N-trityl-γ-aminobutyric acid | 106518-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-trityl-γ-aminobutyric acid
• 英文别名: N-trityl-γ-amino-n.butyric acid；4-(tritylamino)butanoic acid；Trt-γ-aminobutyric acid；Trt-GABA-OH；4-Tritylaminobuttersaeure
• CAS: 106518-43-8
• 化学式: C₂₃H₂₃NO₂
• 分子量: 345.441
• InChiKey: XCOVSOODWWZDTF-UHFFFAOYSA-N

物化性质

• 沸点：
  516.5±38.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-trityl-γ-aminobutyric acid 在 劳森试剂 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 N-Benzyl-4-(trityl-amino)-thiobutyramide
  参考文献：
  名称：

  Efficient Syntheses of 5-Aminoalkyl-1H-tetrazoles and of Polyamines Incorporating Tetrazole Rings

  摘要：

  Linear N-omega-tritylated omega-amino th iobenzylam ides and N-alpha,N-omega-ditritylated polyamino mono- or bisthioamides were efficiently converted to the corresponding tetrazole derivatives upon treatment with azidotrimethylsilane under Mitsunobu reaction conditions.

  DOI：

  10.1021/ol0477069
• 作为产物：
  描述：

  三苯基氯甲烷 、 4-氨基丁酸 在 三甲基氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.75h， 以85%的产率得到N-trityl-γ-aminobutyric acid
  参考文献：
  名称：

  Synthesis and antioxidative/anti-inflammatory activity of novel fullerene–polyamine conjugates

  摘要：

  （E）-4-（富勒烯吡咯基）-3-甲基丁二烯酸和对应的丙二酸 succeedinimidyl 酯通过普拉托型修饰C-60易得，被广泛应用于富选择性N-酰化反应。由此获得的共轭体被评估为抗氧化及抗炎活性，同时测定它们的细胞毒性。本系列化合物显示出令人感兴趣的抗脂过氧化、抗氧酶活性及抗炎活性，且与苏丹类物质相比具有相近的细胞相容性。（C）2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.066

文献信息

• Simple syntheses of N-alkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A
  作者：Stratos Vassis、George Karigiannis、George Balayiannis、Maria Militsopoulou、Petros Mamos、George W Francis、Dionissios Papaioannou

  DOI：10.1016/s0040-4039(00)02308-x

  日期：2001.2

  trimethylsilyl γ-aminobutyrate and of N-trityl-γ-aminobutyric acid with methyl β-alaninate, respectively, followed by LiAlH4 reduction, produced N-monoalkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A. The applicability of this methodology on the solid phase was also demonstrated.

  通过琥珀酰亚胺基N-三苯甲基-β-丙氨酸酯与三甲基甲硅烷基γ-氨基丁酸酯的偶合可容易地将琥珀酰胺化N-三苯甲基-β-丙氨酰基-γ-氨基丁酸酯和N-三苯甲基-γ-氨基丁酰基-β-丙氨酸酰化各种胺用N-三苯甲基-γ-氨基丁酸和β-丙氨酸甲酯分别还原，然后用LiAlH 4还原，生成N-单烷基化亚精胺片段和精胺生物碱kukoamine A的类似物。该方法在固相上的适用性也是演示。
• Efficient Syntheses of Polyamines Bearing 1<i>H</i>-Tetrazol-5-yl Units on Their Amino Functions
  作者：Constantinos Athanassopoulos、Thomas Garnelis、George Magoulas、Dionissios Papaioannou

  DOI：10.1055/s-2006-942502

  日期：——

  Linear N-benzyl-N′-trityl-α,ω-diamines and N α, N ω-ditritylpolyamines were efficiently converted into the corresponding N-(1-benzyltetrazol-5-yl)-substituted derivatives upon treatment with benzyl isothiocyanate followed by reaction of the thus-obtained thioureas with azidotrimethylsilane under Mitsunobu reaction conditions.

  用异硫氰酸苄酯处理线性 N-苄基-N′-三苯甲基-δ,Ï-二胺和 Nδ,NÏ-二苯甲基多胺后，在三忍反应条件下，将得到的硫脲类化合物与叠氮三甲基硅烷反应，可有效地转化为相应的 N-（1-苄基四唑-5-基）取代衍生物。
• Simple total syntheses of N-substituted polyamine derivatives using N-tritylamino acids
  作者：Petros Mamos、Georgios Karigiannis、Costas Athanassopoulos、Sofia Bichta、Dimitrios Kalpaxis、Dionissios Papaioannou、Giovanni Sindona

  DOI：10.1016/0040-4039(95)01010-f

  日期：1995.7

  A general methodology for the total synthesis of N-alkyl- and acylpolyamine derivatives is described which is based on the coupling of suitable N-tritylamino acids with amines followed by lithium aluminium hydride reduction of the thus obtained amides.

  描述了总合成N-烷基-和酰基多胺衍生物的通用方法，该方法基于合适的N-三苯甲基氨基酸与胺的偶联，然后氢化铝锂还原由此获得的酰胺。
• Synthesis and antimicrobial activity of chloramphenicol–polyamine conjugates
  作者：George E. Magoulas、Ourania N. Kostopoulou、Thomas Garnelis、Constantinos M. Athanassopoulos、Georgia G. Kournoutou、Michael Leotsinidis、George P. Dinos、Dionissios Papaioannou、Dimitrios L. Kalpaxis

  DOI：10.1016/j.bmc.2015.04.069

  日期：2015.7

  A series of chloramphenicol (CAM) amides with polyamines (PAs), suitable for structure-activity relationship studies, were synthesized either by direct attachment of the PA chain on the 2-aminopropane- 1,3-diol backbone of CAM, previously oxidized selectively at its primary hydroxyl group, or from chloramphenicol base (CLB) through acylation with succinic or phthalic anhydride and finally coupling with a PA. Conjugates 4 and 5, in which the CLB moiety was attached on N4 and N1 positions, respectively, of the N-8,N-8-dibenzylated spermidine through the succinate linker, were the most potent antibacterial agents. Both conjugates were internalized into Escherichia coli cells by using the spermidine-preferential uptake system and caused decrease in protein and polyamine content of the cells. Noteworthy, conjugate 4 displayed comparable activity to CAM in MRSA or wild-type strains of Staphylococcus aureus and Escherichia coli, but superior activity in E. coli strains possessing ribosomal mutations or expressing the CAM acetyltransferase (cat) gene. Lead compounds, and in particular conjugate 4, have been therefore discovered during the course of the present work with clinical potential. (C) 2015 Elsevier Ltd. All rights reserved.
• Martelli, S., Farmaco, Edizione Scientifica, 1986, vol. 41, # 11, p. 881 - 891
  作者：Martelli, S.

  DOI：——

  日期：——