3-(aminooxy)propionic acid hydrochloride | 5251-77-4

• 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: 3-(aminooxy)propionic acid hydrochloride
• 英文别名: 3-aminyloxy-propionic acid ; hydrochloride；3-Aminyloxy-propionsaeure; Hydrochlorid；3-(Aminooxy)propanoic acid hydrochloride；3-aminooxypropanoic acid;hydrochloride
• CAS: 5251-77-4
• 化学式: C₃H₇NO₃*ClH
• mdl: MFCD00154400
• 分子量: 141.554
• InChiKey: XRRWTXUSRDXCLW-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.51
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  72.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  3-(aminooxy)propionic acid hydrochloride 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 异噁唑啉-3-酮
  参考文献：
  名称：

  3-Isoxazolidone from jack bean seedlings

  摘要：

  DOI：

  10.1016/s0031-9422(00)84164-3
• 作为产物：
  描述：

  异噁唑啉-3-酮 在 盐酸 作用下， 反应 1.0h， 以0.2 g的产率得到3-(aminooxy)propionic acid hydrochloride
  参考文献：
  名称：

  3-Isoxazolidone from jack bean seedlings

  摘要：

  DOI：

  10.1016/s0031-9422(00)84164-3

文献信息

• 17-(O-(2-Carboxyethyl)oxime) Derivatives of Androstanes of 3-Hydroxy-5α-, -5β-, -5-ene and 3-Oxo-4-ene Series
  作者：Vladimír Pouzar、Ivan Černý

  DOI：10.1135/cccc19950137

  日期：——

  Androstane 17-(O-(2-carboxyethyl)oxime) derivatives were prepared either by the reaction of 17-keto derivatives with corresponding substituted hydroxylamine or by the addition of 17-oximino derivatives to the alkyl acrylate and subsequent hydrolysis. Oxidation of the hydroxy group in position 3 in derivatives of this type was performed either by the Oppenauer reaction, transforming 5-ene derivatives into 3-oxo-4-enes, or with Jones reagent in the case of saturated 5α- or 5β-derivatives. Configuration 17E in the whole series of oximes was confirmed by the ¹H and ¹³C NMR spectroscopy.

  雄烷17-(O-(2-羧乙基)肟)衍生物可以通过17-酮衍生物与相应取代羟胺的反应或通过将17-肟衍生物加入烷基丙烯酸酯并随后水解来制备。在这类衍生物中，位置3的羟基氧化可以通过Oppenauer反应将5-烯衍生物转化为3-酮-4-烯，或者在饱和的5α-或5β-衍生物中使用Jones试剂来进行。整个肟系列中17E构型通过¹H和¹³C核磁共振谱确认。
• Synthesis of Steroid O-(ω-Hydroxyalkyl)oximes by Reduction of Corresponding O-(ω-Carboxyalkyl)oxime Derivatives
  作者：Tereza Slavíková、Vladimír Pouzar、Ivan Černý

  DOI：10.1135/cccc19980557

  日期：——

  Steroid O-(ω-hydroxyalkyl)oximes with varying alkyl chain length were prepared from the corresponding carboxylic acids using the reduction of mixed anhydrides with sodium borohydride. An unexpected reaction course was observed with O-(2-carboxyethyl)oximes of 3-oxo-4-ene steroids, where a 4,5-dihydroisoxazol-3(2H)-one derivative was formed as a side product.

  类固醇O-(ω-羟基烷基)肟类化合物通过相应羧酸的混合酐还原制备而成。对3-酮-4-烯类类固醇的O-(2-羧乙基)肟类化合物观察到了意外的反应过程，形成了4,5-二氢异噁唑-3(2H)-酮衍生物作为副产物。
• Monoaryl derivatives as transthyretin fibril formation inhibitors: Design, synthesis, biological evaluation and structural analysis
  作者：Lidia Ciccone、Susanna Nencetti、Nicolo Tonali、Carole Fruchart-Gaillard、William Shepard、Elisa Nuti、Caterina Camodeca、Armando Rossello、Elisabetta Orlandini

  DOI：10.1016/j.bmc.2020.115673

  日期：2020.9

  deposition of amyloid fibrils. Small molecules, able to bind in T4 binding sites and stabilize the TTR tetramer, are interesting tools to treat and prevent systemic ATTR amyloidosis. We report here the synthesis, in vitro evaluation and three-dimensional crystallographic analyses of new monoaryl-derivatives in complex with TTR. Of the derivatives reported here, the best inhibitor of TTR fibrillogenesis

  运甲状腺素蛋白（TTR）是富含ß-sheet的同四聚体蛋白，可在血浆和脑脊液中转运甲状腺素（T4）和视黄醇。TTR还与淀粉样蛋白β相互作用，在阿尔茨海默氏病中起保护作用。天然运甲状腺素蛋白（TTR）四聚体的解离被广泛接受为TTR淀粉样蛋白原纤维形成的关键步骤，并负责淀粉样蛋白原纤维的细胞外沉积。能够结合T4结合位点并稳定TTR四聚体的小分子是治疗和预防全身性ATTR淀粉样变性的有趣工具。我们在这里报告了新的单芳基衍生物与TTR配合物的合成，体外评估和三维晶体学分析。在本文报道的衍生物中，TTR纤维化的最佳抑制剂是1d，表现出类似于二氟尼醛的活性。
• α-Aminoacyl derivatives of aminobenzoic acid and of amino-oxy-acids by reaction of their hydrochlorides with amino-acid N-carboxyanhydrides
  作者：Y. Knobler、S. Bittner、D. Virov、Max Frankel

  DOI：10.1039/j39690001821

  日期：——

  The reaction of amino-acid N-carboxyanhydrides with hydrochlorides of aminobenzoic acids and of amino-oxy-acids gave amino-acid amides in a one-step synthesis. The coupling of L-alanine N-carboxyanhydride with anthranilic and with p-aminobenzoic acid hydrochloride gave peptide-like compounds of high optical activity, indicating the presence of little or no racemate. Glycyl and DL-phenylalanyl amides

  氨基酸N-羧基酐与氨基苯甲酸和氨基氧-酸的盐酸盐反应，通过一步合成得到氨基酸酰胺。L-丙氨酸N-羧基酐与邻氨基苯甲酸酯和对氨基苯甲酸盐酸盐的偶合产生具有高光学活性的肽样化合物，表明存在很少或没有外消旋体。以此方式获得了具有氨基苯甲酸的甘氨酰和DL-苯丙氨酰胺，并且通过N-羧基酸酐与对氨基苯甲酰基-L-谷氨酸盐酸盐的反应形成了三聚体。
• Lengthening of the Alkyl Chain in Steroid O-(ω-Carboxyalkyl)oximes by Wittig Reaction
  作者：Vladimír Pouzar、Tereza Slavíková、Ivan Černý

  DOI：10.1135/cccc19981623

  日期：——

  The steroid O-alkyloximes with various alkyl length (2-4 carbons) and with terminal hydroxyl groups were oxidized to aldehydes and their Wittig reaction with triethyl phosphonoacetate was studied. Oximes derived from 17-oxoandrost-5-en-3β-yl acetate and from 7-oxo and 19-oxocholest-5-en-3β-yl acetate were used. Except of 7- and 19-[O-(2-hydroxyethyl)]oximes, all the hydroxyalkyloximes gave successively aldehydes and corresponding unsaturated esters. The method is useful for the lengthening of the carbon chain in ω-substituted O-alkyloximes.

  使用具有不同碳链长度（2-4碳）和端羟基的O-烷氧肟类固醇被氧化为醛，并研究了它们与三乙基膦酸乙酯的维特格反应。使用了从17-氧代雄烯-5-烯-3β-乙酸酯和7-氧代、19-氧代胆甾-5-烯-3β-乙酸酯衍生的肟类。除了7-和19-[O-(2-羟乙基)]肟外，所有羟基烷氧肟都成功地生成了相应的醛和不饱和酯。该方法对于延长ω-取代O-烷氧肟中的碳链很有用。