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[ CAS No. 19417-59-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 19417-59-5
Chemical Structure| 19417-59-5
Chemical Structure| 19417-59-5
Structure of 19417-59-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 19417-59-5 ]

CAS No. :19417-59-5 MDL No. :MFCD14705058
Formula : C12H16Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :JMDJLONNYRBOTA-UHFFFAOYSA-N
M.W : 320.06 Pubchem ID :13592659
Synonyms :

Calculated chemistry of [ 19417-59-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 6
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.34
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.34
Log Po/w (XLOGP3) : 4.68
Log Po/w (WLOGP) : 4.34
Log Po/w (MLOGP) : 4.93
Log Po/w (SILICOS-IT) : 5.27
Consensus Log Po/w : 4.51

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.69
Solubility : 0.00648 mg/ml ; 0.0000202 mol/l
Class : Moderately soluble
Log S (Ali) : -4.41
Solubility : 0.0125 mg/ml ; 0.0000391 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.51
Solubility : 0.0000991 mg/ml ; 0.00000031 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 19417-59-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 19417-59-5 ]

* 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.

  • Downstream synthetic route of [ 19417-59-5 ]

[ 19417-59-5 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 19417-58-4 ]
  • [ 19417-59-5 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogen bromide at 100℃; for 2h;
78% With sulfuric acid; sodium bromide In water for 4.5h; Reflux; 11 1,4-Bis(3-bromopropyl)benzene (C4) An emulsion of 1,4-bis(3-hydroxypropyl)benzene (9.0 g, 46.3 mmol) and sodium bromide (24.0 g, 0.23 mol) in deionized water (25 mL) was heated to reflux, while concentrated sulfuric acid (17 mL) was added dropwise over 1 h. After the addition, heating under reflux was continued for additional 3.5 h. The solution was cooled to room temperature, diluted with water (40 mL), and extracted with CH2Cl2 (2*150 mL). The combined organic layers were washed with saturated solution of NaHCO3 (100 mL), saturated NaCl solution (100 mL) and dried over MgSO4. The solvent was evaporated and the residue was purified by column chromatography (silica gel, EtOAc:hexanes, 1:40) to yield 1,4-bis(3-bromopropyl)benzene (11.6 g, 78%) as a colorless oil. 1H NMR (CDCl3): δ=7.15 (s, 4 H), 3.41 (t, J=6.6 Hz, 4 H), 2.77 (t, J=7.1 Hz, 4 H), 2.18 (m, 4 H). 13C NMR (CDCl3): δ=138.3, 128.7, 34.2, 33.4, 33.3. This known compound was prepared by a method different from the one described in Matsuoka, T., Negi, T., Otsubo, T., Sakata, Y., Misumi, S. Bull. Chem. Soc., Japan, 1972, 45, 1825-1833 and Ruzicka, L.; Buijs, J. B.; Stoll, M. Helv. Chim. Acta 1932, 15, 1220.
With hydrogen bromide at 120 - 130℃;
With pyridine; phosphorus tribromide
With hydrogen bromide

  • 2
  • [ 19417-59-5 ]
  • [ 90-02-8 ]
  • [ 70185-71-6 ]
YieldReaction ConditionsOperation in experiment
78.1% With potassium hydroxide In ethanol Heating;
  • 3
  • [ 3978-81-2 ]
  • [ 19417-59-5 ]
  • 4,4'-di-(tert-butyl)-1,1'-(1,4-phenylenedi-3,1-propanediyl)bis(pyridinium) dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In acetonitrile at 20℃; for 72h;
  • 4
  • [ 623-27-8 ]
  • [ 19417-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 67 percent / NaH / benzene / 72 h / 60 °C 2: 91 percent / NiCl2*6H2O; NaBH4 / ethanol / 6 h / 20 °C 3: 81 percent / LiAlH4 / tetrahydrofuran / 3.5 h / 20 °C 4: 81 percent / aq. HBr / 2 h / 100 °C
Multi-step reaction with 6 steps 1: piperidine / pyridine / 110 - 130 °C 2: SOCl2, DMF 3: Heating 4: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 5: LiAlH4 / tetrahydrofuran / 50 - 60 °C 6: HBr / 120 - 130 °C
  • 5
  • [ 19417-59-5 ]
  • [ 144582-02-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: ethanol 2: aq. KOH 3: SOCl2 / 0.5 h / Heating 4: 57 percent / SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: 80 percent / B2H6 / tetrahydrofuran 6: 86 percent / PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / 2 h / Heating
  • 6
  • [ 19417-59-5 ]
  • [ 144582-28-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: SOCl2 / Heating 4: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: B2H6 / tetrahydrofuran 6: PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / Heating
  • 7
  • [ 19417-59-5 ]
  • [ 144582-03-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: ethanol 2: aq. KOH 3: SOCl2 / 0.5 h / Heating 4: 57 percent / SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: 80 percent / B2H6 / tetrahydrofuran 6: 86 percent / PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / 2 h / Heating 9: POCl3 / CH2Cl2 / 0.5 h
  • 8
  • [ 19417-59-5 ]
  • [ 144582-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating
  • 9
  • [ 19417-59-5 ]
  • [ 144582-31-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: SOCl2 / Heating 4: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: B2H6 / tetrahydrofuran 6: PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / Heating 9: POCl3 / CH2Cl2
  • 10
  • [ 19417-59-5 ]
  • [ 144582-30-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: PhCH2ONa / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating
  • 11
  • [ 19417-59-5 ]
  • [ 144582-01-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: ethanol 2: aq. KOH 3: SOCl2 / 0.5 h / Heating 4: 57 percent / SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: 80 percent / B2H6 / tetrahydrofuran 6: 86 percent / PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr
  • 12
  • [ 19417-59-5 ]
  • [ 144582-25-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: SOCl2 / Heating 4: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: B2H6 / tetrahydrofuran 6: PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr
  • 13
  • [ 19417-59-5 ]
  • [ 144582-32-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2
  • 14
  • [ 19417-59-5 ]
  • [ 144582-33-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: PhCH2ONa / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2
  • 15
  • [ 19417-59-5 ]
  • [ 144582-26-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr
  • 16
  • [ 19417-59-5 ]
  • [ 144582-27-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: PhCH2ONa / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr
  • 17
  • [ 19417-59-5 ]
  • [ 144581-98-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr
  • 18
  • [ 19417-59-5 ]
  • [ 144582-22-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr
  • 19
  • [ 19417-59-5 ]
  • 7,17-Diethyl-2,8,12,18-tetramethyl-3,13-<phenylene-1,4-bis(tetramethylene)>porphyrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1: ethanol 2: aq. KOH 3: SOCl2 / 0.5 h / Heating 4: 57 percent / SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: 80 percent / B2H6 / tetrahydrofuran 6: 86 percent / PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / 2 h / Heating 9: POCl3 / CH2Cl2 / 0.5 h 10: 76.9 percent / cyclohexylamine / toluene / 2 h / Heating 11: SO2Cl2 / CH2Cl2 / 0.5 h / Ambient temperature 12: 92 percent / acetic acid / 0.5 h / 70 °C 13: 93 percent / aq. KOH / propan-1-ol / 3 h / Heating 14: dimethylformamide / 2 h / Heating 15: p-TsOH / CH2Cl2; methanol; tetrahydrofuran
  • 20
  • [ 19417-59-5 ]
  • [ 144582-04-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: ethanol 2: aq. KOH 3: SOCl2 / 0.5 h / Heating 4: 57 percent / SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: 80 percent / B2H6 / tetrahydrofuran 6: 86 percent / PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / 2 h / Heating 9: POCl3 / CH2Cl2 / 0.5 h 10: 76.9 percent / cyclohexylamine / toluene / 2 h / Heating
  • 21
  • [ 19417-59-5 ]
  • [ 144582-34-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: SOCl2 / Heating 4: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: B2H6 / tetrahydrofuran 6: PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / Heating 9: POCl3 / CH2Cl2 10: cyclohexylamine / toluene / Heating
  • 22
  • [ 19417-59-5 ]
  • 7,17-Diethyl-2,8,12,18-tetramethyl-3,13-<phenylene-1,4-bis(pentamethylene)>porphyrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: SOCl2 / Heating 4: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: B2H6 / tetrahydrofuran 6: PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / Heating 9: POCl3 / CH2Cl2 10: cyclohexylamine / toluene / Heating 11: SO2Cl2 / CH2Cl2 / Ambient temperature 12: acetic acid / 70 °C 13: aq. KOH / propan-1-ol / Heating 14: dimethylformamide / 2 h / Heating 15: p-TsOH / CH2Cl2; methanol; tetrahydrofuran
  • 23
  • [ 19417-59-5 ]
  • C42H54N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1: ethanol 2: aq. KOH 3: SOCl2 / 0.5 h / Heating 4: 57 percent / SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: 80 percent / B2H6 / tetrahydrofuran 6: 86 percent / PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / 2 h / Heating 9: POCl3 / CH2Cl2 / 0.5 h 10: 76.9 percent / cyclohexylamine / toluene / 2 h / Heating 11: SO2Cl2 / CH2Cl2 / 0.5 h / Ambient temperature 12: 92 percent / acetic acid / 0.5 h / 70 °C 13: 93 percent / aq. KOH / propan-1-ol / 3 h / Heating 14: dimethylformamide / 2 h / Heating
  • 24
  • [ 19417-59-5 ]
  • C44H58N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: SOCl2 / Heating 4: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: B2H6 / tetrahydrofuran 6: PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / Heating 9: POCl3 / CH2Cl2 10: cyclohexylamine / toluene / Heating 11: SO2Cl2 / CH2Cl2 / Ambient temperature 12: acetic acid / 70 °C 13: aq. KOH / propan-1-ol / Heating 14: dimethylformamide / 2 h / Heating
  • 25
  • [ 19417-59-5 ]
  • [ 144582-05-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: ethanol 2: aq. KOH 3: SOCl2 / 0.5 h / Heating 4: 57 percent / SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: 80 percent / B2H6 / tetrahydrofuran 6: 86 percent / PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / 2 h / Heating 9: POCl3 / CH2Cl2 / 0.5 h 10: 76.9 percent / cyclohexylamine / toluene / 2 h / Heating 11: SO2Cl2 / CH2Cl2 / 0.5 h / Ambient temperature
  • 26
  • [ 19417-59-5 ]
  • (E)-3-{5-Chloromethyl-4-[5-(4-{5-[2-chloromethyl-5-((E)-2-cyano-2-methoxycarbonyl-vinyl)-4-methyl-1H-pyrrol-3-yl]-pentyl}-phenyl)-pentyl]-3-methyl-1H-pyrrol-2-yl}-2-cyano-acrylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: SOCl2 / Heating 4: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: B2H6 / tetrahydrofuran 6: PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / Heating 9: POCl3 / CH2Cl2 10: cyclohexylamine / toluene / Heating 11: SO2Cl2 / CH2Cl2 / Ambient temperature
  • 27
  • [ 19417-59-5 ]
  • 7,17-Diethyl-2,8,12,18-tetramethyl-3,13-<2-acetamidophenylene-1,4-bis(tetramethylene)>porphyrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 19 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating 15: SO2Cl2 / CH2Cl2 / Ambient temperature 16: acetic acid / 70 °C 17: aq. KOH / propan-1-ol / Heating 18: dimethylformamide / 2 h / Heating 19: p-TsOH / CH2Cl2; methanol; tetrahydrofuran
  • 28
  • [ 19417-59-5 ]
  • [ 144582-00-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr
  • 29
  • [ 19417-59-5 ]
  • [ 144582-35-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating
  • 30
  • [ 19417-59-5 ]
  • [ 144582-36-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: PhCH2ONa / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating
  • 31
  • [ 19417-59-5 ]
  • [ 144582-24-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: PhCH2ONa / 100 °C / 12 Torr
  • 32
  • [ 19417-59-5 ]
  • 7,17-Diethyl-2,8,12,18-tetramethyl-3,13-<2-acetamidophenylene-1,4-bis(pentamethylene)>porphyrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 19 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: PhCH2ONa / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating 15: SO2Cl2 / CH2Cl2 / Ambient temperature 16: acetic acid / 70 °C 17: aq. KOH / propan-1-ol / Heating 18: dimethylformamide / 2 h / Heating 19: p-TsOH / CH2Cl2; methanol; tetrahydrofuran
  • 33
  • [ 19417-59-5 ]
  • N-(2,5-Bis-{4-[2-(3-ethyl-4-methyl-1H-pyrrol-2-ylmethyl)-5-formyl-4-methyl-1H-pyrrol-3-yl]-butyl}-phenyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 18 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating 15: SO2Cl2 / CH2Cl2 / Ambient temperature 16: acetic acid / 70 °C 17: aq. KOH / propan-1-ol / Heating 18: dimethylformamide / 2 h / Heating
  • 34
  • [ 19417-59-5 ]
  • N-(2,5-Bis-{5-[2-(3-ethyl-4-methyl-1H-pyrrol-2-ylmethyl)-5-formyl-4-methyl-1H-pyrrol-3-yl]-pentyl}-phenyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 18 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: PhCH2ONa / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating 15: SO2Cl2 / CH2Cl2 / Ambient temperature 16: acetic acid / 70 °C 17: aq. KOH / propan-1-ol / Heating 18: dimethylformamide / 2 h / Heating
  • 35
  • [ 19417-59-5 ]
  • (E)-3-{4-[4-(2-Acetylamino-4-{4-[2-chloromethyl-5-((E)-2-cyano-2-methoxycarbonyl-vinyl)-4-methyl-1H-pyrrol-3-yl]-butyl}-phenyl)-butyl]-5-chloromethyl-3-methyl-1H-pyrrol-2-yl}-2-cyano-acrylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating 15: SO2Cl2 / CH2Cl2 / Ambient temperature
  • 36
  • [ 19417-59-5 ]
  • (E)-3-{4-[5-(2-Acetylamino-4-{5-[2-chloromethyl-5-((E)-2-cyano-2-methoxycarbonyl-vinyl)-4-methyl-1H-pyrrol-3-yl]-pentyl}-phenyl)-pentyl]-5-chloromethyl-3-methyl-1H-pyrrol-2-yl}-2-cyano-acrylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: PhCH2ONa / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating 15: SO2Cl2 / CH2Cl2 / Ambient temperature
  • 37
  • [ 19417-59-5 ]
  • [ 144582-07-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: ethanol 2: aq. KOH 3: SOCl2 / 0.5 h / Heating 4: 57 percent / SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: 80 percent / B2H6 / tetrahydrofuran 6: 86 percent / PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / 2 h / Heating 9: POCl3 / CH2Cl2 / 0.5 h 10: 76.9 percent / cyclohexylamine / toluene / 2 h / Heating 11: SO2Cl2 / CH2Cl2 / 0.5 h / Ambient temperature 12: 92 percent / acetic acid / 0.5 h / 70 °C 13: 93 percent / aq. KOH / propan-1-ol / 3 h / Heating
  • 38
  • [ 19417-59-5 ]
  • [ 144582-40-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: SOCl2 / Heating 4: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: B2H6 / tetrahydrofuran 6: PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / Heating 9: POCl3 / CH2Cl2 10: cyclohexylamine / toluene / Heating 11: SO2Cl2 / CH2Cl2 / Ambient temperature 12: acetic acid / 70 °C 13: aq. KOH / propan-1-ol / Heating
  • 39
  • [ 19417-59-5 ]
  • [ 144582-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 17 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating 15: SO2Cl2 / CH2Cl2 / Ambient temperature 16: acetic acid / 70 °C 17: aq. KOH / propan-1-ol / Heating
  • 40
  • [ 19417-59-5 ]
  • [ 144582-42-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 17 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: PhCH2ONa / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating 15: SO2Cl2 / CH2Cl2 / Ambient temperature 16: acetic acid / 70 °C 17: aq. KOH / propan-1-ol / Heating
  • 41
  • [ 19417-59-5 ]
  • [ 144582-06-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: ethanol 2: aq. KOH 3: SOCl2 / 0.5 h / Heating 4: 57 percent / SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: 80 percent / B2H6 / tetrahydrofuran 6: 86 percent / PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / 2 h / Heating 9: POCl3 / CH2Cl2 / 0.5 h 10: 76.9 percent / cyclohexylamine / toluene / 2 h / Heating 11: SO2Cl2 / CH2Cl2 / 0.5 h / Ambient temperature 12: 92 percent / acetic acid / 0.5 h / 70 °C
  • 42
  • [ 19417-59-5 ]
  • [ 144582-37-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: 1) NaOEt, 2) aq. KOH / 1) EtOH 2: dimethylformamide / Heating 3: SOCl2 / Heating 4: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 5: B2H6 / tetrahydrofuran 6: PhCH2ONa / Heating 7: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 8: dimethylformamide / Heating 9: POCl3 / CH2Cl2 10: cyclohexylamine / toluene / Heating 11: SO2Cl2 / CH2Cl2 / Ambient temperature 12: acetic acid / 70 °C
  • 43
  • [ 19417-59-5 ]
  • [ 144582-38-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1: ethanol 2: aq. KOH 3: TsOH / toluene 4: NaNO2, CF3CO2H 5: aq. KOH 6: SOCl2 / Heating 7: SnCl4 / CH2Cl2; nitromethane / Ambient temperature 8: B2H6 / tetrahydrofuran 9: 90 percent / H2, NaOAc / 10percent Pd/C / tetrahydrofuran / 760 Torr 10: 75 percent / PhCH2ONa / 0.5 h / 100 °C / 12 Torr 11: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr 12: dimethylformamide / Heating 13: POCl3 / CH2Cl2 14: cyclohexylamine / toluene / Heating 15: SO2Cl2 / CH2Cl2 / Ambient temperature 16: acetic acid / 70 °C
  • 44
  • [ 4251-21-2 ]
  • [ 19417-59-5 ]
  • 45
  • [ 16323-43-6 ]
  • [ 19417-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Raney Ni, aq. KOH 2: 1) SOCl2, 2) NEt3 3: B2H6 4: HBr
Multi-step reaction with 5 steps 1: SOCl2, DMF 2: Heating 3: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 4: LiAlH4 / tetrahydrofuran / 50 - 60 °C 5: HBr / 120 - 130 °C
  • 46
  • [ 7549-44-2 ]
  • [ 19417-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 2: LiAlH4 / tetrahydrofuran / 50 - 60 °C 3: HBr / 120 - 130 °C
Multi-step reaction with 2 steps 1: ethanol; sodium / 100 - 110 °C 2: HBr / 120 - 130 °C
  • 47
  • [ 35288-49-4 ]
  • [ 19417-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Heating 2: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 3: LiAlH4 / tetrahydrofuran / 50 - 60 °C 4: HBr / 120 - 130 °C
  • 48
  • [ 19417-59-5 ]
  • [ 105-53-3 ]
  • 1,4-bis(4,4-diethoxycarbonylbutyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol R.11 1,4-Bis(4,4-diethoxycarbonylbutyl)benzene REFERENCE EXAMPLE 11 1,4-Bis(4,4-diethoxycarbonylbutyl)benzene First, to 483 mg of metallic sodium dissolved in 21 ml of absolute ethanol, 6.72 g of diethyl malonate was added dropwise, and the mixture was refluxed for 5 minutes. After cooling, to the solution was added dropwise a mixture of 3.2 g of 1,4-bis(3-bromopropyl)benzene and diethyl malonate over 5 minutes, and the mixture was refluxed for 40 minutes to obtain a white suspension. After cooling and addition of 21 ml of ice water, the mixture was adjusted to pH 7.0 with 1N hydrochloric acid, and ethanol was removed under a reduced pressure to obtain an aqueous layer, which was then twice extracted with 100 ml of benzene each time. The extract was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated under a reduced pressure to remove the solvent, and then to remove any unreacted diethyl malonate under a reduced pressure at 140° C. to obtain 4.74 g of the title compound as a colorless liquid. 1 H--NMR (CDCl3, δ ppm): 1.25 (12H, t, J=7.1 Hz), 1.5-1.7 (4H, m), 1.8-2.0 (4H, m), 2.60 (4H, t, J=7.7 Hz), 3.33 (2H, t, J=7.4 Hz), 4.18 (8H, q, J=7.1 Hz), 7.07 (4H, s).
  • 49
  • [ 19417-59-5 ]
  • [ 7159-52-6 ]
YieldReaction ConditionsOperation in experiment
With dimethyl amine In ethanol; benzene R.9 1,4-Bis(3-dimethylaminopropyl)benzene REFERENCE EXAMPLE 9 1,4-Bis(3-dimethylaminopropyl)benzene To 1.60 g of 1,4-bis(3-bromopropyl)benzene were added 2.62 ml of ethanol and then 2.62 ml of 50% dimethylamine aqueous solution, and the mixture was stirred at a room temperature overnight. The resulting colorless solution was diluted with 50 ml of benzene, washed with 5% sodium bicarbonate aqueous solution, twice with water and then with a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure to obtain 960 mg of the title compound as a colorless liquid. 1 H--NMR (CDCl3, δ ppm): 1.77 (4H, m), 2.22 (12H, s), 2.29 (4H, t, J=7.3 Hz), 2.60 (4H, t, J=7.8 Hz), 7.10 (4H, s).
  • 50
  • [ 19417-59-5 ]
  • [ 109-89-7 ]
  • [ 7119-43-9 ]
YieldReaction ConditionsOperation in experiment
In ethanol; water; benzene R.10 1,4-Bis(3-diethylaminopropyl)benzene REFERENCE EXAMPLE 10 1,4-Bis(3-diethylaminopropyl)benzene To 1.60 g of 1,4-bis(3-bromopropyl)benzene were added 3.66 ml of ethanol, 1.83 ml of water and 1.83 g of diethylamine, and the mixture was stirred for 2 hours at 80° C. to obtain a homogeneous pale brown solution. It was then diluted with 50 ml of benzene, sequentially washed with 5% sodium bicarbonate aqueous solution, twice with water and a saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated under a reduced pressure to obtain 1.23 g of the title compound as a pale yellow liquid. 1 H--NMR (CDCl3, δ ppm): 1.00 (12H, t, J=7.2 Hz), 1.7-1.9 (4H, m), 2.4-2.7 (16H, m), 7.10 (4H, s).
  • 51
  • [ 19417-59-5 ]
  • [ 97-62-1 ]
  • C24H38O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: Ethyl isobutyrate With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h; Inert atmosphere; Stage #2: 1,4-bis-(3-bromopropyl)-benzene With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; Inert atmosphere; 11 1,4-Bis(4-ethoxycarboxy-4-methylpentyl)benzene (C5) Under N2-atmosphere, to a solution of ethyl isobutyrate (9.0 g, 77.5 mmol) in anhydrous THF (300 mL) was added dropwise lithium diisopropylamide (1.8 M solution in heptane/THF/EtPh, 46.7 mL, 84.0 mmol) at -78° C. After 1 h, a solution of 1,4-bis(3-bromopropyl)benzene (11.6 g, 36.3 mmol) in anhydrous THF (70 mL) was added dropwise, followed by the addition of DMPU (20 mL). The reaction mixture was allowed to warm to room temperature overnight, then cooled with an ice-bath, and hydrolyzed with saturated NH4Cl solution (100 mL). Water (100 mL) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (2*50 mL). The combined organic layers were washed with saturated NaCl solution (100 mL), dried with MgSO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel (EtOAc:hexanes, 1:10) to give 1,4-bis(4-ethoxycarboxy-4-methylpentyl)benzene (13.3 g, 94%) as a colorless oil. 1H NMR (CDCl3): δ=7.09 (s, 4 H), 4.11 (q, J=7.1 Hz, 4 H), 2.57 (m, 4 H), 1.57 (m, 8 H), 1.24 (t, J=7.1 Hz, 6 H), 1.47 (s, 12 H). 13C NMR (CDCl3): δ=177.9, 139.6, 128.2, 60.1, 42.0, 40.2, 35.8, 26.8, 25.1, 14.2. HRMS calcd for C24H39O4 (MH+): 391.2838, found: 391.2836.
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