Co-reporter:Haifeng Huang;Ying Li;Renming Pan;Xiangyang Lin
New Journal of Chemistry (1998-Present) 2017 vol. 41(Issue 15) pp:7697-7704
Publication Date(Web):2017/07/24
DOI:10.1039/C7NJ01417A
In order to develop energetic materials with better comprehensive properties, energetic salts based on bifunctionalized furazan with nitramino and dinitromethyl group were synthesized and fully characterized by multinuclear NMR (1H, 13C or 15N), IR spectroscopy and elemental analysis. Ammonium (1b), hydroxylammonium (2b) and aminoguanidinium salts (5b) were further confirmed by single-crystal X-ray diffraction. In addition, their decomposition temperatures, impact sensitivities and friction sensitivities were determined. Among the salts, dihydroxylammonium DNMNAF (2b) showed the best comprehensive properties (2b: d = 1.930 g cm−3; Td = 175 °C; P = 43.0 GPa; vD = 9646 m s−1; IS = 8 J; FS = 64 N; OB = −5.3%), which makes it a promising high-performance energetic material.
Co-reporter:Haifeng Huang, Yameng Shi, Ying Li, Yanfang Liu and Jun Yang
RSC Advances 2016 vol. 6(Issue 69) pp:64568-64574
Publication Date(Web):17 Jun 2016
DOI:10.1039/C6RA12109H
In order to develop new energetic materials with high energy and low sensitivity, a series of nitrogen-rich energetic salts based on 3-nitramino-4-tetrazolefurazan were conveniently synthesized through nitration, neutralization and metathesis reaction. All energetic salts were fully characterized by NMR (1H, 13C), IR and elemental analysis. Furthermore, ammonium salt (2) was confirmed by 15N NMR and hydroxylammonium salt (5) was confirmed by single-crystal X-ray diffraction. Salt 5 crystallized in triclinic space group P with four hydroxylammonium cations and two NATF anions per unit cell at a density of 1.815 g cm−3. The densities of the salts are in the range of 1.621 (6) to 1.815 g cm−3 (5). Due to the two nitrogen-rich cations in the salts, they show high positive enthalpies of formation falling between 299.2 kJ mol−1 (2) and 1040.6 kJ mol−1 (9). All the salts show good thermal stabilities with the decomposition temperatures ranging from 203 °C (4) to 284 °C (6). The impact sensitivities of the energetic salts lie between 5 J (2 and 5) and >40 J (6, 7, 8) and their friction sensitivities range from 108 N (4) to >360 N (6). Their detonation performances were calculated according to Kamlet–Jacobs equations. The detonation pressures of the synthesized energetic salts were found to be in the range of 21.1 GPa (6) to 34.7 GPa (5) and their detonation velocities are between 7117 m s−1 (6) and 8826 m s−1 (5).
Co-reporter:Ying Li, Haifeng Huang, Xiangyang Lin, Renming Pan and Jun Yang
RSC Advances 2016 vol. 6(Issue 59) pp:54310-54317
Publication Date(Web):19 May 2016
DOI:10.1039/C6RA10756G
A new class of energetic salts containing an oxygen-rich anion—the 2,2,2-trinitroethyl nitrocarbamate anion were synthesized and fully characterized by NMR (1H and 13C), IR spectroscopy and elemental analysis. Furthermore, the crystal structures of ammonium salt (1), 4-amino-1,2,4-triazolium salt (4) and 3-amino-1,2,4-triazolium salt (5) were determined by single-crystal X-ray diffraction. The differential scanning calorimetry (DSC) results showed that the decomposition temperatures of these salts were between 121.1 °C (1) and 137.8 °C (2). The densities of these salts lie in the range of 1.753 (1) to 1.827 (4) g cm−3. Their impact sensitivities and friction sensitivities were measured to be in the range of 1–20 J and 14–36 N, respectively. All the salts exhibited promising detonation performances (detonation pressure: 29.4 to 33.1 GPa; detonation velocity: 8213 to 8596 m s−1), which were comparable to those of RDX.
Co-reporter:Lumin Zhang, Lili Zhu, Jun Yang, Jisheng Luo, and Ran Hong
The Journal of Organic Chemistry 2016 Volume 81(Issue 9) pp:3890-3900
Publication Date(Web):April 1, 2016
DOI:10.1021/acs.joc.6b00068
An Oppolzer’s sultam-based highly stereoselective α-hydroxylation of amides was developed to deliver the desired products in good yield and excellent diastereoselectivity (>20/1). The generally crystalline products and the recyclability of the chiral auxiliary illustrate the practicability and scalability of the current approach.
Co-reporter:Dr. Haifeng Huang;Yameng Shi;Yanfang Liu ;Dr. Jun Yang
Chemistry – An Asian Journal 2016 Volume 11( Issue 11) pp:1688-1696
Publication Date(Web):
DOI:10.1002/asia.201600026
Abstract
3,4-Diaminofurazan was conveniently converted into energetic salts of 3,4-dinitraminofurazan that were paired with nitrogen-rich cations in fewer than three steps. Seven energetic salts were prepared and fully characterized by multinuclear (1H, 13C) NMR and IR spectroscopy, differential scanning calorimetry (DSC), and elemental analysis. In addition, the structures of the ammonium salt (2), hydrazinium salt (4), hydroxylammonium salt (5), aminoguanidinium salt (7), diaminoguanidinium salt (8) and triaminoguanidinium salt of 3,4-dinitraminofurazan (9) were further confirmed by single-crystal X-ray diffraction. The densities of these salts were between 1.673 (8) and 1.791 g cm−3 (5), whilst their oxygen balances were between −48.20 % (9) and −6.25 % (5). These salts showed high thermal stabilities, with decomposition temperatures between 179 (5) and 283 °C (6). Their sensitivities towards impact and friction were measured by BAM equipment to be between <1 J (9) and >40 J (6–8) and 64 N (9) and >360 N (6), respectively. The detonation performance of these compounds, which was calculated by using the EXPLO5 program, revealed detonation pressures of between 28.0 (6) and 40.5 GPa (5) and detonation velocities of between 8404 (6) and 9407 m s−1 (5).
Co-reporter:Yun Cheng;Wen-hui Ding;Qin Long;Min Zhao;Xiao-qiang Li
Journal of Labelled Compounds and Radiopharmaceuticals 2015 Volume 58( Issue 9) pp:355-360
Publication Date(Web):
DOI:10.1002/jlcr.3311
Conventional synthetic procedures of strigolactones (SLs) involve the independent synthesis of ring ABC and ring D, followed by a coupling of the two fragments. Here we prepared three kinds of stable, isotopically labelled D-ring analogues productively using a facile protocol. Then, a coupling of the D-rings to ring ABC produced three isotope-labelled SL derivatives. Moreover, (+)-D3-2′-epi-1A and (−)-ent-D3-2′-epi-1A with high enantiomeric purity were obtained via chiral resolution.
Co-reporter:Xiaohong Sun, Yue Ouyang, Jinfang Chu, Jing Yan, Yan Yu, Xiaoqiang Li, Jun Yang, Cunyu Yan
Journal of Chromatography A 2014 Volume 1338() pp:67-76
Publication Date(Web):18 April 2014
DOI:10.1016/j.chroma.2014.02.056
•Developed stable isotope–coded labeling derivatization reagents.•High throughput sample handling process with in advance labeling strategy.•Relative quantification of multiple plant hormones in microgram samples.A sensitive and reliable in-advance stable isotope labeling strategy was developed for simultaneous relative quantification of 8 acidic plant hormones in sub-milligram amount of plant materials. Bromocholine bromide (BETA) and its deuterated counterpart D9-BETA were used to in-advance derivatize control and sample extracts individually, which were then combined and subjected to solid-phase extraction (SPE) purification followed by UPLC–MS/MS analysis. Relative quantification of target compounds was obtained by calculation of the peak area ratios of BETA/D9-BETA labeled plant hormones. The in-advance stable isotope labeling strategy realized internal standard-based relative quantification of multiple kinds of plant hormones independent of availability of internal standard of every analyte with enhanced sensitivity of 1–3 orders of magnitude. Meanwhile, the in-advance labeling contributes to higher sample throughput and more reliability. The method was successfully applied to determine 8 plant hormones in 0.8 mg DW (dry weight) of seedlings and 4 plant hormones from single seed of Arabidopsis thaliana. The results show the potential of the method in relative quantification of multiple plant hormones in tiny plant tissues or organs, which will advance the knowledge of the crosstalk mechanism of plant hormones.
Co-reporter:Tao Yu, Xin-Yan Wu, Jun Yang
Tetrahedron Letters 2014 Volume 55(Issue 30) pp:4071-4074
Publication Date(Web):23 July 2014
DOI:10.1016/j.tetlet.2014.05.106
An efficient one-step method has been developed to construct furans via a Suzuki–Miyaura cross-coupling reaction of 1,2-oxaborol-2(5H)-ols with carboxylic anhydrides. In the presence of Pd(OAc)2/PCy3, the multi-substituted alkenylboron compounds could couple with anhydrides to obtain furans in moderate-to-good yields. The addition of bases promoted the coupling reaction, and the plausible reaction mechanism was proposed.
Co-reporter:Chun-Xiao Cui, Hui Li, Xian-Jin Yang, Jun Yang, and Xiao-Qiang Li
Organic Letters 2013 Volume 15(Issue 23) pp:5944-5947
Publication Date(Web):November 14, 2013
DOI:10.1021/ol402782f
A series of functionalized 2,5-dihydrofurans were efficiently synthesized via an amine-promoted Petasis borono–Mannich reaction of 4-substituted 1,2-oxaborol-2(5H)-ols with salicylaldehydes in high yields. The process, which combines a boronic acid-based Mannich reaction and a highly efficient intramolecular SN2 cyclization, provides a one-step and efficient route toward 2,5-dihydrofurans from simple and stable starting materials.
Co-reporter:Tao Yu;Xinyan Wu
Chinese Journal of Chemistry 2012 Volume 30( Issue 12) pp:2798-2804
Publication Date(Web):
DOI:10.1002/cjoc.201201122
Abstract
Z and E configuration 4-aryl-but-2-en-1-ols were isolated from several terrestrial plants, and (Z)-4-aryl-but-2en-1-ols were found to have choleretic activity. Strategies have been reported to synthesize (E)-4-aryl-but-2-en-1ols with high selectivity. However, there is no method to obtain (Z)-4-aryl-but-2-en-1-ols with high selectivity now. We developed a Suzuki-Miyaura cross-coupling reaction of 1,2-oxaborol-2(5H)-ols with benzyl bromides to synthesize (Z)-4-aryl-but-2-en-1-ols, the products were obtained in up to 94% isolated yield.
Co-reporter:Haifeng Huang, Yameng Shi, Yanfang Liu and Jun Yang
Dalton Transactions 2016 - vol. 45(Issue 39) pp:NaN15389-15389
Publication Date(Web):2016/08/19
DOI:10.1039/C6DT02993K
The 1,2,4,5-dioxadiazine ring was introduced as a bridge connecting two nitraminofurazan moieties to form energetic salts based on 3,6-bis(4-nitramino-1,2,5-oxadiazol-3-yl)-1,2,4,5-dioxadiazine (H2BNOD). Eight nitrogen-rich energetic salts based on the BNOD anion were synthesized and fully characterized by NMR (1H NMR, 13C NMR, 15N NMR), IR and elemental analysis. Furthermore, H2BNOF (5), ammonium (6), hydroxylammonium (8) and 4-amino-1,2,4-triazolium salts (13) were analyzed by single-crystal X-ray diffraction. The densities of the salts were in the range of 1.730 (13) to 1.914 g cm−3 (8). These salts showed much better thermal stabilities and mechanical sensitivities than their precursor, H2BNOD. The decomposition temperatures of the salts ranged from 114 (6) to 197 °C (9). The impact sensitivities of the energetic salts were between 1.5 and 4.5 J, and their friction sensitivities ranged from 53 to >144 N. Their detonation pressures and detonation velocities were calculated to be in the range of 26.3 (12) to 38.1 GPa (8), and 7754 (12) to 9095 m s−1 (8), respectively.
Co-reporter:Ying Li, Haifeng Huang, Xiangyang Lin, Renming Pan and Jun Yang
Dalton Transactions 2016 - vol. 45(Issue 39) pp:NaN15650-15650
Publication Date(Web):2016/08/31
DOI:10.1039/C6DT03239G
A unique and facile method was developed to synthesize a new class of energetic salts based on 2-amino-1,1,5,5-tetranitro-4-oxo-3-aza-pentene. All the salts were fully characterized by NMR (1H and 13C), IR spectroscopy and elemental analysis. Furthermore, the crystal structure of the guanidinium salt (5) was determined by single-crystal X-ray diffraction. The differential scanning calorimetry (DSC) results showed that the decomposition temperatures of these salts were between 126.2 °C (10) and 148.8 °C (9). The densities of these salts lie in the range of 1.745 (8) to 1.880 (4) g cm−3. Their impact sensitivities and friction sensitivities were measured to be in the range of 1–16 J and 48–84 N, respectively. All the salts exhibited promising detonation performances (detonation pressure: 28.6 to 34.3 GPa; detonation velocity: 8037 to 8674 m s−1), and the detonation performances of salt 4 were comparable to those of RDX.
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![1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)pent-4-en-1-one](http://img.cochemist.com/ccimg/127400/127392-82-9_b.png)
![(2s,3s)-4-[(e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic Acid](http://img.cochemist.com/ccimg/28900/28831-65-4.png)
![(2s,3s)-4-[(e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic Acid](http://img.cochemist.com/ccimg/28900/28831-65-4_b.png)
