[ CAS No. 484-12-8 ] {[proInfo.proName]}

Name: 484-12-8|7-Methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one|98%
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SKU: A141553
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Quality Control of [ 484-12-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 484-12-8 ]

SDS Specification

Alternatived Products of [ 484-12-8 ]

Product Details of [ 484-12-8 ]

CAS No. :	484-12-8	MDL No. :	MFCD00076049
Formula :	C₁₅H₁₆O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MBRLOUHOWLUMFF-UHFFFAOYSA-N
M.W :	244.29	Pubchem ID :	10228
Synonyms :	Osthol;NSC 31868;Ostol;Ostole;7-Methoxy-8-(3-methyl-2-butenyl)coumarin	Chemical Name :	7-Methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Calculated chemistry of [ 484-12-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.27
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	72.7
TPSA :	39.44 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.93
Log Po/w (XLOGP3) :	3.81
Log Po/w (WLOGP) :	3.31
Log Po/w (MLOGP) :	2.63
Log Po/w (SILICOS-IT) :	4.03
Consensus Log Po/w :	3.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.97
Solubility :	0.0263 mg/ml ; 0.000108 mol/l
Class :	Soluble
Log S (Ali) :	-4.33
Solubility :	0.0113 mg/ml ; 0.0000464 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.01
Solubility :	0.00237 mg/ml ; 0.00000968 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.13

Safety of [ 484-12-8 ]

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 [ 484-12-8 ]

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

Downstream synthetic route of [ 484-12-8 ]

[ 484-12-8 ] Synthesis Path-Downstream 1~88

1
[ 484-12-8 ]
[ 2221-66-1 ]

Reference： [1]Molecules,2000,vol. 5,p. 880 - 885
[2]Chemische Berichte,1942,vol. 75,p. 1623,1629

2
[ 484-12-8 ]
[ 6619-22-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7426 - 7428
[2]Justus Liebigs Annalen der Chemie,1932,vol. 495,p. 187,202
[3]Chemische Berichte,1934,vol. 67,p. 262
[4]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[5]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4042 - 4049

3
[ 484-12-8 ]
[ 181303-71-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20℃; under 760.051 Torr; for 16h;	To a solution of 1 (8.00 g, 32.79 mmol) in EtOAc (250 mL) was added 10% Pd-C (1.60 g). The resulting solution was stirred under atmospheric H2 at RT overnight. After filtration through celite pad, the EtOAc was removed in vacuo. The residue purified by silica gel chromatography (EtOAc: n-Hexane=1:8) to give 2a (7.32 g, 92 %) as a colorless liquid. IR (KBr) 1722, 1605, 1498, 1433, 1279, 1251, 1159, 1123, 1089, 1030 cm-1. 1H NMR (500 MHz, CDCl3): delta 6.95 (d, J=8.4 Hz, 1H), 6.60 (d, J=8.4 Hz, 1H), 3.82 (s, 3H), 2.92 (t, J=6.7 Hz, 2H), 2.73 (m, 1H), 2.69 (m, 1H), 1.58 (m, 2H), 1.37 (m, 2H), 0.95 (s, 3H), 0.94 (s, 3H). ESI-MS m/z: 249.2 (M+H)+.

Reference： [1]ChemMedChem,2010,vol. 5,p. 598 - 607
[2]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4042 - 4049
[3]Chemische Berichte,1933,vol. 66,p. 754,759

4
[ 484-12-8 ]
8-(2,3-dibromo-3-methyl-butyl)-7-methoxy-coumarin [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]Journal of the American Pharmaceutical Association. (Practical pharmacy edition),1950,vol. 39,p. 107 - 107

5
[ 484-12-8 ]
[ 854642-99-2 ]

Reference： [1]Chemische Berichte,1938,vol. 71,p. 1662,1664

6
[ 484-12-8 ]
[ 489-53-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -5℃; for 2h;	To a solution of osthol 1 (1 eq.) DCM (7 mL) was addedand kept under chilled condition (-5C). To this, mchloroperoxybenzoicacid (mCPBA) (1.2 eq.) dissolved inDCM was added drop wise and the suspension was stirredfor 2 hours. Progress of reaction was monitored using TLCat regular intervals. The product was extracted with (DCM)(3x30 mL) and the combined organic layer was dried oversodium sulphate and purified through column chromatographyto give pure product 6 in 93% yields. Mp: 121C, 1HNMR (CDCl3, 400 MHz): delta 1.28 (6H, s), 3.0 (2H, d, J= 5.8Hz), 3.19 (1H, dd, J= 6.03 & 8.06 Hz), 3.93 (3H, s), 6.25(1H, d, J= 9.2 Hz), 6.88 (1H, d J=8.4 Hz), 7.37 (1H, d, J=8.26 Hz), 7.65 (1H, d, J= 9.3 Hz). 13C NMR (CDCl3, 100MHz): delta 19.14, 22.5, 24.76, 56.16, 59.29, 62.99, 107.43,112.99, 113.15, 114.27, 127.7, 143.7, 153.45, 160.75,161.01. IR (KBr) numaxcm-1: 2924, 1731, 1607, 1384, 1280,1252. HR-ESIMS m/z: calcd for C15H16O4 [M + H] +260.2851, found 260.2849.

Reference： [1]Medicinal Chemistry,2019,vol. 15,p. 138 - 149
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[3]Chemische Berichte,1942,vol. 75,p. 1623,1629
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 664 - 666

7
[ 484-12-8 ]
[ 75-03-6 ]
[ 73490-52-5 ]

Reference： [1]Synthetic Communications,1980,vol. 10,p. 37 - 42
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 472 - 474

8
[ 484-12-8 ]
[ 75-03-6 ]
[ 84385-12-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 472 - 474

9
[ 484-12-8 ]
[ 100-66-3 ]
[ 35129-52-3 ]
[ 75787-27-8 ]
[ 75787-26-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 341 - 345

10
[ 484-12-8 ]
[ 77-78-1 ]
[ 88053-61-6 ]

Reference： [1]Phytochemistry,1983,vol. 22,p. 1836 - 1837

11
[ 484-12-8 ]
[ 74-88-4 ]
[ 73490-51-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 1 (2.44 g, 10 mmol) and KOH (4.20 g, 75 mmol) dissolved in EtOH (100 ml) was added MeI (2.51 ml, 40 mmol) dropwise and then heated to 90 C. for 24 h. The mixture was diluted with dis-H2O (100 ml), acidified with IN HCl to pH 3-4 and then extracted with EtOAc (50 ml×3). The combined EtOAc layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel (EtOAc:n-Hexane=6:1) to obtain 7. 1H-NMR (500 MHz, CDCl3): delta 7.62 (1H, d, J=8.6 Hz), 7.23 (1H, d, J=12.5 Hz), 6.64 (1H, d, J=8.7 Hz), 5.92 (1H, d, J=12.5 Hz), 5.17 (1H, t, J=6.3 Hz), 3.84 (3H, s), 3.71 (3H, s), 3.34 (2H, d, J=6.7 Hz), 1.77 (3H, s), 1.67 (3H, s).
		(Z)-2,4-Dimethoxy-3-prenyl cinamate (7); To a solution of 1 (2.44 g, 10 mmol) and KOH (4.20 g, 75 mmol) dissolved in EtOH (100 ml) was added Mel (2.51 ml, 40 mmol) dropwise and then heated to 90 C for 24 h. The mixture was diluted with dis-H2O (100 ml), acidified with 1N HCl to pH 3-4 and then extracted with EtOAc (50 ml x 3). The combined EtOAc layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel (EtOAc : n-Hexane= 6: 1) to obtain 7.; 1H-NMR (500 MHz, CDCl3): delta7.62 (1H, d, J=8.6 Hz), 7.23 (1H, d, J=12.5 Hz), 6.64 (1H, d, J=8.7 Hz), 5.92 (1H, d, J=12.5 Hz), 5.17 (1H, t, J=6.3 Hz), 3.84 (3H, s), 3.71 (3H, s), 3.34 (2H, d, J=6.7 Hz), 1.77 (3H, s), 1.67 (3H, s).

Reference： [1]Synthetic Communications,1980,vol. 10,p. 37 - 42
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 472 - 474
[3]Patent: US2010/256401,2010,A1 .Location in patent: Page/Page column 14
[4]Patent: EP2236503,2010,A1 .Location in patent: Page/Page column 30

12
[ 484-12-8 ]
[ 74-88-4 ]
[ 84385-11-5 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 472 - 474

13
[ 484-12-8 ]
[ 73292-92-9 ]
[ 73292-93-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 21 - 25

14
[ 484-12-8 ]
[ 51559-35-4 ]

Reference： [1]Phytochemistry,1989,vol. 28,p. 227 - 230

15
[ 484-12-8 ]
[ 35129-52-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 341 - 345
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[3]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[4]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4042 - 4049

16
[ 484-12-8 ]
[ 124555-68-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 664 - 666

17
[ 484-12-8 ]
[ 124555-69-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 664 - 666

18
[ 484-12-8 ]
[ 121994-13-6 ]
[ 109741-39-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 819 - 820

19
[ 484-12-8 ]
[ 74994-81-3 ]
[ 74994-82-4 ]

Reference： [1]Chemistry of Natural Compounds,1980,vol. 16,p. 122 - 124
Khimiya Prirodnykh Soedinenii,1980,vol. 16,p. 165 - 168

20
[ 484-12-8 ]
[ 5673-37-0 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4920 - 4923
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794

21
[ 484-12-8 ]
8-(3-Methyl-butyl)-chromen-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794

22
[ 484-12-8 ]
8-isopentyl-7-hydroxy-chroman-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4042 - 4049

23
[ 484-12-8 ]
7-Ethoxy-8-(3-methyl-butyl)-chromen-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794

24
[ 484-12-8 ]
8-(3-Methyl-butyl)-7-propoxy-chromen-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794

25
[ 484-12-8 ]
7-Butoxy-8-(3-methyl-butyl)-chromen-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794

26
[ 484-12-8 ]
Acetic acid 8-(3-methyl-butyl)-2-oxo-2H-chromen-7-yl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794

27
[ 484-12-8 ]
7-Heptyloxy-8-(3-methyl-butyl)-chromen-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794

28
[ 484-12-8 ]
Butyric acid 8-(3-methyl-butyl)-2-oxo-2H-chromen-7-yl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794

29
[ 484-12-8 ]
Trifluoro-methanesulfonic acid 8-(3-methyl-butyl)-2-oxo-2H-chromen-7-yl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1791 - 1794

30
[ 484-12-8 ]
[ 88053-62-7 ]

Reference： [1]Phytochemistry,1983,vol. 22,p. 1836 - 1837

31
[ 484-12-8 ]
2,4-dimethyoxy-3-γ,γ-dimethylallyl-trans-cinnamoylpiperidide [ No CAS ]

Reference： [1]Phytochemistry,1983,vol. 22,p. 1836 - 1837

32
[ 484-12-8 ]
[ 109741-38-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 819 - 820

33
[ 484-12-8 ]
[ 109741-39-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 819 - 820

34
[ 484-12-8 ]
[ 53004-79-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 21 - 25
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 21 - 25

35
[ 484-12-8 ]
[ 113375-03-4 ]

36
[ 484-12-8 ]
[ 73292-93-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 21 - 25

37
[ 484-12-8 ]
[ 75787-28-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 341 - 345

38
[ 484-12-8 ]
8-(2-amino-3-hydroxy-3-methylbutyl)-7-methoxycoumarin [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 664 - 666

39
[ 673-22-3 ]
[ 484-12-8 ]

Reference： [1]Chemische Berichte,1934,vol. 67,p. 264
[2]Organic Process Research and Development,2019,vol. 23,p. 1669 - 1673

40
[ 484-12-8 ]
7-methoxy-8-(3-methyl-3-phenyl-butyl)-coumarin [ No CAS ]

Reference： [1]Chemische Berichte,1938,vol. 71,p. 1662,1664

41
[ 484-12-8 ]
7-hydroxy-8-(3-methyl-3-phenyl-butyl)-chroman-2-one [ No CAS ]

Reference： [1]Chemische Berichte,1938,vol. 71,p. 1662,1664

42
[ 484-12-8 ]
[ 1143-71-1 ]

Reference： [1]Chemische Berichte,1942,vol. 75,p. 1623,1629

43
[ 484-12-8 ]
[ 865-47-4 ]
[ 100-44-7 ]
[ 1246953-06-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 20℃; for 6h;Inert atmosphere;	To the mixture ofl (2 g, 8.20 mmol) and potassium t-butoxide (1.84 g, 16.4 mmol) in dry DMF (20 mL) was added various benzyl chlorides (16.4 mmol), the resulting solution was stirred at room temperature under nitrogen for 6 h and then diluted with EtOAc (50 mL), washed with dis-H2O (25 mL×3) and dried over Na2SO4. After removal of EtOAC under reduced pressure, the residue was purified by silica gel (EtOAc:n-Hexane=1:101:1) to give 2.2h can be prepared by a similar procedure with reaction temperature of 90 C.(Z)-2-Benzoxy-3-prenyl-4-methoxy-t-butylcinamate (2a)1H-NMR (500 MHz, CDCl3): delta 7.50 (1H, d, J=8.7 Hz), 7.43-7.32 (5H, m), 7.06 (1H, d, J=12.4 Hz), 6.67 (1H, d, J=8.7 Hz), 5.82 (1H, d, J=12.4 Hz), 5.15 (1H, t, J=6.5 Hz), 4.82 (2H, s), 3.84 (3H, s), 3.35 (2H, d, J=6.7 Hz), 1.70 (3H, s), 1.65 (3H, s), 1.44 (9H, s). (cis)
	In N,N-dimethyl-formamide; at 20℃; for 6h;Inert atmosphere;	General procedure for the preparation of 2; To the mixture of 1 (2 g, 8.20 mmol) and potassium t-butoxide (1.84 g, 16.4 mmol) in dry DMF (20 mL) was added various benzyl chlorides (16.4 mmol), the resulting solution was stirred at room temperature under nitrogen for 6h and then diluted with EtOAc (50 mL), washed with dis-H2O (25 mL x3) and dried over Na2SO4. After removal of EtOAC under reduced pressure, the residue was purified by silica gel (EtOAc: n-Hexane=1:10~1:1) to give 2. (Z)-2-Benzoxy-3-prenyl-4-methoxy- t-butylcinamate (2a); 1H-NMR (500 MHz, CDCl3): delta7.50 (1H, d, J=8.7 Hz), 7.43-7.32 (5H, m), 7.06 (1H, d, J=12.4 Hz), 6.67 (1H, d, J=8.7 Hz), 5.82 (1H, d, J=12.4 Hz), 5.15 (1H, t, J=6.5 5 Hz), 4.82 (2H, s), 3.84 (3H, s), 3.35 (2H, d, J=6.7 Hz), 1.70 (3H, s), 1.65 (3H, s), 1.44 (9H, s). (cis)

Reference： [1]Patent: US2010/256401,2010,A1 .Location in patent: Page/Page column 9-10
[2]Patent: EP2236503,2010,A1 .Location in patent: Page/Page column 21-22

44
[ 484-12-8 ]
[ 141-52-6 ]
[ 1246953-21-8 ]

Yield	Reaction Conditions	Operation in experiment
		To the solution of 1 (2.40 g, 10 mmol) in dry EtOH (20 mL) was added the mixture of sodium ethoxide (1.36 g, 20 mmol) in dry EtOH (20 mL) dropwise, the resulting solution was heated under nitrogen for 6 h and then diluted with dis-H2O (50 mL), acidified with 1N HCl(aq) to pH 4-5, extracted with EtOAc (50 mL×3) and dried over Na2SO4. After removal of EtOAc under reduced pressure, the residue was purified by silica gel (EtOAc:n-Hexane=10:1) to give 13. 1H-NMR (500 MHz, CDCl3): delta 7.92 (1H, d, J=16.1 Hz), 7.33 (1H, d, J=8.7 Hz), 6.49 (1H, d, J=8.7 Hz), 6.44 (1H, d, J=16.1 Hz), 6.10 (1H, s), 5.20 (1H, t, J=7.0 Hz), 4.23 (2H, q, J=7.2 Hz), 3.82 (3H, s), 3.42 (1H, d, J=7.1 Hz), 1.82 (3H, s), 1.75 (3H, s), 1.31 (3H, t, J=7.2 Hz). (trans)

Reference： [1]Patent: US2010/256401,2010,A1 .Location in patent: Page/Page column 16-17

45
[ 484-12-8 ]
[ 100-11-8 ]
2-(4-nitrobenzoxy)-4-methoxy-3-prenyl-4-nitrobenzyl cinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In N,N-dimethyl-formamide; at 20℃; for 6h;Inert atmosphere;	To the mixture of 1 (2 g, 8.20 mmol) and potassium t-butoxide (1.84 g, 16.4 mmol) in dry DMF (20 mL) were added various benzyl chlorides (16.4 mmol), and the resulting solution was stirred at room temperature under nitrogen for 6 h and then diluted with EtOAc (50 mL), washed with dis-H2O (25 mL×3) and dried over Na2SO4. After removal of EtOAC under reduced pressure, the residue was purified by silica gel (EtOAc:n-Hexane=1:101:1) to give the title compound: 1H-NMR (400 MHz, CDCl3) 8.24-8.22 (4H, m), 7.59-7.46 (4H, m), 7.45 (1H, d, J=8.6 Hz), 6.98 (1H, d, J=12.3 Hz), 6.69 (1H, d, J=8.6 Hz), 5.81 (1H, d, J=12.3 Hz), 5.12 (1H, t, J=6.5 Hz), 4.91 (2H, s), 4.64 (2H, s), 3.85 (3H, s), 3.32 (2H, d, J=6.6 Hz), 1.61 (3H, s), 1.57 (3H, s).

Reference： [1]Patent: US2010/256401,2010,A1 .Location in patent: Page/Page column 27

46
[ 484-12-8 ]
[ 64-17-5 ]
[ 141-52-6 ]
[ 1246953-21-8 ]

Yield	Reaction Conditions	Operation in experiment
		(E) 2-Hydroxy-3-prenyl-4-methoxy-ethyl cinnamate (13); To the solution of 1 (2.40 g, 10 mmol) in dry EtOH (20 mL) was added the mixture of sodium ethoxide (1.36 g, 20 mmol) in dry EtOH (20 mL) dropwise, the resulting solution was heated under nitrogen for 6h and then diluted with dis-H2O (50 mL), acidified with 1N HCl(aq) to pH 4-5, extracted with EtOAc (50 mL x 3) and dried over Na2SO4. After removal of EtOAc under reduced pressure, the residue was purified by silica gel (EtOAc: n-Hexane=10:1) to give 13. [Show Image] 1H-NMR (500 MHz, CDCl3): delta7.92 (1H, d, J=16.1 Hz), 7.33 (1H, d, J=8.7 Hz), 6.49 (1H, d, J=8.7 Hz), 6.44 (1H, d, J=16.1 Hz), 6.10 (1H, s), 5.20 (1H, t, J=7.0 Hz), 4.23 (2H, q, J=7.2Hz), 3.82 (3H, s), 3.42 (1H, d, J=7.1 Hz), 1.82 (3H, s), 1.75 (3H, s), 1.31 (3H, t, J=7.2 Hz). (trans)

Reference： [1]Patent: EP2236503,2010,A1 .Location in patent: Page/Page column 34-35

47
[ 484-12-8 ]
[ 100-14-1 ]
4-nitrobenzyl (E)-2-(4-nitrobenzoxy)-4-methoxy-3-prenyl-cinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In N,N-dimethyl-formamide; at 20℃; for 6h;Inert atmosphere;	Example 1 Preparation of 2-(4-Nitrobenzoxy)-4-methoxy-3-prenyl-4-nitrobenzyl cinnamate; To the mixture of 1 (2 g, 8.20 mmol) and potassium t-butoxide (1.84 g, 16.4 mmol) in dry DMF (20 mL) were added various benzyl chlorides (16.4 mmol), and the resulting solution was stirred at room temperature under nitrogen for 6 h and then diluted with EtOAc (50 mL), washed with dis-H2O (25 mL x3) and dried over Na2SO4. After removal of EtOAC under reduced pressure, the residue was purified by silica gel (EtOAc: n-Hexane=1:10?1:1) to give the title compound: 1H-NMR (400 MHz, CDCl3) 8.24-8.22 (4H, m), 7.59-7.46 (4H, m), 7.45 (1H, d, J=8.6 Hz), 6.98 (1H, d, J=12.3 Hz), 6.69 (1H, d, J=8.6 Hz), 5.81 (1H, d, J=12.3 Hz), 5.12 (1H, t, J=6.5 Hz), 4.91 (2H, s), 4.64 (2H, s), 3.85 (3H, s), 3.32 (2H, d, J=6.6 Hz), 1.61 (3H, s), 1.57 (3H, s).

Reference： [1]Patent: EP2236503,2010,A1 .Location in patent: Page/Page column 52

48
[ 484-12-8 ]
[ 77-78-1 ]
(Z)-2,4-dimethoxy-3-isopentenyl-cinnamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.4%		2. A Preparation of I-b Compound:The scientific name of compound I-b: (Z)-2, 4-dimethoxy-3-isopentenyl-cinnamic acid.; Install an electric blender and reflux condenser in a dry, clean 1000 ml flask having three openings, add the Osthol 60 g with 700 ml 20% sodium hydroxide aqueous solution, stir the above solution, heat reflux for 0.5 hours, then cool down to room temperature, drop dimethyl sulfate 50 ml into the solution, stir the solution for 1 hour at room temperature, then add 20% sodium hydroxide 200 ml and dimethyl sulfate 50 ml at the same time, stir the above solution for 0.5 hours at room temperature, and then heat refluxed for 2 hours, cool down to room temperature, then adjust the pH value to 23 with 1 mol/L hydrochloric acid, filter the above solution, so that a white crystalline-like powder 41 g is obtained from 50% ethanol recrystallization and vacuum dry at 40 C., wherein the white crystalline-like powder yield is 55.4% and mp is 7072.5 C. Elemental analysis: theoretical value (%): C 69.54 H 7.30 O 23.16 actual value (%): C 70.39 H 6.96 O 22.65 1H-NMR (400 MHz, CDCl3) delta 11.1 (1H, s, COOH), 7.888.0 (2H, d, J=8.8 Hz, -CHCH-COOH), 6.166.82 (2H, d, 3.73 (6H, d, J=7.2 Hz, 2-OCH3), 1.72 (6H, dt, 2CH3).MS: m/z (M++Na) 299, M+: 276 (100%), M+1: 277 (17.7%).

Reference： [1]Patent: US2011/28758,2011,A1 .Location in patent: Page/Page column 3

49
[ 484-12-8 ]
[ 77-78-1 ]
(E)-2,4-dimethoxy-3-isopentenyl-cinnamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.2%		3. A Preparation of I-c Compound:The scientific name of compound I-c: (E)-2, 4-dimethoxy-3-isopentenyl-cinnamic acid.; Install an electric blender and reflux condenser in a dry, clean 500 ml flask having three openings, add the Osthol 20 g with 250 ml 40% sodium hydroxide aqueous solution, stir and dissolve the above solution, drop dimethyl sulfate 30 ml into the solution, stir the solution for 1 hour at room temperature, then add 40% sodium hydroxide 100 ml and dimethyl sulfate 20 ml at the same time, stir the above solution for 0.5 hours at room temperature, and then heat refluxed for 2 hours, cool down to room temperature, then adjust the pH value to 23 with 1 mol/L hydrochloric acid, filter the above solution, so that a white crystalline-like powder 11 g is obtained from 50% ethanol recrystallization and vacuum dry at 60 C., wherein the white crystalline-like powder yield is 52.2% and mp is 6566 C. Elemental analysis: theoretical value (%): C 69.54 H 7.30 O 23.16 actual value (%): C 68.89 H 7.52 O 23.5 1H-NMR (400 MHz, CDCl3) delta 11.1 (1H, s, COOH), 7.888.0 (2H, d, J=15.5 Hz, -CHCH-COOH), 6.166.82 (2H, d, 3.73 (6H, d, J=7.2 Hz, 2-OCH3), 1.72 (6H, dt, 2CH3).MS: m/z (M++Na) 299, M+: 276 (100%), M+1: 277 (17.7%).

Reference： [1]Patent: US2011/28758,2011,A1 .Location in patent: Page/Page column 4

50
[ 484-12-8 ]
[ 77-78-1 ]
2,4-dimethoxy-3-isopentenyl-cinnamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31.25%		4. A Preparation of I-d Compound:The scientific name of compound I-d: 2,4-dimethoxy-3-isopentenyl-cinnamic acid (E:Z=1:1).; Install an electric blender and reflux condenser in a dry, clean 500 ml flask having three openings, add the Osthol 30 g with 250 ml 30% sodium hydroxide aqueous solution, stir and dissolve the above solution, heat reflux for 1 hour, cool down to room temperature, drop dimethyl sulfate 40 ml into the solution, stir the solution for 1 hour at room temperature, then add 30% sodium hydroxide 100 ml and dimethyl sulfate 40 ml at the same time, stir the above solution for 1 hours at room temperature, and then heat refluxed for 1 hours, cool down to room temperature, then adjust the pH value to 23 with 1 mol/L hydrochloric acid, filter the above solution, so that a white crystalline-like powder 12.5 g is obtained from 60% ethanol recrystallization and vacuum dry at 60 C., wherein the white crystalline-like powder yield is 31.25% and mp is 9697 C. Elemental analysis: theoretical value (%): C 39.54 H 7.30 O 23.16 actual value (%): C 70.12 H 7.62 O 22.26 1H-NMR (400 MHz, CDCl3) delta 11.1 (1H, s, COOH), 7.888.0 (2H, d, J=11.6 Hz, -CHCH-COOH), 6.166.82 (2H, d, 3.733.75 (6H, d, J=7.2 Hz, 2-OCH3), 1.72 (6H, dt, 2CH3).MS: m/z (M++Na) 299, M+: 276 (100%), M+1: 277 (17.7%).

Reference： [1]Patent: US2011/28758,2011,A1 .Location in patent: Page/Page column 4

51
[ 484-12-8 ]
(E)-2-hydroxy-4-methoxy-3-isopentenyl-cinnamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.7%		1. A Preparation of I-a Compound:The scientific name of compound I-a: (E)-2-hydroxy-4-methoxy-3-isopentenyl-cinnamic acid.; Install an electric blender and reflux condenser in a dry, clean 500 ml flask having three openings, add an Osthol 50 g with 300 ml 60% sodium hydroxide aqueous solution, stir the above solution, heat reflux for 8 hours to complete the reaction, then cool down to room temperature, adjust pH value to 23 with 1 mol/L hydrochloric acid, filter the above solution, recrystallize the obtained crystal from the above filtration with 70% ethanol 450 ml, and vacuum dry at 50 C. to obtain a light yellow crystalline powder 36 g, wherein the light yellow crystalline powder yield is 65.7% and mp (melting point) is 9293 C. Elemental analysis: theoretical value (%): C 68.68 H 6.92 O 24.40 actual value (%): C 69.45 H 6.86 O 23.69 1H-NMR (400 MHz, CDCl3) delta 11.1 (1H, s, COOH), 7.898.0 (2H, d, J=8.8 Hz, -CHCH-COOH), 6.176.85 (2H, d, 5.1 (1H, s, OH), 3.74 (3H, d, J=7.2 Hz, OCH3), 1.72 (6H, dt, 2CH3).MS: m/z (M++Na) 285, M+: 262.10 (100%), M+1: 263.10 (16.5%).

Reference： [1]Patent: US2011/28758,2011,A1 .Location in patent: Page/Page column 3

52
[ 484-12-8 ]
[ 1663-39-4 ]
[ 1299490-72-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4697 - 4702

53
[ 484-12-8 ]
ethyl 5-(3,4-dihydro-8-isopentyl-2-oxo-2H-chromen-7-yloxy)pentanoate [ No CAS ]