[ CAS No. 37905-02-5 ] {[proInfo.proName]}

Name: 37905-02-5|(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate|98%
Brand: Ambeed
SKU: A1446379
Rating: 92 (25 reviews)

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CAS No. :	37905-02-5	MDL No. :	MFCD31922286
Formula :	C₁₂H₁₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YODDEHYDMMDDCV-NXAIOARDSA-N
M.W :	210.27	Pubchem ID :	10058953
Synonyms :

Calculated chemistry of [ 37905-02-5 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	7
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	60.33
TPSA :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.79
Log Po/w (XLOGP3) :	2.67
Log Po/w (WLOGP) :	2.42
Log Po/w (MLOGP) :	1.98
Log Po/w (SILICOS-IT) :	2.74
Consensus Log Po/w :	2.52

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.36
Solubility :	0.91 mg/ml ; 0.00433 mol/l
Class :	Soluble
Log S (Ali) :	-3.23
Solubility :	0.123 mg/ml ; 0.000585 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.08
Solubility :	1.74 mg/ml ; 0.0083 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.73

Safety of [ 37905-02-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 37905-02-5 ]

* 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 [ 37905-02-5 ]
Downstream synthetic route of [ 37905-02-5 ]

[ 37905-02-5 ] Synthesis Path-Upstream 1~1

1
[ 37905-02-5 ]
[ 13190-97-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769
[7] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769
[9] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 761 - 769

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Yield	Reaction Conditions	Operation in experiment
1.517 g	With sodium tetrahydroborate; ethanol; at 0℃; for 1h;	General procedure: SeO2 (602 mg, 5.43 mmol) was added to a solution of geranyl acetate (Compound 29, 1.0 ml, 4.7 mmol) in EtOH (20 ml) at room temperature, and the mixture was refluxed for one hour. The reaction solution was allowed to warm to room temperature, and was filtered through celite. The filtrate was concentrated, and EtOH (20 ml) was then added to the residue. The mixture was cooled to 0C. NaBH4 (58 mg, 1.5 mmol) was added to this cooled mixture followed by stirring for one hour. A 2 M aqueous HCl solution (2 ml) was added to the reaction solution followed by stirring for 5 minutes. The mixture was then poured into H2O (30 ml). After extraction with EtOAc, the combined organic layer was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was subjected to column chromatography on silica gel (Hexane:EtOAc= 2:1) to yield a partially purified primary alcohol (Compound 30) (1.517 g).
160.0 mg	With sodium tetrahydroborate; In dichloromethane; at 0℃; for 0.5h;Inert atmosphere;	A suspension of selenium dioxide (5.6 mg, 1.0 mmol) tert-butyl hydroperoxide (0.24 mL, 2.5 mmol), salicylic acid (12 mol%, 16.6 mg) in anhydrous dichloromethane (20 mL) was stirred for 20 min at room temperature, and then silica gel (230-400 mesh, 72.0 mg) was added. After 30 min, the geranyl acetate 9 (196.3 mg,1.0 mmol) was slowly added. The mixture was stirred for 26 h, filtered through Celite, and washed with 10% potassium hydroxide and brine. The extract was dried over Na2SO4 and concentrated under vacuum. The resulting dark orange residue was dissolved in 4 mL of ethanol and cooled to 0 C, and sodium borohydride (37.8 mg, 1.0 mmol) was added in several portions. After 30 min, a saturated solution of NH4Cl (5 mL), brine, and ethyl acetate was added. The mixture was extracted with ethyl acetate and once with dichloromethane, dried, and concentrated. The residue was purified by flash chromatography eluting with hexane/AcOEt (9/1, v/v) to give alcohol 10 as a yellow oil (160.0 mg, 75%). 1H NMR (400 MHz, CDCl3): δ (ppm)5.38-5.28 (m, 2H), 4.55 (2H, d, J 7.2), 3.96 (2H, s), 2.28-2.06 (5H,m), 2.05 (3H, s), 1.70 (3H, s), 1.60 (3H, s).

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In methanol; at 20℃; for 4h;	Ground 296 K2CO3 (0.802 g, 5.803 mmol) was added to a solution of aldehyde 31 (2.226 g, 10.59 mmol) in 18 MeOH (50 ml) at room temperature, was stirred for 4 hours. 32 H2O was added to the reaction solution, which was extracted with EtOAc twice then with Et2O once. The combined organic layer was washed with a saturated aqueous NH4Cl solution then with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc = 2:1 to 1:2) to yield the corresponding primary alcohol (1.266 g, 71 %).
42%	With water; potassium hydroxide;	Next, the aldehyde was alkaline-hydrolyzed using potassium hydroxide to obtain an alcohol form (compound represented by (ciii) below) (yield: 42%).

Yield	Reaction Conditions	Operation in experiment
45%; 19%	With selenium(IV) oxide; tert-butyl hydroperoxide; In dichloromethane; at 0℃; for 5h;Inert atmosphere;	General procedure: Starting material (1.00 mmol) was added to a solution of selenium dioxide (44 mg, 0.40 mmol) and t-BuOOH (453 mg, 3.10 mmol) in dichloromethane (5 mL) at 0C. After stirring under nitrogen at 0C for a time t (vide infra), the mixture was diluted with ethyl acetate (15 mL), and washed successively with water (2 x 10 mL), saturated NaHCO3 (10 mL), water (10 mL) and brine (10 mL). The organic layer was then dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (hexanes / ethyl acetate).
	With selenium(IV) oxide; In ethanol; for 1h;Reflux;	SeO2 (4.34 g, 37.9 mmol) was added to a solution of geranyl acetate (Compound 29, 7.7 ml, 36 mmol) in EtOH (20 ml) at room temperature, and the mixture was refluxed for one hour. The reaction solution was allowed to warm to room temperature, and was filtered through celite. The filtrate was concentrated, and the residue was then subjected to column chromatography on silica gel (Hexane:EtOAc = 1:1). The fractions containing alcohol (Compound 30) and aldehyde (Compound 31) were collected. After evaporation of the solvent, the residue was dissolved in Et2O (100 ml). MnO2 (85% purity, 22.5 g, 220 mmol) was added to this solution followed by stirring for 15 hours. The reaction solution was filtered through celite, and the filtrate was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc = 4:1) to yield the aldehyde (Compound 31) (2.142 g, 28%).

Yield	Reaction Conditions	Operation in experiment
100%		Example 9 Preparation of 8-Acetoxy-2,6-dimethyl-octa-2,6-dienoic acid (232a) To a solution of aldehyde 230a (19.5 g, 92.7 mmol) in 300 mL of tert-butyl alcohol was added 2-methyl-2-butene (98.0 mL, 925 mmol). To this was added a solution of sodium dihydrogen phosphate (44.5 g, 371 mmol) in 300 mL of water. Sodium chlorite (33.6 g, 371 mmol) was added in several portions. The resulting mixture was rapidly stirred overnight at room temperature. Ethyl acetate was added and the aqueous layer was acidified to pH 3 by addition of 1 M HCl. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3*200 mL). The combined organic extracts were washed with brine, dried over MgSO4, and reduced to dryness in vacuo. The crude product (27.4 g, 121 mmol, >100% yield) was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ: 6.84 (t of q, J=7.25 Hz, J=1.50 Hz, 1H, =CH), 5.34 (t of q, J=7.00 Hz, J=1.50 Hz, 1H, =CH), 4.56 (d, J=7.00 Hz, 2H, -CH2O-), 2.31 (q, J=7.50 Hz, 2H, -CH2-), 2.15 (t, J=7.50 Hz, 2H, -CH2-), 2.03 (s, 3H, -CH3), 1.81 (s, 3H, -CH3), 1.70 (s, 3H, -CH3). LC/MS (ESI): m/z 249 [M+Na]+.
100%		To a solution of aldehyde 230a (19.5 g, 92.7 mmol) in 300 mL of tert-bxxtyl alcohol was added 2-methyl-2- butene (98.0 mL, 925 mmol). To this was added a solution of sodium dihydrogen phosphate (44.5 g, 371 mmol) in 300 mL of water. Sodium chlorite (33.6 g, 371 mmol) was added in several portions. The resulting mixture was rapidly stirred overnight at room temperature. Ethyl acetate was added and the aqueous layer was acidified to pH 3 by addition of 1 MHCl. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3 x 200 mL). The combined organic extracts were washed with brine, dried over MgSO4, and reduced to dryness in vacuo. The crude product (27.4 g, 121 mmol, > 100 % yield) was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ: 6.84(t of q, J= 7.25 Hz, J= 1.50 Hz, IH, =CH), 5.34 (t of q, J= 7.00 Hz, J= 1.50 Hz, IH, =CH), 4.56 (d, J= 7.00 Hz, 2H, -CH2O-), 2.31 (q, J = 7.50 Hz, 2H5 -CH2-), 2.15 (t, J= 7.50 Hz, 2H, -CH2- ), 2.03 (s, 3H, -CH3), 1.81 (s, 3H, -CH3), 1.70 (s, 3H, -CH3). LC/MS (ESI): m/∑2A9 [M+Naf.

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