tert butyl (4 aminobutyl)(3-aminopropyl)carbamate | 182576-24-5

• 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: tert butyl (4 aminobutyl)(3-aminopropyl)carbamate
• 英文别名: H2N(CH2)3N(Boc)(CH2)4NH2；H2N(CH2)3N(tert-butoxycarbonyl)(CH2)4NH2；N⁴-(tert-butoxycarbonyl)-spermidine；tert-butyl N-(4-aminobutyl)-N-(3-aminopropyl)carbamate
• CAS: 182576-24-5
• 化学式: C₁₂H₂₇N₃O₂
• 分子量: 245.365
• InChiKey: LXFKQBNEHNLMRB-UHFFFAOYSA-N

物化性质

• 沸点：
  353.8±35.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert butyl (4 aminobutyl)(3-aminopropyl)carbamate 在 potassium carbonate 、 caesium carbonate 、 苯硫酚 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 31.0h， 生成 3,12-Bis-(3-bromo-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1(18),14,16-triene
  参考文献：
  名称：

  Solution Phase Combinatorial Chemistry. Discovery of Novel Polyazapyridinophanes with Potent Antibacterial Activity by a Solution Phase Simultaneous Addition of Functionalities Approach

  摘要：

  Chemical modification of pre-formed asymmetric polyazaphane scaffolds by simultaneous addition of Functionality (letters) in solution has been developed for the preparation of tertiary nitrogen-based combinatorial chemistry libraries. This approach has some significant advantages over the more commonly employed solid phase bead splitting/resction/mixing procedures for the preparation of libraries. Three novel, asymmetric polyazaphanes 32, 33, and 37 have been synthesized in high yields by an efficient cyclization of 2,6-bis(bronzomethyl)pyridine (31) with new orthogonally protected triamines 29, 30, and 35, respectively. Selective deprotection of 32, 33, and 37 provided mono-t-Boc-protected scaffolds 1-3 suitable for solution phase, simultaneous addition of functionalities. Model studies of small libraries of scaffold 2 using CZE analyses indicated that simultaneous addition of 10 benzylic bromide alkylating functionalities would result in libraries containing approximately equimolar amounts of all possible compounds. Sixteen purified tertiary amine libraries 4-19 (total complexity of 1600 compounds) were generated by this procedure from scaffold 2. A ''fix-last'' combinatorial method was devised to minimize chemical reactions. Several first-round sublibraries of scaffold 2, containing a mixture of 100 compounds, exhibited potent antimicrobial activities. Twenty single compounds 63-82 with uniform functionalities at the combinatorialized sites were synthesized. Some of these pure compounds were more active, while others were less active, compared with the parent mixtures 5 and 10.

  DOI：

  10.1021/ja964153r
• 作为产物：
  描述：

  亚精胺 在 sodium hydroxide 、 水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 54.0h， 生成 tert butyl (4 aminobutyl)(3-aminopropyl)carbamate
  参考文献：
  名称：

  WO2006/136460

  摘要：

  公开号：

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。
• Solution phase combinatorial chemistry I. synthesis of polyazacyclophane scaffolds and tertiary amine libraries
  作者：Haoyun An、P.Dan Cook

  DOI：10.1016/0040-4039(96)01627-9

  日期：1996.9

  Three novel unsymmetrical polyazacyclophane scaffolds 1–3 were efficiently synthesized in high yields by a new cyclization method followed by selective deprotection. Scaffold 2 was combinatorialized by solution phase simultaneous addition of functionalities to provide 16 pure tertiary amine libraries (total 1600 compounds).

  通过一种新的环化方法，然后进行选择性脱保护，可以高产率高效地合成了三种新型的非对称多氮杂氮杂环庚烷骨架1-3。通过溶液相的同时添加功能来组合支架2，以提供16个纯叔胺库（总共1600种化合物）。
• Scocycamides, a Pair of Macrocyclic Dicaffeoylspermidines with Butyrylcholinesterase Inhibition and Antioxidation Activity from the Roots of <i>Scopolia tangutica</i>
  作者：Ji-Xia Wang、Yao-Peng Zhao、Na-Na Du、Yang Han、Hao Li、Rong Wang、Yang Xu、Yan-Fang Liu、Xin-Miao Liang

  DOI：10.1021/acs.orglett.0c02838

  日期：2020.11.6

  A pair of new macrocyclic spermidine alkaloids, (+)-(S)-scocycamide and (−)-(R)-scocycamide, were isolated from the roots of Scopolia tangutica. Their structures were established by extensive spectroscopic data, electronic circular dichroism analyses, and chemical synthesis. They featured a unique 6/18 fused bicyclic framework with spermidine and catechol units, representing a new subtype of natural

  一对新的大环亚精胺生物碱，(+)-( S )-scocycamide 和(-)-( R )-scocycamide，是从Scopolia tangutica的根中分离出来的。它们的结构是通过广泛的光谱数据、电子圆二色性分析和化学合成建立的。它们具有独特的 6/18 稠合双环骨架，具有亚精胺和儿茶酚单元，代表了天然亚精胺生物碱的新亚型。还提出了一种合理的生物合成途径。它们抑制丁酰胆碱酯酶并表现出抗氧化能力，表明它们是对抗阿尔茨海默病和氧化的有益成分。
• Chemoselective Protection of Glutathione in the Preparation of Bioconjugates: The Case of Trypanothione Disulfide
  作者：Antonia I. Antoniou、Dionissia A. Pepe、Donatella Aiello、Carlo Siciliano、Constantinos M. Athanassopoulos

  DOI：10.1021/acs.joc.6b00300

  日期：2016.5.20

  involving the chemical modification of the commercially available glutathione (GSH). The synthetic value of this building block in the facile preparation of GSH bioconjugates in a satisfying overall yield was exemplified by the case of trypanothione disulfide (TS2), a GSH-spermidine bioconjugate, involved in the antioxidative stress protection system of parasitic protozoa, such as trypanosoma and leishmania

  描述了化学选择保护的N，S-二三苯甲基谷胱甘肽单甲酯的新颖合成途径，涉及对可商购的谷胱甘肽（GSH）进行化学修饰。该结构单元在以令人满意的总收率方便地制备GSH生物共轭物中的合成价值，以GSH-亚精胺生物共轭双硫醚（TS 2）参与寄生原生动物的抗氧化应激保护系统为例。作为锥虫和利什曼原虫的寄生虫。
• Synthesis of 13C-dilabeled 4-coumaroylspermidines
  作者：Hervé Geneste、Manfred Hesse

  DOI：10.1016/s0040-4020(98)01014-x

  日期：1998.12

  Five C-13-dilabeled constitution isomers of 4-coumaroylspermidines were prepared in nine to eleven steps: N-1,4-di[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (13b), N-1-[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (17b), N-1,8-di[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (20b), N-4-[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (24b) and N-1,4,8-tri[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (26). The two C-13-atoms were subsequently introduced using labeled potassium cyanide. The synthesis proceeds through stepwise construction of the polyamine backbone including protection and deprotection steps of the amino functions. Based on H-1-H-1 NOE interactions, the preliminary study of their binding reveals that 20b binds to tRNA in the. same way as spermidine does, whereas 24b and 26 do not-show any NOE effects with the tRNA protons. (C) 1998 Elsevier Science Ltd. All rights reserved.