[ CAS No. 637-44-5 ] {[proInfo.proName]}

Name: 637-44-5|3-Phenylpropiolic acid|95%
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Quality Control of [ 637-44-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 637-44-5 ]

Product Details of [ 637-44-5 ]

CAS No. :	637-44-5	MDL No. :	MFCD00004361
Formula :	C₉H₆O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XNERWVPQCYSMLC-UHFFFAOYSA-N
M.W :	146.14	Pubchem ID :	69475
Synonyms :		Chemical Name :	3-Phenylpropiolic acid

Calculated chemistry of [ 637-44-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.96
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.3
Log Po/w (XLOGP3) :	2.04
Log Po/w (WLOGP) :	1.2
Log Po/w (MLOGP) :	1.9
Log Po/w (SILICOS-IT) :	1.55
Consensus Log Po/w :	1.6

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.537 mg/ml ; 0.00367 mol/l
Class :	Soluble
Log S (Ali) :	-2.45
Solubility :	0.517 mg/ml ; 0.00354 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.83
Solubility :	2.15 mg/ml ; 0.0147 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.32

Safety of [ 637-44-5 ]

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

Application In Synthesis of [ 637-44-5 ]

* 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.

Upstream synthesis route of [ 637-44-5 ]
Downstream synthetic route of [ 637-44-5 ]

[ 637-44-5 ] Synthesis Path-Upstream 1~8

1
[ 150-76-5 ]
[ 637-44-5 ]
[ 40547-03-3 ]
[ 26964-24-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	With trifluoroacetic acid In chlorobenzene at 100℃; Inert atmosphere	General procedure: A mixture of Phenol derivatives (1) (1.0 mmol), trifluoromethanesulfonic acid (1.0 mmol) and propiolic acid (2a) (0.5 mmol) in PhCl (3.0 mL) was stirred at 100 °C for 1 h. After completion of reaction as indicated by TLC, the reaction mixture was poured into H₂O, neutralized with NaHCO₃solution and extracted CH₂Cl₂. The organic layer was washed with 2M NaOH, dried over anhydrous MgSO₄. The solvent was removed in vaccum, and the products were purified by silica gel columnchromatography (EtOAc-Hex) to give the desired product 3.
48%	With trifluorormethanesulfonic acid In chlorobenzene at 100℃; for 3 h;	The title compound was synthesized in the same manner as in Example 1, except that 4-methoxyphenol was used instead of phenol, 3-phenylpropiolic acid was used instead of propiolic acid, and the reaction time was 3 hours

Reference： [1] Tetrahedron Letters, 2016, vol. 57, # 32, p. 3600 - 3603
[2] Patent: KR101656876, 2016, B1, . Location in patent: Paragraph 0160; 0161

2
[ 672-13-9 ]
[ 637-44-5 ]
[ 26964-24-9 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 24, p. 6606 - 6609

3
[ 95062-66-1 ]
[ 637-44-5 ]
[ 26964-24-9 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 6, p. 1218 - 1231

4
[ 637-44-5 ]
[ 26964-24-9 ]

Reference： [1] Journal of Organic Chemistry, 1986, vol. 51, # 23, p. 4432 - 4436
[2] Journal of Organic Chemistry, 1986, vol. 51, # 23, p. 4432 - 4436

5
[ 15164-44-0 ]
[ 637-44-5 ]
[ 57341-98-7 ]

Reference： [1] Advanced Synthesis and Catalysis, 2009, vol. 351, # 17, p. 2827 - 2832
[2] RSC Advances, 2016, vol. 6, # 75, p. 71117 - 71121

6
[ 104-88-1 ]
[ 637-44-5 ]
[ 57341-98-7 ]

Reference： [1] RSC Advances, 2016, vol. 6, # 76, p. 72810 - 72814
[2] Journal of Organic Chemistry, 2013, vol. 78, # 9, p. 4543 - 4550

7
[ 1122-91-4 ]
[ 637-44-5 ]
[ 57341-98-7 ]

Reference： [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 4, p. 705 - 710

8
[ 124-38-9 ]
[ 536-74-3 ]
[ 33578-00-6 ]
[ 637-44-5 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1985, vol. 104, # 9, p. 226 - 230

[ 637-44-5 ] Synthesis Path-Downstream 1~88

1
[ 6293-56-7 ]
[ 637-44-5 ]
[ 85364-53-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 379 - 382
[2]Heterocycles,1983,vol. 20,p. 201 - 203

2
[ 124-38-9 ]
[ 536-74-3 ]
[ 33578-00-6 ]
[ 637-44-5 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1985,vol. 104,p. 226 - 230

3
[ 60753-14-2 ]
[ 637-44-5 ]
[ 97607-58-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 379 - 382

4
[ 637-44-5 ]
[ 108-46-3 ]
[ 2555-30-8 ]
[ 6665-86-7 ]
[ 128190-96-5 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4349 - 4356
[2]Journal of Organic Chemistry,1990,vol. 55,p. 4349 - 4356

5
[ 136-77-6 ]
[ 637-44-5 ]
6-Hexyl-7-hydroxy-4-phenyl-chromen-2-one [ No CAS ]

Reference： [1]Journal of Chemical Research - Part S,1998,p. 392 - 393

6
[ 637-44-5 ]
[ 6665-86-7 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4349 - 4356

7
[ 637-44-5 ]
[ 936-44-7 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1940,vol. 59,p. 1093,1100

8
[ 37088-66-7 ]
[ 637-44-5 ]
[ 811461-13-9 ]

Reference： [1]Patent: WO2004/113290,2004,A1 .Location in patent: Page/Page column 39-40
[2]Patent: WO2004/113290,2004,A1 .Location in patent: Page/Page column 39-40
[3]Patent: WO2004/113290,2004,A1 .Location in patent: Page/Page column 39-40

9
[ 124-38-9 ]
[ 536-74-3 ]
[ 36122-35-7 ]
[ 635-51-8 ]
[ 621-82-9 ]
[ 637-44-5 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 5866 - 5872

10
[ 2786-51-8 ]
[ 637-44-5 ]
[ 1204299-66-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2009,vol. 48,p. 853 - 857

11
[ 62002-31-7 ]
[ 637-44-5 ]
[ 303020-66-8 ]

Yield	Reaction Conditions	Operation in experiment
		1-Hydroxy-7-azabenzotriazole (0.32 g, 2.4 mmol) was added to a solution of phenylpropiolic acid (0.34 g, 2.4 mmol) in dichloromethane (30 mL). The solution was cooled to 0 C. EDC (0.45 g, 2.4 mmol) was added. The reaction mixture was stirred at 0 C. for 20 min. 4,5,6,7-Tetrahydroimidazo[4,5-c]pyridine dihycrochloride (0.50 g, 2.3 mmol) was added. Ethyldiisopropylamine (0.40 mL, 2.3 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. It was diluted with ethyl acetate (100 mL) and washed with 10% aqueous sodium hydrogensulfate solution (100 mL). The aqueous phase was extracted with ethyl acetate (360 mL): It was added a 1 N sodium hydroxide solution until pH 12 was obtained. It was extracted with ethyl acetate (390 mL). These extracts were combined and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 50 mg of the title compound. 1H NMR (CDCl3, 2 rotamers): delta2.75 and 2.85 (both t, together 2H); 4.03 and 4.15 (both t, together 2H); 4.75 and 4.92 (both s, together 1H); 7.10-7.70 (m, 6H).

Reference： [1]Patent: US6908926,2005,B1 .Location in patent: Page/Page column 65-66

12
[ 20651-67-6 ]
[ 637-44-5 ]
[ 19165-51-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2827 - 2832

13
[ 694-32-6 ]
[ 637-44-5 ]
[ 1007597-65-0 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 2000 - 2003

14
[ 13669-51-7 ]
[ 637-44-5 ]
[ 1234580-79-0 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 9280 - 9282

15
[ 31599-60-7 ]
[ 637-44-5 ]
[ 1262044-52-9 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 9049 - 9051

16
[ 698-70-4 ]
[ 637-44-5 ]
[ 14301-08-7 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 9049 - 9051

17
[ 2632-10-2 ]
[ 637-44-5 ]
[ 1268686-74-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 31 - 35

18
[ 2632-10-2 ]
[ 637-44-5 ]
[ 1268686-58-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 31 - 35

19
[ 5326-38-5 ]
[ 637-44-5 ]
1-nitro-3-methyl-4-(phenylethynyl)benzene [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 4751 - 4755

20
[ 626-00-6 ]
[ 637-44-5 ]
[ 13141-36-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(l) iodide; potassium carbonate; triphenylphosphine; In water; at 100℃; for 48h;Inert atmosphere;	General procedure: Aryl halide (0.5 mmol), alkynoic acid (0.6 mmol), CuI (2 mol %), PPh3 (4 mol %) and K2CO3 (1.0 mmol) were added to a screw-capped test tube. The tube was then evacuated and backfilled with argon (3 cycles). H2O (3 mL) was added by syringe at room temperature. The tube was again evacuated and backfilled with argon (3 cycles). The mixture was heated to 100 C and stirred for 24 h. After cooling to room temperature, the mixture was diluted with water, and the combined aqueous phases were extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4 and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 2731 - 2738
[2]Tetrahedron,2012,vol. 68,p. 6413 - 6419
[3]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6938 - 6942
[4]RSC Advances,2016,vol. 6,p. 71117 - 71121

21
[ 878133-05-2 ]
[ 637-44-5 ]
[ 83515-06-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate; L-proline; copper(I) bromide; In dimethyl sulfoxide; at 100℃; for 3h;Inert atmosphere;	General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4248 - 4252

22
[ 2516-40-7 ]
[ 637-44-5 ]
[ 325793-43-9 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 1644 - 1648

23
[ 480452-05-9 ]
[ 637-44-5 ]
[ 1431960-45-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine; HATU; In tetrahydrofuran; at 25℃; for 12h;	PP-2-2A FC-1 -4A To a stirred solution of phenylpropiolic acid (156 mg, 1 .1 mmol) in THF (2 mL) was added N-(tert-butoxycarbonyl)-2-methyl-1 , 3-diaminopropane (200 mg, 1.1 mmol), HATU (613 mg, 1 .6 mmol) and TEA (0.3 mL). The reaction mixture was stirred at 25 C for 12 hrs. The analysis of LCMS showed completion of reaction and formation of desired product, it was quenched by addition of H20 (20 mL), extracted with EtOAc (2 x 50 mL), the organic layer was washed with H20, brine dried over Na2S04 and concentrated. The residue was purified by column chromatography on silica gel (DCM/MeOH = 10:1 ) to afford the product as a white solid (0.28 g, yield: 82%).

Reference： [1]Patent: WO2013/62945,2013,A1 .Location in patent: Page/Page column 100

24
[ 10531-80-3 ]
[ 637-44-5 ]
[ 14016-00-3 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 9193 - 9196

25
[ 2700-30-3 ]
[ 637-44-5 ]
N,N-diisopropyl-3-phenylpropiolamide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 5737 - 5742

26
[ 42711-75-1 ]
[ 637-44-5 ]
C₁₈H₂₀O [ No CAS ]

Reference： [1]RSC Advances,2013,vol. 3,p. 19264 - 19267

27
[ 10531-80-3 ]
[ 637-44-5 ]
[ 886-66-8 ]
6-methyl-2-(phenylethynyl)benzo[d]oxazole [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 7902 - 7906

28
[ 31739-56-7 ]
[ 119072-55-8 ]
[ 2393-23-9 ]
[ 637-44-5 ]
[ 1604835-53-1 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 2084 - 2091

29
[ 20035-08-9 ]
[ 637-44-5 ]
[ 18723-83-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 2029 - 2039
[2]Journal of Organic Chemistry,2015,vol. 80,p. 7652 - 7657

30
[ 57297-29-7 ]
[ 637-44-5 ]
[ 651043-20-8 ]

Reference： [1]New Journal of Chemistry,2014,vol. 38,p. 3062 - 3070

31
[ 52548-63-7 ]
[ 637-44-5 ]
(Z)-3-benzylidene-6-fluoroisoindolin-1-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 3433 - 3442

32
[ 42055-15-2 ]
[ 637-44-5 ]
N-(3-hydroxypropyl)-N-methyl-3-phenylpropiolamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 418 - 421

33
[ 42142-52-9 ]
[ 637-44-5 ]
N-(3-hydroxy-3-phenylpropyl)-N-methyl-3-phenylpropiolamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 418 - 421

34
[ 42142-52-9 ]
[ 637-44-5 ]
(Z)-5-methyl-2,8-diphenyl-4,5-dihydro-2H-1,5-oxazocen-6(3H)-one [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 418 - 421

35
[ 10531-80-3 ]
[ 637-44-5 ]
6-methyl-2-(phenylethynyl)benzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With 1,3-bis-(diphenylphosphino)propane; palladium dichloride; silver(l) oxide; In benzene; at 60℃; for 12h;	In a V- vial PdCl2 (6.7 mg, 0.03 mmol), dppp (24.7 mg, 0.06 mmol), Ag2O (208.6 mg, 0.9 mmol), phenylpropiolic acid(65.8 mg, 0.45 mmol), <strong>[10531-80-3]6-methylbenzoxazole</strong>(39.9 mg, 0.3 mmol) and then benzene (1.8 mL) was added and the reaction was terminated after stirring for 12 hours at 60C. The temperature of the V- vial was lowered to room temperature, and then extracted with Et2O (3 x 20mL) and washed with saturated aqueous solution of NH4Cl (20 mL). The organic layer was extracted, dried over anhydrous MgSO4 and filtered. After removing the solvent by separation by column chromatography, to give the title compound 6-methyl-2-(phenylethynyl)benzoxazole (51.1 mg, 73%).
68%	With Pd(II)(N-(3-(1-hydroxy-3-phenylpropan-2-yl carbamoyl)benzylidene)-2-methylpropan-2-amineoxide(-2H)); silver(l) oxide; In N,N-dimethyl-formamide; at 80℃;	General procedure: To an oven dried 25 mL round bottom flask, palladium complex (7 mg, 3 mol %), silver(I) oxide (229 mg, 1 mmol) and aryl propiolic acid (1 mmol), under air, were added. Azole substrate (0.5 mmol) in DMF (4 mL) was added to the reaction mixture. The reaction mixture was stirred at 80 C for 6-8 h. The reaction mixture was diluted with EtOAc then filtered through filter paper. The filtrate was quenched with Ice cold water and then, aqueous layer was extracted with EtOAc. The organic phase was washed with NaCl (satd aq), dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

Reference： [1]Patent: KR2015/14210,2015,A .Location in patent: Paragraph 0125-0127
[2]Tetrahedron,2015,vol. 71,p. 1975 - 1981

36
[ 924869-17-0 ]
[ 637-44-5 ]
methyl 2-(phenylethynyl)benzoxazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With Pd(II)(N-(3-(1-hydroxy-3-phenylpropan-2-yl carbamoyl)benzylidene)-2-methylpropan-2-amineoxide(-2H)); silver(l) oxide; In N,N-dimethyl-formamide; at 80℃;	General procedure: To an oven dried 25 mL round bottom flask, palladium complex (7 mg, 3 mol %), silver(I) oxide (229 mg, 1 mmol) and aryl propiolic acid (1 mmol), under air, were added. Azole substrate (0.5 mmol) in DMF (4 mL) was added to the reaction mixture. The reaction mixture was stirred at 80 C for 6-8 h. The reaction mixture was diluted with EtOAc then filtered through filter paper. The filtrate was quenched with Ice cold water and then, aqueous layer was extracted with EtOAc. The organic phase was washed with NaCl (satd aq), dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

Reference： [1]Tetrahedron,2015,vol. 71,p. 1975 - 1981

37
[ 1201-74-7 ]
[ 637-44-5 ]
(R)-N-(1-(naphthalen-2-yl)ethyl)-3-phenylpropiolamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 6708 - 6712

38
[ 894493-95-9 ]
[ 637-44-5 ]
N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3-phenylpropiolamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 6708 - 6712

39
[ 1950-68-1 ]
[ 637-44-5 ]
[ 68668-00-8 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 4697 - 4703

40
[ 29927-08-0 ]
[ 637-44-5 ]
6,7-dimethyl-3-phenyl-4H-benzo[b][1,4]thiazine-4-carbonitrile [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 3122 - 3127

41
[ 5765-65-1 ]
[ 5326-38-5 ]
[ 637-44-5 ]
C₁₉H₁₈N₂O₃ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2222 - 2225

42
[ 1950-68-1 ]
[ 637-44-5 ]
S-(phenylethynyl)-S-(4-methoxyphenyl) sulfone [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2656 - 2659

43
[ 145240-28-4 ]
[ 637-44-5 ]
[ 64357-44-4 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2972 - 2975

44
[ 3260-89-7 ]
[ 637-44-5 ]
C₁₆H₁₃NO₂ [ No CAS ]

Reference： [1]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 1745 - 1746

45
[ 6342-60-5 ]
[ 637-44-5 ]
C₁₆H₁₃NO [ No CAS ]

Reference： [1]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 1745 - 1746

46
[ 2620-50-0 ]
[ 119072-55-8 ]
[ 10111-08-7 ]
[ 637-44-5 ]
1-(benzo[d][1,3]dioxol-5-ylmethyl)-N-(tert-butyl)-2-(1H-imidazol-2-yl)-5-oxo-3-phenyl-2,5-dihydro-1H-pyrrole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium sulfate; In methanol; at 20℃;	General procedure: To a solution of aldehydes (1a-g, 1 equiv) in methanol (3 mL) were added successively Na2SO4 (0.3 g), amines (2a-f, 1.2 equiv), 2-alkynoic acids (3a-d, 1.2 equiv) and isonitriles (4a-e, 1.2 equiv) in a screw capped vial equipped with a magnetic stir bar. The reaction mixture was stirred at room temperature or 50 C for 24-48 hours in closed vial. After completion of the reaction, the mixture was diluted with dichloromethane (50 mL) and was extracted with water (50 mL). Organic layer was washed with brine (50 mL), dried over magnesium sulfate and evaporated under reduced pressure to obtained residue which was subjected to silica gel column chromatography to afford the desired product alpha,beta-unsaturated gamma-lactams (5a-s).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 754 - 756

47
[ 3132-99-8 ]
[ 119072-55-8 ]
[ 136-90-3 ]
[ 637-44-5 ]
C₂₉H₂₉BrN₂O₃ [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1040 - 1043

48
[ 119072-55-8 ]
[ 53903-49-4 ]
[ 104-87-0 ]
[ 637-44-5 ]
C₃₀H₂₉F₃N₂O₃ [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1040 - 1043

49
[ 119072-55-8 ]
[ 458-52-6 ]
[ 104-87-0 ]
[ 637-44-5 ]
C₂₉H₂₉FN₂O₃ [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1040 - 1043

50
[ 54149-64-3 ]
[ 637-44-5 ]
N-[(2-methyl-2-propen-1-yl)oxy]-3-phenylpropynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃; for 3.0h;	General procedure: To a solution of propiolic acid derivatives (1 eq.) in dichloromethane (0.5 M) were added O-allyl hydroxylamine derivatives (1.2 eq.), Et3N (1.2 eq.), 4-(N,N-dimethylamino)pyridine (0.05 eq.), and EDC (1.05 eq.) at 0 C. After being stirred for 3 h at r.t., the reaction mixture was diluted with H2O and extracted with CHCl3 (3 times). The organic phase was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography (Hexane : EtOAc = 3 / 1) to give the corresponding hydroxamate.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1786 - 1789

51
[ 703-12-8 ]
[ 637-44-5 ]
N-((4-bromophenyl)sulfonyl)-N-methyl-3-phenylpropiolamide [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 2280 - 2283

52
[ 637-44-5 ]
[ 13223-25-1 ]
[ 329206-02-2 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 72810 - 72814

53
[ 14542-93-9 ]
[ 10111-08-7 ]
[ 637-44-5 ]
[ 2450-71-7 ]
C₂₅H₃₀N₄O₂ [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 103601 - 103605

54
[ 104-42-7 ]
[ 637-44-5 ]
N-(p-dodecylphenyl)-3-phenylpropiolamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		4-dodecyllaniline(97%, 5.00 g, 19.12 mmol),Phenylpropiolic acid (3.65 g, 24.9 mmol), DMAP (23.4 mg, 0.19 mmol) and 25 mL of THF were added to a 100 mL 1-necked round flask and stirred for 10 minutes at 0 C under a nitrogen atmosphere.EDC (3.86 g, 24.9 mmol) was added and stirred at room temperature for a further 5 hours. After the reaction, the solution was precipitated in 300 mL of a saturated aqueous solution of NH4Cl and stirred for 1 hour to dissolve remaining phenylpropiolic acid, DMAP, EDC, EDC urea salt and THF in an aqueous solution and then filtrate to obtain a mixture of unreacted <strong>[104-42-7]4-dodecylaniline</strong> and the product A precipitate was obtained. The precipitate was dissolved in 100 mL of methylene chloride (MC), 1.0 g of anhydrous magnesium sulfate was added, stirred for 30 minutes, and then filtered to remove a small amount of water mixed with the precipitate. The solvent of the filtered MC solution was evaporated120 mL of n-hexane was further added thereto, and the mixture was stirred for 1 hour and filtered to remove unreacted <strong>[104-42-7]4-dodecylaniline</strong>. The filtered solid product was dried in a vacuum oven for 24 hours to obtain a white, new propiolamide compound DOPPPAM (yield: 80%; Tm: 80 DEG C).

Reference： [1]Patent: KR101679815,2016,B1 .Location in patent: Paragraph 0102-0106

55
[ 622-33-3 ]
[ 637-44-5 ]
[ 22509-60-0 ]

Yield	Reaction Conditions	Operation in experiment
90%		In a clean 25 mL reaction tube0.2 mmol of phenylpropiolic acid and an appropriate amount of dichloromethane were added,Further, 0.22 mmol of N-methyl-N-ethynyl p-toluenesulfonamide was added,Stirred at room temperature for 10 minutes,TLC point plate detection reaction,After the reaction,Further, 0.22 mmol of O-benzylhydroxylamine was added,Stirred at 40 C for 14 hours,TLC point plate detection reaction,After the reaction,After separation and purification by column chromatography,Directly to the pure product,White solid,The yield was 90%.

Reference： [1]Patent: CN106146359,2016,A .Location in patent: Paragraph 0026; 0027

56
[ 452-78-8 ]
[ 637-44-5 ]
4-fluoro-3-methylphenyl 3-phenylpropiolate [ No CAS ]