5-氨基戊醛 | 14049-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-氨基戊醛
• 英文名称: δ-aminopentanal
• 英文别名: 5-aminopentyraldehyde；4-aminobutyraldehyde；5-aminopentanal
• CAS: 14049-15-1
• 化学式: C₅H₁₁NO
• mdl: MFCD19203763
• 分子量: 101.148
• InChiKey: SZBGXBOFCGNPEU-UHFFFAOYSA-N

物化性质

• 熔点：
  39 °C
• 沸点：
  172.3±23.0 °C(Predicted)
• 密度：
  0.902±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  7
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氨基戊醛 在 potassium carbonate 作用下， 以 甲酸 、 二氯甲烷 、 水 为溶剂， 反应 0.08h， 生成 N-(p-toluenesulfonyl)hex-5-enaldimine
  参考文献：
  名称：

  通过镍(0)-催化的C-C键裂解烯丙胺的烯基交换

  摘要：

  开发了烯丙胺和烯烃之间通过镍催化的 CC 键断裂和形成的官能团交换反应。该反应为烯丙胺的合成提供了一种新方案，不需要使用不稳定的亚胺底物，烯丙胺广泛用于精细化学品、药物和农用化学品的生产。

  DOI：

  10.1021/jacs.8b13251
• 作为产物：
  描述：

  N-(α-Tetrahydropyranyl)-amino-essigsaeureethylester 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 5-氨基戊醛
  参考文献：
  名称：

  Tesse,J., Bulletin de la Societe Chimique de France, 1973, p. 787 - 793

  摘要：

  DOI：

文献信息

• Magnetic nanoparticles loaded on mobile crystalline material-41: preparation, characterization and application as a novel material for the construction of an electrochemical nanosensor
  作者：Mohammad Hasanzadeh、Arash Bahrami、Mohammad Alizadeh、Nasrin Shadjou

  DOI：10.1039/c3ra42393j

  日期：——

  Herein, we envisage the possibility of preparing stable magnetic mobile crystalline material-41 using cetyltrimethylammonium bromide and Fe3O4 nanoparticles. The Fe3O4 nanoparticles are incorporated into mobile crystalline material-41 in hydrothermal conditions. The prepared mesoporous sample was characterized by Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy (SEM) and nitrogen adsorption–desorption techniques. The electrochemical behavior of cadaverine, histamine and putrescine was investigated on magnetic mobile crystalline material-41 (MCM-41-Fe2O3) modified carbon paste electrodes (CPEs). Due to the very large surface area (1213 m2 g−1) and the remarkable electrocatalytic properties of Fe2O3 nanoparticles, MCM-41-Fe2O3 exhibits potent electrocatalytic activity toward the electrooxidation of some selected biogenic amines. MCM-41-Fe2O3-CPEs provide new capabilities for electrochemical sensing by combining the advantages of Fe2O3 magnetic nanoparticles and MCM-41 with a very large surface area. The process of oxidation and its kinetics were established by using cyclic voltammetry, chronoamperometry techniques, and also, steady state polarization measurements. The apparent electron transfer rate constant (Ks) and transfer coefficient (α) were determined by cyclic voltammetry and were approximately 6.2 s−1 and 0.48, respectively. The linear concentration ranges of the proposed sensors for cadaverine, histamine and putrescine were 0.1–10, 0.01–0.5 and 0.9–35 μM, respectively. Finally, the applicability of the sensor to the determination of electroactive biogenic amine concentrations in fish samples has been successfully demonstrated.

  在此，我们设想利用十六烷基三甲基溴化铵和Fe3O4纳米颗粒制备稳定的磁性移动晶体材料41。 纳米颗粒在水热条件下被纳入移动晶体材料41中。所制备的介孔样品通过傅里叶变换红外光谱（FTIR）、X射线衍射（XRD）、扫描电子显微镜（SEM）和氮气吸附-脱附技术进行了表征。我们在改性碳糊电极（CPEs）上研究了尸胺、组胺和腐胺的电化学行为。由于Fe2O3纳米颗粒具有非常大的表面积（1213 m² g⁻¹）和显著的电催化特性，MCM-41- 对某些选定的生物胺的电氧化表现出强大的电催化活性。MCM-41- -CPEs通过结合 磁性纳米颗粒和具有非常大表面积的MCM-41的优点，为电化学传感提供了新的能力。通过循环伏安法、计时安培法以及稳态极化测量确定了氧化过程及其动力学。表观电子转移速率常数（Ks）和转移系数（α）通过循环伏安法测定，分别约为6.2 s⁻¹和0.48。所提传感器对尸胺、组胺和腐胺的线性浓度范围分别为0.1–10、0.01–0.5和0.9–35 μM。最后，成功演示了传感器在鱼样品中测定电活性生物胺浓度的适用性。
• Substrate-Selective Supramolecular Tandem Assays: Monitoring Enzyme Inhibition of Arginase and Diamine Oxidase by Fluorescent Dye Displacement from Calixarene and Cucurbituril Macrocycles
  作者：Werner M. Nau、Garima Ghale、Andreas Hennig、Hüseyin Bakirci、David M. Bailey

  DOI：10.1021/ja904165c

  日期：2009.8.19

  stronger fluorescence in its complexed state, which leads to a switch-on fluorescence response upon enzymatic oxidation. It is demonstrated that tandem assays can be successfully used to probe the inhibition of enzymes. Inhibition constants were estimated for the addition of known inhibitors, i.e., S-(2-boronoethyl)-L-cysteine and 2(S)-amino-6-boronohexanoic acid for arginase and potassium cyanide for

  适度选择性的主客体结合与令人印象深刻的酶转化特异性相结合，可以实时监测均相溶液中的酶反应。所得酶测定（“超分子串联测定”）利用荧光染料与大环宿主的动态结合，与底物和产物的结合竞争。研究了两个酶促反应的例子：精氨酸酶催化的精氨酸水解为鸟氨酸和二胺氧化酶将尸胺氧化为 5-氨基戊醛，其中底物对大环化合物的亲和力高于产物（“底物选择性测定法” ”）。底物的消耗使荧光染料在酶促反应过程中进入大环，这导致所需的荧光响应。对于精氨酸酶，使用对磺化杯[4]芳烃作为大环化合物，其与精氨酸的结合常数为 6400 M(-1)，与鸟氨酸的结合常数为 550 M(-1)，与选定的荧光结合常数为 60,000 M(-1)染料（1-氨基甲基-2,3-二氮杂双环[2.2.2]辛-2-烯）；该染料在其络合状态下显示出较弱的荧光，这导致在酶促反应过程中关闭荧光响应。对于二胺氧化酶，葫芦[7] uril (CB7) 用作大环，显示结合常数为
• An Engineered Alcohol Oxidase for the Oxidation of Primary Alcohols
  作者：Rachel S. Heath、William R. Birmingham、Matthew P. Thompson、Andreas Taglieber、Laurent Daviet、Nicholas J. Turner

  DOI：10.1002/cbic.201800556

  日期：——

  Turn up the heat: Alcohol oxidases require no cofactor or cofactor recycling system for catalysis, just O2, but their use is limited by activity and substrate scope. An alcohol oxidase with a broad scope for primary alcohol oxidations has now been evolved. Further improvements were made to enzyme stability and demonstrated by its increased thermostability and solvent tolerance.

  调高热量：醇氧化酶不需要催化的辅助因子或辅助因子循环系统，只需O 2即可，但其使用受到活性和底物范围的限制。现在已经开发出具有广泛伯醇氧化范围的醇氧化酶。酶的稳定性得到了进一步的改善，并通过增加的热稳定性和耐溶剂性得到证明。
• Amino Aldehydes Revisited
  作者：Luuk Mestrom、Paula Bracco、Ulf Hanefeld

  DOI：10.1002/ejoc.201701213

  日期：2017.12.22

  The enzymatic oxidation of amino alcohols was studied to address the long-standing problem of product stability. Amino aldehydes, the much sought after and unstable compounds, can be generated under mild conditions when they are immediately protected. Utilizing a range of alcohol dehydrogenases (ADHs) and semicarbazide as scavenger, the enantioselective synthesis of protected amino aldehydes is possible

  研究氨基醇的酶促氧化以解决长期存在的产品稳定性问题。氨基醛是备受追捧的不稳定化合物，当它们立即受到保护时，可以在温和条件下生成。利用一系列醇脱氢酶 (ADH) 和氨基脲作为清除剂，可以对受保护的氨基醛进行对映选择性合成。来自氧化葡糖杆菌 (GoGDH) 的甘油脱氢酶显示出优异的对映选择性，但底物范围有限，而马肝 ADH 催化广泛的转化，但对映选择性较低。
• Potent and Selective Non-Peptidic Inhibitors of Endothelin-Converting Enzyme-1 with Sustained Duration of Action
  作者：Stéphane De Lombaert、Louis Blanchard、Lisa B. Stamford、Jenny Tan、Eli M. Wallace、Yoshitaka Satoh、John Fitt、Denton Hoyer、David Simonsbergen、John Moliterni、Nicholas Marcopoulos、Paula Savage、Mary Chou、Angelo J. Trapani、Arco Y. Jeng

  DOI：10.1021/jm990507o

  日期：2000.2.1

  Functionally, 27and 29 were the two most efficacious compounds from this study, producing sustained inhibition of ECE-1 activity in rats, as measured by their ability to block the hypertensive effects induced by big ET-1. This profile was similar to that of a potent ET(A)/ET(B) dual receptor antagonist, SB 209670. Due to their favorable in vitro and in vivo profiles, 27 (CGS 34043) and 29 (CGS 35066) constitute

  人类内皮素转化酶-1（ECE-1）的有效和选择性非肽类抑制剂已被设计为体内内皮素（ET-1）生产的潜在调节剂。由于其独特的结构特征和在体内的长效作用，双重ECE-1和中性肽链内切酶24.11（NEP）抑制剂CGS 26303被选为进一步优化效能和选择性的诱人先导。用构象受限的3-二苯并呋喃基取代CGS 26303的P（1）'联苯取代基导致更有效和更具选择性的ECE-1抑制剂，如四唑27。这种P（1）'修饰的显着效果首次允许膦酰基甲基羧酸（如29）显示出强效（IC（50）= 22 nM）和选择性（相对NEP的104倍）ECE-1抑制作用。开发了新的α-氨基酸（S）-3-二苯并呋喃-3-基丙氨酸中间体的化学合成方法，并设计了改进的程序来生成取代的α-氨基烷基膦酸以支持各种类似物的生产。尽管通过添加P（1）侧链偶尔可以实现内在ECE-1抑制能力的额外提高，但这些化合物（例如43a）在大ET-1加