3-氨基-N-甲基丙酰胺盐酸盐 | 51739-61-8

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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
• 中文名称: 3-氨基-N-甲基丙酰胺盐酸盐
• 英文名称: methyl 3-aminopropionamide hydrochloride
• 英文别名: N-methyl β-aminopropionamide hydrochloride；β-alanine N-methylamide hydrochloride；3-amino-N-methylpropanamide hydrochloride；3-amino-N-methylpropionamide hydrochloride；3-amino-N-methylpropanamide;hydrochloride
• CAS: 51739-61-8
• 化学式: C₄H₁₀N₂O*ClH
• mdl: MFCD10686841
• 分子量: 138.597
• InChiKey: BYWCMHMCAMQJIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.49
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  3-甲酰氯-5-硝基苯甲酸甲酯 、 3-氨基-N-甲基丙酰胺盐酸盐 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 生成 methyl 3-[[3-(methylamino)-3-oxopropyl]carbamoyl]-5-nitrobenzoate
  参考文献：
  名称：

  三碘间苯二甲酸单氨基酸酰胺的介绍及其作为 X 射线造影剂的用途

  摘要：

  以硝基间苯二甲酸单甲酯氯化物 (1) 为原料，与氨基酸酰胺 2 反应生成相应的硝基间苯二甲酸衍生物 3，经皂化、催化加压加氢、碘化，最后酰化得到标题化合物 7。非常适合用作尿路、血管和脊髓造影的 X 射线造影剂。

  DOI：

  10.1002/ardp.19733061106
• 作为产物：
  描述：

  苄基(2-(甲基氨基甲酰基)乙基)氨基甲酸酯 在 palladium/active carbon 氢气 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 4.0h， 生成 3-氨基-N-甲基丙酰胺盐酸盐
  参考文献：
  名称：

  [EN] 5,7-DIAMINOPYRAZOLO`4,3-D!PYRIMIDINES USEFUL IN THE TREATMENT OF HYPERTENSION
  [FR] 5,7-DIAMINOPYRAZOLO`4,3-D!PYRIMIDINES UTILES POUR LE TRAITEMENT DE L'HYPERTENSION

  摘要：

  这项发明涉及到式(I)的化合物。

  公开号：

  WO2004096810A1

文献信息

• Stereochemical Control of Hairpin Formation in β-Peptides Containing Dinipecotic Acid Reverse Turn Segments
  作者：Yong Jun Chung、Bayard R. Huck、Laurie A. Christianson、Heather E. Stanger、Susanne Krauthäuser、Douglas R. Powell、Samuel H. Gellman

  DOI：10.1021/ja993416p

  日期：2000.5.1

  substitution patterns for residues that form strands in an antiparallel β-peptide sheet (Krauthauser et al. J. Am. Chem. Soc. 1997, 119, 11719), and we have shown that a dinipecotic acid segment can promote sheet-type interactions between attached strand residues (Chung et al. J. Am. Chem. Soc. 1998, 120, 10555). Here we compare all four possible configurations of the dinipecotic acid segment, (R,S), (S,R)

  我们研究了一系列 β-氨基酸四聚体之间的共价结构和构象倾向之间的关系。这些实验集中在发夹折叠图案上。在常规肽中，β-折叠二级结构的最小增量是“β-发夹”，其中两条链通过一个短环连接。目前的研究旨在优化 β-肽之间的发夹稳定性。我们实验室以前的工作已经确定了在反平行 β 肽片中形成链的残基的最佳替代模式（Krauthauser 等人 J. Am. Chem. Soc. 1997, 119, 11719），并且我们已经证明片段可以促进连接的链残基之间的片式相互作用（Chung 等人 J. Am. Chem. Soc. 1998, 120, 10555）。在这里，我们比较了二尼泊松酸片段的所有四种可能构型，(R,S)、(S,R)、(R,R) 和 (S,S)，以了解用一组恒定的对映体诱导片层形成的能力纯链残基。我们证明两者...
• Enantioselective alkylation and protonation of prochiral enolates in the asymmetric synthesis of β-amino acids
  作者：Omar Muñoz-Muñiz、Eusebio Juaristi

  DOI：10.1016/s0040-4020(03)00578-7

  日期：2003.6

  Achiral 1-benzoyl-3-methylperhydropyrimidin-4-one (1) was deemed a useful, potential precursor for the enantioselective synthesis of alpha-substituted beta-amino acids. Pyrimidinone 1 was prepared from inexpensive beta-aminopropanoic acid in 62% overall yield. Prochiral enolate derivative 1-Li was alkylated in good yield and moderate enantioselectivity in the presence of chiral amines (S)-8, (S,S)-9, (S,S)-10, or (-)-sparteine. The enantioselectivity of the alkylation process is highest in toluene as the solvent and in the presence of lithium bromide as additive. The racemic alkylated derivatives 2 and 3 were readily metallated with LDA to give prochiral enolates 2-Li and 3-Li, that were reprotonated with novel chiral phenolic acids (S)-11, (S,S)-12, (S)-13, and (S,S)-14 in moderate enantioselectivity in the case of 2-Li and good enantioselectivity in the case of 3-Li. The acid (6N HCl) hydrolysis of enantioenriched 2 and 3 proceeded in good yield and without racemization to afford alpha-alkyl-beta-amino acids 4 and 5, respectively. (C) 2003 Published by Elsevier Science Ltd.
• Asymmetric synthesis of .beta.-amino acids. 1. Highly diastereoselective addition of a racemic .beta.-alanine enolate derivative to electrophiles
  作者：Eusebio Juaristi、Delia Quintana、Bernd Lamatsch、Dieter Seebach

  DOI：10.1021/jo00007a053

  日期：1991.3

  beta-Alanine, an inexpensive alpha-amino acid, was converted into the 2-tert-butylperhydropyrimidin-4-one derivative 2, which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of 2-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the tert-butyl group at C(2), which directs addition from the enolate face opposite to this group. The hydrolysis of the resulting adducts proceeds with 6 N hydrochloric acid to afford alpha-substituted beta-amino acids in good yields. These results pave the road to the development of a new asymmetric synthesis of enantiomerically pure alpha-substituted beta-amino acids.
• X-ray Crystallographic Study of Substituted Perhydropyrimidinones. Extreme Changes in Ring Conformation
  作者：Yara Ramírez-Quirós、Margarita Balderas、Jaime Escalante、Delia Quintana、Itzell Gallardo、Domingo Madrigal、Elies Molins、Eusebio Juaristi

  DOI：10.1021/jo991297q

  日期：1999.11.1

  X-ray crystal structures of 20 differently substituted perhydropyrimidin-4-ones are presented. Analysis of these data reveal a remarkable conformational sensitivity of a six-membered ring to substitution. Thus half-chair; envelope, boat, twist-boat, and intermediate conformations are found for the six-membered heterocycle, providing evidence for a relatively flat conformational energy surface in this ring, interpretation of the preferred conformations is advanced in terms of steric interactions among substituents and, in some cases, as the result of particular conformational (A(1,3) strain, anomeric) effects.
• Structural and Conformational Requisites in DNA Quadruplex Groove Binding: Another Piece to the Puzzle
  作者：Sandro Cosconati、Luciana Marinelli、Roberta Trotta、Ada Virno、Stefano De Tito、Romeo Romagnoli、Bruno Pagano、Vittorio Limongelli、Concetta Giancola、Pier Giovanni Baraldi、Luciano Mayol、Ettore Novellino、Antonio Randazzo

  DOI：10.1021/ja1003872

  日期：2010.5.12

  The study of DNA G-quadruplex stabilizers has enjoyed a great momentum in the late years due to their application as anticancer agents. The recognition of the grooves of these structural motifs is expected to result in a higher degree of selectivity over other DNA structures. Therefore, to achieve an enhanced knowledge on the structural and conformational requisites for quadruplex groove recognition, distamycin A, the only compound for which a pure groove binding has been proven, has been chemically modified. Surprisingly, structural and thermodynamic studies revealed that the absence of Coulombic interactions results in an unprecedented binding position in which both the groove and the 3' end of the DNA are occupied. This further contribution adds another piece to the so far elusive puzzle of the recognition between ligands and DNA quadruplexes and will serve as a platform for a rational design of new groove binders.