4-amino-N-methylbutanamide | 23435-12-3

• 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: 4-amino-N-methylbutanamide
• 英文别名: H-Gaba-NMe；4-Amino-buttersaeuremethylamid
• CAS: 23435-12-3
• 化学式: C₅H₁₂N₂O
• mdl: MFCD09934786
• 分子量: 116.163
• InChiKey: IJUCBGPQWGGYBV-UHFFFAOYSA-N

物化性质

• 沸点：
  287.4±23.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 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：

  4-amino-N-methylbutanamide 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 23.58h， 生成 N-methyl-4-(3-propyl-thioureido)butyramide
  参考文献：
  名称：

  Fragmentation reactions of thiourea- and urea-compounds examined by tandem MS-, energy-resolved CID experiments, and theory

  摘要：

  Fragmentation reactions of thiourea- and urea-compounds, which are promising reagents for chemical crosslinking (XL), are investigated in detail by collision-induced dissociation (CID) experiments in a quadrupole ion trap (QIT), energy-resolved CID experiments, and computational modeling. For this study, an array of six labeled and unsymmetrical substituted thiourea- and urea-derivatives were synthesized, which allow unambiguous characterization of competing fragmentation pathways. The results of the QIT-CID-experiments are explored in detail for two compounds and confirmed by results for the other four. These results document the subtle competition of characteristic fragmentation pathways of this class of compounds. The multi dimensional investigations of the characteristic fragmentation reactions allow reliable structure proposals of prominent productions. Energy-dependent CID experiments on two of the six compounds lead to breakdown curves that show similar relative threshold energies for the formation of the product ions on which the functioning of the XL application relies. The experimental results are in full consistency with the results from in-depth computations. For the dominant fragmentations observed, the transition states for moving the proton from the most basic site of the precursor ion (the thiourea-sulfur or the urea carbonyl oxygen) to less basic heteroatoms in the protonated molecular ion is the necessary and decisive step that determines the extent of the charge-driven fragmentation processes that follow. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijms.2012.06.023
• 作为产物：
  描述：

  benzyl (4-(methylamino)-4-oxobutyl)carbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以> 99 %的产率得到4-amino-N-methylbutanamide
  参考文献：
  名称：

  氧化还原介导的连苯三酚基多酚的胺化

  摘要：

  已知淀粉样蛋白可通过胺化作用被天然多酚修饰。本研究采用体外和计算机方法研究了多酚和N -亲核试剂之间的氧化偶联机制。结果表明，具有连苯三酚亚结构和 C4a 位吸电子基团的多酚最有效。这些见解可以在抗淀粉样蛋白生成的药物设计中发挥至关重要的作用。

  DOI：

  10.1002/chem.202303783

文献信息

• Amino-acids and peptides. Part IX. Some neighbouring-group amino–amide and hydroxy–amide interactions
  作者：Jacquita A. Davies、C. H. Hassall、I. H. Rogers

  DOI：10.1039/j39690001358

  日期：——

  Base-catalysed hydrolysis studies have provided evidence of neighbouring-group amino–amide interactions in compounds with the formulae H2N·[CH2]x·CO·NHMe (x= 3, 4, or 5), and in 6-aminodecane-10-lactam. Acid-catalysed hydrolysis studies have indicated that transannular hydroxy-amide interactions occur with 4-hydroxyhexane-6-lactam, 5-hydroxyoctane-8-lactam, and 6-hydroxydecane-10-lactam. The mechanisms

  碱催化的水解研究提供了在具有以下化学式的化合物H 2 N·[CH 2 ] x ·CO·NHMe（x = 3、4、5）和6-氨基癸烷中相邻基团氨基酰胺相互作用的证据。-10-内酰胺 酸催化的水解研究表明，环戊基羟基酰胺相互作用与4-羟基己烷-6-内酰胺，5-羟基辛烷-8-内酰胺和6-羟基癸烷-10-内酰胺发生。讨论了这些反应的机理以及此类过程在肽化学中的意义。
• Absence of stereoelectronic control in hydrolysis of cyclic amidines
  作者：Charles L. Perrin、Oswaldo. Nunez

  DOI：10.1021/ja00279a055

  日期：1986.9

  L'hydrolyse de trois amidines cycliques a 6 chainons donne essentiellement un aminoamide (produit de decyclisation) et seulement 3,9% de lactame (produit theorique). Par contre l'hydrolyse de trois amidines cycliques a 5 ou 7 chainons donne environ 50% de lactame

  L'hydrolyse de trois camides cycliques a 6 chainons donne essentiellement unaminoamide (produit de decyclisation) et seulement 3,9% de lactame (produit theorique)。Par contre l'hydrolyse de trois amidines cycliques a 5 ou 7 chainons donne environment 50% de内酰胺
• Dado; Gellman, Journal of the American Chemical Society, 1994, vol. 116, # 3, p. 1054 - 1062
  作者：Dado、Gellman

  DOI：——

  日期：——
• Novel 2,7-Dialkyl-Substituted 5(<i>S</i>)-Amino-4(<i>S</i>)-hydroxy-8-phenyl-octanecarboxamide Transition State Peptidomimetics Are Potent and Orally Active Inhibitors of Human Renin
  作者：Richard Göschke、Stefan Stutz、Vittorio Rasetti、Nissim-Claude Cohen、Joseph Rahuel、Pascal Rigollier、Hans-Peter Baum、Peter Forgiarini、Christian R. Schnell、Trixie Wagner、Markus G. Gruetter、Walter Fuhrer、Walter Schilling、Frédéric Cumin、Jeanette M. Wood、Jürgen Maibaum

  DOI：10.1021/jm070314y

  日期：2007.10.1

  The action of renin is the rate-limiting step of the renin-angiotensin system (RAS), a key regulator of blood pressure. Effective renin inhibitors directly block the RAS entirely at source and, thus, may provide a vital weapon for hypertension therapy. Our efforts toward identifying novel small-molecule peptidomimetic renin inhibitors have resulted in the design of transition-state isosteres such as I bearing an all-carbon 8-phenyl-octanecarboxamide framework. Optimization of the extended P3 portion of I and extensive P2' modifications provided analogues with improved in vitro potencies in the presence of plasma. X-ray resolution of rhrenin/38a in the course of SAR work surprisingly unveiled the exploitation of a previously unexplored pocket (S3(SP)) important for strong binding affinities. Several inhibitors demonstrated oral efficacy in sodium-depleted marmosets. The most potent, 38a, induced dose-dependently a pronounced reduction in mean arterial blood pressure, paralleled by complete blockade of active plasma renin, up to 8 h post-dose. Oral bioavailability of 38a was 16% in marmosets.
• Fragmentation reactions of thiourea- and urea-compounds examined by tandem MS-, energy-resolved CID experiments, and theory
  作者：Francesco Falvo、Lukas Fiebig、Frank Dreiocker、Ran Wang、P.B. Armentrout、Mathias Schäfer

  DOI：10.1016/j.ijms.2012.06.023

  日期：2012.12

  Fragmentation reactions of thiourea- and urea-compounds, which are promising reagents for chemical crosslinking (XL), are investigated in detail by collision-induced dissociation (CID) experiments in a quadrupole ion trap (QIT), energy-resolved CID experiments, and computational modeling. For this study, an array of six labeled and unsymmetrical substituted thiourea- and urea-derivatives were synthesized, which allow unambiguous characterization of competing fragmentation pathways. The results of the QIT-CID-experiments are explored in detail for two compounds and confirmed by results for the other four. These results document the subtle competition of characteristic fragmentation pathways of this class of compounds. The multi dimensional investigations of the characteristic fragmentation reactions allow reliable structure proposals of prominent productions. Energy-dependent CID experiments on two of the six compounds lead to breakdown curves that show similar relative threshold energies for the formation of the product ions on which the functioning of the XL application relies. The experimental results are in full consistency with the results from in-depth computations. For the dominant fragmentations observed, the transition states for moving the proton from the most basic site of the precursor ion (the thiourea-sulfur or the urea carbonyl oxygen) to less basic heteroatoms in the protonated molecular ion is the necessary and decisive step that determines the extent of the charge-driven fragmentation processes that follow. (C) 2012 Elsevier B.V. All rights reserved.