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1H nuclear magnetic resonance spectroscopy (1H NMR) ()
No full textdataset for 1H nuclear magnetic resonance spectroscopy (1H NMR)
1H NMR (400 MHz, Chloroform-d [7.27 ppm], ppm) δ = 8.31–8.29 (m, 2H), 7.77 (d, J = 8.4 Hz, 2H), 6.33 (s, 1H), 5.46 (t, J = 6.2 Hz, 1H), 4.01 (t, J = 6.1 Hz, 1H), 2.49 (s, 3H), 1.38 (d, J = 6.1 Hz, 6H), 1.23 (d, J = 6.4 Hz, 6H)
mass spectrometry (MS) ()
No full textdataset for mass spectrometry (MS)
EI (m/z, 70 eV, 70 °C): 311 (13) [M+H]+, 310 (61) [M]+, 299 (26), 210 (53), 200 (11), 199 (82), 182 (12), 181 (20), 141 (59), 131 (26), 114 (10), 102 (12), 100 (52), 91 (100), 69 (57), 58 (58), 57 (12), 54 (10).HRMS (C17H22N6): Calcd 310.1906. Found 310.1904
distortionless enhancement with polarization transfer (DEPT) ()
No full textdataset for distortionless enhancement with polarization transfer (DEPT
heteronuclear multiple bond coherence (HMBC) ()
No full textdataset for heteronuclear multiple bond coherence (HMBC
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-HEQYPJIVZW-UHFFFADPSC-NUHFF-NVVLV-NUHFF-ZZZ
No full textIn a vial, 3-(1H-5-methylpyrazole) triazene resin (1.00 g, 695 μmol, 1.00 equiv) was suspended in DMSO (20.0 mL). Cesium carbonate (1.13 g, 3.48 mmol, 5.00 equiv) and 4-fluorobenzonitrile (337 mg, 2.78 mmol, 4.00 equiv) were added. The vial was closed and shaken at 120 °C for 3 days. The resin was washed with 3x acetone, 3x dist. water, 3x acetone, 3x THF, 3x MeOH, 3x DCM, 3x MeOH. The resin was then dried at high vacuum until constant weight was obtained
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-AFYWJZVKEA-UHFFFADPSC-NUHFF-NAKRX-NUHFF-ZZZ
No full textTo a -20 °C cold solution of 5-methyl-1H-pyrazol-3-amine (768 mg, 7.91 mmol, 5.00 equiv) in dry THF (9.00 mL) was added boron trifluoride etherate (1.68 g, 1.50 mL, 11.9 mmol, 7.50 equiv) under nitrogen. After 5 minutes, 3-methylbutyl nitrite (1.39 g, 1.59 mL, 11.9 mmol, 7.50 equiv) was added dropwise at -20 °C. The mixture was stirred for 2 hours at -20 °C and the precipitate was filtered (by glass tube with frit) and washed with cold ether. In a round bottom flask, benzylamine resin (2.00 g, 1.58 mmol, 1.00 equiv) was swollen in a mixture of THF (36.0 mL) and pyridine (4.00 mL) (9:1). The diazonium salt was then taken up in a little amount of acetonitrile and added slowly to the previously swollen benzylamine resin, which was cooled to -20 °C. The mixture was kept at -20 °C for 2 hours and manually swirled at regular intervals. The flask was then shaken at 21 °C for further 14 hours. The resin was washed with 3x acetone, 3x dist. water, 3x acetone, 3x THF, 3x MeOH, 3x DCM, 3x MeOH. The resin was dried at high vacuum until constant weight was obtained
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-MDKAQTASOM-UHFFFADPSC-NUHFF-NUVXA-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.201001169A solution of (2S,4S,5S)-di-tert-butyl-4-(1-hydroxyallyl)-5-[(S)-1-(triethylsilyloxy)but-2-enyl]pyrrolidine-1,2-dicarboxylate (137 mg, 0.596 mmol) in dichloromethane (14 ml) was treated with Dess-Martin-periodinane (0.48 M in dichloromethane, 1.1 ml, 0.54 mmol, 2.0 eq.) at room temperature. The white suspension was stirred for 2 h at room temperature, whereupon a solution of Na2S2O3 (10% in water, 30 ml) was added. The mixture was extracted with ethyl acetate (4 × 30 ml) and the combined organic extracts were dried over Na2SO4. Then all volatiles were removed in vacuo and the crude product was purified by flash-chromatography (cyclohexane:ethyl acetate 20:1) to afford (2S,4S,5S)-di-tert-butyl-4-acryloyl-5-[(S)-1-(triethylsilyloxy)but-2-enyl)pyrrolidine-1,2-dicarboxylate (126 mg, 92%) as a colorless oil.Analysis of the target compound: Rf = 0.46 (cyclohexane:ethyl acetate 5:1). – [α]D20 = –19.5 (c = 0.54, CHCl3). – 1H NMR (400 MHz, CDCl3, 2 E/Z-isomers and their 2 rotamers): δ/ppm = 0.45 – 0.67 (m, 6H); 0.77 – 0.99 (m, 9H); 1.38, 1.40, 1.41, 1.43, 1.44, 1.45, 1.49, 1.50 (8 × s, 18H); 1.60 – 1.74 (m, 3H); 2.03 – 2.33 (m, 1H); 2.45 – 2.66 (m, 1H); 3.02 – 3.80 (m, 1H); 4.02 – 4.16 (m, 1H); 4.26 – 5.06 (m, 2H); 5.25 – 5.53 (m, 1H); 5.58 – 5.79 (m, 2H); 6.14 – 6.46 (m, 1H); 6.46 – 6.73 (m, 1H). – 13C NMR (100 MHz, CDCl3, 2 E/Z-isomers and their 2 rotamers): δ/ppm = 4.8, 4.8, 4.8 (–); 6.6, 6.8, 6.8 (+); 13.6, 17.9, 17.9 (+); 27.7, 27.8, 27.9, 28.2, 28.2, 28.2, 28.5 (2 × +); 28.5, 28.5, 28.8 (–);47.9, 48.9, 49.2 (+); 61.2, 61.6 (+); 64.1, 64.9 (+); 70.1, 70.3, 71.2 (+); 79.7, 80.4, 81.0 (2 × Cquart); 127.7, 128.1 (+); 128.5, 128.7 (–); 128.9, 129.2 (+); 133.8, 133.9, 133.9 (+); 153.7, 153.8 (Cquart); 170.9, 171.3, 171.3 (Cquart), 197.7, 197.9 (Cquart). – IR (Film auf KBr): ṽ/cm-1 = 2958 (m), 2878 (m), 1743 (m), 1703 (s), 1615 (w), 1455 (m), 1386 (s), 1232 (m), 1159 (s), 1124 (m), 1075 (m). – MS (FAB, matrix: 3-NBA), m/z (%): 510 (10) [MH+], 410 (6) [MH+– CH2C(CH3)3 – CO2], 398 (17) [MH+ – 2 × CH2C(CH3)2], 354 (30) [MH+ – CO2 – 2 × CH2C(CH3)2]. – HRMS (FAB, matrix: 3-NBA) C27H48NSiO6: calc. 510.3251; found 510.3253. – Elemental analysis: C27H47NSiO6 (509): calc. C 63.62, H 9.29, N 2.75; found C 63.81, H 8.90, N 3.07
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-JCOJMVSDOY-UHFFFADPSC-NUHFF-NCTRW-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.201001169A solution of (2S,3aS,4S,7S,7aS)-Di-tert-butyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate (19 mg, 40.5 μmol) in THF (1 ml) was treated with PPh3 (25.5 mg, 97.1 μmol, 2.4 eq.), p-nitrobenzoic acid (16.2 mg, 97.1 μmol, 2.4 eq.) and DIAD (19 μl, 20 mg, 97 μmol, 2.4 eq.) at 0 °C. The reaction mixture was stirred at 21 °C for 2.5 h, whereupon all volatiles were removed in vacuo. The crude product was purified by flash-chromatography (cyclohexane:ethyl acetate 20:1) to afford (2S,3aS,4R,7S,7aS)-di-tert-butyl-7-(tert-butyldimethylsilyloxy)-4-(4-nitrobenzoyloxy)-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate (24.5 mg, 98%) as a colorless oil.Analysis of the target compound: Rf = 0.50 (cyclohexane:ethyl acetate 5:1). – [α]D20 = –150 (c = 1.00, CHCl3). – 1H NMR (400 MHz, CDCl3, no rotamers visible): δ/ppm = 0.13, 0.18 (2 × s, 6H); 0.91 (2 × s, 9H); 1.41, 1.44 (2 × s, 18H); 1.65 (ddd, J = 12.2, J = 12.2, J = 8.6 Hz, 1H); 2.10 (dddd, J = 11.9, J = 11.9, J = 7.2, J = 3.1 Hz, 1H); 2.30 (ddd, J = 12.2, J = 8.1, J = 7.4 Hz, 1H); 3.85 (dd, J = 11.5, J = 7.9 Hz, 1H); 4.22 (dd, J = 8.5, J = 8.5 Hz, 1H); 4.60 (d, J = 7.8 Hz, 1H); 5.52 (dd, J = 5.5, J = 5.5 Hz, 1H); 5.92 – 6.01 (m, 2H); 8.18 – 8.20 (m, 2H); 8.22 – 8.30 (m, 2H). – 13C NMR (100 MHz, CDCl3, no rotamers visible): δ/ppm = –4.4 (+); –4.0 (+); 18.5 (Cquart); 26.2 (+); 28.0 (+); 28.3 (+); 29.6 (–); 42.7 (+); 59.9 (+); 61.4 (+); 68.0 (+); 72.9 (+); 79.8 (Cquart); 81.0 (Cquart); 123.2 (+); 123.6 (+); 130.8 (+); 135.2 (Cquart); 139.4 (+); 150.7 (Cquart); 153.0 (Cquart); 164.1 (Cquart); 172.5 (Cquart). – IR (KBr): ṽ/cm-1 = 2928 (vw), 1725 (w), 1608 (vw), 1530 (w), 1472 (vw), 1338 (vw), 1337 (w), 1271 (w), 1089 (w), 869 (w), 834 (w). – MS (FAB, matrix: 3-NBA), m/z (%): 619 (8) [MH+], 563 (6) [MH+ – CH2C(CH3)2], 507 (24) [MH+ – 2 × CH2C(CH3)2], 463 (10) [MH+ – 2 × CH2C(CH3)2 – CO2], 449 (100) [MH+ – CH2C(CH3)2 – SiMe2tBu]. – HRMS (FAB, matrix: 3-NBA) C31H47N2O9Si: calc. 619.3051; found 619.3054
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-AXWVANFNVP-UHFFFADPSC-NUHFF-NIAXR-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.201001169A solution of (2S,4R,5S)-di-tert-butyl-5-[(S)-1-(tert-butyldimethylsilyloxy)but-3-enyl]-4-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1,2-dicarboxylate (89.0 mg, 0.148 mmol) in THF (7 ml) was treated with HF/pyridine (70%, 0.32 ml) at 0 °C and the reaction mixture was stirred for 4.5 h. Then, sat. NaHCO3 solution (30 ml) and solid NaHCO3 were added, until gas evolution ceased. The mixture was extracted with ethyl acetate (4 × 20 ml) and the combined organic extracts were dried over Na2SO4. Then all volatiles were removed in vacuo and the crude product was purified by flash-chromatography (cyclohexane:ethyl acetate 5:1) to afford (2S,4R,5S)-di-tert-butyl-5-[(S)-1-(tert-butyldimethylsilyloxy)but-3-enyl]-4-(hydroxymethyl)pyrrolidine-1,2-dicarboxylate (67 mg, 93%) as a colorless oil.Analysis of the target compound: Rf = 0.25 (cyclohexane:ethyl acetate 5:1). – [α]D20 = –42.0 (c = 0.35, CHCl3). – 1H NMR (400 MHz, CDCl3, 2 rotamers 0.60:0.40): δ/ppm = 0.11, 0.13, 0.13, 0.19 (4 × s, 6H); 0.91 (s, 9H); 1.41, 1.44, 1.45, 1.48 (4 × s, 18H); 1.74 – 1.80 (m, 1H); 2.14 – 2.24 (m, 1H); 2.27 – 2.40 (m, 2H); 2.59 – 2.75 (m, 1H); 3.41, 3.59 (2 × sbr, 1H); 3.75 – 3.86 (m, 2H); 4.04 (d, J = 9.1 Hz, 0.6H); 4.08 (dd, J = 7.8, J = 4.8 Hz, 0.4H); 4.12 (d, J = 9.0 Hz, 0.4H); 4.17 (dd, J = 8.0, J = 4.6 Hz, 0.6H); 4.25 (ddd, J = 9.8, J = 4.9, J = 4.9 Hz, 0.4H); 4.46 (ddd, J = 6.4, J = 6.4, J = 4.7 Hz, 0.6H); 4.97 – 5.04 (m, 2H); 5.60 – 5.73 (m, 1H). – 13C NMR (100 MHz, CDCl3, 2 rotamers 0.60:0.40): δ/ppm = –4.8, –4.7, –4.2, –4.0 (2 × +); 18.0 (Cquart); 25.8, 25.9 (+); 27.9, 28.0, 28.3, 28.6 (2 × +); 31.2, 32.4 (–); 38.2, 38.5 (–); 42.8, 43.9 (+); 59.8, 59.9 (+); 60.7, 60.9 (–); 61.5, 61.5 (+); 72.0, 73.6 (+); 79.9, 80.5, 81.1, 81.1 (2 × Cquart); 116.1, 116.8 (–); 135.5, 135.7 (+); 153.4, 153.7 (Cquart); 172.1, 172.2 (Cquart). – IR (KBr): ṽ/cm-1 = 3485 (m), 2957 (m), 2931 (m), 2858 (m), 1741 (s), 1702 (s), 1473 (m), 1384 (s), 1256 (m), 1175 (s), 1150 (s), 1128 (s), 1087 (m), 1058 (m), 1005 (m). – MS (FAB, matrix: 3-NBA), m/z (%): 486 (8) [MH+], 386 (52) [MH+ – CH2C(CH3)2 – CO2], 330 (100) [MH+ – 2 × CH2C(CH3)2 – CO2], 284 (30) [C15H29NO2Si+]. – HRMS (FAB, matrix: 3-NBA) C25H48NO6Si: calc. 486.3251; found 486.3254. – Elemental analysis: C25H47NO6Si (485): calc. C 61.82, H 9.75, N 2.88; found C 62.18, H 9.68, N 2.54