[ CAS No. 54107-66-3 ] {[proInfo.proName]}

Name: 54107-66-3|5,7-Dimethoxychroman-4-one|97%
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Quality Control of [ 54107-66-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 54107-66-3 ]

Product Details of [ 54107-66-3 ]

CAS No. :	54107-66-3	MDL No. :	MFCD12079198
Formula :	C₁₁H₁₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XZDATLYQNQGRDB-UHFFFAOYSA-N
M.W :	208.21	Pubchem ID :	12777086
Synonyms :

Calculated chemistry of [ 54107-66-3 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.0
TPSA :	44.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.19
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	0.45
Log Po/w (SILICOS-IT) :	2.38
Consensus Log Po/w :	1.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.13
Solubility :	1.56 mg/ml ; 0.00747 mol/l
Class :	Soluble
Log S (Ali) :	-1.86
Solubility :	2.87 mg/ml ; 0.0138 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.12
Solubility :	0.159 mg/ml ; 0.000762 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.26

Safety of [ 54107-66-3 ]

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

Application In Synthesis of [ 54107-66-3 ]

* 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 [ 54107-66-3 ]
Downstream synthetic route of [ 54107-66-3 ]

[ 54107-66-3 ] Synthesis Path-Upstream 1~8

1
[ 59887-91-1 ]
[ 54107-66-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2098 - 2102
[2] Patent: KR2018/64130, 2018, A, . Location in patent: Paragraph 0196; 0201-0202

2
[ 854678-45-8 ]
[ 54107-66-3 ]

Reference： [1] Structural Chemistry, 2011, vol. 22, # 1, p. 161 - 166
[2] Journal of the Chemical Society, 1936, p. 1834,1837
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983, vol. 22, # 11, p. 1119 - 1121
[4] Natural Product Research, 2012, vol. 26, # 16, p. 1473 - 1482

3
[ 500-99-2 ]
[ 54107-66-3 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983, vol. 22, # 11, p. 1119 - 1121
[2] Journal of the Chemical Society, 1936, p. 1834,1837
[3] Structural Chemistry, 2011, vol. 22, # 1, p. 161 - 166
[4] Natural Product Research, 2012, vol. 26, # 16, p. 1473 - 1482

4
[ 90-24-4 ]
[ 54107-66-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2098 - 2102
[2] Patent: KR2018/64130, 2018, A,

5
[ 621-23-8 ]
[ 54107-66-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2098 - 2102

6
[ 832-58-6 ]
[ 54107-66-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2098 - 2102

7
[ 501428-25-7 ]
[ 54107-66-3 ]

Reference： [1] Australian Journal of Chemistry, 2008, vol. 61, # 2, p. 122 - 130

8
[ 54107-66-3 ]
[ 365564-10-9 ]
[ 855-97-0 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 14, # 2, p. 777 - 784
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 11, p. 2613 - 2616

[ 54107-66-3 ] Synthesis Path-Downstream 1~83

2
[ 54107-66-3 ]
5,7-dimethoxy-chroman-4-one oxime [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1952,vol. 30,p. 224

3
[ 854678-45-8 ]
[ 54107-66-3 ]

Yield	Reaction Conditions	Operation in experiment
77.2%	With PPA; at 100℃; for 2h;	A stirred solution of 3-(3,5-dimethoxyphenoxy)propanoic acid I b1 (2.8 g, 12.44) in PPA (30 g) was heated at 100C for 2h.The reaction mixture was cooled to rt, poured into ice-cold water then extracted with EtOAc (2 x 500 ml). The combined organic layers were washed with a saturated Na2003 solution (500 ml), brine (200 ml) then dried over sodium sulfate. It was concentrated down to give the title compound I b-2 as an off-white solid (2.0 g, 77.2% yield). LCMS [M+H] 209.

Reference： [1]Patent: WO2019/119141,2019,A1 .Location in patent: Paragraph 00221; 00225
[2]Structural Chemistry,2011,vol. 22,p. 161 - 166
[3]Journal of the Chemical Society,1936,p. 1834,1837
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 1119 - 1121
[5]Natural Product Research,2012,vol. 26,p. 1473 - 1482

4
[ 67-56-1 ]
[ 54107-66-3 ]
[ 59887-91-1 ]
[ 82366-84-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 395 - 400
[2]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 395 - 400

5
[ 54107-66-3 ]
[ 63934-48-5 ]
[ 153488-88-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

6
[ 54107-66-3 ]
[ 123-11-5 ]
[ 27181-65-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 899 - 901

7
[ 54107-66-3 ]
[ 59887-91-1 ]
[ 82366-84-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 395 - 400

8
[ 501428-25-7 ]
[ 54107-66-3 ]

Reference： [1]Australian Journal of Chemistry,2008,vol. 61,p. 122 - 130

9
[ 54107-66-3 ]
(R)-5,7-dimethoxy-3-hydroxychroman-4-one [ No CAS ]
(S)-5,7-dimethoxy-3-hydroxychroman-4-one [ No CAS ]

Reference： [1]Australian Journal of Chemistry,2008,vol. 61,p. 122 - 130

10
[ 54107-66-3 ]
[ 26964-35-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

11
[ 54107-66-3 ]
[ 26200-06-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

12
[ 54107-66-3 ]
[ 1162-82-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

13
[ 54107-66-3 ]
[ 21554-70-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

14
[ 54107-66-3 ]
[ 1100-15-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

15
[ 54107-66-3 ]
[ 1100-14-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

16
[ 54107-66-3 ]
5,7-dimethoxy-4'-methylisoflavone [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

17
[ 54107-66-3 ]
5,7-dimethoxy-4'-methylisoflavanone [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

18
[ 54107-66-3 ]
[ 153488-99-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

19
[ 54107-66-3 ]
5,7,2',4',6'-pentamethoxyisoflavone [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

20
[ 54107-66-3 ]
[ 153489-00-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

21
[ 54107-66-3 ]
5,7,2',4',6'-pentamethoxyisoflavanone [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

22
[ 54107-66-3 ]
[ 153489-01-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

23
[ 54107-66-3 ]
[ 153489-02-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

24
[ 54107-66-3 ]
[ 153489-03-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1729 - 1736

25
[ 500-99-2 ]
[ 54107-66-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 1119 - 1121
[2]Journal of the Chemical Society,1936,p. 1834,1837
[3]Structural Chemistry,2011,vol. 22,p. 161 - 166
[4]Natural Product Research,2012,vol. 26,p. 1473 - 1482
[5]Patent: WO2019/119141,2019,A1

26
[ 54107-66-3 ]
[ 99059-10-6 ]

Reference： [1]Journal of the Chemical Society,1956,p. 3600,3606

27
[ 54107-66-3 ]
[ 100397-67-9 ]

Reference： [1]Journal of the Chemical Society,1956,p. 3600,3606

28
[ 54107-66-3 ]
[ 459-57-4 ]
[ 1282041-35-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and 4-fluorobenzaldehyde(23 [mu] L, 0.216 mmol) and para-toluenesulfonic acid(5 mg, 0.02 mmol) was dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours.After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (72 mg, 62% .

Reference： [1]Structural Chemistry,2011,vol. 22,p. 161 - 166
[2]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0251-0253

29
[ 54107-66-3 ]
[ 104-88-1 ]
[ 1282041-34-2 ]

Reference： [1]Structural Chemistry,2011,vol. 22,p. 161 - 166

30
[ 54107-66-3 ]
[ 100-52-7 ]
[ 1282041-32-0 ]

Yield	Reaction Conditions	Operation in experiment
35%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol)And benzaldehyde(15 mg, 0.144 mmol)And para-toluene sulfonic acid(3 mg, 0.014 mmol) was dissolved in benzene (2 mL) at 0 C and reacted under reflux conditions for 12 hours. After lowering the temperature to room temperature, the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (17 mg, 35% .)

Reference： [1]Structural Chemistry,2011,vol. 22,p. 161 - 166
[2]Natural Product Research,2012,vol. 26,p. 1473 - 1482
[3]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0216-0218

31
[ 54107-66-3 ]
[ 123-08-0 ]
[ 1282041-33-1 ]

Yield	Reaction Conditions	Operation in experiment
33%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and 4-hydroxybenzaldehyde(26.4 mg, 0.216 mmol)And para-toluenesulfonic acid (5 mg, 0.02 mmol) were dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (15 mg, 33%) .

Reference： [1]Structural Chemistry,2011,vol. 22,p. 161 - 166
[2]Natural Product Research,2012,vol. 26,p. 1473 - 1482
[3]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0256-0258

32
[ 54107-66-3 ]
[ 123-11-5 ]
[ 27181-65-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol)And 4-methoxybenzaldehyde(26 [mu] L, 0.216 mmol)And para-toluene sulfonic acid(5 mg, 0.02 mmol) was dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours.After cooling to room temperature the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound(26 mg, 55%)..

Reference： [1]Structural Chemistry,2011,vol. 22,p. 161 - 166
[2]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0226-0228

33
[ 54107-66-3 ]
[ 24388-23-6 ]
[ 21392-57-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 14,p. 777 - 784
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2613 - 2616

34
[ 54107-66-3 ]
[ 171364-79-7 ]
[ 5631-70-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 14,p. 777 - 784
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2613 - 2616

35
[ 54107-66-3 ]
[ 365564-10-9 ]
[ 855-97-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 14,p. 777 - 784
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2613 - 2616

36
[ 54107-66-3 ]
C₁₂H₁₇BO₄ [ No CAS ]
[ 90363-40-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2613 - 2616

37
[ 59887-91-1 ]
[ 54107-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium on activated charcoal; In methanol;	The 5,7-dimethoxy-4H-chromen-4-one prepared in the above step 1 was dissolved in anhydrous methanol, Pd / C was added in an amount of 10 mol%, and hydrogenation was carried out to prepare the title compound .

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2098 - 2102
[2]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0196; 0201-0202

38
[ 54107-66-3 ]
C₁₈H₁₆O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2098 - 2102

39
[ 54107-66-3 ]
5,2'-dihydroxy-7-methoxy-3-benzylidenechroman-4-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2098 - 2102

40
[ 54107-66-3 ]
[ 1392217-69-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2098 - 2102

41
[ 54107-66-3 ]
5-hydroxy-3-(2-hydroxybenzyl)-7-methoxychroman-4-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2098 - 2102

42
[ 54107-66-3 ]
2-(ethoxymethoxy)benzaldehyde [ No CAS ]
C₂₁H₂₂O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2098 - 2102

43
[ 621-23-8 ]
[ 54107-66-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2098 - 2102

44
[ 832-58-6 ]
[ 54107-66-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2098 - 2102

45
[ 90-24-4 ]
[ 54107-66-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2098 - 2102
[2]Patent: KR2018/64130,2018,A

46
[ 621-59-0 ]
[ 54107-66-3 ]
(E)-3-(3'-hydroxy-4'-methoxybenzylidene)-5,7-dimethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With toluene-4-sulfonic acid; In benzene; for 12h;Reflux;	The <strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong> prepared in the above step 2(71 mg, 0.34 mmol), 3-hydroxy-4-methoxybenzaldehyde (62 mg, 0.041 mmol) and para-toluenesulfonic acid (7 mg, 0.03 mmol) were dissolved in benzene (2 ml) And reacted for 12 hours. After the reaction mixture was cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography (ethyl acetate: n-hexane = 1: 2)To give the title compound (72 mg, 62%).

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0196; 0204-0205

47
[ 54107-66-3 ]
[ 121-33-5 ]
(E)-3-(4-hydroxy-3-methoxybenzylidene)-5,7-dimethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol)And 4-hydroxy-3-methoxybenzaldehyde (27 mg, 0.173 mmol)And para-toluene sulfonic acid(3 mg, 0.02 mmol) was dissolved in benzene (2 mL) at 0 C and reacted under reflux conditions for 12 hours. After cooling to room temperature the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound(31 mg, 63%).

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0210-0213

48
[ 54107-66-3 ]
[ 939-97-9 ]
(E)-3-(4-tert-butylbenzylidene)-5,7-dimethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol)And 4-tert-butylbenzaldehyde(36 [mu] L, 0.216 mmol)And para-toluene sulfonic acid(5 mg, 0.02 mmol)Was dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours. After cooling to room temperature, the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3)To give the title compound (29 mg, 56%).

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0221-0223

49
[ 54107-66-3 ]
[ 34328-46-6 ]
(E)-3-(4-chloro-3-(trifluoromethyl)benzylidene)-5,7-dimethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and4-Chloro-3-trifluoromethylbenzaldehyde(45 mg, 0.216 mmol) and para-toluenesulfonic acid(5 mg, 0.02 mmol) was dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours. After cooling to room temperature the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound(23 mg, 40%).

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0231-0233

50
[ 120-57-0 ]
[ 54107-66-3 ]
(E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)-5,7-dimethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and piperonal (32 mg, 0.216 mmol)And para-toluenesulfonic acid (5 mg, 0.02 mmol) were dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours. After cooling to room temperature, the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (26 mg, 54% )

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0236-0238

51
[ 54107-66-3 ]
[ 66-77-3 ]
(E)-5,7-dimethoxy-3-(naphthalen-1-ylmethylene)chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and1-naphthalathide (29 [mu] L, 0.216 mmol)And para-toluenesulfonic acid (5 mg, 0.02 mmol) were dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours.After cooling to room temperature, the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (38 mg, 77% .)

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0241-0243

52
[ 54107-66-3 ]
[ 86-81-7 ]
(E)-5,7-dimethoxy-3-(3,4,5-trimethoxybenzylidene)chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and3,4,5-trimethoxybenzaldehyde(43 mg, 0.216 mmol)And para-toluene sulfonic acid(5 mg, 0.02 mmol) was dissolved in benzene (2 ml) at 0C and reacted under reflux conditions for 12 hours.The reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (32 mg, 58% )

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0246-0248

53
[ 54107-66-3 ]
[ 456-48-4 ]
(E)-3-(3-fluorobenzylidene)-5,7-dimethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and 3-fluorobenzaldehyde(23 [mu] L, 0.216 mmol)And para-toluenesulfonic acid (5 mg, 0.02 mmol) were dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours.The reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (21 mg, 47%) .

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0261-0263

54
[ 54221-96-4 ]
[ 54107-66-3 ]
(E)-5,7-dimethoxy-3-((6-methoxypyridin-2-yl)methylene)chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and6-methoxypicolinaldehyde(26 [mu] L, 0.216 mmol)And para-toluenesulfonic acid (5 mg, 0.02 mmol) were dissolved in benzene (2 ml) at 0 ° C and reacted under reflux conditions for 12 hours.After lowering the temperature to room temperature, the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (20 mg, 47percent )

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0266-0268

55
[ 54107-66-3 ]
[ 5527-95-7 ]
(E)-3-(4-chloro-3-fluorobenzylidene)-5,7- Dimethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol)And 4-chloro-3-fluorobenzaldehyde(34 mg, 0.216 mmol) and para-toluenesulfonic acid(5 mg, 0.02 mmol) was dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours.After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (23 mg, 40% )

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0271-0273

56
[ 54107-66-3 ]
[ 120-14-9 ]
(E)-3-(3,4-dimethoxybenzylidene)-5,7-dimethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(50 mg, 0.240 mmol)And 3,4-dimethoxybenzaldehyde(60 mg, 0.360 mmol)And para-toluene sulfonic acid(5 mg, 0.02 mmol) was dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours.After the reaction mixture was cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (49 mg, 57% )

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0276-0278

57
[ 54107-66-3 ]
[ 57848-46-1 ]
(E)-3-(4-bromo-2-fluorobenzylidene)-5,7-dimethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and4-Bromo-2-fluorobenzaldehyde(35.7 mg, 0.216 mmol) And para-toluenesulfonic acid (5 mg, 0.02 mmol) were dissolved in benzene (2 ml) at 0 C and reacted under reflux conditions for 12 hours.After cooling to room temperature, the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (18 mg, 32% .

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0281-0283

58
[ 54107-66-3 ]
[ 830-79-5 ]
(E)-5,7-dimethoxy-3-(2,4,6-trimethoxybenzylidene)chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and 2,4,6-trimethoxybenzaldehyde(34.2 mg, 0.216 mmol) and para-toluenesulfonic acid (5 mg, 0.02 mmol) were dissolved in benzene (2 ml)And allowed to react for 12 hours under reflux conditions.After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (33 mg, 59% )

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0286-0288

59
[ 1121-60-4 ]
[ 54107-66-3 ]
(E)-5,7-dimethoxy-3-(pyridin-2-yl-methylene)chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With toluene-4-sulfonic acid; In benzene; at 0℃; for 12h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(50 mg, 0.240 mmol) and 2-pyridinecarboxaldehyde (34 muL, 0.360 mmol) and para-toluenesulfonic acid (5 mg, 0.02 mmol) were dissolved in benzene (2 mL) at 0 C. and reacted under reflux conditions for 12 hours. After cooling to room temperature, the reaction was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 3) to give the title compound (32 mg, 45%)

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0291-0293

60
[ 500-22-1 ]
[ 54107-66-3 ]
(E)-5,7-dimethoxy-3-(pyridin-3-yl-methylene)chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium hydroxide; In ethanol; water; at 0 - 20℃; for 1h;Reflux;	<strong>[54107-66-3]5,7-dimethoxychroman-4-one</strong>(30 mg, 0.144 mmol) and 3-pyridinecarboxaldehyde(16 muL, 0.216 mmol) was dissolved in ethanol (3 mL), and a 5% aqueous solution of NaOH (0.15 mL) was added at 0 C.After reacting at room temperature for 1 hour, the reaction was concentrated under reduced pressure and the residuePurification via flash column chromatography on silica gel (ethyl acetate: n-hexane = 1: 1) gave the title compound (26 mg, 61%).

Reference： [1]Patent: KR2018/64130,2018,A .Location in patent: Paragraph 0296-0298

61
[ 872-85-5 ]
[ 54107-66-3 ]
(E)-5,7-dimethoxy-3-(pyridin-4-yl-methylene)chroman-4-one [ No CAS ]