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mass spectrometry (MS) ()
No full textdataset for mass spectrometry (MS)
MS (FAB, 3-NBA), m/z (%): 326 (2) [M+H]+, 298 (100), 170 (11), 116 (11), 102 (11). HRMS–FAB (C19H14N6) (m/z): [M+H]+ Calcd 326.1274; Found 326.1275
13C nuclear magnetic resonance spectroscopy (13C NMR) ()
No full textdataset for 13C nuclear magnetic resonance spectroscopy (13C NMR)
13C NMR (100 MHz, Chloroform-d [77.2 ppm], ppm) δ = 148.0 (Cq), 147.8 (Cq), 142.6 (Cq), 142.0 (Cq), 133.5 (2C, CH), 130.2 (Cq), 129.0 (2C, CH), 128.6 (CH), 126.0 (2C, CH), 124.8 (2C, CH), 118.1 (Cq), 116.9 (CH), 111.7 (Cq), 100.2 (CH), 13.4 (CH3)
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-PXALYYVERR-UHFFFADPSC-NUHFF-NQNCV-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,3aR,7S,7aS)-di-tert-butyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate and epi-(2S,3aR,7S,7aS)-di-tert-butyl-7-(tert-butyldimethylsilyloxy)-4-hydroxy-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate (0.90:0.10) (35.0 mg, 74.5 μmol) and DMAP (27.3 mg, 0.224 mmol, 3.0 eq.) in dichloromethane (2.5 ml) was treated dropwise with acetic anhydride (17 μl, 19 mg, 2.5 eq.) and the reaction mixture was stirred at room temperature for 3 h. Then water (10 ml) was added, phases were separated and the aqueous phase was extracted with ethyl acetate (4 × 10 ml). The combined organic extracts were washed with brine (10 ml), dried over Na2SO4. Then all volatiles were removed in vacuo and the crude product was purified by flash-chromatography (cyclohexane:ethyl acetate 10:1) to afford (2S,3aR,4S,7S,7aS)-Di-tert-butyl-4-acetoxy-7-(tert-butyldimethylsilyloxy)- 2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate (24.7 mg, 65%) and a mixture of epimers (2S,3aR,4S,7S,7aS)-Di-tert-butyl-4-acetoxy-7-(tert-butyldimethylsilyloxy)- 2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate and epi-(2S,3aR,4S,7S,7aS)-Di-tert-butyl-4-acetoxy-7-(tert-butyldimethylsilyloxy)-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate (0.43:0.57) (7 mg, 18%) as colorless oils.Analysis of the target compound: (2S,3aR,4S,7S,7aS)-Di-tert-butyl-4-acetoxy-7-(tert-butyldimethylsilyloxy)-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate: Rf = 0.32 (cyclohexane:ethyl acetate 5:1); epi-(2S,3aR,4S,7S,7aS)-Di-tert-butyl-4-acetoxy-7-(tert-butyldimethylsilyloxy)-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate: Rf = 0.24 (cyclohexane:ethyl acetate 5:1). – analytics for (2S,3aR,4S,7S,7aS)-Di-tert-butyl-4-acetoxy-7-(tert-butyldimethylsilyloxy)-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate: – [α]D20 = –3.50 (c = 1.0, CHCl3). – 1H NMR (400 MHz, CDCl3, 2 rotamers 0.67:0.33): δ/ppm = 0.04, 0.05, 0.07, 0.12 (4 × s, 6H); 0.86 (s, 9H); 1.41, 1.45, 1.46, 1.49 (4 × s, 18H); 1.77 – 1.85 (m, 0.33H); 1.80 (dd, J = 13.3, J = 7.4 Hz, 0.67H); 2.07, 2.07 (2 × s, 3H); 2.11 (ddd, J = 13.1, J = 13.1, J = 9.3, 1H); 3.07 (dddd, J = 13.5, J = 7.8, J = 7.8, J = 7.8 Hz, 0.67H); 3.16 (dddd, J = 13.5, J = 7.6, J = 7.6, J = 7.6 Hz, 0.33H); 4.08 (d, J = 9.0 Hz, 0.67H); 4.13 (d, J = 8.9 Hz, 0.33H); 4.17 (dd, J = 8.7, J = 2.6 Hz, 0.33H); 4.20 (dd, J = 8.7, J = 2.6 Hz, 0.67H); 4.30 (dd, J = 4.6, J = 2.7 Hz, 0.33H); 4.37 (dd, J = 4.7, J = 2.7 Hz, 0.67H); 5.65 – 5.69 (m, 1H); 5.74 (d, Jcis = 10.0 Hz, 0.67H); 5.80 (d, Jcis = 9.9 Hz, 0.33H); 5.94 (ddd, Jcis = 9.7, J = 4.8, J = 2.3 Hz, 0.67H); 5.95 – 6.00 (m, 0.33H). – 13C NMR (100 MHz, CDCl3, 2 rotamers 0.67:0.33): δ/ppm = –4.8, –4.6, –4.5, –4.1 (2 × +); 18.0 (Cquart); 21.1 (+); 25.8, 25.8 (+); 27.9, 28.0, 28.3, 28.6 (2 × +), 29.8, 30.9 (–); 38.8, 40.0 (+); 60.4, 60.8 (+); 63.5 (+); 65.8, 66.4 (+); 69.7, 69.7 (+); 79.8, 80.6, 81.2, 81.2 (2 × Cquart); 130.9, 132.5 (+); 131.2, 131.5 (+); 154.1, 155.2 (Cquart); 170.2, 170.3 (Cquart); 172.3, 172.4 (Cquart). – analytics for the mixture of (2S,3aR,4S,7S,7aS)-Di-tert-butyl-4-acetoxy-7-(tert-butyldimethylsilyloxy)-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate and epi-(2S,3aR,4S,7S,7aS)-Di-tert-butyl-4-acetoxy-7-(tert-butyldimethylsilyloxy)-2,3,3a,4-tetrahydro-1H-indole-1,2(7H,7aH)-dicarboxylate (0.90:0.10): – IR (KBr): ṽ/cm-1 = 2956 (m), 2931 (m), 2857 (m), 1740 (m), 1710 (m), 1473 (w), 1368 (m), 1300 (w), 1237 (m), 1153 (m), 1113 (m), 1062 (m), 1040 (m), 838 (w). – MS (FAB, matrix: 3-NBA), m/z (%): 512 (4) [MH+], 456 (6) [MH+ – CHC(CH3)2], 400 (12) [MH+ – 2 × CH2C(CH3)2], 356 (4) [MH+ – 2 × CH2C(CH3)2 – CO2], 342 (100) [MH+ – CH2C(CH3)2 – SiMe2tBu]. – HRMS (FAB, matrix: 3-NBA) C26H46NO7Si: calc. 512.3044; found 512.3046
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-TZDKAHJGNH-UHFFFADPSC-NUHFF-NHLRL-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 (2S,3aR,6S,6aS)-4-hydroxy-6-[(E)-prop-1-enyl]-4-vinyl-3,3a,6,6a-tetrahydro-2H-furo[3,4-b]pyrrole-1,2-dicarboxylic acid di-tert-butyl ester (499 mg, 1.26 mmol) in toluene (50 ml) Grubbs II catalyst (32.1 mg, 37.9 μmol, 3 mol-%) was added in one portion and the reaction mixture was heated at reflux temperature for 3.5 h. The solvent was removed under reduced pressure and the crude product was purified by flash-chromatography (cyclohexane:ethyl acetate 4:1) to afford (2S,3aR,7S,7aS)-7-hydroxy-4-keto-3,3a,7,7a-tetrahydro-2H-indole-1,2-dicarboxylic acid di-tert-butyl ester (322 mg, 72%) as a slightly yellow solid.Analysis of the target compound: Rf = 0.27 (cyclohexane:ethyl acetate, 2:1). – m.p.: 157 – 158 °C. – [α]D20 = –109.6 (c = 0.36, CHCl3). – 1H NMR (400 MHz, CDCl3): δ/ppm = 1.46, 1.47, (2 × s, 18H), 2.21 (ddd, J = 13.4, J = 13.4, J = 8.9 Hz, 1H), 2.33 (dd, J = 13.1, J = 7.4 Hz, 1H), 3.20 (ddd, J = 13.8, J = 9.1, J = 7.3 Hz, 1H), 4.26 (dd, J = 8.7 Hz, 1H), 4.40 (dd, J = 9.1, J = 9.1 Hz, 1H), 4.47 (ddd, J = 7.3, J = 2.2, J = 2.2 Hz, 1H), 5.67 (sbr, 1H), 6.02 (dd, Jcis = 10.3, J = 2.4 Hz, 1H), 6.85 (dd, Jcis = 10.3, J = 2.0 Hz, 1H). – 13C NMR (100 MHz, CDCl3, no rotamers observable): δ/ppm = 28.0 (+), 28.2 (+), 32.3 (–), 44.2 (+), 60.0 (+), 64.0 (+), 71.1 (+), 82.0 (Cquart), 82.2 (Cquart), 127.2 (+), 150.9 (+), 156.6 (Cquart), 170.7 (Cquart), 196.2 (Cquart). – IR (KBr): ṽ/cm-1 = 3375 (m), 3007 (w), 2980 (m), 2935 (m), 1732 (m), 1669 (s), 1622 (m), 1477 (m), 1458 (m), 1402 (m), 1370 (m), 1309 (m), 1225 (m), 1160 (m), 1073 (m), 954 (m). – MS (FAB, matrix: 3-NBA), m/z (%): 354 (17) [MH+], 298 (30) [MH+ – CH2C(CH3)2], 242 (100) [MH+ – 2 × CH2C(CH3)2], 198 (30) [MH+ – CH2C(CH3)2 – CO2tBu]. – HRMS (FAB, matrix: 3-NBA) C18H28NO6: calcd. 354.1917; found 354.1913. – Elemental analysis: C18H27NO6 (353): calcd. C 61.17, H 7.70, N 3.96; found C 61.13, H 7.66, N 3.86
1H--1H correlation spectroscopy (1H-1H COSY) (cyclohepta-2,4,6-trien-1-one)
No full textdataset for 1H--1H correlation spectroscopy (1H-1H COSY
infrared absorption spectroscopy (IR) ()
No full textdataset for infrared absorption spectroscopy (IR)
IR (ATR, ṽ) = 3352, 3133, 3104, 2995, 2921, 2851, 2472, 2387, 2357, 2259, 2230, 2118, 2050, 1919, 1792, 1677, 1605, 1579, 1545, 1511, 1475, 1449, 1434, 1378, 1315, 1298, 1271, 1238, 1207, 1180, 1147, 1120, 1111, 1081, 1057, 1030, 1016, 976, 956, 843, 812, 783, 724, 694, 677, 654, 622, 601, 575, 560, 547, 528, 517, 500, 473, 456, 404, 384 cm–1
distortionless enhancement with polarization transfer (DEPT) ()
No full textdataset for distortionless enhancement with polarization transfer (DEPT
1H--13C heteronuclear single quantum coherence (1H-13C HSQC) ((2,2-dimethylchromen-6-yl)methanol)
No full textdataset for 1H--13C heteronuclear single quantum coherence (1H-13C HSQC
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-OUJKSILOOC-UHFFFADPSC-NUHFF-NNLGR-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.200801507A suspension of 6.20 g 4-methyl-6-methoxysalicylaldehyde (37.3 mmol, 1.00 equiv.), 1.27 g imidazole (18.7 mmol, 0.50 equiv.) and 8.38 g 4-hydroxycyclohexen-1-one (9, 74.6 mmol, 2.00 equiv.) in a 60 mL 2:1 mixture of water and dioxane was placed under ultrawaves promotion for 7 days. The reaction mixture was extracted with ethyl acetate (3 × 150 mL), dried over sodium sulfate and evaporated. The crude product was then purified by flash chromatography yielding 5.25 g (55%) of yellow solid as a 2:1 mixture of separable cis/trans isomers.Analysis of the target compound: Cis-isomer: 1H-NMR (500 MHz, CDCl3): δ = 1.76 – 1.94 (m, 1 H, CH2), 2.15 – 2.25 (m, 1 H, CH2), 2.31 (s, 3 H, CH3), 2.41 – 2.56 (m, 1 H, CH2), 2.64 (ddd, 2J = 18.4 Hz, 3J = 5.5 Hz, 3J =2.5 Hz, 1 H, CH2), 2.74 (bs, 1 H, OH), 3.83 (s, 3 H, OCH3), 4.22 – 4.32 (m, 1 H, H-4), 4.73 (dd, 3J = 8.6 Hz, 4J = 2.4 Hz, 1 H, H-4a), 6.20 (s, 1 H, Harom.), 6.38 (s, 1 H, Harom.), 7.82 (dd, 4J = 2.4 Hz, 5J = 0.6 Hz, 1 H, H-9). – 13C-NMR (125 MHz, CDCl3): δ = 22.5 (+, CH3), 25.9 (–, CH2), 36.7 (–, CH2), 55.7 (+, OCH3), 71.3 (+, C-4), 80.0 (+, C-4a), 105.1 (+, CHarom.), 109.2 (+, CHarom.), 109.2 (Cquart.), 123.9 (Cquart.), 129.3 (+, C-9), 144.5 (Cquart.), 155.8 (Cquart.), 158.0 (Cquart.), 195.3 (C-1). Trans-isomer: 1H-NMR (500 MHz, CDCl3): δ = 1.82 – 1.90 (m, 1 H, CH2), 2.30 (s, 3 H, CH3), 2.29 – 2.42 (m, 2 H, CH2), 2.56 (bs, 1 H, OH), 2.83 (ddd, 2J = 18.1 Hz, 3J = 13.4 Hz, 3J = 6.6 Hz, 1 H, CH2), 3.82 (s, 3 H, OCH3), 4.45 – 4.47 (m, 1 H, H-4), 4.95 (dd, 3J = 2.8 Hz, 4J = 2.5 Hz, 1 H, H-4a), 6.30 (s, 1 H, Harom.), 6.35 (s, 1 H, Harom.), 7.85 (d, 4J = 2.2 Hz, 1 H, H-9). – 13C-NMR (125 MHz, CDCl3): δ = 22.4 (+, CH3), 23.7 (–, CH2), 32.1 (–, CH2), 55.7 (+, OCH3), 65.1 (+, C-4), 77.1 (+, C-4a), 105.2 (+, CHarom.), 109.2 (+, CHarom.), 109,2 (Cquart.), 124.3 (Cquart.), 128.7 (+, C-9), 144.0 ( Cquart.), 155.5 (Cquart.), 157.9 (Cquart.), 196.6 (C-1)
Short-RInChIKey=SA-FUHFF-UHFFFADPSC-FWWMOVUHVC-UHFFFADPSC-NUHFF-NGCGX-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 3.53 g of trans-4-hydroxy-8-methoxy-6-methyl-2,3,4,4a-tetrahydroxanthen-1-one (13.6 mmol, 1.00 equiv.) in dry dichloromethane (45.0 mL) was successively added 3.38 mL N,N-diisopropylethylamine DIPEA (20.4 mmol, 1.50 equiv.) and 2.31 mL of 1-chloromethoxy-2-methoxyethane MEM-Cl (20.4 mmol, 1.50 equiv.). The resulting mixture was stirred at room temperature for 16 hours. The reaction was then quenched with water (50 mL), and extracted with dichloromethane (3 × 30 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate, filtered and evaporated under vacuum. The crude product was purified by column chromatography (cyclohexane/ethyl acetate, 2:1). Trans-8-methoxy-4-(2-methoxy-ethoxymethoxy-)-6-methyl-2,3,4,4a-tetrahydroxanthen-1-one was obtained as a yellow solid in 53% yield (2.50 g).Analysis of the target compound: Mp = 78-84 °C – Rf = 0.18 (CH/EE, 2:1). – 1H-NMR (400 MHz, CDCl3): δ = 1.73 – 1.87 (m, 1 H, CH2), 2.25 – 2.45 (m, 2 H, CH2), 2.28 (s, 3 H, CH3), 2.73 (ddd, 2J = 18.6 Hz, 3J = 13.5 Hz, 3J = 6.7 Hz, 1 H, CH2), 3.40 (s, 3 H, OCH3), 3.53 – 3.61 (m, 2 H, O-CH2-CH2-O), 3.69–3.78 (m, 2 H, O-CH2-CH2-O), 3.80 (s, 3 H, OCH3), 4.45 – 4.48 (m, 1 H, H-4), 4.88 (d, 2J = 7.0 Hz, 1 H, O-CH2-O), 4.97 (d, 2J = 7.0 Hz, 1 H, O-CH2-O), 5.00–5.03 (m, 1 H, H-4a), 6.24 (s, 1 H, Harom.), 6.29 (s, 1 H, Harom.), 7.83 (d, 4J = 2.4 Hz, 1 H, H-9). – 13C-NMR (100 MHz, CDCl3): δ = 22.4 (+, CH3), 22.9 (–, CH2), 32.8 (–, CH2), 55.6 (+, OCH3), 59.0 (+, OCH3), 67.1 (–, O-CH2-CH2-O), 69.9 (+, C-4), 71.7 (–,O-CH2-CH2-O), 76.7 (+, C-4a), 94.9 (–, O-CH2-O), 104.8 (+, CHarom.), 108.9 (Cquart.), 109.2 (+, CHarom.), 124.6 (Cquart.), 128.3 (+, C-9), 143.9 (Cquart.), 156.0 (Cquart.), 157.8 (Cquart.), 196.3 (C-1)