[ CAS No. 470-17-7 ] {[proInfo.proName]}

Name: 470-17-7|(3aR,4aS,8aR,9aR)-8a-Methyl-3,5-dimethylenedecahydronaphtho[2,3-b]furan-2(3H)-one|98%
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SKU: A249503
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Quality Control of [ 470-17-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 470-17-7 ]

SDS Specification

Alternatived Products of [ 470-17-7 ]

Product Details of [ 470-17-7 ]

CAS No. :	470-17-7	MDL No. :	MFCD08689940
Formula :	C₁₅H₂₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CVUANYCQTOGILD-QVHKTLOISA-N
M.W :	232.32	Pubchem ID :	73285
Synonyms :	(+)-Isoalantolactone;Isohelenin;NSC 601353;NSC 241036	Chemical Name :	(3aR,4aS,8aR,9aR)-8a-Methyl-3,5-dimethylenedecahydronaphtho[2,3-b]furan-2(3H)-one

Calculated chemistry of [ 470-17-7 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	67.95
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.66
Log Po/w (XLOGP3) :	3.42
Log Po/w (WLOGP) :	3.24
Log Po/w (MLOGP) :	3.35
Log Po/w (SILICOS-IT) :	3.54
Consensus Log Po/w :	3.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.43
Solubility :	0.0853 mg/ml ; 0.000367 mol/l
Class :	Soluble
Log S (Ali) :	-3.65
Solubility :	0.0517 mg/ml ; 0.000223 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.3
Solubility :	0.116 mg/ml ; 0.0005 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.74

Safety of [ 470-17-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 470-17-7 ]

* 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 [ 470-17-7 ]

[ 470-17-7 ] Synthesis Path-Downstream 1~88

1
[ 470-17-7 ]
[ 1856-58-2 ]

Reference： [1]Chemische Berichte,1931,vol. 64,p. 67,69
Journal fuer Praktische Chemie (Leipzig),1933,vol. <2> 136,p. 176,185

2
[ 470-17-7 ]
(11Ξ)-8β-hydroxy-13-nor-eudesm-4(15)-ene-11,12-dicarboxylic acid-11-lactone [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1933,vol. <2> 136,p. 176,179, 187

3
[ 110-91-8 ]
[ 470-17-7 ]
(11Ξ)-8β-hydroxy-13-morpholin-4-yl-eudesm-3-en-12-oic acid lactone [ No CAS ]
[ 67416-70-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1978,vol. 16,p. 191 - 195

4
[ 110-91-8 ]
[ 470-17-7 ]
[ 67416-71-1 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1978,vol. 16,p. 191 - 195

5
[ 470-17-7 ]
[ 99-83-2 ]
[ 107175-69-9 ]

Reference： [1]Liebigs Annalen der Chemie,1987,p. 455 - 458

6
[ 470-17-7 ]
[ 370572-96-6 ]
[ 107175-66-6 ]

Reference： [1]Liebigs Annalen der Chemie,1987,p. 455 - 458

7
[ 470-17-7 ]
[ 17322-82-6 ]
[ 6752-90-5 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 835 - 839

8
[ 470-17-7 ]
[ 99603-72-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With Perbenzoic acid; In dichloromethane; at 20℃; for 3h;	socarpine lactone (1.0 g, 4.3 mmol) was dissolved in dichloromethane (16 mL)Slowly in batchessystemWas added peroxybenzoic acid (1.1 g, 5.2 mmol)Reaction at room temperature for 3 hours,Saturated sodium thiosulfate (16 mL) quenched reaction,Dichloromethane extraction (16 mL x 3),The organic phase was washed with saturated aqueous sodium bicarbonate solution (16 mL)Dried and concentrated,Column chromatography (petroleum ether: ethyl acetate = 20: 1) gave compound 1.2 (white solid, 984 mg, yield 92.0%).
92%	With Perbenzoic acid; In dichloromethane; at 20℃; for 3h;	heteromorphism(1.0 g, 4.3 mmol) was dissolved in dichloromethane(16 mL)Slowly add to the systemInto the benzoic acid(1.1 g, 5.2 mmol), reacted at room temperature for 3 hours, quenched with saturated sodium thiosulfate (16 mL), dichloroThe organic phase was washed with methane (16 mL x 3), saturated aqueous sodium bicarbonate (16 mL), dried and concentrated, and purified by column chromatography (petroleumEther: ethyl acetate = 20: 1) to give compound 1.2 (white solid, 984 mg, yield 92.0%).
92%	With Perbenzoic acid; In dichloromethane; at 20℃; for 3h;	1) <strong>[470-17-7]Isoalantolactone</strong> (1.0 g, 4.3 mmol) was dissolved in dichloromethane (16 mL)Peroxybenzoic acid (1.1 g, 5.2 mmol) was slowly added in portions to the system,Reaction at room temperature for 3 hours,Saturated sodium thiosulfate (16 mL) was quenched with dichloroThe organic phase was extracted with methane (16 mL × 3) and saturated aqueous sodium bicarbonate (16 mL), dried and concentrated.Column chromatography (petroleum ether: ethyl acetate = 20: 1) gave 1.2 as a white solid (984 mg, 92.0% yield).

92%	With Perbenzoic acid; In dichloromethane; at 20℃; for 3h;	1) Isolactone (1.0 g, 4.3 mmol) was dissolved in dichloromethane (16 mL) and slowly added to the system in batches.IntoPeroxybenzoic acid (1.1 g, 5.2 mmol), reacted at room temperature for 3 hours, quenched with saturated sodium thiosulfate (16 mL), extracted with dichloromethane (16 mL x 3), washed with saturated aqueous sodium bicarbonate solution (16 mL) The phases were dried and concentrated by column chromatography (petroleum ether:ethyl acetate=20:1) to give compound 1.2 (white solid, 984 mg, yield 92.0%).
92%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 3h;	<strong>[470-17-7]Isoalantolactone</strong>(1.00 g, 4.30 mmol) was dissolved in CH2Cl2 (16 mL). m-CPBA(890 mg, 5.16 mmol) was added to this solution in batches. Themixture was stirred at room temperature for 3 h. Then the reactionmixture was diluted with 16 mL saturated Na2S2O3 solution,washed with saturated NaHCO3 solution, dried over anhydrousNa2SO4, filtered, and evaporated to afford a crude product, whichwas purified by column chromatography [petroleum etherEtOAc(20: 1)] to obtain compound 5 (white solid, 984 mg, 92%). mp124-126 C. 1H NMR (400 MHz, CDCl3) delta (ppm) 6.03 (s, 1H), 5.48 (d,J 2.2 Hz, 1H), 4.41 (t, J 5.0 Hz, 1H), 2.83 (dt, J 11.6, 5.7 Hz, 1H),2.60 (d, J 4.2 Hz, 1H), 2.48 (t, J 3.1 Hz, 1H), 2.12 (d, J 15.6 Hz,1H), 1.83-1.09 (m, 9H), 0.95-0.70 (m, 4H).13C NMR (100 MHz,CDCl3) delta (ppm) 170.4, 141.8, 120.4, 76.5, 58.5, 50.7, 44.2, 41.9, 41.4,40.4, 35.3, 34.3, 23.1, 20.3, 18.6. HR-MS (ESI) m/z: calcd for C15H20O3Na [M Na] 271.1305, found 271.1307.

Reference： [1]Chemistry of Natural Compounds,2006,vol. 42,p. 400 - 406
[2]Patent: CN106474110,2017,A .Location in patent: Paragraph 0026; 0027; 0028
[3]Patent: CN106474109,2017,A .Location in patent: Paragraph 0027; 0028; 0029
[4]Patent: CN106496243,2017,A .Location in patent: Paragraph 0025; 0028; 0030
[5]Patent: CN106478569,2017,A .Location in patent: Paragraph 0028; 0029; 0030
[6]European Journal of Medicinal Chemistry,2018,vol. 157,p. 229 - 247
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 835 - 839
[8]Phytochemistry,1988,vol. 27,p. 2079 - 2082
[9]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697
[10]Molecules,2013,vol. 18,p. 13061 - 13077

9
[ 123489-82-7 ]
[ 470-17-7 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 5265 - 5272

10
[ 470-17-7 ]
[ 930-69-8 ]
[ 69993-35-7 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6106 - 6113

11
[ 123489-82-7 ]
[ 470-17-7 ]
[ 74513-15-8 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6106 - 6113

12
[ 76886-51-6 ]
[ 470-17-7 ]
[ 1856-58-2 ]
[ 69993-39-1 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6106 - 6113
[2]Journal of Organic Chemistry,1989,vol. 54,p. 6106 - 6113

13
[ 470-17-7 ]
4(15)α-epoxyisoalantolactone [ No CAS ]

Reference： [1]Chemistry of Natural Compounds,1996,vol. 32,p. 869 - 872

14
[ 470-17-7 ]
[ 65-71-4 ]
C₂₀H₂₆N₂O₄ [ No CAS ]
C₂₀H₂₆N₂O₄ [ No CAS ]

Reference： [1]Photochemistry and Photobiology,1999,vol. 69,p. 653 - 657

16
[ 470-17-7 ]
[ 64-17-5 ]
[ 7664-41-7 ]
[ 15356-85-1 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2627

17
[ 470-17-7 ]
[ 64-19-7 ]
platinum [ No CAS ]
[ 58526-58-2 ]

Reference： [1]Helvetica Chimica Acta,1931,vol. 14,p. 397,405

18
[ 470-17-7 ]
[ 141-78-6 ]
platinum [ No CAS ]
[ 58526-58-2 ]

Reference： [1]Helvetica Chimica Acta,1931,vol. 14,p. 397,405

19
[ 123-75-1 ]
[ 470-17-7 ]
(3R,3aR,4aS,8aR,9aR)-8a-Methyl-5-methylene-3-pyrrolidin-1-ylmethyl-decahydro-naphtho[2,3-b]furan-2-one [ No CAS ]