donor atoms of the tridentate ligand and one bpy nitrogen atom occupy the equatorial positions of the octahedron, whereas the second bpy nitrogen atom and the oxo-group fill the apical positions. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2007.04.038
• 作为产物：
  描述：

  mercaptoethylglycine ethyl ester 在 盐酸 作用下， 反应 18.0h， 以33%的产率得到2-[(2-mercaptoethyl)amino]ethanoic acid hydrochloride
  参考文献：
  名称：

  Structural requirements for the sequestration of metabolically generated acetaldehyde

  摘要：

  Of a series of polyfunctional compounds containing amino, hydroxyl, or mercapto groups in conjunction with the carboxyl group, only the 1,2- or 1,3-disubstituted aminothiols, namely, D-(-)-penicillamine (1), L-cysteine (2), L-cysteinyl-L-valine (3), mercaptoethylglycine (4), and DL-homocysteine (12), showed any propensity to sequester acetaldehyde (AcH) when tested in vitro in a buffered system at pH 7.5. In vivo, however, only D-(-)-penicillamine (1) was effective in lowering ethanol-derived blood AcH in rats that had been treated with disulfiram and ethanol. These results suggest that, in addition to the functionality in the molecule, pharmacokinetic and metabolic factors must also be considered when designing AcH-sequestering agents for use in vivo.

  DOI：

  10.1021/jm00176a007

文献信息

• Versatile Synthesis of Secondary 2-Amino Thiols and/or Their Disulfides via Thiazolinium Salts
  作者：Guillaume Mercey、Jean-François Lohier、Annie-Claude Gaumont、Jocelyne Levillain、Mihaela Gulea

  DOI：10.1002/ejoc.200900514

  日期：2009.9

  Commercially available β-amino alcohols have been transformed into various secondary β-amino thiols and/or their disulfides by using methyl dithioacetate as a source of sulfur. The transformation involves a thiazolinium salt as a versatile key intermediate, which enables easy modulation of the product structure by varying the substituents on the heterocycle and the N-alkylating agent.(© Wiley-VCH Verlag

  通过使用二硫代乙酸甲酯作为硫源，已将市售的 β-氨基醇转化为各种仲 β-氨基硫醇和/或其二硫化物。该转化涉及作为通用关键中间体的噻唑啉盐，它可以通过改变杂环和 N-烷基化剂上的取代基轻松调节产品结构。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany , 2009)