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[ CAS No. 18869-29-9 ] {[proInfo.proName]}

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Chemical Structure| 18869-29-9
Chemical Structure| 18869-29-9
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Product Details of [ 18869-29-9 ]

CAS No. :18869-29-9 MDL No. :MFCD00136904
Formula : C16H16 Boiling Point : -
Linear Structure Formula :- InChI Key :KINZBJFIDFZQCB-VAWYXSNFSA-N
M.W : 208.30 Pubchem ID :5462964
Synonyms :

Calculated chemistry of [ 18869-29-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.74
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.22
Log Po/w (XLOGP3) : 4.92
Log Po/w (WLOGP) : 4.26
Log Po/w (MLOGP) : 5.75
Log Po/w (SILICOS-IT) : 5.06
Consensus Log Po/w : 4.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.65
Solubility : 0.00462 mg/ml ; 0.0000222 mol/l
Class : Moderately soluble
Log S (Ali) : -4.66
Solubility : 0.00459 mg/ml ; 0.000022 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.78
Solubility : 0.000343 mg/ml ; 0.00000164 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.02

Safety of [ 18869-29-9 ]

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 [ 18869-29-9 ]

* 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 [ 18869-29-9 ]

[ 18869-29-9 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 18869-29-9 ]
  • [ 538-39-6 ]
YieldReaction ConditionsOperation in experiment
92% With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 20℃;
With 1,4-dioxane; nickel Hydrogenation;
With zeolite Ca Y In hexane at 22℃; for 1h; Yield given;
With CaY zeolite In hexane Ambient temperature;

  • 2
  • [ 18869-29-9 ]
  • (1E)-1,2-bis[3-(bromomethyl)phenyl]diazene [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 6h; Reflux;
55% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 6h; Heating;
30% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile)
29% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene for 24h; Reflux;
With N-Bromosuccinimide; chloroform; dibenzoyl peroxide
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); dibenzoyl peroxide In tetrachloromethane; chloroform Heating;

  • 3
  • [ 104-87-0 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
96% With titanium tetrachloride; zinc
96% With titanium tetrachloride; zinc In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;
91% With titanium tetrachloride; zinc In tetrahydrofuran at 110℃; for 0.166667h; microwave irradiation;
90% With titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Reflux;
87% With chromium dichloride; trichlorosilane In tetrahydrofuran at 65℃; for 8h;
86% With 1,2-bis-(chlorodimethylsilyl)ethane; mercury; zinc In tetrahydrofuran Ambient temperature;
85% With titanium tetrachloride; zinc In tetrahydrofuran for 24h;
85% With titanium tetrachloride; zinc In tetrahydrofuran at 0 - 85℃; Sealed tube; Inert atmosphere; diastereoselective reaction; McMurry reaction general procedure for stilbene 9 synthesis General procedure: To a stirred suspension of Zn powder (4.70 g, 71.9 mmol) in THF (50.0 mL, 0.60 M) in a flame dried sealed tube at 0 °C was added TiCl4 (3.93 mL, 35.9 mmol) dropwise. The mixture was stirred at 0 °C for 30 min and then aldehyde (29.9 mmol) was added. The mixture was then refluxed for 24 h and then slowly quenched with water (25 mL) at 0 °C. The mixture was then extracted with CH2Cl2 (3*75 mL), and the combined organic extracts dried over sodium sulfate, filtered, and evaporated in vacuo. Purification using flash column chromatography (ethyl acetate/hexanes) afforded the product stilbene 9.
84% With titanium tetrachloride; zinc In tetrahydrofuran for 24h; Inert atmosphere; Reflux;
79% With titanium tetrachloride; zinc In tetrahydrofuran Heating;
71% Stage #1: 4-methylbenzyltriphenylphosphonium bromide With sodium hydride In toluene for 6h; Heating / reflux; Stage #2: 4-methyl-benzaldehyde In toluene for 6h; Heating / reflux; 7 Example 7; Preparation of 4,4'-dimethyl-stilbene; 2.4 g(5.37 mmol) of (4-methylbenzyl)triphenylphosphonium bromide and 0.98 g(60%, 24.4 mmol) of NaH were refluxed in toluene for 6 hours. After cooled down, 0.586 g(4.88 mmol) of 4-methylbenzaldehyde was introduced gradually to the solution to be refluxed again for 6 hours. The resulted product was treated with water to be extracted with ethyl acetate. The solvent was distilled off and the residue was recrystallized in ethanol. Yield; 71%. 1H-NMR(CDCl3): 7.64(d, 4H, Ar-H), 7.16(d, 4H, Ar-H), 6.90(s, 2H, vinyl).
With acid bei der elektrolytischen Reduktion;
With lithium aluminium tetrahydride; titanium(III) chloride

Reference: [1]Feast; Loevenich; Puschmann; Taliani [Chemical Communications, 2001, # 5, p. 505 - 506]
[2]Sivamani, Jayaraman; Ashokkumar, Veeramanoharan; Sadhasivam, Velu; Duraimurugan, Kumaraguru; Siva, Ayyanar [RSC Advances, 2014, vol. 4, # 104, p. 60293 - 60299]
[3]Stuhr-Hansen, Nicolai [Tetrahedron Letters, 2005, vol. 46, # 33, p. 5491 - 5494]
[4]Nojima, Masataka; Ohta, Yoshihiro; Yokozawa, Tsutomu [Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5682 - 5685]
[5]Baati, Rachid; Mioskowski, Charles; Barma, Deb; Kache, Rajashaker; Falck [Organic Letters, 2006, vol. 8, # 14, p. 2949 - 2951]
[6]Afonso, Carlos A. M.; Motherwell, William B.; O'Shea, Dennis M.; Roberts, Lee R. [Tetrahedron Letters, 1992, vol. 33, # 27, p. 3899 - 3902]
[7]Location in patent: scheme or table Garner, Logan E.; Park, Juhyun; Dyar, Scott M.; Chworos, Arkadiusz; Sumner, James J.; Bazan, Guillermo C. [Journal of the American Chemical Society, 2010, vol. 132, # 29, p. 10042 - 10052]
[8]Rosocha, Gregory; Batey, Robert A. [Tetrahedron, 2013, vol. 69, # 41, p. 8758 - 8768]
[9]Zhang, Yan; Xia, Mingze; Li, Min; Ping, Qian; Yuan, Zhenbo; Liu, Xuanzhong; Yin, Huimin; Huang, Shuping; Rao, Yijian [Journal of Organic Chemistry, 2021, vol. 86, # 21, p. 15284 - 15297]
[10]Harris, Lisa D.; Jenkins, Robert L.; Tomkinson, Nicholas C.O. [Tetrahedron Letters, 2005, vol. 46, # 10, p. 1627 - 1629]
[11]Current Patent Assignee: SEOUL NATIONAL UNIVERSITY; Dongwoo Fine-Chem (in: Sumitomo Chemical); SUMITOMO CHEMICAL COMPANY LIMITED - US2007/149799, 2007, A1 Location in patent: Page/Page column 4
[12]Law [Journal of the Chemical Society, 1907, vol. 91, p. 759]
[13]Komatsu, Koichi; Niwa, Tadashi; Akari, Hideaki; Okamoto, Kunio [Journal of Chemical Research, Miniprint, 1985, # 8, p. 2847 - 2881]
  • 4
  • [ 18869-29-9 ]
  • [ 1576-67-6 ]
YieldReaction ConditionsOperation in experiment
90% With iodine; methyloxirane In benzene for 8h; Irradiation; in the presence of various combinations of I2, air, propylene oxide, HI; other substrates;
90% With iodine; methyloxirane In benzene for 8h; Irradiation;
With iodine Irradiation;
With iodine In cyclohexane Irradiation;
Irradiation;
With borax In dimethylsulfoxide-d6; water-d2 for 4h; Irradiation;

  • 5
  • [ 623-73-4 ]
  • [ 18869-29-9 ]
  • ethyl trans-2,3-bis(4-methylphenyl)cyclopropanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tris-(4-bromophenyl)aminium hexachloroantimonate In dichloromethane for 3h; other substituted trans-stilbenes; also in the presence of tris(2,4-dibromophenyl)aminium hexachloroantimonate; relative rate constants for the cyclopropanation of var. stilbenes;
78% With tris-(4-bromophenyl)aminium hexachloroantimonate In dichloromethane for 3h;
78% With [Cr(bathophenanthroline)3](BF4)3 In dichloromethane; 1,2-dichloro-ethane for 24h; Irradiation; Sealed tube;
With lithium perchlorate In acetonitrile Ambient temperature; electrochemical cyclopropanation; other trans-stilbenes;
With copper(II) sulfate In benzene at 75℃;

  • 6
  • [ 622-97-9 ]
  • [ 60126-95-6 ]
  • [ 18869-29-9 ]
  • [ 613-33-2 ]
  • [ 2919-20-2 ]
  • 7
  • [ 108-05-4 ]
  • [ 624-31-7 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
83% With tributyl-amine at 100℃; for 24h;
  • 8
  • [ 18869-29-9 ]
  • [ 2510-55-6 ]
  • (1R,2S,2aS,10bR)-1,2-Di-p-tolyl-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carbonitrile [ No CAS ]
  • (1S,2R,2aS,10bR)-1,2-Di-p-tolyl-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% In benzene Irradiation;
  • 9
  • [ 18869-29-9 ]
  • [ 2510-76-1 ]
YieldReaction ConditionsOperation in experiment
99% With 8,9-bis((R)-2-(isobutyryloxy)propyl)-7,10-dimethoxyperyleno-[1,12-def][1,3]dioxepine-5,6,11,12-tetrayl tetrakis(2-methylpropanoate) In toluene at 20℃; Schlenk technique; Inert atmosphere; Irradiation;
98% With bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; oxygen In acetonitrile at 20℃; Irradiation;
98% With sodium hydroxide In water; acetonitrile at 20℃; for 24h; Irradiation;
80% In benzene for 40h; photoisomerization;
66% With covalent organic framework constructed from melamine and 2,4,6-triformylphloroglucinol In N,N-dimethyl-formamide at 20℃; for 18h; Irradiation;
15% With borax In dimethylsulfoxide-d6; water-d2 for 1h; Irradiation;
With 9,10-Dicyanoanthracene In acetonitrile Irradiation;
In pentane Irradiation; Ea; other solvents;
In benzene for 4h; UV-irradiation;
80 %Spectr. In d(4)-methanol at 20℃; Inert atmosphere; UV-irradiation;

  • 10
  • [ 18869-29-9 ]
  • [ 104-87-0 ]
YieldReaction ConditionsOperation in experiment
90% With aluminum oxide; potassium permanganate In dichloromethane; water for 1h; Ambient temperature;
82% With ruthenium trichloride; Oxone; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 0.3h;
With air; 9,10-Dicyanoanthracene In acetonitrile Irradiation; quantum yield for aldehyde formation and ion pair separation;
79 %Spectr. With iodine; oxygen; trifluoroacetic acid In methanol; ethyl acetate for 20h; Irradiation; Photooxidation; Typical Procedure General procedure: A solution of trans-4,4′-di-tert-butylstilbene (1a) (0.15mmol), I2 (0.015 mmol), and TFA (0.03 mmol) in dryMeOH-EtOAc (1:2 mL) was stirred in a Pyrex test-tube under air (open), and externally irradiated with four 22 W fluorescent lamps for 20 h. The mixture was quenched withaq Na2S2O3 solution and extracted with EtOAc (3 × 5 mL). The combined organic layer was washed with brine (20 mL)and aq HCl (2 M, 2 × 20 mL), dried over MgSO4 and concentrated in vacuo. Purification of the crude residue by column chromatography (hexane-EtOAc, 50:1) provided 4-tert-butylbenzaldehyde (2a) (41.1 mg, 84%).

  • 11
  • [ 18869-29-9 ]
  • trans-2,3-bis(4-methylphenyl)oxirane [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Cooling with ice;
58% With N-benzyl-N,N,N-triethylammonium chloride; N-chloromethanesulfonamide sodium salt; benzaldehyde In acetonitrile at 20℃; for 7h;
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water for 24h; Ambient temperature; pH > 8;
45 % Chromat. With 18-crown-6 ether; diethyl chlorophosphate In acetonitrile; benzene at 20℃; for 2h;
With 3-chloro-benzenecarboperoxoic acid In methanol; dichloromethane; water at 20℃; for 15h; Ionic liquid; Inert atmosphere; Starting material solution in CH2Cl2/BMIM incapsulated within polydimethylsiloxane thimble;
69 %Chromat. With 1H-imidazole; iron(III) chloride hexahydrate; 2-ethoxycarbonyl-1-cyclopentanone In acetonitrile at 20℃; for 20h; chemoselective reaction;

  • 12
  • [ 18869-29-9 ]
  • [ 38424-10-1 ]
YieldReaction ConditionsOperation in experiment
With potassium In 1,2-dimethoxyethane temperature: dry ice-acetone;
  • 13
  • [ 18869-29-9 ]
  • [ 75801-34-2 ]
YieldReaction ConditionsOperation in experiment
With 3-chloro-benzenecarboperoxoic acid
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;
  • 14
  • [ 26204-07-9 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
63% With sodium tetrahydroborate; Co(dmgH)2 In methanol; water for 0.666667h;
  • 15
  • [ 2510-76-1 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
100% With cadmium(II) sulphide In dichloromethane Irradiation;
100% With cadmium(II) sulphide In dichloromethane Irradiation; relative rate;
85% With borax In dimethylsulfoxide-d6; water-d2 for 0.5h; Irradiation;
With iodine In Petroleum ether Heating;
In hexane for 3h; Yield given;
With tellurium tetrachloride In chloroform for 1h; Ambient temperature; isomerization;
With 9,10-Dicyanoanthracene In acetonitrile Irradiation;
With dibutylbis(cyclopentadienyl)zirconium In tetrahydrofuran; benzene-d6 at 23℃;
With 4-methylbenzylthiol; catalyst; caesium carbonate; bis(pinacol)diborane In N,N-dimethyl-formamide at 25℃; for 24h; Irradiation; Inert atmosphere;

  • 16
  • [ 23063-36-7 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
92% With iron(II) oxalate dihydrate In N,N-dimethyl-formamide at 155 - 160℃; for 1h;
  • 17
  • [ 51419-59-1 ]
  • [ 18869-29-9 ]
  • [ 95495-85-5 ]
  • 18
  • [ 51419-59-1 ]
  • [ 18869-29-9 ]
  • [ 2510-76-1 ]
  • [ 104-87-0 ]
  • 20
  • [ 104-87-0 ]
  • [ 1530-37-6 ]
  • [ 18869-29-9 ]
  • [ 2510-76-1 ]
YieldReaction ConditionsOperation in experiment
1: 28% 2: 66% With sodium methylate In methanol at 50℃; for 3.5h; Inert atmosphere;
With potassium carbonate In 1,4-dioxane
1: 85 % Chromat. 2: 15 % Chromat. With potassium hydroxide; 18-crown-6 ether In dichloromethane at -70℃;
  • 21
  • [ 104-87-0 ]
  • [ 104-82-5 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
81% With tetramethylorthosilicate; (trisethoxysilyl)ethyldiphenylphosphine; [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane In toluene at 110℃; for 12h;
With sodium methylate; triethyl phosphite Yield given. Multistep reaction;
  • 22
  • [ 104-87-0 ]
  • [ 18869-29-9 ]
  • [ 2870-30-6 ]
YieldReaction ConditionsOperation in experiment
85% With diethyl sodio phosphonate In benzene at 130℃; for 11.5h; sealed tube;
  • 23
  • [ 74-85-1 ]
  • [ 874-60-2 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
45% With N,N'-dimethylbenzylamine; palladium diacetate In xylene at 120℃; for 7.5h;
  • 24
  • [ 18869-29-9 ]
  • [ 38424-23-6 ]
YieldReaction ConditionsOperation in experiment
93% With bromine; 1-n-butyl-3-methylimidazolim bromide at 20℃;
With tetra-N-butylammonium tribromide In 1,2-dichloro-ethane at 25℃; other cis- and trans-stilbenes;
With bromine Irradiation;
With tetra-N-butylammonium tribromide In 1,2-dichloro-ethane at 25℃;
With tetrabutylammomium bromide; tetra-N-butylammonium tribromide In 1,2-dichloro-ethane

  • 25
  • (E)-4,4'-dimethylstilbene [ No CAS ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
88% With sodium dithionite; sodium hydrogencarbonate In N,N-dimethyl-formamide for 16h; Ambient temperature;
  • 26
  • [ 18869-29-9 ]
  • [ 156473-34-6 ]
  • (+)-(2R,3R)-trans-2,3-di(p-tolyl)oxirane: [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Oxone; propan-2-one-1,3-diol (R)-3,3'-di(1,3-dioxan-2-yl)-1,1'-binaphthyl-2,2'-dicarboxylate; edetate disodium; sodium hydrogencarbonate In 1,2-dimethoxyethane at 0℃; for 20h; Title compound not separated from byproducts;
With Oxone; (R)-2,10-dibromo-5H-dianaphtho<2,1-g:1',2'-i><1,5>dioxacycloundecin-3,6,9(7H)-trione; edetate disodium; sodium hydrogencarbonate In 1,2-dimethoxyethane at 0℃; for 20h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Stage #1: (E)-4,4'-dimethylstilbene With Pyridine-2,6-dicarboxylic acid; iron(III) chloride at 20℃; for 1h; Stage #2: With dihydrogen peroxide In water for 1h; Further stages. Title compound not separated from byproducts.;
Stage #1: (E)-4,4'-dimethylstilbene With Pyridine-2,6-dicarboxylic acid; iron(III) chloride hexahydrate; C28H28N2O2S In tert-Amyl alcohol at 20℃; for 0.5h; Stage #2: With dihydrogen peroxide In tert-Amyl alcohol; water at 20℃; for 1h; optical yield given as %ee; enantioselective reaction;
With 2-((E)-(((1R,2R)-2-amino-1,2-diphenylethyl)imino)methyl)-4,6-di-tert-butylphenol; Pyridine-2,6-dicarboxylic acid; iron(III) chloride hexahydrate; dihydrogen peroxide; 6,6'-((1E,1'E)-(((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(azanylylidene))bis(methanylylidene))bis(2,4-di-tert-butylphenol) In dichloromethane at 20℃; for 1.5h; enantioselective reaction; 4.7.1. General procedure for the oxidation of trans-stilbene and derivatives General procedure: FeCl3·6H2O (0.017 mmol), H2Pydic (0.017 mmol), and ligand 2 (0.033 mmol) were dissolved in dichloromethane (1.6 mL). The mixture was stirred for 1 h at room temperature after which the addition of the substrate (0.167 mmol) and H2O2 (30%, 0.250 mmol) followed. The reaction mixture was stirred for additional 1.5 h at room temperature. The reaction was quenched with Na2SO3. The product was directly purified by column chromatography on silica gel. The product was obtained as a colorless solid. The enantiomeric excess was determined by chiral HPLC analysis.
55 % ee With Pyridine-2,6-dicarboxylic acid; iron(III) chloride hexahydrate; C51H84N2O2SSi5; dihydrogen peroxide In tert-Amyl alcohol at 20℃; for 1h; Overall yield = 95 %; enantioselective reaction;

  • 27
  • [ 18869-29-9 ]
  • [ 66768-19-2 ]
YieldReaction ConditionsOperation in experiment
82% With osmium(VIII) oxide; dihydroquinidine 9-O-(4-chlorobenzoate); potassium carbonate; potassium hexacyanoferrate(III) In water; <i>tert</i>-butyl alcohol for 24h; Ambient temperature;
68% With methanesulfonamide; AD-mix-β In water; <i>tert</i>-butyl alcohol at 0℃; for 48h;
With 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine In ethyl acetate; <i>tert</i>-butyl alcohol at 20℃;
  • 28
  • [ 78-08-0 ]
  • [ 459-44-9 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
56% In methanol at 60℃; for 1h;
  • 29
  • [ 67-56-1 ]
  • [ 18869-29-9 ]
  • C17H19BrO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bromine at 20℃; for 4h;
  • 30
  • [ 18869-29-9 ]
  • 2-bromo-1,2-di-<i>p</i>-tolyl-ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide In dimethyl sulfoxide
  • 31
  • [ 623-73-4 ]
  • [ 18869-29-9 ]
  • 2,3-di-<i>p</i>-tolyl-cyclopropanecarboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tris-(4-bromophenyl)aminium hexachloroantimonate In dichloromethane at 0℃;
  • 32
  • [ 142087-16-9 ]
  • C15H16N2O2S [ No CAS ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
64% With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 12h;
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate; dimethyl sulfoxide at 190℃;
  • 34
  • [ 459-44-9 ]
  • [ 73839-45-9 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: (E)-trimethyl[2-(4-methylphenyl)ethenyl]silane With boron trichloride In dichloromethane at 0℃; for 2h; Stage #2: 4-methylbenzenediazonium tetrafluoroborate With palladium diacetate In 1,4-dioxane at 20℃; for 24h; Further stages.;
  • 35
  • [ 1530-37-6 ]
  • [ 18869-29-9 ]
  • [ 2510-76-1 ]
YieldReaction ConditionsOperation in experiment
1: 43% 2: 32% With 18-crown-6 ether; oxygen; potassium carbonate In toluene at 60 - 70℃; for 8h;
  • 36
  • [ 622-97-9 ]
  • [ 624-31-7 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 3h; Green chemistry;
96% With potassium carbonate In water; N,N-dimethyl-formamide at 70℃; for 0.133333h; Microwave irradiation; Green chemistry;
96% With potassium phosphate In N,N-dimethyl-formamide at 100℃; for 10h; General procedure for the Heck reaction of aryl halides General procedure: A mixture of aryl halide (1.0 mmol), styrene (2 mmol), PS-tsu-Pd(II) complex (3) (0.005 mmol), K3PO4 (2.0 mmol), and DMF (2 mL) was stirred at 100 °C for 10 h. After completion of the reaction, the mixture was filtered to recover the catalyst. Then the experimental procedure was same as above.
93% With lithium hydroxide monohydrate; C18H21N3O2Pd In N,N-dimethyl-formamide at 120℃; for 15h; Typical procedure for Heck reaction of aryl iodides General procedure: The 100 mL RB-flask was charged with aryl iodides (1.0 mmol), alkenes (2.0 mmol), LiOH*H2O (1.2 mmol) and the catalyst (0.001 mol%) in N,N-dimethylformamide (2.0 mL). The reaction mixture was heated at 120 oC for 15 h and the progress of reaction was monitored by TLC. At the end of the reaction, the reaction mixture was cooled to room temperature and was diluted with EtOAc (20 mL), washed with 1N aq. HCl and water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the Heck product in high purity.
93% With Pd(2-picolinate)(PPh<SUB>3</SUB>)(OTs); sodium acetate In N,N-dimethyl-formamide at 120℃; for 0.25h; General experimental procedure for the Heck reaction General procedure: To a mixture of Iodobenzene (1.0 mmol), styrene (1.2 mmol), NaOAc (1.5 mmol), Catalyst (0.007 mmol) and DMF (3mL) was added in round bottom flask. (No inert gas protection was needed.). The reaction was carried out at 120 °C for 15 min. Upon completion of reaction as indicated by TLC, the reaction mixture was poured in crushed ice-water, extracted with ethyl acetate, dried over anhydrous Na2SO4, concentrated in vacuum to give crude product which was purified through column chromatography on silica gel (100-200) to afforded pure stilbenes in 90-98% yields.
91% With C11H12N2O3Pd; sodium carbonate In N,N-dimethyl-formamide at 145℃; for 20h;
68% With potassium phosphate; palladium diacetate In N,N-dimethyl acetamide at 140℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube;
With triethylamine at 70℃;

  • 37
  • [ 104-82-5 ]
  • [ 18869-29-9 ]
  • [ 106-42-3 ]
  • [ 538-39-6 ]
  • [ 4957-14-6 ]
YieldReaction ConditionsOperation in experiment
60% With magnesium at 600℃;
  • 38
  • [ 18869-29-9 ]
  • [ 99-94-5 ]
YieldReaction ConditionsOperation in experiment
91% With Oxone; osmium(VIII) oxide In N,N-dimethyl-formamide; <i>tert</i>-butyl alcohol at 20℃; for 3h;
  • 39
  • [ 400848-58-0 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
90% With samarium diiodide In tetrahydrofuran at 20℃; for 0.0833333h;
  • 40
  • [ 74-85-1 ]
  • [ 99-90-1 ]
  • [ 622-97-9 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
1: 58% 2: 10% With 1,4-dicyclohexyl-diazabutadiene; tetrabutylammomium bromide; caesium carbonate In N,N-dimethyl acetamide at 100℃; for 14h;
  • 41
  • [ 622-97-9 ]
  • [ 106-38-7 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
98% With {1,3-bis[2,6-bis(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}dichloro(pyridine)palladium; caesium carbonate In neat (no solvent) at 100℃; for 12h; 4.2. General procedure for Heck Cross-Coupling reactions General procedure: To a single-necked flask (15 mL) equipped with a stir bar charge with 1 (1 eq, 1 mmol), 2 (1 eq, 1.2 mmol), NHC-Pd (II)-Py (0.01 eq, 0.06 g) and Cs2CO3 (0.3 eq, 0.1 g). Then the reaction flask was stirred at 100 °C for 12 h, and then the reaction mixture was cooled to room temperature. After removing the solvent under reduced pressure, the pure product was obtained by silica gel column chromatography (eluent: petroleum ether/ethyl acetate).
96% With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride In N,N-dimethyl acetamide at 140℃; for 12h;
93% With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 6h; Green chemistry;
92% With C11H12N2O3Pd; sodium carbonate In N,N-dimethyl-formamide at 145℃; for 20h;
92% With lithium hydroxide monohydrate; C18H21N3O2Pd In N,N-dimethyl-formamide at 145℃; for 15h; Typical procedure for Heck reaction of aryl Bromides General procedure: The 100 mL RB-flask was charged with aryl bromides (1.0 mmol), alkenes (2.0 mmol), LiOH*H2O (1.2 mmol) and the catalyst (0.001 mol%) in N,N-dimethylformamide (2.0 mL). The reaction mixture was heated at 145 oC for 15 h and the progress of reaction was monitored by TLC. At the end of the reaction, the reaction mixture was cooled to room temperature and was diluted with EtOAc (20 mL), washed with 1N aq. HCl and water.The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the Heck product in high purity.
92% With potassium phosphate; C24H22ClN3OPdSe; tetrabutylammomium bromide In water at 110℃; for 12h;
90% With potassium carbonate In water; N,N-dimethyl-formamide at 70℃; for 3h; Inert atmosphere; General procedure for Mizoroki-Heck C-C coupling reactions General procedure: The potential activity of the newly prepared Pd/TATAE catalyst was analyzed in the Mizoroki-Heck cross-coupling reaction (Scheme 2). Aryl bromide (1 mmol), styrene (1.2 mmol), K2CO3 (1.2 mmol), and Pd/TATAE (20 mg) were taken in dimethylformamide (DMF)/water mixture (1:2 ratio, 2 mL), and the mixture was stirred at 70 °C for about 3 h. After reaction completion (monitored by TLC), the reaction mixture was diluted with 5 mL ethyl acetate, then the catalyst was removed by simple filtration using Whatman-40 filter paper. The filtrate was extracted with excess amount of ethyl acetate, then concentrated under reduced pressure. The crude product was further purified by silica gel (60-120 mesh) column chromatography (petroleum ether/ethyl acetate) to afford the corresponding products.
88% With 2BF4(1-)*C42H38Fe2N6O2Pd2(2-) In water; N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;
86% With C36H26ClN2O2PPd; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere; Typical procedure for the Mizoroki-Heck reaction of aryl bromides with terminal olefins General procedure: In an oven-dried round bottom flask under an atmosphere of nitrogen at room temperature were placed complex 1 (25 mol) and DMF (5 mL). After stirring for 5 min, the aryl bromide (5 mmol), olefinic substrate (10 mmol) and K2CO3 (6 mmol) were introduced into the reaction flask. The reaction mixture was heated at 100 °C for 10 h under an atmosphere of nitrogen. At the end of the reaction, the reaction mixture was cooled to room temperature, diluted with EtOAc (20 mL), washed dil. HCl and water. The combined organic layer was dried over anhydrous Na2SO4 and stripped off the solvent under reduced pressure.The residue was subjected to column chromatography on silica gel using ethyl acetate and hexane mixtures to afford the Mizoroki-Heck product in high purity. The products were characterized by 1H-NMR analysis.
83% With lithium hydrochloride monohydrate; C30H20F12N6O2Pd In N,N-dimethyl-formamide at 145℃; for 10h;
69% With [PdBr2(PPh3)2]; potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 8h; Inert atmosphere; stereoselective reaction; Typical procedure for the Mizoroki-Heck reaction of aryl bromides with terminal olefins General procedure: In an oven-dried round bottom flask under an atmosphere of nitrogen at room temperature were placed complex 1 (0.0005 mmol) and DMF (3 mL). After stirring for 5 min, the aryl bromide (5 mmol), olefinic substrate (10 mmol) and K2CO3 (6 mmol) were introduced into the reaction flask. The reaction mixture was heated at 100 °C for the required reaction time under an atmosphere of nitrogen. At the end of the reaction, the reaction mixture was cooled to room temperature, diluted with EtOAc (20 mL), washed dil. HCl and water. The combined organic layer was dried over anhydrous Na2SO4 and stripped off the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel using ethyl acetate and hexane mixtures to afford the Mizoroki-Heck product in high purity. The products were characterized by 1H NMR analysis
60% With C26H24N6NiS2; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere; Typical procedure for the Mizoroki-Heckreaction of aryl bromides with terminal olefins General procedure: In an oven-dried round bottom flask under an atmosphere of nitrogen atroom temperature were placed complex 1(25 mmol)and DMF (5 mL). After stirringfor 5 min, the aryl bromide (5 mmol), olefinic substrate (10 mmol) and K2CO3(6 mmol) were introduced into the reaction flask. The reaction mixture washeated at 110 °C for 24 h under an atmosphere of nitrogen. At the end of thereaction, the reaction mixture was cooled to room temperature, diluted withEtOAc (20 mL), washed dil. HCl and water. The combined organic layer was dried over anhydrous Na2SO4and stripped off the solvent under reduced pressure. The residue was subjectedto column chromatography on silica gel using ethyl acetate and hexane mixturesto afford the Mizoroki-Heck product in high purity. The products werecharacterized by 1H-NMR analysis.

Reference: [1]Li, Dan; Tian, Qingqiang; Wang, Xuetong; Wang, Qiang; Wang, Yin; Liao, Siwei; Xu, Ping; Huang, Xin; Yuan, Jianyong [Synthetic Communications, 2021, vol. 51, # 13, p. 2041 - 2052]
[2]Wang, Ai-E; Xie, Jian-Hua; Wang, Li-Xin; Zhou, Qi-Lin [Tetrahedron, 2005, vol. 61, # 1, p. 259 - 266]
[3]Rezaei, Saghar; Landarani-Isfahani, Amir; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Mohammadpoor-Baltork, Iraj [RSC Advances, 2016, vol. 6, # 95, p. 92463 - 92472]
[4]Kantam, M. Lakshmi; Srinivas; Yadav, Jagjit; Likhar, Pravin R.; Bhargava, Suresh [Journal of Organic Chemistry, 2009, vol. 74, # 13, p. 4882 - 4885]
[5]Kantam, M. Lakshmi; Annapurna, Manne; Likhar, Pravin R.; Srinivas; Mirzadeh, Nedaossadat; Bhargava, Suresh K. [Journal of Organometallic Chemistry, 2013, vol. 723, p. 129 - 136]
[6]Sharma, Kamal Nayan; Satrawala, Naveen; Srivastava, Avinash Kumar; Ali, Munsaf; Joshi, Raj Kumar [Organic and Biomolecular Chemistry, 2019, vol. 17, # 40, p. 8969 - 8976]
[7]Sadhasivam, Velu; Mathappan, Mariyappan; Harikrishnan, Muniyasamy; Chithiraikumar, Chinnadurai; Murugesan, Sepperumal; Siva, Ayyanar [Research on Chemical Intermediates, 2018, vol. 44, # 4, p. 2853 - 2866]
[8]Location in patent: scheme or table Das, Raj K.; Saha, Biswajit; Rahaman, S. M. Wahidur; Bera, Jitendra K. [Chemistry - A European Journal, 2010, vol. 16, # 48, p. 14459 - 14468]
[9]Muthumari, Subramanian; Mohan, Nanjan; Ramesh, Rengan [Tetrahedron Letters, 2015, vol. 56, # 28, p. 4170 - 4174]
[10]Location in patent: experimental part Srinivas, Pottabathula; Srinivas, Keesara; Likhar, Pravin R.; Sridhar, Balsubramanian; Mohan, Kakita Veera; Bhargava, Suresh; Kantam, Mannepalli Lakshmi [Journal of Organometallic Chemistry, 2011, vol. 696, # 3, p. 795 - 801]
[11]Prabhu, Rupesh Narayana; Ramesh, Rengan [Tetrahedron Letters, 2012, vol. 53, # 44, p. 5961 - 5965,5]
[12]Suganthy, Pandimuni Kalpaga; Prabhu, Rupesh Narayana; Sridevi, Venugopal Shamugham [Tetrahedron Letters, 2013, vol. 54, # 42, p. 5695 - 5698]
  • 42
  • [ 622-97-9 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane for 2h; Heating;
89% With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 4h;
76% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In methanol; dichloromethane; water at 45℃; for 8.5h; Ionic liquid; Inert atmosphere; Catalyst solution in CH2Cl2/BMIM incapsulated within polydimethylsiloxane thimble;
72% Stage #1: 1-ethenyl-4-methylbenzene With titanium tetrachloride In tetrahydrofuran at -78 - 20℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: With zinc In tetrahydrofuran for 0.0333333h; Schlenk technique; Inert atmosphere; Stage #3: In tetrahydrofuran at 80℃; for 3h; Schlenk technique; Inert atmosphere;
30% With Grubbs catalyst first generation In dichloromethane at 40℃;
With Grubbs catalyst first generation In dichloromethane Heating;
89 % Turnov. In toluene at 85℃; for 2h;

  • 43
  • [ 104-87-0 ]
  • [ 18869-29-9 ]
  • [ 54656-06-3 ]
YieldReaction ConditionsOperation in experiment
1: 75% 2: 21% With tetrachlorosilane; zinc In dichloromethane at 20℃; for 2h;
  • 45
  • [ 104-82-5 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
95% With Benzyl phenyl selenoxide; potassium hexamethylsilazane In toluene at 25℃; for 4h; Inert atmosphere;
86% With Triisopropyl borate; cesium fluoride; tricyclohexylphosphine In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; 2 Example 2: Synthesis of trans-4,4'-dimethyl-1,2-stilbene In a 25mL reactor, add 4-methylbenzyl chloride (0.084g, 0.6mmol), cesium fluoride (0.273g, 1.8mmol), tricyclohexylphosphine (0.034g, 0.12mmol), triisopropyl borate ( 0.170 g, 0.9 mmol), 5 mL of anhydrous tetrahydrofuran was added, and the mixture was stirred for 12 h at 100°C under nitrogen. Column chromatography separation (silica gel, 200-300 mesh; developing solvent, petroleum ether) to obtain 0.054 g of trans-4,4'-dimethyl-1,2-stilbene with a yield of 86%.
84% With benzyl phenyl sulfoxide; potassium <i>tert</i>-butylate at 80℃; for 12h; Green chemistry; stereoselective reaction;
84% With benzyl phenyl sulfoxide; potassium <i>tert</i>-butylate at 80℃; for 12h; Inert atmosphere;
82% With potassium phenyl selenide In 1,2-dimethoxyethane for 5h; Inert atmosphere; Sealed tube;
72% With sodium 4-methylbenzenesulfinate; potassium hydroxide In dimethyl sulfoxide at 100℃; for 16h;
Multi-step reaction with 2 steps 1: toluene / 8 h / Heating 2: 32 percent / O2; 18-crown-6 ether; K2CO3 / VO(acac)2 / toluene / 8 h / 60 - 70 °C
Multi-step reaction with 2 steps 1: CHCl3 / 3 h / Heating 2: 39.6 percent / LiOMe / methanol
Multi-step reaction with 2 steps 1: 76 percent / lithium sand / diethyl ether / 0.5 h / 0 °C 2: 80 percent / p-toluenesulfonic acid / benzene / 4 h / Heating
Multi-step reaction with 2 steps 1: 1.) aqueous sodium sulfite; 2.) phosphorus pentachloride, phosphorus oxychloride / 1.) trioctylmethylammonium chloride / 1.) 100 deg C; 2.) 0 deg C
Multi-step reaction with 2 steps 1: 1.) aqueous sodium sulfite; 2.) phosphorus pentachloride, phosphorus oxychloride / 1.) trioctylmethylammonium chloride / 1.) 100 deg C; 2.) 0 deg C 2: 1.) triethylamine / 1.) THF, -50 deg C, 1 h; 2.) room temperature
14.8 mg With C6H5OS(1-)*K(1+) at 20 - 80℃; for 6h; Inert atmosphere;

Reference: [1]Zheng, Zhipeng; Trofymchuk, Oleksandra S.; Kurogi, Takashi; Varela, Elena; Mindiola, Daniel J.; Walsh, Patrick J. [Advanced Synthesis and Catalysis, 2020, vol. 362, # 3, p. 659 - 666]
[2]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN112299937, 2021, A Location in patent: Paragraph 0050-0052
[3]Schwan, Adrian L. [ChemCatChem, 2015, vol. 7, # 2, p. 226 - 227]
[4]Zhang, Mengnan; Jia, Tiezheng; Yin, Haolin; Carroll, Patrick J.; Schelter, Eric J.; Walsh, Patrick J. [Angewandte Chemie - International Edition, 2014, vol. 53, # 40, p. 10755 - 10758][Angew. Chem., 2014, vol. 126, # 40, p. 10931 - 10934,4]
[5]Trofymchuk, Oleksandra S.; Zheng, Zhipeng; Kurogi, Takashi; Mindiola, Daniel J.; Walsh, Patrick J. [Advanced Synthesis and Catalysis, 2018, vol. 360, # 8, p. 1685 - 1692]
[6]Zhao, Feng; Luo, Jiaying; Tan, Qi; Liao, Yunfeng; Peng, Shengming; Deng, Guo-Jun [Advanced Synthesis and Catalysis, 2012, vol. 354, # 10, p. 1914 - 1918]
[7]Shi, Min; Xu, Bo [Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 294 - 297]
[8]Rosa, Joaquin Campos; Galanakis, Dimitrios; Ganellin, C. Robin; Dunn, Philip M. [Journal of Medicinal Chemistry, 1996, vol. 39, # 21, p. 4247 - 4254]
[9]Burkow, Ivan C.; Sydnes, Leiv K.; Ubeda, Danielle C. N. [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, # 4, p. 235 - 244]
[10]Nakayama, Juzo; Tanuma, Mitsuru; Honda, Yoshiko; Hoshino, Masamatsu [Tetrahedron Letters, 1984, vol. 25, # 40, p. 4553 - 4556]
[11]Nakayama, Juzo; Tanuma, Mitsuru; Honda, Yoshiko; Hoshino, Masamatsu [Tetrahedron Letters, 1984, vol. 25, # 40, p. 4553 - 4556]
[12]Zhang, Mengnan; Jia, Tiezheng; Sagamanova, Irina K.; Pericás, Miquel A.; Walsh, Patrick J. [Organic Letters, 2015, vol. 17, # 5, p. 1164 - 1167]
  • 46
  • [ 603-35-0 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 8 h / Heating 2: 32 percent / O2; 18-crown-6 ether; K2CO3 / VO(acac)2 / toluene / 8 h / 60 - 70 °C
  • 47
  • [ 18869-29-9 ]
  • (4R,5R)-2,2-Dimethyl-4,5-di-p-tolyl-[1,3]dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: p-TsOH, 4A MS / CHCl3 / Ambient temperature
Multi-step reaction with 2 steps 1: 82 percent / OsO4, K2CO3, K3Fe(CN)6, dihydroquinidine-9-O-(4-chlorobenzoate) / H2O; 2-methyl-propan-2-ol / 24 h / Ambient temperature 2: 80 percent / 4-toluenesulfonic acid / CHCl3 / 3 h / Heating
  • 48
  • [ 18869-29-9 ]
  • Acetic acid (1R,2S)-2-bromo-1,2-di-p-tolyl-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-bromosuccinimide / dimethylsulfoxide 2: pyridine / 10 h / 20 °C
  • 49
  • [ 104-87-0 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / Heating 2: pyridine, POCl3 / 2 h / Heating
  • 50
  • [ 29875-07-8 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / Heating 2: pyridine, POCl3 / 2 h / Heating
  • 51
  • [ 18869-29-9 ]
  • [ 3457-48-5 ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: (E)-4,4'-dimethylstilbene With tetrabutylammonium tetrafluoroborate; dimethyl sulfoxide In dichloromethane at 0℃; Electrolysis; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at 35℃; for 1h; Inert atmosphere;
Multi-step reaction with 3 steps 1: m-chloroperbenzoic acid 2: BF3*Et2O, tris-(o,p-dibromophenyl)ammoniumyl hexachloroantimonate 3: 90 percent / tris-(o,p-dibromophenyl)ammoniumyl hexachloroantimonate / CH2Cl2 / 0.25 h / Ambient temperature; other arylacetaldehydes
  • 52
  • [ 104-81-4 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
90% With sodium 4-methylbenzenesulfinate; potassium hydroxide In dimethyl sulfoxide at 100℃; for 16h;
62% With benzyl phenyl sulfoxide; potassium <i>tert</i>-butylate at 80℃; for 12h; Green chemistry; stereoselective reaction;
62% With benzyl phenyl sulfoxide; potassium <i>tert</i>-butylate at 80℃; for 12h; Inert atmosphere;
Multi-step reaction with 3 steps 1: 1.) sodium borohydride / 1.) THF, water, 0 deg C, 2.) 25 deg C, overnight 2: 95 percent / acetonitrile / 0.5 h / -10 °C 3: 24 percent / NaNH2, NH3 (liquid) / 1 h / -78 °C
Multi-step reaction with 4 steps 2: ethanol 3: ethanol / Behandeln bei Siedetemperatur
Multi-step reaction with 4 steps 2: ethanol 3: ethanol; iodine / 20 °C
Multi-step reaction with 3 steps 2: 0.3 Torr / sowie bei 17 Torr 3: 20 Torr
12.1 mg With C6H5OS(1-)*K(1+) at 20 - 50℃; for 6h; Inert atmosphere;
Multi-step reaction with 2 steps 1: Wilkinson's catalyst; dimethyl zinc(II) / tetrahydrofuran; hexane / 96 h / 20 °C / Inert atmosphere 2: iodine / benzene-d6; water / 72 h / 180 °C / Sealed tube; Darkness

  • 53
  • [ 18869-29-9 ]
  • [ 84907-53-9 ]
YieldReaction ConditionsOperation in experiment
20% Stage #1: (E)-4,4'-dimethylstilbene With N-Bromosuccinimide In tetrachloromethane for 24h; Heating / reflux; Stage #2: With hexamethylenetetramine In chloroform for 5h; Heating / reflux; Stage #3: With hydrogenchloride; water; acetic acid more than 3 stages; 8 Example 8; Preparation of 4,4'-diformyl-stilbene; Into CCl4 solvent, 2 g(9.6 mmol) of the compound produced in Example 7 (Compound 9) and 4.27 g(24.0 mmol) of N-bromosuccinimide were added and refluxed for 24 hours. After cooled down, the reactant was suction-filtrated and the resultant solution was washed with distilled water and then was dried with anhydrous magnesium sulfate. The dried product was dissolved again in chloroform together with 4.0 g(38.4 mmol) of hexamethylenetetraamine and refluxed for 5 hours. After the reactant was cooled down, the solvent was distilled off under reduced pressure and the residue was refluxed severely in acetic acid/H2O(17 mL/17 mL) at 120° C. for 2 hours. Finally, 7 mL of HCl was added to be refluxed. After cooled down, the reactant was extracted with methylene chloride. The solution was distilled off under reduced pressure and the residue was purified through the column chromatography (silica gel, ethyl acetate/n-hexane=1:3) to be dried. Yield; 20%. 1H-NMR(CDCl3): 10.03(s, 2H), 7.92(d, 4H, Ar-H), 7.71(d, 4H, Ar-H), 7.30(s, 2H, vinyl).
Multi-step reaction with 2 steps 1: CHCl3; dibenzoyl peroxide; <i>N</i>-bromo-succinimide 2: hexamethylenetetramine; CHCl3 / Erhitzen des Reaktionsprodukts mit wss. Essigsaeure
Multi-step reaction with 2 steps 1: NBS, AIBN, (PhCO)2O2 / CHCl3; CCl4 / Heating 2: (i) hexamethylenetetramine, CHCl3, (ii) aq. AcOH
  • 54
  • [ 106-38-7 ]
  • [ 104-87-0 ]
  • [ 18107-18-1 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 4-methyl-benzaldehyde; diazomethyl-trimethyl-silane With triphenylphosphine; copper(l) chloride In tetrahydrofuran; isopropyl alcohol at 60℃; Stage #2: para-bromotoluene With triethylamine at 100℃; Further stages.;
  • 55
  • [ 18869-29-9 ]
  • trans-4,4'-dimethylstilbene oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With sodium chlorite In 2-methoxy-ethanol; water; acetonitrile at 20℃; for 24h;
  • 56
  • [ 104-87-0 ]
  • [ 18869-29-9 ]
  • [ 51490-06-3 ]
  • [ 4528-66-9 ]
YieldReaction ConditionsOperation in experiment
With H5PV2Mo10O40(1,11); hydrogen at 100℃; for 18h; Title compound not separated from byproducts.;
  • 57
  • [ 18869-29-9 ]
  • (S,S)-(-)-1,2-di(p-methylphenyl)ethane-1,2-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) In water; <i>tert</i>-butyl alcohol at 25℃; for 16h;
  • 58
  • [ 18869-29-9 ]
  • 1,2-bis(4-methylphenyl)-1,2-ethanediol [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III) In water; toluene; <i>tert</i>-butyl alcohol at 0 - 25℃;
84% Stage #1: (E)-4,4'-dimethylstilbene With water; cyclopropane-1,1-dicarbonyl peroxide In chloroform at 40℃; for 24h; Stage #2: With water; sodium hydroxide at 60℃; for 4h; optical yield given as %de; diastereoselective reaction;
  • 59
  • [ 114468-30-3 ]
  • [ 18869-29-9 ]
  • [ 1031683-85-8 ]
YieldReaction ConditionsOperation in experiment
71% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90℃; for 1h;
  • 60
  • [ 18869-29-9 ]
  • [ 1031683-80-3 ]
  • [ 1031683-87-0 ]
YieldReaction ConditionsOperation in experiment
51% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90℃; for 1h;
  • 61
  • [ 18869-29-9 ]
  • [ 1031683-79-0 ]
  • [ 1031683-86-9 ]
YieldReaction ConditionsOperation in experiment
55% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90℃; for 1h;
  • 62
  • [ 18869-29-9 ]
  • [ 1031683-82-5 ]
  • [ 1031683-90-5 ]
YieldReaction ConditionsOperation in experiment
18% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90℃; for 1h;
  • 63
  • [ 18869-29-9 ]
  • [ 1031683-91-6 ]
  • [ 1031683-84-7 ]
YieldReaction ConditionsOperation in experiment
56% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90℃; for 1h;
  • 64
  • [ 18869-29-9 ]
  • [ 31434-97-6 ]
  • [ 1031683-89-2 ]
YieldReaction ConditionsOperation in experiment
23% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90℃; for 1h;
  • 65
  • [ 18869-29-9 ]
  • [ 148172-13-8 ]
  • [ 1031683-83-6 ]
YieldReaction ConditionsOperation in experiment
60% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90℃; for 1h;
  • 66
  • [ 18869-29-9 ]
  • [ 117241-26-6 ]
  • [ 1031683-84-7 ]
YieldReaction ConditionsOperation in experiment
66% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90℃; for 1h;
  • 67
  • [ 18869-29-9 ]
  • [ 117241-34-6 ]
  • [ 1031683-88-1 ]
YieldReaction ConditionsOperation in experiment
65% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90℃; for 1h;
  • 68
  • [ 18869-29-9 ]
  • 1-methoxy-1-(4-fluorophenylthio)nonane [ No CAS ]
  • [ 1103584-23-1 ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: 1-methoxy-1-(4-fluorophenylthio)nonane With C18H12F3S3(1+)*C24BF20(1-) In dichloromethane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: (E)-4,4'-dimethylstilbene In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
  • 69
  • [ 622-97-9 ]
  • [ 106-43-4 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
99% With tetrakis[μ-1-[(3-methoxyphenyl)methyl]-2-phenyl-3-[2-oxo-2-[(2-phenolato-kO)aminokN]ethyl]-1H-imidazoliumato-kC4]tetrapalladium; tetrabutylammomium bromide; sodium acetate at 140℃; for 12h;
80% With lithium hydroxide monohydrate; C21H18N4O2Pd; tetrabutylammomium bromide In N,N-dimethyl acetamide at 160℃; for 44h;
56% With tetrabutylammomium bromide; sodium acetate; C84H60N12O8Pd4 at 140℃; for 12h; Inert atmosphere; Schlenk technique;
55% With potassium phosphate; C24H22ClN3OPdSe; tetrabutylammomium bromide In water at 110℃; for 12h;
36% With lithium hydroxide monohydrate; C18H21N3O2Pd; tetrabutylammomium bromide In N,N-dimethyl-formamide at 160℃; for 24h; Typical procedure for Heck reaction of aryl Chlorides General procedure: The 100 mL RB-flask was charged with aryl chlorides (1.0 mmol), alkenes (2.0 mmol), LiOH*H2O (2.0 mmol), TBAB (0.5 mmol) and the catalyst (1 mol%) in N,N-dimethylformamide (2.0 mL). The reaction mixture was heated at 160 oC for 24 h and the progress of reaction was monitored by TLC. At the end of the reaction, the reaction mixture was cooled to room temperature and was diluted with EtOAc (20 mL), washed with 1N aq. HCl and water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the Heck product in high purity.
26% With lithium hydrochloride monohydrate; C30H20F12N6O2Pd In N,N-dimethyl acetamide at 160℃; for 20h;

  • 70
  • [ 18869-29-9 ]
  • C13H18N2O4S [ No CAS ]
  • [ 1182735-00-7 ]
  • C28H32N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With potassium hydrogencarbonate In chloroform at 20℃; optical yield given as %de; diastereoselective reaction;
  • 71
  • [ 624-31-7 ]
  • [ 1177254-37-3 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
78% With bis(η3-allyl-μ-chloropalladium(II)); tetrabutyl ammonium fluoride In tetrahydrofuran at 65℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 72
  • [ 104-87-0 ]
  • [ 18869-29-9 ]
  • 1,2-di-p-tolylethane-1,2-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 85% 2: 6 %Spectr. With chloro-trimethyl-silane; titanium(IV)isopropoxide; magnesium; triethylamine In tetrahydrofuran at 40℃; for 48h; optical yield given as %de;
  • 73
  • [ 18869-29-9 ]
  • BF4(1-)*C18H12F3S3(1+) [ No CAS ]
  • [ 1224955-62-7 ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: (E)-4,4'-dimethylstilbene; BF4(1-)*C18H12F3S3(1+) In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene In dichloromethane at -78℃; for 0.5h; Inert atmosphere; stereoselective reaction;
  • 74
  • 2Br(1-)*C30H34NP(2+) [ No CAS ]
  • [ 104-87-0 ]
  • [ 18869-29-9 ]
  • [ 2510-76-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2Br(1-)*C30H34NP(2+) With sodium hydride In 1,2-dimethoxyethane at 0℃; for 1h; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In 1,2-dimethoxyethane at 60℃; for 10h; Inert atmosphere; optical yield given as %de; diastereoselective reaction; 4.3. Typical procedure for the Wittig reaction with ion-supported Ph3P A2 General procedure: To a solution of 4-methylbenzyl bromide (1.67 g, 9.0 mmol) in 1,2-dichloroethane (30 mL) was added 4-(diphenylphosphino)benzyltrimethylammonium bromide A (1.88 g, 4.5 mmol). The obtained mixture was stirred for 2 h at 60 °C. After the reaction, ether was added and the mixture was stirred for 10 min at room temperature. Then, the mixture was filtered and washed with ether. Removal of the solvent from the filtrate gave phosphonium salt A2 in 95% yield. The obtained phosphonium salt A2 (360 mg, 0.6 mmol) was dried by a vacuum pump for 2 h at 70 °C. To the flask containing phosphonium salt A2 were added NaH (44 mg, 1.0 mmol) and 1,2-dimethoxyethane (2 mL). The obtained mixture was stirred for 1 h at 0 °C under an argon atmosphere. After the reaction, p-chlorobenzaldehyde (70 mg, 0.5 mmol) and 1,2-dimethoxyethane (2 mL) were added and the obtained mixture was stirred for 8 h at 60 °C under an argon atmosphere. After the reaction, acetic acid (5 mL) was added and the obtained mixture was filtered and washed with acetic acid. Removal of the solvent from the filtrate gave 1-(4'-chlorophenyl)-2-(4-methylphenyl)ethene (E/Z=75:25) in the crude state. The purity was estimated by 1H NMR and was 95%. Pure 1-(4'-chlorophenyl)-2-(4-methylphenyl)ethene was obtained in 95% yield by short flash column chromatography on silica gel (hexane/CHCl3=1:4). The co-product, 4-(diphenylphosphono)benzyltrimethylammonium bromide, was recovered by the above filtration in 97% yield.
  • 75
  • 2Br(1-)*C32H36NP(2+) [ No CAS ]
  • [ 104-87-0 ]
  • [ 18869-29-9 ]
  • [ 2510-76-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2Br(1-)*C32H36NP(2+) With sodium hydride In toluene at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In toluene at 0 - 60℃; for 9h; Inert atmosphere; optical yield given as %de; diastereoselective reaction; 4.6. Typical procedure for the Wittig reaction with ion-supported Ph3P B2 General procedure: Phosphonium salt B2 (939 mg, 1.5 mmol) was dried by a vacuum pump for 2 h at 70 °C. To the flask containing phosphonium salt B2 were added NaH (80 mg, 2.0 mmol) and toluene (5 mL). The obtained mixture was stirred for 1 h at 0 °C initially to room temperature under an argon atmosphere. Then, 4-chlorobenzaldehyde (141 mg, 1.0 mmol) was added to the solution at 0 °C and the obtained mixture was stirred for 9 h at 0 °C initially to 60 °C. After the reaction, ether (10 mL) was added and the obtained mixture was stirred for 10 min at room temperature. Then, the mixture was filtered and washed with ether. Removal of the solvent from the filtrate gave 1-(4'-chlorophenyl)-2-(4-methylphenyl)ethene (E:Z=75:25) in 90% purity, which was estimated by 1H NMR. Pure 1-(4'-chlorophenyl)-2-(4-methylphenyl)ethene was obtained in 91% yield by short flash column chromatography on silica gel (CHCl3/hexane=10:1). The co-product, N-methyl-N-[4-(diphenylphosphono)benzyl]pyrrolidinium bromide, was recovered by the above filtration in 98% yield.
  • 76
  • [ 1334478-52-2 ]
  • [ 18869-29-9 ]
  • [ 142087-16-9 ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydride In dimethyl sulfoxide at 20℃; stereoselective reaction;
  • 77
  • [ 622-97-9 ]
  • [ 1576-35-8 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
88% With oxygen; palladium diacetate In nitromethane; dimethyl sulfoxide at 70℃; for 5h; stereoselective reaction;
  • 78
  • [ 18869-29-9 ]
  • [ 67-68-5 ]
  • 2BF4(1-)*C20H28O2S2(2+) [ No CAS ]
  • 2BF4(1-)*C20H28O2S2(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; tetrabutylammonium tetrafluoroborate In dichloromethane at 0℃; Inert atmosphere; Electrolysis;
  • 79
  • [ 870004-04-9 ]
  • [ 622-97-9 ]
  • [ 18869-29-9 ]
  • [ 1422172-84-6 ]
YieldReaction ConditionsOperation in experiment
1: 45% 2: 508 mg With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 43℃; for 22h; Inert atmosphere; General procedure for the CM reaction of 4: General procedure: (E)-4,4,5,5-Tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane 7a. Boronate 4a (113 mg, 0.49 mmol), styrene 5a (281 µL, 0.91 gmL-1, 2.45 mmol), Grubbs’ catalyst 6b (12 mg, 0.015 mmol), and CH2Cl2 (5 mL) were mixed in a round-bottomed flask and stirred under reflux (~ 45 °C) and nitrogen atmosphere for 6 hours. The mixture was cooled to rt, the volatiles were removed under reduced pressure and the crude product purified by flash chromatography on silica gel, hexane/CH2Cl2 6:4, to give 97 mg of the pure expected product as a white solid in 65% yield, (E)-isomer only.
  • 80
  • [ 18869-29-9 ]
  • [ 75-25-2 ]
  • 4,4'-(3,3-dibromocyclopropane-1,2-diyl)bis(methylbenzene) [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 20℃; for 6h; Inert atmosphere; 10.3 General dibromocyclopropanation procedure for synthesis of 4 General procedure: To a stirred solution of stilbene 9/10b (2.40mmol) in bromoform (20.0mL, 0.12M) was added triethylbenzylammonium chloride (109mg, 0.480mmol). An equal volume of a saturated aqueous solution of concentrated sodium hydroxide was added dropwise. The reaction was stirred at room temperature until full reaction conversion was achieved (as monitored by 1H NMR analysis). The reaction mixture was quenched with water (150.0mL) and stirred at room temperature for 15min. The reaction mixture was washed with water (5×100mL) and dichloromethane (3×75mL). The organic phase was evaporated under high vacuum to remove bromoform. Purification using flash column chromatography (hexanes) afforded cyclopropane 4.
  • 81
  • [ 540-49-8 ]
  • [ 5720-05-8 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
78% With potassium phosphate; [Rh(OH)(cod)]2; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 100℃; for 3h; Schlenk technique; Inert atmosphere;
  • 82
  • [ 622-97-9 ]
  • [ 4294-57-9 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: para-methylphenylmagnesium bromide With diethylaluminium chloride In tetrahydrofuran; hexane at 0 - 20℃; for 3h; Schlenk technique; Stage #2: 1-ethenyl-4-methylbenzene With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,4-dimethylpentan-3-one at 60℃; for 3h;
  • 83
  • [ 925-90-6 ]
  • [ 4294-57-9 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
56% With aluminum (III) chloride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,4-dimethylpentan-3-one In tetrahydrofuran; hexane at 0 - 60℃; for 24h; Inert atmosphere; Schlenk technique;
  • 84
  • [ 622-97-9 ]
  • [ 110979-21-0 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
99% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,4-dimethylpentan-3-one In tetrahydrofuran; hexane at 60℃; Schlenk technique;
  • 85
  • [ 18869-29-9 ]
  • (1R,2S)-1,2-Di-p-tolyl-ethane-1,2-diol [ No CAS ]
  • 1,2-bis(4-methylphenyl)-1,2-ethanediol [ No CAS ]
YieldReaction ConditionsOperation in experiment
60 % de Stage #1: (E)-4,4'-dimethylstilbene With cyclopropane-1,1-dicarbonyl peroxide; acetic acid In dichloromethane at 40℃; for 24h; Inert atmosphere; Sealed tube; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 60℃; for 18h; Overall yield = 91 %; Overall yield = 221 mg; diastereoselective reaction;
  • 86
  • [ 2789-88-0 ]
  • [ 18869-29-9 ]
  • [ 2510-76-1 ]
YieldReaction ConditionsOperation in experiment
With [{CyPN(H)P}Co(CH2SiMe3)]-BArF4; hydrogen In tetrahydrofuran at 25℃;
84 % de With formic acid; potassium carbonate In acetonitrile at 80℃; for 2.5h; Overall yield = 86 percentSpectr.;
  • 87
  • [ 41468-10-4 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
65% With titanium tetrachloride; zinc In 1,4-dioxane at 80℃; for 5h; Inert atmosphere; Reflux; 3.3. General Procedure for the Preparation of (E)-1,2-Diarylethenes 3 General procedure: TiCl4 (22.5 g, 118.62 mmol) was slowly added to 1,4-dioxane (250 mL) at -5 to 5°C under N2. To the resultingyellow solution, Zn dust (15.5 g, 237.08 mmol) was added.The resulting mixture was refluxed for 1.5 h. After coolingto rt, the bisulfite adduct 2 (30.00 mmol) and 1,4-dioxane(100 mL) were added, and the mixture was refluxed for addiadditional5 h. After cooling to rt, the solvent was removed underreduced pressure. The remaining dark tan solid was treatedwith diluted HCl solution (10%, 200 mL) and stirred for 2 h.The reaction mixture was extracted with CH2Cl2 (2 × 150 mL).The combined extract was washed with water (2 × 50 mL)and dried over Na2SO4. The solvent was evaporated underreduced pressure, and the residue was subjected to silica gelcolumn chromatography (CH2Cl2) to obtain the products 3 in65-84% yields.
  • 88
  • C15H14O [ No CAS ]
  • [ 4294-57-9 ]
  • [ 18869-29-9 ]
YieldReaction ConditionsOperation in experiment
98% With iron(II) chloride In tetrahydrofuran; 1,2-dimethoxyethane at -78 - 20℃; for 48h; Sealed tube; Glovebox; Inert atmosphere; chemoselective reaction;
Same Skeleton Products
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