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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 = 7.42 (d, J = 2.0 Hz, 1H), 7.31–7.20 (m, 5H), 6.09 (d, J = 2.1 Hz, 1H), 5.44 (s, 2H), 5.06 (sept, J = 6.8 Hz, 1H), 4.00 (sept, J = 6.7 Hz, 1H), 1.34 (d, J = 6.0 Hz, 6H), 1.22 (d, J = 6.2 Hz, 6H)
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 = 8.33 (s, 1H), 7.86–7.82 (m, 2H), 7.44 (d, J = 2.4 Hz, 1H), 7.41–7.35 (m, 3H), 7.29–7.27 (m, 2H), 7.01–6.97 (m, 2H), 6.78 (d, J = 2.4 Hz, 1H), 5.33 (s, 2H), 3.85 (s, 3H)
distortionless enhancement with polarization transfer (DEPT) ()
No full textdataset for distortionless enhancement with polarization transfer (DEPT
infrared absorption spectroscopy (IR) ()
No full textdataset for infrared absorption spectroscopy (IR)
IR (ATR, ṽ) = 3126, 2978, 2952, 2934, 2874, 2217, 1718, 1612, 1579, 1537, 1458, 1446, 1412, 1381, 1368, 1349, 1323, 1315, 1276, 1259, 1231, 1187, 1157, 1133, 1099, 1033, 1021, 1004, 965, 911, 871, 836, 796, 764, 715, 652, 637, 613, 582, 562, 533, 517, 503, 467, 419, 419, 409, 409, 380 cm–1
1H nuclear magnetic resonance spectroscopy (1H NMR) ()
No full textdataset for 1H nuclear magnetic resonance spectroscopy (1H NMR)
1H NMR (400 MHz, Chloroform-d [7.26 ppm], ppm) δ = 8.45 (s, 1H), 7.91–7.89 (m, 2H), 7.82–7.80 (m, 2H), 7.69–7.67 (m, 2H), 7.46–7.43 (m, 2H), 7.38–7.34 (m, 1H), 6.82 (d, J = 0.6 Hz, 1H), 2.50 (s, 3H)
distortionless enhancement with polarization transfer (DEPT) ()
No full textdataset for distortionless enhancement with polarization transfer (DEPT
distortionless enhancement with polarization transfer (DEPT) ((2,2-dimethylchromen-6-yl)methanol)
No full textdataset for distortionless enhancement with polarization transfer (DEPT)
13C NMR (100 MHz, Chloroform-d [77.0 ppm], ppm) δ = 131.1, 128.2, 125.5, 122.2, 116.4
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ZSJATCALDO-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ
No full textThe information given below was retrieved and reworked from the publication: Modular Syntheses of Diversonol-Type Tetrahydroxanthone Mycotoxins: Blennolide C (epi-Hemirugulotrosin A) and Analogues by Emilie M. C. Gérard and Stefan Bräse. 10.1002/chem.200801507To 17.0 mL of a 1:1 mixture of tetrahydrofuran and water, containing 301 mg of 1-hydroxy-4a-propenyl-2,3,4,4a-tetrahydro-xanthene-9-one (1.18 mmol, 1.00 equiv.), 1.00 g of sodium periodate (4.72 mmol, 4.00 equiv.), 9 mg of potassium osmate (236 µmol, 0.02 equiv.) was added 270 µL of 2,6-lutidine (2.36 mmol, 2.00 equiv.). The orange solution was stirred at room temperature for 3.5 hours. After this time, the reaction mixture was quenched with water (15 mL), extracted with dichloromethane (3 × 15 mL). The combined organic layers were washed with a 1 M aqueous solution of hydrochloric acid (15 mL), dried over sodium sulfate, filtered and evaporated under vacuum. The crude product was purified by column chromatography (cyclohexane/ethyl acetate, 5:1). The titled compound was obtained as transparent crystals in 57% yield (164 mg).Analysis of the target compound: Mp = 113 °C (decomposition). – Rf = 0.32 (CH/EE, 5:1). – IR (KBr): 2947 (m), 1851 (m), 1727 (m, ν HC=O), 1605 (m, ν C=O) cm-1. – 1H-NMR (500 MHz, CDCl3): δ = 1.72 – 1.82 (m, 1 H, CH2), 1.89 – 1.96 (m, 1 H, CH2), 2.09 (td, 3J = 13.6 Hz, 2J = 3.8 Hz, 1 H, CH2), 2.27 (td, 3J = 12.8 Hz, 2J = 3.5 Hz, 1 H, CH2), 7.05 – 7.08 (m, 2 H, Harom.), 7.45 (ddd, 3J = 8.3 Hz, 3J = 7.3 Hz, 4J = 1.8 Hz, 1 H, Harom.), 7.85 (dd, 3J = 8.3 Hz, 4J = 1.8 Hz, 1 H, Harom.),9.69 (s, 1 H, CHO), 15.31 (bs, 1 H, OH). – 13C-NMR (125 MHz, CDCl3): δ = 16.6 (–, CH2), 28.6 (–, CH2), 30.0 (–, CH2), 83.5 (Cquart.), 102.4 (Cquart.), 117.5, 120.8 (Cquart.), 122.6 (+, CHarom.), 127.0 (+, CHarom.), 135.7 (+, CHarom.), 158.4 (Cquart.), 180.7 (C-1), 184.8 (C-9), 200.0 (+, CHO). – MS (FAB, matrix: 3-NBA): m/z 245 (0.8) [M + H]+, 215 (100). – HR (FAB, matrix: 3-NBA) (C14H13O4): found 245.0811; calculated 245.0814
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-XRKQLASUTP-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ
No full textThe information given below was retrieved and reworked from the publication: Modular Syntheses of Diversonol-Type Tetrahydroxanthone Mycotoxins: Blennolide C (epi-Hemirugulotrosin A) and Analogues by Emilie M. C. Gérard and Stefan Bräse. 10.1002/chem.200801507To a solution of 26.0 mg of 1-hydroxy-9-oxo-3,4,4a,9-tetrahydro-2H-xanthene-4a-carbaldehyde (110 µmol, 1.00 equiv.) in methanol (1.00 mL) at 0 °C was added 35.0 mg potassium cyanide (530 µmol, 5.00 equiv.) and 186 mg manganese(IV) oxide (2.10 mmol, 20.0 equiv.). The reaction mixture was stirred at 0 °C for 2 hours. After this time, the reaction mixture was filtered through Celite and diluted with diethyl ether (5 mL). The combined organic layers were washed brine (5 mL), dried over sodium sulfate, filtered and evaporated under vacuum. The crude product was purified by column chromatography (cyclohexane/ethyl acetate, 2:1). The titled compound was obtained as a yellow solid in 18% yield (5 mg).Analysis of the target compound: Rf = 0.28 (CH/EE, 2:1). – 1H-NMR (400 MHz, CDCl3): δ = 1.86 – 2.11 (m, 4 H, CH2), 2.65 – 2.79 (m, 2 H, CH2), 3.74 (s, 3 H, OCH3), 3.83 – 3.86 (m, 1 H, CH), 7.29 (ddd, 3J = 8.1 Hz, 3J = 7.1 Hz, 4J = 1.0 Hz, 1 H, Harom.), 7.33 (ddd, 3J = 8.6 Hz, 4J = 1.0 Hz, 5J = 0.5 Hz, 1 H, Harom.), 7.56 (ddd, 3J = 8.7 Hz, 3J = 7.1 Hz, 4J = 1.7 Hz, 1 H, Harom.), 7.93 (ddd, 3J = 8.0 Hz, 4J = 1.7 Hz, 5J = 0.5 Hz, 1 H, Harom.). – 13C-NMR (125 MHz, CDCl3): δ = 19.4 (–, CH2), 25.9 (–, CH2), 28.0 (–, CH2), 38.3 (+, CH), 52.2 (+, OCH3), 116.9 (Cquart.), 117.6 (+, CHarom.), 123.1 (Cquart.), 124.7 (+, CHarom.), 125.9 (+, CHarom.), 133.4 (+, CHarom.), 155.9 (Cquart.), 165.3 (Cquart.), 174.5 (Cquart.), 177.0 (Cquart.). – EI (FAB, matrix: 3-NBA): m/z 259 (100) [M+H]+, 199 (52)
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-VHMUIXRVOK-UHFFFADPSC-NUHFF-NHLRL-NUHFF-ZZZ
No full textThe information given below was retrieved and reworked from the publication: A Unified Strategy Targeting 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 (2S,3aR,7S,7aS)-7-hydroxy-4-keto-3,3a,7,7a-tetrahydro-2H-indole-1,2-dicarboxylic acid ditert-butyl ester (31.5 mg, 89.1 μmol) in ethyl acetate (3 ml) was added Pd/C (10%, 7.5 mg, 7.1 mmol, 8 mol-%). The solution was saturated with hydrogen gas (5 min) and the mixture was stirred with a hydrogen balloon for 3 h. Then it was filtered through celite® and rinsed with ethyl acetate. Then all volatiles were removed in vacuo and the crude product was purified by flash-chromatography (cyclohexane:ethyl acetate 2:1) to afford (2S,3aR,7S,7aS)-Di-tert-butyl-7-hydroxy-4-oxohexahydro-1H-indole-1,2(2H,3H)-dicarboxylate (25.9 mg, 82%) as a white solid.Analysis of the target compound: Rf = 0.13 (cyclohexane:ethyl acetate 2:1). – m.p.: 112 – 114 °C. – [α]D20 = –104 (c = 0.75, CHCl3). – 1H NMR (400 MHz, CDCl3): δ/ppm = 1.44, 1.46, (2 × s, 18H); 1.81 (dddd, J = 11.9, J = 11.9, J = 11.9, J = 6.1 Hz, 1H); 2.08 – 2.14 (m, 2H); 2.28 (ddd, J = 12.8, J = 12.8, J = 8.8 Hz, 1H); 2.36 – 2.45 (m, 2H); 3.13 (ddd, J = 12.2, J = 8.3, J = 8.3 Hz, 1H); 3.84 (ddd, J = 11.9, J = 8.4, J = 3.6 Hz, 1H); 4.19 – 4.23 (m, 2H); 5.65 (s, 1H). – 13C NMR (100 MHz, CDCl3, second rotamer only in traces in signals for C(CH3)3 visible): δ/ppm = 27.9, 28.0, 28.2, 28.3 (2 × +); 29.0 (–); 32.5 (–); 35.7 (–); 48.0 (+); 59.9, 65.3 (2 × +); 72.9 (+); 81.9, 82.0 (2 × Cquart); 156.9 (Cquart); 170.8 (Cquart); 209.2 (Cquart). – IR (ATR Diamant): ṽ/cm-1 = 3331 (vw), 2980 (w), 1730 (w), 1707 (w), 1664 (m), 1456 (w), 1396 (m), 1366 (m), 1308 (w), 1275 (w), 1253 (w), 1143 (w), 1070 (m), 841 (w). – MS (FAB, matrix: 3-NBA), m/z (%): 356 (5) [MH+], 300 (18) [MH+ – CH2C(CH3)2], 244 (100) [MH+ – 2 × CH2C(CH3)2], 200 (42) [MH+ – 2 × CH2C(CH3)2 – CO2]. – HRMS (FAB, matrix: 3-NBA) C18H30NO6: calc. 356.2073; found 356.2074. – Elemental analysis: C18H29NO6 (355): calc. C 60.83, H 8.22, N 3.94; found C 60.21, H 8.14, N 3.62