[ CAS No. 4392-24-9 ] {[proInfo.proName]}

Name: 4392-24-9|(3-Bromo-1-propen-1-yl)benzene|98%
Brand: Ambeed
SKU: A703815
Rating: 94 (30 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 4392-24-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4392-24-9 ]

SDS Specification

Alternatived Products of [ 4392-24-9 ]

Product Details of [ 4392-24-9 ]

CAS No. :	4392-24-9	MDL No. :	MFCD00000245
Formula :	C₉H₉Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RUROFEVDCUGKHD-QPJJXVBHSA-N
M.W :	197.07	Pubchem ID :	5357478
Synonyms :

Calculated chemistry of [ 4392-24-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.11
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.21
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.46
Log Po/w (XLOGP3) :	3.39
Log Po/w (WLOGP) :	2.99
Log Po/w (MLOGP) :	3.62
Log Po/w (SILICOS-IT) :	3.33
Consensus Log Po/w :	3.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.51
Solubility :	0.061 mg/ml ; 0.000309 mol/l
Class :	Soluble
Log S (Ali) :	-3.07
Solubility :	0.168 mg/ml ; 0.000853 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.75
Solubility :	0.0352 mg/ml ; 0.000179 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.35

Safety of [ 4392-24-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 4392-24-9 ]

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

Upstream synthesis route of [ 4392-24-9 ]
Downstream synthetic route of [ 4392-24-9 ]

[ 4392-24-9 ] Synthesis Path-Upstream 1~1

1
[ 90-02-8 ]
[ 4392-24-9 ]
[ 28752-82-1 ]

Reference： [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 16, p. 2359 - 2368

[ 4392-24-9 ] Synthesis Path-Downstream 1~88

1
[ 699-04-7 ]
[ 4392-24-9 ]
cinnamyl-methyl-(4-methyl-benzyl)-amine [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1924,vol. 436,p. 311

2
[ 4344-87-0 ]
[ 4392-24-9 ]
5-cinnamyloxy-3-methylpyrazole [ No CAS ]
4,4-dicinnamyl-3-methyl-2-pyrazolin-5-one [ No CAS ]
4-cinnamyl-5-cinnamyloxy-3-methylpyrazole [ No CAS ]
1,4-dicinnamyl-5-cinnamyloxy-3-methylpyrazole [ No CAS ]

Reference： [1]Tetrahedron,1991,vol. 50,p. 515 - 528

3
[ 354-38-1 ]
[ 4392-24-9 ]
[ 52966-67-3 ]

Reference： [1]Synthetic Communications,1988,vol. 18,p. 791 - 800

4
[ 3743-22-4 ]
[ 4392-24-9 ]
[ 79833-17-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 1981 - 1993

5
[ 98541-64-1 ]
[ 4392-24-9 ]
[ 138423-73-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1991,p. 2885 - 2887

6
[ 113-98-4 ]
[ 4392-24-9 ]
[ 80225-13-4 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 587 - 590

7
[ 102503-23-1 ]
[ 4392-24-9 ]
[ 135679-66-2 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 4591 - 4602

8
[ 96145-98-1 ]
[ 4392-24-9 ]
1-Phenyl-5-((E)-3-phenyl-allyloxy)-3-trifluoromethyl-1H-pyrazole [ No CAS ]

Reference： [1]Heterocycles,1993,vol. 36,p. 1375 - 1380

9
[ 354-38-1 ]
[ 4392-24-9 ]
[ 59428-70-5 ]

Reference： [1]Synthesis,1984,p. 941 - 943

10
[ 329-98-6 ]
[ 4392-24-9 ]
[ 72777-78-7 ]

Reference： [1]Bulletin de la Societe Chimique de France,1992,p. 435 - 439

11
[ 88088-95-3 ]
[ 4392-24-9 ]
[ 130759-76-1 ]

Reference： [1]Synthesis,1990,p. 666 - 669

12
[ 5577-13-9 ]
[ 4392-24-9 ]
[ 32120-97-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 2050 - 2054

13
[ 3034-38-6 ]
[ 4392-24-9 ]
1-cinamyl-5-nitroimidazole [ No CAS ]
1-phenyl-3-(4-nitro-1H-imidazol-1yl)prop-1-ene [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1325 - 1334
[2]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1325 - 1334

14
[ 59865-13-3 ]
[ 4392-24-9 ]
C₇₁H₁₁₉N₁₁O₁₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 187 - 192

15
[ 3010-05-7 ]
[ 4392-24-9 ]
{benzyl-[(2E)-3-phenylprop-2-en-1-yl]-amino}-acetonitrile [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2843 - 2850

16
[ 610-78-6 ]
[ 4392-24-9 ]
1-Chloro-2-nitro-4-((E)-3-phenyl-allyloxy)-benzene [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 7337 - 7340

17
[ 59279-60-6 ]
[ 4392-24-9 ]
(2S,4S)-2-tert-Butoxycarbonylamino-4-((E)-3-phenyl-allyl)-pentanedioic acid dimethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5887 - 5890

18
[ 116861-31-5 ]
[ 4392-24-9 ]
[ 220926-85-2 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 1160 - 1165

19
[ 6940-80-3 ]
[ 4392-24-9 ]
[ 221876-43-3 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1999,vol. 54,p. 87 - 95

20
[ 84773-28-4 ]
[ 4392-24-9 ]
[ 317820-93-2 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 8279 - 8283

21
[ 21483-64-7 ]
[ 4392-24-9 ]
[ 335075-94-0 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 37 - 43

22
[ 75-64-9 ]
[ 4392-24-9 ]
[ 112245-04-2 ]
4-tert-butyl (E)-2(R)-isobutyl-3(S)-(3-phenyl-allyl)succinate tert-butylamine salt [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 7675 - 7683

23
[ 4392-24-9 ]
[ 4869-46-9 ]
5-((1R,2R)-1-Hydroxy-2-phenyl-but-3-enyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 5073 - 5075

24
[ 4455-13-4 ]
[ 4392-24-9 ]
ethyl trans-4-phenyl-2-methylthio-4-pentenoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 7270 - 7274

25
[ 4392-24-9 ]
[ 24155-42-8 ]
[ 47447-59-6 ]

Reference： [1]Medicinal Chemistry Research,1999,vol. 9,p. 162 - 175

26
[ 144978-12-1 ]
[ 4392-24-9 ]
[ 474024-83-4 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4559 - 4570

27
[ 4392-24-9 ]
[ 156939-62-7 ]
[ 249764-06-5 ]
[ 429687-52-5 ]
C₅₁H₅₂N₄O₈ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 12969 - 12971

28
[ 26340-49-8 ]
[ 4392-24-9 ]
2-iodo-1-((E)-3-phenylprop-2-enyl)-1H-indole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 7342 - 7349

29
[ 143394-39-2 ]
[ 4392-24-9 ]
[ 624732-02-1 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 4417 - 4420

30
[ 486-60-2 ]
[ 4392-24-9 ]
E-5-(3-phenyl-2-propenyloxy)psoralen [ No CAS ]

Reference： [1]Molecular Pharmacology,2004,vol. 65,p. 1364 - 1374

31
[ 101-98-4 ]
[ 4392-24-9 ]
N-benzyl-N-(2-hydroxyethyl)-N-[methyl-N-3-phenyprop-(2E)-en-1-yl]ammonium bromide [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4183 - 4185

32
[ 1070-89-9 ]
[ 112741-50-1 ]
[ 4392-24-9 ]
2-Oxo-5,6-diphenyl-3-(3-phenyl-allyl)-morpholine-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; hexane; ethyl acetate;	A. 2-Oxo-5,6-diphenyl-3-(3-phenyl-allyl)-morpholine-4-carboxylic acid To a -78 C. solution of 13.8 g (70.0 mmol) of cinnamyl bromide and 4.94 g (14.0 mmol) of t-butyl-(2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholine carboxylate in 350 mL of anhydrous THF was added 28 mL (28 mmol) of 1 M sodium bistrimethylsilylamide in THF. The mixture was stirred at -78 C. for 1.5 h and then poured into 750 mL of ethyl acetate. The mixture was washed twice with brine, dried over MgSO4 and concentrated to give a yellow oil. The oil was stirred in 150 mL of hexane overnight and the precipitated solid was then collected by filtration to give 3.2 g of 62A as a white solid.

Reference： [1]Patent: US5936089,1999,A

33
[ 118077-15-9 ]
[ 10424-65-4 ]
[ 4392-24-9 ]
(+/-)-α-tert.Butyloxycarbonylamino-3-(4'-chloro-5-(diethoxyphosphinyl)methyl-[1.1'-biphenyl]-3-yl) propanoic acid cinnamyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	c (+-)-alpha-tert.Butyloxycarbonylamino-3-(4'-chloro-5-(diethoxyphosphinyl)methyl-[1.1'-biphenyl]-3 -yl) propanoic acid cinnamyl ester To a solution of 1.05 g of the product of step b) in 5 ml dimethylformamide are added 362 mg <strong>[10424-65-4]tetramethylammonium hydroxide pentahydrate</strong>. The mixture is stirred at room temperature 1 1/2 hours and then treated with 394 mg cinnamyl bromide. The mixture is stirred at room temperature 17 hours. The mixture is diluted with ice/water (about 50 ml) and extracted with diethyl ether. The extracts are washed with 10 ml aqueous 1N KHCO3 solution, dried (Na2 SO4) and evaporated to give the heading compound as an oil.

Reference： [1]Patent: US5162311,1992,A

34
[ 40492-52-2 ]
[ 4392-24-9 ]
[ 108-95-2 ]
6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; ethyl acetate; mineral oil; benzene;	EXAMPLE 1 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran Sodium hydride (0.40 g; 10 mM; 60% in mineral oil) was washed twice with hexane under nitrogen. The sodium hydride was suspended in 15 ml of benzene and <strong>[40492-52-2]5-hydroxy-2,3-dihydrobenzofuran</strong> (1.00 g; 7.37 mM) was added in 20 ml of benzene in one portion. The suspension was stirred at room temperature for 1.5 hours giving a pale blue suspension. Cinnamyl bromide (freshly distilled; b.p.=76-8 at 0.2 torr; 1.58 g; 8.0 mM) was added in 15 ml of benzene. The reaction was then heated to reflux for 3.5 hours. After cooling the reaction mixture was poured into 1N aqueous hydrochloric acid, partitioned and back extracted with ether. The combined organic layers were dried over magnesium sulfate, filtered, and stripped to a brown oil. The crude reaction product was flash chromatographed with 600 ml of 20% ethyl acetate in hexane on a 30 mm by 6" column of silica gel. This chromatography gave a mixture of product and starting phenol which were separated by chromatography on one cartridge in the Waters Prep 500 with 2 gallons of 20% ethyl acetate in hexane and four recycles with peak shaving techniques. The resulting semipurified product was crystallized from benzene/hexane to 0.516 g (28% yield). of 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran. NMR (CDCl3): delta7.0-7.3 (m; 4H); 6.16-6.62 (m; 4H); 4.43 (s; 1H); 4.40 (t (8 Hz); 2H); 3.40 (d(5 Hz); 2H); 3.03 (t(8 Hz); 2H). IR: 3700, 2920, 1610, 1490, 1425, 1140, 981, 870 cm-1 (CHCl3). MS: 252 (M+) (68%); 161 (34%); 148 (100%); 91 (36%).
	In hexane; ethyl acetate; mineral oil; benzene;	EXAMPLE 1 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran Sodium hydride (0.40 g; 10 mM; 60% in mineral oil) was washed twice with hexane under nitrogen. The sodium hydride was suspended in 15 ml of benzene and <strong>[40492-52-2]5-hydroxy-2,3-dihydrobenzofuran</strong> (1.00 g; 7.37 mM) was added in 20 ml of benzene in one portion. The suspension was stirred at room temperature for 1.5 hours giving a pale blue suspension. Cinnamyl bromide (freshly distilled; b.p.=76-8 at 0.2 torr; 1.58 g; 8.0 mM) was added in 15 ml of benzene. The reaction was then heated to reflux for 3.5 hours. After cooling the reaction mixture was poured into 1N aqueous hydrochloric acid, partitioned and back extracted with ether. The combined organic layers were dried over magnesium sulfate, filtered, and stripped to a brown oil. The crude reaction product was flash chromatographed with 600 ml of 20% ethyl acetate in hexane on a 30 mm by 6" column of silica gel. This chromatography gave a mixture of product and starting phenol which were separated by chromatography on one cartridge in the Waters Prep 500 with 2 gallons of 20% ethyl acetate in hexane and four recycles with peak shaving techniques. The resulting semipurified product was crystallized from benzene/hexane to 0.516 g (28% yield).of 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran.

Reference： [1]Patent: US4686235,1987,A
[2]Patent: US4537903,1985,A

35
[ 4392-24-9 ]
[ 6052-68-2 ]
(3RS)-2-[(Cinnamylthio)thiocarbonyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With carbon disulfide; sodium hydroxide; In dimethyl sulfoxide;	EXAMPLE 39 (3RS)-2-[(Cinnamylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid In the same manner as descsribed in Example 32, (3RS)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (2.16 g), 10N NaOH (2 ml), carbon disulfide (912 mg), dimethylsulfoxide (6 ml) and cinnamyl bromide (2.364 g) are reacted and treated. The product is crystallized from ethanol to give the title compound (1.34 g), m.p. 200-202 C. NMR (CDCl3 --DMSO--d6, delta): 6.92-7.50 (m, 9H). Mass (m/e): 258 STR44

Reference： [1]Patent: US4628057,1986,A

36
[ 253-72-5 ]
[ 4392-24-9 ]
5,6,7,8-tetrahydro-6-cinnamyl-1,6-naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	EXAMPLE 7 Preparation of 5,6,7,8-tetrahydro-6-cinnamyl-<strong>[253-72-5]1,6-naphthyridine</strong> (Compound No. 58) A solution of <strong>[253-72-5]1,6-naphthyridine</strong> (13.0 g, 0.1 mol) and cinnamyl bromide (23.6 g, 0.12 mol) in acetonitrile (100 ml) was stirred overnight at room temperature. The precipitated crystals were separated by filtration and washed with a small quantity of ether.

Reference： [1]Patent: US4308273,1981,A

37
[ 108-91-8 ]
[ 4392-24-9 ]
[ 112245-04-2 ]
(E)-2(R)-[1(R)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; citric acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; ethyl acetate;	(i) A solution of 5.19 g of 4-tert-butyl hydrogen 2(R)-isobutylsuccinate in 50 ml of dry tetrahydrofuran was cooled to -78 C. while stirring under nitrogen. 25 ml of a 2M solution of lithium diisopropylamide in tetrahydrofuran was added dropwise and the mixture was stirred at -78 C. for 15 minutes. A solution of 5.55 g of cinnamyl bromide in 25 ml of dry tetrahydrofuran was then added dropwise and the mixture was left to come to room temperature gradually. After stirring overnight the tetrahydrofuran was evaporated and the residue was partitioned between ethyl acetate and 5% citric acid solution. The ethyl acetate layer was washed with two further portions of 5% citric acid solution, water and saturated sodium chloride solution and then dried over anhydrous magnesium sulphate. The solvent was evaporated to give an orange oil. This was dissolved in 100 ml of hexane to which 2.35 g of cyclohexylamine were added. The mixture was left to stand for 2 hours and the solid formed was collected by filtration. The solid was suspended in ethyl acetate and shaken with two portions of 2M sulphuric acid to give a clear solution. The ethyl acetate solution was washed twice with water and then with saturated sodium chloride solution and subsequently dried over anhydrous magnesium sulphate. After evaporation of the solvent there were obtained 6.41 g of (E)-2(R)-[1(R)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid in the form of a pale cream coloured solid.
	With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; tert-butyl methyl ether;	(i) A solution of 253.3 g of 4-tert-butyl hydrogen 2(R)-isobutylsuccinate in 2 l of dry tetrahydrofuran was cooled to -70 C. while stirring under nitrogen. 1.2 l of a 2M solution of lithium diisopropylamide in tetrahydrofuran were added dropwise and the mixture was stirred at -70 C. for 30 minutes. A solution of 282 g of cinnamyl bromide in 2 l of dry tetrahydrofuran was then added dropwise and the mixture was left to come to room temperature gradually. After stirring overnight, the tetrahydrofuran was evaporated and the residue was partitioned between ethyl acetate and 2M hydrochloric acid solution. The ethyl acetate layer was washed with a further portion of 2M hydrochloric acid solution, water and saturated sodium chloride solution and then dried over anhydrous magnesium sulphate. The solvent was evaporated to give a gum-like solid which was suspended in 2 l of hexane. The product was removed by filtration (crop 1: 77.3 g). The hexane solution was treated with 109 g of cyclohexylamine and the mixture was left to stand for 1 hour at room temperature and for 16 hours at 4 C. The solid which formed was collected by filtration and dissolved in 2.5 l of methyl tert.butyl ether and 1.5 l of 2M hydrochloric acid to give a clear solution. The separated organic phase was washed twice with water and saturated sodium chloride solution and subsequently dried over anhydrous magnesium sulphate. After evaporation of the solvent there were obtained 189.8 g of a solid (crop 2). The two crops were combined and dried to give 267.1 g of (E)-2(R)-[1(R)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid in the form of a pale cream colored solid.
	With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; tert-butyl methyl ether;	(i) A solution of 253.3 g of 4-tert-butyl hydrogen 2(R)-isobutylsuccinate in 2 l of dry tetrahydrofuran was cooled to -70 C. while stirring under nitrogen. 1.2 l of a 2M solution of lithium diisopropylamide in tetrahydrofuran were added dropwise and the mixture was stirred at -70 C. for 30 minutes. A solution of 282 g of cinnamyl bromide in 2 l of dry tetrahydrofuran was then added dropwise and the mixture was left to come to room temperature gradually. After stirring overnight the tetrahydrofuran was evaporated and the residue was partitioned between ethyl acetate and 2M hydrochloric acid solution. The ethyl acetate phase was washed with a further portion of 2M hydrochloric acid solution, water and saturated sodium chloride solution and then dried over anhydrous magnesium sulphate. The solvent was evaporated to give a gummy solid. This was suspended in 2 l of hexane and the solid was removed by filtration (crop 1:77.3 g). The hexane solution was treated with 109 g of cyclohexylamine, the mixture was left to stand for 1 hour at room temperature and for 16 hours at 4 C. The solid which formed was collected by filtration and dissolved in 2.5 l of methyl tert.butyl ether and 1.5 l of 2M hydrochloric to give a clear solution. The organic phase was washed twice with water and with saturated sodium chloride solution and subsequently dried over anhydrous magnesium sulphate. After evaporation of the solvent there were obtained 189.8 g of a solid (crop 2).The two crops were united and dried to give 267.1 g of (E)-2(R)-[1(R)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid in the form of a pale cream coloured solid.

Reference： [1]Patent: US6235787,2001,B1
[2]Patent: US6239151,2001,B1
[3]Patent: US6281363,2001,B1

38
[ 108-91-8 ]
[ 4392-24-9 ]
[ 112245-04-2 ]
[ 219614-24-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; tert-butyl methyl ether;	(i) A solution of 253.3 g of 4-tert-butyl hydrogen 2(R)-isobutylsuccinate in 2 l of dry tetrahydrofuran was cooled to -70 C. while stirring under nitrogen. 1.2 l of a 2M solution of lithium diisopropylamide in tetrahydrofuran was added dropwise and the mixture was stirred at -70 C. for 30 minutes. A solution of 282 g of cinnamyl bromide in 2 l of dry tetrahydrofuran was then added dropwise and the mixture was left to come to room temperature gradually. After stirring overnight the tetrahydrofuran was evaporated and the residue was partitioned between ethyl acetate and 2M hydrochloric acid solution. The ethyl acetate layer was washed with a further portion of 2M hydrochloric acid solution, water and saturated sodium chloride solution and then dried over anhydrous magnesium sulphate. The solvent was evaporated to give a gummy solid. This was suspended in 2 1 of hexane and the product was removed by filtration (crop 1:77.3 g). The hexane solution was treated with 109 g of cyclohexylamine and the mixture was left to stand for 1 hour at room temperature and for 16 hours at 4 C. The solid which formed was filtered off and dissolved in 2.5 l of methyl tert.butyl ether and 1.5 1 of 2M hydrochloric to give a clear solution. The organic phase was washed twice with water and with saturated sodium chloride solution and then dried over anhydrous magnesium sulphate. After evaporation of the solvent there were obtained 189.8 g of a solid (crop 2).The two crops were combined and dried to give 267.1 g of (E)-2(R)-[(R)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid in the form of a pale cream coloured solid.

Reference： [1]Patent: US6265446,2001,B1

39
[ 41789-95-1 ]
[ 4392-24-9 ]
C₁₈H₂₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 15h;Product distribution / selectivity;	Example 1 Preparation of (+/-)-8-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt Step A: To a mixture of (3-methoxybenzyl) methylamine (3.02 g, 20 mmol) and cesium carbonate (7.82 g, 24 mmol) in DMF (50 mL) was added cinnamyl bromide (4.47 g, 22 mmol). The reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water and extracted with 1:1 hexanes/ethyl acetate (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated to provide the desired product (3.1 g, 58%): 1H NMR (CDCl3, 500 MHz) delta 7.39-7.37 (m, 2H), 7.32-7.29 (m, 2H), 7.23-7.20 (m, 2H), 6.93-6.91 (m, 2H), 6.81-6.78 (m, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.31 (dt, J=15.9, 6.6 Hz, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.19 (dd, J=6.6, 1.2 Hz, 2H), 2.25 (s, 3H); ESI MS m/z=268 [M+H]+. This crude product was used in the next step without further purification.; Example 2 Preparation of (+/-)-6-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt Step A: To a mixture of (3-methoxybenzyl)methylamine (3.02 g, 20 mmol) and cesium carbonate (7.82 g, 24 mmol) in DMF (50 mL) was added cinnamyl bromide (4.47 g, 22 mmol). The reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water and extracted with 1:1 hexanes/ethyl acetate (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated to provide the desired product (3.1 g, 58%): 1H NMR (CDCl3, 500 MHz) delta 7.39-7.37 (m, 2H), 7.32-7.29 (m, 2H), 7.23-7.20 (m, 2H), 6.93-6.91 (m, 2H), 6.81-6.78 (m, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.31 (dt, J=15.9, 6.6 Hz, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.19 (dd, J=6.6, 1.2 Hz, 2H), 2.25 (s, 3H); ESI MS m/z=268 [M+H]+. This crude product was used in the next step without further purification.

Reference： [1]Patent: US2007/21408,2007,A1 .Location in patent: Page/Page column 54

40
[ 19621-92-2 ]
[ 4392-24-9 ]
[ 1000987-50-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6864 - 6870

41
[ 16800-47-8 ]
[ 148461-14-7 ]
[ 4392-24-9 ]
[W(CO)2Br(CH₂CHCH(C₆H₅))((C₆H₅)2PC₆H₄CNOCH₂CHC₃H₇)] [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1995,vol. 50,p. 361 - 367

42
[ 2645-02-5 ]
[ 4392-24-9 ]
C₁₉H₂₁NO₄S [ No CAS ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 11884 - 11895

43
[ 117976-90-6 ]
[ 4392-24-9 ]
[ 1052003-57-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 802 - 806

44
[ 4392-24-9 ]
[ 148017-28-1 ]
[ 1167988-72-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h;	EXAMPLE 6tert-Butyl cinnamyl(sulfamoyl)carbamate Cinnamyl bromide (2.96 g, 15.0 mmol) was placed in a 100 mL round-bottomed flask together with N,N-dimethylformamide (30 mL), Boc-sulfamide (3.24g, 16.5 mmol), and potassium carbonate (8.3 g, 60 mmol). The resulting mixture was stirred at room temperature for 1 h. The progress of reaction was monitored by TLC analysis on silica gel plates using EtOAc/Heptane (1:1) as eluent. The resulting mixture was filtered to remove the solid carbonate and the filtrate was poured into ice-water (200 mL) and then allowed to stand for 10 min. The product precipitated as a white solid. The solid was collected by filtration, washed with water and air-dried to yield the title compound. The solid was further purified by recrystallization from toluene.mp: 117.6 C.1H NMR (d6-DMSO): delta7.54 (s, 2H), 7.43 (d, J=7.2 Hz, 2H), 7.34 (t, J=7.2 Hz, 2H), 7.25 (t, J=7.2 Hz, 1H), 6.52 (d, J=15.8 Hz, 1H), 6.29 (dt, J1=5.9, J2=15.8 Hz, 1H), 4.32 (d, J=5.9 Hz, 2H), 1.46 (s, 9H)13C NMR (d6-DMSO): delta151.3 (C), 136.3 (C), 131.6 (CH), 128.6 (CH), 127.6 (CH), 126.3 (CH), 125.3 (CH), 82.4 (C), 48.9 (CH2), 27.7 (CH3)Elemental analysis, calculated for C14H20N2O4S: C, 53.83; H, 6.45; N, 8.97; S, 10.26. Found: C, 54.06, H, 6.50, N, 8.82, S, 10.10.

Reference： [1]Patent: US2009/176996,2009,A1 .Location in patent: Page/Page column 15

45
[ 354-38-1 ]
[ 4392-24-9 ]
[ 52966-67-3 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 4751 - 4765

46
[ 304460-78-4 ]
[ 4392-24-9 ]
C₂₀H₂₅NO₃S [ No CAS ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 6886 - 6890

47
[ 570-02-5 ]
[ 4392-24-9 ]
[ 147729-67-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 663 - 666

48
[ 163596-75-6 ]
[ 4392-24-9 ]
[ 1211998-82-1 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 3016 - 3023

49
[ 4392-24-9 ]
[ 40738-83-8 ]
[ 1329116-19-9 ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 2147 - 2157

50
[ 1864-94-4 ]
[ 4392-24-9 ]
[ 101109-98-2 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3100 - 3103

51
[ 20603-00-3 ]
[ 144-62-7 ]
[ 4392-24-9 ]
[ 1387526-26-2 ]

Yield	Reaction Conditions	Operation in experiment
22%		General procedure: Method 2: To obtain target 3, alcohol 1 (1.25 mL, 9.30 mmol) was reacted with 2 (1 g, 9.30 mmol) in the presence of KOH (2.5 equiv, 1.30 g) in DMF (20 mL/g). The reaction mixture was allowed to stir overnight at room temperature. After completion, the crude reaction mixture was dissolved in H2O and extracted with Et2O. The product was then extracted into 6 M HCl from Et2O. The solution was basified to pH 12-13 with 5 M NaOH (aq) and extract with Et2O. The combined organic layers were washed with brine solution and dried over Na2SO4. After removal of the solvent under reduced pressure, the crude product was purified by column chromatography (silica gel, 5% CHCl3/MeOH/1% NH4OH) followed by formation of oxalate salt from ether.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4556 - 4563

52
[ 101-98-4 ]
[ 144-62-7 ]
[ 4392-24-9 ]
[ 1387526-28-4 ]

Yield	Reaction Conditions	Operation in experiment
20%		General procedure: Method 2: To obtain target 3, alcohol 1 (1.25 mL, 9.30 mmol) was reacted with 2 (1 g, 9.30 mmol) in the presence of KOH (2.5 equiv, 1.30 g) in DMF (20 mL/g). The reaction mixture was allowed to stir overnight at room temperature. After completion, the crude reaction mixture was dissolved in H2O and extracted with Et2O. The product was then extracted into 6 M HCl from Et2O. The solution was basified to pH 12-13 with 5 M NaOH (aq) and extract with Et2O. The combined organic layers were washed with brine solution and dried over Na2SO4. After removal of the solvent under reduced pressure, the crude product was purified by column chromatography (silica gel, 5% CHCl3/MeOH/1% NH4OH) followed by formation of oxalate salt from ether.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4556 - 4563

53
[ 96293-19-5 ]
[ 4392-24-9 ]
C₃₆H₃₃N₃NiO₃ [ No CAS ]
{(2S,4E)-5-phenyl-2-{{phenyl{2-{[(1R,2S)-1-(phenylmethyl)pyrrolidin-2-yl-kN]carbonyl}aminokN}phenyl}methylene}amino-kN}pent-4-enoato(2 )-kO}nickel [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2012,vol. 95,p. 2672 - 2679

54
[ 636-93-1 ]
[ 4392-24-9 ]
[ 1372346-65-0 ]

Reference： [1]Heterocycles,2013,vol. 87,p. 1519 - 1536

55
[ 796096-64-5 ]
[ 4392-24-9 ]
[ 1448679-18-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 5h;	To a stirred solution of compound 4a (500 mg, 2.05 mmol) in DMF (8 mL) at 0C was added DIPEA (318 mg, 2.46 mmol) and trans-cinnamyl bromide (444 mg, 2.25 mmol) and the mixture was stirred at RT for 5 h, TLC (PE:EA=2:1) showed that the starting material was consumed. Water (30 mL) was added and the mixture was extracted with EA (20 mL x 2). The layers were separated and the combined organic extracts were washed with water, brine and dried over Na2S04. The solvent was removed in vacuo to give crude 9a (0.8 g) as a yellow oil, which was used directly in the next step. LC-MS (Agilent): Rt 3.11 min; m/z calculated for C20H28N2O4 [M+H]+ 361.2, found [M+H]+ 361.2.

Reference： [1]Patent: WO2013/110134,2013,A1 .Location in patent: Page/Page column 55-56

56
[ 429669-07-8 ]
[ 4392-24-9 ]
[ 1537176-34-3 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 856 - 859

57
[ 626-72-2 ]
[ 4392-24-9 ]
[ 1601474-60-5 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3965 - 3969
Angew. Chem.,2014,vol. 53-126,p. 4046 - 4050

58
[ 4392-24-9 ]
[ 214360-76-6 ]
[ 1616917-75-9 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6695 - 6702

59
[ 4392-24-9 ]
[ 269409-97-4 ]
[ 1616917-76-0 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6695 - 6702

60
[ 1054483-78-1 ]
[ 4392-24-9 ]
[ 1616917-83-9 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6695 - 6702

61
[ 4392-24-9 ]
[ 269409-97-4 ]
[ 23925-16-8 ]
(Z)-3-benzylidene-2,3-dihydrobenzofuran [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6695 - 6702

62
[ 6322-56-1 ]
[ 4392-24-9 ]
(E)-1-(4-(cinnamyloxy)-3-nitrophenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.9%	With potassium carbonate; In acetone; at 60℃; for 17h;	To a solution of l-(4-hydroxy-3-nitrophenyl)ethanone (2 g, 11.04 mmol) in acetone (50 niL) was added potassium carbonate (3.05 g, 22.08 mmol). Then (E -(3- bromoprop-l-en-l-yl)benzene (3.59 mL, 24.29 mmol) was added slowly. The solution turned from clear to orange/yellow suspension. After 16 h, LC-MS indicated small amount of product. Then it was heated at 60 °C for 1 h, started to see more product. It was cooled to RT. The reaction mixture was diluted with water (20 mL). The aqueous layer was further extracted with EtOAc (3x20 mL) and the combined organic extracts were washed with water, brine, dried over MgS04, filtered and concentrated. Trituration with CH2CI2 (10 mL) and Hexanes (50 mL) precipitated out a yellow solid. Filtration and drying under vacuum gave 12A (yellow solid, 2 g, 6.73 mmol, 60.9 percent yield). LC-MS Anal. Calc'd for Ci7H15N04 297.10, did not show parent ion in MS, Tr = 3.33 min (Method A). 'H NMR (400MHZ, CHLOROFORM-d) delta 8.45 (d, J=2.2 Hz, IH), 8.16 (dd, J=8.8, 2.2 Hz, IH), 7.46 - 7.40 (m, 2H), 7.38 - 7.32 (m, 2H), 7.32 - 7.28 (m, IH), 7.22 (d, J=9.0 Hz, IH), 6.82 (d, J=15.8 Hz, IH), 6.39 (dt, J=15.9, 5.7 Hz, IH), 4.95 (dd, J=5.6, 1.4 Hz, 2H), 2.61 (s, 3H)

Reference： [1]Patent: WO2014/150646,2014,A1 .Location in patent: Page/Page column 67

63
[ 91-55-4 ]
[ 4392-24-9 ]
(E)-3-cinnamyl-2,3-dimethyl-3H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With ethylmagnesium bromide; In tetrahydrofuran; at 0 - 20℃; for 22.5h;	To a 0 C solution of 2,3dimethylindole 3a (2.00 g, 0.0138 mol) in THF (60 mL) was added dropwise ethylmagnesium bromide (5.50 mL, 0.0165 mol), after stirring for 10 min, followed by cinnamyl bromide (2.24 mL, 0.0152 mol). The mixture was stirred for 4 h at 0 C, and for 18.5 h at room temperature. The mixture was poured onto saturated NH4Cl aqueous solution (40 mL). The separated aqueous layer was extracted with EtOAc (30 mL x 3). The combined organic extracts were washed with water, brine, dried (MgSO4) and concentrated. Purification of the crude oil by column chromatography (SiO2; eluent: 25% EtOAc/hexane) provided 4b (2.91 g, 80%) as a pink oil.Data for 4b: Rf 0.18 (25% EtOAc/hexane); IR (ATR) 3026, 2210, 1577, 1449, 1376, 966, 733, 695 cm-1; 1H NMR (400 MHz, CDCl3): delta 7.54 (dt, J = 7.6, 0.8 Hz, 1H), 7.34-7.29 (m, 2H), 7.26-7.14 (m, 6H), 6.33 (d, J = 16 Hz, 1H), 5.62 (ddd, J = 16, 8.0, 6.8 Hz, 1H), 2.77 (ddd, J = 14, 6.8, 1.6 Hz, 1H), 2.52(ddd, J = 14, 8.0, 1.2 Hz, 1H), 2.30 (s, 3H), 1.36 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 186.3, 154.1, 143.2, 136.8, 133.0, 128.2, 127.6, 127.1, 125.9, 124.8, 124.0, 121.7, 119.7, 57.5, 40.1, 21.5, 15.8; HRMS (ESI+) Calcd for C19H20N (M+H)+: 262.1596, Found: 262.1594.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 6427 - 6431

64
[ 344-14-9 ]
[ 4392-24-9 ]
C₁₄H₁₅FO₄ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 972 - 975

65
[ 27469-60-9 ]
[ 4392-24-9 ]
[ 27064-95-5 ]

Reference： [1]Molecular Pharmacology,2015,vol. 87,p. 197 - 206

66
[ 258346-69-9 ]
[ 4392-24-9 ]
C₂₀H₁₇F₃O₂ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3314 - 3317

67
[ 258346-69-9 ]
[ 4392-24-9 ]
C₃₇H₃₁F₃O₅ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3314 - 3317

68
[ 633-99-8 ]
[ 4392-24-9 ]
1-chloro-2-[((2E)-3-phenyl-2-propen-1-yl)oxy]naphthalene [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2442 - 2446

69
[ 633-99-8 ]
[ 4392-24-9 ]
[ 110973-39-2 ]
1-(1-phenyl-1-propen-1-yl)-2-naphthol [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2442 - 2446

70
[ 90224-71-8 ]
[ 4392-24-9 ]
8-bromo-7-[((2E)-3-phenyl-2-propen-1-yl)oxy]quinoline [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2442 - 2446

71
[ 771-15-3 ]
[ 4392-24-9 ]
2-bromo-1-[((2E)-3-phenyl-2-propen-1-yl)oxy]naphthalene [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2442 - 2446

72
[ 4392-24-9 ]
[ 501-60-0 ]
[ 27356-46-3 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 5836 - 5839

73
[ 4392-24-9 ]
[ 120737-78-2 ]
tert-butyl 4-cinnamyl-2-methylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In acetonitrile; at 60℃;Inert atmosphere;	[00203] Under a N2 atmosphere tert-butyl 2-methylpiperazine-l-carboxylate (2.0 mmol), (E)-(3-bromoprop-l-en-l-yl)benzene (2.4mmol), K2CO3 (3 mmol) were combined in a vial, CH3CN (2 mL) was added, and the reaction mixture was stirred at 60 C overnight, The crude reaction mixture was diluted with EtOAc and washed with H20 and brine. The organic layer was dried over Na2S04, filtered and condensed. The crude mixture was purified using flash silica gel column chromatography to get the pure product tert-butyl 4-cinnamyl-2- methylpiperazine-l-carboxylate (yield 70%).

Reference： [1]Patent: WO2015/200674,2015,A1 .Location in patent: Paragraph 00203

74
[ 10111-08-7 ]
[ 4392-24-9 ]
1-cinnamyl-1H-imidazole-2-carboxaldehyde [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 9981 - 9984

75
[ 26621-44-3 ]
[ 4392-24-9 ]
1-cinnamyl-3-nitro-1H-pyrazole [ No CAS ]
2-cinnamyl-3-nitro-1H-pyrazole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 8864 - 8872

76
[ 29509-06-6 ]
[ 4392-24-9 ]
(E)-2-isobutyryl-5-phenylpent-4-enenitrile [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7317 - 7320

77
[ 4640-67-9 ]
[ 4392-24-9 ]
(E)-2-(4-fluorobenzoyl)-5-phenylpent-4-enenitrile [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7317 - 7320

78
[ 358751-77-6 ]
[ 4392-24-9 ]
1-cinnamyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 80 - 83

79
[ 4392-24-9 ]
[ 1889-71-0 ]
(4-chlorophenyl)(4-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)methanone [ No CAS ]
(4-chlorophenyl)(4-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)methanone [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 68 - 71

80
[ 4392-24-9 ]
[ 1889-71-0 ]
(E)-1-(4-chlorophenyl)-2,5-diphenylpent-4-en-1-one [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 68 - 71

81
[ 63874-95-3 ]
[ 4392-24-9 ]
(E/Z)-1-benzyl-4-(3-phenyl(2-propenyl))oxy-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%		General procedure: General procedure: To a solution of 4-formyl-1H-1-tritylprazole (8a) (94.6 mg, 0.28 mmol) inCH2Cl2 (6 mL) was added 70% mCPBA (131.8 mg, 0.53 mmol) at 0 C, with stirring. After 5 h,saturated NaHCO3 aq (10 mL) was added to quench the reaction mixture. The mixture was extractedwith CH2Cl2 3 times. Combined organic layer was dried over MgSO4, filtered, and condensedunder reduced pressure to give a crude formate. To an acetone solution of the crude formate (6 mL),20% NaOH aq (4 mL) was added, then the mixture was heated under reflux for 1 h, then crotyl bromide(48 L, 0.42 mmol) was added to the cooled mixture. After stirring for 3 h, saturated NH4Cl aq wasadded to the reaction mixture to quench, the mixture was condensed under reduced pressure, extractedwith CH2Cl2 for 3 times. The combined CH2Cl2 layer was dried over MgSO4, filtered, and condensedunder reduced pressure to give a crude residue, which was purified with flash column chromatography(EtOAc:Hexane = 1:10) to give 4-(2-butenyl)oxy-1H-1-tritylpyrazole (1e) (54.5 mg, 51%).

Reference： [1]Molecules,2018,vol. 23

82
[ 2973-59-3 ]
[ 4392-24-9 ]
C₁₇H₁₅BrO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: NBS (180 mg, 1.0 mmol) was added to a stirred solution of isovanillin (1; 152 mg, 1.0 mmol) in MeCN (10 mL) at r.t. and stirred for 10 min. The mixture was then stirred at reflux for 8 h. The reaction was monitored by TLC until 1 was consumed. Then, K2CO3 (276 mg, 2.0 mmol) was added to a stirred solution of the resulting product in MeCN (10 mL) at r.t. and stirred for 10 min. The corresponding alkyl halide (RX, for 3a-g and 3i-m, 1.2 mmol; 1,6-dibromohexane for 3h, 134 mg, 0.55 mmol) was added at r.t. and the mixture was stirred at reflux for 8 h. The mixture was cooled to r.t., concentrated, and extracted with EtOAc (3 15 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated under reduced pressure to afford the crude product 2. Without further purification, freshly prepared phenylallylboronic pinacol ester (365 mg, 1.5 mmol), Pd(OAc)2 (45 mg, 20 mol %), PPh3 (130 mg, 0.5 mmol), and Na2CO3 (110 mg, 1.0 mmol) were added sequentially to a solution of the bromide 2 in EtOH (15 mL) at r.t. The reaction mixture was stirred at reflux for 8 h (the reaction was monitored by TLC). The mixture was cooled to r.t., concentrated, and extracted with EtOAc (3 15 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated under reduced pressure to afford the crude product. Purification on silica gel (hexanes/EtOAc 8:1 to 4:1) afforded the desired 3a-m.

Reference： [1]Synthesis,2018,vol. 50,p. 3408 - 3419

83
[ 63149-33-7 ]
[ 4392-24-9 ]
8-(cinnamyloxy)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%		General procedure: NaH (0.165 g, 6.9 mmol) was slowly added to a solution of 8-hydroxy-2,3,6,7-tetrahydro-1H,5H-pyrido [3,2,1-ij] quinoline-9-carbaldehyde (1 g, 4.6 mmol) in DMF (10 vol) at 0 C. The mixture was stirred at 0 C for 10 min and then added alkyl halide (1.5 eq, 6.9 mmol) at the same temperature. The reaction mixture was stirred at r.t. for 2 h. When the reaction was complete [TLC (EtOAc:hexane, 1:5)], the mixture was extracted with EtOAc and washed with water. The organic layer was separated, dried over anhydrous Na2SO4 and removed under reduced pressure. The residue obtained was purified by flash column chromatography [silica gel (230-400 mesh; Merck), EtOAc-hexane (1:5)].

Reference： [1]Synthetic Communications,2018,vol. 48,p. 2485 - 2495

84
[ 4392-24-9 ]
[ 175205-82-0 ]
2-cinnamyl-3-(trifluoromethyl)pyridine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 14120 - 14125

85
[ 81107-97-3 ]
[ 4392-24-9 ]
(E)-cinnamyl 2-bromo-4-trifluoromethylphenyl ether [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2020,vol. 15,p. 555 - 559

86
[ 81107-97-3 ]
[ 4392-24-9 ]
(Z)-cinnamyl 2-bromo-4-trifluoromethylphenyl ether [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2020,vol. 15,p. 555 - 559

87
[ 18364-47-1 ]
[ 4392-24-9 ]
N-cinnamyl-N-methylpyridin-3-amine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2020,vol. 362,p. 851 - 857

88
[ 18364-47-1 ]
[ 4392-24-9 ]
3-benzyl-1-methyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2020,vol. 362,p. 851 - 857

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Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 4392-24-9 ] {[proInfo.proName]}

Quality Control of [ 4392-24-9 ]

Related Doc. of [ 4392-24-9 ]

Product Details of [ 4392-24-9 ]

Calculated chemistry of [ 4392-24-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4392-24-9 ]

Application In Synthesis of [ 4392-24-9 ]

[ 4392-24-9 ] Synthesis Path-Upstream 1~1

[ 4392-24-9 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry