JOURNAL OF MOLECULAR STRUCTURE
·
2024
·
IF 4
Qianqian Xing,Xiaoliang Jia,Shiyu Jia,Yongqin Qi,Yuqi Wang,Yingxiong Wang,Xianglin Hou
The traditional synthesis methods of cyclopropyl methyl ketone (CPMK) have some disadvantages such as low yield, slow reaction rate and unclear catalytic mechanism. To solve these problems, a new strategy is developed to synthesize CPMK from 5‑chloro-2-pentanone (CPE) using 1,8-diazabicyclo[5.4.0]undec‑7-ene (DBU). Experiment results show that the yield of CPMK reached a maximum of 96.5 % in DBU at 40 °C for 30min. The mechanism study shows that the hydrogen bond between DBU and CPE is the key to drive the deprotonation and cyclization of CPE. The hydrogen bond is formed between the N atom on C = N of DBU and the α-H on the methylene group associated with the carbonyl group on CPE. The catalyst DBU is converted into [DBUH] + Cl − , which can be reclaimed and recycled completely. The density functional theory (DFT) calculation confirmed the existence of molecular hydrogen bonds and proved that the hydrogen bond driving force is the key to the reaction. The hydrogen bond driven mechanism provides a new idea for the basic research of cyclization reaction.
研究领域:
有机化学
·
催化反应
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
·
2020
·
IF 4.335
Lin Chen,Jin He
A novel Michael/alkylation cascade reaction of N-unprotected 3-bromooxindoles with α,β-unsaturated acyl phosphonates using DABCO as a robust catalyst followed by the derivatization of the acyl phosphonate intermediates in situ has been developed. This scenario enables rapid access to a diverse set of highly functionalized spirocyclopropyl oxindoles in moderate yields with good to excellent diastereoselectivities, which are analogues of a high active non-nucleoside reverse transcriptase inhibitor against HIV-1. The synthetic potential of this tactic has been highlighted by a gram-scale reaction and Suzuki cross-coupling reactions of the product. Moreover, the reaction mechanism has been tentatively elucidated by control experiments and dynamic high-resolution mass spectrometry studies, which indicates that the Michael/alkylation cascade reaction involves DABCO-derived α-substituted ammonium ylides.
研究领域:
有机化学
·
药物化学
·
抗病毒研究
✓ 已验证
DOI
PubMed
高影响因子
CHEMISTRY & BIODIVERSITY
·
2023
·Vol. 20
·期 5
·e202300105
·
IF 2.9
Wen-Bo Xu,Yu-Qing Meng,Jingxin Sun,Yu-Xuan Yang,Wan-Xin Li,Man-Yu Wang,Ming-Guan Piao,Siqi Li,Jishan Quan,Cheng-Hua Jin
A series of 2-cyclopropyl-5-(5-(6-methylpyridin-2-yl)-2-substituted-1 H -imidazol-4-yl)-6-phenylimidazo[2,1- b ][1,3,4]thiadiazoles ( 15a – t and 16a – f ) were synthesized and their antibacterial activities were evaluated. More than half of the compounds showed moderate or strong antibacterial activity. Among them, compounds 15t (MIC=1–2 μg/mL) and 16d (MIC=0.5 μg/mL) showed the strongest antibacterial activities. Notably, compound 16d did not exhibit cytotoxicity in HepG2 cells and did not show hemolysis like the positive control compound Gatifloxacin. The results suggest that compound 16d should be further investigated as a candidate antibacterial agent. Graphical
研究领域:
药物化学
·
微生物学
·
药理学
✓ 已验证
DOI
PubMed
高影响因子
Polymer Chemistry
·
2016
·Vol. 7
·期 23
·3913-3922
·
IF 5.687
Fangfang Yu,Liwei Cao,Zhaohui Meng,Naibo Lin,Xiang Yang Liu
A study on the cross-linking of fluorinated acrylate and siloxane waterborne polyurethanes was carried out in order to produce a material with improved waterproof property. Trimethylolpropane-tris-(β-N-aziridinyl) propionate was employed as a simple, fast curing and low cost crosslinking agent. It follows that the acquired polyurethane film had the lowest water absorption and highest water contact angles so far among this series of compounds, and has better mechanical/thermal properties once the fluoride acrylic monomer content reaches 8 wt% and polyether modified polydimethylsiloxane content is 10 wt%. Once the crosslinked structure is acquired, the overall performance of the polyurethane films are enhanced, i.e. the water absorption decreases to 3.48% and n-heptane swelling decreases to 1.02%, the hardness reaches 6H and the tensile strength also rises to 33.2 MPa. Such eco-friendly crosslinked polyurethane films with outstanding waterproof property can find various applications in corrosion protection and optoelectronic devices.
研究领域:
材料科学
·
高分子化学
·
表面化学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
·
2023
·
IF 3.6
Ming Huang,Changsheng Zhou,Ke-Fang Yang,Ze Li,Guo-Qiao Lai,Pinglu Zhang
An effective (NHC)AgCl catalysis was developed in the hydroborylation of cyclopropenes with B2pin2, delivering a variety of cyclopylboronates in a stereoselective manner, which could be easily transformed for the construction of versatile cyclopropanes. This protocol works effectively under mild reaction conditions in an open-air atmosphere, and it was easy to apply on a gram scale. This novel method in detail was also explored by control experiments, providing a number of key insights. The kinetic process followed by 1H NMR indicated that the reaction was finished in 15 min. Furthermore, the mechanism of silver(I)-catalyzed hydroborylation of cyclopropenes was proposed, with the protonation by methanol as the rate-determining step.
研究领域:
有机化学
·
催化
·
合成化学
✓ 已验证
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）