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[ CAS No. 1134-87-8 ] {[proInfo.proName]}

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Chemical Structure| 1134-87-8
Chemical Structure| 1134-87-8
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Product Details of [ 1134-87-8 ]

CAS No. :1134-87-8 MDL No. :MFCD00544307
Formula : C12H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 190.24 Pubchem ID :-
Synonyms :

Safety of [ 1134-87-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1134-87-8 ]

* 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 [ 1134-87-8 ]

[ 1134-87-8 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 4335-90-4 ]
  • [ 1134-87-8 ]
YieldReaction ConditionsOperation in experiment
94% With triethylsilane; iron(III) chloride hexahydrate In dichloromethane at 20℃; for 3.5h; chemoselective reaction;
90% With formic acid; triethylamine; N-tosylethylenediamine In dichloromethane at 30℃; for 5.5h;
With acetic acid; platinum Hydrogenation;
With formic acid; triethylamine at 145 - 150℃;
60 %Spectr. With acetic acid; zinc In methanol; benzene at 0℃; for 0.5h; chemoselective reaction; One-Pot (OP) Reductive Knoevenagel Condensation with the Zn-AcOH System; General Procedure 2 (GP2) General procedure: CAUTION Although we did not experience any problems with the studied reactions, Zn dust is potentially flammable material. Its reactions with acids are highly exothermic with releasing flammable H2 gas. Safety precautions are required. A mixture of the corresponding aldehyde (50 mmol), active methylene compound (50 mmol), piperidine (0.25 mL, 2.5 mmol), and AcOH (0.58 mL, 10 mmol) in benzene (or toluene, if noticed, 40 mL) was heated under reflux with a 20 mL Dean-Stark trap for 1-5 h (until ca. 1 mL of H2O was collected). The reaction mixture was allowed to cool down to r.t. Then it was diluted with the corresponding alcohol (50 mL) (Scheme 4), followed by the addition of Zn metal in either powdered or dust form (9.8 g, 0.15 mol) and AcOH (5.8 mL, 0.10 mol). In the case of cyano and keto derivatives, AcOH was added dropwise within 5 min under vigorous stirring. The reaction mixture was stirred under conditions specified (Schemes 4 and 5). The resulting suspension was cooled, if needed, and then the remaining Zn metal was filtered off using EtOAc for washing (Büchner funnel was used in the case of Zn dust). The combined organic fractions were concentrated under reduced pressure. The residue was mixed up with brine (50 mL) and extracted with EtOAc (2 × 120 mL). The combined organic fractions were washed once with H2O (50 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc, or CH2Cl2).
With triethylsilane; iron(III) chloride hexahydrate In dichloromethane at 20℃;

Reference： [1]Syamala, Lakshmi V.R. Babu; Mete, Trimbak B.; Bhat, Ramakrishna G. [Tetrahedron Letters, 2018, vol. 59, # 34, p. 3288 - 3291]
[2]Xue, Dong; Chen, Ying-Chun; Cui, Xin; Wang, Qi-Wei; Zhu, Jin; Deng, Jin-Gen [Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3584 - 3591]
[3]Jadot [Bulletin des Societes Chimiques Belges, 1948, vol. 57, p. 353]
[4]Harries; Gollnitz [Justus Liebigs Annalen der Chemie, 1904, vol. 330, p. 233]
[5]Sekiya,M.; Suzuki,K. [Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 1530 - 1534]
[6]Ivanov, Konstantin L.; Melnikov, Mikhail Ya.; Budynina, Ekaterina M. [Synthesis, 2021, vol. 53, # 7, p. 1285 - 1291]
[7]Liu, Jia-Hui; Lv, Xue-Jiao; Liu, Yan-Kai [Organic Letters, 2023, vol. 25, # 10, p. 1706 - 1710]
  • 2
  • [ 7357-70-2 ]
  • [ 1134-87-8 ]
  • [ 128917-85-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol for 0.25h; Heating; Yield given;
Reference： [1]Wagner; Vieweg; Leistner; Bohm; Krasselt; Hanfe ld; Prantz; Grupe [Pharmazie, 1990, vol. 45, # 2, p. 102 - 109]
  • 3
  • [ 100-39-0 ]
  • [ 14024-48-7 ]
  • [ 1134-87-8 ]
  • [ 53316-00-0 ]
YieldReaction ConditionsOperation in experiment
1: 15% 2: 51% In chloroform at 120℃; for 1h;
Reference： [1]Vallribera, Adelina; Marquet, Jorge; Moreno-Manas, Marcial; Cayon, Eduard [Tetrahedron, 1993, vol. 49, # 29, p. 6437 - 6450]
  • 4
  • [ 1134-87-8 ]
  • [ 23147-77-5 ]
YieldReaction ConditionsOperation in experiment
81% With hydrazine hydrate In ethanol
80% With hydrazine hydrate In ethanol Heating;
With hydrazine hydrate In dichloromethane at 20℃; for 24h;
Reference： [1]Location in patent: scheme or table Olguin, Juan; Brooker, Sally [New Journal of Chemistry, 2011, vol. 35, # 6, p. 1242 - 1253]
[2]Jeffery, John C.; Kurek, Stefan S.; McCleverty, Jon A.; Psillakis, Elefteria; Richardson, Rob M.; et al. [Journal of the Chemical Society, Dalton Transactions, 1994, # 17, p. 2559 - 2564]
[3]Solodenko, Wladimir; Broeker, Patrick; Messinger, Josef; Schoen, Uwe; Kirschning, Andreas [Synthesis, 2006, # 3, p. 461 - 466]
  • 5
  • [ 3775-29-9 ]
  • [ 1134-87-8 ]
  • 2-Acetyl-2-benzyl-4-methylene-cyclohexanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With triphenylphosphine In acetonitrile at 40℃; for 6h;
Reference： [1]Buono, Frédéric; Tenaglia, Alphonse [Synlett, 1998, # 10, p. 1153 - 1155]
  • 6
  • [ 175204-69-0 ]
  • [ 1134-87-8 ]
  • 4-(4-Benzyl-3,5-dimethyl-pyrazol-1-yl)-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With p-toluenesulfonic acid monohydrate In dichloromethane; dimethyl sulfoxide; ethyl acetate 13.2 Step 2) Preparation of Compound 142. Step 2) Preparation of Compound 142. A suspension of 4-hydrazino-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine (5.25 g, 25.6 mmol), 3-benzylpentane-2,4-dione (5.0 g, 28.4 mmol), and p-toluenesulfonic acid monohydrate (0.475 g, 2.50 mmol) in dimethylsulfoxide (50 mL) was heated to 75° C. for 20 hours. The reaction mixture was allowed to cool to room temperature, and the suspension was dissolved in methylene chloride (700 mL). The solution was washed three times with water, once with brine, dried (magnesium sulfate), and concentrated to afford a moist solid. The crude product was suspended in ethyl acetate (50 mL), heated to reflux, allowed to cool to room temperature, and filtered (repeated three times). The final productproduct was obtained as a white solid containing 3% dimethylsulfoxide by weight: 8.63 g (90%). 1H NMR (CDCl3) δ 8.84-8.53 (m, 1H), 8.48 (d, J=7.9 Hz, 1H), 7.86-7.91 (m, 1H), 7.46-7.50 (m, 1H), 7.13-7.30 (m, 5H), 6.61 (br s, 1H), 6.40 (br s, 1H), 3.83 (s, 2H), 2.79 (s, 3H), 2.24 (s, 3H) ppm. MS (ESI) m/z 358 (M+H+).
Reference： [1]Current Patent Assignee: SANOFI - US2002/119988, 2002, A1

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