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[ CAS No. 30434-64-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 30434-64-1
Chemical Structure| 30434-64-1
Chemical Structure| 30434-64-1
Structure of 30434-64-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 30434-64-1 ]

CAS No. :30434-64-1 MDL No. :MFCD09701445
Formula : C7H10O Boiling Point : -
Linear Structure Formula :- InChI Key :XSOSLVVAKBKYRV-UHFFFAOYSA-N
M.W : 110.15 Pubchem ID :121710
Synonyms :

Calculated chemistry of [ 30434-64-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.57
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 33.38
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 0.78
Log Po/w (WLOGP) : 1.54
Log Po/w (MLOGP) : 1.24
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 1.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.01
Solubility : 10.7 mg/ml ; 0.0967 mol/l
Class : Very soluble
Log S (Ali) : -0.72
Solubility : 21.0 mg/ml ; 0.191 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.39
Solubility : 4.5 mg/ml ; 0.0408 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.07

Safety of [ 30434-64-1 ]

Signal Word:Danger Class:3
Precautionary Statements:P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235 UN#:1993
Hazard Statements:H315-H319-H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 30434-64-1 ]

* 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 [ 30434-64-1 ]

[ 30434-64-1 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 2049-86-7 ]
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  • 3
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  • 4
  • [ 30434-64-1 ]
  • [ 19550-73-3 ]
  • 5
  • [ 917-64-6 ]
  • [ 30434-64-1 ]
  • 1,3,4-Trimethyl-cyclopent-2-enol [ No CAS ]
  • 6
  • [ 6284-46-4 ]
  • [ 30434-64-1 ]
YieldReaction ConditionsOperation in experiment
84.7% With PPA; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; (2) Synthesis of 3,4-dimethyl-2-cyclopentenone 1 L of polyphosphoric acid was added into a 2 L flask, purged with nitrogen, and then refluxed and stirred at 100 C., after which crotonic acid isopropyl ester (76.9 g, 0.6 mol) was slowly added in droplets thereto, and the mixture was stirred for 3 hours and thus turned into dark brown. The mixture thus obtained was mixed with ice water (500 mL) and then neutralized with sodium carbonate, after which the organic layer was extracted with ethylether and then subjected to vacuum distillation (105 C., 40 torr), thus obtaining 56 g (0.51 mol, yield 84.7%) of 3,4-dimethyl-2-cyclopentenone as a colorless transparent liquid. 1H-NMR (CDCl3) delta=1.05~1.09 (d, 3H), 1.83~1.87 (q, 1H), 1.98 (s, 3H), 2.45~2.51 (q, 1H), 2.67~2.70 (m, 1H), 5.73 (s, 1H) ppm
54% With PPA; at 100℃; for 2h; [0124] 811 g of polyphosphoric acid (Fluka 81340) was loaded to a round bottom flask equipped with a reflux condenser and a magnetic stirrer bar and heated to 100 C. 104 g (810 mmol) of isopropylcrotonate was added to the flask and the mixture was stirred for2 hours at 100 C. The resulted mixture was poured to >>1,5 kg of crushed ice. At room temperature the mixture was saturated with NH4Cl and extracted with 4×100 mL of ether. The combined ether fractions were dried over MgSO4 and filtered. Solvent was removed under reduced pressure and the remainder distilled (0.2 mbar, 33 C., bath 90 C.) to give 47.99 g of 3,4-dimethylcyclopentenone. Yield 54%. 1H-NMR (CDCl3): 5.86 (s, 1H), 2.80 (m, 1H), 2.64 (dd, 1H), 2.07 (s, 3H), 2.00 (dd, 1H), 1.18 (d, 3H).
  • 7
  • [ 106-38-7 ]
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  • 8
  • [ 106-37-6 ]
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  • [ 111690-90-5 ]
  • 9
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  • [ 81715-29-9 ]
  • 11
  • [ 62535-33-5 ]
  • [ 22748-16-9 ]
  • [ 30434-64-1 ]
  • [ 76803-46-8 ]
  • 12
  • [ 30434-64-1 ]
  • [ 107-21-1 ]
  • [ 78978-47-9 ]
  • 13
  • [ 30434-64-1 ]
  • [ 372-09-8 ]
  • 3,4-Dimethylcyclopentadienylideneacetonitrile [ No CAS ]
  • 14
  • [ 30434-64-1 ]
  • [ 95-92-1 ]
  • (2,3-Dimethyl-5-oxo-cyclopent-3-enyl)-oxo-acetic acid ethyl ester [ No CAS ]
  • 15
  • [ 30434-64-1 ]
  • [ 38693-66-2 ]
  • 16
  • [ 71718-46-2 ]
  • [ 30434-64-1 ]
  • 17
  • [ 30434-64-1 ]
  • [ 594-19-4 ]
  • 1,2-dimethyl-4-(t-butyl)cyclopentadiene [ No CAS ]
  • 18
  • [ 27607-77-8 ]
  • [ 30434-64-1 ]
  • (3,4-Dimethyl-cyclopenta-1,4-dienyloxy)-trimethyl-silane [ No CAS ]
  • 19
  • [ 30434-64-1 ]
  • [ 79271-56-0 ]
  • [ 183385-10-6 ]
  • 20
  • [ 30434-64-1 ]
  • [ 80522-42-5 ]
  • [ 183385-32-2 ]
  • 21
  • [ 75-77-4 ]
  • [ 30434-64-1 ]
  • [ 6921-34-2 ]
  • ((3R,4S)-3-Benzyl-3,4-dimethyl-cyclopent-1-enyloxy)-trimethyl-silane [ No CAS ]
  • ((3R,4R)-3-Benzyl-3,4-dimethyl-cyclopent-1-enyloxy)-trimethyl-silane [ No CAS ]
  • 22
  • [ 30434-64-1 ]
  • [ 16291-32-0 ]
  • [ 198490-79-8 ]
  • 23
  • [ 2786-02-9 ]
  • [ 30434-64-1 ]
  • [ 242149-20-8 ]
  • 24
  • [ 2786-07-4 ]
  • [ 30434-64-1 ]
  • 1-(thien-2-yl)-3,4-dimethylcyclopentadiene [ No CAS ]
  • 25
  • [ 30434-64-1 ]
  • [ 917-54-4 ]
  • [ 4784-94-5 ]
  • 26
  • [ 30434-64-1 ]
  • [ 1493-23-8 ]
  • 1-(3,4-Dimethyl-cyclopenta-1,3-dienyl)-4-fluoro-benzene [ No CAS ]
  • 27
  • [ 30434-64-1 ]
  • [ 591-51-5 ]
  • [ 51207-04-6 ]
  • 28
  • [ 214116-28-6 ]
  • [ 30434-64-1 ]
  • 31
  • [ 201230-82-2 ]
  • 2,3-dimethylbuta-1,3-diene*Fe(CO)3 [ No CAS ]
  • [ 30434-64-1 ]
  • 32
  • [ 75-77-4 ]
  • [ 30434-64-1 ]
  • (CH3)2CuLi [ No CAS ]
  • [ 192752-52-6 ]
  • 33
  • [ 75-77-4 ]
  • [ 30434-64-1 ]
  • Ph2CuLi [ No CAS ]
  • ((3S,4R)-3,4-Dimethyl-3-phenyl-cyclopent-1-enyloxy)-trimethyl-silane [ No CAS ]
  • 34
  • [ 75-77-4 ]
  • [ 30434-64-1 ]
  • (CH2=CH)2CuLi [ No CAS ]
  • ((3S,4R)-3,4-Dimethyl-3-vinyl-cyclopent-1-enyloxy)-trimethyl-silane [ No CAS ]
  • C12H22OSi [ No CAS ]
  • 35
  • [ 2786-02-9 ]
  • [ 30434-64-1 ]
  • 1-furyl-3,4-dimethylcyclopentadiene [ No CAS ]
  • 36
  • [ 30434-64-1 ]
  • [ 2786-03-0 ]
  • 2-(3,4-dimethyl-cyclopenta-2,4-dienyl)-benzofuran [ No CAS ]
  • 37
  • [ 30434-64-1 ]
  • [ 114173-77-2 ]
  • [5-(3,4-dimethyl-cyclopenta-2,4-dienyl)-furan-2-yl]-trimethyl-silane [ No CAS ]
  • 38
  • [ 30434-64-1 ]
  • [ 54783-53-8 ]
  • 2-(3,4-dimethyl-cyclopenta-2,4-dienyl)-5-methyl-furan [ No CAS ]
  • 39
  • [ 30434-64-1 ]
  • [ 591-51-5 ]
  • (3,4-dimethyl-cyclopenta-2,4-dienyl)-benzene [ No CAS ]
  • 40
  • [ 3141-27-3 ]
  • [ 30434-64-1 ]
  • [ 460740-77-6 ]
  • 42
  • [ 92-66-0 ]
  • [ 30434-64-1 ]
  • 1-biphenyl-3,4-dimethylcyclopentadiene [ No CAS ]
  • 43
  • Acetic acid (E)-1-ethynyl-2-methyl-but-2-enyl ester [ No CAS ]
  • [ 30434-64-1 ]
  • 44
  • 2,2-Dimethyl-propionic acid (E)-1-ethynyl-2-methyl-but-2-enyl ester [ No CAS ]
  • [ 30434-64-1 ]
  • 45
  • Benzoic acid (E)-1-ethynyl-2-methyl-but-2-enyl ester [ No CAS ]
  • [ 30434-64-1 ]
  • 46
  • [ 30434-64-1 ]
  • (Z)-3,4,3',4'-Tetramethyl-bicyclopentylidene-2,2'-diene [ No CAS ]
  • (E)-3,4,3',4'-Tetramethyl-bicyclopentylidene-2,2'-diene [ No CAS ]
  • 47
  • [ 30434-64-1 ]
  • [ 586-77-6 ]
  • 1-(4-dimethylamino-phenyl)-3,4-dimethyl-cyclopent-2-enol [ No CAS ]
  • 48
  • [ 30434-64-1 ]
  • [4-(3,4-dimethyl-cyclopenta-1,3-dienyl)-phenyl]-dimethyl-amine [ No CAS ]
  • 49
  • [ 30434-64-1 ]
  • bis-(5-furan-2-yl-2,3-dimethyl-cyclopenta-1,3-dienyl)-dimethyl-silane [ No CAS ]
  • 50
  • [ 30434-64-1 ]
  • bis-(2,3-dimethyl-5-phenyl-cyclopenta-1,3-dienyl)-dimethyl-silane [ No CAS ]
  • 51
  • [ 30434-64-1 ]
  • bis-[2,3-dimethyl-5-(5-methyl-furan-2-yl)-cyclopenta-1,3-dienyl]-dimethyl-silane [ No CAS ]
  • 52
  • [ 30434-64-1 ]
  • bis-(5-benzofuran-2-yl-2,3-dimethyl-cyclopenta-1,3-dienyl)-dimethyl-silane [ No CAS ]
  • 53
  • [ 30434-64-1 ]
  • C30H44O2Si3 [ No CAS ]
  • 55
  • [ 30434-64-1 ]
  • [ 198490-80-1 ]
  • 56
  • [ 30434-64-1 ]
  • (2S,4R)-2-Hydroxy-3,3,4-trimethyl-cyclopentanone [ No CAS ]
  • 57
  • [ 30434-64-1 ]
  • [ 79848-83-2 ]
  • 58
  • [ 30434-64-1 ]
  • (E)-3,4,4-Trimethyl-octa-5,7-dienoic acid methyl ester [ No CAS ]
  • 59
  • [ 30434-64-1 ]
  • (3R,4S)-4-Formyl-3,4-dimethyl-hex-5-enoic acid methyl ester [ No CAS ]
  • 60
  • [ 30434-64-1 ]
  • (2R,3R,4S)-2-Hydroxy-3,4-dimethyl-3-vinyl-cyclopentanone [ No CAS ]
  • 61
  • [ 30434-64-1 ]
  • (E)-(3R,4S)-3,4-Dimethyl-4-vinyl-octa-5,7-dienoic acid methyl ester [ No CAS ]
  • 62
  • [ 30434-64-1 ]
  • (2R,3R,4S)-3-Benzyl-2-hydroxy-3,4-dimethyl-cyclopentanone [ No CAS ]
  • 63
  • [ 30434-64-1 ]
  • (2S,3R,4R)-2-Hydroxy-3,4-dimethyl-3-phenyl-cyclopentanone [ No CAS ]
  • 64
  • [ 30434-64-1 ]
  • (3S,4R)-4-Formyl-3,4-dimethyl-5-phenyl-pentanoic acid methyl ester [ No CAS ]
  • 65
  • [ 30434-64-1 ]
  • (E)-(3S,4R)-4-Benzyl-3,4-dimethyl-octa-5,7-dienoic acid methyl ester [ No CAS ]
  • 66
  • [ 30434-64-1 ]
  • (3R,4R)-3,4-Dimethyl-5-oxo-4-phenyl-pentanoic acid methyl ester [ No CAS ]
  • 67
  • [ 30434-64-1 ]
  • (E)-(3R,4S)-3,4-Dimethyl-4-phenyl-octa-5,7-dienoic acid methyl ester [ No CAS ]
  • 68
  • [ 30434-64-1 ]
  • 3,4-Dimethyl-5-methylene-cyclopent-2-enone [ No CAS ]
  • 69
  • [ 30434-64-1 ]
  • 1-(2-Aminoethyl)-3,4-dimethylcyclopenta-1,3-diene [ No CAS ]
  • 70
  • [ 30434-64-1 ]
  • N-<2-(3,4-Dimethylcyclopenta-1,3-dienyl)ethyl>aza-12-crown-4 [ No CAS ]
  • 71
  • [ 30434-64-1 ]
  • N,N'-Bis<2-(3,4-dimethylcyclopenta-1,3-dienyl)ethyl>-1,13-diaza-24-crown-8 [ No CAS ]
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  • [ 78978-49-1 ]
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  • [ 30434-64-1 ]
  • [ 78978-48-0 ]
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  • [ 30434-64-1 ]
  • [ 4045-51-6 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; lithium aluminum hydride; In diethyl ether; water; (3) Synthesis of tert-butyl-1-(3,4-dimethylcyclopentadienyl)-1,1-dimethylsilaneamine In a nitrogen atmosphere, lithium aluminum hydride (6.07 g, 0.16 mol) was dissolved in diethylether (250 mL), and <strong>[30434-64-1]3,4-dimethyl-2-cyclopentenone</strong> (33.95 g, 0.31 mol) was slowly added in droplets thereto at 0 C. Refluxing for 30 minutes and cooling to 0 C. via room temperature were performed, after which distilled water (15 mL) was slowly added in droplets thereto and thus unreacted lithium aluminum hydride was removed. The reaction mixture was slowly added to dilute sulfuric acid and the organic layer was extracted with diethylether and then subjected to vacuum distillation, thus obtaining 21.2 g of 2,3-dimethylcyclopentadiene as a yellow liquid.
Me2SiCl2 (7.03g, 54.5mmol) was slowly added to 1,2-dimethyl cyclopentadienyl lithium (5.45g, 54.5mmol), which was prepared from compounds 1 and 2 in ether solution at -78C. The volatiles were removed under reduced pressure after stirring the reaction mixture at room temperature overnight. The residue was extracted with pentane (50mL×3). Removal of solvent followed by distillation gave a light yellow oil of 3 (6.35g, 62.4%) as a mixture of isomers. 1H NMR (C6D6) delta: 6.051 (2H, s, Cp-(H)2), 1.822 (6H, s, Cp-(CH3)2), 0.097 (6H, s, Si-(CH3)2).
  • 79
  • [ 30434-64-1 ]
  • [ 69739-34-0 ]
  • t-butyldimethylsiloxy-3,4-dimethylcyclopentadienes; mixture of isomers [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine; In pentane; at 20℃; for 2.5h; [0125] 12.23 g (111.0 mmol) of <strong>[30434-64-1]3,4-dimethylcyclopentenone</strong>, 11.31 g (111.8 mmol) of triethylamine dried with molecular sieves and 300 mL of dry pentane were mixed at room temperature. During 13 minutes 29.44 g (111.4 mmol) of t-butyldimethylsilyltrifluoromethylsulfonate (Fluka 97742) was added to the mixture. After strirring for 2.5 hour the supernatant pentane fraction was separated, solvent removed under reduced pressure and the remainder distilled (0.03 mbar, 34-40 C., bath 100 C.) resulting in 19.74 g of isomer isomer mixture of t-butyldimethylsiloxy-3,4-dimethylcyclopentadienes. Yield 79%. 1H-NMR spectrum was complicated due to presence of at least 3 isomers. The product was characterised by GC/MS technique, which showed presence of three components (GC) each showing M+ peak at 224 (MS).
  • 80
  • tetrakis(dimethylamido)titanium(IV) [ No CAS ]
  • [ 30434-64-1 ]
  • 1-dimethylamino-3,4-dimethylcyclopentadiene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; at -78 - 20℃; Under nitrogen atmosphere, after a solution of <strong>[30434-64-1]3,4-dimethylcyclopentenone</strong> (15.0 mmol) in toluene (10.0 mL) was cooled to -78C, a solution of tetrakisdimethylaminotitanium (7.8 mmol) in toluene(8.3 mL) was added dropwise and the mixture was stirred at room temperature. After disappearance of ketone from the reaction mixture was confirmed by gas chromatography, the solvent was distilled off under reduced pressure. Hexane (18.3 mL) was added and a precipitated solid was separated by filtration. The filtrate was concentrated to obtain 1-dimethylamino-3,4-dimethylcyclopentadiene (2.23 g) as an oil. The oil was added to hexane (30.0 mL) without being purified and cooled to -78C. A 1.59 M solution of n-butyl lithium in hexane (15.0 mmol) was added dropwise. The mixture was warmed to room temperature and stirred for 4 hours. A formed solid was separated by filtration and dried to obtain 1-dimethylamino-3,4-dimethylcyclopentadienyllithium (0.63 g, 29.6%) as flesh powder.1H-NMR (deuterated chloroform, delta(ppm)): 1.86(3H), 1.90(3H), 2.41(6H), 2.66(2H), 4.94(1H) Mass spectra(EI, m/z): 137 (M+), 122, 77 A solution of (2-allyloxy-3-tert-butyl-5-methylphenyl)dimethylchlorosilane (7.0 mmol) in toluene (12.1 mL) was added dropwise to a solution of 1-dimethylamino-3,4-dimethylcyclopentadienyllithium (7.0 mmol) in tetrahydrofuran (10.5 mL) and the mixture was stirred at room temperature for 6 hours. After the solvent was distilled off under reduced pressure, dehydrated pentane was added and a precipitated solid was filtered off. The filtrate was concentrated to obtain the title compound (2.86 g, 100%) as an oil.1H-NMR (deuterated benzene, delta(ppm)): 0.36(3H), 0.59(3H), 1.71(9H), 1.90(3H), 2.21(3H), 2.44(6H), 3.67(1H), 4.40-4.47(2H), 5.10-5.14(1H), 5.27(1H), 5.54-5.60(1H), 5.79-5.88(1H), 7.24(1H), 7.28(1H) Mass spectra(EI, m/z): 397 (M+), 382, 340, 261, 136
  • 81
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  • [ 30434-64-1 ]
  • [ 242149-20-8 ]
YieldReaction ConditionsOperation in experiment
51% With hydrogenchloride; n-butyllithium; sodium sulfate; In diethyl ether; hexane; water; (a1) Synthesis of 1-(2-furyl)-3,4-dimethylcyclopentadiene A 1 l glass reaction vessel was charged with 21.0 g (0.31 mol) of furan and 400 ml of diethyl ether and cooled to -30 C. on a dry ice/methanol bath. To the mixture were added dropwise 200 ml (0.31 mmol) of an n-butyllithium/hexane solution of 1.53 mol/l. After the addition was completed, the mixture was raised to room temperature and stirred for 4 hrs. The mixture was again cooled to -30 C. on a dry ice/methanol bath and 100 ml of a diethyl ether solution containing 33.0 g (0.30 mol) of 3,4-dimethylcyclopenten-1-one were added dropwise. After the addition was completed, the mixture was returned to room temperature and stirred for 16 hrs. To the reaction solution was added distilled water, this solution was transferred into a separatory funnel and washed three times with brine. Subsequently, the solution was shaken twice with 50 ml of 5N hydrochloric acid and washed with brine until it was neutral. Anhydrous sodium sulfate was added and the solution was allowed to stand overnight and dried. Anhydrous sodium sulfate was filtered off and the solvent was distilled off under reduced pressure. Purification of the residue with a silica gel column gave 24.6 g (51% yield) of 1-(2-furyl)-3,4-dimethylcyclopentadiene as a red liquid. The structure was identified by NMR.
51% With hydrogenchloride; n-butyllithium; sodium sulfate; In diethyl ether; hexane; water; (a1) Synthesis of 1-(2-furyl)-3,4-dimethyl-cyclopentadiene A 1 l glass reaction vessel was charged with 21.0 g (0.31 mol) of furan and 400 ml of diethyl ether and cooled to -30 C. on a dry ice/methanol bath. To the mixture were added dropwise 200 ml (0.31 mmol) of an n-butyllithium/hexane solution of 1.53 mol/l. After the addition was completed, the mixture was raised to room temperature and stirred for 4 hrs. The mixture was again cooled to -30 C. on a dry ice/methanol bath and 100 ml of a diethyl ether solution containing 33.0 g (0.30 mol) of 3,4-dimethyl-cyclopenten-1-one were added dropwise. After the addition was completed, the mixture was returned to room temperature and stirred for 16 hrs. To the reaction solution was added distilled water, this solution was transferred into a separatory funnel and washed three times with brine. Subsequently, the solution was shaken twice with 50 ml of 5N hydrochloric acid and washed with a brine until it was neutral. Anhydrous sodium sulfate was added and the solution was allowed to stand overnight and dried. Anhydrous sodium sulfate was filtered off and the solvent was distilled off under reduced pressure. Purification of the residue with a silica gel column gave 24.6 g (51% yield) of 1-(2-furyl)-3,4-dimethyl-cyclopentadiene as a red liquid. The structure was identified by NMR.
  • 82
  • [ 271-89-6 ]
  • [ 30434-64-1 ]
  • [ 285986-46-1 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride; n-butyllithium; sodium sulfate; In tetrahydrofuran; hexane; water; (a1) Synthesis of 1-(2-benzofuryl)-3,4-dimethylcyclopentadiene A 1 l glass reaction vessel was charged with 34.4 g (0.29 mol) of benzofuran and 400 ml of THF and the mixture was cooled to -70 C. on a dry ice/methanol bath. To the mixture were added dropwise 180 ml (0.28 mol) of an n-butyllithium/hexane solution of 1.53 mol/l. After the addition was completed, the mixture was raised to room temperature and stirred for 16 hrs. The mixture was again cooled to -30 C. on a dry ice/methanol bath and 100 ml of a THF solution containing 30.0 g (0.27 mol) of 3,4-dimethylcyclopenten-1-one were added dropwise. After the addition was completed, the mixture was raised to room temperature and stirred for 16 hrs. To the reaction solution was added distilled water. This reaction solution was transferred into a separatory funnel and washed three times with brine. This solution was then shaken twice with 30 ml of 2N hydrochloric acid and washed with brine until it was neutral. Anhydrous sodium sulfate was added and the reaction solution was allowed to stand overnight and dried. Anhydrous sodium sulfate was filtered off and the solvent was distilled off under reduced pressure. Purification of the residue by a silica gel column gave 54.3 g (95% yield) of 1-(2-benzofuryl)-3,4-dimethylcyclopentadiene as pale yellow crystals. The structure was identified by NMR.
  • 83
  • [ 30434-64-1 ]
  • 1-(thien-2-yl)-3,4-dimethylcyclopentadiene [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride; n-butyllithium; sodium sulfate; In tetrahydrofuran; thiophene; hexane; water; (a1) Synthesis of 1-(2-thienyl)-3,4-dimethylcyclopentadiene A 1 l glass reaction vessel was charged with 25.3 g (0.30 mol) of thiophene and 350 ml of THF and the mixture was cooled to -70 C. on a dry ice/methanol bath. To the mixture were added dropwise 200 ml (0.30 mol) of an n-butyllithium/hexane solution of 1.52 mol/l. After the addition was completed, the mixture was raised to room temperature and stirred for 16 hrs. The mixture was again cooled to -30 C. on a dry ice/methanol bath and 100 ml of a THF solution containing 33.0 g (0.30 mol) of 3,4-dimethylcyclopenten-1-one were added dropwise. After the addition was completed, the mixture was raised to room temperature and stirred for 16 hrs. To the reaction solution was added distilled water. This solution was transferred into a separatory funnel and washed three times with brine. Subsequently, the solution was shaken twice with 50 ml of 5N hydrochloric acid and washed with brine until it was neutral. Anhydrous sodium sulfate was added and the solution was allowed to stand overnight and dried. Anhydrous sodium sulfate was filtered off and the solvent was distilled off under reduced pressure. Purification of the residue by a silica gel column gave 49.7 g (94% yield) of 1-(2-thienyl)-3,4-dimethyl-cyclopentadiene as a yellow solid. The structure was identified by NMR.
  • 84
  • [ 104-95-0 ]
  • [ 30434-64-1 ]
  • [ 1001098-37-8 ]
  • 85
  • [ 30434-64-1 ]
  • [ 586-77-6 ]
  • [4-(3,4-dimethyl-cyclopenta-1,3-dienyl)-phenyl]-dimethyl-amine [ No CAS ]
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