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Chemical Structure| 35354-74-6
Chemical Structure| 35354-74-6
Structure of 35354-74-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 35354-74-6 ]

CAS No. :35354-74-6 MDL No. :MFCD00016674
Formula : C18H18O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FVYXIJYOAGAUQK-UHFFFAOYSA-N
M.W : 266.33 Pubchem ID :72303
Synonyms :
NSC 293100

Calculated chemistry of [ 35354-74-6 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.11
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 84.14
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.96
Log Po/w (XLOGP3) : 4.98
Log Po/w (WLOGP) : 4.22
Log Po/w (MLOGP) : 3.78
Log Po/w (SILICOS-IT) : 4.99
Consensus Log Po/w : 4.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.74
Solubility : 0.00482 mg/ml ; 0.0000181 mol/l
Class : Moderately soluble
Log S (Ali) : -5.57
Solubility : 0.000719 mg/ml ; 0.0000027 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.47
Solubility : 0.000907 mg/ml ; 0.0000034 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.45

Safety of [ 35354-74-6 ]

Signal Word:Danger Class:9
Precautionary Statements:P273-P280-P305+P351+P338+P310-P391-P501 UN#:3077
Hazard Statements:H318-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 35354-74-6 ]

* 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 [ 35354-74-6 ]

[ 35354-74-6 ] Synthesis Path-Downstream   1~62

  • 1
  • [ 35354-74-6 ]
  • [ 35406-31-6 ]
YieldReaction ConditionsOperation in experiment
94% With palladium 10% on activated carbon; hydrogen; In methanol; for 5h;Reflux; A mixture of honokiol (2.0 mmol) and Pd/C (10%, 0.1 mmol) in MeOH (10 mL) was refluxed under H2 (0.5 Mpa) for 5 h. After cooling, the mixture was filtered and concentrated under reduced pressure. The residue was then purified by silica gel chromatography to afford B3 as white solid (94%). m.p. 110-112 C. 1H NMR (400 MHz, CDCl3) delta 7.21 (s, 1H, Ar-H), 7.17 (d, J = 8.2 Hz, 1H, Ar-H), 7.06-6.99 (m, 2H, Ar-H), 6.88 (d, J = 8.2 Hz, 1H, Ar-H), 6.86 (d, J = 8.2 Hz, 1H, Ar-H), 5.07 (s, 1H, OH), 4.78 (s, 1H, OH), 2.63 (t, J = 7.7 Hz, 2H, CH2CH2CH3), 2.54 (t, J = 7.7 Hz, 2H, CH2CH2CH3), 1.73-1.58 (m, 4H, 2?CH2CH2CH3), 1.00 (t, J = 7.3 Hz, 3H, CH2CH2CH3), 0.95 (t, J = 7.3 Hz, 3H, CH2CH2CH3); 13C NMR (101 MHz, CDCl3) delta 153.29, 150.35, 135.00, 131.03, 130.11, 129.55, 129.50, 128.64, 127.71, 115.98, 115.38, 37.26, 32.08, 24.83, 22.91, 14.09, 13.89. LC-MS, m/z: 271.0 [M+H]+ . Elemental anal.(%) calcd. for C18H22O2: C 79.96, H 8.20; Found: C 80.03, H 8.18.
With Lindlar's catalyst; hydrogen; In ethanol; at 20℃; under 760.051 Torr; for 24h; General procedure: The hydrogenation of 2-4, eugenol, and 2-allyl phenol (0.5 mmol) was carried out employingabsolute EtOH (7 mL) and Pd/CaCO3 (10%w/w; 17.4 mg) as catalyst. The reaction flask was filled withH2(1 atm) and stirred at rt for 24 h. The catalyst was removed by filtration on Celite 545. In these conditionsthe expected products have been obtained quantitatively without further purification. The spectroscopicdata of 30,5-dipropyl-(1,10-biphenyl)-2,40-diol (5) [42] 2,40-dimethoxy-30,5-dipropyl-1,10-biphenyl(7) [42] 2-methoxy-4-propylphenol (10a) [45] and 2-propylphenol (10b) [46] were in agreement withliterature data.
  • 3
  • [ 108-31-6 ]
  • [ 35354-74-6 ]
  • [ 1048647-35-3 ]
YieldReaction ConditionsOperation in experiment
53% Example 3: 3-({4-[2-(3-carboxypropanoyloxy)-5-prop-2-enylphenyl]-2- prop-2-enylphenyl}oxycarbonyl)propionic acid; In a 250 ml of round bottom flask, 2-(4-hydroxy-3-prop-2-enylphenyl)-4-prop- 2-enylphenyl-l-ol (2.93 g, 0.01 M) was dissolved in 200 ml of pyridine at 5O0C, maleicanhydride (3,4-dihydrofuran-2,5-dion) (4 g, 0.04M, Sigma) was added, and the solution was reacted for 2 days. After completion of the reaction, a solvent were removed by vacuum, and the residual was dissolved in 100 ml of 5% NaHCO3 solution. <n="25"/>The resultant solution was extracted twice with 50 ml of ethylacetate, the residual was eliminated, and cooled to O0C. 200 ml of 10% citric acid was added to thereto for acidifying and extracted twice with 100 ml of ethylacetate. The extract was washed twice with water, the moisture was removed from the extract using anhydrous calcium carbonate and organic solvent was eliminated under vacuum distillation, thereby obtaining 2.5 g (yield: 53%) of 3-({4-[2-(3-carboxypropanoyloxy)-5-prop-2- enylphenyl]-2-prop-2-enylphenyl}oxycarbonyl)propionic acid represented by the following formula VIII (the prepared sample names as "2"): NMR (delta, ppm CDCI3): 7.0- 7.3 (6H,m), 5.9 (2H,m), 5.1 (4H,q), 4.1 (lH,md), 3.4 (4H,d), 2.9 (4H,md), 2.6 (4H,md); IR (cm"1 ; C=O) 1765, 1770; 13C (ppm ; C=O) 171, 172
  • 4
  • [ 4530-20-5 ]
  • [ 35354-74-6 ]
  • C22H24N2O4*2ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% Example 1: 2-(4-aminoethanoyl-3-prop-2-enylphenyl)-4-prop-2- enylphenyl-2-aminoethanoate di hydrochloride salt; In a 250 ml round bottom flask, Boc-Gly:(2-[l-(l,l-dimethyl ethyloxy)ethenyl]amino}ethanoic acid) (1.74 g, 10 mmol, Sigma) was dissolved in 50 <n="23"/>ml of anhydrous chloroform and 50 ml of dioxin and cooled to O0C, followed by adding DCC (l,3-diaza-l,3-dicyclohexylpropa-l,2-diene) (Sigma). 2-(4-hydroxy-3-prop-2- enylphenyl)-4-prop-2-enylphenyl-l-ol (2.93 g, 0.01 M) and TEA (triethylamine, 1.26 ml, 0.09 M) were slowly added to the reaction solution at O0C and stirred for 1 day at room temperature, followed by stirring for 6 hr at 4O0C to complete the reaction. After filtration of the solution, the filtrate was washed with 1 N HCI, 5% NaHCO3 solution and water. Moisture was removed from the residual solution using anhydrous calcium carbonate and organic solvent was eliminated under vacuum. The residual was dissolved in ethylacetate and was subjected to bubbling with HCI for 4 hr at room temperature. Following concentration, the residual was recrystallized with ether/petroleum ether, thereby obtaining 1.51 g (yield: 43%) of 2-(4-aminoethanoyl-3- prop-2-enylphenyl)-4-prop-2-enylphenyl-2-aminoethanoate dihydrochloride salt represented by the following formula VI (the prepared sample names as "1"): NMR (delta, ppm D2O+DMSO): 8.4 (2H,b), 7.0-7.2 (6H,m), 5.9 (2H,m), 5.1 (4H,d), 3.9 (2H,s), 3.4 (4H,q); IR (cm"1; C=O) 1630, 1625; 13C (ppm; C=O) 171, 172 Formula VI
  • 5
  • [ 15761-38-3 ]
  • [ 35354-74-6 ]
  • C24H28N2O4*2ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% Example 2: 2-(4~aminopropanoyl-3~prop-2-enylphenyl)-4-prop-2- enylphenyl-2-aminopropanoate dihydrochloride salt; In a 250 ml of round bottom flask, Boc-Ala:(2-[1-(1,1- dimethyl ethyloxy)etheny.]amino}propanoic acid) (1.88 g, 10 mmol, Sigma) was dissolved in 50 ml of anhydrous chloroform and 50 ml of dioxin, cooled to O0C, followed by adding DCC (l,3-diaza-l,3-dicyclohexylpropa-l,2-diene) (Sigma). 2-(4-hydroxy-3-prop-2- <n="24"/>enylphenyl)-4-prop-2-enylphenyl-l-ol (2.93 g, 0.01 M) and TEA (triethylamine, 1.26 ml, 0.09 M) were slowly added to the reaction solution at O0C and stirred for 1 day at room temperature, followed by stirring for 6hr at 400C to complete the reaction. After filtration of the solution, the filtrate was washed with 1 N HCI, 5% NaHCO3 solution and water. Moisture was removed from the residual solution using anhydrous calcium carbonate and organic solvent was eliminated under vacuum. The residual was dissolved in ethyacetate and was subjected to bubbling with HCI for 4 hr at room temperature. Following concentration, the residual was recrystallized with ether/petroleum ether, thereby obtaining 1.68 g (yield: 45%) of 2-(4-aminopropanoyl- 3-prop-2-enylphenyl)-4-prop-2-enylphenyl-2-arninopropanoate dihydrochloride salt represented by the following formula VII: NMR(delta, ppm D2O-I-DMSO): 8.4 (2H,b), 7.0- 7.3 (6H,m), 5.9 (2H,m), 5.1 (4H,q), 3.9 (lH,d), 3.4 (2H,d), 1.3 (3H,d); IR (cm"1; C=O) 1630, 1625; 13C (ppm; C=O) 171, 172 Formula VII
  • 6
  • [ 68592-19-8 ]
  • [ 35354-74-6 ]
YieldReaction ConditionsOperation in experiment
90% With boron tribromide; In dichloromethane; at 20℃; for 0.416667h;Inert atmosphere; 500 mg of the 3,5?-diallyl-2?-methoxy-biphenyl-4-ol (compound 8) as obtained in Step V of this example was dissolved into 5 mL of DCM. 3.8 mL of a 1 M solution of BBr3 in dry DCM was added to the resultant solution over a period of 5 minutes under argon. The resultant mixture was stirred at ambient temperature for 25 minutes (TLC monitoring). The reaction was quenched with a saturated NaHCO3 solution. An extraction treatment with DCM (3×20 mL) was conducted. The resultant organic layer was washed with brine (2×20mL), and was dried over MgSO4, followed by a concentration process under reduced pressure. A gray solid residue was formed and was subjected to a purification treatment employing silica gel column chromatography (EtOAc-hexane (15:85) as a mobile phase). Therefore, 5,3?-diallyl-biphenyl-2,4?-diol (product 1 or compound 1) as a white solid was obtained (90% yield).
430 mg With boron tribromide; In dichloromethane; at 20℃; for 0.416667h;Inert atmosphere; To a solution of compound 8 (500 mg, 1.79 mmol) in DCM (5 mL) was added a solution of BBr3 (3.8 mL, 1 M in DCM) in dry DCM (35 mL) during a period of 5 min under argon atmosphere. The resulting mixture was stirred at ambient temperature for another 25 min when TLC revealed total disappearance of starting material. The reaction was quencnched with saturated NaHCO3 solution. The organic layer was extracted with DCM (3 20 mL) and washed with brine (2 20 mL). The organic phase was dried over MgSO4 and concentrated under reduced pressure to furnish gray solid residue which was purified by a silica gel column chromatography using a mixture of EtOAc-hexanes (15:85) as the mobile phase to yield product 1 (430 mg, 1.60 mmol, 90%) as a white solid. mp 84-86 C. 1H NMR (400 MHz, CDCl3, delta): 7.23 (m, 2H), 7.06 (m, 2H), 6.91 (m, 2H), 6.02 (m, 2H), 5.32 (b, 1H), 5.20 (m, 3H), 5.09 (m, 2H), 3.47 (d, J = 6.4 Hz, 2H), 3.36 (d, J = 6.7 Hz, 2H). 13C NMR (100.6 MHz, CDCl3, delta): 153.9, 150.8, 137.8, 136.0, 132.3, 131.2, 130.3, 129.6, 128.8, 128.6, 127.8, 126.5, 116.9, 116.6, 115.6, 39.4, 35.1. EIMS (70 eV) m/z: 266.3 (M+, 100), 237.2 (13.1), 197.1 (9.6) 184.1 (10.8). HRMS-EI (m/z): M+ calcd for C18H18O2, 266.1307; found 266.1311.
  • 7
  • [ 35354-74-6 ]
  • [ 108-24-7 ]
  • [ 35347-50-3 ]
YieldReaction ConditionsOperation in experiment
56% With potassium carbonate; at 20℃; for 0.5h; General procedure: <strong>[35354-74-6]Honokiol</strong> (214.2 mg, 0.76 mmol) was mixed with acetic anhydride (10 mL) and with K2CO3(445.3 mg, 3.2 mmol) at rt for 30 min. The mixture was diluted with cold water (10 mL) and partitionedwith EtOAC (3 x 15 mL), the combined organic phase was dried over anhydrous Na2SO4, filteredand taken to dryness. The recovered organic layer was purified by column chromatography onsilica gel (n-hexanen-hexane:acetone 60:40) to give acetyl honokiol (3) with 56% yield (150.4 mg).Spectroscopic data were in agreement with those previously reported [41].
  • 8
  • [ 35354-74-6 ]
  • [ 74-88-4 ]
  • [ 68592-19-8 ]
  • [ 68592-15-4 ]
  • [ 68592-18-7 ]
YieldReaction ConditionsOperation in experiment
15%; 30%; 15% With caesium carbonate; In tetrahydrofuran; acetone; at 60℃; To an acetone solution (10 mL) of honokiol (1.13 g,4.24 mmol) was added Cs2CO3 (1.38 g, 4.24 mmol), by 1 M iodomethane in tetrahydrofuran (THF) (0.5 mL, 5.08 mmol).After stirring at reflux overnight, the reaction mixture was dilutedin ethyl acetate, washed with water and brine, dried overMgSO4, and concentrated under reduced pressure. The residuewas purified by flash column chromatography on silica gel(ethyl acetate : n-hexane = 1 : 19 to 1 : 2) to afford 1a (330 mg,30%, BORSM (Based on recovered starting material) 36%),1b (210 mg, 15%, BORSM 23%), 1c (182 mg, 15%, BORSM19%), and recovered honokiol (280 mg). For 1a, 1H-NMR(600 MHz, CDCl3) delta: 7.28 (d, J = 8.3 Hz, 1H), 7.23 (s, 1H),7.05 (d, J = 8.2 Hz, 1H), 7.03 (s, 1H), 6.96 (d, J = 8.3 Hz, 1H),6.90 (d, J = 8.2 Hz, 1H), 6.05-5.93 (m, 2H), 5.11-5.06 (m, 4H),5.04 (bs, 1H), 3.88 (s, 3H), 3.43 (d, J = 6.6 Hz, 2H), 3.35 (d,J = 6.6 Hz, 2H); 13C-NMR (150 MHz, CDCl3) delta: 157.2, 151,138, 136.6, 132.3, 130.6, 130.3, 129.9, 129.1, 128.9, 128.0, 128,116.0, 115.7, 115.7, 111.1, 55.7, 39.6, 34.4; HRMS (electronionization (EI)) m/z: [M] Calcd for C19H20O2 280.1463. Found280.1466. For 1b, 1H-NMR (600 MHz, CDCl3) delta: 7.31 (dd,J = 8.2, 2.2 Hz, 1H), 7.28 (d, J = 2.2 Hz, 1H), 7.11-.09 (m, 2H),6.90 (d, J = 8.1 Hz, 1H), 6.85 (d, J = 8.2 Hz, 1H), 6.10-5.95(m, 2H), 5.24-5.20 (m, 2H), 5.11-5.04 (m, 2H), 5.03 (bs, 1H)3.79 (s, 3H), 3.46 (d, J = 6.4 Hz, 2H), 3.37 (d, J = 6.7 Hz, 2H);13C-NMR (150 MHz, CDCl3) delta: 154.8, 153.3, 137.8, 136.5, 132.3, 131.5, 131.2, 131, 130.3, 129.1, 128, 124.7, 116.6, 115.6,115.5, 111.3, 55.7, 39.4, 35.4; HRMS (EI) m/z: [M] Calcdfor C19H20O2 280.1463. Found 280.1461. For 1c, 1H-NMR(600 MHz, CDCl3) delta: 7.41-7.39 (m, 1H), 7.34 (s, 1H), 7.15 (s,1H), 7.12 (d, J = 8.3 Hz, 1H), 6.92 (dd, J = 8.3, 0.9 Hz, 2H),6.09-5.98 (m, 2H), 5.14-5.10 (m, 2H), 5.09-5.06 (m, 2H), 3.88(d, J = 1.0 Hz, 3H), 3.81 (d, J = 1.2 Hz, 3H), 3.46 (d, J = 6.5 Hz,2H), 3.40 (d, J = 6.4 Hz, 2H); 13C-NMR (150 MHz, CDCl3)delta: 156.5, 155.0, 137.9, 137.2, 132.3, 131.1, 131.1, 130.8, 130.6,128.5, 128.2, 128.0, 115.6, 115.5, 111.4, 110.0, 55.8, 55.6, 39.6,34.5; LRMS (ESI) m/z: Calcd for C20H22O2 [M + Na]+ 317.15.Found 317.25.
19.9%; 12.3%; 6.9% With sodium carbonate; In N,N-dimethyl-formamide; at 65℃; for 3h; <strong>[35354-74-6]Honokiol</strong> was used as raw material (532 mg, 2.0 mM)and dimethyl formamide as solvent (5 mL). Sodium carbonate solution (5 mL, 25%)and iodomethane (125 muL, 2 mM) were added to react and kept stirring for 3 h in oil bathat 65 oC. Then the reaction was quenched with water andextracted with ethyl acetate for twice. Thecombined extracts were dried over Na2SO4 and concentratedunder reduced pressure.1 The residuewas then purified by silica gel chromatography with eluent (petroleumether: ethyl acetate = 50: 1 to 20: 1) to afford 1a-1c. For 1a (68.5 mg, yield12.3%), 1H NMR (600 MHz, CD3OD): delta 7.14 (1H, d, J= 2.3 Hz), 7.12 (1H, dd, J = 2.3, 8.2 Hz), 7.02 (1H, dd, J = 2.3,8.3 Hz), 7.01 (1H, d, J = 2.3 Hz), 6.92 (1H, d, J = 8.3 Hz), 6.75(1H, d, J = 8.3 Hz), 5.92-6.04 (2H, m), 4.97-5.07 (4H, m), 3.72 (3H, s),3.36 (2H, d, J = 6.7 Hz), 3.32 (2H, d, J = 6.9 Hz). 13CNMR (150 MHz, CD3OD): delta 154.9 (C-4'), 153.7 (C-2), 137.9 (C-8),137.1 (C-8'), 132.1 (C-2'), 130.8 (C-5), 130.7 (C-6), 130.2 (C-1'), 129.9 (C-1),127.8 (C-4), 127.4 (C-6'), 125.6 (C-3'), 114.1 (C-3), 113.9 (C-9), 113.9 (C-9'),111.4 (C-5'), 54.8 (2-OCH3), 38.9 (C-7), 33.8 (C-7'). ESI-MS: m/z279.14 [M - H]-. For 1b (83 mg, yield 19.9%), 1HNMR (600 MHz, CD3OD): delta 7.34 (1H, dd, J = 2.3, 8.4 Hz),7.27 (1H, d, J = 2.2 Hz), 6.99 (1H, d, J = 2.2 Hz), 6.93 (1H, d, J= 8.3 Hz), 6.91 (1H, dd, J = 2.3, 8.2 Hz), 6.77 (1H,d, J = 8.1 Hz), 5.92-6.02 (2H, m), 4.96-5.05 (4H, m), 3.83 (3H, s), 3.37(2H, d, J = 6.6 Hz), 3.30 (2H, m). 13C NMR (150 MHz, CD3OD):delta 156.2 (C-4'), 152.0 (C-2), 138.1 (C-8), 137.0 (C-8'), 131.1 (C-2'),131.0 (C-5), 130.4 (C-6), 130.1 (C-1'), 128.2 (C-1), 127.8 (C-4), 127.6 (C-6'),127.5 (C-3'), 115.1 (C-3), 114.0 (C-9), 114.0 (C-9'), 109.7 (C-5'), 54.5 (2-OCH3),39.0 (C-7), 33.9 (C-7'). ESI-MS: m/z 279.14 [M - H]-. For 1c(40.5 mg, yield 6.9%), 1H NMR (600 MHz, CD3OD): delta7.27 (1H, dd, J = 2.3, 8.4 Hz), 7.20 (1H, d, J = 2.3 Hz), 7.06(1H, dd, J = 2.3, 8.3 Hz), 7.03 (1H, d, J = 2.3 Hz), 6.93 (1H, d,J = 8.3 Hz), 6.91 (1H, d, J = 8.4 Hz), 5.93-6.01 (2H, m),4.97-5.07 (4H, m), 3.83 (3H, s), 3.73 (3H, s), 3.37 (2H, d, J = 6.6 Hz),3.32 (2H, d, J = 6.7 Hz). 13C NMR (150 MHz, CD3OD):delta 156.2 (C-4'), 154.9 (C-2), 137.9 (C-8), 137.0 (C-8'), 132.1 (C-2'),130.8 (C-5), 130.5 (C-6), 130.4 (C-1'), 130.3 (C-1), 128.0 (C-4), 127.6 (C-6'),127.5 (C-3'), 114.2 (C-3), 114.0 (C-9), 111.5 (C-9'), 109.6 (C-5'), 54.8 (2-OCH3),54.5 (4'-OCH3), 39.0 (C-7), 33.9 (C-7'). ESI-MS: m/z 295.17 [M + H]+.
  • 9
  • [ 889865-38-7 ]
  • [ 35354-74-6 ]
  • 10
  • [ 42142-52-9 ]
  • [ 35354-74-6 ]
  • [ 1356708-27-4 ]
  • [ 1356708-28-5 ]
YieldReaction ConditionsOperation in experiment
5% Example 4 '-Diallyl-2'-[3-(methylamino)-1 -phenylpropoxy1biphenyl-4-ol hydrochloride; Triphenylphosphine (0.740 g, 2.81 mmol) was dissolved in dry toluene (15 mL) and the solution was cooled down to 0 C. A solution of DEAD (~40% in toluene, 1 .29 mL, 2.81 mmol) was added dropwise and the mixture was stirred for 5 min. a-[2-(Methylamino)ethyl]benzyl alcohol was then added (0.372 g, 2.25 mmol), followed by the addition of honokiol (0.5 g, 1 .87 mmol). The solution was stirred at 0 C for 1 h and at 80 C for 16 h. The crude mixture was diluted with EtOAc and washed with 10% aqueous HCI (x3). The combined organic fractions were dried (MgS04), filtered, and evaporated to dryness. The resulting syrup was purified by column chromatography (S1O2, EtOAc/MeOH 0-20%). The desired compound was obtained as a yellow solid in 5% yield (0.043 g, 0.095 mmol), and the product described in Example 8 was also isolated. 1H NMR (200 MHz, CDCI3) delta 7.42 - 6.76 (m, 10H), 6.54 (d, J = 8.4, 1 H), 6.20 - 5.74 (m, 2H), 5.23 - 4.92 (m, 5H), 3.46 (d, J = 6.7, 2H), 3.29 (d, J = 6.6, 2H), 3.06 - 2.10 (m, 7H). 13C NMR (101 MHz, CDCI3) delta 154.38, 152.43, 139.95, 137.56, 136.97, 133.52, 131 .49, 131.21 , 130.91 , 129.81 , 129.12, 128.67, 128.33, 128.05, 127.27, 125.77, 1 16.14, 1 15.90, 1 14.48, 79.83, 47.09, 39.48, 34.59, 34.40, 33.53.
  • 11
  • [ 42142-52-9 ]
  • [ 35354-74-6 ]
  • [ 1356708-29-6 ]
  • 12
  • [ 42142-52-9 ]
  • [ 35354-74-6 ]
  • [ 1356708-58-1 ]
  • [ 1356708-55-8 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 - 80℃; for 17h;Product distribution / selectivity; Example 5; mL) and the solution was cooled down to 0 C. A solution of DEAD (~40% in toluene, 1 .29 mL, 2.81 mmol) was added dropwise and the mixture was stirred for 5 min. a-[2-(Methylamino)ethyl]benzyl alcohol was then added (0.372 g, 2.25 mmol), followed by the addition of honokiol (0.5 g, 1 .87 mmol). The solution was stirred at 0 C for 1 h and at 80 C for 16 h. The crude mixture was diluted with EtOAc and washed with 10% aqueous HCI (x3). The combined organic fractions were dried (MgS04), filtered, and evaporated to dryness. The resulting syrup was purified by column chromatography (S1O2, EtOAc/MeOH 0-20%). The desired compound was obtained as a yellow solid in 12% yield (0.100 g, 0.265 mmol), and the product described in Example 6 was also isolated. 1H NMR (400 MHz, CDCI3) delta 7.34 - 7.16 (m, 7H), 7.07 (dd, J = 8.4, 2.1 , 1 H), 7.00 - 6.88 (m, 2H), 6.63 (d, J = 8.6, 1 H), 6.07 - 5.84 (m, 2H), 5.33 (s, 1 H), 5.13 - 4.94 (m, 4H), 3.45 (d, J = 6.3, 2H), 3.29 (d, J = 6.7, 2H), 3.01 (t, J = 7.3, 2H), 2.56 - 2.24 (m, 5H).13C NMR (101 MHz, CDCI3) 5 154.63, 151 .64, 140.38, 138.27, 137.26, 132.32, 131 .45, 130.77, 130.69, 129.41 , 129.34, 128.98, 128.58, 128.42, 128.13, 126.21 , 1 16.38, 1 16.32, 1 15.91 , 1 13.64, 77.87, 46.83, 39.85, 35.19, 35.13, 33.56, 21 .50, 14.65.
  • 13
  • [ 42142-52-9 ]
  • [ 35354-74-6 ]
  • [ 1356708-27-4 ]
  • 14
  • [ 35354-74-6 ]
  • [ 1356708-58-1 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 - 80℃; for 17h; Example 5 3',5-Diallvl-4'-13-(methylamino)-1-phenylpropoxy]biphenyl-2-ol hydrochloride Triphenylphosphine (0.740 g, 2.81 mmol) was dissolved in dry toluene (15 mL) and the solution was cooled down to 0 C. A solution of DEAD (~40% in toluene, 1.29 mL, 2.81 mmol) was added dropwise and the mixture was stirred for 5 min. a-[2-(Methylamino)ethyl]benzyl alcohol was then added (0.372 g, 2.25 mmol), followed by the addition of honokiol (0.5 g, 1.87 mmol). The solution was stirred at 0 C for 1 h and at 80 C for 16 h. The crude mixture was diluted with EtOAc and washed with 10% aqueous HCI (x3). The combined organic fractions were dried (MgS04), filtered, and evaporated to dryness. The resulting syrup was purified by column chromatography (SiO2, EtOAc/MeOH 0-20%). The desired compound was obtained as a yellow solid in 12% yield (0.100 g, 0.265 mmol), and the product described in Example 6 was also isolated. 1H NMR (400 MHz, CDCl3) delta 7.34 - 7.16 (m, 7H), 7.07 (dd, J = 8.4, 2.1, 1H), 7.00 - 6.88 (m, 2H), 6.63 (d, J = 8.6, 1H), 6.07 - 5.84 (m, 2H), 5.33 (s, 1H), 5.13 - 4.94 (m, 4H), 3.45 (d, J = 6.3, 2H), 3.29 (d, J = 6.7, 2H), 3.01 (t, J = 7.3, 2H), 2.56 - 2.24 (m, 5H). 13C NMR (101 MHz, CDCl3) delta 154.63, 151.64, 140.38, 138.27, 137.26, 132.32, 131.45, 130.77, 130.69, 129.41, 129.34, 128.98, 128.58, 128.42, 128.13, 126.21, 116.38, 116.32, 115.91, 113.64, 77.87, 46.83, 39.85, 35.19, 35.13, 33.56, 21.50, 14.65.
  • 15
  • [ 42142-52-9 ]
  • [ 35354-74-6 ]
  • [ 1356708-55-8 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 - 80℃; for 17h; Example 4 3,5'-Diallyl-2'-[3-(methylamino)-1-phenylpropoxy]biphenyl-4-ol hydrochloride Triphenylphosphine (0.740 g, 2.81 mmol) was dissolved in dry toluene (15 mL) and the solution was cooled down to 0 C. A solution of DEAD (~40% in toluene, 1.29 mL, 2.81 mmol) was added dropwise and the mixture was stirred for 5 min. a-[2-(Methylamino)ethyl]benzyl alcohol was then added (0.372 g, 2.25 mmol), followed by the addition of honokiol (0.5 g, 1.87 mmol). The solution was stirred at 0 C for 1 h and at 80 C for 16 h. The crude mixture was diluted with EtOAc and washed with 10% aqueous HCI (x3). The combined organic fractions were dried (MgS04), filtered, and evaporated to dryness. The resulting syrup was purified by column chromatography (SiO2, EtOAc/MeOH 0-20%). The desired compound was obtained as a yellow solid in 5% yield (0.043 g, 0.095 mmol), and the product described in Example 8 was also isolated. 1H NMR (200 MHz, CDCl3) delta 7.42-6.76 (m, 10H), 6.54 (d, J = 8.4, 1H), 6.20 - 5.74 (m, 2H), 5.23 - 4.92 (m, 5H), 3.46 (d, J = 6.7, 2H), 3.29 (d, J = 6.6, 2H), 3.06 - 2.10 (m, 7H). 13C NMR (101 MHz, CDCl3) delta 154.38, 152.43, 139.95, 137.56, 136.97, 133.52, 131.49, 131.21, 130.91, 129.81, 129.12, 128.67, 128.33, 128.05, 127.27, 125.77, 116.14, 115.90, 114.48, 79.83, 47.09, 39.48, 34.59, 34.40, 33.53.
  • 16
  • [ 911812-86-7 ]
  • 3,3'-diallyl biphenyl-2,4'-diol [ No CAS ]
  • [ 35354-74-6 ]
YieldReaction ConditionsOperation in experiment
40%; 60% for 1.33333h;Microwave irradiation; Heating; Sealed tube; A solution of bis-O-allylbiphenyl ether9(0.133 g, 0.5 mmol) inN,N-diethylaniline (1 mL) was subjected to microwaveirradiation for 40 min at 180C in a sealed tube. After 10 min interval, thereaction was again exposed to microwave irradiation for another 40 min at180C. After completion, as indicated by TLC, the solvent was evaporatedunder reduced pressure and the residue was diluted with water and extractedwith EtOAc. The combined organic layers were washed with brine solution,dried over anhydrous Na2SO4, and concentrated under reduced pressure togive the crude residue which was purified by silica gel columnchromatography (EtOAc/hexanes, 1:10) to afford the honokiol (1a) (0.045 g)in 60% yield and 3,30diallylbiphelyl-2,40-diol (1b) (0.03 g) in 40% yield.
40%; 60% at 180℃; for 1.33333h;Microwave irradiation; A solution of bis-O-allylbiphenyl ether 9(0.133 g, 0.5 mmol) in N,N-diethylaniline (1 mL) was subjected to microwaveirradiation for 40 min at 180 C in a sealed tube. After 10 min interval, thereaction was again exposed to microwave irradiation for another 40 min at180 C. After completion, as indicated by TLC, the solvent was evaporatedunder reduced pressure and the residue was diluted with water and extractedwith EtOAc. The combined organic layers were washed with brine solution,dried over anhydrous Na2SO4, and concentrated under reduced pressure togive the crude residue which was purified by silica gel columnchromatography (EtOAc/hexanes, 1:10) to afford the honokiol (1a) (0.045 g)in 60% yield and 3,30 diallylbiphelyl-2,40-diol (1b) (0.03 g) in 40% yield.
55%; 40% at 190℃; for 12h;Sealed tube; A solution of bis-Oallylbiphenyl ether 9 (1.64 g, 6 mmol), in N,N-diethylaniline (12 mL) wasstirred at 190C for 12 h in a sealed tube. After completion, the solvent wasevaporated under reduced pressure and the residue was diluted with waterand extracted with EtOAc. The combined organic layers were washed withbrine solution, dried over anhydrous Na2SO4, and concentrated under reducedpressure to give the crude residue, which was purified by silica gel columnchromatography (EtOAc/hexanes, 1:10) to afford the honokiol (1a) (0.62 g) in40% yield and isohonokiol (1b) (0.85 g) in 55% yield.Compound 1a:Solid, mp 83-86C. IR (CHCl3):mmax3523, 3077, 2978, 2914,1638, 1607, 1505, 1455, 1326, 1209, 915, 785, 749 cm1;1H NMR (500 MHz,CDCl3): d7.22 (dd,J= 8.1, 2.3 Hz, 1H), 7.05 (dd,J= 8.2, 2.3 Hz, 1H), 7.02 (d,J= 2.1 Hz, 1H), 6.93 (d,J= 3.8 Hz, 1H), 6.90 (d,J= 8.2 Hz, 1H) 5.93-6.08 (m, 2H),5.17-5.24 (m, 3H), 5.03-5.11 (m, 3H) 3.46 (d,J= 6.4 Hz, 2H), 3.35 (d,J= 6.7 Hz,2H);13C NMR (75 MHz, CDCl3): d153.9, 150.8, 137.8, 136.1, 132.1, 131.0,129.6, 128.7, 128.4, 127.7, 126.5, 122.4, 116.7, 116.4, 115.5, 115.4, 39.4, 34.9;HRMS (ESI): Calcd for C18H19O2([M+H]), 267.13801. Found: 267.13796.3,30-Diallylbiphelyl-2,4?-diol (1b):Yield 55% (mg), solid, mp 65-68C. IR (CHCl3):mmax3523, 3077, 2978, 2914, 1638, 1607, 1505, 1455, 1326, 1209, 915, 785,749 cm1;1H NMR (300 MHz, CDCl3): d 7.23 (t, J= 7.5 Hz, 2H), 7.10 (t,J= 6.7 Hz, 2H), 6.92 (t,J= 7.5 Hz, 2H), 5.96-6.14 (m, 2H), 5.06-5.38 (m, 4H),3.46 (d,J= 6.0 Hz, 4H), 1.62 (br s, 2H);13C NMR (75 MHz, CDCl3): d153.7,150.3, 136.6, 135.9, 131.2, 129.6, 129.3, 128.5, 128.2, 127.8, 126.4, 120.3, 116.7,116.4, 115.7, 34.9, 34.7; HRMS (ESI): Calcd for C18H19O2([M+H]), 267.13801.Found: 267.13796.
55%; 40% at 190℃; for 12h;Sealed tube; A solution of bis-Oallylbiphenylether 9 (1.64 g, 6 mmol), in N,N-diethylaniline (12 mL) wasstirred at 190 C for 12 h in a sealed tube. After completion, the solvent wasevaporated under reduced pressure and the residue was diluted with waterand extracted with EtOAc. The combined organic layers were washed withbrine solution, dried over anhydrous Na2SO4, and concentrated under reducedpressure to give the crude residue, which was purified by silica gel columnchromatography (EtOAc/hexanes, 1:10) to afford the honokiol (1a) (0.62 g) in40% yield and isohonokiol (1b) (0.85 g) in 55% yield.

  • 17
  • [ 68592-18-7 ]
  • [ 35354-74-6 ]
YieldReaction ConditionsOperation in experiment
97% With aluminum (III) chloride; at -5 - 0℃; for 0.333333h; The solution of 30,5-diallyl-2,40-dimethoxy biphenyl 3 (0.5 g, 1.69 mmol) in DMS (2 ml) was added slowly to asolution of AlCl3 (678 mg, 5 mmol) in DMS (15 ml) at 5 C and the temperature was maintained between 5 and 0 C for 20 min. The reactionwas then poured in ice cold water and extracted with EtOAc (20 ml 3),washed with H2O (10 ml), dried over anhydrous Na2SO4, and concentrated invacuo. Crystallization of the residue in ethyl acetate/hexane (3:7) afforded 1 inquantitative yield 97% (0.44 g). 1H NMR (200 MHz, CDCl3): d 3.37 (d, J = 6.4 Hz,2H), 3.48 (d, J = 6.3 Hz, 2H), 5.03-5.24 (m, 4H), 5.98-6.06 (m, 2H), 6.90-6.94(m, 2H), 7.08 (d, J = 8.4 Hz, 2H), 7.3 (d, J = 7.1 Hz, 2H); 13C NMR (125 MHz,CDCl3): 151.09, 137.58, 133.24, 131.39, 131.16, 130.28, 129.87, 128.84, 128.54,116.75, 115.84, 115.64, 39.37, 35.08; ESI-MS: 266 (M+).
95% With boron tribromide-dimethyl sulfide complex; In 1,2-dichloro-ethane; at 65℃; for 15h;Inert atmosphere; To a solution of Compound V (400 mg, 1.36 mmol) in distilled 1,2-dichloroethane (7 mL) was slowly added BBr3.DMS complex (1.0 g, 3.26 mmol). The reaction flask was sealed under an argon atmosphere and heated to 65 C. for 15 h. The reaction was quenched with saturated NaHCO3 solution (15 mL) and extracted with dichloromethane (15 mL*3). The combined organic layers were washed with brine (15 mL), dried over Na2SO4, and filtered. The solvent was concentrated by rotary evaporation and the residue was purified by column chromatography (silica) with 20% ethyl acetate/hexane as eluent to give honokiol (345 mg, 1.29 mmol, 95% yield) as a white solid; 1H NMR (500 MHz, CDCl3) delta 7.23 (dd, J=8.0 Hz, 2.0 Hz, 1H), 7.21 (d, J=2.1 Hz, 1H), 7.05 (dd, J=8.0 Hz, 2.0 Hz, 1H), 7.02 (d, J=2.1 Hz, 1H), 6.93 (d, J=8.2 Hz, 1H), 6.90 (d, J=8.2 Hz, 1H), 5.93-6.08 (m, 2H), 5.17-5.24 (m, 3H), 5.03-5.11 (m, 3H) 3.46 (d, J=6.5 Hz, 2H), 3.35 (d, J=6.7 Hz, 2H); 13C NMR (125 MHz, CDCl3) delta 153.9, 150.7, 137.8, 136.0, 132.2, 131.1, 130.2, 129.6, 128.8, 128.6, 127.7, 126.4, 116.9, 116.6, 115.6, 115.5, 39.4, 35.1; HRMS (ESI) m/z=265.1229 calcd for C18H17O2 [M-H]-. found 265.1223.
57.8% To a schlenk tube with 18 (0.015 g, 0.051 mmol, 1.0 equiv) in DCM (0.05 ml) was added BARF (0.0026 g, 0.0051 mmol, 10 mol%) followed by triethyl silane (0.025 ml, 0.154 mmol, 3.0 equiv). The reaction mixture was stirred for 20 minutes at room temperature before it was quenched with Et3N (0.05 ml). The reaction mixture was then filtered through celite and concentrated in vacuo. The crude silyl ether was then transferred to a schlenk tube with THF (1.0 ml) and then TBAF (0.462 ml, 0.462 mmol, 9.0 equiv) was added and the reaction mixture was stirred at room temperature for 30 minutes. The reaction was quenched with H2O and extracted three times with EtOAc. The organic extracts were dried over MgSO4, filtered through celite, and concentrated in vacuo. Purification by column chromatography on silica (10:1 hexanes:ethyl acetate) gave 1 (0.0077 g, 57.8 %) as a white crystalline solid. Spectral data for our sample matched that reported in the literature:6 1H NMR (500 MHz, Chloroform-d) delta 7.38 - 7.12 (m, 2H), 7.08 - 6.98 (m, 2H), 6.91 (dd, J = 9.7, 8.1 Hz, 2H), 6.12 - 5.91 (m, 2H), 5.26 - 5.15 (m, 2H), 5.13 - 5.02 (m, 2H), 3.46 (dt, J = 6.5, 1.6 Hz, 2H), 3.35 (m, 2H).
  • 18
  • [ 35347-50-3 ]
  • [ 35354-74-6 ]
YieldReaction ConditionsOperation in experiment
9.7 mg With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 14h; General procedure: To a solution of 3 (15.6 mg, 36.6 lmol), allylboronic acid pinacol ester (41.5 lL,220 lmol), and CsF (22.3 mg, 146 lmol) in THF (1.00 mL) was added Pd(PPh3)4(8.5 mg, 7.36 lmol). The reaction was stirred at 70 C for 16 h, the reactionmixture was filtered through Celite 535RVS and concentrated in vacuo. Theresidue (55.7 mg) was dissolved in THF (5.00 mL). LiAlH4 (55.7 mg, 1.47 mmol)was added to the reaction mixture at 0 C. The reaction mixture was stirred for14 h at the same temperature. The reaction was quenched with aq. potassiumsodium tartrate solution and then extracted with EtOAc, washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified by SiO2column chromatography eluted with hexane/EtOAc (4:1) to give honokiol(9.7 mg) as a colorless solid. The spectral data (1H NMR, 13C NMR, IR, MS) ofsynthesized 1 was identical to those of the natural product and previoussynthesized 1
  • 19
  • [ 611-62-1 ]
  • [ 35354-74-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: bromine; carbon disulfide / 14 h / 0 °C 2: pyridine / 10 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / tetrahydrofuran / 16 h / 70 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 0.17 h / 20 °C 1.2: 18 h / 20 °C 2.1: acetic acid; dihydrogen peroxide / water / 0.5 h / 0 °C 2.2: 5 h / 0 - 20 °C 3.1: palladium diacetate; XPhos / tetrahydrofuran / 0.5 h / 20 °C 3.2: 17 h / 40 °C 4.1: boron tribromide-dimethyl sulfide complex / 1,2-dichloro-ethane / 15 h / 65 °C / Inert atmosphere
  • 20
  • [ 35354-74-6 ]
  • [ 1416567-14-0 ]
YieldReaction ConditionsOperation in experiment
86% With oxygen; sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; water; at 60℃; under 6080.41 Torr; for 16h;Autoclave; Was added to the autoclave 10mmol honokiol, 0.2mmolPdCl2,2.0mmolNaOAc, 56ml DMA / H2O (6: 1), through 8atmO2, reaction at 60 16h. After completion of the reaction, diluted with 100ml of water was added and extracted with 3 × 30 ml of ethyl acetate, dried over anhydrous Na2SO4, evaporated under reduced pressure to recover the solvent. The crude product is purified by column chromatography, a yellow oily liquid 4-allyl-2- (2-methyl-5-yl) phenol, a yield of 86.0%.
86% With oxygen; sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; water; at 60℃; under 6080.41 Torr; for 16h;Autoclave; Join 10mmol honokiol in the autoclave, 0.2mmolPdCl2, 2.0mmolNaOAc, 56ml DMA / H2O (6: 1), through 8atmO2, Reaction at 60 16h.After completion of the reaction, diluted with 100ml of water was added and extracted with 3 × 30 ml of ethyl acetate, dried over anhydrous Na2SO4Dried and evaporated under reduced pressure to recover the solvent.The crude product is purified by column chromatography, a yellow oily liquid 4-allyl-2- (2-methyl-5-yl) phenol, a yield of 86.0%.
86% With oxygen; sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; water; at 60℃; under 6080.41 Torr; for 16h;Autoclave; 15mmol and magnolol, 0.225 mmol of PdCl 2 , 1.5 mmol of NaOAc, dissolved in 56 mL of DMA/H 2 O (6:1), charged with 8 atm O 2 in an autoclave, and reacted in an oil bath at 60 C for 16 h. After the reaction was completed, the reaction solution was transferred to a sep. funnel, diluted with 100 mL of H 2, and extracted three times with ethyl acetate. The organic layer was combined, dried over anhydrous Na?SO? The crude product is purified by column chromatography. Obtaining a yellow oily liquid 4-allyl-2-(2-methylbenzofuran-5-yl)phenol in a yield of 86%.
86% With oxygen; sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; water; at 60℃; under 6080.41 Torr; for 16h;Autoclave; 15mmol of magnolol, 0.225 mmol of PdCl2, 1.5 mmol of NaOAc, dissolved in 56 mL of DMA/H 2 O (6:1) and fill the autoclave with 8 atm O2. The reaction was carried out in a 60 C oil bath for 16 h. After the reaction was completed, The reaction solution was transferred to a separatory funnel and diluted with 100 mL of H2O. extracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous Na2SO4, otary evaporated to recover the solvent. The crude product is purified by column chromatography to obtaining a yellow oily liquid 4-allyl-2-(2-methylbenzofuran-5-yl)phenol in a yield of 86%
86% With oxygen; sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; water; at 60℃; under 6080.41 Torr; for 16h;Autoclave; 15 mmol of honokiol, 0.225 mmol PdCl 2 , 1.5 mmol NaOAc, dissolved in 56 mL DMA/H 2 O (6:1),The autoclave was charged with 8 atm O2 and reacted in a 60 C oil bath for 16 h.After the reaction, the reaction solution was transferred to a separatory funnel and diluted with 100 mL of H2O.The organic layer was combined and dried over anhydrous Na 2SO.The crude product is purified by column chromatography to obtain a yellow oily liquid.4-allyl-2-(2-methylbenzofuran-5-yl)phenol, yield 86%;
86% With oxygen; sodium acetate; palladium dichloride; In water; N,N-dimethyl-formamide; at 60℃; under 6080.41 Torr; for 16h;Autoclave; 15 mmol honokiol, 0.225 mmol PdCl2, 1.5 mmol NaOAc, with 56 mL DMA/H2O (6: 1) was dissolved, in an autoclave charged with 8 atm O2 , 60 C reaction in an oil bath 16 h. Completion of thereaction, the reaction solution was transferred to a separatory funnel, add 100 mL H 2 O was diluted, andextracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous Na 2 SO 4Drying, rotary evaporation to recover the solvent. The crude product is purified by column chromatography, a yellow oily liquid to give 4-allyl-2-(2-methylbenzofuran-5-yl)phenol, yield 86% ;
86% With sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; water; at 60℃; for 16h; A mixture of honokiol (10mmol), NaOAc (1mmol) and PdCl2 (0.15mmol) in the cosolventof DMA and H2O (35ml, v/v6:1) was stirred under O2 (0.8Mpa) at 60 C for16 h. After cooling, the mixture was diluted with water and extracted with ethyl acetate.The combined extracts were dried over Na2SO4 and concentrated under reduced pressure.The residue was then purified by silica gel chromatography (petroleum ether/ethylacetate8/1, v/v) to afford 4 as light yellow oil. Yield 86%; 1H NMR (400MHz, CDCl3)d 7.53 (d, J1.5Hz, 1H, benzofuran 4-H), 7.50 (d, J8.4Hz, 1H, benzofuran 7-H),7.26 (dd, J8.4, 1.5Hz, 1H, benzofuran 6-H), 7.10-7.07 (m, 2H, C6H3 3,5-H), 6.94 (d,1H, J8.8Hz, C6H3 6-H), 6.41 (s, 1H, benzofuran 3-H), 6.04-5.93 (m, 1H,CH2CHCH2), 5.21 (s, 1H, OH), 5.12-5.04 (m, 2H, CH2CHCH2), 3.36 (d,J6.7Hz, 2H, CH2CHCH2), 2.49 (s, 3H, CH3); 13C NMR (101MHz, CDCl3) d156.6, 154.4, 151.1, 138.1, 132.3, 131.8, 130.8, 130.2, 129.0, 128.8, 124.4, 120.9, 116.0,115.8, 111.3, 102.9, 39.6, 14.2. LC-MS m/z: 265.1 [MH]. Elemental analysis: Found:C, 81.85%, H, 6.08%; calcd for C18H16O2, C, 81.79%, H, 6.10%.
86% With oxygen; sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; water; at 60℃; under 6080.41 Torr; for 16h;Autoclave; 15mmol honokiol, 0.225mmol PdCl2, 1.5mmol NaOAc, dissolved with 56mLDMA / H2O (6: 1), filled with 8atm O2 in the autoclave, reacted at 60 oil bath for 16h. After the reaction was completed, the reaction solution was transferred to a separatory funnel, diluted with 100 mL of H2O, extracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous Na2SO4, and the solvent was recovered by rotary evaporation. The crude product was purified by column chromatography to obtain 4-allyl-2-(2-methylbenzofuran-5-yl)phenol as a yellow oily liquid with a yield of 86%
86% With oxygen; sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; at 60℃; under 6080.41 Torr; for 16h;Autoclave; 15mmolwithMagnolol,0.225mmol PdCl2,1.5mmol NaOAc,Dissolve with 56mL DMA / H2O (6: 1),Fill 8atm O2 in high pressure reactor,The reaction was carried out in an oil bath at 60 C for 16h.After the reaction,Transfer the reaction solution to a separatory funnel, dilute with 100mL H2O,Extract 3 times with ethyl acetate,Combine organic layers, Dried with anhydrous Na2SO4,Rotate the solvent to recover it.The crude product is purified by column chromatography,To obtain a yellow oily liquid 4-allyl-2- (2-methylbenzofuran-5-yl) phenol,The yield is 86%;
85% With oxygen; sodium acetate; palladium dichloride; In N,N-dimethyl acetamide; water; at 60℃; under 6000.6 Torr; for 16h; A mixture of honokiol (10 mmol), NaOAc (1 mmol) and PdCl2 (0.15 mmol) in the co-solvent of DMA and H2O (35 mL, v/v=6:1) was stirred under O2 (0.8 Mpa) at 60 C for 16 h. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The combined extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was then purified by silica gel chromatography to afford C3 as light yellow oil (85%). 1H NMR (400 MHz, CDCl3) delta: 7.53 (d, J = 1.5 Hz, 1H, benzofuran 4-H), 7.50 (d, J = 8.4 Hz, 1H, benzofuran 7-H), 7.26 (dd, J = 8.4, 1.5 Hz, 1H, benzofuran 6-H), 7.10-7.07 (m, 2H, Ar-H), 6.94 (d, 1H, J = 8.8 Hz, Ar-H), 6.41 (s, 1H, benzofuran 3-H), 6.04-5.93 (m, 1H, CH2CH=CH2), 5.21 (s, 1H, OH), 5.09 (dd, J = 23.1, 5.9 Hz, 2H, CH2CH=CH2), 3.36 (d, J = 6.7 Hz, 2H, CH2CH=CH2), 2.49 (s, 3H, CH3); 13C NMR (101 MHz, CDCl3) delta: 156.58, 154.44, 151.10, 138.08, 132.29, 131.79, 130.83, 130.21, 129.00, 128.75, 124.43, 120.87, 115.98, 115.75, 111.34, 102.93, 39.61, 14.19. LC-MS, m/z: 265.1 [M+H]+ . Elemental anal.(%) calcd. for C18H16O2: C 81.79, H 6.10; Found: C 81.85, H 6.08.

  • 21
  • [ 35354-74-6 ]
  • [ 98-88-4 ]
  • 3',5-diallyl-2,4'-diphenylformyloxybiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
98.4% With dmap; triethylamine; In dichloromethane; at 20℃; for 1h;Cooling with ice; <strong>[35354-74-6]Honokiol</strong> 20mmol, 60mmol triethylamine, 2mmolDMAP and 40ml of methylene chloride in an ice bath under a 71/92 44mmol benzoyl chloride, 1h dropping was completed, the mixture was stirred at room temperature 0.5H; 40ml of water was added, liquid separation, the organic layer was washed with 2 × 20ml washed with water, dried over anhydrous Na2SO4Dried and distilled under reduced pressure to give a yellow-brown oily liquid 3 ', 5-diallyl-2,4'-dibenzoyl biphenyl, yield 98.4%
  • 22
  • [ 35354-74-6 ]
  • honokiol disulfate disodium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Add 10 g of honokiol to 10 ml of pyridine, 17 g (3 equivalents) of pyridine sulfur trioxide complex, stir at room temperature overnight, concentrate under reduced pressure, add 50 ml of dilute acid water, 100 ml of ethyl acetate, extract three times, ethyl acetate The layer was dried and concentrated to dryness to give a white solid.The solid was dispersed in acetone, sodium methoxide was added, and a solid was obtained by filtration. It is the honokiol disulfate disodium salt (Id).
  • 23
  • [ 35354-74-6 ]
  • C18H17IO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.87% With iodine; In ethanol; water; at 50℃; for 12h; A mixture of honikiol 1 (532 mg, 2.0 mmol) and iodine (609 mg, 2.4 mmol) in ethanol/water (40 ml, 1:9, v/v) was stirred at 50 oC for 12 h. After the reaction was complete detected by TLC, the reaction mixture was extracted with ethyl acetate (3 × 10 ml). The combined organic layers were washed with sodium thiosulfate solution (2 × 10 ml) and brine (10 ml), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (petroleum ether /EtOAc = 30:1 to 7:1) to give intermediate 5 (499 mg, 1.27 mmol, 65.87%) as a deep yellow oil: 1H NMR (400 MHz, DMSO-d6) delta 9.22 (s, 1H), 7.35 (d, J = 1.1 Hz, 1H), 7.24 (dd, J = 8.3, 1.8 Hz, 1H), 6.99 (d, J = 2.1 Hz, 1H), 6.91 (dd, J = 8.2, 2.2 Hz, 1H), 6.83 (d, J = 8.2 Hz, 1H), 6.77 (d, J = 8.3 Hz, 1H), 6.00 - 5.88 (m, 1H), 5.10 - 4.97 (m, 2H), 4.88 - 4.79 (m, 1H), 3.63 - 3.50 (m, 2H), 3.38 (dd, J = 16.1, 9.1 Hz, 1H), 3.28 (d, J = 6.7 Hz, 2H), 2.95 (dd, J = 16.1, 7.1 Hz, 1H); 13C NMR (101 MHz, DMSO) delta 158.14, 152.82, 138.78, 131.67, 130.71, 130.61, 129.27, 128.13, 126.54, 126.24, 116.39, 115.74, 108.77, 81.77, 39.25, 36.16, 12.09; Exact mass calcd for C18H17IO2 [M+Na]+: 415.0273; found 415.0169.
  • 24
  • [ 50-00-0 ]
  • [ 35354-74-6 ]
  • [ 1333391-05-1 ]
YieldReaction ConditionsOperation in experiment
63.15% With sodium hydroxide; In water; at 20℃; for 24h; <strong>[35354-74-6]Honokiol</strong> (133.2 mg, 0.5 mmol) was added to the mixture of 37% aqueous formaldehyde solution (0.3 ml), sodium hydroxide (20.0 mg, 0.5 mmol) and H2O (3 ml). Then reaction mixture was stirred for 24 hours at r.t. The reaction mixture was neutralized and diluted with saturated sodium bicarbonate solution, which then was extracted with ethyl acetate and the extract was dried with sodium sulfate. And the organic layer was concentrated using a rotary evaporator under reduced pressure and subjected to column chromatography (petroleum ether /ethyl acetate = 10:1 to 3:1). The product was isolated and a yellow solid was obtained (103.1 mg, 0.32 mmol, 63.15%): 1H NMR (400 MHz, CDCl3) delta 7.49 (s, 1H), 7.21 (s, 1H), 7.06 (s, 1H), 6.99 (s, 1H), 6.92 (s, 1H), 6.57 (s, 1H), 6.10 - 5.88 (m, 2H), 5.19 - 5.02 (m, 4H), 4.87 (d, J = 6.9 Hz, 2H), 4.79 (d, J = 4.6 Hz, 2H), 3.46 (d, J = 6.4 Hz, 2H), 3.32 (d, J = 6.7 Hz, 2H), 2.35 (s, 2H). MS (ES), m/z: 326.1[M + H]+.
  • 25
  • [ 35354-74-6 ]
  • [ 108-24-7 ]
  • [ 35347-50-3 ]
  • honokiol 4'-monoacetate [ No CAS ]
  • honokiol 2-monoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
16%; 36%; 12% To a solution of honokiol 2 (1 g, 3.76 mmol) in dry acetone (20 mL)potassium carbonate (0.57 g, 3.76 mmol) was added at 0 C under N2. The reaction mixturewas stirred at RT for 30 min acetic anhydride (0.42 mL g, 4.13 mmol) was added and, after stirringat rt for 1 h, the solution was filtered and rotoevaporated to obtain an viscous oil that waspurified by flash chromatography using petroleum ether:tetrahydrofurane 10:2 solution as eluentto obtain:, compound 5 (oil) (0.22 g, 16%), compound 6 (oil) (0.43 g, 36%), compound 7(oil) (0.14 g, 12%) and starting material (honokiol 2) (0.16 g, 16%).Compound 6: 1H NMR (CDCl3) delta 2.34 (s, 3H) 3.35 (m, 4H), 5.06-5.14 (series of m, 4H),5.94 (m, 2H), 6.89 (d, J = 8.4 Hz, 1H), 6.99-7-09 (series of m, 2H), 7.14 (d, J = 8.4 Hz, 1H),7.31-7-39 (series of m, 2H); 13C NMR (CDCl3) delta 20.95, 34.79, 39.38, 115.66, 115.99, 116.63,123.04, 127.33, 128.27, 129.20, 130.34, 131.20, 132.25, 132.72, 135.44, 135.55, 137.73, 148.46,150.90, 169.67; Anal. Calcd for C20H20O3: C, 77.90; H, 6.54; Found: C, 78.00; H, 6.52.
  • 26
  • [ 35354-74-6 ]
  • [ 141-75-3 ]
  • C26H30O4 [ No CAS ]
  • C22H24O3 [ No CAS ]
  • C22H24O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45%; 7%; 28% To a solution of honokiol 2 (1.0 g, 3.76 mmol) in dry acetone (30 mL)potassium carbonate (1.24 g, 9.02 mmol) was added under N2. The reaction mixture was stirredunder reflux for 30 min. Butyryl chloride (0.96 g, 9.02 mmol) was added and, after stirringunder reflux for 24 h, the solution was filtered and rotoevaporated to obtain an viscous oil thatwas purified by flash chromatography using petroleum ether: tetrahydrofurane 6: 1 mixture aseluent to obtain compound 10 (oil, 0.69 g 45%), compound 11 (oil, 0.09 g, 7%), compound 12(oil, 0.35 g 28%) and starting material (honokiol 2) (0.13 g, 13%).Compound 10 (oil): 1H NMR (CDCl3) delta 0.88 (t, J = 7.2 Hz, 3H); 1.08 (t, J = 7.2 Hz, 3H);1.61 (m, 2 H); 1.84 (m, 2H); 2.35 (t, J = 7.2 Hz, 3H); 2.58 (t, J = 7.2 Hz, 3H); 3.34 (d, J = 6.8 Hz,2H); 3.43 (d, J = 6.8 Hz, 2H); 5.12 (m, 4H); 5.96 (m, 2H); 7.05 (d, J = 8.0 Hz, 1H); 7.10 (d,J = 8.0 Hz, 1H); 7.21 (dd, J = 2.0 and 8.4 Hz, 1H); 7.23 (d, J = 2.0 Hz, 1H); 7.31 (m, 2H). 13CNMR (CDCl3) delta 13.51, 13.77, 18.24, 18.50, 34.70, 36.07, 36.16, 39.64, 116.26, 116.38, 122.29,122.83, 128.04, 128.65, 130.93, 130.96, 131.60, 134.03, 135.52, 135.77, 137.01, 138.03, 146.10,146.42, 171.88, 172.08. Anal. Calcd for C26H30O4 C, 76.82; H, 7.44; Found: C, 76.86; H, 7.42.
  • 27
  • [ 35354-74-6 ]
  • C23H23ClNO4(1+)*Cl(1-) [ No CAS ]
  • C41H40NO6(1+)*Cl(1-) [ No CAS ]
  • C41H40NO6(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
31.2%; 25.1% With tetrabutyl-ammonium chloride; potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 15h; (2) adding the compound of formula (III) to a clean three-necked flask,The molar ratio of the compound of formula (III) to the compound of formula (II) is 2:1,Add DMF, anhydrous potassium carbonate and tetrabutylammonium chloride,The molar ratio of DMF to the compound of formula (II) is 250:1,The molar ratio of anhydrous potassium carbonate added to the compound of formula (II) is 20:1,The molar ratio of tetrabutylammonium chloride added to the compound of formula (II) is 1:1;The reaction was carried out at a temperature of 70 C for 15 hours.After the reaction is finished, it is cooled, filtered, and dried.Further purification,That is, the compounds of the formulae (IV) and (V) of the present invention are obtained. The compound of the formula (IV) prepared by the method of the present example has a yield of 31.2% and a purity of 90%;The compound of the formula (V) had a yield of 25.1% and a purity of 87%.
  • 28
  • [ 35354-74-6 ]
  • C23H23INO4(1+)*Cl(1-) [ No CAS ]
  • C41H40NO6(1+)*Cl(1-) [ No CAS ]
  • C41H40NO6(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
34.1%; 32.1% With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In dichloromethane; at 30℃; for 15h; (2) adding the compound of formula (III) to a clean three-necked flask,The molar ratio of the compound of formula (III) to the compound of formula (II) is 4:1,Add dichloromethane,Anhydrous potassium carbonate and benzyltriethylammonium chloride (TEBA),The molar ratio of the added dichloromethane to the compound of formula (II) is 200:1,The molar ratio of anhydrous potassium carbonate added to the compound of formula (II) is 8:1,The molar ratio of benzyltriethylammonium chloride (TEBA) to the compound of formula (II) is 2:1;The reaction was carried out at a temperature of 30 C for 15 hours.After the reaction is completed, it is cooled, suction filtered, dried, and further purified.That is, the compounds of the formulae (IV) and (V) of the present invention are obtained. The compound of the formula (IV) prepared by the method of the present example has a yield of 34.1% and a purity of 87%;The compound of the formula (V) had a yield of 32.1% and a purity of 89%.
  • 29
  • 9-(4-bromo-butoxy)-10-methoxy-5,6-dihydro-[1,3]dioxolo[4,5-<i>g</i>]isoquino[3,2-<i>a</i>]isoquinolin-7-ylium; chloride [ No CAS ]
  • [ 35354-74-6 ]
  • C41H40NO6(1+)*Cl(1-) [ No CAS ]
  • C41H40NO6(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
45.5%; 35.5% With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; at 80℃; for 12h; (2) adding the compound of formula (III) to a clean three-necked flask,The molar ratio of the compound of formula (III) to the compound of formula (II) is 1:1,Add acetonitrile solution,Anhydrous potassium carbonate and tetrabutylammonium bromide (TBAB),The molar ratio of acetonitrile added to the compound of formula (II) is 200:1,The molar ratio of anhydrous potassium carbonate added to the compound of formula (II) is 5:1,The molar ratio of tetrabutylammonium bromide (TBAB) to the compound of formula (II) is 0.5:1;The temperature was raised to 80 C for 12 hours.After the reaction is completed, it is cooled, suction filtered, dried, and further purified.That is, the compounds of the formulae (IV) and (V) of the present invention are obtained. The compound of the formula (IV) prepared by the method of the present example has a yield of 45.5% and a purity of 93%;The compound of the formula (V) had a yield of 35.5% and a purity of 91%.
  • 30
  • [ 50-00-0 ]
  • [ 35354-74-6 ]
  • [ 75-04-7 ]
  • C26H32N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.5% In 1,4-dioxane; toluene; at 120℃; for 24h; (1) 1 mol of honokiol,2 mol of ethylamine and 6.1 mol of paraformaldehyde,Dissolved in a mixed solution of 550 mL of dioxane and toluene (the ratio of dioxane to toluene was 4:1), and reacted at 120 C for 24 hours.Rotary evaporation under reduced pressure to remove the mixed solvent.After washing with water and drying, a honokiol ethylamine benzoxazine having the structure shown in formula (II-2) is obtained.The yield was 95.5%.
  • 31
  • [ 50-00-0 ]
  • [ 111-26-2 ]
  • [ 35354-74-6 ]
  • C34H48N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.5% In 1,4-dioxane; toluene; at 110℃; for 43h; (1) 1 mol of honokiol,2 mol of hexylamine and 6.1 mol of paraformaldehyde,Dissolved in a mixed solution of 560 mL of dioxane and toluene (the ratio of dioxane to toluene was 4:3), and reacted at 110 C for 43 hours.Rotary evaporation under reduced pressure to remove the mixed solvent.After washing with water and drying, a honoki hexylamine benzoxazine having the structure shown in formula (II-3) is obtained.The yield was 95.5%.
  • 32
  • [ 50-00-0 ]
  • [ 35354-74-6 ]
  • [ 62-53-3 ]
  • C34H32N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93.6% In 1,4-dioxane; toluene; at 100℃; for 58h; (1) 1 mol of honokiol,2 mol of aniline and 8.1 mol of paraformaldehyde,Dissolved in a mixed solution of 510 mL of dioxane and toluene (the ratio of dioxane to toluene was 6:5), and reacted at 100 C for 58 hours.Rotary evaporation under reduced pressure to remove the mixed solvent.After washing with water and drying, a honokiline aniline benzoxazine having the structure shown in formula (II-4) is obtained.The yield was 93.6%.
  • 33
  • [ 50-00-0 ]
  • [ 617-89-0 ]
  • [ 35354-74-6 ]
  • C32H32N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.8% In 1,4-dioxane; toluene; at 100℃; for 52h; (1) 1 mol of honokiol,2 mol of furfurylamine and 7.5 mol of paraformaldehyde,Dissolved in a mixed solution of 650 mL of dioxane and toluene (the ratio of dioxane to toluene was 3:1), and reacted at 100 C for 52 hours.Rotary evaporation under reduced pressure to remove the mixed solvent.After washing with water and drying, a honokiol benzoxazine represented by the formula (II-1) is obtained.The yield was 90.8%. 1H-NMR of 1H NMR spectrum is shown in Figure 2.Each peak on the graph has a one-to-one correspondence with the hydrogen atom on the structure of the honokiol benzoxazine compound.
  • 34
  • [ 35354-74-6 ]
  • 4-allyl-2-(2-methyl-2,3-dihydrobenzofuran-5-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With sulfuric acid; In dichloromethane; at 50℃; for 24h; To a stirred solution of honokiol (10 mmol) in 1,2-dichloroethane (40 mL) was added concentrated sulfuric acid (98%, 0.2 mL) dropwise at room temperature. Then the mixture was heated to 50 C and stirred for 24 h. After cooling, the solvent was evaporated under reduced pressure and the residue was then purified by silica gel chromatography to afford C1 as light yellow oil (12%). 1H NMR (400 MHz, CDCl3) delta 7.22 (s, 1H, Ar-H), 7.17 (d, J = 8.1 Hz, 1H, Ar-H), 7.03-7.01 (m, 2H, Ar-H), 6.87 (d, J = 8.1 Hz, 1H, Ar-H), 6.82 (d, J = 8.1 Hz, 1H, Ar-H), 5.96 (dt, J = 16.6, 6.9 Hz, 1H, CH2CH=CH2), 5.26 (s, 1H, OH), 5.11-5.01 (m, 2H, CH2CH=CH2), 4.99-4.91 (m, 1H, CH3CHCH2), 3.36-3.29 (m, 3H, CH2CH=CH2 and CH3CHCH2), 2.83 (dd, J = 15.5, 7.6 Hz, 1H, CH3CHCH2), 1.47 (d, J = 6.2 Hz, 3H, CH3CHCH2); 13C NMR (101 MHz, CDCl3) delta 159.36, 150.92, 137.88, 132.18, 130.38, 129.15, 128.96, 128.67, 128.33, 128.27, 125.95, 115.64, 115.60, 109.88, 80.11, 39.48, 37.10, 21.85. LC-MS, m/z: 267.2 [M+H]+ . Elemental anal.(%) calcd. for C18H18O2: C 81.17, H 6.81; Found: C 81.20, H 6.83.
  • 35
  • [ 35354-74-6 ]
  • [ 106-96-7 ]
  • 2-propargyl honokiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% With caesium carbonate; potassium iodide; In acetone; at 20℃; for 6h; <strong>[35354-74-6]Honokiol</strong>(3 g, 11.3 mmol) was dissolved in acetone,Cs2CO3 (5.5 g, 16.89 mmol), propargyl bromide (1.18 mL, 11.26 mmol) and KI (0.37 g, 2.25 mmol) were added and reacted at room temperature for 6 hours. Water was then added to terminate the reaction. After work-up using dichloromethane (DCM), the obtained organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by silica column chromatography (EA: HEX = 1: 9 v: v, Rf = 0.5) to obtain Compound A1 (260 mg, 8% yield).
  • 36
  • [ 35354-74-6 ]
  • [ 106-96-7 ]
  • 4'-propargyl honokiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% With caesium carbonate; potassium iodide; In acetone; at 20℃; for 6h; <strong>[35354-74-6]Honokiol</strong> (3 g, 11.3 mmol) was dissolved in acetone and then Cs2CO3 (5.5 g, 16.89 mmol), propargyl bromide (1.18 mL, 11.26 mmol) and KI (0.37 g, 2.25 mmol) were added and reacted at room temperature for 6 hours. Terminated. After work-up using dichloromethane (DCM), the obtained organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica column chromatography (EA: HEX = 1: 9 v: v, Rf = 0.6) to give compound A2 (240 mg, 7% yield).
  • 37
  • [ 35354-74-6 ]
  • [ 106-96-7 ]
  • C24H22O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With caesium carbonate; potassium iodide; In acetone; at 20℃; for 6h; <strong>[35354-74-6]Honokiol</strong> (3 g, 11.3 mmol)Was dissolved in acetone and then Cs2CO3 (5.5 g, 16.89 mmol), propargyl bromide (1.18 mL, 11.26 mmol) and KI (0.37 g, 2.25 mmol) were added and reacted at room temperature for 6 hours. Terminated. After work-up using dichloromethane (DCM), the obtained organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by silica column chromatography (EA: HEX = 1: 9 v: v, Rf = 0.7) to obtain Compound A3 (770 mg, 20% yield).
  • 38
  • [ 35354-74-6 ]
  • [ 264882-00-0 ]
  • methyl 2-(2-chlorophenyl)-2-((5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl)oxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With sewage sludge-derived carbon material treated with perchloric acid; In 1,2-dichloro-ethane; at 70℃; for 24h; At room temperature, weighed o-chlorophenyldiazoacetate methyl ester 1b (0.5 mmol), magnolol 2a (0.70 mmol), and SW-HClO4 (50 mg) in a dry clean 25 mL Schlenk reaction tube in air. In the atmosphere,Add 5 mL of 1,2-dichloroethane, stir at room temperature for 2-5 minutes, dispose in a 70 C oil bath magnetic stirring heater for 24 hours, TLC detection of the raw material has completely reacted, stop the reaction, and cool the reaction solution To room temperature, suction filtration, filter cake washed with dichloromethane until noColor, concentrated under reduced pressure to remove volatile components, and purified by silica gel column chromatography (eluent: petroleum ether (60-90 C) / ethyl acetate, v/v = 5:1),The target product 3b (161 mg, yield 72%) was obtained as colorless, viscous.The target product was confirmed by nuclear magnetic resonance spectroscopy and gas chromatography-mass spectrometry.
  • 39
  • [ 22065-57-2 ]
  • [ 35354-74-6 ]
  • ethyl 2-((5,5'-diallyl-4'-hydroxy-[1,1'-biphenyl]-2-yl)oxy)-2-phenylacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% At room temperature, weigh phenyldiazoacetate 1a (0.5 mmol),<strong>[35354-74-6]Honokiol</strong>5b (0.8mmol) in a 25mL Schlenk reaction tube under air atmosphere,Add 5 mL of 1,2-dichloroethane, and stir at room temperature for 2 minutes. Slowly add 0.1 mmol (10 muL) of 98% trifluoromethanesulfonic acid to the micro sampler, and continue the reaction for 30 minutes.TLC detects that the raw materials have reacted completely, and stops the reaction; concentrated under reduced pressure to remove volatile components,Silica gel column chromatography(Eluent: petroleum ether (60-90 C) / ethyl acetate, v / v = 10: 1),Obtained the yellow viscous target product7a (118 mg, yield 55%), and the target product was confirmed by nuclear magnetic resonance spectrum and high resolution mass spectrometry.
With sewage sludge-derived carbon material treated with perchloric acid; In 1,2-dichloro-ethane; at 70℃; for 48h; At room temperature,Phenyl phenylEthyl diazoacetate 1e (0.5 mmol),And honokiol 2b (0.70mmol), SW-HClO4 (50mg) in a dry and clean 25mL Schlenk reaction tube, under air atmosphere,Add 5 mL of 1,2-dichloroethane, stir at room temperature for 2-5 minutes, dispose in a 70 C oil bath magnetic stirring heater for 48 hours, TLC detection of the raw material has completely reacted, stop the reaction, and cool the reaction solution At room temperature, suction filtration, filter cake washed with dichloromethane to the filtrateColorless, concentrated under reduced pressure to remove volatile components, and purified by silica gel column chromatography (eluent: petroleum ether (60-90 C) / ethyl acetate, v/v = 10:1)The objective product 4e (64 mg, yield 32%) was obtained as colorless, viscous.The target product was confirmed by nuclear magnetic resonance spectroscopy and gas chromatography-mass spectrometry.
  • 40
  • [ 35354-74-6 ]
  • 5-allyl-3'-(2,3-dihydroxypropyl)-[1,1'-biphenyl]-2,4'-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 2h; To a stirred solution of honokiol (5.0 mmol) in CH2Cl2 (10 mL) was added m-chloroperoxybenzoic acid (75%, 10 mmol) in five portions over 8 h and kept stirring for 2 h at room temperature. Then the reaction was quenched with saturated Na2SO3 solution, neutralized by NaHCO3 and extracted with CH2Cl2. The combined extracts was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in THF (10 mL) and NaOH solution (1M, 10 mL) was added. After it was stirred for 1 h at room temperature, the mixture was acidized by diluted hydrochloric acid and extracted with ethylacetate. The organic layer was dried, concentrated and purified by silica gel chromatography to afford B1 as a brown solid (38%). m.p. 32-34 C. 1H NMR (400 MHz, DMSO-d6) delta: 9.20 (s, 1H, Ar-OH), 7.33 (s, 1H, Ar-H), 7.21 (d, J = 8.2 Hz, 1H, Ar-H), 6.99 (d, J = 1.3 Hz, 1H, Ar-H), 6.90 (dd, J = 8.2, 1.3 Hz, 1H, Ar-H), 6.82 (d, J = 8.2 Hz, 1H, Ar-H), 6.73 (d, J = 8.2 Hz, 1H, Ar-H), 6.00-5.88 (m, 1H, CH2CH=CH2), 5.06 (d, J = 17.1 Hz, 1H, CH2CH=CH2), 5.01 (d, J = 9.9 Hz, 1H, CH2CH=CH2), 4.85-4.77 (m, 1H, CH2CH(OH)CH2OH), 3.63-3.55 (m, 2H, CH2CH(OH)CH2OH), 3.27 (d, J = 6.7 Hz, 2H, CH2CH=CH2), 3.21 (dd, J = 15.7, 8.3 Hz, 1H, CH2CH(OH)CH2OH), 3.00 (dd, J = 15.7, 8.3 Hz, 1H, CH2CH(OH)CH2OH); 13C NMR (101 MHz, CDCl3) delta: 158.93, 150.70, 137.68, 132.10, 130.21, 129.47, 128.95, 128.66, 127.88, 127.79, 125.92, 115.52, 115.49, 109.90, 83.44, 64.81, 39.33, 31.10. LC-MS, m/z: 301.0 [M+H]+ . Elemental anal.(%) calcd. for C18H20O4: C 71.98, H 6.71; Found: C 71.92, H 6.66.
  • 41
  • [ 35354-74-6 ]
  • 3,3'-(4,6'-dihydroxy-[1,1'-biphenyl]-3,3'-diyl)bis(propane-1,2-diol) [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% To a stirred solution of honokiol (5 mmol) in CH2Cl2 (10 mL) was added m-chloroperoxybenzoic acid (75%, 17.5 mmol) in five portions over 8 h and kept stirring for 2 h at room temperature. Then the reaction was quenched with saturated Na2SO3 solution, neutralized by NaHCO3 and extracted with CH2Cl2. The combined extracts was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in THF (10 mL) and NaOH solution (1M, 10 mL) was added. After it was stirred and refluxed for 1 h, the mixture was acidized by diluted hydrochloric acid and extracted with ethylacetate. The organic layer was dried, concentrated and purified by silica gel chromatography to afford B2 as a yellow solid (66%). m.p. 50-52 C. 1H NMR (400 MHz, DMSO-d6) delta: 9.23 (s, 1H, Ar-OH), 7.35 (s, 1H, Ar-H), 7.23 (d, J = 8.2 Hz, 1H, Ar-H), 7.05 (s, 1H, Ar-H), 6.94 (dd, J = 8.2, 1.9 Hz, 1H, Ar-H), 6.81 (d, J = 8.2 Hz, 1H, Ar-H), 6.73 (d, J = 8.2 Hz, 1H, Ar-H), 5.14 (s, 2H, OH), 4.86-4.77 (m, 1H, CH2CH(OH)CH2OH), 3.88-3.78 (m, 1H, CH2CH(OH)CH2OH), 3.61-3.58 (m, 2H, CH2CH(OH)CH2OH), 3.55 (dd, J = 11.0, 5.0 Hz, 1H, CH2CH(OH)CH2OH), 3.46 (dd, J = 11.0, 5.0 Hz, 1H, CH2CH(OH)CH2OH), 3.22 (dd, J = 15.8, 8.4 Hz, 1H, CH2CH(OH)CH2OH), 3.00 (dd, J = 15.8, 8.4 Hz, 1H, CH2CH(OH)CH2OH), 2.72 (dd, J = 13.6, 6.3 Hz, 1H, CH2CH(OH)CH2OH), 2.61 (dd, J = 13.6, 6.3 Hz, 1H, CH2CH(OH)CH2OH); 13C NMR (101 MHz, DMSO-d6) delta: 158.63, 152.67, 131.47, 131.05, 129.31, 128.94, 128.89, 127.87, 126.99, 126.20, 115.98, 108.57, 83.89, 71.69, 63.47, 49.76, 31.40. LC-MS, m/z: 335.1 [M+H]+ . Elemental anal.(%) calcd. for C18H22O6: C 64.66, H 6.63; Found: C 64.71, H 6.61.
  • 42
  • [ 35354-74-6 ]
  • 3',5-aiallyl-3,5'-dinitro-[1,1'-biphenyl]-2,4'-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With nitric acid; acetic acid; In dichloromethane; at 10 - 20℃; for 1h; To a stirred solution of honokiol (1.0 mmol) in the co-solvent of CH2Cl2 and acetic acid (20 mL, v/v=1:1) was added concentrated nitric acid (65-68%, 5.0 mL) dropwise over 30 min in an ice bath and kept stirring for 30 min at room temperature. Then the reaction was quenched with water and extracted with CH2Cl2. The combined extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was then purified by silica gel chromatography to afford A2 as a yellow solid (52%). mp: 79-81 C. 1H NMR (400 MHz, DMSO-d6) delta 10.67 (s, 1H, OH), 10.58 (s, 1H, OH), 8.06 (s, 1H, Ar-H), 7.83 (s, 1H, Ar-H), 7.71 (s, 1H, Ar-H), 7.57 (s, 1H, Ar-H), 6.07-5.94 (m, 2H, 2?CH2CH=CH2), 5.18-5.08 (m, 4H, 2?CH2CH=CH2), 3.49 (d, J = 6.4 Hz, 2H, CH2CH=CH2), 3.43 (d, J = 6.6 Hz, 2H, CH2CH=CH2); 13C NMR (101 MHz, DMSO-d6) delta 150.78, 148.98, 137.77, 137.73, 137.34, 136.51, 136.04, 135.72, 132.27, 131.54, 130.69, 127.82, 124.14, 123.97, 117.12, 38.30, 34.00. LC-MS, m/z: 357.0 [M+H]+ . Elemental anal.(%) calcd. for C18H16N2O6: C 60.67, H 4.53, N 7.86; Found: C 60.74, H 4.55, N 7.81.
  • 43
  • [ 35354-74-6 ]
  • 3',5-diallyl-3,5'-dinitroso-1,1'-biphenyl-2,4'-diphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With hydrogenchloride; sodium nitrite; In water; acetonitrile; at 20℃; for 1.5h;Cooling with ice; To a stirred solution of honokiol (10 mmol) and NaNO2 (30 mmol) in the co-solvent of MeCN and H2O (30 mL, v/v=5:1) was added concentrated hydrochloric acid (36%, 5 mL) over 1 h in an ice bath and kept stirring for 30 min at room temperature. Then the reaction was quenched with water and extracted with CH2Cl2. The combined extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was then purified by silica gel chromatography to afford A3 as a yellow solid (79%). mp: 57-59 C. 1H NMR (400 MHz, CDCl3) delta 11.04 (s, 1H, OH), 11.01 (s, 1H, OH), 8.19 (s, 1H, Ar-H), 7.97 (s, 1H, Ar-H), 7.70 (s, 1H, Ar-H), 7.46 (s, 1H, Ar-H), 6.12-5.86 (m, 2H, CH2CH=CH2), 5.20-5.13 (m, 4H, CH2CH=CH2), 3.55 (d, J = 6.6 Hz, 2H, CH2CH=CH2), 3.43 (d, J = 6.6 Hz, 2H, CH2CH=CH2); 13C NMR(101 MHz, CDCl3) delta 153.03, 151.09, 138.52, 135.71, 134.88, 133.99, 133.42, 132.2 3, 131.45, 130.27, 127.54, 124.12, 123.57, 117.49, 117.18, 38.86, 33.74. LC-MS, m/z: 325.1 [M+H]+ . Elemental anal.(%) calcd. for C18H16N2O4: C 66.66, H 4.97, N 8.64; Found: C 66.70, H 5.00, N 8.59.
  • 44
  • [ 50-00-0 ]
  • [ 35354-74-6 ]
  • [ 124-40-3 ]
  • 3',5-diallyl-3,5'-bis((dimethylamino)methyl)-[1,1'-biphenyl]-2,4'-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In methanol; water; at 20℃; for 16h; A solution of honokiol (1.0 mmol), dimethylamine (aqueous solution, 40%, 6.0 mmol) and formalin (37%, 6.0 mmol) in MeOH (5.0 mL) was stirred at room temperature for 16 h. Then the mixture was concentrated under reduced pressure and purified by silica gel chromatography to afford A8 as yellow oil (86%). 1H NMR (400 MHz, CDCl3) delta 7.30 (s, 1H, Ar-H), 7.13 (s, 1H, Ar-H), 7.03 (s, 1H, Ar-H), 6.72 (s, 1H, Ar-H), 6.13-5.91 (m, 2H, 2?CH2CH=CH2), 5.14-5.02 (m, 4H, 2?CH2CH=CH2), 3.68 (s, 2H?NCH2), 3.64 (s, 2H?NCH2), 3.45 (d, J = 6.4 Hz, 2H, CH2CH=CH2), 3.31 (d, J = 6.6 Hz, 2H, CH2CH=CH2), 2.34 (s, 6H, 2?CH3), 2.31 (s, 6H, 2?CH3); 13C NMR (101 MHz, CDCl3) delta 154.89, 153.23, 138.12, 137.47, 130.14, 130.10, 129.67, 128.94, 128.62, 127.47, 127.06, 126.32, 122.10, 120.94, 115.33, 115.03, 63.04, 44.47, 44.41, 39.54, 34.26. LC-MS, m/z: 381.1 [M+H]+ . Elemental anal.(%) calcd. for C24H32N2O2: C 75.75, H 8.48, N 7.36; Found: C 75.82, H 8.50, N 7.33.
60% Add 1 ml of hydrochloric acid with a concentration of 12 mol / L to 70 ml of methanol. Prepare a methanolic acid solution for later use.Weigh 11.3g of a 40% strength dimethylamine solution into a three-necked flask. Slowly add 10ml of 37% formaldehyde solution and stir magnetically. The controlled drop acceleration is 1ml / min, and the controlled temperature is 30-35 C. In an ice water bath, add 40 ml of the prepared methanolic acid solution to a three-necked flask. Control the drop acceleration to 4ml / min, the temperature is 2-5 C, and continue magnetic stirring for 1h. Weigh 13.3 g of honokiol (98% content) and dissolve in the remaining 30 ml of methanolic acid solution. The three-necked flask was placed in an oil bath to control the temperature to 75 C., and a methanol solution of honokiol was added, and the mixture was refluxed for 6 hours. Remove excess methanol using a rotary evaporator, Purification was performed on a 200-mesh silica gel column with ethyl acetate / acetone as eluent.The volume ratio of ethyl acetate to acetone was 4: 1, and the obtained eluates were combined and concentrated. It was then lyophilized to obtain a honokiol derivative. The yield was 60% based on honokiol in the reaction raw material.
  • 45
  • [ 35354-74-6 ]
  • [ 403-29-2 ]
  • 2-((3,5′-diallyl-2′-hydroxy-[1,1′-biphenyl]-4-yl)oxy)-1-(4-fluorophenyl)ethan-1-one [ No CAS ]
  • 2-((3′,5-diallyl-4′-hydroxy-[1,1′-biphenyl]-2-yl)oxy)-1-(4-fluorophenyl)ethan-1-one [ No CAS ]
  • C34H28F2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
32%; 10%; 18% With caesium carbonate; In tetrahydrofuran; at 20℃; for 1h;Reflux; To a Tetrahydrofuran solution (4 mL) of honokiol (140 mg,0.52 mmol) was added Cs2CO3 (0.51 g, 1.6 mmol), followedby 4-fluorophenacyl bromide (0.14 g, 0.62 mmol). After stirring1 h at ambient temperature, the reaction mixture wasdiluted in ethyl acetate, washed with water and brine, driedover MgSO4, and concentrated under reduced pressure. Theresidue was purified by flash column chromatography onsilica gel (ethyl acetate : n-hexane = 1 : 19 to 1 : 2) to afford8a (67 mg, 32%, BORSM 40%), 8b (21 mg, 10%, BORSM12%), 8c (50 mg, 18%, BORSM 22%), and recovered honokiol(27 mg). For 8a, 1H-NMR (600 MHz, CDCl3) ae: 8.09-8.06(m, 2H), 7.27 (d, J = 2.2 Hz, 1H), 7.24 (dd, J = 8.3, 2.3 Hz,1H), 7.21-7.16 (m, 2H), 7.05 (dd, J = 8.2, 2.1 Hz, 1H), 7.00 (d,J = 2.1 Hz, 1H), 6.89 (d, J = 8.2 Hz, 1H), 6.85 (d, J = 8.3 Hz,1H), 6.04-5.93 (m, 2H), 5.27 (s, 2H), 5.10-5.04 (m, 5H),3.50 (d, J = 6.6 Hz, 2H), 3.34 (d, J = 6.7 Hz, 2H); 13C-NMR(150 MHz, CDCl3) ae: 193.4, 155.5, 150.9, 137.9, 136.5, 132.4,131.3, 131.2, 131.2, 130.3, 129.1, 128.1, 127.7, 116.3, 116.3,116.2, 115.8, 115.7, 112.2, 71.3, 39.5, 34.5.; HRMS (EI) m/z:[M] Calcd for C26H23FO3 402.1631. Found 402.1635. For 8b,1H-NMR (600 MHz, CDCl3) ae: 7.95-7.92 (m, 2H), 7.33-7.30(m, 2H), 7.09-7.01 (m, 4H), 6.83 (dd, J = 8.3, 5.4 Hz, 2H),6.04-5.97 (m, 2H), 5.10-5.06 (m, 5H), 3.41 (d, J = 6.4 Hz,2H), 3.36 (d, J = 6.8 Hz, 2H); 13C-NMR (150 MHz, CDCl3)ae: 193.8, 166.9, 165.2, 153.4, 153.3, 137.5, 136.4, 131.7, 131.3,131.2, 131.1, 129.1, 128.0, 116.6, 115.9, 115.8, 115.8, 115.5,113.4, 71.9, 39.4, 35.3. For 8c, 1H-NMR (600 MHz, CDCl3)ae: 8.11-8.05 (m, 2H), 7.95-7.90 (m, 2H), 7.36-7.34 (m, 2H),7.20-7.15 (m, 2H), 7.12 (d, J = 2.2 Hz, 1H), 7.10-7.03 (m, 3H),6.83 (d, J = 8.4 Hz, 1H), 6.78 (d, J = 9.0 Hz, 1H), 6.01-5.92 (m,2H), 5.22 (s, 2H), 5.09 (s, 2H), 5.07-5.00 (m, 4H), 3.44 (d,J = 6.6 Hz, 2H), 3.35 (d, J = 6.7 Hz, 2H); 13C-NMR (150 MHz,CDCl3) ae: 193.8, 193.7, 155.0, 153.4, 137.6, 136.9, 133.9, 131.7,131.4, 131.3, 131.2, 131.0, 128.7, 128.3, 116.2, 116.0, 115.9,115.9, 115.8, 113.4, 111.2, 72.0, 71.5, 39.5, 34.5; LRMS (ESI)m/z: Calcd for C34H28F2O2 [M + Na]+ 561.18. Found 561.32.
  • 46
  • [ 35354-74-6 ]
  • [ 74-88-4 ]
  • [ 68592-18-7 ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate; In acetone; for 24h;Reflux; <strong>[35354-74-6]Honokiol</strong> (200 mg, 0.75 mmol) was solubilized in dry acetone (15 mL) and the solution was mixedwith K2CO3 (630.3 mg, 4.5 mmol) for 10 min. Then, MeI was added (0.19 mL, 3.2 mmol) and themixture was refluxed for 24 h. The mixture was filtered out and the permethylated compound 4 wasrecovered after column chromatography on silica gel (cyclohexanecyclohexane:acetone 80:20) with84% yield (185.6 mg). Spectroscopic data were in agreement with those previously reported [42].
  • 47
  • [ 35354-74-6 ]
  • [ 99-81-0 ]
  • 2-((3,5-diallyl-2-hydroxy-[1,1-biphenyl]-4-yl)oxy)-1-(4-nitrophenyl)ethan-1-one [ No CAS ]
  • C34H28N2O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
43%; 9% With caesium carbonate; In tetrahydrofuran; at 20℃; for 1h;Reflux; To a tetrahydrofuran solution (2 mL) of honokiol (50 mg,0.18 mmol) was added Cs2CO3 (183 mg, 0.56 mmol), followedby 2-bromo-4?-nitroacetophenone (46 mg, 0.18). After stirring1 h at room temperature, the reaction mixture was diluted inethyl acetate, washed with water and brine, dried over MgSO4,and concentrated under reduced pressure. The residue waspurified by flash column chromatography on silica gel (ethylacetate : n-hexane = 1 : 19 to 1 : 2) to afford 10a (35 mg, 43%,BORSM 54%), 10c (10 mg, 9%, BORSM 11%), and recoveredhonokiol (10 mg). 1H-NMR (600 MHz, CDCl3) delta: 8.37-8.34(m, 2H), 8.21-8.18 (m, 2H), 7.28 (dd, 2H, J = 5.1, 2.1 Hz), 7.05(dd, 1H, J = 8.2, 2.2 Hz), 7.01 (d, 1H, J = 2.1 Hz), 6.88 (dd, 2H,J = 14.2, 8.2 Hz), 6.00-5.94 (m, 2H), 5.30 (s, 2H), 5.10-5.02(m, 5H), 3.47 (d, 2H, J = 6.6 Hz), 3.34 (d, 2H, J = 6.7 Hz);13C-NMR (150 MHz, CDCl3) delta: 194.0, 155.1, 150.8, 150.8,139.1, 137.8, 136.3, 132.4, 131.4, 130.9, 130.3, 130.2, 129.7,129.1, 128.1, 127.5, 124.1, 116.3, 115.8, 115.7, 112.0, 71.6, 39.5,34.4; HRMS (EI) m/z: [M] Calcd for C26H23NO5 429.1576.Found 429.1574. For 10c, 1H-NMR (600 MHz, CDCl3) delta: 8.24(dd, J = 8.9, 1.7 Hz, 2H), 7.98 (dd, J = 9.0, 1.0 Hz, 2H), 7.80(dd, J = 9.0, 1.1 Hz, 2H), 7.42 (dd, J = 9.0, 2.1 Hz, 1H), 7.20(d, J = 2.0 Hz, 1H), 7.16-7.11 (m, 1H), 7.08-7.00 (m, 1H),6.86-6.76 (m, 1H), 5.99-5.88 (m, 1H), 5.09-4.98 (m, 2H), 4.82(d, J = 15.0 Hz, 1H), 4.57 (d, J = 10.8 Hz, 1H), 4.23-4.18 (m,1H), 3.90 (dd, J = 9.2, 6.9 Hz, 1H), 3.34 (dd, J = 19.1, 7.0 Hz,2H); 13C-NMR (150 MHz, CDCl3) delta: 209.8, 155.2, 153.5, 151.1,147.5, 147.1, 137.6, 136.9, 133.6, 131.9, 131.7, 131.2, 130.9,128.8, 128.6, 126.6, 126.5, 123.7, 123.3, 116, 113.2, 111.0, 75.0, 74.6, 49.3, 39.5; LRMS (ESI) m/z: Calcd for C34H28O2[M + H]+ 593.19. Found 593.35.
  • 48
  • [ 5292-43-3 ]
  • [ 35354-74-6 ]
  • tert-butyl 2-((3,5′-diallyl-2′-hydroxy-[1,1′-biphenyl]-4-yl)-oxy)acetate [ No CAS ]
  • tert-butyl 2-((3′,5-diallyl-4′-hydroxy-[1,1′-biphenyl]-2-yl)oxy)acetate [ No CAS ]
  • C30H38O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
37%; 13%; 26% With caesium carbonate; In tetrahydrofuran; at 20℃; for 1h;Reflux; To a tetrahydrofuran solution (2 mL) of honokiol (200 mg,0.75 mmol) was added Cs2CO3 (245 mg, 0.75 mmol), followedby tert-butyl bromoacetate (220 mg, 1.13). After stirring1 h at ambient temperature, the reaction mixture wasdiluted in ethyl acetate, washed with water and brine, driedover MgSO4, and concentrated under reduced pressure.The residue was purified by flash column chromatographyon silica gel (ethyl acetate : n-hexane = 1 : 19 to 1 : 2) to afford11a (107 mg, 37%, BORSM 48%), 11b (36 mg, 13%,BORSM 16%), 11c (97 mg, 26%, BORSM 33%), and recoveredhonokiol (43 mg). For 11a, 1H-NMR (600 MHz, CDCl3)ae: 7.24 (d, 2H, J = 2.3 Hz), 7.06-7.04 (m, 1H), 7.02 (d, 1H,J = 2.2 Hz), 6.90 (d, 1H, J = 8.2 Hz), 6.80 (d, 1H, J = 8.0 Hz),6.01 (dd, 2H, J = 44.3, 6.9 Hz), 5.14-5.04 (m, 5H), 4.58 (s,2H), 3.51 (d, 2H, J = 6.7 Hz), 3.35 (d, 2H, J = 6.7 Hz), 1.51 (s,9H); 13C-NMR (150 MHz, CDCl3) ae: 167.9, 155.4, 150.8, 137.7,136.3, 132.1, 130.8, 130.2, 130.1, 129.9, 128.8, 127.7, 127.6,116.0, 115.5, 115.5, 111.8, 82.4, 65.9, 39.4, 34.3, 28.1; HRMS(EI) m/z: [M] Calcd for C24H28O4 380.1988. Found 380.1987.For 11b, 1H-NMR (600 MHz, CDCl3) ae: 7.40 (dd, J = 8.2,2.2 Hz, 1H), 7.36 (d, J = 2.1 Hz, 1H), 7.14 (d, J = 2.2 Hz, 1H),7.06 (dd, J = 8.3, 2.2 Hz, 1H), 6.84 (d, J = 8.3 Hz, 1H), 6.79(d, J = 8.4 Hz, 1H), 6.10-6.03 (m, 1H), 6.00-5.93 (m, 1H),5.23-5.20 (m, 1H), 5.18-5.16 (m, 1H), 5.10-5.04 (m, 3H),5.01 (bs, 1H), 4.46 (s, 2H), 3.46 (d, J = 6.4 Hz, 2H), 3.37 (d,J = 6.7 Hz, 2H), 1.48 (s, 9H); 13C-NMR (150 MHz, CDCl3)ae: 168.5, 153.5, 153.3, 137.7, 136.7, 133.4, 131.6, 131.3, 130.8,130.8, 129.2, 127.8, 125.0, 116.4, 115.7, 115.5, 112.8, 82.3, 66.5,39.5, 35.3, 28.1; HRMS (EI) m/z: [M] Calcd for C24H28O4380.1988. Found 380.1986. For 11c, 1H-NMR (600 MHz,CDCl3) ae: 7.44 (dd, J = 8.4, 2.3 Hz, 1H), 7.40 (d, J = 2.2 Hz,1H), 7.13 (d, J = 2.3 Hz, 1H), 7.05 (dd, J = 8.3, 2.3 Hz, 1H),6.77 (dd, J = 10.7, 8.4 Hz, 2H), 6.11-6.04 (m, 1H), 6.00-5.94(m, 1H), 5.14-5.03 (m, 4H), 4.55 (s, 2H), 4.44 (s, 2H), 3.51 (d,J = 6.7 Hz, 2H), 3.36 (d, J = 6.7 Hz, 2H), 1.51 (s, 9H), 1.46 (s,9H); 13C-NMR (150 MHz, CDCl3) ae: 168.3, 168.3, 155.0, 153.4,137.8, 137.1, 133.4, 131.5, 131.4, 131.4, 130.8, 128.8, 128.5, 128,115.8, 115.6, 112.9, 111.1, 82.3, 82.2, 66.5, 66.4, 39.5, 34.6,28.2, 28.2; LRMS (ESI) m/z: Calcd for C30H38O6 [M + Na]+517.25. Found 517.37.
  • 49
  • [ 35354-74-6 ]
  • [ 5437-45-6 ]
  • C36H34O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With caesium carbonate; triethylamine; potassium iodide; In acetone; at 20℃; for 24h; <strong>[35354-74-6]Honokiol</strong> (0.5g, 1.88mmol)Was dissolved in acetone, and then Cs2CO3 (0.88 mmol),TEA (0.5 mL, 3.76 mmol),Benzyl-2-bromoacetate (1.88 mmol)And KI (3.76 mmol) were added and reacted at room temperature for 24 hours.After the reaction was completed, the mixture was concentrated under reduced pressure to remove the solvent, and the reaction mixture was washed with water and DCM. The organic layer was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure. The obtained residue was subjected to silica column chromatography (DCM: Ether: HEX = 6: 2: 22 v: v: v, Rf = 0.7).To give compound 4(White liquid, 100 mg, 9% yield).
  • 50
  • [ 35354-74-6 ]
  • [ 105-39-5 ]
  • [ 1333391-01-7 ]
YieldReaction ConditionsOperation in experiment
27% With caesium carbonate; potassium iodide; In acetone; at 20℃; for 24h; <strong>[35354-74-6]Honokiol</strong> (0.2g, 0.75mmol)Was dissolved in acetone, and then Cs2CO3 (0.15 mmol),Ethylchloroacetate (1.5mmol)And KI (0.015 mmol)Was added and reacted at room temperature for 24 hours.After the reaction was completed, the mixture was concentrated under reduced pressure to remove the solvent, and the reaction mixture was washed with water and DCM. The organic layer was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure. The obtained residue was purified by silica column chromatography (EA: HEX = 1: 3 v: v) to give compound 10 (yellow liquid, 90 mg, 27% yield).
  • 51
  • [ 96-30-0 ]
  • [ 35354-74-6 ]
  • C24H28N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With caesium carbonate; potassium iodide; In acetone; at 20℃; for 24h; Honokiol (0.2g, 0.75mmol)Was dissolved in acetone, and then Cs2CO3 (0.15 mmol),2-chloro-N-methylacetamide (1.5 mmol)And KI (0.015 mmol) were added and reacted at room temperature for 24 hours.After the reaction was completed, the mixture was concentrated under reduced pressure to remove the solvent, and the reaction mixture was washed with water and DCM. The organic layer was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure. The obtained residue was purified by silica column chromatography (EA: HEX = 2: 1 v: v) to give compound 11 (yellow liquid, 169 mg, 55% yield).
  • 52
  • [ 35354-74-6 ]
  • [ 79-07-2 ]
  • C22H24N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With caesium carbonate; potassium iodide; In acetone; at 20℃; for 24h; <strong>[35354-74-6]Honokiol</strong> (0.2g, 0.75mmol)Was dissolved in acetone, and then Cs2CO3 (0.15 mmol),2-chloroacetamide (1.5 mmol)And KI (0.015 mmol) were added and reacted at room temperature for 24 hours. After the reaction was completed, the mixture was concentrated under reduced pressure to remove the solvent, and the reaction mixture was washed with water and DCM. The organic layer was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure. The obtained residue was purified by silica column chromatography (EA: HEX = 4: 1 v: v) to give compound 12.(White liquid, 196 mg, 33% yield).
  • 53
  • [ 35354-74-6 ]
  • [ 590-17-0 ]
  • C22H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With caesium carbonate; potassium iodide; In acetone; at 20℃; for 24h; <strong>[35354-74-6]Honokiol</strong> (0.5g, 1.88mmol)Was dissolved in acetone, and then Cs2CO3 (2.8 mmol)And bromoacetonitrile (1.8 mmol)Was added and reacted at room temperature for 24 hours.After the reaction was completed, the mixture was concentrated under reduced pressure to remove the solvent, and the reaction mixture was washed with water and DCM. The organic layer was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure. The obtained residue was purified by silica column chromatography (DCM: Ether: HEX = 49: 2: 49 v: v: v) to give compound 13 (yellow liquid, 397 mg, 61% yield).
  • 54
  • [ 35354-74-6 ]
  • [ 74-88-4 ]
  • [ 68592-19-8 ]
YieldReaction ConditionsOperation in experiment
6.5% With caesium carbonate; In acetone; at 20℃; for 24h; <strong>[35354-74-6]Honokiol</strong> (0.5g, 1.88mmol)Was dissolved in acetone, and then Cs2CO3 (0.92 g, 2.8 mmol)And iodomethane (0.17 mL, 2.8 mol)Was added and reacted at room temperature for 24 hours.After the reaction was completed, the mixture was concentrated under reduced pressure to remove the solvent, and after work-up using water and dichloromethane (DCM), the organic layer obtained was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure. The obtained residue was purified by silica column chromatography (DCM: Ether: HEX = 49: 2: 49 v: v: v, Rf = 0.35).Purification gave compound 1(Yellow liquid, 34 mg, 6.5% yield).
  • 55
  • [ 35354-74-6 ]
  • [ 96-34-4 ]
  • C24H26O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With caesium carbonate; triethylamine; potassium iodide; In acetone; at 20℃; for 24h; <strong>[35354-74-6]Honokiol</strong> (0.5g, 1.88mmol)Was dissolved in acetone, and then Cs2CO3 (0.88 mmol),TEA (0.5 mL, 3.76 mmol),Methylchloroacetate (1.88 mmol)And KI (3.76 mmol) were added and reacted at room temperature for 24 hours. After the reaction was completed, the mixture was concentrated under reduced pressure to remove the solvent, and the reaction mixture was washed with water and DCM. The organic layer was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure.The obtained residue was subjected to silica column chromatography.(DCM: Ether: HEX = 6: 2: 22 v: v: v, Rf = 0.83)To give compound 2(White liquid, 210 mg, 27% yield).
  • 56
  • [ 35354-74-6 ]
  • [ 96-34-4 ]
  • C21H22O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With caesium carbonate; triethylamine; potassium iodide; In acetone; at 20℃; for 24h; <strong>[35354-74-6]Honokiol</strong> (0.5g, 1.88mmol)Was dissolved in acetone, and then Cs2CO3 (0.88 mmol),TEA (0.5 mL, 3.76 mmol),Methylchloroacetate (1.88 mmol)And KI (0.38 g, 3.76 mmol)Was added and reacted at room temperature for 24 hours.After the reaction was completed, the mixture was concentrated under reduced pressure to remove the solvent, and the reaction mixture was washed with water and DCM. The organic layer was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure. The obtained residue was subjected to silica column chromatography (DCM: Ether: HEX = 6: 2: 22 v: v: v, Rf = 0.67).Purification was carried out to give compound 3 (white liquid, 74 mg, 12% yield).
  • 57
  • [ 35354-74-6 ]
  • [ 96-34-4 ]
  • C21H22O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With caesium carbonate; triethylamine; potassium iodide; In acetone; at 20℃; for 24h; <strong>[35354-74-6]Honokiol</strong> (0.5g, 1.88mmol)Was dissolved in acetone, and then Cs2CO3 (0.88 mmol),TEA (3.76 mmol),Methylchloroacetate (1.88 mmol) And KI (3.76 mmol) were added and reacted at room temperature for 24 hours. After the reaction was completed, the mixture was concentrated under reduced pressure to remove the solvent, and the reaction mixture was washed with water and DCM. The organic layer was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure. The obtained residue was subjected to silica column chromatography (DCM: Ether: HEX = 6: 2: 22 v: v: v, Rf = 0.52).Purification was carried out to give compound 8 (white liquid, 74 mg, 12% yield).
  • 58
  • [ 35354-74-6 ]
  • [ 145193-16-4 ]
  • allyl 2-((5,5'-diallyl-4'-hydroxy-[1,1'-biphenyl]-2-yl)oxy)-2-phenylacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% At room temperature, weigh allyl phenyldiazoacetate 1b (0.5 mmol),<strong>[35354-74-6]Honokiol</strong> 5b (0.8 mmol) in a 25 mL Schlenk reaction tube, in an air atmosphere,Add 5 mL of 1,2-dichloroethane, and stir at room temperature for 2 minutes.98% trifluoromethanesulfonic acid 0.1mmol (10muL), continue the reaction for 30min,TLC detects that the raw materials have reacted completely, and stops the reaction; concentrated under reduced pressure to remove volatile components,Silica gel column chromatography(Eluent: petroleum ether (60-90 C) / ethyl acetate, v / v = 10: 1),Obtained the colorless transparent viscous target product7b (112mg, yield 51%). The target product was confirmed by nuclear magnetic resonance spectrum and high resolution mass spectrometry.
  • 59
  • [ 35354-74-6 ]
  • [ 106-95-6 ]
  • 3',5-diallyl-2,4'-bis(allyloxy)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate; In acetone; at 56℃; for 12h; General procedure: A solution of the proper bisphenol neolignan (2, 12a-c; 0.5 mmol) in dry acetone (5 mL) wasmixed with K2CO3 (275.7 mg; 2.0 mmol) for 10 min, then, allyl bromide (130 L; 1.5 mmol) wasadded and the mixture was refluxed overnight. The mixture was filtered and where necessary itwas chromatographed.30,5-Diallyl-2,40-bis(allyloxy)-1,10-biphenyl (8). The expected compound was recovered with 97%yield (184.9 mg) after filtration of the mixture. Rf 0.79 (cyclohexane:acetone 70:30). Spectroscopic datawere in agreement with those reported in the literature [20].
  • 60
  • [ 50-00-0 ]
  • [ 35354-74-6 ]
  • [ 111-42-2 ]
  • C28H40N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% Add 1 ml of hydrochloric acid with a concentration of 12 mol / L to 70 ml of methanol. Prepare a methanolic acid solution for later use. Weigh 13g of diethanolamine into a three-necked flask, Slowly add 10 ml of 37% formaldehyde solution, magnetically stir, control the dropping acceleration to 1 ml / min, and control the temperature at 30-35 C. In ice water bath conditions, Add 40ml of the prepared methanolic acid solution to the three-necked flask. Control the drop acceleration to 4ml / min, the temperature is 2-5 C, and continue magnetic stirring for 1h. Weigh 10 g of honokiol (98% content) and dissolve in the remaining 30 ml of methanolic acid solution. The three-necked flask was placed in an oil bath to control the temperature to 85 C., a methanol solution of honokiol was added, and the mixture was refluxed under reflux for 6.5 hours. Remove excess methanol using a rotary evaporator, Purification was performed on a 200-mesh silica gel column with ethyl acetate / acetone as eluent. The volume ratio of ethyl acetate to acetone was 4: 1, and the obtained eluates were combined and concentrated. It was then lyophilized to obtain a honokiol derivative. Based on honokiol in the reaction material, The yield was 35%.
  • 61
  • [ 50-00-0 ]
  • [ 107-97-1 ]
  • [ 35354-74-6 ]
  • C26H32N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% Add 1 ml of hydrochloric acid with a concentration of 12 mol / L to 70 ml of methanol. Prepare a methanolic acid solution for later use.Weigh 7.6g of N-methyl-glycine powder into a three-necked flask,Slowly add 10 ml of a 37% by mass formaldehyde solution and stir magnetically. The controlled drop acceleration is 1ml / min, and the controlled temperature is 30-35 C. In an ice water bath, add 40 ml of the prepared methanolic acid solution to a three-necked flask.Control the drop acceleration to 4ml / min, the temperature is 2-5 C, and continue magnetic stirring for 1h. Weigh 13.3 g of honokiol (98% content) and dissolve in the remaining 30 ml of methanolic acid solution. Place the three-necked flask in an oil bath to control the temperature to 75 C. A honokiol methanolic acid solution was added, and the mixture was refluxed for 10 hours. Remove excess methanol using a rotary evaporator and purify using a 200 mesh silica gel column. The eluent was ethyl acetate / acetone, and the volume ratio of ethyl acetate to acetone was 4: 1. The obtained eluates were combined and concentrated, and then lyophilized to obtain a honokiol derivative. The yield was 35% based on honokiol in the reaction raw material.
  • 62
  • [ 35354-74-6 ]
  • [ 93961-29-6 ]
  • methyl 2-(4-chlorophenyl)-2-((3',5-diallyl-4'-hydroxy-[1,1'-biphenyl]-2-yl)oxy)acetate [ No CAS ]
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