[ CAS No. 16777-87-0 ] {[proInfo.proName]}

Name: 16777-87-0|3,3-Diethoxy-1-propanol|98%
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SKU: A382476
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Quality Control of [ 16777-87-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 16777-87-0 ]

SDS Specification

Alternatived Products of [ 16777-87-0 ]

Product Details of [ 16777-87-0 ]

CAS No. :	16777-87-0	MDL No. :	MFCD00074850
Formula :	C₇H₁₆O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ASERXEZXVIJBRO-UHFFFAOYSA-N
M.W :	148.20	Pubchem ID :	140135
Synonyms :

Calculated chemistry of [ 16777-87-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	6
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.09
TPSA :	38.69 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) :	-6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.24
Log Po/w (XLOGP3) :	0.5
Log Po/w (WLOGP) :	0.77
Log Po/w (MLOGP) :	0.48
Log Po/w (SILICOS-IT) :	0.81
Consensus Log Po/w :	0.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.68
Solubility :	31.1 mg/ml ; 0.21 mol/l
Class :	Very soluble
Log S (Ali) :	-0.88
Solubility :	19.4 mg/ml ; 0.131 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.21
Solubility :	9.18 mg/ml ; 0.0619 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.47

Safety of [ 16777-87-0 ]

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

Application In Synthesis of [ 16777-87-0 ]

* 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 [ 16777-87-0 ]
Downstream synthetic route of [ 16777-87-0 ]

[ 16777-87-0 ] Synthesis Path-Upstream 1~6

1
[ 10601-80-6 ]
[ 16777-87-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 10 - 20℃; for 1 h; Stage #2: With water In tetrahydrofuran for 2 h;	In the following, tetrahydrofuran (THF) to be used was dehydrated on molecular sieves of 4 angstrom overnight. Inside of a 5 L four-neck flask was substituted with nitrogen gas and 2.2 kg of THF was placed therein, followed by cooling to 10° C. or lower. Then, 50 g of lithium aluminum hydride was placed therein and 250 g of ethyl 3,3-diethoxypropionate was added dropwise so that inner temperature did not exceed 10° C. After completion of the dropwise addition, temperature was elevated to 20° C. and reaction was carried out for 1 hour. After the reaction, 420 g of distilled water was added and the whole was stirred for 2 hours, then filtration was performed through No. 2 filtration paper, and subsequently a cake was washed with 1.1 kg of THF. The filtrate was concentrated at 40° C. to obtain 213 g of crude 3,3-diethoxy-1-propanol (hereinafter 33DEP).Then, 200 g of crude 33DEP was placed in a 5 L four-neck flask and 1 kg of hexane was added thereto, followed by stirring for 1 hour (step (A)). After 1 kg of a 0.1M phosphate buffer (pH 7.5) was added and the whole was stirred for 20 minutes, it was transferred to a 5 L separatory funnel and allowed to stand until it was separated into layers. After an aqueous layer was taken out, a hexane layer was returned to the 5 L four-neck flask and 1 kg of the 0.1M phosphate buffer (pH 7.5) was again added. After stirring for 20 minutes, the whole was again transferred to the 5 L separatory funnel and allowed to stand until it was separated into layers and then an aqueous layer was recovered. The aqueous layer was recovered into the 5 L four-neck flask (step (B)). Then, 2 kg of chloroform was added thereto and, after stirring for 30 minutes, the whole was transferred to the 5 L separatory funnel and allowed to stand for 15 minutes to separate it into layers. A chloroform layer was recovered and an aqueous layer was returned to the 5 L four-neck flask and the same operations were performed with 2 kg of chloroform to recover a chloroform layer (step (C)). Then, the recovered chloroform layer was concentrated at 40° C. using an evaporator and, after evaporation ceased, the solvent was evaporated by bubbling with a minute amount of nitrogen. Thereafter, the product was stirred with 20 g of molecular sieves of 4 angstrom for 5 hours and then filtration was performed to obtain 188 g of 33DEP.Then, 150 g of 33DEP obtained by the above operations was placed in a 300 ml four-neck flask and distillation was started under reduced pressure. A first fraction begun to be distilled at a degree of vacuum of 0.4 kPa, a bath temperature of 38° C., an inner temperature of 36° C., and a column top temperature of 33° C. After the distillation ceased, the bath temperature was gradually elevated and a main fraction begun to be distilled at a degree of vacuum of 0.2 kPa, a bath temperature of 58° C., an inner temperature of 55° C., and a column top temperature of 54° C. Thereafter, distillation was performed so that the column top temperature did not exceed 60° C. to obtain 138 g of the main fraction (step (D)). GC analysis was performed for the obtained main fraction. Results are shown in Table 1.

Reference： [1] Patent: US2012/277477, 2012, A1, . Location in patent: Page/Page column 5
[2] Acta Chemica Scandinavica (1947-1973), 1973, vol. 27, p. 239 - 250
[3] Patent: US4634773, 1987, A,

2
[ 78314-63-3 ]
[ 16777-87-0 ]

Reference： [1] Tetrahedron Asymmetry, 1994, vol. 5, # 1, p. 101 - 110
[2] Journal of the Chemical Society, Chemical Communications, 1991, # 20, p. 1421 - 1422

3
[ 2134-29-4 ]
[ 122-51-0 ]
[ 16777-87-0 ]

Reference： [1] Journal of Medicinal Chemistry, 1975, vol. 18, p. 376 - 383

4
[ 35573-93-4 ]
[ 16777-87-0 ]

Reference： [1] Chemische Berichte, 1900, vol. 33, p. 2763
[2] Journal of the Chemical Society, 1941, p. 406

5
[ 3054-95-3 ]
[ 16777-87-0 ]

Reference： [1] Tetrahedron, 1992, vol. 48, # 10, p. 1895 - 1910
[2] Journal of Organic Chemistry, 1981, vol. 46, # 20, p. 3978 - 3988
[3] Journal of Organic Chemistry, 1981, vol. 46, # 20, p. 3978 - 3988

6
[ 3054-95-3 ]
[ 16777-87-0 ]
[ 1569-02-4 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 20, p. 3978 - 3988

[ 16777-87-0 ] Synthesis Path-Downstream 1~88

1
[ 16777-87-0 ]
[ 131543-46-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1910,vol. 374,p. 320

2
[ 16777-87-0 ]
[ 2134-29-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 60℃;	tbcada (308 mg, 0.46 mmol) was dissolved in methanol (11 mL). Acetic acid (89 muL), 3-hydroxypropanal, which was freshly prepared from <strong>[16777-87-0]3,3-diethoxy-1-propanol</strong> (1.0 g, 6.7 mmol) by HCl (10 mL, 0.5 M) treatment at 60C and isolated via its ether extract, and 5-ethyl-2-methylpyridine borane (92 mg, 0.68 mmol) were successively added. The solution was stirred for 18 hours at ambient temperature. The solvent was removed and the residue the residue was purified by chromatography on amino phase silica gel (ethyl acetate in hexane, 50 to 100%) to yield 256 mg of the title compound.

Reference： [1]Chemische Berichte,1908,vol. 41,p. 3605
[2]Justus Liebigs Annalen der Chemie,1910,vol. 374,p. 320
[3]Patent: EP2796152,2014,A1 .Location in patent: Paragraph 0128

3
[ 35573-93-4 ]
[ 16777-87-0 ]

Reference： [1]Chemische Berichte,1900,vol. 33,p. 2763
[2]Journal of the Chemical Society,1941,p. 406

4
[ 10601-80-6 ]
[ 16777-87-0 ]

Yield	Reaction Conditions	Operation in experiment
92%		In the following, tetrahydrofuran (THF) to be used was dehydrated on molecular sieves of 4 angstrom overnight. Inside of a 5 L four-neck flask was substituted with nitrogen gas and 2.2 kg of THF was placed therein, followed by cooling to 10 C. or lower. Then, 50 g of lithium aluminum hydride was placed therein and 250 g of ethyl 3,3-diethoxypropionate was added dropwise so that inner temperature did not exceed 10 C. After completion of the dropwise addition, temperature was elevated to 20 C. and reaction was carried out for 1 hour. After the reaction, 420 g of distilled water was added and the whole was stirred for 2 hours, then filtration was performed through No. 2 filtration paper, and subsequently a cake was washed with 1.1 kg of THF. The filtrate was concentrated at 40 C. to obtain 213 g of crude 3,3-diethoxy-1-propanol (hereinafter 33DEP).Then, 200 g of crude 33DEP was placed in a 5 L four-neck flask and 1 kg of hexane was added thereto, followed by stirring for 1 hour (step (A)). After 1 kg of a 0.1M phosphate buffer (pH 7.5) was added and the whole was stirred for 20 minutes, it was transferred to a 5 L separatory funnel and allowed to stand until it was separated into layers. After an aqueous layer was taken out, a hexane layer was returned to the 5 L four-neck flask and 1 kg of the 0.1M phosphate buffer (pH 7.5) was again added. After stirring for 20 minutes, the whole was again transferred to the 5 L separatory funnel and allowed to stand until it was separated into layers and then an aqueous layer was recovered. The aqueous layer was recovered into the 5 L four-neck flask (step (B)). Then, 2 kg of chloroform was added thereto and, after stirring for 30 minutes, the whole was transferred to the 5 L separatory funnel and allowed to stand for 15 minutes to separate it into layers. A chloroform layer was recovered and an aqueous layer was returned to the 5 L four-neck flask and the same operations were performed with 2 kg of chloroform to recover a chloroform layer (step (C)). Then, the recovered chloroform layer was concentrated at 40 C. using an evaporator and, after evaporation ceased, the solvent was evaporated by bubbling with a minute amount of nitrogen. Thereafter, the product was stirred with 20 g of molecular sieves of 4 angstrom for 5 hours and then filtration was performed to obtain 188 g of 33DEP.Then, 150 g of 33DEP obtained by the above operations was placed in a 300 ml four-neck flask and distillation was started under reduced pressure. A first fraction begun to be distilled at a degree of vacuum of 0.4 kPa, a bath temperature of 38 C., an inner temperature of 36 C., and a column top temperature of 33 C. After the distillation ceased, the bath temperature was gradually elevated and a main fraction begun to be distilled at a degree of vacuum of 0.2 kPa, a bath temperature of 58 C., an inner temperature of 55 C., and a column top temperature of 54 C. Thereafter, distillation was performed so that the column top temperature did not exceed 60 C. to obtain 138 g of the main fraction (step (D)). GC analysis was performed for the obtained main fraction. Results are shown in Table 1.
	In water;	(2) A three liter three-necked flask, condenser and addition funnel were dried in an oven at 140-150 C. overnight, assembled hot and cooled under a flow of dry nitrogen. Lithium aluminum hydride (7.2 g; 0.19 mole) and 800-900 ml of ether were placed in the flask with a magnetic stirring bar and the slurry was stirred vigorously. A solution of ethyl-3,3-diethoxypropionate (35 g; 0.184 mole) dissolved in 100-200 ml of ether was added to the lithium aluminum hydride slurry at a rate sufficient to keep the stirred slurry boiling. When addition was complete, the reaction mixture was refluxed for twelve hours. After cooling, 200 ml of water was added very cautiously with stirring and then carbon dioxide was bubbled into the mixture for two hours to hydrolyze the salts. The reaction mixture was filtered and the solids were washed several times with ether. The ether layer was separated, dried over sodium sulfate and evaporated to a colorless oil. Boiling range 85-87 C. at 10 mm (Lit. 90-92 C. at 10 mm) yield of 3-hydroxypropanal diethyl acetal 22 g; 85% by weight.

Reference： [1]Patent: US2012/277477,2012,A1 .Location in patent: Page/Page column 5
[2]Acta Chemica Scandinavica (1947),1973,vol. 27,p. 239 - 250
[3]Patent: US4634773,1987,A

5
[ 2134-29-4 ]
[ 122-51-0 ]
[ 16777-87-0 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 376 - 383

6
[ 16777-87-0 ]
[ 119-26-6 ]
[ 40365-04-6 ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 8502 - 8508
[2]Acta Chemica Scandinavica (1947),1973,vol. 27,p. 239 - 250

7
[ 110-87-2 ]
[ 16777-87-0 ]
[ 62592-78-3 ]

Reference： [1]Organic Preparations and Procedures International,1994,vol. 26,p. 121 - 122

8
[ 16777-87-0 ]
[ 6367-37-9 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1991,p. 1421 - 1422
[2]Tetrahedron Asymmetry,1994,vol. 5,p. 101 - 110
[3]European Journal of Organic Chemistry,2001,p. 2435 - 2446
[4]Tetrahedron Letters,2009,vol. 50,p. 7118 - 7120
[5]Journal of the American Chemical Society,2013,vol. 135,p. 9083 - 9090

9
[ 16777-87-0 ]
[ 6367-37-9 ]
[ 19060-08-3 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 1895 - 1910

10
[ 3054-95-3 ]
[ 16777-87-0 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 1895 - 1910
[2]Journal of Organic Chemistry,1981,vol. 46,p. 3978 - 3988
[3]Journal of Organic Chemistry,1981,vol. 46,p. 3978 - 3988

11
[ 3054-95-3 ]
[ 16777-87-0 ]
[ 1569-02-4 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 3978 - 3988

12
[ 78314-63-3 ]
[ 16777-87-0 ]

Reference： [1]Tetrahedron Asymmetry,1994,vol. 5,p. 101 - 110
[2]Journal of the Chemical Society. Chemical communications,1991,p. 1421 - 1422

13
[ 16777-87-0 ]
[ 51089-83-9 ]
[ 161690-39-7 ]

Reference： [1]Heterocycles,1995,vol. 40,p. 131 - 136

14
[ 16777-87-0 ]
[ 98-59-9 ]
[ 767321-23-3 ]

Reference： [1]Macromolecules,2004,vol. 37,p. 6786 - 6792

15
[ 1012073-06-1 ]
[ 16777-87-0 ]
C₁₂H₂₁N₃O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; for 2h;	Example 201; In 6 ml of tetrahydrofuran were dissolved 670 mg of the compound represented by the formula (IIa-1) and 470 mg of 3, 3-diethoxy-l-propanol, 130 mg of sodium hydride (60% oily) was added, and the mixture was stirred for 2 hours . Thereafter, an aqueous saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with t-butyl methyl ether. The organic layer was dried <n="258"/>with sodium sulfate, and concentrated under reduced pressure. The residue was subjected to medium pressure preparative liquid chromatography to obtain 450 mg of a compound represented by the formula (201) :(hereinafter, referred to as compound (201) ) . 1H-NMR (CDCl3, TMS) delta (ppm) : 4.69 (IH, t) , 4.61 (2H, t) , 3.71-3.64 (2H, m)' , 3.55-3.48 (2H, m) , 3.04 (6H, 'br), 2.14 (2H, dt, J=6Hz, 6Hz), 1.21 (6H, t)

Reference： [1]Patent: WO2008/32858,2008,A2 .Location in patent: Page/Page column 256-257

16
[ 16777-87-0 ]
[ 17435-72-2 ]
[ 940279-22-1 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1931 - 1934

17
[ 16777-87-0 ]
(2R,3S,4R,5R,6R)-2-(3,3-Diethoxy-propoxy)-6-isobutoxymethyl-4,5-dimethoxy-tetrahydro-pyran-3-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2001,vol. 40,p. 3870 - 3873

18
[ 16777-87-0 ]
[ 400835-55-4 ]

Reference： [1]Angewandte Chemie - International Edition,2001,vol. 40,p. 3870 - 3873

19
[ 16777-87-0 ]
[ 400835-57-6 ]

Reference： [1]Angewandte Chemie - International Edition,2001,vol. 40,p. 3870 - 3873

20
[ 16777-87-0 ]
[ 400835-56-5 ]

Reference： [1]Angewandte Chemie - International Edition,2001,vol. 40,p. 3870 - 3873

21
[ 16777-87-0 ]
[ 333986-73-5 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 2435 - 2446

22
[ 16777-87-0 ]
(S)-6,6-Diethoxy-4-ethyl-hexan-2-one [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 2435 - 2446

23
[ 16777-87-0 ]
[ 333986-84-8 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 2435 - 2446

24
[ 16777-87-0 ]
[ 319439-56-0 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 843 - 847

25
[ 16777-87-0 ]
[ 319439-58-2 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 843 - 847

26
[ 16777-87-0 ]
[ 111606-92-9 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 843 - 847

27
[ 16777-87-0 ]
[ 319439-60-6 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 843 - 847

28
[ 16777-87-0 ]
[ 138665-68-6 ]