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[ CAS No. 50325-49-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Quality Control of [ 50325-49-0 ]

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SDS Specification
Alternatived Products of [ 50325-49-0 ]

Product Details of [ 50325-49-0 ]

CAS No. :50325-49-0 MDL No. :MFCD08704374
Formula : C9H11N Boiling Point : -
Linear Structure Formula :- InChI Key :WAVDSLLYAQBITE-UHFFFAOYSA-N
M.W : 133.19 Pubchem ID :11073466
Synonyms :

Calculated chemistry of [ 50325-49-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.21
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 1.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 0.93 mg/ml ; 0.00698 mol/l
Class : Soluble
Log S (Ali) : -2.04
Solubility : 1.22 mg/ml ; 0.00916 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.85
Solubility : 0.186 mg/ml ; 0.0014 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.14

Safety of [ 50325-49-0 ]

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

Application In Synthesis of [ 50325-49-0 ]

* 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 [ 50325-49-0 ]

[ 50325-49-0 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 62940-38-9 ]
  • [ 50325-49-0 ]
  • (4-Vinyl-benzyl)-[1-(4''-[(Z)-4-vinyl-benzylimino]-methyl}-[1,1';4',1'']terphenyl-4-yl)-meth-(Z)-ylidene]-amine [ No CAS ]
Reference： [1]Chemische Berichte,1979,vol. 112,p. 2854 - 2865
  • 2
  • [ 343767-89-5 ]
  • [ 50325-49-0 ]
  • [1-(4'-Biphenyl-4-ylmethyl-biphenyl-4-yl)-meth-(Z)-ylidene]-(4-vinyl-benzyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 3
  • [ 343621-44-3 ]
  • [ 50325-49-0 ]
  • [1-(2,2'-Dinitro-4'-[(Z)-4-vinyl-benzylimino]-methyl}-biphenyl-4-yl)-meth-(Z)-ylidene]-(4-vinyl-benzyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 4
  • [ 111759-28-5 ]
  • [ 50325-49-0 ]
  • (4-Vinyl-benzyl)-[1-[4'-(4'-[(E)-4-vinyl-benzylimino]-methyl}-biphenyl-4-ylmethyl)-biphenyl-4-yl]-meth-(E)-ylidene]-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 5
  • [ 343796-12-3 ]
  • [ 50325-49-0 ]
  • [1-(2,2',2''-Trinitro-4''-[(Z)-4-vinyl-benzylimino]-methyl}-[1,1';4',1'']terphenyl-4-yl)-meth-(Z)-ylidene]-(4-vinyl-benzyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 6
  • [ 66-98-8 ]
  • [ 50325-49-0 ]
  • (4-Vinyl-benzyl)-[1-(4'-[(E)-4-vinyl-benzylimino]-methyl}-biphenyl-4-yl)-meth-(Z)-ylidene]-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 7
  • [ 67-37-8 ]
  • [ 50325-49-0 ]
  • (4-Vinyl-benzyl)-[1-[4-(4-[(E)-4-vinyl-benzylimino]-methyl}-benzyl)-phenyl]-meth-(E)-ylidene]-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 8
  • [ 623-27-8 ]
  • [ 50325-49-0 ]
  • [ 100207-96-3 ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 9
  • [ 100-52-7 ]
  • [ 50325-49-0 ]
  • [ 111740-43-3 ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 10
  • [ 50325-49-0 ]
  • [ 3218-36-8 ]
  • [1-Biphenyl-4-yl-meth-(Z)-ylidene]-(4-vinyl-benzyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 11
  • [ 50325-49-0 ]
  • [ 17800-49-6 ]
  • [1-[1,1';4',1'']Terphenyl-4-yl-meth-(Z)-ylidene]-(4-vinyl-benzyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform
Reference： [1]Wulff,G. et al. [Chemische Berichte, 1979, vol. 112, p. 2854 - 2865]
  • 12
  • [ 3661-73-2 ]
  • [ 50325-49-0 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride In diethyl ether for 48h; Heating; Yield given;
Reference： [1]Berry, Madeleine; Csorba, Janice; Champaneria, Ramesh K.; Howell, James A. S. [Zeitschrift fur Naturforschung, B: Chemical Sciences, 1988, vol. 43, # 7, p. 862 - 872]
  • 13
  • [ 50325-49-0 ]
  • [ 109-94-4 ]
  • (p-vinyl)benzylformamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% 1.) reflux, 2 h, 2.) r.t., overnight;
Reference： [1]Berry, Madeleine; Csorba, Janice; Champaneria, Ramesh K.; Howell, James A. S. [Zeitschrift fur Naturforschung, B: Chemical Sciences, 1988, vol. 43, # 7, p. 862 - 872]
  • 14
  • [ 1592-20-7 ]
  • [ 50325-49-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium hydride; 1,1,3,3-tetramethyldisilazane 1.) THF, 1 h, 0 deg C; 1 h, r.t.; Yield given. Multistep reaction;
With ammonium acetate In methanol at 60℃; for 5h;
Multi-step reaction with 2 steps 1: 81 percent / dimethylformamide / 17 h / 55 °C 2: 90 percent / hydrazine hydrate / ethanol / 2.5 h / Heating
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 80 °C 2: triphenylphosphine / tetrahydrofuran; water / 2.5 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 17 h / 20 °C 2: hydrazine hydrate / ethanol / 3 h / 80 °C / Inert atmosphere

Reference： [1]Itsuno; Koizumi; Okumura; Ito [Synthesis, 1995, # 2, p. 150 - 152]
[2]Sundararajan; Prabagaran [Organic Letters, 2001, vol. 3, # 3, p. 389 - 392]
[3]Bertini, Vincenzo; Alfei, Silvana; Pocci, Marco; Lucchesini, Francesco; Picci, Nevio; Iemma, Francesca [Tetrahedron, 2004, vol. 60, # 50, p. 11407 - 11414]
[4]Hayama, Riho; Koyama, Tetsuo; Matsushita, Takahiko; Hatano, Ken; Matsuoka, Koji [Molecules, 2018, vol. 23, # 11]
[5]Bian, Guomin; Huang, Xianpei; Liu, Fuyao; Qi, Yonglin; Sun, Zunming; Yang, Xinlin; Yang, Xinyue; Zhang, Mengmeng; Zhang, Wangqing [New Journal of Chemistry, 2020, vol. 44, # 22, p. 9546 - 9556]
  • 15
  • [ 201230-82-2 ]
  • [ 50325-49-0 ]
  • N,N'-bis(4-ethenylbenzyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With 2C7H9N4*Au(1+)*Cu(1+)*2I(1-) In toluene at 60℃; Autoclave;
69% With tungsten hexacarbonyl; iodine; potassium carbonate In dichloromethane at 20℃; for 24h;
Reference： [1]Cao, Yanwei; Yang, Jian-Gong; Deng, Yi; Wang, Shengchun; Liu, Qi; Shen, Chaoren; Lu, Wei; Che, Chi-Ming; Chen, Yong; He, Lin [Angewandte Chemie - International Edition, 2020, vol. 59, # 5, p. 2080 - 2084][Angew. Chem., 2020, vol. 132, # 5, p. 2096 - 2100,5]
[2]McCusker, Jennifer E.; Main, A. Denise; Johnson, Kirsten S.; Grasso, Cara A.; McElwee-White, Lisa [Journal of Organic Chemistry, 2000, vol. 65, # 17, p. 5216 - 5222]
  • 16
  • [ 20780-54-5 ]
  • [ 50325-49-0 ]
  • 3-aza-3-(p-vinylbenzyl)-1,5-diphenyl-1,5-dihydroxypentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% In methanol at 0 - 60℃; for 6h;
Reference： [1]Sundararajan; Prabagaran [Organic Letters, 2001, vol. 3, # 3, p. 389 - 392]
  • 17
  • [ 4251-21-2 ]
  • [ 50325-49-0 ]
  • <i>N</i>-(4-vinyl-benzyl)-3-{4-[2-(4-vinyl-benzylcarbamoyl)-ethyl]-phenyl}-propionamide [ No CAS ]
Reference： [1]Tetrahedron,2001,vol. 57,p. 1551 - 1558
  • 18
  • [ 50325-49-0 ]
  • [ 501-52-0 ]
  • 3-phenyl-N-(4-vinylbenzyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20℃; for 0.5h;
Reference： [1]Kunishima, Munetaka; Kawachi, Chiho; Hioki, Kazuhito; Terao, Keiji; Tani, Shohei [Tetrahedron, 2001, vol. 57, # 8, p. 1551 - 1558]
  • 19
  • [ 50325-49-0 ]
  • [ 359686-17-2 ]
  • [ 359686-23-0 ]
YieldReaction ConditionsOperation in experiment
73% With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 1h;
Reference： [1]Akai, Shoji; Kajihara, Yasuhiro; Nagashima, Yasuhiko; Kamei, Masugu; Arai, Junko; Bito, Masami; Sato, Ken-Ichi [Journal of Carbohydrate Chemistry, 2001, vol. 20, # 2, p. 121 - 143]
  • 20
  • [ 50325-49-0 ]
  • [ 359687-10-8 ]
  • [ 359687-29-9 ]
YieldReaction ConditionsOperation in experiment
76% With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 1h;
Reference： [1]Akai, Shoji; Kajihara, Yasuhiro; Nagashima, Yasuhiko; Kamei, Masugu; Arai, Junko; Bito, Masami; Sato, Ken-Ichi [Journal of Carbohydrate Chemistry, 2001, vol. 20, # 2, p. 121 - 143]
  • 21
  • [ 50325-49-0 ]
  • [ 359687-15-3 ]
  • [ 359687-32-4 ]
YieldReaction ConditionsOperation in experiment
61% With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.333333h;
Reference： [1]Akai, Shoji; Kajihara, Yasuhiro; Nagashima, Yasuhiko; Kamei, Masugu; Arai, Junko; Bito, Masami; Sato, Ken-Ichi [Journal of Carbohydrate Chemistry, 2001, vol. 20, # 2, p. 121 - 143]
  • 22
  • [ 50325-49-0 ]
  • [ 359687-00-6 ]
  • p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2,4-di-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 1h;
Reference： [1]Akai, Shoji; Kajihara, Yasuhiro; Nagashima, Yasuhiko; Kamei, Masugu; Arai, Junko; Bito, Masami; Sato, Ken-Ichi [Journal of Carbohydrate Chemistry, 2001, vol. 20, # 2, p. 121 - 143]
  • 23
  • [ 50325-49-0 ]
  • [ 359687-05-1 ]
  • [ 359687-25-5 ]
YieldReaction ConditionsOperation in experiment
81% With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 1h;
Reference： [1]Akai, Shoji; Kajihara, Yasuhiro; Nagashima, Yasuhiko; Kamei, Masugu; Arai, Junko; Bito, Masami; Sato, Ken-Ichi [Journal of Carbohydrate Chemistry, 2001, vol. 20, # 2, p. 121 - 143]
  • 24
  • [ 100-42-5 ]
  • [ 50325-49-0 ]
  • copolymer, Mw(D): 19000, Mw/Mn = 1.4; monomer(s): styrene; 4-vinylbenzyl amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 40h;
Reference： [1]Malagu, Karine; Guérin, Philippe; Guillemin, Jean-Claude [Synlett, 2002, # 2, p. 316 - 318]
  • 25
  • [ 100-42-5 ]
  • [ 50325-49-0 ]
  • styrene/aminomethylstyrene-copolymer [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In cyclohexane at 50℃; for 90h;
Reference： [1]Tsogoeva, Svetlana B.; Wöltinger, Jens; Jost, Carsten; Reichert, Dietmar; Kühnle, Adolf; Krimmer, Hans-Peter; Drauz, Karlheinz [Synlett, 2002, # 5, p. 707 - 710]
  • 26
  • [ 50325-49-0 ]
  • styrene/aminomethylstyrene/L-leucine-copolymer [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In cyclohexane at 50℃; for 90h;
Reference： [1]Tsogoeva, Svetlana B.; Wöltinger, Jens; Jost, Carsten; Reichert, Dietmar; Kühnle, Adolf; Krimmer, Hans-Peter; Drauz, Karlheinz [Synlett, 2002, # 5, p. 707 - 710]
  • 27
  • [ 63413-74-1 ]
  • [ 50325-49-0 ]
YieldReaction ConditionsOperation in experiment
97% With hydrazine hydrate
90% With hydrazine hydrate In ethanol for 2.5h; Heating;
90% With hydrazine hydrate In ethanol for 3.5h; Inert atmosphere; Reflux;
89% With methylhydrazine In ethanol at 20℃;
62% With 4-tert-Butylcatechol; hydrazine hydrate In ethanol for 4h; Reflux; 2.3. Synthesis of 4-vinylbenzyl amine The 4-vinylbenzyl phthalimide (5.1 g, 19 mmol), 80% hydrazine monohydrate (1.6 g, 32 mmol), and p-tert-butylcatechol (50 mg, 0.30 mmol) were dissolved in ethanol (50 mL). After reflux for 4 h, the solution was adjusted to pH 1-2 by adding 1 M hydrochloric acid, filtrated, and then adjusted to pH 10-11 with 1 M sodium hydroxide aqueous solution. The resultant was extracted to diethyl ether for several times. The organic phase was washed with water, dried over magnesium sulfate, filtrated, and evaporated. The crude oil was further purified by vacuum distillation under calcium oxide to give a clear oil (yield: 1.6 g, 62%). 1H NMR (CDCl3, 400 MHz), d (p.p.m.): 7.4-7.2 (m, 4H, aromatic H), 6.7 (dd, 1H, -CH2]CH-), 5.8-5.2 (d, 2H, -CH2]CH-), 3.8 (s, 2H, -CH2-N-).
42% Stage #1: 2-(4-ethenylbenzyl)-1H-isoindole-1,3(2H)-dione With 4-tert-Butylcatechol; hydrazine In ethanol for 3h; Reflux; Stage #2: With hydrogenchloride In ethanol; water Stage #3: With sodium hydroxide In ethanol; water
With hydrazine hydrate In ethanol for 4h; Heating;
With hydrazine In ethanol for 2.16667h; Heating / reflux; 2 Reaction Scheme 2: Synthesis of Vinylbenzylamine One kg of vinylbenzyl phthalimide was dissolved in 2.7 L of ethanol in an separable flask of appropriate volume followed by heating and refluxing in the presence of flowing nitrogen. A solution of 0.36 kg of 80% hydrazine monohydrate in 545 ml of ethanol was dropped in using a dropping funnel (dropping time: about 40 minutes). The reaction was carried out for 90 minutes by heating and refluxing. Following completion of the reaction, the resulting solid was filtered out, and after dissolving by the addition of KOH solution (1 kg in 6.5 L H2O), the solution was extracted with ether (total volume: 3.6 L×3). The ether layer was further washed with 2% K2CO3 solution, and additionally washed several times with water. After drying the ether layer over Na2SO4, the ether was distilled off, and the residue was distilled under reduced pressure. Boiling point: 72-73° C./3 mmHg Yield: 0.45 kg
With hydrazine hydrate In ethanol at 80℃; for 3h; Inert atmosphere;

Reference： [1]Heine, Daniel; Pietsch, Christian; Schubert, Ulrich S.; Weigand, Wolfgang [Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 10, p. 2171 - 2180]
[2]Bertini, Vincenzo; Alfei, Silvana; Pocci, Marco; Lucchesini, Francesco; Picci, Nevio; Iemma, Francesca [Tetrahedron, 2004, vol. 60, # 50, p. 11407 - 11414]
[3]Doherty, Simon; Knight, Julian G.; Backhouse, Tom; Abood, Einas; Al-shaikh, Hind; Clemmet, Ashley R.; Ellison, Jack R.; Bourne, Richard A.; Chamberlain, Thomas W.; Stones, Rebecca; Warren, Nicholas J.; Fairlamb, Ian J. S.; Lovelock, Kevin R. J. [Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3716 - 3731]
[4]Location in patent: experimental part Stals, Patrick J. M.; Phan, Trang N. T.; Gigmes, Didier; Paffen, Tim F. E.; Meijer; Palmans, Anja R. A. [Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 4, p. 780 - 791]
[5]Itoh, Tomomichi; Tamamitsu, Tetsuo; Shimomoto, Hiroaki; Ihara, Eiji [Polymer, 2015, vol. 70, p. 183 - 193]
[6]Location in patent: experimental part Audouin, Fabrice; Knoop, Ruther J. I.; Huang, Jin; Heise, Andreas [Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 20, p. 4602 - 4610]
[7]Cassano, Roberta; Trombino, Sonia; Bloise, Ermelinda; Muzzalupo, Rita; Iemma, Francesca; Chidichimo, Giuseppe; Picci, Nevio [Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 23, p. 9489 - 9495]
[8]Current Patent Assignee: UNIT4 N.V. - US2007/286847, 2007, A1 Location in patent: Page/Page column 7
[9]Bian, Guomin; Huang, Xianpei; Liu, Fuyao; Qi, Yonglin; Sun, Zunming; Yang, Xinlin; Yang, Xinyue; Zhang, Mengmeng; Zhang, Wangqing [New Journal of Chemistry, 2020, vol. 44, # 22, p. 9546 - 9556]
  • 28
  • 3-[(S)-2,6-Bis-(2,2,2-trifluoro-acetylamino)-hexanoylamino]-propionic acid [ No CAS ]
  • [ 50325-49-0 ]
  • [ 849586-31-8 ]
YieldReaction ConditionsOperation in experiment
98% With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 16h;
Reference： [1]Luebbert, Anke; Ngfuyen, Tuan Q.; Sun, Frank; Sheiko, Sergei S.; Klok, Harm-Anton [Macromolecules, 2005, vol. 38, # 6, p. 2064 - 2071]
  • 29
  • [ 126909-93-1 ]
  • [ 50325-49-0 ]
  • [ 849586-30-7 ]
YieldReaction ConditionsOperation in experiment
97% With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 16h;
Reference： [1]Luebbert, Anke; Ngfuyen, Tuan Q.; Sun, Frank; Sheiko, Sergei S.; Klok, Harm-Anton [Macromolecules, 2005, vol. 38, # 6, p. 2064 - 2071]
  • 30
  • 3-{(R)-2,6-Bis-[(R)-2,6-bis-(2,2,2-trifluoro-acetylamino)-hexanoylamino]-hexanoylamino}-propionic acid [ No CAS ]
  • [ 50325-49-0 ]
  • (R)-2,6-Bis-(2,2,2-trifluoro-acetylamino)-hexanoic acid {(R)-5-[(R)-2,6-bis-(2,2,2-trifluoro-acetylamino)-hexanoylamino]-1-[2-(4-vinyl-benzylcarbamoyl)-ethylcarbamoyl]-pentyl}-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 8h;
Reference： [1]Luebbert, Anke; Ngfuyen, Tuan Q.; Sun, Frank; Sheiko, Sergei S.; Klok, Harm-Anton [Macromolecules, 2005, vol. 38, # 6, p. 2064 - 2071]
  • 31
  • 3-[(R)-2,6-Bis-((R)-2,6-bis-benzyloxycarbonylamino-hexanoylamino)-hexanoylamino]-propionic acid [ No CAS ]
  • [ 50325-49-0 ]
  • ((R)-5-Benzyloxycarbonylamino-5-{(R)-5-((R)-2,6-bis-benzyloxycarbonylamino-hexanoylamino)-1-[2-(4-vinyl-benzylcarbamoyl)-ethylcarbamoyl]-pentylcarbamoyl}-pentyl)-carbamic acid benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 16h;
Reference： [1]Luebbert, Anke; Ngfuyen, Tuan Q.; Sun, Frank; Sheiko, Sergei S.; Klok, Harm-Anton [Macromolecules, 2005, vol. 38, # 6, p. 2064 - 2071]
  • 32
  • C106H134N14O24 [ No CAS ]
  • [ 50325-49-0 ]
  • C115H143N15O23 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 16h;
Reference： [1]Luebbert, Anke; Ngfuyen, Tuan Q.; Sun, Frank; Sheiko, Sergei S.; Klok, Harm-Anton [Macromolecules, 2005, vol. 38, # 6, p. 2064 - 2071]
  • 33
  • C109H139N15O25 [ No CAS ]
  • [ 50325-49-0 ]
  • C118H148N16O24 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 16h;
Reference： [1]Luebbert, Anke; Ngfuyen, Tuan Q.; Sun, Frank; Sheiko, Sergei S.; Klok, Harm-Anton [Macromolecules, 2005, vol. 38, # 6, p. 2064 - 2071]
  • 34
  • [ 50325-49-0 ]
  • lactobionolactone [ No CAS ]
  • [ 96886-53-2 ]
YieldReaction ConditionsOperation in experiment
In methanol at 70℃; for 2h; 4 Reaction Scheme 4: Synthesis of VLA After dissolving 1 kg of lactose lactone in 5.4 L of methanol in a round-bottom recovery flask of appropriate volume at 70° C., 0.4 kg of vinylbenzylamine was added and allowed to react for 120 minutes at 70° C. Following completion of the reaction, 21.7 L of acetone was added to precipitate the target substance. After allowing this to stand undisturbed for several hours at 4° C., the precipitate was filtered out and recrystallized from methanol. Yield: 1.1 kg
Reference： [1]Current Patent Assignee: UNIT4 N.V. - US2007/286847, 2007, A1 Location in patent: Page/Page column 8
  • 35
  • C10H16N2O6 [ No CAS ]
  • [ 50325-49-0 ]
  • C28H34N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20 - 50℃; for 1.08333h; 10 4-Vinylbenzyl amine (4.41 g, prepared according to the method described by V. Bertini et al. in Tetrahedron, 60, 11407 (2004)) was added dropwise to a stirring solution of the product of Preparative Example 6 (5.00 g) in ethanol (40 mL). After the mixture was stirred for 5 minutes at room temperature, it was stirred and heated to 500C for 1 hour and it thickened into a gel. The gel was mixed with hot isopropanol (250 mL), filtered, and dried under vacuum to afford 4.40 g of product. This compound formed a gel according to the gelation test at approximately one weight percent organogelator.
Reference： [1]Current Patent Assignee: 3M CO - WO2008/33911, 2008, A2 Location in patent: Page/Page column 78-79
  • 36
  • [ 2004-06-0 ]
  • [ 50325-49-0 ]
  • N6-(4-vinylbenzyl)adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine In propan-1-ol at 100℃; for 11h;
Reference： [1]Kim, Young Ah; Sharon, Ashoke; Chu, Chung K.; Rais, Reem H.; Al Safarjalani, Omar N.; Naguib, Fardos N.M.; el Kouni, Mahmoud H. [Biochemical Pharmacology, 2007, vol. 73, # 10, p. 1558 - 1572]
  • 37
  • [ 50325-49-0 ]
  • [ 359687-43-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / WSC / CH2Cl2 / 1 h / 0 °C 2: 279 mg / NaOMe / methanol / 2 h / pH 10
Reference： [1]Akai, Shoji; Kajihara, Yasuhiro; Nagashima, Yasuhiko; Kamei, Masugu; Arai, Junko; Bito, Masami; Sato, Ken-Ichi [Journal of Carbohydrate Chemistry, 2001, vol. 20, # 2, p. 121 - 143]
  • 38
  • [ 50325-49-0 ]
  • [ 359687-35-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 67 percent / WSC / CH2Cl2 / 1 h / 0 °C 2: 94 percent / NaOMe / methanol / 2 h / pH 10
Reference： [1]Akai, Shoji; Kajihara, Yasuhiro; Nagashima, Yasuhiko; Kamei, Masugu; Arai, Junko; Bito, Masami; Sato, Ken-Ichi [Journal of Carbohydrate Chemistry, 2001, vol. 20, # 2, p. 121 - 143]
  • 39
  • [ 50325-49-0 ]
  • [ 359686-30-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 73 percent / WSC / CH2Cl2 / 1 h / 0 °C 2: 97 percent / NaOMe / methanol / 2 h / pH 10
Reference： [1]Akai, Shoji; Kajihara, Yasuhiro; Nagashima, Yasuhiko; Kamei, Masugu; Arai, Junko; Bito, Masami; Sato, Ken-Ichi [Journal of Carbohydrate Chemistry, 2001, vol. 20, # 2, p. 121 - 143]
  • 40
  • [ 50325-49-0 ]
  • [ 359687-39-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / WSC / CH2Cl2 / 1 h / 0 °C 2: 333 mg / NaOMe / methanol / 2 h / pH 10
Reference： [1]Akai, Shoji; Kajihara, Yasuhiro; Nagashima, Yasuhiko; Kamei, Masugu; Arai, Junko; Bito, Masami; Sato, Ken-Ichi [Journal of Carbohydrate Chemistry, 2001, vol. 20, # 2, p. 121 - 143]
  • 41
  • [ 50325-49-0 ]
  • 4-(4-Carboxybutyramido)methyl)styrene [ No CAS ]
  • [ 139441-07-9 ]
YieldReaction ConditionsOperation in experiment
7 Preparation of 4-(4-Carboxybutyramido)methyl)styrene EXAMPLE 7 Preparation of 4-(4-Carboxybutyramido)methyl)styrene This compound was prepared by procedures analogous to those of Example 1 except substituting p-vinylbenzylamine for vinylbenzyl alcohol used in Example 1: m.p. of 132°-133° C. Yield of 80%. Analysis calculated for C14 H17 NO3: C, 68.0, H, 6.93, N, 5.66. Found: C, 67.67, H, 6.85, N, 5.57. 1H NMR (DMSOd6) δ 1.7 (m, 2H, C--CH2 --C), 2.2 (m, 4H, STR15 4.25 (d, 2H, CH2 --N), 5.15+5.7 (AB quartet, 2H, CH2 =), 6.7 (m, 1H CH=), 7.3 (AB quartet, 4H, ArH's), 83. (broad t, 1H, NH).
Reference： [1]Current Patent Assignee: QUIDELORTHO CORPORATION; Ortho-Clinical Diagnostics (in: QuidelOrtho) - US5210289, 1993, A
  • 42
  • [ 541-41-3 ]
  • [ 50325-49-0 ]
  • [ 132852-90-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; carbon disulfide; triethylamine; hydroquinone In chloroform; water 2 [Preparation of p'-carboxybenzaldehyde 2-methyl-4-P-vinylbenzylthiosemicarbazone] Example 2 [Preparation of p'-carboxybenzaldehyde 2-methyl-4-P-vinylbenzylthiosemicarbazone] In 100 ml of chloroform was dissolved 50.00 g of p-vinylbenzylamine and 500 mg of hydroquinone, and 18.7 ml of carbon disulfide and 40 ml of triethylamine were slowly added dropwise thereto. Then, the reaction was carried out at room temperature for 2 hours. After that, 40 ml of triethylamine and 28.9 ml of ethyl chloroformate were added again thereto in order, and the reaction was carried out for 1 hour. After the reation, 100 ml of water and 100 ml of 10 % hydrochloric acid were added thereto to separate the organic phase. Then, the organic phase was washed with water, and dried with Glauber's salt. The organic phase from which the Glauber's salt was filtered away was concentrated to give 42.00 g of a crude product.
Reference： [1]Current Patent Assignee: FUJII SHINICHIRO HM; NIPPON STEEL CORPORATION; FUJII KEIKO HF; EARTH CORPORATION; TAKADA KAORUKO HF - EP423373, 1991, A1
  • 43
  • [ 12093-10-6 ]
  • [ 50325-49-0 ]
  • [ 945485-49-4 ]
YieldReaction ConditionsOperation in experiment
59% In toluene soln. of Fe-complex and ligand in toluene heated at 605°C for 28 h in presence of molecular sieves; molecular sieves removed, evapd. to dryness, ppt. washed with hexane; elem. anal.;
Reference： [1]Suzaki, Yuji; Osakada, Kohtaro [Dalton Transactions, 2007, # 23, p. 2376 - 2383]
  • 44
  • [ 50325-49-0 ]
  • [ 156028-26-1 ]
  • C42H22Cl4N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In propionic acid at 150℃; for 16h;
Reference： [1]Woell, Dominik; Uji-i, Hiroshi; Schnitzler, Tobias; Hotta, Jun-Ichi; Dedecker, Peter; Herrmann, Andreas; De Schryver, Frans C.; Muellen, Klaus; Hofkens, Johan [Angewandte Chemie - International Edition, 2008, vol. 47, # 4, p. 783 - 787]
  • 45
  • [ 50325-49-0 ]
  • [ 98-59-9 ]
  • [ 1217489-64-9 ]
YieldReaction ConditionsOperation in experiment
1.14 g With triethylamine In dichloromethane at 20℃;
Reference： [1]Williamson, Kevin S.; Yoon, Tehshik P. [Journal of the American Chemical Society, 2010, vol. 132, # 13, p. 4570 - 4571]
  • 46
  • [ 111965-73-2 ]
  • [ 50325-49-0 ]
YieldReaction ConditionsOperation in experiment
98% With hydrazine hydrate In ethanol at 20℃; chemoselective reaction;
95.6% With triphenylphosphine In tetrahydrofuran; water at 0 - 20℃; for 2.5h; 3.2.2. Aminomethylstyrene (AMN-Str) (3) To a solution of AZ-Str 2 (3.00 g, 18.8 mmol) in anhydr THF (10 mL) was added triphenylphosphine (TPP) (4.94 g, 20.7 mmol). H2O (30 mL) was added to the solution at 0 C and the mixturewas stirred at room temperature for 2.5 h. After the complete transformation of the AZ-Str 2 judged byTLC, the reaction mixture was diluted with CHCl3 and the mixture was shaken with 3 M aq H2SO4.The extraction was partitioned and the aqueous layer was treated with NaOH until ca. pH 12 toproduce precipitates. To the mixture was added CHCl3 and the organic solution was washed withbrine, dried over anhyd MgSO4, and evaporated to give pure AMN-Str 3 [24] (2.40 g, 95.6%) as ayellow syrup: Rf 0.37 [5:5:1 (v/v/v) CHCl3-MeOH-water]; IR (NEAT) 3281 (N-H), 3005 (C-H, Ph),1628 (N-H) cm1; 1H-NMR (500 MHz, CDCl3): δ 7.39 (d, 2 H, J = 8.10 Hz, Ph), 7.27 (d, 2 H, J = 9.15 Hz,Ph), 6.71 (dd, 1 H, Jcis = 10.90 Hz, Jtrans = 17.60 Hz, CH=), 5.73 (dd, 1 H, Jgem = 0.83 Hz, trans of CH2=)5.28 (dd, 1 H, cis of CH2=), 3.86 (s, 2 H, PhCH2), 1.56 (s, 2 H, NH2).
With triphenylphosphine In tetrahydrofuran; water at 20℃;
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 4h;

Reference： [1]Udumula, Venkatareddy; Nazari, S. Hadi; Burt, Scott R.; Alfindee, Madher N.; Michaelis, David J. [ACS Catalysis, 2016, vol. 6, # 7, p. 4423 - 4427]
[2]Hayama, Riho; Koyama, Tetsuo; Matsushita, Takahiko; Hatano, Ken; Matsuoka, Koji [Molecules, 2018, vol. 23, # 11]
[3]Williamson, Kevin S.; Yoon, Tehshik P. [Journal of the American Chemical Society, 2010, vol. 132, # 13, p. 4570 - 4571]
[4]Location in patent: scheme or table Lu, Jinni; Toy, Patrick H. [Synlett, 2011, # 20, p. 2985 - 2990]
  • 47
  • [ 24424-99-5 ]
  • [ 50325-49-0 ]
  • [ 150814-00-9 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In methanol at 20℃; for 12h; 1.1 Synthesis of tert-butyl 4-vinylbenzylcarbamate 4-vinylbenzylamine (4-VB; 200mg, 1.5 mmol), TEA (183 mg, 1.8mmol) and 10 ml of MeOH were mixed. Subsequently, Boc-anhydride (492 mg, 2.26mmol) was added dropwise. After 12 h of stirring at room temperature (RT) the product was purified by column chromatography on silica gel with a mobile phase mixture of Hex: EtOAc (14:1).
92% With triethylamine In methanol at 20℃; for 12h;
With triethylamine In methanol at 20℃;
With triethylamine In tetrahydrofuran at 0 - 25℃; for 47h; Inert atmosphere; 1-11 Production Example 1-11:
Synthesis of p-vinyl-N-t-butoxycarbonylbenzylamine 1.0 g (7.5 mmol) of p-vinylbenzylamine, 0.8 g (7.9 mmol) of triethylamine, and 10 mL of THF were placed in a 50-mL test tube purged with nitrogen, and the resulting mixture was cooled to 0° C. While stirring the mixture, 1.8 g (8.3 mmol) of di-t-butyl dicarbonate/10 mL of THF solution was added dropwise, and stirred at 25° C. for 47 hours. 0.5 g (4.8 mmol) of diethanolamine was added dropwise to the obtained mixture. After stirring for 1 hour, the obtained reaction mixture was dried under reduced pressure. 20 mL of toluene and 10 mL of water were added to the obtained concentrated residue, and liquid separation was performed. The obtained organic phase was dried under reduced pressure, thereby obtaining 1.8 g of a compound represented by the above formula (p-vinyl-N-t-butoxycarbonylbenzylamine) (yield: 103%). The 1H-NMR analysis results of the compound represented by the above formula are shown below. 1H-NMR (DMSO-d6) δ (ppm)=7.42-7.19 (m, 5H), 6.74-6.67 (m, 1H), 5.82-5.77 (m, 1H), 5.23-5.21 (m, 1H), 4.10 (d, J=5.6 Hz, 2H), 1.39 (s, 9H)
With triethylamine In tetrahydrofuran at 0 - 25℃; for 47h; Inert atmosphere; 2-11 Production Example 2-11: Synthesis of p-vinyl-N-t-butoxycarbonylbenzylamine 1.0 g (7.7 mmol) of p-vinylbenzylamine, 0.8 g (8.2 mmol) of triethylamine, and 10 mL of THF were placed in a 50-mL test tube purged with nitrogen, and the resulting mixture was cooled to 0° C. While stirring the mixture, 1.8 g (8.3 mmol) of di-t-butyl dicarbonate/10 mL of THF solution was added dropwise, and stirred at 25° C. for 47 hours. 0.5 g (4.8 mmol) of diethanolamine was added dropwise to the obtained mixture. After stirring for 1 hour, the obtained reaction mixture was dried under reduced pressure. 20 mL of toluene and 10 mL of water were added to the obtained concentrated residue, and liquid separation was performed. The obtained organic phase was dried under reduced pressure, thereby obtaining 1.8 g of a compound represented by the above formula (p-vinyl-N-t-butoxycarbonylbenzylamine) (yield: 101%). The 1H-NMR analysis results of the compound represented by the above formula are shown below. 1H-NMR (DMSO-d6) δ (ppm)=7.42-7.19 (m, 5H), 6.74-6.67 (m, 1H), 5.82-5.77 (m, 1H), 5.23-5.21 (m, 1H), 4.10 (d, J=5.6 Hz, 2H), 1.39 (s, 9H)
With triethylamine In methanol at 20℃; for 24h;

Reference： [1]Lapteva, Maria; Santer, Verena; Mondon, Karine; Patmanidis, Ilias; Chiriano, Gianpaolo; Scapozza, Leonardo; Gurny, Robert; Möller, Michael; Kalia, Yogeshvar N. [Journal of Controlled Release, 2014, vol. 196, p. 9 - 18]
[2]Bhawal, Benjamin N.; Ehinger, Christian; Morandi, Bill; Reisenbauer, Julia C. [Journal of the American Chemical Society, 2020, vol. 142, # 25, p. 10914 - 10920]
[3]Location in patent: scheme or table Gaali, Steffen; Kozany, Christian; Hoogeland, Bastiaan; Klein, Marielle; Hausch, Felix [ACS Medicinal Chemistry Letters, 2010, vol. 1, # 9, p. 536 - 539]
[4]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - US2020/24237, 2020, A1 Location in patent: Paragraph 0150-0152
[5]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US10689478, 2020, B2 Location in patent: Page/Page column 127
[6]Liu, Yanhua; Sun, Jingjing; Huang, Yixian; Chen, Yichao; Li, Jiang; Liang, Lei; Xu, Jieni; Wan, Zhuoya; Zhang, Bei; Li, Zuojun; Li, Song [Biochemical Pharmacology, 2021, vol. 189]
  • 48
  • [ 185677-00-3 ]
  • [ 18144-47-3 ]
  • [ 50325-49-0 ]
  • [ 76-05-1 ]
  • tert-butyl 4-(4-(2,2,2-trifluoroethoxy)-6-(4-vinylbenzylamino)-1,3,5-triazin-2-ylamino)benzoate trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35.2% Stage #1: 2,4-dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine; tert-butyl 4-aminobenzoate With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h; Stage #2: p-vinylbenzylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 16h; Stage #3: trifluoroacetic acid tert-Butyl 4-(4-(2,2,2-trifluoroethoxy)-6-(4-vinylbenzylamino)-1,3,5-triazin-2-ylamino)benzoate, TFA salt. To a 0.1 M solution of 2,4-dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine in N-methylpyrrolidine (3 ml, 0.3 mmol) was added tert-butyl 4-aminobenzoate (58.0 mg, 0.300 mmol) and diisopropylethylamine (DIEA) (0.210 mL, 1.2 mmol) at r.t. The reaction mixture was stirred at r.t. for 30 mins and the completion of the reaction was monitored by LC/MS. (4-Vinylphenyl)methanamine (40.0 mg, 0.300 mmol) was added followed by DIEA (0.210 mL, 1.200 mmol). The reaction mixture was stirred at r.t. for 16 hrs. The reaction mixture was purified by preparative HPLC to afford 65 mg (35.2%) of the above compound as TFA salt. 1H NMR (500 MHz, MeOD) δ ppm 1.61 (s, 9H), 4.64 (s, 2H), 4.85-4.94 (m, 2H), 5.22 (d, J=10.99 Hz, 1H), 5.73-5.82 (m, 1H), 6.74 (dd, J=17.55, 10.83 Hz, 1H), 7.30-7.38 (m, 2H), 7.39-7.48 (m, 2H), 7.58-7.96 (m, 4H).
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2011/86858, 2011, A1 Location in patent: Page/Page column 49; 56
  • 49
  • [ 103946-54-9 ]
  • [ 50325-49-0 ]
  • [ 1286261-21-9 ]
Reference： [1]Chemical Communications,2011,vol. 47,p. 6548 - 6550
  • 50
  • [ 3739-94-4 ]
  • [ 50325-49-0 ]
  • [ 1333315-46-0 ]
YieldReaction ConditionsOperation in experiment
83% With trimethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
Reference： [1]Hibi, Yusuke; Ouchi, Makoto; Sawamoto, Mitsuo [Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7434 - 7437]
  • 51
  • [ 23165-29-9 ]
  • [ 50325-49-0 ]
  • [ 1359164-27-4 ]
YieldReaction ConditionsOperation in experiment
90% In dichloromethane at 20℃;
Reference： [1]Lu, Jinni; Toy, Patrick H. [Synlett, 2011, # 20, p. 2985 - 2990]
  • 52
  • [ 7327-99-3 ]
  • [ 50325-49-0 ]
  • C37H41N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In chloroform at 20℃; for 5h; Representative procedure of 2,6,9-triazabicyclo[3.3.1]nonanes General procedure: Preparation of 1a.To a solution of fumaraldehydic acid methyl ester (1) (10.0 mg, 87.6 lmol) in chloroform (100 lL) was added benzylamine (a) (14.4 lL, 131 lmol) at room temperature. After the resulting solution was stirred at room temperature for 5 h, it was directly purified by normal phase HPLC (column: KC-PACK SG-S, 10 250 mm; EtOAc in Hexane (25% over 40 min, 2.0 mL/min); UV detection at 254 nm; retention time:10.0 min); a pale yellow viscous liquid.
Reference： [1]Tanaka, Katsunori; Siwu, Eric R. O.; Hirosaki, Shinji; Iwata, Takayuki; Matsumoto, Risa; Kitagawa, Yasutaka; Okumura, Mitsutaka; Fukase, Koichi; Pradipta, Ambara R. [Tetrahedron Letters, 2012, vol. 53, # 44, p. 5899 - 5902,4]
  • 53
  • [ 1421037-02-6 ]
  • [ 50325-49-0 ]
  • N,N'-bis(2-hydroxyethyl)-2-((4-vinylbenzyl)amino)-1,4,5,8-tetracarboxylic acid 1,8:4,5-diimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;
Reference： [1]Doria, Filippo; Nadai, Matteo; Folini, Marco; Scalabrin, Matteo; Germani, Luca; Sattin, Giovanna; Mella, Mariella; Palumbo, Manlio; Zaffaroni, Nadia; Fabris, Daniele; Freccero, Mauro; Richter, Sara N. [Chemistry - A European Journal, 2013, vol. 19, # 1, p. 78 - 81]
  • 54
  • [ 50-00-0 ]
  • Fe2(μ-S)2(CO)6 [ No CAS ]
  • [ 50325-49-0 ]
  • [ 1446207-15-3 ]
YieldReaction ConditionsOperation in experiment
46% Stage #1: formaldehyd; p-vinylbenzylamine In tetrahydrofuran at 20℃; for 5h; Stage #2: Fe2(μ-S)2(CO)6 With lithium triethylborohydride In tetrahydrofuran at -78℃; for 0.25h; Stage #3: With trifluoroacetic acid In tetrahydrofuran at -78℃; for 0.25h;
Reference： [1]Heine, Daniel; Pietsch, Christian; Schubert, Ulrich S.; Weigand, Wolfgang [Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 10, p. 2171 - 2180]
  • 55
  • [ 50325-49-0 ]
  • [ 3674-06-4 ]
  • [ 1438776-76-1 ]
Reference： [1]Journal of Materials Chemistry B,2013,vol. 1,p. 2904 - 2910
  • 56
  • azidoacetic acid succinimidyl ester [ No CAS ]
  • [ 50325-49-0 ]
  • 2-azido-N-(4-vinylbenzyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% In dichloromethane at 0 - 20℃; Inert atmosphere;
Reference： [1]Chou, Ho-Hsuan; Raines, Ronald T. [Journal of the American Chemical Society, 2013, vol. 135, # 40, p. 14936 - 14939]
  • 57
  • [ 50325-49-0 ]
  • 2-azido-N-(4-oxianylbenzyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 0 - 20 °C / Inert atmosphere 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
Reference： [1]Chou, Ho-Hsuan; Raines, Ronald T. [Journal of the American Chemical Society, 2013, vol. 135, # 40, p. 14936 - 14939]
  • 58
  • [ 50325-49-0 ]
  • 2-diazo-N-(4-vinylbenzyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 0 - 20 °C / Inert atmosphere 2: 4-nitrophenyl 3-bis{3-[(2-methoxyethoxy)methoxymethyl]phenyl}phosphinopropanate / aq. phosphate buffer / 6 h / pH 7 / Inert atmosphere
Reference： [1]Chou, Ho-Hsuan; Raines, Ronald T. [Journal of the American Chemical Society, 2013, vol. 135, # 40, p. 14936 - 14939]
  • 59
  • [ 50325-49-0 ]
  • 2-diazo-N-(4-oxiranylbenzyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloromethane / 0 - 20 °C / Inert atmosphere 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 3: 4-nitrophenyl 3-bis{3-[(2-methoxyethoxy)methoxymethyl]phenyl}phosphinopropanate / aq. phosphate buffer / 6 h / pH 7 / Inert atmosphere
Reference： [1]Chou, Ho-Hsuan; Raines, Ronald T. [Journal of the American Chemical Society, 2013, vol. 135, # 40, p. 14936 - 14939]
  • 60
  • [ 56043-32-4 ]
  • [ 50325-49-0 ]
  • 1-(4-vinylbenzyl)-2,3,3-trimethylguanidine hydroiodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In tetrahydrofuran at 25℃; for 6h; 1-(4-Vinylbenzyl)-2,3,3-trimethylguanidine hydroiodide (3c) General procedure: In oneportion, amine (10 mmol) or α,ω-diamine (5 mmol) wasadded to a stirring suspension of S-methylisothiouroniumiodide 1 or 2 (10 mmol) in anhydrous THF (10 mL) at 25 °C.The mixture was stirred at 25 °C for 6-24 h, then evaporatedin vacuo. The residue was washed with Et2O, and theprecipitate was dried in vacuo for 12 h at 40 °C to give thecorresponding guanidine hydroiodide.
Reference： [1]Aoyagi, Naoto; Furusho, Yoshio; Endo, Takeshi [Synlett, 2014, vol. 25, # 7, p. 983 - 986]
  • 61
  • [ 4338-95-8 ]
  • [ 50325-49-0 ]
  • 4-vinylbenzylguanidine hydroiodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran at 25℃; for 6h; 4-Vinylbenzylguanidine hydroiodide (4c) General procedure: In oneportion, amine (10 mmol) or α,ω-diamine (5 mmol) wasadded to a stirring suspension of S-methylisothiouroniumiodide 1 or 2 (10 mmol) in anhydrous THF (10 mL) at 25 °C.The mixture was stirred at 25 °C for 6-24 h, then evaporatedin vacuo. The residue was washed with Et2O, and theprecipitate was dried in vacuo for 12 h at 40 °C to give thecorresponding guanidine hydroiodide.
Reference： [1]Aoyagi, Naoto; Furusho, Yoshio; Endo, Takeshi [Synlett, 2014, vol. 25, # 7, p. 983 - 986]
  • 62
  • 1,1’,2,2’-tetrakis(diphenylphosphino)-4,4’-di(4-oxo-2-methylbut-2-yl)ferrocene [ No CAS ]
  • [ 50325-49-0 ]
  • 1,1',2,2'-tetrakis(diphenylphosphino)-4,4'-[2-methyl-5-(4-vinylbenzylamino)pent-2-yl]ferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 15h;
55% With sodium triacetoxyborohydride In 1,2-dichloro-ethane at 20℃; for 15h; Inert atmosphere; Schlenk technique;
Reference： [1]Beauperin, Matthieu; Smaliy, Radomyr; Cattey, Helene; Meunier, Philippe; Ou, Jun; Toy, Patrick H.; Hierso, Jean-Cyrille [Chemical Communications, 2014, vol. 50, # 67, p. 9505 - 9508]
[2]Beaupérin, Matthieu; Smaliy, Radomyr; Cattey, Hélène; Meunier, Philippe; Ou, Jun; Toy, Patrick H.; Hierso, Jean-Cyrille [ChemPlusChem, 2015, vol. 80, # 1, p. 119 - 129]
  • 63
  • [ 1354901-66-8 ]
  • [ 50325-49-0 ]
  • [ 1354905-31-9 ]
YieldReaction ConditionsOperation in experiment
45% With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 15h;
Reference： [1]Beauperin, Matthieu; Smaliy, Radomyr; Cattey, Helene; Meunier, Philippe; Ou, Jun; Toy, Patrick H.; Hierso, Jean-Cyrille [Chemical Communications, 2014, vol. 50, # 67, p. 9505 - 9508]
  • 64
  • [ 1354905-33-1 ]
  • [ 50325-49-0 ]
  • 1,2-diphenylphosphino-1'-diisopropylphosphino-4-[2-methyl-5-(4-vinylbenzylamino)pent-2-yl]ferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 15h;
Reference： [1]Beauperin, Matthieu; Smaliy, Radomyr; Cattey, Helene; Meunier, Philippe; Ou, Jun; Toy, Patrick H.; Hierso, Jean-Cyrille [Chemical Communications, 2014, vol. 50, # 67, p. 9505 - 9508]
  • 65
  • [ 1620321-22-3 ]
  • [ 50325-49-0 ]
  • [ 1620321-24-5 ]
YieldReaction ConditionsOperation in experiment
55% With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 15h;
Reference： [1]Beauperin, Matthieu; Smaliy, Radomyr; Cattey, Helene; Meunier, Philippe; Ou, Jun; Toy, Patrick H.; Hierso, Jean-Cyrille [Chemical Communications, 2014, vol. 50, # 67, p. 9505 - 9508]
  • 66
  • [ 141109-47-9 ]
  • [ 50325-49-0 ]
  • N<SUP>1</SUP>,N<SUP>1</SUP>-diisopropyl-N<SUP>2</SUP>-(4-vinylbenzyl)oxalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: [di(propan-2-yl)amino](oxo)acetyl chloride; p-vinylbenzylamine In dichloromethane at 0℃; for 0.0833333h; Stage #2: With triethylamine In dichloromethane at 0 - 20℃; for 6h;
Reference： [1]Chen, Changpeng; Wang, Chao; Zhang, Jingyu; Zhao, Yingsheng [Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 942 - 949]
  • 67
  • [ 50325-49-0 ]
  • (S)-4-isopropyl-4-methyl-oxazolidine-2,5-dione [ No CAS ]
  • (S)-2-amino-2,3-dimethyl-N-(4-vinylbenzyl)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In dichloromethane at 40℃; Schlenk technique; Inert atmosphere; 1.2.2.(S)-2-Amino-2,3-dimethyl-N-(4-vinylbenzyl)butanamide (2) A solution of compound 1(410 mg, 2.6 mmol) and 4-vinylbenzylamine2 (387 mg, 2.9 mmol) in CH2Cl2(20 mL) was heated in Schlenk flask at 40 °C under argon conditions for 48 h.The product 2 (500 mg, 79 %) was obtained asyellowish oil after evaporation and purificationby silica gel column chromatography (CH2Cl2,CH3OH 5 % v/v, Rf0.6). -21.7 (c 1.25, CH3OH); 1H NMR (400 MHz, CDCl3):d 8.04 (brs, 1H, NH); 7.37 (d, 2H, 3J = 8.0 Hz, H-Ar), 7.23 (d, 2H, 3J = 8.0 Hz, H-Ar); 6.70 (dd, 1H, 3J = 17.6 and 11.0 Hz, CH=); 5.73 (d, 1H, 3J = 17.6 Hz, CH trans=); 5.23 (d, 1H, 3J = 11.0 Hz, CH cis=);4.41 (dd, 2H, 2J = 11.0 and 5.9 Hz, CH2);2.28 (sept, 1H, 3J = 7.0Hz, CH); 1.52 (brs, 2H, NH2); 1.28 (s, 3H, CH3); 0.89 (d,3H, 3J = 7.0 Hz, CH3);0.82 (d, 3H, 3J = 7.0 Hz,CH3); 13C NMR (100 MHz, CDCl3): d 177.3, 138.5, 136.7, 136.5, 127.9, 126.5, 113.8,60.5, 42.9, 34.2, 26.0, 17.7, 15.8. HRMS (ESI): Anal. Calcd for C15H23N2O[M + H]+: 269.16243; Found: 269.16090. Anal. Calcd. for C15H22N2O· H2O: C, 70.55; H, 9.08; N, 10.97; Found: C, 70.37; H, 8.92; N,11.22.
Reference： [1]Harmand, Lydie; Drabina, Pavel; Pejchal, Vladimír; Husáková, Lenka; Sedlák, Miloš [Tetrahedron Letters, 2015, vol. 56, # 45, p. 6240 - 6243]
  • 68
  • lactobionic acid [ No CAS ]
  • [ 50325-49-0 ]
  • vinyl benzyl galactopyranosylgluconamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol
Reference： [1]Choi, Yuri; Lee, Kyubae; Gupta, Kailash C.; Park, Soo-Young; Kang, Inn-Kyu [Journal of Materials Chemistry B, 2015, vol. 3, # 44, p. 8659 - 8669]
  • 69
  • [ 5464-11-9 ]
  • [ 50325-49-0 ]
  • 2-(4-vinylbenzylamino)-4,5-dihydro-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2-methylthio-2-imidazoline hydroiodide; p-vinylbenzylamine In tetrahydrofuran at 40℃; for 24h; Stage #2: With sodium hydroxide In water at 20℃; Synthesis of 3a-k and 4a-e; general procedure General procedure: In one portion, amine (11 mmol) was added to a stirring suspension of S-methylisothiouronium iodide 1 · HI or 2 · HI (10 mmol) in anhydrous THF (10 mL) at room temperature. The mixture was stirred at 40 °C for 24-120 h, then evaporated under reduced pressure. The residue was washed with Et2O, and the precipitate was dried in vacuo for 12 h at 40 °C to give quantitatively the corresponding guanidine hydroiodide. The hydroiodide was added to a 40% NaOHaq (10 mL). To the mixture was added CH2Cl2 or acetonitrile (20 mL), and was vigorously stirred at room temperature for 5-10 min. The layers were separated, and the aqueous layer was extracted with CH2Cl2 or acetonitrile (10 mL 2). The combined organic phase was dried with Na2SO4, then evaporated under reduced pressure. The residue was dried in vacuo for 12 h at 40 °C to give the corresponding cyclic guanidine in high yield (≥98%).
Reference： [1]Aoyagi, Naoto; Endo, Takeshi [Synthetic Communications, 2017, vol. 47, # 5, p. 442 - 448]
  • 70
  • [ 605-65-2 ]
  • [ 50325-49-0 ]
  • 4-[5-(dimethylamino)-1-naphthalenesulfonamido]methyl}styrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.5% With triethylamine In dichloromethane at 20℃; for 5.5h; Inert atmosphere; 3.2.3. 4-[5-(Dimethylamino)-1-naphthalenesulfonamido]methyl}styrene (DSL-Str) (4) To a stirred solution of AMN-Str 3 (512 mg, 3.8 mmol) and Et3N (0.53 mL, 456 mmol) indichloromethane (50 mL) a solution of dansyl chloride (1.23 g, 4.56 mmol) in dichloromethane (40 mL)was added dropwise at room temperature under a N2 atmosphere. After stirring at room temperaturefor 5.5 h, the reaction mixture was evaporated in vacuo. The resulting mixture was diluted with CHCl3and was then washed successively with water and brine and dried over anhyd MgSO4. The organic mixture was filtered and evaporated in vacuo. The residual syrup was applied to a column of silicagel with 5:2 (v/v) hexane-EtOAc as the eluent to give pure DSL-Str 4 [26] (1.052 g, 75.5%) as yellowcrystals: mp 103.0-103.4 C; Rf 0.40 [5:2 (v/v) hexane-EtOAc]; IR (NEAT): 3286.70, 3273.20 (N-H),3084.18 (C-H, Ph), 1625.99 (N-H), 1305.81 (C-N), 1066.64 (S=O) cm1; 1H-NMR (500 MHz, CDCl3): δ 8.53 (d, 2 H, J = 8.50 Hz, Naph), 8.27 (t, 2 H, J = 8.85 Hz, J = 7.45 Hz, Naph), 7.53 (dt, 2 H, J = 10.90 Hz,J = 17.60 Hz, Naph), 7.19 (d, 2 H, J = 7.95 Hz, Ph) 7.19 (d, 1 H, J = 6.35 Hz, Naph), 7.01 (d, 2 H,J = 7.80 Hz, Ph), 6.60 (dd, 1 H, J =10.87 Hz, J = 17.53 Hz, Naph), 5.66 (br dd, 1 H, J = 17.61 Hz, Naph),5.20 (br dd, 1 H, J = 10.85 Hz, Naph), 4.86 (t, 2 H, J = ~6 Hz, NH), 4.06 (d, 2 H, J = 6.05 Hz, CH2), 2.89 (s,6 H, NCH3 2) (1H-MNR spectrum can be found in Supplementary Materials).
Reference： [1]Hayama, Riho; Koyama, Tetsuo; Matsushita, Takahiko; Hatano, Ken; Matsuoka, Koji [Molecules, 2018, vol. 23, # 11]
  • 71
  • [ 50325-49-0 ]
  • [ 58-85-5 ]
  • 4-({5-[(3aR,6S,6aS)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanamido}methyl)styrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.3% With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 3.2.4. 4-({5-[(3aR,6S,6aS)-2-Oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanamido}methyl)-styrene (BTN-Str) (5) To a stirred solution of AMN-Str 3 (60.0 mg, 0.45 mmol) and biotin (121 mg, 495 mmol) in DMF(1 mL) was added DMT-MM (150 mg, 0.54 mmol) at room temperature under a N2 atmosphere.After stirring at room temperature for 1.5 h, the white suspension was poured into ice-cold waterand extracted with EtOAc. When extraction with EtOAc was performed, an insoluble mass was alsoobserved. The organic solution and the insoluble mass were successively washed with ice-cold water,satd aq NaHCO3 and brine, and the whole mixture was filtrated to give a white amorphous powderBTN-Str 5 (148 mg, 91.3%): Rf = 0.53 [5:1 (v/v) CHCl3-MeOH]; 1H-NMR (500 MHz, DMSO-d6): δ 8.34 (br s, 1 H, NHCH2), 7.41 (d, 2 H, J = 8.15 Hz, Ph), 7.21 (d, 2 H, J = 8.15 Hz, Ph), 6.71 (dd, 1 H,Jcis = 10.95 Hz, Jtrans = 17.65 Hz, CH=CH2), 6.42 [br s, 1 H, NH (biotin)], 6.37 [s, 1 H, NH (biotin)], 5.79(dd, 1 H, Jgem = 0.70 Hz, trans of CH2=), 5.22 (d, 1 H, cis of CH2=), 4.30 [dd, 1 H, J =5.15 Hz, J =7.65 Hz,CHCH2 (biotin)], 4.24 (d, 2 H, J = 5.95 Hz, PhCH2), 4.12 (ddd, 1 H, J = 1.80 Hz, J = 4.35 Hz, J = 7.45 Hz,NHCHCH), 3.09 (ddd, 1 H, J = 2.55 Hz, J = 4.35 Hz, J = 10.5 Hz, SCH), 2.82 (dd, 1 H, Jgem = 12.4 Hz,SCHa), 2.58 (d, 1 H, SCHb), 2.14 (t, 2 H, J =7.45 Hz, CH2CO), 1.5 (m, 4 H, CH2 2) (1H-MNR spectrumcan be found in Supplementary Materials).
Reference： [1]Hayama, Riho; Koyama, Tetsuo; Matsushita, Takahiko; Hatano, Ken; Matsuoka, Koji [Molecules, 2018, vol. 23, # 11]
  • 72
  • C20H31NO13 [ No CAS ]
  • [ 50325-49-0 ]
  • C29H40N2O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.7% With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In dichloromethane at 20℃; for 3.5h; Inert atmosphere; 3.2.7. 8-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-dioxaoctanoic Acid4-vinybenzylamide (9) To a stirred solution of carboxylic acid 8 (4.0 g, 8.11 mmol) and AMN-Str 3 (1.24 g, 9.31 mmol)in dichloromethane (20 mL) was added DMT-MM (2.69 g, 9.72 mmol) and the resulting suspensionwas stirred at room temperature under a N2 atmosphere for 3.5 h. The reaction mixture was pouredinto ice-cold water and extracted with EtOAc. The organic layer was successively washed with satdaq NaHCO3 and brine. The organic layer was dried over anhyd MgSO4 and concentrated in vacuo.The residue was purified by silica gel chromatography with 50:1 (v/v) CHCl3-MeOH as the eluent togive styrene derivative 9 (3.82 g, 77.7%) as a colorless syrup: Rf = 0.48 [10:1 (v/v) CHCl3-MeOH];IR (NEAT) 3306 (N-H), 3086, 3007 (C-H, Ph), 2937 (C-H), 1748 (C=O, ester), 1667 (C=O, Amide I),1651 ( C=C), 1537 (N-H, Amide II), 1234 (C-O), 1043 (C-O-C) cm1; 1H-NMR (400 MHz, CDCl3): δ 7.39 (d, 2 H, Jvic =8.1 Hz, Ph), 7.27 (d, 2 H, Jvic = 8.3 Hz, Ph), 7.23 (s, 1 H, NHCH2), 6.71 (dd, 1 H,Jcis = 10.9 Hz, Jtrans = 17.6 Hz, CH=CH2), 6.30 (d, 1 H, J2,NH = 8.52 Hz, NHAc), 5.75 (dd, 1 H, Jgem =0.60 Hz, trans of CH2=), 5.35 (dd, 1 H, J2,3 = 10.5 Hz, J3,4 = 9.34 Hz, H-3), 5.26 (dd, 1 H, cis of CH2=),5.03 (t, 1 H, J4,5 = 9.72 Hz, H-4), 4.79 (d, 1 H, J1,2 = 8.36 Hz, H-1), 4.49 (d, 2 H, Jvic = 5.92 Hz, NHCH2),4.24 (dd, 1 H, J5,6b = 4.66 Hz, J6a,6b = 12.3 Hz, H-6b), 4.19 (d, 1 H, Jgem = 15.7 Hz, NCOCHb), 4.13 (d, 1H, NCOCHa), 4.10 (dd, 1 H, J5,6a = 2.36 Hz, H-6a), 3.88 (m, 1 H, OCHb), 3.71-3.60 (m, 9 H, H-2, H-5,OCHb, OCH2 3), 2.07, 2.01, 2.01, 1.89 (each s, 12 H, COCH3 4) (1H-MNR spectrum can be foundin Supplementary Materials); 13C-NMR (100 MHz,CDCl3): δ 170.86, 170.65, 170.42, and 169.59 (C=O 4), 136.43 (CH=), 128.17 (Ph), 126.66 (Ph), 114.27 (CH2=), 100.60 (C-1), 72.30 (C-3), 71.87, 71.03, 70.89,70.70 and 70.52 (C-5, OCH2 4), 68.86 (C-4), 68.62 (OCHa,b), 62.26 (C-6), 55.15 (C-2), 42.75 (NCH2),23.29 (NCOCH3), 20.89, 20.84, and 20.77 (COCH3 3); MALDI-TOF MS calcd for [M + H]+: 609.265.Found: m/z 609.228, [M + Na]+: 631.247. Found: m/z 631.242, [M + K]+: 647.221. Found: m/z 647.225.
Reference： [1]Hayama, Riho; Koyama, Tetsuo; Matsushita, Takahiko; Hatano, Ken; Matsuoka, Koji [Molecules, 2018, vol. 23, # 11]
  • 73
  • C14H20F2N2 [ No CAS ]
  • [ 50325-49-0 ]
  • [ 503-38-8 ]
  • 1-[(2,4-difluorophenyl)methyl]-3-[(4-ethenylphenyl)methyl]-1-(1-methylpiperidin-4-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: p-vinylbenzylamine; trichloromethyl chloroformate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: C14H20F2N2 In dichloromethane at 20℃; 94 Scheme S 1 : General procedure A (GP A). General procedure: Amine 1 (1.1 equiv.) was added to ketone 2 (1.0 equiv.) in CH2CI2 followed by addition of sodium triacetoxyborohydride (1.5 equiv.). The reaction mixture was stirred for 3 hours at room temperature, then concentrated under reduced pressure. The residue was diluted with NaOH (1 M, aq.) and extracted with CH2CI2. The organic phase was dried and concentrated under reduced pressure to give secondary amines 3, that was used in the next step without purification or purified by silica gel column chromatography. A solution of amine 4 (1.0 equiv.) in CH2CI2 was added dropwise to a solution of diphosgene (0.5 equiv.) in CH2CI2 at room temperature. DIPEA (3.0 equiv.) was added and the resulting mixture was stirred for 5 minutes at room temperature. Thereafter a solution of secondary amine 3 (1.1 equiv.) in CH2CI2 was added and the reaction mixture was stirred overnight at room temperature. The mixture was (0651) concentrated under reduced pressure and the desired urea 5 was purified by preparative HPLC eluting with acetonitrile in water (containing 0.1% trifluoroacetic acid) to afford the TFA salt of the product or purified by preparative HPLC eluting with acetonitrile in water, containing 6 ppm ammonia (28% aq.), to afford the product as the free base.
Reference： [1]Current Patent Assignee: ACADIA PHARMACEUTICALS INC - WO2019/40107, 2019, A1 Location in patent: Paragraph 00427-00428; 00436; 00565-00566
  • 74
  • C14H20F2N2 [ No CAS ]
  • [ 50325-49-0 ]
  • 1-[(2,4-difluorophenyl)methyl]-3-({4-[1,2-dihydroxyethyl]phenyl}methyl)-1-(1-methylpiperidin-4-yl)urea trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 20 °C 1.2: 20 °C 2.1: water; potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / acetone / 21 h / 20 °C
Reference： [1]Current Patent Assignee: ACADIA PHARMACEUTICALS INC - WO2019/40107, 2019, A1
  • 75
  • [ 2420-87-3 ]
  • [ 50325-49-0 ]
  • C34H24N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
29.4 g (0.1 mol) of <strong>[2420-87-3]3,3',4,4'-biphenyltetracarboxylic dianhydride</strong> (BPDA) solid powderAnd 33.25 g (0.25 mol) of 4-vinylbenzylamine liquid is added by 150 g of dimethylacetamideAnd 50 grams of toluene mixed solvent,The mixture was heated in a glass stirred reaction tank and continuously stirred at a constant temperature of 35 C until the solid powder was completely dissolved to form a solution.After continuing the reaction at a constant temperature of 35 C for 8 hours,Add 0.5 grams of triphenylphosphine (TPP) and 1 gram of acetic anhydride.Reheat to 180 C for 8 hours.The yellow solid product A (the following structural formula) is obtained as the ethylene benzyl imide resin.
Reference： [1]Patent: CN109503456,2019,A .Location in patent: Paragraph 0137-0144
  • 76
  • [ 50325-49-0 ]
  • 4-vinylbenzylammonium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide In water; isopropyl alcohol at 0 - 20℃; for 2h;
Reference： [1]Proppe, Andrew H.; Wei, Mingyang; Chen, Bin; Quintero-Bermudez, Rafael; Kelley, Shana O.; Sargent, Edward H. [Journal of the American Chemical Society, 2019, vol. 141, # 36, p. 14180 - 14189]
  • 77
  • [ 50325-49-0 ]
  • 4-vinylbenzylammonium iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen iodide In water; isopropyl alcohol at 0 - 20℃; for 2h;
Reference： [1]Proppe, Andrew H.; Wei, Mingyang; Chen, Bin; Quintero-Bermudez, Rafael; Kelley, Shana O.; Sargent, Edward H. [Journal of the American Chemical Society, 2019, vol. 141, # 36, p. 14180 - 14189]
  • 78
  • [ 50325-49-0 ]
  • C15H17N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 47 h / 0 - 25 °C / Inert atmosphere 2: toluene / 13 h / 110 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - US2020/24237, 2020, A1 Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US10689478, 2020, B2
  • 79
  • [ 50325-49-0 ]
  • C18H17N [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With cobalt nanoparticles encapsulated within nitrogen doped graphitic shells prepared via pyrolysis of poly([1,3-bis(4-vinylbenzyl)imidazolium]CoCl4) at 800 oC In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
Reference： [1]Cui, Xinjiang; Li, Wu; Junge, Kathrin; Fei, Zhaofu; Beller, Matthias; Dyson, Paul J. [Angewandte Chemie - International Edition, 2020, vol. 59, # 19, p. 7501 - 7507][Angew. Chem., 2020, vol. 132, # 19, p. 7571 - 7577,7]
  • 80
  • [ 50325-49-0 ]
  • 4-aminomethylstyrene hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With hydrogenchloride In methanol; isopropyl alcohol for 3h;
Reference： [1]Bian, Guomin; Huang, Xianpei; Liu, Fuyao; Qi, Yonglin; Sun, Zunming; Yang, Xinlin; Yang, Xinyue; Zhang, Mengmeng; Zhang, Wangqing [New Journal of Chemistry, 2020, vol. 44, # 22, p. 9546 - 9556]
  • 81
  • [ 24424-99-5 ]
  • [ 50325-49-0 ]
  • N-Boc-2-(4-(aminomethyl)phenyl)propanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / methanol / 12 h / 20 °C 2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(1,5-cyclooctadiene)nickel (0) / toluene / 24 h / 120 °C / Inert atmosphere; Glovebox; Sealed tube
Reference： [1]Bhawal, Benjamin N.; Ehinger, Christian; Morandi, Bill; Reisenbauer, Julia C. [Journal of the American Chemical Society, 2020, vol. 142, # 25, p. 10914 - 10920]
  • 82
  • [ 50325-49-0 ]
  • [ 3435-51-6 ]
  • [ 25309-65-3 ]
YieldReaction ConditionsOperation in experiment
1: 73.7 %Chromat. 2: 17.8 %Chromat. With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;
Reference： [1]Chen, Hua; Fu, Haiyan; Ji, Li; Li, Ruixiang; Nie, Xufeng; Zheng, Yanling [Journal of Catalysis, 2020, vol. 391, p. 378 - 385]
  • 83
  • [ 50325-49-0 ]
  • C10H9F3NO2S(1-)*K(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 5 h / -78 - 25 °C 2: potassium carbonate / acetonitrile / 25 °C / Inert atmosphere
Reference： [1]Schkeryantz, Luke A.; Zheng, Jingfeng; McCulloch, William D.; Qin, Lei; Zhang, Songwei; Moore, Curtis E.; Wu, Yiying [Chemistry of Materials, 2020, vol. 32, # 24, p. 10423 - 10434]
  • 84
  • [ 358-23-6 ]
  • [ 50325-49-0 ]
  • C10H10F3NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at -78 - 25℃; for 5h;
Reference： [1]Schkeryantz, Luke A.; Zheng, Jingfeng; McCulloch, William D.; Qin, Lei; Zhang, Songwei; Moore, Curtis E.; Wu, Yiying [Chemistry of Materials, 2020, vol. 32, # 24, p. 10423 - 10434]
  • 85
  • [ 384-98-5 ]
  • [ 50325-49-0 ]
  • 2,4,6-trimethyl-N-(4-vinylbenzyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With 1,1,3,3-Tetramethyldisiloxane; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 25℃; for 24h; Sealed tube;
Reference： [1]Wei, Mingjie; Liang, Dacheng; Cao, Xiaohui; Luo, Wenjun; Ma, Guojian; Liu, Zeyuan; Li, Le [Angewandte Chemie - International Edition, 2021, vol. 60, # 13, p. 7397 - 7404][Angew. Chem., 2021, vol. 133, # 13, p. 7473 - 7480,8]
  • 86
  • [ 40018-26-6 ]
  • [ 50325-49-0 ]
  • 7-(4-vinylbenzyl)methyl-2,5-dithia-7-azabicyclo[2.2.1]heptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate In water for 3h; 10 Example 10 - Modified polystyrene 4-Vinylbenzylamine (Feng, Designed monomers & Polymers 2017) is added dropwise to an aqueous suspension of 2, 5-dihydroxy-1 ,4-dithiane being stirred with a 10% catalytic amount of NaOAc. After 3 hours the reaction mixture is extracted with ethylacetate, the organic layer is dried with MgS04, filtered, and rotovaped to yield 7-(4-vinylbenzene)methyl-2,5-dithia-7azabicyclo[2.2.1]heptane. This monomer is polymerized either neat or in various proportions with styrene, in the presence of azobisisobutyronitrile (AIBN) at 35°C to produce a solid, waxy material. The material is soluble in chloroform and 1 H NMR reveals the presence of the 2,5-dithio-7- azabicyclo[2.2.1]heptane unit, together with the backbone of the polymer.
Reference： [1]Current Patent Assignee: KASIS ENV - WO2021/62549, 2021, A1 Location in patent: Paragraph 00224
  • 87
  • [ 945-51-7 ]
  • [ 50325-49-0 ]
  • [ 139-66-2 ]
  • C18H17N [ No CAS ]
YieldReaction ConditionsOperation in experiment
With nitrogen-doped carbon supported nickel catalyst In hexane at 170℃; for 13h; Inert atmosphere; Autoclave; 2.4. Catalyst performance test General procedure: The reaction was conducted in a 40 mL stainless steel autoclave.In a typical run, 0.5 mmol of benzylamine, 0.5 mmol ofdiphenyl sulfoxide, 40 mg of Ni/NC-600 and 10 mL of solvent were added into the reactor, and the air in the autoclave wasremoved by the exchange with N2 for several times. Then, theautoclave was charged with 10 bar N2. Finally, the reactor washeated from room temperature to 180 °C and kept at 180 °C for 6 h with magnetic stirring at 1000 rpm. After the reaction, the autoclave was cooled down to room temperature, the Ni/NC-600 catalyst was collected by centrifugation for further use, andthe liquid phase was analyzed by Agilent GC 7820A.
Reference： [1]Li, Bo; Liu, Bing; Liu, Xixi; Wang, Wei; Wang, Yanxin; Xiang, Nian; Zhang, Zehui [Journal of Catalysis, 2021, vol. 401, p. 81 - 88]
  • 88
  • [ 1378285-65-4 ]
  • [ 50325-49-0 ]
  • N-((6R,7R,11R,12R)-2,2,16,16-tetramethyl-4,14-dioxo-6,7,11,12-tetraphenyl-3,15-dioxa-5,8,10,13-tetraazaheptadecan-9-ylidene)-1-(4-vinylphenyl)methanaminium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; mercury dichloride In N,N-dimethyl-formamide for 72h; Schlenk technique; Inert atmosphere;
Reference： [1]Chassillan, Louis; Guillot, Régis; Kobayashi, Shū; Toffano, Martial; Vo-Thanh, Giang; Yamashita, Yasuhiro; Yoo, Woo-Jin [Organic and Biomolecular Chemistry, 2021, vol. 19, # 48, p. 10560 - 10564]

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