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Short-RInChIKey=SA-FUHFF-UHFFFADPSC-WUGJXCOMZV-UHFFFADPSC-NUHFF-NODPP-NUHFF-ZZZ
No full text(E)-3-(3,3-Diisopropyltriaz-1-en-1-yl)-5-methyl-1H-pyrazole (500 mg, 2.39 mmol, 1.00 equiv) was dissolved in DMSO (25.0 mL) and cesium carbonate (934 mg, 2.87 mmol, 1.20 equiv) was added. The reaction mixture was cooled to 0 °C and bromomethylbenzene (817 mg, 568 μL, 4.78 mmol, 2.00 equiv) was slowly added. After the addition, the reaction mixture was slowly warmed to 21 °C and stirred for 16 hours at this temperature. For work up ice-water was added to the reaction mixture. The aqueous phase was extracted three-times with ethyl acetate and the combined organic phase was washed with water and brine, dried over Na2SO4 and filtered
infrared absorption spectroscopy (IR) ()
No full textdataset for infrared absorption spectroscopy (IR)
IR (ATR, ṽ) = 2976 (w), 2962 (w), 2928 (w), 2871 (vw), 1605 (w), 1594 (m), 1543 (w), 1514 (s), 1499 (s), 1462 (w), 1431 (w), 1409 (s), 1392 (vs), 1378 (vs), 1358 (s), 1330 (vs), 1302 (s), 1285 (vs), 1245 (s), 1213 (s), 1170 (w), 1157 (m), 1128 (vs), 1109 (vs), 1096 (s), 1052 (w), 1041 (w), 1011 (vs), 973 (m), 908 (w), 882 (w), 854 (vs), 843 (vs), 820 (m), 781 (vs), 752 (m), 745 (m), 717 (w), 690 (m), 681 (w), 664 (w), 650 (w), 635 (w), 611 (w), 550 (m), 526 (w), 506 (m), 492 (s), 446 (w), 435 (w), 414 (w), 387 (w) cm–1
distortionless enhancement with polarization transfer (DEPT) ()
No full textdataset for distortionless enhancement with polarization transfer (DEPT
distortionless enhancement with polarization transfer (DEPT) ()
No full textdataset for distortionless enhancement with polarization transfer (DEPT
1H nuclear magnetic resonance spectroscopy (1H NMR) ()
No full textdataset for 1H nuclear magnetic resonance spectroscopy (1H NMR)
1H NMR (400 MHz, ppm) δ = 7.64 (s, 4H), 6.23 (s, 1H), 5.37 (quint, J = 6.4 Hz, 1H), 3.92 (quint, J = 6.5 Hz, 1H), 2.38 (s, 3H), 1.30 (d, J = 6.2 Hz, 6H), 1.15 (d, J = 6.5 Hz, 6H)
distortionless enhancement with polarization transfer (DEPT) ()
No full textdataset for distortionless enhancement with polarization transfer (DEPT
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-CYWVRVVKPF-UHFFFADPSC-NUHFF-NGYHM-NUHFF-ZZZ
No full textThe information given below was retrieved and reworked from the publication: A Unified Strategy Trageting the Thiodiketopiperazine Mycotoxins Exserohilone, Gliotoxin, the Epicoccins, the Epicorazines, Rostratin A and Aranotin by Ulrike Gross, Martin Nieger and Stefan Bräse.https://doi.org/10.1002/chem.201001169To a solution of ditert-butyl (2S,3aR,6S,6aS)-4-oxo-6-prop-2-enyl-3,3a,6,6a-tetrahydro-2H-furo[3,4-b]pyrrole-1,2-dicarboxylate (795 mg, 2.16 mmol) in toluene (58 ml) vinyloxytrimethylsilane (980 μl, 750 mg, 6.5 mmol, 3.0 eq.) was added. Then Grubbs II catalyst (50 mg, 58 μmol, 2.7 mol-%) was added in one portion and the reaction mixture was refluxed for 16 h. All volatiles were evaporated in vacuo and the crude product was purified by flash-chromatography (cyclohexane:ethyl acetate 5:1) to afford (2S,3aR,6S,6aS)-4-keto-6-[(E)-prop-1-enyl]-3,3a,6,6a-tetrahydro-2H-furo[3,4-b]pyrrole-1,2-dicarboxylic acid ditert-butyl ester (695 mg, 88%) as a white solid. Starting material di-tert-butyl (2S,3aR,6S,6aS)-4-oxo-6-prop-2-enyl-3,3a,6,6a-tetrahydro-2H-furo[3,4-b]pyrrole-1,2-dicarboxylate (92 mg, 11%) could be recovered.Analysis of the target compound: Rf = 0.39 (cyclohexane:ethyl acetate 2:1). – m.p.: 162 – 163 °C. – [α]D20 = –172.5 (c = 0.28, CHCl3). – 1H NMR (400 MHz, CDCl3, 2 rotamers 0.60:0.40): δ/ppm = 1.40, 1.43, 1.44, 1.45 (4 × s, 18H), 1.70 (dm, J = 6.6, 1.8H), 1.74 (dm, J = 6.9, 1.2H), 2.32 – 2.40 (m, 2H), 3.27 (ddd, J = 9.7, J = 9.7, J = 9.7 Hz, 0.60H), 3.33 (ddd, J = 9.7, J = 9.7, J = 9.7 Hz, 0.40H), 4.30 (dd, J = 5.0, J = 5.0 Hz, 0.60H), 4.36 (dd, J = 7.5, J = 3.2 Hz, 0.40H), 4.85 (dd, J = 9.5, J = 7.5 Hz, 0.40H), 4.92 (dd, J = 9.6, J = 7.6 Hz, 0.60H), 5.01 (dd, J = 7.5, J = 7.5 Hz, 0.40H), 5.13 (dd, J = 7.2, J = 7.2 Hz, 0.60H), 5.35 – 5.43 (m, 1H), 5.82 (dqd, J = 13.2, J = 6.6, J = 1.0 Hz, 1H). – 13C NMR (100 MHz, CDCl3, 2 rotamers 0.60:0.40): δ/ppm = 17.9, 17.9 (+); 27.9, 27.9, 28.1, 28.2 (2 × +); 32.0, 33.1 (–); 41.8, 43.0 (+); 61.2, 61.6 (+); 62.3, 62.5 (+); 80.8, 80.9, 82.0, 82.1 (2 × Cquart); 82.9, 83.4 (+); 125.0, 125.3 (+); 130.7, 132.0 (+); 153.4, 153.5 (Cquart); 170.5, 170.6 (Cquart); 175.1, 175.3 (Cquart).– IR (KBr): ṽ/cm-1 = 2974 (m), 2949 (m), 1761 (m), 1734 (m), 1692 (m), 1476 (w), 1455 (w), 1392 (m), 1367 (m), 1316 (m), 1295 (m), 1258 (m), 1193 (m), 1143 (m), 1074 (m), 1006 (m), 990 (m). – MS (FAB, matrix: 3-NBA), m/z (%): 368.2 (22) [MH+], 312 (28) [MH+ – CH2C(CH3)2], 256 (100) [MH+ – 2 × CH2C(CH3)2], 212 (42) [MH+ – CH2C(CH3)2 – CO2tBu]. – HRMS (FAB, matrix: 3-NBA) C19H30NO6: calcd. 368.2073; found 368.2071. – Elemental analysis: C19H29NO6 (367): calcd. C 62.11, H 7.96, N 3.81; found C 61.87, H 7.74, N 3.68
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-SMYOIWBJMS-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ
No full textThe information given below was retrieved and reworked from the publication: Use of the Chiral Pool - Practial Asymmetric Organocatalytic Strecker Reaction with Quinine by Rüdiger Reingruber, Thomas Baumann, Stefan Dahmen and Stefan Bräse.https://doi.org/10.1002/adsc.200800798The reaction was conducted according to the general procedure for Strecker reaction of N-carbamyl-α-(phenylsulfonyl)amines: A 0.5 M solution of the N-carbamyl-α-(phenylsulfonyl)amine (500 µmol, 1.00 equiv.) and quinine (5 mol%) in CH2Cl2 (1.0 mL) was cooled to –10 °C under argon. At this temperature KCN (1.00 mmol, 2.00 equiv.) was added and the reaction mixture was stirred vigorously for 24 h at –10 °C. After completion, the mixture was quenched with sat. aq. NaHCO3 (1.00 mL), extracted with CH2Cl2 (2 × 5 mL), dried over MgSO4 and concentrated in vacuo. The resulting residue was further purified by column chromatography to give the pure title compounds. The enantiomeric excess (ee) of each product was determined by HPLC analysis on chiral stationary phase.Analysis of the target compound: The title compound could be obtained in 95% yield as a white solid (mp 88–90 °C); Rf = 0.61 (silica, ethyl acetate/cyclohexane, 1:1); 1H NMR (400 MHz, CDCl3): δ = 7.58 (dd, J = 7.6, 1.5 Hz, 1 H, Ar-H), 7.32 (dt, J = 7.2, 1.4 Hz, 1 H, Ar-H), 7.28 (dd, J = 7.3, 1.7 Hz, 1 H, Ar-H), 7.24 (d, J = 7.2 Hz, 1 H, Ar-H), 5.86 (d, J = 6.6 Hz, 1 H, NH), 4.97 (d, J = 5.3 Hz, 1 H, CH), 2.37 (s, 3 H, CH3), 1.47 (s, 9 H, tBu-H) ppm; 13C NMR (100 MHz, CDCl3): δ = 153.9, 136.2, 131.4, 129.8, 127.3, 126.8, 118.0 ppm; IR (KBr): v = 3341 (m), 3302 (m), 2982 (m), 2741 (w), 2242 (w), 1686 (s), 1509 (s), 1300 (m), 1166 (m), 1055 (m), 947 (w), 883 (m), 754 (m), 663 (m) cm–1; MS (70 eV, EI), m/z (%): 246 (1) [M+], 231 (2), 191 (13), 190 (100), 164 (13), 163 (14), 146 (10), 145 (14), 130 (33), 129 (62), 119 (13), 118 (15), 103 (16), 91 (14), 59 (16), 57 (51), 41 (8); HRMS (EI): calc. C14H18N2O2+ [M+]: 246.1368, found 246.1367
1H--13C heteronuclear multiple bond coherence (13C-1H HMBC) ((2,2-dimethylchromen-6-yl)methanol)
No full textdataset for 1H--13C heteronuclear multiple bond coherence (13C-1H HMBC
C51H42AgCl2CuN3P3
No full textThis is a physical chemical entity[CHEBI_24431] associated with a molecule[CHEBI_25367].
The molecule[CHEBI_25367] can be described by the following structural desciptors[cheminf_000085]:
InChI descriptor[cheminf_000113]: InChI=1S/3C17H14NP.Ag.2ClH.Cu/c3*1-3-9-15(10-4-1)19(16-11-5-2-6-12-16)17-13-7-8-14-18-17;;;;/h3*1-14H;;2*1H;/q;;;+1;;;+1/p-2, and canonical SMILES descriptor[cheminf_000007]: c1ccc(cc1)P(c1ccccn1)c1ccccc1.c1ccc(cc1)P(c1ccccn1)c1ccccc1.c1ccc(cc1)P(c1ccccn1)c1ccccc1.Cl[Cu].Cl[Ag], and by the IUPAC name[cheminf_000107]: .
The physical chemical entity[CHEBI_24431] has a component solvent[CHEBI_46787] which is described by the canonical SMILES descriptor[cheminf_000007]:
The physical chemical entity[CHEBI_24431] has the following Sample ID as registered in the research data repository chemotion (www.chemotion-repository.net, https://doi.org/10.25504/FAIRsharing.iagXcR): CRS-36044
The physical chemical entity[CHEBI_24431] can be described by the physical descriptors [CHEMINF_000025]:
Melting point descriptor[CHEMINF_000256]:
Boiling point descriptor[CHEMINF_000257]:
Refractive index descriptor[CHEMINF_000253]:
The physical chemical entity[CHEBI_24431] can be further described by the following assays[OBI:0000070][CHMO:0001133]:
CHMO:0000889 | proton-decoupled 31P nuclear magnetic resonance spectroscopy (31P{1H}-NMR)
CHMO:0000156 | X-ray diffraction (XRD)
CHMO:0000563 | fast-atom bombardment mass spectrometry (FABMS)
CHMO:0000595 | 13C nuclear magnetic resonance spectroscopy (13C NMR)
CHMO:0001146 | 1H--13C heteronuclear single quantum coherence (1H-13C HSQC)
CHMO:0000593 | 1H nuclear magnetic resonance spectroscopy (1H NMR)
The physical chemical entity[CHEBI_24431] was deposited to the Molecule Archive of the Karlsruhe Insitute of Technology (KIT) with the following Sample ID:
Used ontologies:
CHEBI - Chemical Entities of Biological Interest
CHEMINF - chemical information ontology (information entities about chemical entities)
CHMO - Chemical Methods Ontology
OBI - Ontology for Biomedical Investigation