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CAS No. : | 2683-82-1 | MDL No. : | MFCD00009627 |
Formula : | C36H46N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XFIIGRBIXXECHR-UHFFFAOYSA-N |
M.W : | 534.78 | Pubchem ID : | 102311 |
Synonyms : |
|
Num. heavy atoms : | 40 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.44 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 183.07 |
TPSA : | 56.3 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) : | -3.54 cm/s |
Log Po/w (iLOGP) : | 5.61 |
Log Po/w (XLOGP3) : | 8.48 |
Log Po/w (WLOGP) : | 6.71 |
Log Po/w (MLOGP) : | 4.39 |
Log Po/w (SILICOS-IT) : | 11.5 |
Consensus Log Po/w : | 7.34 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -8.16 |
Solubility : | 0.00000374 mg/ml ; 0.000000007 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -9.53 |
Solubility : | 0.000000157 mg/ml ; 0.0000000003 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -11.82 |
Solubility : | 0.0000000008 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 7.8 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
With o-tetrachloroquinone In dichloromethane for 24h; Ambient temperature; Yield given; | ||
0.99 g | With oxygen In water; benzene for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With lithium hexamethyldisilazane at 50 - 60℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.4% | With toluene-4-sulfonic acid In water; benzene for 8h; Dean-Stark; Reflux; Inert atmosphere; | |
In acetic acid for 1h; Heating; Yield given; | ||
With oxygen 1.) benzene, 55 deg C, 15 h, 2.) r.t.; Yield given. Multistep reaction; |
With cetyltrimethylammonium chloride In methanol; aq. phosphate buffer at 25℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With ethylene glycol In trifluoroacetic acid at 20℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With phosphorus trichloride In chloroform at 50℃; for 0.0833333h; further reagent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Dimethoxymethane; chloranil; toluene-4-sulfonic acid 1) CH2Cl2, rt, 12 h; Yield given. Multistep reaction; | ||
750 mg | Stage #1: α-(Hydroxymethyl)-3,4-diethylpyrrole With hydrogen bromide In methanol at 20℃; for 2h; Stage #2: With chloranil In tetrahydrofuran at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With recorcinol at 160℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With ethylene glycol In trifluoroacetic acid at 20℃; for 0.166667h; | |
With sulfuric acid In water; acetic acid at 24.85℃; | ||
With trifluoroacetic acid In acetic acid at 34.85 - 54.85℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.5% | With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With N-Bromosuccinimide; hydrogen bromide; acetic acid In chloroform for 0.0833333h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 48h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With sodium formate In chloroform for 24h; Reflux; | |
60% | With acetic acid In chloroform for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With trifluoroacetic acid; sodium nitrite at 20℃; for 0.0833333h; | 5-Nitro-2,3,7,8,12,13,17,18-octaethylporphyrin (2). To 0.04 g (0.0748 mmol) of porphyrin 1 in 3 mL of trifl uoroacetic acid, 0.026 g (0.374 mmol) of NaNO2 was added and mixed at room temperature for 5 min. Chloroform and water were added to the reaction mixture. The organic layer was separated, washed with water, a NaHCO3 solution, again with water, then dried with Na2SO4, and evaporated to a minimal volume. The residue was chromatographed on aluminum oxide with a hexane-dichloromethane (1 : 1) mixture and then with dichloromethane. Yield 0.034 g (0.0586 mmol, 78%). EAS (H2Cl2), λ, nm (log ε): 624 (3.67), 571 (3.74), 537 (3.88), 502 (4.05), 396 (5.08). 1H NMR spectrum, δ, ppm: 10.25 s (2H) and 10.10 s (1H, meso-H), 4.11-4.02 m (12H) and 3.75 s (4H, CH2), 1.93-1.85 m (18H) and 1.69-1.60 m (6H, CH3), -3.85 s and -3.95 s (2H, NH). Mass spectrum, m/z (Irel, %): 579.1 (98) [M] + (calculated for 3645N5O2: 579.8). |
31% | With nitronium tetrafluoborate In pyridine; chloroform at 80℃; for 6h; | |
With nitric acid; acetic acid for 0.0222222h; |
Multi-step reaction with 3 steps 1: dichloromethane; methanol / 1 h / 20 °C 2: iodine / dichloromethane; acetonitrile / 5 h / 20 °C / Inert atmosphere 3: hydrogenchloride; acetic acid / water / 3 h / 20 °C | ||
Multi-step reaction with 3 steps 1: methanol; dichloromethane / 1 h / 20 °C 2: iodine / dichloromethane; acetonitrile / 5 h / 20 °C / Inert atmosphere 3: hydrogenchloride; acetic acid / water / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 47% 2: 10% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With hydrogen In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 2,6-di-t-butyl-4-methylphenoxy magnesium iodide In diethyl ether; chloroform at 50℃; for 0.05h; | |
With triethylamine; magnesium bromide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With fluoro alcohol In chloroform for 0.25h; Ambient temperature; further reagents; | |
57% | With NH-pyrazole; dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 19% 2: 20% | With 2,3,4,5,6-pentachloro-1-fluoropyridin-1-ium trifluoromethanesulfonate In fluorobenzene at 50℃; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: 2,3,7,8,12,13,17,18-octaethyl-porphyrin With osmium(VIII) oxide at 20℃; Stage #2: With hydrogen sulfide at 20℃; Further stages.; | |
66.6% | With osmium(VIII) oxide In pyridine; diethyl ether; dichloromethane for 48h; Ambient temperature; | |
With pyridine; osmium(VIII) oxide; hydrogen sulfide 1. ) ether, CH2Cl2, RT, 48 h, 2. ) ether, CH2Cl2, CH3OH, 25 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 19% 2: 20% 3: 15% | With 2,3,4,5,6-pentachloro-1-fluoropyridin-1-ium trifluoromethanesulfonate In fluorobenzene at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With oxygen; lithium chloride In dimethyl sulfoxide at 190 - 200℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With air; lithium chloride In dimethyl sulfoxide at 200 - 210℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate In chloroform at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With sodium In i-Amyl alcohol at 135℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: n-butyllithium; 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; cyclohexane at -70℃; for 0.25h; Stage #2: With water In tetrahydrofuran; cyclohexane for 0.0833333h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; dichloromethane; cyclohexane for 0.333333h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: 2,3,7,8,12,13,17,18-octaethyl-porphyrin; phenyllithium In tetrahydrofuran; cyclohexane at 40℃; for 0.25h; Stage #2: With water In tetrahydrofuran; cyclohexane Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; dichloromethane; cyclohexane for 0.0833333h; Further stages.; | |
100% | Stage #1: 2,3,7,8,12,13,17,18-octaethyl-porphyrin; phenyllithium In tetrahydrofuran at -40 - 20℃; Stage #2: With water In tetrahydrofuran Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With bis(acetylacetonate)nickel(II) In o-xylene for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: n-butyllithium; 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; cyclohexane at -70℃; for 0.5h; Stage #2: With water-d2 In tetrahydrofuran; cyclohexane for 0.25h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; cyclohexane for 0.333333h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | Stage #1: n-butyllithium; 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran at -70℃; for 0.25h; Stage #2: With diclazuril In tetrahydrofuran at -70℃; for 0.333333h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at -70 - 20℃; for 0.333333h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper diacetate In N,N-dimethyl-formamide Heating; | ||
With copper diacetate In ethanol; 1,2-dichloro-ethane at 80℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: 2,3,7,8,12,13,17,18-octaethyl-porphyrin With pyridine; osmium(VIII) oxide In diethyl ether; dichloromethane at 20℃; for 40h; Stage #2: With hydrogen sulfide In methanol; diethyl ether; dichloromethane for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: LiC6H4-p-NH2; 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran at -40 - 20℃; Stage #2: With water In tetrahydrofuran Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: 4-bromophenyllithium; 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran at -40 - 20℃; Stage #2: With water In tetrahydrofuran Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: 2,3,7,8,12,13,17,18-octaethyl-porphyrin; 4-penten-1-yllithium In tetrahydrofuran at -40 - 20℃; Stage #2: With water In tetrahydrofuran Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: 2,3,7,8,12,13,17,18-octaethyl-porphyrin; C8H5Li In tetrahydrofuran at -40 - 20℃; Stage #2: With water In tetrahydrofuran Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With boron trifluoride diethyl etherate; triethylamine In dichloromethane at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With triethylamine In dichloromethane at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at -70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di(rhodium)tetracarbonyl dichloride In toluene at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With bis(acetylacetonate)oxovanadium In quinoline for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15 mg | Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin for 18h; Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21 mg | Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin for 18h; Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With copper(l) iodide In tetrahydrofuran; pentane at -70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C 4.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 15 h / 20 °C 4.2: 76 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether 5.1: aq. HCl / benzene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C 4.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 15 h / 20 °C 4.2: 76 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether 5.1: aq. HCl / benzene / Heating 5.2: osmium tetraoxide; sodium periodate; acetic acid / tetrahydrofuran; H2O / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C 4.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 15 h / 20 °C 4.2: 76 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether 5.1: aq. HCl / benzene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C 4.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 15 h / 20 °C 4.2: 76 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether 5.1: aq. HCl / benzene / Heating 5.2: osmium tetraoxide; sodium periodate; acetic acid / tetrahydrofuran; H2O / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C 4.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 15 h / 20 °C 4.2: 76 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether 5.1: aq. HCl / benzene / Heating 5.2: osmium tetraoxide; sodium periodate; acetic acid / tetrahydrofuran; H2O / 0 - 20 °C 5.3: t-BuNH2*BH3 / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C 4.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 15 h / 20 °C 4.2: 76 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether 5.1: aq. HCl / benzene / Heating 5.2: osmium tetraoxide; sodium periodate; acetic acid / tetrahydrofuran; H2O / 0 - 20 °C 5.3: t-BuNH2*BH3 / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C 4.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 15 h / 20 °C 4.2: 76 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether 5.1: aqueous HCl / tetrahydrofuran / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C 4.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 15 h / 20 °C 4.2: 76 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether 5.1: aqueous HCl / tetrahydrofuran / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 40 h / 20 °C 1.2: 82 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether / 0.5 h 2.1: 48 percent / aqueous HCl / tetrahydrofuran / 1 h / Heating 3.1: 85 percent / 4-methylmorpholine N-oxide / Pr4NRuO4 / CH2Cl2 / 1.5 h / 20 °C 4.1: osmium tetraoxide; pyridine / CH2Cl2; diethyl ether / 15 h / 20 °C 4.2: 76 percent / hydrogen sulfide / CH2Cl2; methanol; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Br2, AcOH / 0.5 h 2: KOH / 4 h / Heating 3: O2, AcOH | ||
Multi-step reaction with 3 steps 1: Br2, K2CO3 / CH2Cl2; diethyl ether / 0.33 h / Ambient temperature 2: CH2Cl2; diethyl ether / 0.5 h / Ambient temperature 3: 1.) KOH, 2.) AcOH, O2 / 1.) aq. EtOH, reflux, 3 h, 2.) aq. EtOH, reflux, 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: PCl3 2: 2.) KPF6 / 1.) CH2Cl2 | ||
Multi-step reaction with 2 steps 1: PCl3 2: 20 percent / KPF6 / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) 2,6-dimethylpyridine, 2.) air / 1.) CH2Cl2, RT 2: aq. HCl / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 100 percent / P(MeNCH2CH2)3N / tetrahydrofuran; propan-2-ol / 2 h / -20 - -15 °C 2: 17 percent / aq. LiCl, O2 / dimethylsulfoxide / 4 h / 190 - 200 °C | ||
Multi-step reaction with 3 steps 1: 100 percent / P(MeNCH2CH2)3N / tetrahydrofuran; propan-2-ol / 2 h / -20 - -15 °C 2: 87.5 percent / conc. aq. HCl / ethanol / 0.5 h / Heating 3: 67 percent / aq. LiCl, air / dimethylsulfoxide / 2 h / 200 - 210 °C | ||
Multi-step reaction with 3 steps 1: 86 percent / DBU / tetrahydrofuran / 12 h / 20 °C 2: LiAlH4 / tetrahydrofuran / 2 h / 0 - 5 °C 3: 1) methylal, p-TsOH, 2) chloranil / 1) CH2Cl2, rt, 12 h |
Multi-step reaction with 2 steps 1: 86 percent / DBU / tetrahydrofuran / 12 h / 20 °C 2: multistep reaction, a new porphyrin synthesis, other pyrrols | ||
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl alcohol; tetrahydrofuran / 4 h / 20 - 30 °C 2: sodium hydroxide / ethylene glycol / 1 h / Reflux; Inert atmosphere 3: toluene-4-sulfonic acid / benzene; water / 8 h / Dean-Stark; Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87.5 percent / conc. aq. HCl / ethanol / 0.5 h / Heating 2: 67 percent / aq. LiCl, air / dimethylsulfoxide / 2 h / 200 - 210 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (18)O2 In N,N-dimethyl-formamide Refluxing under (18)O2-atmosphere, 2 h.; Ppt. with cold water, washed, dissolved in CH2Cl2, chromatographed on alumina.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 33% 2: 16% | With N-chloro-succinimide In chloroform Inert atmosphere; Reflux; | |
1: 10% 2: 20% | With hydrogenchloride; sodium azide In water at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 72% 2: 10% | Stage #1: 4-bromo-1-ethynylbenzene With n-butyllithium In diethyl ether; hexane at -70 - 20℃; Inert atmosphere; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; diethyl ether; hexane at -20 - 20℃; Inert atmosphere; Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: 3-bromo-1-trifluoromethylbenzene With n-butyllithium In diethyl ether; hexane at -30 - 20℃; Inert atmosphere; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; diethyl ether; hexane at -30℃; for 1h; Inert atmosphere; Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | Stage #1: 3-Bromophenol With n-butyllithium In diethyl ether; hexane at -70 - 20℃; Inert atmosphere; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; diethyl ether; hexane at -70 - -40℃; for 1h; Inert atmosphere; Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | Stage #1: 2-bromonaphthalene With n-butyllithium In diethyl ether; hexane at -50 - 20℃; Inert atmosphere; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; diethyl ether; hexane at -50℃; for 1h; Inert atmosphere; Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: 9-bromophenanthrene With n-butyllithium In diethyl ether; hexane at -30 - 20℃; Inert atmosphere; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; diethyl ether; hexane at -20℃; for 1h; Inert atmosphere; Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | Stage #1: 5-bromoacenaphthene With n-butyllithium In diethyl ether; hexane at -60 - 20℃; Inert atmosphere; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; diethyl ether; hexane at -20℃; for 1h; Inert atmosphere; Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | Stage #1: para-bromotoluene With n-butyllithium In diethyl ether; hexane at -10 - 20℃; Inert atmosphere; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; diethyl ether; hexane at -10 - 0℃; for 1h; Inert atmosphere; Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran at -80 - 20℃; for 1h; Inert atmosphere; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 46% 2: 1% | Stage #1: 1-Bromonaphthalene With n-butyllithium In diethyl ether; hexane at -30 - 20℃; Inert atmosphere; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin In tetrahydrofuran; diethyl ether; hexane at -30℃; for 24h; Inert atmosphere; Further stages; |