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[ CAS No. 22139-77-1 ] {[proInfo.proName]}

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Chemical Structure| 22139-77-1
Chemical Structure| 22139-77-1
Structure of 22139-77-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 22139-77-1 ]

CAS No. :22139-77-1 MDL No. :MFCD00210544
Formula : C14H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :YCVPRTHEGLPYPB-VOTSOKGWSA-N
M.W : 212.24 Pubchem ID :5280457
Synonyms :
trans-3,5-Dihydroxystilbene

Calculated chemistry of [ 22139-77-1 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 65.86
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 3.48
Log Po/w (WLOGP) : 3.05
Log Po/w (MLOGP) : 2.87
Log Po/w (SILICOS-IT) : 3.07
Consensus Log Po/w : 2.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.77
Solubility : 0.0359 mg/ml ; 0.000169 mol/l
Class : Soluble
Log S (Ali) : -4.01
Solubility : 0.0206 mg/ml ; 0.0000973 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.86
Solubility : 0.0292 mg/ml ; 0.000138 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.98

Safety of [ 22139-77-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22139-77-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 22139-77-1 ]

[ 22139-77-1 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 35302-70-6 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine hydrochloride at 180℃;
  • 2
  • [ 22139-77-1 ]
  • [ 108-24-7 ]
  • [ 71144-79-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine
  • 3
  • [ 22139-77-1 ]
  • [ 77-78-1 ]
  • [ 21956-56-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; ethanol
  • 4
  • [ 109-65-9 ]
  • [ 22139-77-1 ]
  • [ 143207-70-9 ]
YieldReaction ConditionsOperation in experiment
35% With potassium carbonate In acetone Heating;
  • 5
  • [ 74-96-4 ]
  • [ 22139-77-1 ]
  • [ 143207-67-4 ]
YieldReaction ConditionsOperation in experiment
29% With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere;
20% With potassium carbonate In acetone Heating;
  • 6
  • [ 629-04-9 ]
  • [ 22139-77-1 ]
  • [ 143207-73-2 ]
YieldReaction ConditionsOperation in experiment
41% With potassium carbonate In acetone Heating;
  • 7
  • [ 541-47-9 ]
  • [ 22139-77-1 ]
  • [ 129657-74-5 ]
  • [ 129657-75-6 ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate at 25℃; for 40h; Yield given. Yields of byproduct given;
  • 8
  • [ 110-53-2 ]
  • [ 22139-77-1 ]
  • [ 143207-71-0 ]
YieldReaction ConditionsOperation in experiment
26% With potassium carbonate In acetone Heating;
  • 9
  • [ 111-25-1 ]
  • [ 22139-77-1 ]
  • [ 143207-72-1 ]
YieldReaction ConditionsOperation in experiment
36% With potassium carbonate In acetone Heating;
  • 10
  • [ 111-83-1 ]
  • [ 22139-77-1 ]
  • [ 143207-74-3 ]
YieldReaction ConditionsOperation in experiment
40% With potassium carbonate In acetone Heating;
  • 11
  • [ 112-29-8 ]
  • [ 22139-77-1 ]
  • [ 143207-75-4 ]
YieldReaction ConditionsOperation in experiment
53% With potassium carbonate In acetone Heating;
  • 12
  • [ 22139-77-1 ]
  • [ 14531-52-3 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen In ethanol for 1h;
With hydrogen Yield given;
  • 13
  • [ 21956-56-9 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
85% With pyridine hydrochloride at 190℃; for 4h;
83% With boron tribromide In dichloromethane at -20 - 20℃; Inert atmosphere;
83% With boron tribromide In dichloromethane at -20 - 20℃; Inert atmosphere; 1 E-1-(2-(3,5-dimethoxyphenyl)vinyl)benzene, 0.2 mmol,48mg, dissolved in 6mL anhydrous dichloromethane under nitrogen protection,Stir at -20 ° C and slowly add 0.34 g, 1.34 mmol of boron tribromide.30% was dissolved in anhydrous dichloromethane. The mixture is stirred under nitrogen,And slowly rise to room temperature, the reaction is 4 ~ 5h, after the reaction is completed, add 10ml of water,The mixture was extracted three times with dichloromethane, washed with brine and dried over anhydrous sodium sulfate.The crude product was concentrated under reduced pressure and purified by column chromatography (hexane/hexane = 6/4).Get silver pine,White solid 35 mg, yield 83%.
83% With boron tribromide In dichloromethane at -20 - 20℃; Inert atmosphere; 2 (2) Add 0.2mmol of (E-1,2-bis(4-methoxyphenyl)vinyl)benzene to 6mL of anhydrous dichloromethane under the protection of nitrogen to dissolve, stir and slowly add dropwise at -20 1.34mmol of boron tribromide (0.34 g, 30% dissolved in anhydrous dichloromethane), the mixture is stirred under nitrogen protection, and slowly rises to room temperature to react for 4~5h. After the reaction is completed, add 10ml of water and dichloromethane Extracted 3 times, washed with brine, and dried over anhydrous sodium sulfate; concentrated under reduced pressure and purified by column chromatography (n-hexane/acetone=6/4) to obtain silver pintin, white solid 35mg, reaction yield 83%.
80% With boron tribromide-dimethyl sulfide complex In 1,2-dichloro-ethane
32% With boron tribromide In dichloromethane at 5℃; Reflux;
29% With boron tribromide In dichloromethane at -10 - 20℃; for 24h; Inert atmosphere; 2. General procedure for demethylation of stilbene 4 General procedure: In 6 mL of anhydrous methylene chloride, 200 mg of methoxy-stilbene 4 (0.74 mmol) was dissolved and cooled to -10 °C under argon. BBr3 (0.6 mL, 6.3 mmol, 17% in dichloromethane) in anhydrous methylene chloride (5 mL) was added slowly, and the mixture was allowed to reach to room temperature for 3-24 h. Water was added to destroy the excess BBr3, and the mixture was extracted twice with ethyl acetate. The organic extracts were washed with water and brine and dried, and the solvent evaporated. The crude product was purified by column chromatography on silica gel (20% EtOAc in hexane) yielding resveratrol and derivatives 1.
13 mg With pyridine hydrochloride at 190℃; for 3h;
With pyridine hydrochloride at 190℃; for 4h;
With pyridine hydrochloride at 190℃; for 4h;
With pyridine hydrochloride at 190℃;
With hydrogenchloride; pyridine hydrochloride 1.e 3rd Step 3rd Step For demethylation, a homogeneous mixture of 54.0 g (0.22 mol) of 3,5-dimethoxystilbene and 40.0 g (0.35 mol) of pyridine hydrochloride is heated at about 165° C. for 3 hours. The cooled, oily reaction mass is then introduced into 1.2 liters of 2N hydrochloric acid and the crude product is isolated by extraction with diethyl ether. Recrystallisation from toluene yields 3,5-dlihydroxystilbene in the form of a pale-yellow powder. Yield: 26.0 g (0.12 mol; 41.0% of theory)
With pyridine hydrochloride at 180 - 200℃; Inert atmosphere;
69 mg With boron tribromide In dichloromethane at 0 - 20℃; Schlenk technique; Inert atmosphere;
62 mg With boron tribromide In dichloromethane at -20℃; Inert atmosphere; diastereoselective reaction;

Reference: [1]Location in patent: body text Xia, Likai; Lee, Yong Rok [Synlett, 2008, # 11, p. 1643 - 1646]
[2]Yang., Jinfei; Wang, Chengniu; Sun, Yufeng; Man, Xuyan; Li, Jinxia; Sun, Fei [Chemical Communications, 2019, vol. 55, # 13, p. 1903 - 1906]
[3]Current Patent Assignee: NANTONG UNIVERSITY - CN109758438, 2019, A Location in patent: Paragraph 0032-0034; 0039-0041
[4]Current Patent Assignee: NANTONG UNIVERSITY - CN111763139, 2020, A Location in patent: Paragraph 0020; 0021
[5]Alonso, Emma; Ramon, Diego J.; Yus, Miguel [Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 417 - 421]
[6]Location in patent: experimental part Smidrkal, Jan; Harmatha, Juraj; BudiSinsky, Milo; Vokae, Karel; ZIDEKc, Zdenik; Kmoniekova, Eva; Merkl, Roman; Filip, Vladimir [Collection of Czechoslovak Chemical Communications, 2010, vol. 75, # 2, p. 175 - 186]
[7]Uzura, Saori; Sekine-Suzuki, Emiko; Nakanishi, Ikuo; Sonoda, Motohiro; Tanimori, Shinji [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 3886 - 3891]
[8]Suga, Takayuki; Ohta, Shinji; Munesada, Kiyotaka; Ide, Nagatoshi; Kurokawa, Masako; et al. [Phytochemistry, 1993, vol. 33, # 6, p. 1395 - 1402]
[9]Wang, Mingfu; Jin, Yi; Ho, Chi-Tang [Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 10, p. 3974 - 3977]
[10]Lu; Cai; Fang; Zhou; Liu; Wu, Longmin M. [Pharmazie, 2002, vol. 57, # 7, p. 474 - 478]
[11]Park, Eun-Jung; Min, Hye-Young; Ahn, Yong-Hyun; Bae, Cheol-Man; Pyee, Jae-Ho; Lee, Sang Kook [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 23, p. 5895 - 5898]
[12]Current Patent Assignee: BASF SE - US6814960, 2004, B1
[13]Shang, Ya-Jing; Qian, Yi-Ping; Liu, Xiao-Da; Dai, Fang; Shang, Xian-Ling; Jia, Wen-Qiang; Liu, Qiang; Fang, Jian-Guo; Zhou, Bo [Journal of Organic Chemistry, 2009, vol. 74, # 14, p. 5025 - 5031] Qian, Yi-Ping; Cai, Yu-Jun; Fan, Gui-Juan; Wei, Qing-Yi; Jie, Yang; Zheng, Li-Fang; Li, Xiu-Zhuang; Fang, Jian-Guo; Bo, Zhou [Journal of Medicinal Chemistry, 2009, vol. 52, # 7, p. 1963 - 1974]
[14]Girase, Tejpalsingh Ramsingh; Kapdi, Anant R. [Chemistry - An Asian Journal, 2019, vol. 14, # 15, p. 2611 - 2619]
[15]Baumann, Andreas N.; Dechent, Jonas; Didier, Dorian; Jagau, Thomas C.; Müller, Nicolas; Music, Arif [Chemistry - A European Journal, 2020]
  • 14
  • [ 21956-56-9 ]
  • [ 22139-77-1 ]
  • [ 35302-70-6 ]
YieldReaction ConditionsOperation in experiment
1: 43% 2: 51% With boron tribromide In dichloromethane at 0 - 20℃;
  • 15
  • [ 133156-35-1 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogen In dichloromethane at 20℃; for 5h; 11 A solution of 21.1 g of 3,5_-dibenzyloxystilb was dissolved in 120 mL of CH2C12, and then 10.38 g of a catalyst having a loading of 5% Pd was charged at a pressure of 5 to 5 MPa, and the reaction was carried out at room temperature for 5 hours. After the completion of the reaction, The filtrate was recovered by filtration to recover the reaction solvent to obtain the crude product. The crude product was recrystallized from ethanol to give 9.5 g of pinosylvin in a yield of 90%.
70% With palladium 10% on activated carbon; ammonium formate In methanol; 1,2-dichloro-ethane at 40℃; for 0.75h; 7 Embodiment 7 Weighing 0 . 20 g of formula II - 6 shown (E)-1-phenyl-2-(3,5-dibenzyloxyphenyl)ethylene and 0 . 18 g ammonium formate in 6 ml mixed solvent (1, 2 - dichloroethane/methanol=1/1) by heating to 40 °C, stirring 15 minutes, the raw material is dissolved. The insulation by adding 0 . 026 g 10% palladium-carbon catalyst, thermal insulation stirring TLC monitoring until the reaction is complete, about 30 minutes. Filtering to remove the palladium-carbon, reducing pressure of the mother liquor solvent, residue by column chromatography separation to obtain the target product I - 6 indicated by the 5-[(1E)-2-phenylvinyl]-1,3-benzenediol 0.076g, yield 70%.
58% With aluminium trichloride; <i>N</i>,<i>N</i>-dimethyl-aniline In dichloromethane at 0℃;
  • 16
  • [ 22139-77-1 ]
  • [ 106-94-5 ]
  • [ 143207-68-5 ]
YieldReaction ConditionsOperation in experiment
34% With potassium carbonate In acetone Heating;
12% With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere;
  • 17
  • [ 106325-78-4 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
99% With diphenyldisulfane In tetrahydrofuran for 0.5h; Heating;
  • 18
  • [ 106325-78-4 ]
  • [ 22139-77-1 ]
  • (E)-4-iodo-3,5-dihydroxy-stilbene [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 64% 2: 13% With iodine In benzene for 5h; Ambient temperature;
  • 19
  • [ 107192-05-2 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogen fluoride In acetonitrile for 4h; Ambient temperature;
  • 20
  • [ 22139-77-1 ]
  • [ 106-95-6 ]
  • [ 143207-69-6 ]
YieldReaction ConditionsOperation in experiment
38% With potassium carbonate In acetone Heating;
28% With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere;
  • 21
  • [ 115-18-4 ]
  • [ 22139-77-1 ]
  • chiricanine A [ No CAS ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate In 1,4-dioxane
  • 22
  • [ 115-18-4 ]
  • [ 22139-77-1 ]
  • trans-3,5-dimethoxy-2-prenylstilbene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate In 1,4-dioxane
  • 23
  • [ 115-18-4 ]
  • [ 22139-77-1 ]
  • [ 64095-62-1 ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate In 1,4-dioxane
  • 24
  • [ 115-18-4 ]
  • [ 22139-77-1 ]
  • [ 64095-61-0 ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate In 1,4-dioxane
  • 25
  • [ 5252-43-7 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
(i) KOH, MeOH, (ii) aq. NaOH; Multistep reaction;
  • 26
  • (E)-2-hydroxy-4-methoxy-6-[styryl]benzoic acid methyl ester [ No CAS ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide In acetic acid
YieldReaction ConditionsOperation in experiment
With quinoline; copper at 240 - 260℃; Kochen des Reaktionsprodukts mit wss. NaOH;
  • 28
  • [ 22139-77-1 ]
  • [ 360784-17-4 ]
  • C52H73NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% In toluene; butan-1-ol for 4h; Heating;
  • 30
  • [ 22139-77-1 ]
  • [ 57-50-1 ]
  • 3-O-α-D-glucopyranosyl-(E)-pinosylvin [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% With phosphate buffer; Streptococcus mutans at 37℃; for 48h;
  • 31
  • [ 22139-77-1 ]
  • [ 760-67-8 ]
  • 2-Ethyl-hexanoic acid 3-hydroxy-5-((E)-styryl)-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With pyridine In dichloromethane at 20℃;
  • 32
  • [ 22139-77-1 ]
  • [ 112-67-4 ]
  • Hexadecanoic acid 3-hydroxy-5-((E)-styryl)-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With pyridine In dichloromethane at 20℃;
  • 33
  • [ 22139-77-1 ]
  • [ 112-67-4 ]
  • Hexadecanoic acid 3-hexadecanoyloxy-5-((E)-styryl)-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With pyridine In dichloromethane at 20℃;
  • 34
  • [ 22139-77-1 ]
  • [ 133156-35-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 50 percent / K2CO3 / acetone 2: 98 percent / K2CO3 / acetone
  • 35
  • [ 7311-34-4 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaOMe / dimethylformamide / 0 °C 1.2: dimethylformamide / 20 °C 2.1: pyridine hydrochloride / 190 °C
Multi-step reaction with 2 steps 1: 35.1 g 2: 13 mg / pyridine hydrochloride / 3 h / 190 °C
Multi-step reaction with 2 steps 1: 1.) potassium tert-butoxide, 2.) diphenyl disulfide / 1.) THF, 30 min, 2.) THF, reflux, 4 h 2: 51 percent / BBr3 / CH2Cl2 / 0 - 20 °C
  • 36
  • [ 1080-32-6 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaOMe / dimethylformamide / 0 °C 1.2: dimethylformamide / 20 °C 2.1: pyridine hydrochloride / 190 °C
Multi-step reaction with 2 steps 1: 35.1 g 2: 13 mg / pyridine hydrochloride / 3 h / 190 °C
  • 37
  • [ 100-39-0 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 130 °C 2.1: NaOMe / dimethylformamide / 0 °C 2.2: dimethylformamide / 20 °C 3.1: pyridine hydrochloride / 190 °C
  • 38
  • [ 100-39-0 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethyl phosphate / 130 °C 1.2: NaOMe / dimethylformamide / 20 - 100 °C 2.1: pyridine hydrochloride / 4 h / 190 °C
  • 39
  • [ 100-51-6 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: gaseous HBr / benzene / 1 h / 78 °C 2.1: triethyl phosphate / 130 °C 2.2: NaOMe / dimethylformamide / 20 - 100 °C 3.1: pyridine hydrochloride / 4 h / 190 °C
  • 40
  • [ 705-76-0 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Et3N / tetrahydrofuran / 1 h / 0 - 20 °C 2: 37 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 3: 75 percent / phosphoric acid / toluene / 2 h / Heating 4: 80 percent / BBr3*Me2S / 1,2-dichloro-ethane
  • 41
  • [ 185249-83-6 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 37 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 2: 75 percent / phosphoric acid / toluene / 2 h / Heating 3: 80 percent / BBr3*Me2S / 1,2-dichloro-ethane
  • 42
  • [ 185249-85-8 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / phosphoric acid / toluene / 2 h / Heating 2: 80 percent / BBr3*Me2S / 1,2-dichloro-ethane
  • 43
  • [ 1449-46-3 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) potassium tert-butoxide, 2.) diphenyl disulfide / 1.) THF, 30 min, 2.) THF, reflux, 4 h 2: 51 percent / BBr3 / CH2Cl2 / 0 - 20 °C
  • 44
  • [ 2150-44-9 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 94 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 95 percent / lithium aluminium hydride / diethyl ether / 1.) 30 min 2.) reflux, 1 h 3: 86 percent / Ph3P / CCl4 / 2 h / 75 - 80 °C 4: 83 percent / xylene / 10 h / Heating 5: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 6: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature
  • 45
  • [ 100-52-7 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 2: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature
  • 46
  • [ 103929-83-5 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 95 percent / lithium aluminium hydride / diethyl ether / 1.) 30 min 2.) reflux, 1 h 2: 86 percent / Ph3P / CCl4 / 2 h / 75 - 80 °C 3: 83 percent / xylene / 10 h / Heating 4: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 5: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature
  • 47
  • [ 103929-84-6 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 86 percent / Ph3P / CCl4 / 2 h / 75 - 80 °C 2: 83 percent / xylene / 10 h / Heating 3: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 4: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature
  • 48
  • [ 103929-85-7 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 83 percent / xylene / 10 h / Heating 2: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 3: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature
  • 49
  • [ 103929-86-8 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 2: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature
  • 50
  • [ 22139-77-1 ]
  • [ 78916-45-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / 10percent Pd-C 2: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min
  • 51
  • [ 22139-77-1 ]
  • [ 133462-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: H2 / 10percent Pd-C 2: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min 3: 5 mg / m-CPBA / CHCl3 / 2 h / Ambient temperature
  • 52
  • [ 22139-77-1 ]
  • [ 70610-15-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / 10percent Pd-C 2: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min
  • 53
  • [ 22139-77-1 ]
  • [ 133462-42-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / 10percent Pd-C 2: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min
  • 54
  • [ 22139-77-1 ]
  • [ 69026-25-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C 3: 96 percent / NaIO4, OsO4 / dioxane; H2O / 15 h / 25 °C 4: 96 percent / potassium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C 5: NaH / diethyl ether / 1 h / 15 °C 6: 1) Et3N, 2) 2 N KOH / 1) MeOH, ether, 18 h, 25 deg C, 2) 0 deg C, 15 min, MeOH
  • 55
  • [ 22139-77-1 ]
  • [ 69025-77-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C 3: 96 percent / NaIO4, OsO4 / dioxane; H2O / 15 h / 25 °C 4: 96 percent / potassium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C
  • 56
  • [ 22139-77-1 ]
  • [ 69025-76-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C 3: 96 percent / NaIO4, OsO4 / dioxane; H2O / 15 h / 25 °C
  • 57
  • [ 22139-77-1 ]
  • [ 69025-78-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C 3: 96 percent / NaIO4, OsO4 / dioxane; H2O / 15 h / 25 °C 4: 96 percent / potassium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C 5: NaH / diethyl ether / 1 h / 15 °C
  • 58
  • [ 22139-77-1 ]
  • [ 129657-76-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C
  • 59
  • [ 22139-77-1 ]
  • [ 78916-50-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol; aqueous NaOH 2: diethyl ether; platinum / Hydrogenation
  • 60
  • [ 22139-77-1 ]
  • [ 133462-94-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol; aqueous NaOH 2: diethyl ether; platinum / Hydrogenation 3: bromine
  • 61
  • [ 24131-32-6 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 160 - 170 °C 2: H2 / Pd-C / ethanol 3: (i) KOtBu, DMF, (ii) /BRN= 471223/, toluene
  • 62
  • [ 33617-49-1 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / Pd-C / ethanol 2: (i) KOtBu, DMF, (ii) /BRN= 471223/, toluene
  • 63
  • [ 5949-05-3 ]
  • [ 22139-77-1 ]
  • (+)-machaeriol A [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With ethylenediamine diacetic acid; triethylamine In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Reflux;
  • 64
  • [ 2385-77-5 ]
  • [ 22139-77-1 ]
  • [ 1070876-43-5 ]
YieldReaction ConditionsOperation in experiment
76% With ethylenediamine diacetic acid; triethylamine In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Reflux;
  • 65
  • [ 22139-77-1 ]
  • [ 5392-40-5 ]
  • [ 1186228-55-6 ]
  • C24H26O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 23% 2: 40% With ethylenediamine diacetic acid In para-xylene for 10h; Inert atmosphere; Reflux;
  • 66
  • [ 14371-10-9 ]
  • [ 22139-77-1 ]
  • [ 1186228-57-8 ]
YieldReaction ConditionsOperation in experiment
79% With ethylenediamine diacetic acid In benzene for 12h; Reflux; Inert atmosphere;
  • 67
  • [ 502-67-0 ]
  • [ 22139-77-1 ]
  • [ 1186228-58-9 ]
YieldReaction ConditionsOperation in experiment
58% With ethylenediamine diacetic acid In benzene for 12h; Reflux; Inert atmosphere;
  • 68
  • [ 107-86-8 ]
  • [ 22139-77-1 ]
  • [ 1186228-54-5 ]
YieldReaction ConditionsOperation in experiment
78% With ethylenediamine diacetic acid In para-xylene for 8h; Reflux; Inert atmosphere;
  • 69
  • [ 1192-88-7 ]
  • [ 22139-77-1 ]
  • [ 1186228-59-0 ]
YieldReaction ConditionsOperation in experiment
67% With ethylenediamine diacetic acid In para-xylene for 12h; Reflux; Inert atmosphere;
  • 70
  • [ 22139-77-1 ]
  • [ 18031-40-8 ]
  • [ 1186228-60-3 ]
YieldReaction ConditionsOperation in experiment
79% With ethylenediamine diacetic acid In para-xylene for 8h; Reflux; Inert atmosphere;
  • 71
  • [ 22139-77-1 ]
  • [ 123-73-9 ]
  • [ 1186228-56-7 ]
YieldReaction ConditionsOperation in experiment
43% With ethylenediamine diacetic acid In benzene for 12h; Reflux; Inert atmosphere;
  • 72
  • [ 22139-77-1 ]
  • [ 5392-40-5 ]
  • [ 1186228-55-6 ]
YieldReaction ConditionsOperation in experiment
60% With ethylenediamine diacetic acid In benzene for 10h; Reflux; Inert atmosphere;
  • 73
  • [ 22139-77-1 ]
  • [ 5392-40-5 ]
  • [ 1186228-55-6 ]
  • C24H26O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 40% 2: 23% With ethylenediamine diacetic acid In para-xylene at 138℃; for 10h; Inert atmosphere;
  • 74
  • [ 107030-46-6 ]
  • [ 22139-77-1 ]
  • [ 106325-78-4 ]
YieldReaction ConditionsOperation in experiment
1: 9 mg 2: 15 mg With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.333333h;
  • 75
  • [ 22139-77-1 ]
  • [ 1114548-05-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: pyridine; trichlorophosphate / 0 - 100 °C / Inert atmosphere 4.1: hydrogenchloride; water / methanol / 10 h / 20 °C / Inert atmosphere
  • 76
  • [ 22139-77-1 ]
  • [ 1269415-89-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere
  • 77
  • [ 22139-77-1 ]
  • [ 1269415-91-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere
  • 78
  • [ 22139-77-1 ]
  • [ 1269415-92-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: pyridine; trichlorophosphate / 0 - 100 °C / Inert atmosphere
  • 79
  • [ 22139-77-1 ]
  • chiricanine A [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride; water / methanol / 10 h / 20 °C / Inert atmosphere
  • 80
  • [ 22139-77-1 ]
  • [ 107-30-2 ]
  • [ 1269415-88-4 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
  • 81
  • [ 22139-77-1 ]
  • [ 590-86-3 ]
  • [ 1114548-05-8 ]
YieldReaction ConditionsOperation in experiment
54% With ethylenediamine diacetic acid In benzene for 10h; Inert atmosphere; Reflux;
  • 82
  • [ 71144-79-1 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium hydroxide In methanol; hexane; water; ethyl acetate 12 Example 12 Example 12 (E)-3,5-Dihydroxystilbene, [(E)-5-styrylbenzene-1,3-diol] (12). A solution of potassium hydroxide in methanol was added to (E)-5-styryl-1,3-phenylene diacetate suspended in methanol. The solution was heated under a nitrogen atmosphere to 70° C. for 100 minutes. Upon cooling to room temperature, the solution was acidified to pH 3 by addition of 1 M HCl. Water was added, and the volume reduced by rotary evaporation and stopped at the first appearance of a precipitate. Ethyl acetate was added and the organic layer was separated and washed four times with water until the aqueous washings were neutral. The organic material was then dried, filtered and rotary evaporated to give an orange oil. Purification by gradient elution column chromatography (2:1 hexane/EtOAc to 1:1 hexane/EtOAc) gave (E)-5-styrylbenzene-1,3-diol as a white solid. Rf 0.17 (hexane/EtOAc 4:1), 0.62 (hexane/EtOAc 1:1); mp 157.0-157.5° C., 1H NMR (CD3OD): δ 6.18 (pseudo t, 1H, J=2.2 Hz, H-4), 6.46 (d, 2H, J=2.2 Hz, H-2, H-6), 6.95 (d, 1H, J=16.3 Hz, Htrans) 7.01 (d, 1H, J=16.3 Hz, Htrans), 7.15-7.21 (m, 1H, H-4'), 7.26-7.32 (m, 2H, H-3', H-5'), 7.44-7.48 (m, 2H, 2', 6'); 13C JMOD NMR (CD3OD): δ 100.91 (4), 103.92 (2,6), 125.13 (2', 6'), 126.19, 127.27, 127.48 (2*Ctrans, 4'), 127.31 (3', 5'), 136.32 (1'), 138.52 (1), 157.28 (3, 5); LRESI positive ion mass spectrum; m/z 213 (MH+, 100%), 214 (18%); HRESI positive ion mass spectrum; C14H12O2Na+; calc. 235.0735, measured 235.0729.
With sodium hydroxide In dichloromethane at 20℃; for 2.5h; Inert atmosphere; Cooling with ice; Preparation of (E)-5-[2-(3, 5-Dibromo-4-hydroxy-phenyl)-vinyl]-phenol (Compound 4z) General procedure: Acetic acid 4-[2-(3,5-dibromo-4-methoxy-phenyl)-vinyl]-phenyl ester (33 mg, 0.077 mmol) was diluted in dichloromethane (1.0 mL) and added 1.0 M dichloromethane solution of boron tribromide (0.23 mL, 0.23 mmol) under nitrogen and ice cooling. The mixture was stirred at room temperature for 2.5 h. The reaction mixture was added to cooled water under ice cooling, and extracted with ethyl acetate. The combined organic layer was washed with water and brine, then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (20% ethyl acetate in n-hexane) to give the desire compound 4z as a white powder (26 mg, 91%).
  • 83
  • [ 100-42-5 ]
  • [ 192182-54-0 ]
  • [ 22139-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro bis(acetonitrile) palladium(II); sodium carbonate; oxygen / N,N-dimethyl-formamide / 18 h / 50 °C 2: boron tribromide / dichloromethane / 24 h / -10 - 20 °C / Inert atmosphere
  • 84
  • [ 22139-77-1 ]
  • [ 501-36-0 ]
YieldReaction ConditionsOperation in experiment
83% With L234Q/I238V/G239A In dimethyl sulfoxide at 20℃; for 20h; Enzymatic reaction; regioselective reaction;
With unspecific peroxygenase from Marasmius rotula DSM-25031; dihydrogen peroxide; ascorbic acid In aq. phosphate buffer; acetone at 30℃; for 0.5h; Enzymatic reaction; regioselective reaction;
Same Skeleton Products
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