[ CAS No. 14371-10-9 ] {[proInfo.proName]}

Name: 14371-10-9|(2E)-3-Phenyl-2-propenal|98%
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Quality Control of [ 14371-10-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 14371-10-9 ]

Product Details of [ 14371-10-9 ]

CAS No. :	14371-10-9	MDL No. :	MFCD00007000
Formula :	C₉H₈O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KJPRLNWUNMBNBZ-QPJJXVBHSA-N
M.W :	132.16	Pubchem ID :	637511
Synonyms :	Cinnamaldehyde	Chemical Name :	(2E)-3-Phenyl-2-propenal

Safety of [ 14371-10-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 14371-10-9 ]

* 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 [ 14371-10-9 ]
Downstream synthetic route of [ 14371-10-9 ]

[ 14371-10-9 ] Synthesis Path-Upstream 1~9

1
[ 4407-36-7 ]
[ 14371-10-9 ]
[ 5786-21-0 ]

Reference： [1] Synthesis (Germany), 2013, vol. 45, # 20, p. 2875 - 2887

2
[ 14371-10-9 ]
[ 5443-49-2 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1982, vol. 52, p. 1380 - 1382[2] Zhurnal Obshchei Khimii, 1982, vol. 52, # 7, p. 1563 - 1566
[3] J. Gen. Chem. USSR (Engl. Transl.), 1982, vol. 52, # 4, p. 696 - 702[4] Zhurnal Obshchei Khimii, 1982, vol. 52, # 4, p. 801 - 808
[5] Organic Process Research and Development, 1999, vol. 3, # 6, p. 389 - 393

3
[ 14371-10-9 ]
[ 5443-49-2 ]

Reference： [1] Tetrahedron Letters, 2010, vol. 51, # 20, p. 2708 - 2712

4
[ 14371-10-9 ]
[ 107-91-5 ]
[ 19006-81-6 ]

Reference： [1] Journal of Organic Chemistry, 2002, vol. 67, # 12, p. 4304 - 4308

5
[ 110-89-4 ]
[ 110-86-1 ]
[ 14371-10-9 ]
[ 141-82-2 ]
[ 676551-01-2 ]
[ 1552-94-9 ]

Reference： [1] Journal of the Indian Chemical Society, 1923, vol. 1, p. 301[2] Chem. Zentralbl., 1925, vol. 96, # II, p. 1852

6
[ 14371-10-9 ]
[ 122-51-0 ]
[ 7148-78-9 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 16, p. 8074 - 8082

7
[ 78108-48-2 ]
[ 100-52-7 ]
[ 14371-10-9 ]
[ 26327-98-0 ]
[ 4187-87-5 ]
[ 39850-43-6 ]
[ 100-51-6 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1997, # 12, p. 2820 - 2831

8
[ 4407-36-7 ]
[ 14371-10-9 ]
[ 132539-06-1 ]

Reference： [1] Synthesis (Germany), 2013, vol. 45, # 20, p. 2875 - 2887

9
[ 14371-10-9 ]
[ 143979-44-6 ]

Reference： [1] Chirality, 2012, vol. 24, # 12, p. 1082 - 1091

[ 14371-10-9 ] Synthesis Path-Downstream 1~88

1
[ 14371-10-9 ]
[ 500-98-1 ]
4-(C-phenyl-acetylamino)-1t-phenyl-pentadien-(1.3ξ)-oic acid-(5) [ No CAS ]

Reference： [1]Chemistry of Penicillin,

2
[ 14371-10-9 ]
[ 34801-09-7 ]
[ 102025-08-1 ]

Reference： [1]Chemische Berichte,1957,vol. 90,p. 815,822

3
[ 14371-10-9 ]
[ 5048-82-8 ]
4-trans-cinnamylidenamino-trans-cinnamic acid ethyl ester [ No CAS ]

Reference： [1]Chemische Berichte,1938,vol. 71,p. 501,504, 517

4
[ 14371-10-9 ]
[ 13327-27-0 ]
6,6'-dimethyl-2H,2'H-2,2'-trans-cinnamylidene-bis-pyridazin-3-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1949,p. 1248,1249

5
[ 2346-00-1 ]
[ 14371-10-9 ]
[ 55089-95-7 ]

Reference： [1]Journal of Organic Chemistry,1975,vol. 40,p. 2025 - 2029

6
[ 14371-10-9 ]
[ 67-56-1 ]
[ 59-43-8 ]
[ 28168-52-7 ]

Reference： [1]Chemical and pharmaceutical bulletin,1970,vol. 18,p. 527 - 533

7
[ 14371-10-9 ]
[ 13472-60-1 ]
[ 102830-77-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592
[2]Journal of Medicinal Chemistry,1986,vol. 29,p. 1590 - 1595

8
[ 14371-10-9 ]
[ 1145-81-9 ]
[ 118878-40-3 ]
[ 118878-40-3 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 3109 - 3110
[2]Tetrahedron Letters,1988,vol. 29,p. 3109 - 3110

9
[ 14371-10-9 ]
[ 18880-05-2 ]
[ 82102-27-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1982,p. 273 - 278

10
[ 14371-10-9 ]
[ 14001-67-3 ]
(E)-5-(1-hydroxy-3-phenyl-2-propen-1-yl)-2-methylthiopyrimidine [ No CAS ]

Reference： [1]Acta Chemica Scandinavica,1989,vol. 43,p. 816 - 818

11
[ 14371-10-9 ]
[ 15832-09-4 ]
2-cinnamylidene-6-methoxycoumaran-3-one [ No CAS ]

Reference： [1]Organic Mass Spectrometry,1980,vol. 15,p. 545 - 555

12
[ 14371-10-9 ]
[ 62961-64-2 ]
(4S,5S)-2-((E)-Styryl)-[1,3]dioxolane-4,5-dicarboxylic acid diisopropyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1994,p. 1783 - 1784

13
[ 14371-10-9 ]
[ 5802-17-5 ]
3-cinnamylidene-6-methoxychroman-4-one [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1987,p. 2743 - 2772

14
[ 14371-10-9 ]
[ 3350-30-9 ]
2,9-Dicinnamyliden-cyclononanon [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1968,vol. 46,p. 3685 - 3690

15
[ 14371-10-9 ]
[ 143-33-9 ]
[ 25808-30-4 ]
N-Cyanomethyl-N-((E)-1-cyano-3-phenylprop-2-enyl)methylamine [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2919 - 2923

16
[ 14371-10-9 ]
[ 36878-91-8 ]
[ 41867-20-3 ]
2-Furan-3-yl-6-methyl-4-((E)-styryl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4667 - 4675

17
[ 14371-10-9 ]
[ 41867-20-3 ]
[ 53090-46-3 ]
2-Methyl-4-((E)-styryl)-6-thiophen-3-yl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4667 - 4675

18
[ 14371-10-9 ]
[ 14227-17-9 ]
1-(2,4,6-trimethoxyphenyl)-4-phenyl-1-azabuta-1,3-diene [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,1998,p. 993 - 1007

19
[ 14371-10-9 ]
[ 6972-82-3 ]
[ 343362-39-0 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3440 - 3450

20
[ 14371-10-9 ]
[ 2836-03-5 ]
[ 134833-83-3 ]
(E)-3-(2-Dimethylamino-phenylamino)-5-phenyl-pent-4-enoic acid methoxy-methyl-amide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 2143 - 2150

21
[ 14371-10-9 ]
[ 2836-03-5 ]
[ 96-32-2 ]
(E)-3-(2-Dimethylamino-phenylamino)-5-phenyl-pent-4-enoic acid methyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 2143 - 2150

22
[ 4187-87-5 ]
[ 292638-84-7 ]
[ 14371-10-9 ]
[ 90-63-1 ]

Reference： [1]European Journal of Inorganic Chemistry,2004,p. 810 - 817

23
[ 14371-10-9 ]
[ 2058-72-2 ]
C₁₈H₁₄BrNO₃ [ No CAS ]
C₁₈H₁₄BrNO₃ [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 507 - 509

24
[ 14371-10-9 ]
[ 17640-15-2 ]
[ 100-46-9 ]
[ 5817-70-9 ]
[ 61912-03-6 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 3837 - 3848

25
[ 14371-10-9 ]
[ 15799-79-8 ]
(R)-3-(4-dimethylamino-2-methoxy-phenyl)-3-phenyl-propanol [ No CAS ]
[ 447462-76-2 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 7894 - 7895

26
[ 14371-10-9 ]
[ 15799-79-8 ]
[ 18162-48-6 ]
[ 447462-79-5 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 7894 - 7895

27
[ 14371-10-9 ]
[ 68827-43-0 ]
[ 934733-34-3 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5696 - 5711

28
[ 14371-10-9 ]
[ 614-19-7 ]

Reference： [1]Chemical Communications,2007,p. 849 - 851

29
[ 14371-10-9 ]
(R)-p-mentha-1,5-diene [ No CAS ]
[ 25705-52-6 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 2329 - 2331
[2]Journal of Organic Chemistry,2005,vol. 70,p. 2329 - 2331

30
[ 14371-10-9 ]
Merrifield resin-bound-2,3,5,6-tetrafluorophenyl-ethyl(pentafluoropropyl)phosphonoacetate [ No CAS ]
[ 19163-24-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 4729 - 4742

31
[ 14371-10-9 ]
[ 115016-95-0 ]

Reference： [1]Chemische Berichte,1956,vol. 89,p. 671,675

32
[ 14371-10-9 ]
[ 29678-81-7 ]

Reference： [1]Helvetica Chimica Acta,1954,vol. 37,p. 1634,1656

33
[ 14371-10-9 ]
[ 17852-67-4 ]
4,5-Dihydro-5-phenyl-1-(4-methylsulphonylphenyl)-1H-pyrazol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Table 1 shows some examples that are encompassed by the general formula (I) and in Table 2 the data are indicated for identification of these compounds. The examples 1-36, 44-63 and 65-74 have been prepared according to method A, examples 37-39 according to method B, examples 40-42 according to method C, example 64 according to method F and the enantiomerically pure compounds 75-78 by resolution of the racemic mixture.

Reference： [1]Patent: US6353117,2002,B1 .Location in patent: Page column 17-18

34
[ 14371-10-9 ]
[ 53981-38-7 ]
N-cinnamylidene-4-chromanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
188 g (62%)	In ethanol;	EXAMPLE II N-Cinnamylidene-4 -chromanamine An 80 g (0.54 mole) portion of 4-chromanamine and 700 ml of ethanol were placed in a 2-l, 3-necked flask, equipped with a stirrer and reflux condenser fitted with a drying tube, and treated with 75 g (0.57 mole) of cinnamaldehyde. The reaction mixture was refluxed for 4.5 hrs., filtered hot, refrigerated overnight and filtered. A white crystalline solid was washed with 100 ml of ethanol, ether and dried; m.p. 106-107. Yield: 188 g (62%). The crude product was recrystallized from 460 ml of ethanol (Darco), washed with 100 ml of ethanol, ether, and dried; m.p. 105-106. Yield; 71 g (50%). Anal. Calcd. for C18 H17 NO: C, 82.09; H, 6.51; N, 5.32. Found: C, 81.82; H, 6.47; N, 5.29.

Reference： [1]Patent: US4093799,1978,A

35
[ 14371-10-9 ]
[ 120068-79-3 ]
[ 1022080-72-3 ]
[ 1022080-73-4 ]

Reference： [1]New Journal of Chemistry,2008,vol. 32,p. 472 - 476

36
[ 14371-10-9 ]
[ 64051-79-2 ]
[ 1082074-99-4 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 8829 - 8837

37
[ 14371-10-9 ]
[ 63636-89-5 ]
[ 948844-44-8 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 9125 - 9129
[2]Chemistry - A European Journal,2008,vol. 14,p. 2145 - 2152

38
[ 14371-10-9 ]
[ 57497-39-9 ]
[ 90331-02-5 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 3165 - 3179

39
[ 14371-10-9 ]
[ 138286-76-7 ]
2-Bromo-2-((E)-1-hydroxy-3-phenyl-allyl)-octanoic acid ethyl ester [ No CAS ]

Reference： [1]Synthesis,2009,p. 2634 - 2645

40
[ 14371-10-9 ]
[ 542-92-7 ]
[ 76-05-1 ]
[ 144222-34-4 ]
C₃₅H₃₄N₂O₂S [ No CAS ]
C₃₅H₃₄N₂O₂S [ No CAS ]
C₃₅H₃₄N₂O₂S [ No CAS ]
C₃₅H₃₄N₂O₂S [ No CAS ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 1205 - 1208

41
[ 14371-10-9 ]
[ 3586-14-9 ]
[ 1314802-01-1 ]

Yield	Reaction Conditions	Operation in experiment
72%		General procedure: A solution of aromatic compounds (1 mmol in 3 mL anhydrous THF) at -15 C under nitrogen was added t-BuOK (1.5 equiv.) and n-BuLi (1.5 equiv.), which resulted in formation of a red reaction mixture. After 1 h, cinnamaldehyde (1.5 equiv.) was added dropwise and the mixture was gradually warmed to rt and stirred at rt overnight under nitrogen. The reaction mixture was poured into 40 mL ice water, and extracted three times with diethyl ether. The combined organic extracts were washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography (acetate/petroleum ether: from 1:10 to 1:5) to give the compounds 13a-16a.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3190 - 3200

42
[ 14371-10-9 ]
[ 124755-24-4 ]
C₁₇H₁₇F₆O₅P [ No CAS ]
C₁₇H₁₇F₆O₅P [ No CAS ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 10809 - 10811

43
[ 14371-10-9 ]
[ 29689-63-2 ]
[ 1142923-21-4 ]
ethyl 1-benzyl-6-hydroxy-2-oxo-4-phenylpiperidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; potassium acetate; In 2,2,2-trifluoroethanol; at 20℃;	General procedure: In a round bottom flask, unsaturated aldehyde 2 (0.25 mmol, 1 equiv), amidomalonate 1 (0.3 mmol, 1.2 equiv), catalyst (0.05 mmol, 20% mol), and KOAc (0.3 mmol, 1.2 equiv) were added sequentially in 1 mL of 2,2,2-trifluoroethanol. The reaction was stirred at room temperature overnight. Then the crude was purified by column chromatography to furnish piperidine adducts 3.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8942 - 8950

44
[ 14371-10-9 ]
[ 37674-72-9 ]
C₁₈H₁₅ClO [ No CAS ]
[ 1351524-23-6 ]
[ 1351524-18-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 7357 - 7364

45
[ 14371-10-9 ]
[ 37674-72-9 ]
[ 1315274-76-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With phosphoric acid; at 80℃; for 4h;	General procedure: A mixture of the appropriate chroman-4-one (10 mmol) and trans-cinnamaldehyde (10 mmol) or 3-phenylpropiolaldehyde (10 mmol), in 85% phosphoric acid (63 mL) was heated at 80 C for 4 h while stirring. After cooling the mixture was diluted with ice and water. The precipitate was filtered off, washed with water and crystallized.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 7357 - 7364

46
[ 14371-10-9 ]
[ 1857-19-8 ]
[ 1357917-87-3 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 2149 - 2151

47
[ 14371-10-9 ]
[ 876-31-3 ]
C₁₈H₁₄N₂O [ No CAS ]
C₁₈H₁₄N₂O [ No CAS ]
C₁₈H₁₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 4-nitro-benzoic acid; In methanol; at 20℃; for 24h;	General procedure: An amber 2-dram vial equipped with a magnetic stir bar, containing catalyst II (8 mg, 0.025 mmol), (E)-cinnamaldehyde 2a (33 mg, 0.25 mmol) and 4-nitrobenzoic acid (4 mg, 0.025 mmol) was charged with methanol (0.8 mL) at room temperature. The solution was stirred for 5 min before the addition of methyl 2-(4-nitrophenyl)acetate 1a (56 mg, 0.30 mmol). The resulting mixture was stirred at constant temperature until complete consumption of (E)-cinnamaldehyde 2a was observed as determined by TLC. The resulting mixture was directly purified by silica gel chromatography (30% EtOAc/hexanes) to afford the desired compound 3a as an white solid (major: 38 mg, 46% yield, 96% ee, Rf = 0.33 (EtOAc/hexanes = 1:3, v/v) and as a colorless gum (minor: 32 mg, 40% yield, 96% ee, Rf = 0.24 (EtOAc/hexanes = 1:3, v/v)).

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2809 - 2812

48
[ 14371-10-9 ]
[ 52787-14-1 ]
C₂₀H₂₀O₅ [ No CAS ]
C₂₀H₂₀O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid; In methanol; at 20℃; for 72h;	General procedure: An amber 2-dram vial equipped with a magnetic stir bar, containing catalyst II (8 mg, 0.025 mmol), (E)-cinnamaldehyde 2a (33 mg, 0.25 mmol) and 4-nitrobenzoic acid (4 mg, 0.025 mmol) was charged with methanol (0.8 mL) at room temperature. The solution was stirred for 5 min before the addition of methyl 2-(4-nitrophenyl)acetate 1a (56 mg, 0.30 mmol). The resulting mixture was stirred at constant temperature until complete consumption of (E)-cinnamaldehyde 2a was observed as determined by TLC. The resulting mixture was directly purified by silica gel chromatography (30% EtOAc/hexanes) to afford the desired compound 3a as an white solid (major: 38 mg, 46% yield, 96% ee, Rf = 0.33 (EtOAc/hexanes = 1:3, v/v) and as a colorless gum (minor: 32 mg, 40% yield, 96% ee, Rf = 0.24 (EtOAc/hexanes = 1:3, v/v)).

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2809 - 2812

49
[ 14371-10-9 ]
[ 76469-88-0 ]
C₁₉H₁₇NO₃ [ No CAS ]
C₁₉H₁₇NO₃ [ No CAS ]
C₁₉H₁₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 4-nitro-benzoic acid; In methanol; at 20℃; for 72h;	General procedure: An amber 2-dram vial equipped with a magnetic stir bar, containing catalyst II (8 mg, 0.025 mmol), (E)-cinnamaldehyde 2a (33 mg, 0.25 mmol) and 4-nitrobenzoic acid (4 mg, 0.025 mmol) was charged with methanol (0.8 mL) at room temperature. The solution was stirred for 5 min before the addition of methyl 2-(4-nitrophenyl)acetate 1a (56 mg, 0.30 mmol). The resulting mixture was stirred at constant temperature until complete consumption of (E)-cinnamaldehyde 2a was observed as determined by TLC. The resulting mixture was directly purified by silica gel chromatography (30% EtOAc/hexanes) to afford the desired compound 3a as an white solid (major: 38 mg, 46% yield, 96% ee, Rf = 0.33 (EtOAc/hexanes = 1:3, v/v) and as a colorless gum (minor: 32 mg, 40% yield, 96% ee, Rf = 0.24 (EtOAc/hexanes = 1:3, v/v)).

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2809 - 2812

50
[ 14371-10-9 ]
[ 605-03-8 ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 2627 - 2633
[2]Organic Letters,2016,vol. 18,p. 6300 - 6303

51
[ 14371-10-9 ]
[ 5832-44-0 ]
(S)-4-(3-nitro-pyridin-4-yl)-3-phenyl-butyraldehyde [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 9147 - 9150

52
[ 14371-10-9 ]
[ 893-33-4 ]
[ 175477-55-1 ]

Reference： [1]Helvetica Chimica Acta,2013,vol. 96,p. 1548 - 1559

53
[ 14371-10-9 ]
[ 159217-89-7 ]
[ 1428541-58-5 ]
[ 1428541-59-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-(4-carbethoxyphenyl)urea; palladium diacetate; potassium carbonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; at 100℃; for 16h;	General procedure: An appropriate alkene (1 equiv) was added to an NMP solution (enough solvent to attain an initial concentration ofalkene equal to ca. 0.1M) of aryl iodide (2 equiv), Pd(OAc)2 (1 mol %,delivered as a standard THF solution containing 1 mg/mL of compound),N-(4-carbethoxyphenyl)urea (CEPU, 2 mol %), and K2CO3(2 equiv) in a thick-walled glass reaction tube equipped witha magnetic stirring bar and fitted with a threaded Teflon cap. Thereaction tubewas sealed and immersed in an oil bath maintained at 100 C and stirring was started. After 16 h, the resulting black solution was cooled to rt, diluted with ethyl acetate, and washedsequentially with water and brine solution. The organic phase wasseparated, dried (Na2SO4), and concentrated under reduced pressure(rotary evaporator), and the residue was purified by flashcolumn chromatography. Procedure B using tert-butyl (4-iodophenyl)-carbamate(100 mg, 0.31 mmol), K2CO3 (43 mg, 0.31 mmol), Pd(OAc)2 (0.4 mLof THF solution containing 1 mg/mL Pd(OAc)2, equivalent to 0.4 mgPd(OAc)2), CEPU (0.7 mg), and trans-cinnamaldehyde (20 mL,0.16 mmol), and chromatography with 20% ether in hexanes give 7jas a yellow solid (52 mg, 100%) as a 3:1 (E/Z) mixture
	With p-anisidine urea; palladium diacetate; potassium carbonate; In tetrahydrofuran; at 100℃; for 16h;	General procedure: Procedure C. An appropriate alkene (1 equiv) was added to anNMP solution (enough solvent to attain an initial concentration ofalkene equal to ca. 0.1M) of aryl iodide (2 equiv), Pd(OAc)2 (1 mol %,delivered as a standard THF solution containing 1 mg/mL of compound),N-(4-methoxyphenyl)urea (MPU, 2 mol %), and K2CO3(2 equiv) in a thick-walled glass reaction tube equipped witha magnetic stirring bar and fitted with a threaded Teflon cap. Thereaction tubewas sealed and immersed in an oil bath maintained at100 C and stirring was started. After 16 h, the resulting black solutionwas cooled to rt, diluted with ethyl acetate, and washedsequentially with water and brine solution. The organic phase wasseparated, dried (Na2SO4), and concentrated under reduced pressure(rotary evaporator), and the residue was purified by flashcolumn chromatography. Procedure Cusing tert-butyl (4-iodophenyl)-carbamate (100 mg, 0.31 mmol), K2CO3 (43 mg, 0.31 mmol), Pd(OAc)2 (0.4 mL of THF solution containing1 mg/mL Pd(OAc)2, equivalent to 0.4 mg Pd(OAc)2), MPU(0.5 mg), and trans-cinnamaldehyde (20 mL, 0.16 mmol). Chromatographywith 20% ether in hexanes gave 7j as a yellow solid(44 mg, 85%) in a 2.5:1 (E/Z) mixture; mp 102e105 C. 1H: 9.57 (d,J8.0, min.) and 9.46 (d, J8.0, maj.; 1H), 7.48e7.23 (m, 9H), 6.68(br s) and 6.66 (br s; 1H), 6.58 (d, J8.0, maj.) and 6.55 (d, J8.0,min.; 1H), 1.54 (s, min.) and 1.52 (s, maj.; 9H). 13C: 193.6, 193.5,162.0, 161.8, 152.3, 140.7, 140.0, 139.0, 136.7, 133.9, 131.9, 131.1, 130.7,130.5, 129.7, 129.4, 128.9, 128.6, 128.3, 127.2, 126.0, 118.0, 117.9, 81.1(two peaks), 28.30 (two peaks). IR: 3297, 2978, 1727, 1649, 1589,1519, 1449, 1391, 1366, 1343, 1316, 1231, 1150, 1128, 1050, 1026.APCI-MS: 322.2 (MH, 100%). ESIeHRMS: calcd for C20H22NO3[MH]: 324.1600; found: 324.1602. EA calcd for C20H21NO3 C74.28; H 6.55; N 4.33; found C 74.42; H 6.37; N 4.25.

Reference： [1]Tetrahedron,2013,vol. 69,p. 10139 - 10151
[2]Tetrahedron,2013,vol. 69,p. 10139 - 10151

54
[ 14371-10-9 ]
[ 177492-52-3 ]
C₁₆H₁₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20℃; for 8h;	General procedure: A mixture of the appropriate amine (1M-3M, 2 mmol) and the appropriate aldehyde (2.2 mmol) in ethanol (10 mL) was stirred at room temperature for 8 h.

Reference： [1]Molecules,2014,vol. 19,p. 925 - 939

55
[ 14371-10-9 ]
[ 115306-75-7 ]
[ 1616878-39-7 ]

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 3957 - 3959

56
[ 14371-10-9 ]
[ 88497-27-2 ]
[ 14542-93-9 ]
C₂₂H₂₇BrN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium chloride; In butan-1-ol; at 130℃;Inert atmosphere;	[00268] To a solution of amino-heterocycle derivative (1 eq.) in nBuOH under argon are added successively the aldehyde RzCHO (2.5 eq.), MgC^ (0.04 eq.) and 1,1,3,3-tetramethylbutyl isocyanide (1.15 eq.). The reaction mixture is heated at 130 C from between 3.5 h to overnight, and then concentrated in vacuo. The residue is partitioned between heptane and water, stirred for 15 to 40 min, the biphasic solution is filtered on Celpure P65, and the cake is washed with heptane. The two layers of the filtrate are separated, the organic layer is washed successively with water, an aqueous 1M NaOH and brine, then dried over Na2S04 and concentrated in vacuo to afford the expected amine which is used directly in the next step.

Reference： [1]Patent: WO2014/202458,2014,A1 .Location in patent: Paragraph 00268; 00509

57
[ 14371-10-9 ]
[ 223796-20-1 ]
1-cinnamyl-4-(pyridin-3-yl)-1,4-diazepane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20.0℃;	General procedure: 3.2.25 1-Cinnamyl-4-(pyridin-3-yl)-1,4-diazepane (29) Compound 29 was prepared as described for 28 from a mixture of <strong>[223796-20-1]1-(pyridin-3-yl)-1,4-diazepane</strong> (100 mg, 0.56 mmol), cinnamaldehyde (0.076 mL, 0.56 mmol, 93%), and NaBH(OAc)3 (178 mg, 0.84 mmol). Purification by DCVC (DCM:MeOH:NH3/100:0:0 to 100:2.3:0.3) afforded the product as a yellow oil (90 mg, 55%). 1H NMR (CDCl3, 400 MHz) delta 8.14 (d, 1H, J = 3.0 Hz), 7.94 (dd, 1H, J = 4.8, 1.3 Hz), 7.41-7.36 (m, 2H), 7.35-7.30 (m, 2H), 7.27-7.22 (m, 1H), 7.11 (ddd, 1H, J = 4.0 Hz), 6.95 (ddd, 1H, J = 8.6, 3.2, 1.3 Hz), 6.52 (d, 1H, J = 16.1 Hz), 6.30 (dt, 1H, J = 9.0, 6.5 Hz), 3.61 (t, 2H, J = 4.8 Hz), 3.54 (t, 2H, J = 6.3 Hz), 3.33 (d, 2H, J = 6.3 Hz) 2.91-2.82 (m, 2H), 2.75-2.67 (m, 2H), 2.09-2.00 (m, 2H). 13C NMR (CDCl3, 101 MHz) delta 144.90, 137.30, 136.79, 134.41, 133.02, 128.58 (2C), 127.58, 126.33, 123.54 (2C), 120.59, 117.73, 60.72, 55.14, 54.66, 48.51, 47.67, 27.52. ; To a solution 1-(6-bromopyridin-3-yl)-1,4-diazepane (274 mg, 1.07 mmol) and phenylpropanal (157 mL,1.07 mmol, 90%) in dry DCE (10 mL) was added freshly grindedNaBH(OAc)3 (340 mg, 1.61 mmol). The reaction mixture was stirredovernight at rt. Sat. aq NaHCO3 solution (10 mL) was added to thereaction mixture that was extracted with DCM (2 5 mL). Thecombined organic phases were washed with sat. aq NaHCO3 solution(10 mL), dried (MgSO4), filtered, and evaporated in vacuo. Purificationby DCVC (DCM:MeOH:NH3/100:0:0 to 97.5:2.25:0.25)afforded the product as a yellow oil (362 mg, 90%).

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 425 - 444

58
[ 14371-10-9 ]
[ 223796-20-1 ]
1-cinnamyl-4-(pyridin-3-yl)-1,4-diazepane oxalate [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 425 - 444

59
[ 14371-10-9 ]
[ 22604-07-5 ]
(E)-2-(4-hydroxy-7-methoxynaphthalen-1-yl)-3-phenylacrylaldehyde [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2015,vol. 10,p. 1859 - 1863

60
[ 14371-10-9 ]
[ 3484-18-2 ]
(E)-2-(2-ethyl-1H-indole-3-yl)-3-phenylacrylaldehyde [ No CAS ]
(Z)-2-(2-ethyl-1H-indole-3-yl)-3-phenylacrylaldehyde [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8869 - 8874

61
[ 848821-58-9 ]
[ 14371-10-9 ]
[ 76-05-1 ]
C₂₉H₃₄NOSi⁽¹⁺⁾*C₂F₃O₂^(1-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 12337 - 12346

62
[ 848821-58-9 ]
[ 14371-10-9 ]
[ 7601-90-3 ]
C₂₉H₃₄NOSi⁽¹⁺⁾*ClO₄^(1-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 12337 - 12346

63
[ 14371-10-9 ]
[ 637-04-7 ]
(E)-1-(3-tolyl)-2-((E)-3-phenylallylidene)hydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	In dichloromethane; at 20℃; for 1h;	Cinnamaldehyde (4.0 mmol, 1.0 equiv) was added to a solution of m-tolylhydrazine hydrochloride (4.0 mmol, 1.0 equiv) in CH2Cl2 (5 mL), and the mixture was stirred for 1 h at ambient temperature. The reaction mixture was quenched with 10percent NaOH aq. (10 mL) and extracted with CHCl3 (3 x10 mL). The organic layer was washed with water (10 mL) and brine (10 mL), dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by recrystallization in MeOH/Acetone to give the pure hydrazone 1c.

Reference： [1]Tetrahedron,2016,vol. 72,p. 304 - 311

64
[ 14371-10-9 ]
[ 637-04-7 ]
4-methyl-2-(5-phenylpyrazol-1-yl)phenol [ No CAS ]

Reference： [1]Tetrahedron,2016,vol. 72,p. 304 - 311

65
[ 14371-10-9 ]
[ 2924-16-5 ]
(E)-1-(3-fluorophenyl)-2-((E)-3-phenylallylidene)hydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In dichloromethane; at 20℃; for 1h;	Cinnamaldehyde (4.0 mmol, 1.0 equiv) was added to a solution of <strong>[2924-16-5]m-fluorophenylhydrazine hydrochloride</strong> (4.0 mmol, 1.0 equiv) in CH2Cl2 (5 mL), and the mixture was stirred for 1 h at ambient temperature. The reaction mixture was quenched with 10% NaOH aq. (10 mL) and extracted with CHCl3 (3 x10 mL). The organic layer was washed with sat. NaHCO3 (10 mL) and brine (10 mL), dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by recrystallization in MeOH to give the pure hydrazone 1e.

Reference： [1]Tetrahedron,2016,vol. 72,p. 304 - 311

66
[ 14371-10-9 ]
[ 2924-16-5 ]
1-(3-fluorophenyl)-5-phenylpyrazole [ No CAS ]
4-fluoro-2-(5-phenylpyrazol-1-yl)phenol [ No CAS ]

Reference： [1]Tetrahedron,2016,vol. 72,p. 304 - 311

67
[ 14371-10-9 ]
[ 86847-59-8 ]
N-{3-[(2E)-1-hydroxy-3-phenylprop-2-en-1-yl]pyridin-2-yl}-2,2-dimethylpropanamide [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2016,vol. 99,p. 405 - 410

68
[ 14371-10-9 ]
[ 930-88-1 ]
[ 32559-18-5 ]
rac-methyl (3aS,4S,9aR,9bR)-2-methyl-1,3-dioxo-4-[(E)-styryl]decahydro-9aH-pyrrolo[3,4-a]indolizine-9a-carboxylate [ No CAS ]
C₂₁H₂₄N₂O₄ [ No CAS ]