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CAS No. : | 60835-75-8 | MDL No. : | MFCD00143277 |
Formula : | C17H24O8 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GFQYJVLOPVAPGJ-UHFFFAOYSA-N |
M.W : | 356.37 | Pubchem ID : | 2724805 |
Synonyms : |
|
Num. heavy atoms : | 25 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.59 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 8.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 87.07 |
TPSA : | 92.68 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.67 cm/s |
Log Po/w (iLOGP) : | 2.17 |
Log Po/w (XLOGP3) : | -0.28 |
Log Po/w (WLOGP) : | 1.22 |
Log Po/w (MLOGP) : | -0.41 |
Log Po/w (SILICOS-IT) : | 1.76 |
Consensus Log Po/w : | 0.89 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.98 |
Solubility : | 3.69 mg/ml ; 0.0104 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.21 |
Solubility : | 22.1 mg/ml ; 0.0621 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.95 |
Solubility : | 0.397 mg/ml ; 0.00111 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.34 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane for 15h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride Heating; | ||
With oxalyl dichloride | ||
With thionyl chloride at 80℃; for 5h; |
With pyridine; thionyl chloride In dichloromethane for 3h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 13h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 13h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Stage #1: (benzo-18-crown-6)-4-carboxylic acid With thionyl chloride for 2h; Heating; Stage #2: N,N'-bis(5-hydroxy-3-oxapentyl)-2,6-pyridinedicarboxamide With triethylamine In tetrahydrofuran at 20℃; for 24h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / Heating 2: 40 percent / pyridine / benzene / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / Heating 2: 66 percent / pyridine / benzene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In benzene byproducts: water; equimolar amts., refluxing for 10 h (distn. off of water); evapn. (vac.), recrystn. (Et2O/hexane); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In benzene stoich. amts., refluxing for 12 h; evapn. (vac.), chromy. (Sephadex LH-20, CH2Cl2/CHCl3), recrystn. (hexane/CHCl3); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In benzene stoich. amts., refluxing for 6 h; evapn. (vac.), recrystn. (hexane/CHCl3); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In benzene byproducts: AcOH; equimolar amts., refluxing for 4 h; evapn. (vac.), recrystn. (hexane/CHCl3); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 73h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With DMT-MM In tetrahydrofuran; water at 20℃; for 12h; | 4-N-(5,6-heptadienyl)carbamoylbenzo-18-crown-6 (5) To a stirred solution of 4-ethoxycarbonylbenzo-18-crown-6 (26) (1.75 g, 4.94 mmol, 1.00 eq.) and 13 (1.65 g,14.8 mmol, 1.50 eq.) in THF (20.0 mL) and H2O (20.0 mL) was added DMT-MM (4.10 g, 14.8 mmol, 1.50 eq.) at room temperature. After being stirred at the same temperature for 12 h, the reaction mixture was concentrated in vacuo.The residue was purified by silica gel column chromatography with 95:5 CHCl3:MeOH to give 9 (3.29 g, 7.32 mmol,74%). Mp 83-85 °C; 1H NMR (400 MHz, CDCl3): δ 7.39 (d, 1H, J = 2.4 Hz), 7.24 (dd, 1H, J = 2.4, 8.7 Hz), 6.85 (d, 1H, J =8.7 Hz), 6.03 (br-t, 1H, J = 5.3 Hz), 5.10 (q, 1H, J = 6.8 Hz), 4.67 (dt, 2H, J = 3.4, 6.8 Hz), 4.21 (t, 2H, J = 4.8 Hz),4.19 (t, 2H, J = 4.4 Hz), 3.94 (t, 2H, J = 4.8 Hz), 3.92 (t, 2H, J = 4.4 Hz), 3.79-3.75 (m, 4H), 3.73-3.70 (m, 4H), 3.68 (s,4H), 3.43 (dt, 2H, J = 5.3, 6.8 Hz), 2.06 (dtt, 2H, Jk,l = Jl,m = 6.8 Hz, Jl,n = 3.4 Hz), 1.66 (tt, 2H, J = 6.8, 7.2 Hz), 1.51 (tt,2H, J = 7.2, 6.8 Hz); 13C NMR (100 MHz, CDCl3): δ 208.0, 167.0, 151.6, 148.7, 127.6, 120.0, 112.9, 112.4, 89.6, 74.9,70.8, 70.7, 70.6, 69.5, 69.4, 69.0, 68.9, 39.9, 29.1, 27.8, 26.3; FT-IR (KBr): 3274, 2914, 1954, 1640, 1507, 1265, 1121,958, 759 (cm-1); HRMS (ESI-TOF) calcd. for C24H39N2O7M+Na+ 467.2758, found 467.2757. |
71% | With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 0.666667h; | 1.8 To a solution of 4-carboxybenzo-18-crown-6 (32.3 mg, 90.6 μmol, 1.00 eq.) and 1-amino-5,6-heptadiene (30.2 mg, 272 μmol, 3.00 eq.) in a dry methylene chloride solvent (1.00 mL), were added HATU (51.7 mg, 136 μmol, 1.50 eq.), diisopropylethylamine (23.4 μL, 136 μmol, 1.50 eq.), and a catalytic amount of N,N-dimethylaminopyridine at room temperature. The mixture is stirred at room temperature for 40 minutes, and the reaction solution is filtered. The resulting filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=95:5) to obtain a crown ether allene monomer as shown below (39.3 mg, 64.3 μmol, 71%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With DMT-MM In tetrahydrofuran; water at 20℃; for 24h; | 4-(Prop-2-yn-1-ylcarbamoyl)-18-crown-6 (27) To a stirred solution of 26 (94.5 mg, 265 μmol, 1.00 eq.) and prop-2-yn-1-amine (37.0 μL, 530 μmol, 2.00eq.) in THF (1.00 mL) and H2O (1.00 mL) was added DMT-MM (110 mg, 398 μmol, 1.50 eq.) at room temperature. After being stirred at the same temperature for 24 h, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography with 95:5 CHCl3:MeOH to give 27 (75.5 mg, 194 μmol, 73%). 1H NMR (400 MHz, CDCl3): δ 7.44 (s, 1H), 7.31 (d, 1H, J = 7.7 Hz), 6.84 (d, 1H, J = 7.7 Hz), 6.45 (s, 1H), 4.24-4.22(m, 6H), 4.18 (br-s, 4H), 3.93 (t, 2H, J = 4.4 Hz), 3.93 (t, 2H, J = 4.4 Hz), 3.77-3.75 (m, 4H), 3.72-3.70 (m, 4H), 3.68 (s,4H), 2.27 (t, 1H, J = 2.4 Hz); 13C NMR (100 MHz, CDCl3): δ 166.6, 151.3, 148.1, 126.5, 120.4, 112.6, 112.0, 80.0, 77.3,71.3, 70.6, 70.5, 70.4, 70.3, 69.3, 69.2, 68.7, 68.5, 29.5; FT-IR (KBr): 3423, 3251, 2908, 1648, 1508, 1266, 1119, 957,733 (cm-1); HRMS (ESI-TOF) calcd. for C20H28NO7M+H+ 394.1866, found 394.1890 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.2% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h; | Corrole-linked crown ether (2). 4'-Carboxybenzo-18-crown-6 (89 mg, 0.25 mmol), compound 1 (156 mg, 0.25 mmol), (3-dimethylaminopropyl) ethylcarbodiimide monohydrochloride (EDCI, 72 mg,0.375 mmol), and 4,6-dimethyl-2-Pyridinamine (DMAP,15 mg, 0.125 mmol) were dissolved in dry CH2Cl2 (20 mL). The resulting mixture was stirred for 48 h at room temperature. Then, the reaction mixture was diluted with CH2Cl2 (100 mL) and washed with a 0.1 M aqueous HCl, saturated with NaHCO3 and brine, and dried over anhydrous MgSO4. After chromatographic purification (silica, first with CH2Cl2, then with CH2Cl2/MeOH 100 : 5), the corrole-crown ether (198 mg, 82.2% ) was obtained as a deep red solid. 1H NMR spectrum (400 M Hz, CDCl3, δ, ppm: -1.70 br.s (3H), 1.92 s (12H), 2.60 s (6H), 3.68 s (4H), 3.71 4H), 3.77 m (4H), 3.95 m (4H), 4.20 m (4H), 6.85 d (J =8.0 Hz, 1H), 7.54 d (J = 2.0 Hz, 1H), 7.65 d.d (J =8.0 Hz, J' = 2.0 Hz, 1H), 7.26 s (4H), 8.02 d (J =8.4 Hz, 2H), 8.14 d (J = 8.0 Hz, 2H), 8.31 d (J =4.0 Hz, 2H), 8.47 d (J = 4.8 Hz, 2H), 8.51 d (J =4.8 Hz, 2H), 8.87 d (J = 4.0 Hz, 2H); MS (MALDI-TOF):963.4 [M]+, 986.4 [M + Na]+, 1002.4 [M + K]+; λabs (toluene, ε × 10-3): 410 (69.4), 429 (55.9), 567(9.1), 606 (6.5), 639 (4.6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.7% | With piperidine; acetic acid In benzene for 48h; Dean-Stark; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In acetonitrile at 85℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In acetonitrile at 85℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In acetonitrile at 85℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In acetonitrile at 85℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium carbonate In acetonitrile at 85℃; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h; | ||
With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: 4’-carboxybenzo-18-crown-6; dec-9-yn-1-ol With 4-dimethylaminopyridine In dichloromethane at 0℃; for 0.166667h; Stage #2: With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 4-dimethylaminopyridine / dichloromethane / 0.17 h / 0 °C 1.2: 36 h / 0 - 20 °C 2.1: Cupric sulfate; sodium ascorbate powder / N,N-dimethyl-formamide / 12 h / 20 °C / Sealed tube |