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[ CAS No. 123-35-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 123-35-3
Chemical Structure| 123-35-3
Chemical Structure| 123-35-3
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Quality Control of [ 123-35-3 ]

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Product Details of [ 123-35-3 ]

CAS No. :123-35-3 MDL No. :MFCD00008908
Formula : C10H16 Boiling Point : -
Linear Structure Formula :CH2CHCCH2CH2CH2CHC(CH3)2 InChI Key :UAHWPYUMFXYFJY-UHFFFAOYSA-N
M.W : 136.23 Pubchem ID :31253
Synonyms :
β-Myrcene;NSC 406264
Chemical Name :7-Methyl-3-methyleneocta-1,6-diene

Calculated chemistry of [ 123-35-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.76
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -4.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.89
Log Po/w (XLOGP3) : 4.17
Log Po/w (WLOGP) : 3.48
Log Po/w (MLOGP) : 3.56
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 3.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.122 mg/ml ; 0.000896 mol/l
Class : Soluble
Log S (Ali) : -3.88
Solubility : 0.018 mg/ml ; 0.000132 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.42
Solubility : 0.524 mg/ml ; 0.00385 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.85

Safety of [ 123-35-3 ]

Signal Word:Danger Class:3
Precautionary Statements:P301+P310-P305+P351+P338-P331 UN#:2319
Hazard Statements:H226-H304-H315-H319-H350-H360 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 123-35-3 ]

* 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 [ 123-35-3 ]

[ 123-35-3 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 108-31-6 ]
  • [ 123-35-3 ]
  • [ 29811-04-9 ]
YieldReaction ConditionsOperation in experiment
91.85% at 55 - 70℃; for 4h;
at 50 - 230℃; Inert atmosphere; 2 Myrcene/Maleic Anhydride Diels-Alder Adduct Maleic Anhydride (67.6 g/0.69 mole) and betamyrcene (95.6 g/0.70 mole) were added to a 250 mE, three- neck, round bottom flask equipped with a heating mantle, magnetic stirring, thermocouple nitrogen purge and condenser. The mixture was heated to 50° C., when the appearance of the mixture changed from opalescent to transparent and an exotherm resulted in a temperature spike to about 230° C. Vigorous reflux occurred. The heating mantle was removed and the stirred mixture allowed to cool to room temperature. Gel phase permeation chromatography indicated that the product is the Diels-Alder adduct of myrcene and maleic anhydride.
In tetrahydrofuran at 100℃; for 0.0833333h; Microwave irradiation; Batch Diels-Alder reaction General procedure: The following procedure is typical for the preparation of theDiels-Alder adduct of myrcene (1) and a series of differentdienophiles. A reactant solution of myrcene (1, 811 mg ofmyrcene stock solution with a 90% purity, 5.36 mmol ofmyrcene), 2b (429 mg, 5.95 mmol), in EtOAc (0.49 mL), waspremixed and filled into a sealed microwave vial. The reactionwas conducted in a laboratory microwave reactor (Biotage Initiator) at 140 °C with a reaction time of 2 h. A transparent, faintlyyellow solution was obtained after reaction, from which theconversion was determined by 1H NMR. The solvent was evaporated under reduced pressure to yield a yellow semi-crystalline paste. Detailed reaction conditions and reagent compositions for each batch experiment can be found in Table 1 andTable 2. For kinetic studies, small samples of the reaction mixture for 1H NMR were withdrawn through the septum of themicrowave reactor glass vial using a syringe. For this the microwave reaction was stopped at various points in time over thecourse of the reaction, namely at 20, 40, 60 and 120 min.
at 50 - 70℃; for 3h; 1 step 2; Maleic anhydride was added to a four-necked flask 100 (see Figure 1) equipped with a heating mantle, stirrer 1, thermometer 2, dropping funnel, and reflux condenser pipe 3 and heated to melt it, where in condenser pipe 3 was connected with a drying tube containing CaCl2. The stirrer 1 started to stir the maleic anhydride in the four-necked flask 100, the temperature was maintained at 50°C-60°C, and the equimolar β-myrcene of maleic anhydride was added dropwise from the dropping funnel, the control was completed within 0.5h, and after the addition was completed, the temperature was raised to 70°C for 3h, at the end of the reaction, vacuum distillation was used to collect the fraction at 180°C/1.05 kPa (absolute pressure) as an intermediate product named 4-(4-methyl-3-pentenyl)-4-cyclohexene-1,2- acid anhydride (abbreviated as MYM).

  • 3
  • [ 123-35-3 ]
  • [ 22035-53-6 ]
  • [ 133475-88-4 ]
YieldReaction ConditionsOperation in experiment
41% With aluminium trichloride In chloroform at 62℃; for 18h;
  • 4
  • [ 106-24-1 ]
  • [ 123-35-3 ]
YieldReaction ConditionsOperation in experiment
25% With copper(II) sulfate In neat (no solvent) at 125℃; for 1.5h;
Multi-step reaction with 3 steps 1: 86 percent 2: NaI / acetone / 1 h / 0 - 2 °C 3: triethylamine / hexane / 6 h / 25 °C / Irradiation
With bis(acetylacetonato)palladium(II); carbon monoxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid In toluene at 105℃; for 18h; chemoselective reaction;
Multi-step reaction with 2 steps 1: Castellaniella defragrans linalool dehydratase isomerase / 20 h / Enzymatic reaction 2: Castellaniella defragrans linalool dehydratase isomerase / 20 h / Enzymatic reaction
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C 2: potassium <i>tert</i>-butylate; 18-crown-6 ether / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere
With palladium diacetate; acetic acid; Tri(p-tolyl)phosphine In hexane at 70℃; for 6h; Inert atmosphere; 2 [Example 2] Under inert gas atmosphere, add 154g geraniol, 60g acetic acid and 70g n-hexane to the there-necked flask, and the there-necked flask is equipped with a water separator and a condenser. Add 1.12g palladium acetate and 7.61g tris(p-methylphenyl)phosphine to the there-necked flask, stir and heat the system to n-hexane and reflux occurs, the temperature in the there-necked flask rises to 70°C, the water phase appears in the water separator, heat After maintaining reflux for 6h, it was cooled to room temperature.The water separator produced water and n-hexane totaled 36.56g,Take the reaction solution in the three-necked bottle to detect the mass content of the components as follows: Acetic acid 20.31%, n-hexane 20.89%, myrcene 48.98%, terpinene 1.14%, limonene 4.07%, palladium and organic phosphine 3.55%, others 1.06%. Myrcene selectivity 88.65%.

  • 5
  • [ 141-12-8 ]
  • [ 123-35-3 ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis(triphenylphosphine) palladium(0); 2-Propynylzinc bromide In tetrahydrofuran for 3h; Ambient temperature;
  • 6
  • [ 763-10-0 ]
  • [ 78-70-6 ]
  • [ 123-35-3 ]
  • [ 106-25-2 ]
  • [ 106-24-1 ]
  • [ 13877-91-3 ]
  • [ 98-55-5 ]
  • 7
  • [ 28673-26-9 ]
  • [ 78-70-6 ]
  • [ 123-35-3 ]
  • [ 106-25-2 ]
  • [ 106-24-1 ]
  • [ 98-55-5 ]
  • 8
  • [ 2565-83-5 ]
  • [ 123-35-3 ]
YieldReaction ConditionsOperation in experiment
35% With potassium <i>tert</i>-butylate In tetrahydrofuran for 7h; Heating;
  • 9
  • [ 101010-61-1 ]
  • [ 78-70-6 ]
  • [ 123-35-3 ]
  • [ 106-25-2 ]
  • [ 106-24-1 ]
  • [ 98-55-5 ]
  • [ 138-86-3 ]
  • 10
  • [ 74367-67-2 ]
  • [ 78-70-6 ]
  • [ 123-35-3 ]
  • [ 106-25-2 ]
  • [ 106-24-1 ]
  • [ 98-55-5 ]
  • [ 138-86-3 ]
  • 11
  • [ 201230-82-2 ]
  • C12H24O6*C10H17O(1-)*K(1+) [ No CAS ]
  • [ 123-35-3 ]
  • [ 105-86-2 ]
YieldReaction ConditionsOperation in experiment
at 40℃; 65-70 h; Yield given. Yields of byproduct given;
  • 12
  • [ 81678-26-4 ]
  • [ 123-35-3 ]
  • [ 60763-44-2 ]
  • [ 13877-91-3 ]
  • [ 2565-83-5 ]
  • [ 14576-08-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride for 5h; Irradiation; other alkylmercaptoazoles, var solvents and temperatures;
  • 13
  • C12H24O6*C10H17O(1-)*K(1+) [ No CAS ]
  • [ 123-35-3 ]
  • [ 105-86-2 ]
YieldReaction ConditionsOperation in experiment
With carbon monoxide at 40℃; 65-70 h; Yield given. Yields of byproduct given;
  • 15
  • [ 21806-61-1 ]
  • [ 123-35-3 ]
  • (+/-)-5-(4'-methylpenta-3'-en-1'-yl)-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]
  • (+/-)-6-(4'-methylpenta-3'-en-1'-yl)-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]
  • 16
  • [ 2565-83-5 ]
  • [ 123-35-3 ]
YieldReaction ConditionsOperation in experiment
76% In tetrahydrofuran at -50℃; for 1h;
  • 17
  • [ 126-91-0 ]
  • Japanese acid earth [ No CAS ]
  • [ 123-35-3 ]
  • [ 106-24-1 ]
  • [ 98-55-5 ]
  • [ 5989-27-5 ]
  • 19
  • [ 106-24-1 ]
  • [ 78-70-6 ]
  • [ 123-35-3 ]
  • [ 3779-61-1 ]
  • [ 98-55-5 ]
  • 20
  • [ 123-35-3 ]
  • [ 5464-77-7 ]
  • 1-(N,N-dibenzylamino)-2-ethenyl-2-(4-methylpent-3-en-1-yl)cyclopropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With titanium(IV) isopropylate; methylmagnesium chloride; cyclohexylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 16h;
  • 21
  • [ 123-35-3 ]
  • [ 697-91-6 ]
  • [ 500217-76-5 ]
  • [ 500217-72-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-methyl-3-methene-1,6-octadiene; 2,6-dichloro-1,4-benzoquinone for 0.133333h; microwave irradiation; Stage #2: With manganese(IV) oxide In benzene Heating; Title compound not separated from byproducts;
Stage #1: 7-methyl-3-methene-1,6-octadiene; 2,6-dichloro-1,4-benzoquinone With boron trifluoride diethyl etherate In diethyl ether at 20℃; for 20h; Stage #2: With manganese(IV) oxide In benzene for 72h; Heating; Title compound not separated from byproducts;
  • 22
  • [ 123-35-3 ]
  • [ 1975-78-6 ]
  • 3-(4-methyl-pent-3-enyl)-1-nonyl-cyclopent-3-enylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: 7-methyl-3-methene-1,6-octadiene With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -78 - -20℃; Stage #2: n-decanenitrile In diethyl ether at -20 - 20℃;
  • 23
  • [ 123-35-3 ]
  • [ 614-47-1 ]
  • [4-(4-methylpent-3-en-1-yl)-6-phenylcyclohex-3-en-1-yl](phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With aluminum tri-bromide In toluene at 28℃; for 6h; Inert atmosphere; diastereoselective reaction; General procedure for synthesis of panduratin A derivatives 3a-3r General procedure: A 1.0 M solution of AlBr3 in CH2Br2 (30 mol%) was added to a solution of the appropriatetrans-chalcone (1 equiv) in anhydrous toluene or CH2Cl2 (2 mL/mmol) at r.t. (28 °C) under N2. (E)-Ocimene (5 equiv) was added, and the mixture was stirred at r.t for 24 h or until all thechalcone was consumed. The mixture was then poured into ice-water acidified with 3N aqueousHCl to pH 2-3. The resulting mixture was extracted with EtOAc, and the organic phase was dried(Na2SO4) and concentrated under reduced pressure. The crude product was purified by columnchromatography (silica gel, 5-20% EtOAc-hexane). The structures of 3a-3r were confirmed by1H, 13C NMR and HRMS spectroscopic techniques.
73% With nanoporous alumosilicate In Petroleum ether at -1℃; for 70h;
  • 24
  • [ 123-35-3 ]
  • [ 22966-25-2 ]
  • (4-fluorophenyl)(4-(4-methylpent-3-enyl)-6-phenylcyclohex-3-en-1-yl)methanone [ No CAS ]
  • 25
  • [ 123-35-3 ]
  • [ 14434-41-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: CH2Cl2 / 0.17 h / 0 °C 2: 65 percent / AcOH / 1 h / 20 °C 3: 30percent H2O2, AcOH / 20 h / 20 °C 4: NaHCO3 / toluene / 1.5 h / Heating 5: 68 percent / AcOH, toluene-p-sulphonic acid / diethyl ether; H2O / 1 h / 0 °C 6: 83 percent / 10percent KOH / ethanol; H2O / 3 h / 20 °C
  • 26
  • [ 106-25-2 ]
  • [ 123-35-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 82 percent 2: NaI / acetone / 1 h / 0 - 2 °C 3: triethylamine / hexane / 6 h / 25 °C / Irradiation
With bis(acetylacetonato)palladium(II); carbon monoxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid In toluene at 105℃; for 18h; chemoselective reaction;
With palladium(II) acetylacetonate; acetic acid; triphenylphosphine In tetrahydrofuran at 69℃; for 8h; Inert atmosphere; 3 [Example 3] Under an inert gas atmosphere, add 154 g of nerol, 20 g of acetic acid and 120 g of tetrahydrofuran into a three-necked flask, and the three-necked flask is equipped with a water separator and a condenser. Add 3.04g of palladium acetylacetonate and 26.23g of triphenylphosphine to the there-necked flask, stir and heat the system until tetrahydrofuran reflux occurs, the temperature in the there-necked flask rises to 69°C, and an aqueous phase appears in the water separator, and the heating is maintained for 8 hours after refluxing. Cool to room temperature. A total of 36.23 g of water and tetrahydrofuran was produced from the water separator. The reaction liquid in the three-necked flask was taken to detect the mass contents of the components: acetic acid 6.96%, tetrahydrofuran 35.46%, myrcene 42.74%, terpinene 0.79%, limonene 2.68%, palladium and organic Phosphine 10.20%, other 1.17%. Myrcene selectivity 90.20%.
  • 27
  • [ 123-35-3 ]
  • [ 115-95-7 ]
YieldReaction ConditionsOperation in experiment
84.5% With hydrogenchloride; sodium acetate; triethylamine hydrochloride In dichloromethane; water 1 EXAMPLE 1 EXAMPLE 1 Methylene chloride (330 cc), triethylamine hydrochloride (3.33 g), cuprous chloride (2.4 g) and 69.6% pure technical-grade myrcene (164.4 g) are introduced, under an argon atmosphere, into a reactor A equipped with a magnetic stirrer. The homogeneous reaction mixture, which has an orange colour, is cooled to a temperature of about -5° C. Dry hydrogen chloride (43 g) is then introduced over the course of 5 hours. The solution obtained is then introduced in the course of a few minutes, at 20° C., into reactor B, equipped with a magnetic stirrer and kept under an argon atmosphere, which reactor contains anhydrous sodium acetate (145 g), cuprous chloride (2.4 g) and triethylamine hydrochloride (3.33 g). The temperature of the reactor B rises to 31° C. after 3 hours. Cuprous chloride (2.4 g) is then added and stirring is continued for 18 hours at 20° C. The reaction mixture is then poured onto ice (400 g). This gives an intensely blue aqueous phase and a light brown organic phase. After phase separation, the organic phase is washed with an aqueous solution (300 cc) containing ammonium chloride (100 g/liter) and then with water (twice 200 cc), and is finally dried over potassium carbonate. After filtration, and evaporation of the solvent, an oil (237.1 g) containing 59% of linalyl acetate is obtained. The yield is 84.5% relative to the pure myrcene present in the technical-grade product.
  • 28
  • PdSO4 [ No CAS ]
  • Li2 MoO4 [ No CAS ]
  • [ 123-35-3 ]
  • [ 629-50-5 ]
  • [ 7732-18-5 ]
  • [ 5392-40-5 ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-pyrrolidin-2-one; nitrogen; p-benzoquinone; lithium chloride; sodium chloride 6 EXAMPLE 6 EXAMPLE 6 To a solution of N-methylpyrrolidone (0.75 ml) and Li2 MoO4 (0.11 gm) was added PdSO4 (0.024 gm), LiCl (0.0054 gm), benzoquinone (0.03 gm) and H2 O (0.075 ml). The solution was gently but continuously stirred for about 5 minutes using nitrogen as an inert purging gas. Myrcene (0.066 ml) was added and the solution was heated to about 90° C., for about 2.5 hrs, with gentle and continuous stirring. Tridecane (0.013 gm) was then added to the mixture as an internal standard, and the solution was transferred to a separation funnel, rinsed with toluene (1.5 ml) and extracted five times using a NaCl/H2 O solution. The organic phase was then dried over K2 CO3, and the resulting product analyzed substantially as described in Example 1. The resulting yield of citral was 34%, with a selectivity of 17%.
  • 29
  • PdCl2 (CH3 CN)2 [ No CAS ]
  • Li2 MoO4 [ No CAS ]
  • [ 123-35-3 ]
  • [ 629-50-5 ]
  • [ 5392-40-5 ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-pyrrolidin-2-one; sodium chloride In water; toluene 1 EXAMPLE 1 EXAMPLE 1 To a solution of N-methylpyrrolidone (0.75 ml) and Li2 MoO4 (0.11 gm) was added PdCl2 (CH3 CN)2 (0.03 gm) and water (0.075 ml). The solution was gently but continuously stirred using a magnetic stirrer for about 5 minutes while nitrogen was employed as an inert purging gas. Myrcene (0.066 ml) was then added to the solution and the mixture was heated to about 90° C. for about 2.5 hrs, with gentle and continuous stirring. Tridecane (0.014 gm) was then added to the mixture as an internal standard, and the solution was transferred to a separation funnel. Toluene (1.5 ml) was added, and the solution was extracted five times using a NaCl/H2 O mixture. The organic phase was then dried over K2 CO3. The resulting yield of citral was 44%, with a selectivity of 26%.
  • 30
  • [ 123-35-3 ]
  • [ 123-03-5 ]
  • [ 71-36-3 ]
  • [ 5392-40-5 ]
YieldReaction ConditionsOperation in experiment
With carbon dioxide; To the solution was then added myrcene (3 ml), n-butanol (7.5 ml) and <strong>[123-03-5]cetylpyridinium chloride</strong> (0.3586 g). Carbon dioxide was bubbled through for about 20 min, the solution was heated to about 90 C. for about 2.5 hrs, and product recovered. The resulting yield of citral was 66%.
  • 31
  • [ 123-35-3 ]
  • [ 112-02-7 ]
  • [ 71-36-3 ]
  • [ 5392-40-5 ]
YieldReaction ConditionsOperation in experiment
With carbon dioxide; To the solution was then added myrcene (0.66 ml), n-butanol (7.5 ml) and <strong>[112-02-7]cetyltrimethylammonium chloride</strong> (1.32 ml). Carbon dioxide was bubbled through for about 20 min, the solution was heated to about 90 C. for about 2.5 hrs, and product recovered. The resulting yield of citral was 46%.
With oxygen; To the solution was then added myrcene (3 ml), n-butanol (7.5 ml) and <strong>[112-02-7]cetyltrimethylammonium chloride</strong> (1.32 ml), and O2 was bubbled through the solution for about 15 min. The solution was heated to about 90 C. for about 6 hrs, while continuing to introduce O2 into the reaction vessel. Product was then recovered. The resulting yield of citral was 43%.
With oxygen; To the solution was then added myrcene (3 ml), n-butanol (7.5 ml) and <strong>[112-02-7]cetyltrimethylammonium chloride</strong> (1.32 ml), and O2 was bubbled through the solution for about 15 min. The solution was heated to about 90 C. for overnight, while continuing to introduce O2 into the reaction vessel. Product was then recovered. The resulting yield of citral was 66%.
  • 32
  • [ 123-35-3 ]
  • [ 112-02-7 ]
  • [ 5392-40-5 ]
YieldReaction ConditionsOperation in experiment
With carbon dioxide; In toluene; To the solution was then added myrcene (0.66 ml), toluene (7.5 ml) and <strong>[112-02-7]cetyltrimethylammonium chloride</strong> (1.5 ml). Carbon dioxide was bubbled through for about 20 min, the solution was heated to about 90 C. for about 2.5 hrs, and product recovered. The resulting yield of citral was 27%.
In toluene; To the solution was then added myrcene (2.83 ml), toluene (7.5 ml) and <strong>[112-02-7]cetyltrimethylammonium chloride</strong> (1.32 ml). Oxygen was bubbled through for about 20 min, the solution was heated to about 90 C. for about 4 hrs, and product recovered. The resulting yield of citral, analyzed using external standard gas chromatography, was 20%.
  • 33
  • [ 123-35-3 ]
  • [ 2043-21-2 ]
  • [ 1197419-88-7 ]
YieldReaction ConditionsOperation in experiment
67% With copper(II) bis[bis((trifluoromethyl)sulfonyl)amide]; N,N'-(4R,4'R,5R,5'R)-2,2'-(propane-2,2-diyl)bis(5-methyl-4,5-dihydrooxazole-4,2-diyl)bis(methylene)bis(1,1,1-trifluoromethanesulfonamide) In Nitroethane at -20℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 34
  • [ 763-10-0 ]
  • [ 99-83-2 ]
  • [ 123-35-3 ]
  • [ 3338-55-4 ]
  • [ 3779-61-1 ]
  • [ 586-62-9 ]
  • [ 138-86-3 ]
YieldReaction ConditionsOperation in experiment
With recombinant (+)-cadinene synthase from Gossypium arboreum; magnesium chloride; D,L-dithiothreitol In pentane at 25℃; for 24h; HEPES buffer; Enzymatic reaction;
  • 35
  • [ 123-35-3 ]
  • [ 79202-96-3 ]
  • [ 1448049-65-7 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 7-methyl-3-methene-1,6-octadiene With bis(cyclopentadienyl)titanium dichloride; isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; Stage #2: N,N-dibenzotriazol-1-ylmethylaminocyclohexane In tetrahydrofuran at 10 - 20℃;
  • 36
  • [ 123-35-3 ]
  • [ 57684-32-9 ]
  • [ 1448049-58-8 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 7-methyl-3-methene-1,6-octadiene With bis(cyclopentadienyl)titanium dichloride; isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; Stage #2: N-((1 H-benzo[d][1,2,3]triazol-1-yl)methyl)-N-benzyl-1-phenylmethanamine In tetrahydrofuran at 10 - 20℃;
  • 37
  • [ 123-35-3 ]
  • [ 1460-57-7 ]
  • (4aRS,8aSR)-6-(4-methylpent-3-en-1-yl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-4a,8a-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With dodecacarbonyl-triangulo-triruthenium; 1,3-bis-(diphenylphosphino)propane In toluene at 130℃; for 48h; Inert atmosphere;
84% With dodecacarbonyl-triangulo-triruthenium; 2,2'-bis(diphenylphosphino)biphenyl In toluene at 130℃; for 48h; Inert atmosphere; diastereoselective reaction;
  • 38
  • [ 13803-39-9 ]
  • [ 123-35-3 ]
  • C21H24O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With carbonyldihydridotris(triphenylphosphine)ruthenium(II); trifluoroacetic acid In toluene at 110℃; for 18h; Schlenk technique;
  • 39
  • [ 2150-43-8 ]
  • [ 123-35-3 ]
  • [ 1529815-44-8 ]
YieldReaction ConditionsOperation in experiment
86.9% With silver(l) oxide In diethyl ether; toluene at 0 - 20℃; for 23h; Diels-Alder reaction of methyl 3,4-dioxocyclohexa-1,5-diene-carboxylate with myrcene and ocimene (adducts 10, 13) General procedure: To a solution of methyl 3,4-dihydroxybenzoate (1.0 g, 3.31 mM), myrcene or ocimene (2.25 g, 16.1 mM) in toluene(10 mL) and diethyl ether (4.5 mL), Ag2O (0.7 g, 3.31 mM) was added at 0°C for 3 h. The stirring was continued for 20 hat RT. The reaction mixture was filtered through celite, washed with ether and the filtrate was evaporated under reducedpressure. The column chromatography of the residue over silica gel and elution with hexane: ethyl acetate (90:10) gives a9:1 mixture of region isomers. The isomers were separated by preparative TLC (eluent: hexane-Ethyl acetate, 95:5).
  • 40
  • [ 99-50-3 ]
  • [ 123-35-3 ]
  • C16H20O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55.46% With [bis(acetoxy)iodo]benzene In di-isopropyl ether; acetonitrile at 0℃; for 1h; Diels-Alder reaction of 3,4-dioxocyclohexa-1,5-diene-carboxylic acid with myrcene and ocimene (adducts 17-20) General procedure: To a solution of 3,4-dihydroxybenzoic acid (0.15 g, 0.974 mM), myrcene or ocimene (0.662 g, 4.8 mM) in diisopropylether (1 mL) and ACN (0.6 mL), IBD (0.313 g, 0.974 mM) was added at 0°C. The stirring was continued for 1 h. The solvent was removed in vacuo and the residue was subjected to column chromatography over silica gel, elution with hexane:ethyl acetate (90:10) gave pure compounds 17 -20.
  • 41
  • [ 123-35-3 ]
  • [ 490-79-9 ]
  • [ 177327-05-8 ]
YieldReaction ConditionsOperation in experiment
61.34% With [bis(acetoxy)iodo]benzene In di-isopropyl ether; acetonitrile at 0℃; for 1h; Diels-Alder reaction of 3,4-dioxocyclohexa-1,5-diene-carboxylic acid with myrcene and ocimene (adducts 17-20) General procedure: To a solution of 3,4-dihydroxybenzoic acid (0.15 g, 0.974 mM), myrcene or ocimene (0.662 g, 4.8 mM) in diisopropylether (1 mL) and ACN (0.6 mL), IBD (0.313 g, 0.974 mM) was added at 0°C. The stirring was continued for 1 h. The solvent was removed in vacuo and the residue was subjected to column chromatography over silica gel, elution with hexane:ethyl acetate (90:10) gave pure compounds 17 -20.
  • 42
  • [ 123-35-3 ]
  • [ 4358-64-9 ]
  • (3aR*,7aS*)-5-(4-methylpent-3-en-1-yl)-1,3,3a,4,7,7a-hexahydroisobenzofuran-3a,7a-diol [ No CAS ]
  • 43
  • [ 25021-08-3 ]
  • [ 123-35-3 ]
  • 2-[5-(4-methylpent-3-en-1-yl)-1,3-dioxo-3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)-yl]acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% In tetrahydrofuran; at 20℃; Imide 1 (0.20 g, 1.3 mmol) was dissolvedin 5 ml of THF. Then 0.34 ml (2.0 mmol) of myrcene was added to thissolution.The mixture was left overnight at room temperature. Thereafter,THF was removed in a vacuum and the solid residue was recrystallizedfrom n-hexane to yield 0.28 g (74%) of compound 2, mp 84-85 C. 1H NMR(CDCl3) d: 1.59 (s, 3 H, Me), 1.68 (s, 3 H, Me), 2.03 (m, 4 H, CH2), 2.26(m, 2 H, CH2), 2.56 (m, 2 H, CH2), 3.17 (ddd, 2 H, CH, 3JHH 9.2 Hz,3JHH 6.3 Hz, 3JHH 3.4 Hz), 4.25 [s, 2 H, C(O)CH2N], 5.03 (br. s, 1H, =CH),5.57 (br. s, 1H, =CH). 13C NMR (CDCl3) d: 17.7, 24.0, 25.7, 25.9, 27.5,37.2, 39.2, 39.5, 39.8, 119.8, 123.6, 131.9, 140.2, 171.5, 179.2, 179.4.IR (n/cm-1): 1748, 1676 (C=O), 2728, 2601, 2520 (COOH). MS (MALDITOF),m/z: 291.9 [M + H]+, 313.8 [M + Na]+ (calc. for [M+], m/z 291.2).Found (%): C, 65.72; H, 7.07; N, 5.10. Calc. for C16H21NO4 (%): C, 65.96;H, 7.27; N, 4.81.
  • 44
  • [ 763-10-0 ]
  • [ 78-70-6 ]
  • [ 123-35-3 ]
  • [ 106-24-1 ]
  • [ 586-62-9 ]
  • [ 98-55-5 ]
  • [ 2009-00-9 ]
  • [ 563-34-8 ]
  • [ 5989-54-8 ]
  • 45
  • [ 123-35-3 ]
  • [ 4180-23-8 ]
  • (±)-(1S,2S)-4'-methoxy-2-methyl-4-(4-methylpent-3-en-1-yl)-1,2,3,6-tetrahydro-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With iron perchlorate hexahydrate In acetonitrile at 20℃; for 24h; regioselective reaction;
88% With C26H18N10Ru(2+)*2C32H12BF24(1-) In dichloromethane for 1.5h; Irradiation;
84% With 9-(2-trifluoromethylphenyl)-1,3,6,8-tetramethoxythioxanthylium trifluoromethanesulfonate In nitromethane at 20℃; for 1h; UV-irradiation; General procedure for [4+2] cycloaddition with photocatalyst under visible light irradiation General procedure: The alkene (1)(0.50 mmol), diene(2) (1.5 mmol),TXT1 (1.0 mol%) andCH3NO2 (8.0 mL) wereadded intoa 10 ml recovery flask. The resulting solution was stirred at room temperature under air and green LEDirradiation. After the reaction was completed (checked byTLC), the desired cycloadduct3was isolated bycolumn chromatography on silica gel (hexane/ethylacetate = 100/1).
76% With iron(III) chloride In dichloromethane; acetonitrile at 0℃; for 3h;

  • 46
  • [ 123-35-3 ]
  • [ 14814-09-6 ]
  • C28H60O6S2Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With 2,2'-azobis(isobutyronitrile); In toluene; at 60℃; for 3h;Inert atmosphere; beta- myrcene (manufactured by Tokyo Kasei Kogyo (Co.)) 50 g, (3- mercaptopropyl) triethoxysilane (produced by Tokyo Chemical Industry (Ltd.)) 175.0 g, 2,2'-azobis (isobutyronitrile) (Wako Pure Chemical mixed industrial Co., Ltd., Ltd.) 3.50 g and toluene 200mL were mixed in a round-bottomed flask, was bubbled with nitrogen gas for 30 minutes, and reacted for 3 hours at 60 C.. Thereafter, the reaction solution was concentrated, liquid of a pale yellow 203g was obtained (yield: 90%). From the results the following NMR, the product was identified to be a compound represented by the following formula (13) (organosilane 3).
  • 47
  • [ 565-62-8 ]
  • [ 123-35-3 ]
  • [ 57499-57-7 ]
YieldReaction ConditionsOperation in experiment
822 g Stage #1: 3-methyl-3-pentene-2-one With Aluminum Chloride In toluene at 50℃; for 1h; Stage #2: 7-methyl-3-methene-1,6-octadiene In toluene at 50℃; for 2h; Addition of diene to give D-A addition product Into a 2-liter three-necked flask, 300 g of toluene was added, 27 g of anhydrous aluminum chloride was added in portions, and 450 gMP0, finished drop within an hour. Stir heating to 50 ° C, dropwise add 700g myrcene. After the dropwise addition is complete, keep the temperature and continue to stirThe reaction was stopped for 2 hours. Washed once with 400 g of saturated brine, once with 300 g of 10% sodium carbonate solution, and finally with waterWash to pH 7. Distillation under reduced pressure, 293 g of toluene and 18 g of MP0 were recovered to give D-A addition product - Isoprid Salmonella822g
With 2,6-di-tert-butyl-4-methyl-phenol In ethanol at 40 - 65℃; for 3h; 1.2.1; 4 Myrcene and dibutylhydroxytoluene are housed in the myrcene liquid storage tank, the 3M3P collection tank is housed with the compound 3M3P synthesized by the above steps "(1.2) compound 3M3P synthesis method", and the cosolvent storage tank is housed with ethanol;Myrcene, dibutylhydroxytoluene, compound 3M3P and ethanol in the myrcene liquid storage tank, the 3M3P collection tank and the cosolvent liquid storage tank enter the mixer through pipelines, wherein the mass ratio of myrcene, compound 3M3P, and ethanol It is 0.8:0.5:0.2, and the mass of dibutylhydroxytoluene is 0.5‰ of myrcene. It is mixed with a mixer and heated to 40°C and then enters the floating bed reactor for reaction (reaction temperature is 45°C, reaction time is 1h) , the reaction solution after the reaction in the floating bed reactor enters the first fixed bed reactor (12) for reaction (the reaction temperature is 55°C and the reaction time is 0.6h), and the reaction solution after the reaction in the first fixed bed reactor enters the buffer tank , and then the reaction solution of the buffer tank enters the second fixed-bed reactor through the pipeline to react (the reaction temperature is 65°C, and the reaction time is 1.5h), and a part of the compound ISOP crude product reaction solution obtained after the second fixed-bed reactor reaction is passed through with The fourth liquid outlet pipe connected to the fifth circulation pipe enters the ISOP crude product collection tank, and a part of the compound ambroxone crude product reaction solution is returned to the three-stage fixed bed reactor through the fifth circulation pipe.After testing and calculation, the purity of the compound ISOP in the ISOP crude product collection tank is 72%.
  • 48
  • [ 25021-08-3 ]
  • [ 123-35-3 ]
  • 2-[5-(4-methylpent-3-en-1-yl)-1,3-dioxo-3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)-yl]acetic acid [ No CAS ]
  • 49
  • [ 565-62-8 ]
  • [ 123-35-3 ]
  • [ 54464-57-2 ]
YieldReaction ConditionsOperation in experiment
92.2% at 170 - 250℃; 7 Synthesis Example of ambergris ketone [0085] In a 250mL reactor equipped with a thermometer, a stirrer, a constant pressure dropping funnel and a high temperature cracking reaction tube, added the β-Pinene (150g, 1.10mol), open the stir, the reaction vessel slowly heated at 170 ° C, and at this point β-Pinene began to evaporate, the gas phase passes through a high temperature cracking tube that has been heated at 500 ° C, cracking reaction occurs. After pyrolysis the myrcene is cooled to 250 ° C via high temperature heat transfer oil, the vapor is then passed to a 250 ° C condensation reactor. [0086] in another 100mL reactor, added the 3-methyl-3-pentene-2-one (54.0g, 0.55mol). Open the stir, the reaction vessel slowly heated at 170 ° C, evaporated the gaseous 3-methyl-3-pentene-2-one, after passing through the 250 ° C reheater, put into 250 ° C condensation reactor with myrcene mixed after that occurrence of the intermolecular Diels-Alder reaction, the high temperature gas is condensed and distilled under reduced pressure to collect 134-136 ° C / 10mmHg fraction, and then obtained light yellow viscous liquid (Bicyclohomofarnesal intermediate), yield 92.2%, purity 96.7%.
  • 50
  • [ 221044-05-9 ]
  • [ 123-35-3 ]
  • 2-(4-methylpent-3-en-1-yl)-9-(pyrimidin-2-yl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate; oxygen; copper(II) acetate monohydrate; In methanol; at 40℃;Sealed tube; N-pyrimidine oxime (0.2 mmol, 1.0 equiv), 7-methyl-3-methylene-1,6-octadiene (0.24 mmol, 1.2 equiv) was sequentially added to the branch.[Cp*Rh(CH3CN)3](SbF6)2 (3.1 mg, 0.005 mmol), copper acetate monohydrate (4.0 mg, 0.04 mmol, 20 mol%), 1.0 mL methanol solvent.The reaction tube was sealed, oxygen gas was introduced, and the reaction solution was stirred at 40 C to cause a reaction.After completion of the reaction, the reaction solution was diluted with dichloromethane, washed with a saturated aqueous solution of ammonium chloride, and the aqueous phase was extracted again with dichloromethane.The combined organic layers were washed with brine and dried over anhydrous sodium sulfate.The solvent was evaporated in vacuo and purified by silica gel column chromatography.It was a white solid with a yield of 82%.
  • 51
  • [ 123-35-3 ]
  • [ 106-25-2 ]
  • [ 106-24-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-methyl-3-methene-1,6-octadiene With hydrogenchloride at 30 - 35℃; for 3h; Stage #2: With acetic acid In ethyl acetate Reflux; Stage #3: With water; sodium hydroxide for 6h; 2 Comparative example 2 According to Liu Xianzhang et al. (Forest Chemicals and Industry, 1989, 9(4), 11-19), the synthesis was carried out by using myrcene: 120 g of myrcene was introduced, hydrogen chloride gas was introduced, and the addition reaction time was 3 hours, and the reaction temperature was 30-35. °C.After the reaction is completed, 300 g of acetic acid is directly added.500 g of ethyl acetate was heated under reflux to carry out an esterification reaction.After the esterification is completed, the ethyl acetate is removed by rotary evaporation.Hydrogen chloride and acetic acid gave 183 g of a crude ester.The crude product was distilled under reduced pressure to collect a product of 75 to 120 ° C / 5 mm Hg.Saponified with 500 g of 30% aqueous sodium hydroxide solution on a water bath for 6 hours, and then filtered to recover sodium acetate.Evaporate the ethanol and wash it to neutrality.Collecting fractions of 80-115 ° C / 5 mm Hg by distillation,The crude alcohol is subjected to rectification to separate nerol and geraniol.The yield of both is 71.3%, and the purity is 95-96%.Single impurity <1.5%, total impurity content 4 to 5%(Chloro-dihydromyrcene, geranyl acetate, etc.).
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