苄基铵乙酸盐 | 2182-52-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苄基铵乙酸盐
• 英文名称: benzylamine acetic acid
• 英文别名: benzylamine acetate；benzylammonium acetate；Einecs 218-560-1；acetic acid;phenylmethanamine
• CAS: 2182-52-7
• 化学式: C₂H₃O₂*C₇H₁₀N
• 分子量: 167.208
• InChiKey: MPPQYFREIJCHTB-UHFFFAOYSA-N

物化性质

• 熔点：
  144.5-145.5 °C(Solv: benzene (71-43-2))

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  苄基铵乙酸盐 在 sodium tetrahydroborate 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 31.5h， 生成
  参考文献：
  名称：

  Design, Synthesis, and Structural Analysis of Influenza Neuraminidase Inhibitors Containing Pyrrolidine Cores

  摘要：

  The discovery of (+/-)-(2S,3R,4R)-2-(trifluoroacetamido)methyl-3-amino-1-(N ' -ethyl-N ' -isopropylcarbamyl)pyrrolidine-4-earboxylic acid (A-192558, 20e) as a potent inhibitor of influenza neuraminidase (NA) is described. Efficient syntheses of two core structures, cis-3-(allyloxy-carbonyl)amino-1-(9 ' -fluorenylmethoxycarbonyl)pyrrolidine-4-carboxylic acid (7) and tert-butyl (+/-)(2S, 3R,4R)-2-aminomethyl-3-bis(tert-butyloxycarbonyl) amino-1-(N ' -ethyl-N ' -isopropylcarbamyl)pyrrolidine-4-carboxylate (18b), were developed. Starting with these core structures and using available structural information of the NA active site as the guide, analogues were synthesized in both the tri- and tetrasubstituted pyrrolidine series by means of high-throughput parallel synthesis in solid or solution phase for expeditious SAR. These studies accelerated the identification of(+/-)-(2S,3R,4R)-2-(trifluoroacetamido)methyl-3-amino-1-(N-ethyl-N-isopropylcarbamyl)pyrrolidine-4-carboxylate (20e, A-192558) as the most potent NA inhibitor in this series (IC50 = 0.2 muM against NA A and 8 muM against NA B). The X-ray crystallographic structure of A-192558 bound to NA revealed the predicted interaction of the carboxylic group with the positively charged pocket (Arg118, Arg292, Arg371) and interaction of the trifluoro-acetamino residue with the hydrophobic pocket (Ile222, Trp178) of the enzyme active site. Surprisingly, the ethyl and isopropyl groups of the urea functionality induced a conformational change of Glu276, turning the Glu276/Glu277 hydrophilic pocket, which normally accommodates the triglycerol side chain of substrate sialic acid, into an induced hydrophobic pocket.

  DOI：

  10.1021/jm000468c
• 作为产物：
  描述：

  在 溴化铵 作用下， 生成 苄基铵乙酸盐 、 mercury dibromide
  参考文献：
  名称：

  Pesci, L., Gazzetta Chimica Italiana, 1896, vol. 26, # II, p. 54 - 75

  摘要：

  DOI：

文献信息

• Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?
  作者：Nao Tanaka、Toyonobu Usuki

  DOI：10.1002/ejoc.202000695

  日期：2020.9.14

  Pd/C‐mediated dearomatic hydrogenation under ambient conditions such as balloon pressure and room temperature can be a powerful tool for constructing alicyclic skeletons. Density functional theory calculations have been performed to confirm the mechanistic aspects and the utility of the established methodology has been demonstrated by donepezil synthesis.

  在诸如气球压力和室温等环境条件下，Pd / C介导的脱芳香族氢化反应可能是构建脂环族骨架的强大工具。已经进行了密度泛函理论计算以确认机理方面，并且通过多奈哌齐合成证明了所建立方法的实用性。
• [EN] TRNA SYNTHETASE INHIBITORS<br/>[FR] INHIBITEURS D'ARNT SYNTHÉTASE
  申请人：HARVARD COLLEGE

  公开号：WO2019140265A1

  公开（公告）日：2019-07-18

  Disclosed herein are secondary amine compounds that inhibit tRNA synthetase. The compounds of the invention are useful in inhibiting tRNA synthetase in Gram-negative bacteria and are useful in killing Gram-negative bacteria. The secondary amine compounds of the invention are also useful in the treatment of tuberculosis.

  本文披露了一种抑制tRNA合成酶的二级胺化合物。本发明的化合物在抑制革兰氏阴性细菌中的tRNA合成酶方面是有用的，并且在杀灭革兰氏阴性细菌方面也是有用的。本发明的二级胺化合物还在结核病的治疗中是有用的。
• One-pot synthesis of N-allylthioureas using supported reagents
  作者：Tadashi Aoyama、Sumiko Murata、Yasutaka Nagata、Toshio Takido、Mitsuo Kodomari

  DOI：10.1016/j.tetlet.2005.05.063

  日期：2005.7

  A simple and efficient method has been developed for the synthesis of N-allylthioureas from allylic bromides in one-pot by using a supported reagents system, KSCN/SiO2–RNH3OAc/Al2O3, in which allyl bromide reacts first with KSCN/SiO2 and the product, allyl isothiocyanate, reacts with RNH3OAc/Al2O3 to give the final product, N-allylthiourea, in good yield.

  通过使用支持的试剂系统KSCN / SiO 2 -RNH 3 OAc / Al 2 O 3，由一锅法从烯丙基溴中合成N-烯丙基硫脲的简单有效方法已被开发，其中烯丙基溴首先与KSCN / SiO 2和产物异硫氰酸烯丙酯与RNH 3 OAc / Al 2 O 3反应，以高收率得到最终产物N-烯丙基硫脲。
• Studies on the Chemistry and Reactivity of α-Substituted Ketones in Isonitrile-Based Multicomponent Reactions
  作者：Lijun Fan、Ashley M. Adams、Jason G. Polisar、Bruce Ganem

  DOI：10.1021/jo8019708

  日期：2008.12.19

  Using the Passerini and Ugi reactions as representative tests, the utility of several alpha-substituted ketones R-CO-CH(2)-X (X = sulfonyloxy, acyloxy, azido, halo, hydroxy, and sulfonyl) in isonitrile-based multicomponent reactions was explored. In a relative rate study (R = PhCH(2)CH(2)), each of the alpha-substituted ketones underwent Passerini condensation more rapidly than the parent ketone. Short

  使用Passerini和Ugi反应作为代表性测试，在基于异腈的多组分反应中使用几种α-取代的酮R-CO-CH（2）-X（X =磺酰氧基，酰氧基，叠氮基，卤素，羟基和磺酰基）被探索了。在相对速率研究中（R = PhCH（2）CH（2）），每个α-取代的酮比亲代酮经历Passerini缩合的速度更快。开发了短而高度收敛的恶唑啉，β-内酰胺，二-O-酰基甘油酰胺和其他分子框架的途径。
• Synthese und Reaktionsverhalten 4-phenylsubstituierter Isochinuclidine
  作者：Woldemar Schneider、Gottfried Krombholz

  DOI：10.1002/ardp.19803130603

  日期：——

  Verschiedene Synthesewege, die zu den 2‐Alkyl‐4‐phenylisochinuclidinen 14 und 15, zu den 3.4‐Diphenylisochinuclidinen 22–24 sowie zum 6‐Oxo‐4‐phenyl‐3‐isochinuclidon (43) führen, werden beschrieben. Die Struktur der bei der sauren Hydrolyse von 7‐Phenyl‐1.4‐dioxaspiro‐[4.5]decan‐7‐carbonsäureamid (36) entstehenden Produkte wird durch spektroskopische Methoden sowie durch Abbaureaktionen aufgeklärt

  描述了导致 2-烷基-4-苯基异奎宁环 14 和 15、3,4-二苯基异奎宁环 22-24 和 6-氧代-4-苯基-3-异奎宁酮 (43) 的各种合成路线。在 7-苯基-1.4-二氧杂螺-[4.5] 癸烷-7-甲酰胺 (36) 的酸水解过程中形成的产物的结构通过光谱方法和降解反应阐明。