Home Cart 0 Sign in  

[ CAS No. 82578-45-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 82578-45-8
Chemical Structure| 82578-45-8
Structure of 82578-45-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 82578-45-8 ]

Related Doc. of [ 82578-45-8 ]

Alternatived Products of [ 82578-45-8 ]

Product Details of [ 82578-45-8 ]

CAS No. :82578-45-8 MDL No. :MFCD00040559
Formula : C8H16O3 Boiling Point : -
Linear Structure Formula :- InChI Key :PKPVFILAHLKSNJ-LURJTMIESA-N
M.W : 160.21 Pubchem ID :10154184
Synonyms :

Calculated chemistry of [ 82578-45-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.05
TPSA : 46.53 Ų

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) : -6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 0.78
Log Po/w (WLOGP) : 1.1
Log Po/w (MLOGP) : 1.08
Log Po/w (SILICOS-IT) : 0.9
Consensus Log Po/w : 1.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.06
Solubility : 13.9 mg/ml ; 0.087 mol/l
Class : Very soluble
Log S (Ali) : -1.34
Solubility : 7.36 mg/ml ; 0.0459 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.03
Solubility : 14.8 mg/ml ; 0.0925 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.27

Safety of [ 82578-45-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 82578-45-8 ]

* 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.

  • Upstream synthesis route of [ 82578-45-8 ]
  • Downstream synthetic route of [ 82578-45-8 ]

[ 82578-45-8 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 1694-31-1 ]
  • [ 82578-45-8 ]
YieldReaction ConditionsOperation in experiment
80.3% With Rhizopus arrhizus In ethanol; water at 24 - 25℃; for 72 h; Microbiological reaction; Enzymatic reaction General procedure: The laboratory scale-up bioreduction of ketones 1–7 was carried out as follows. After 72h of fermentation, R. arrhizus mycelia were separated from the culture broth. The 10percent wet mycelia were put in a 1.5L sterilized fresh culture medium as working volume in 5L Erlenmeyer flask under aseptic conditions and incubated at room temperature for 72h under static conditions. After the growth of the fungus, the substrate (1g) in ethanol was added directly to the medium and then incubated at room temperature on a rotary shaker (100rpm) for 8days. At the end of the incubation period, the mycelia were separated by filtration. Mycelia was washed with water and then the combined aqueous medium was extracted with chloroform. The chloroform extract washed with water and dried over Na2SO4. After removal of the solvent under reduced pressure, the product alcohol was isolated, purified, and characterized as described earlier. The absolute configuration was determined by the sign of the specific rotation and comparison with the literature data. Isolated yield: 0.81g, [α]D26=+28.6 (c 0.483, CHCl3) >99percent ee {lit.2f=+32.3 (c 1.03, CHCl3), 99.0percent ee}; 1H NMR (CDCl3, 200MHz): δ 1.25 (d, 3H, CH3), 1.48 (s, 9H, CH3), 2.27–2.49 (m, 2H, CH2), 3.09 (s, 1H, OH),, 4.08–4.22 (m, 1H, CHOH); 13C NMR (CDCl3, 200MHz, ppm): 22.21, 27.93, 43.79, 64.18, 80.94, 172.15; methoxyl resonances of MTPA ester, 1H NMR: δ 3.55 [major, (S)-isomer]
97 % ee With D-Glucose In water at 30℃; for 2.73333 h; Flow reactor; Enzymatic reaction General procedure: A solution of 5 g of glucose in 100 mL of distilled water was prepared and the β-ketoester [ethyl 3-oxohexanoate (1) or tert-butyl 3-oxobutanoate (2)] were added to the solution (0.025 mol L-1 or 4 g L-1). The starting mixture was stirred for 5 min while the instrument Asia Flow Reactor was equipped with Omnifit column (volume: 12.3 mL) containing the immobilized cells from Kluyveromyces marxianus [for the bioreduction of ethyl 3-oxohexanoate (1)] and Rhodotorula rubra [for the bioreduction of tert-butyl 3-oxobutanoate (2)]. The temperature (30 °C) was selected on the flow reactor and for each flow tested (0.2 mL min‑1, 0.1 mL min-1 and 0.075 mL min-1), first only the pure solvent (glucose 5percent) was pumped through the system. At this point, the reaction mixture [ethyl 3-oxohexanoate (1) ortert‑butyl 3-oxobutanoate (2)] was pumped through the system and aliquots were collected in different times depending on the flow rate tested (0.2 mL min-1 = 62 min; 0.1 mL min‑1 = 123 min; 0.075 mL min-1 = 164 min). The reaction mixture was extracted with ethyl acetate. The organic phase was dried (anhydrous Na2SO4), filtered, and concentrated under vacuum. Products were analyzed by (chiral) gas chromatography (GC).
Reference: [1] RSC Advances, 2016, vol. 6, # 34, p. 28447 - 28450
[2] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4619 - 4622
[3] Tetrahedron Asymmetry, 2008, vol. 19, # 19, p. 2272 - 2275
[4] Tetrahedron: Asymmetry, 2016, vol. 27, # 4-5, p. 188 - 192
[5] Tetrahedron Asymmetry, 1997, vol. 8, # 7, p. 1049 - 1054
[6] Tetrahedron Asymmetry, 2004, vol. 15, # 21, p. 3397 - 3400
[7] Chemistry - A European Journal, 2010, vol. 16, # 2, p. 577 - 587
[8] Helvetica Chimica Acta, 1982, vol. 65, # 2, p. 495 - 503
[9] Tetrahedron Letters, 2009, vol. 50, # 34, p. 4934 - 4936
[10] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 12, p. 3314 - 3319
[11] Journal of the American Chemical Society, 1995, vol. 117, # 15, p. 4423 - 4424
[12] Tetrahedron Letters, 1996, vol. 37, # 10, p. 1699 - 1702
[13] Journal of Organic Chemistry, 1998, vol. 63, # 24, p. 8957 - 8964
[14] Journal of Organic Chemistry, 2006, vol. 71, # 7, p. 2874 - 2877
[15] Tetrahedron Letters, 1992, vol. 33, # 18, p. 2477 - 2480
[16] Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2322 - 2328
[17] Advanced Synthesis and Catalysis, 2009, vol. 351, # 16, p. 2553 - 2557
[18] Tetrahedron Letters, 2009, vol. 50, # 50, p. 7079 - 7081
[19] Synthetic Communications, 2013, vol. 43, # 12, p. 1611 - 1618
[20] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 3, p. 550 - 554
[21] Journal of Organic Chemistry, 2015, vol. 80, # 16, p. 8055 - 8064
  • 2
  • [ 1694-31-1 ]
  • [ 82578-45-8 ]
  • [ 110171-06-7 ]
YieldReaction ConditionsOperation in experiment
84 % ee With hydrogen; acetic acid In tetrahydrofuran at 100℃; for 20 h; Autoclave General procedure: Nickel powders (5 μm) purchased from Aldrich were directly subjected to chiral modification without any pretreatment, such as hydrogen activation. The chiral modification was performed under the conditions optimized previously for this type of catalyst.26 Thus, the non-activated nickel powders (0.5 g) were immersed in an aqueous solution (50 cm3) of (R,R)-tartaric acid (0.5g) and NaBr (2.0 g) at 100 °C, the pH of which was pre-adjusted to 3.2 with an aqueous 1M NaOH solution. NaBr was added to the modification solution to block the non-enantiodifferentiating sites of tartaric acid/Ni catalyst, thus preventing the generation of racemic products.39 After immersion for 1 h, the modification solution was removed by decantation and the catalyst was successively washed once with deionized water (10 cm3), twice with methanol (25 cm3), and twice with tetrahydrofuran (THF) (10 cm3). The modified catalyst was added to a mixture of alkyl acetoacetate (43 mmol for methyl ester and 21.5 mmol for other esters), acetic acid (0.1g), and THF (10 cm3) placed in an autoclave equipped with a magnetically coupled mechanical stirrer. The hydrogenation was run for 20h at 100 or 110 °C and at a hydrogen pressure of 9MPa. The hydrogenation product, a mixture of alkyl (R)- and (S)-3-hydroxybutyrates, was isolated from the reaction mixture by distillation. The conversion was determined by gas-liquid chromatography (GLC) on a GL Science model GC-4000 equipped with a CP Chirasil DEX-CB capillary column (0.25 mm × 25 m) at 90 °C, while the enantioselectivity was determined by chiral GLC after acetylation of the reaction product using acetyl chloride and pyridine. A portion of the acetylated sample was subjected to the chiral GLC analysis on a CP Chirasil DEX-CB column (0.25 mm × 25 m) operated at 90 °C. The ee value was calculated from the peak integration of the corresponding enantiomer peaks. The reproducibility of the ee value was found to be within ±2percent.
89.2 % ee With hydrogen In isopropyl alcohol at 50℃; for 10 h; Autoclave; Glovebox General procedure: As a typical run for asymmetric hydrogenation of β-keto esters, 0.026 g Ru/5-BINAPPOPs-1 catalyst, 0.20 g methyl acetoacetate, and 2 mL of isopropanol (ipro) were added to a 30-mL autoclave in a glove box. After the reactor was purged with H2 four times, its pressure was finally adjusted to the desired value, heated from room temperature to the reaction temperature of 50 °C, and stirred for 10 h. The catalyst was separated by centrifugation, and the product was analysed using gas chromatography (GC; Agilent 7890B gas chromatograph equipped with a flame ionization detector and a Cyclosil-B capillary column).
Reference: [1] Patent: US2004/192543, 2004, A1, . Location in patent: Page/Page column 9
[2] Journal of the Chemical Society, Chemical Communications, 1983, # 10, p. 599 - 600
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 6, p. 1826 - 1828
[4] Tetrahedron Letters, 1998, vol. 39, # 25, p. 4441 - 4444
[5] European Journal of Organic Chemistry, 2001, # 2, p. 275 - 291
[6] Tetrahedron Asymmetry, 1999, vol. 10, # 21, p. 4083 - 4086
[7] Angewandte Chemie - International Edition, 2003, vol. 42, # 48, p. 6000 - 6003
[8] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7577 - 7581
[9] Chemical Communications, 2004, # 20, p. 2284 - 2285
[10] Advanced Synthesis and Catalysis, 2006, vol. 348, # 15, p. 2172 - 2182
[11] Advanced Synthesis and Catalysis, 2003, vol. 345, # 1-2, p. 67 - 77
[12] Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2322 - 2328
[13] Tetrahedron Letters, 2009, vol. 50, # 50, p. 7079 - 7081
[14] Synthetic Communications, 2013, vol. 43, # 12, p. 1611 - 1618
[15] Tetrahedron Asymmetry, 2014, vol. 25, # 24, p. 1630 - 1633
[16] Chinese Journal of Catalysis, 2017, vol. 38, # 5, p. 890 - 897
  • 3
  • [ 90435-23-7 ]
  • [ 82578-45-8 ]
  • [ 110171-06-7 ]
  • [ 120444-06-6 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 6, p. 1972 - 1977
  • 4
  • [ 142176-66-7 ]
  • [ 82578-45-8 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 18, p. 2477 - 2480
  • 5
  • [ 142176-64-5 ]
  • [ 82578-45-8 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 18, p. 2477 - 2480
  • 6
  • [ 95112-71-3 ]
  • [ 82578-45-8 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 44, p. 5083 - 5086
  • 7
  • [ 120444-07-7 ]
  • [ 82578-45-8 ]
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 12, p. 2430 - 2461
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 82578-45-8 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 18267-36-2

[ 18267-36-2 ]

Ethyl 3-hydroxy-3-methylbutanoate

Similarity: 0.93

Chemical Structure| 24915-95-5

[ 24915-95-5 ]

Ethyl (R)-3-hydroxybutyrate

Similarity: 0.90

Chemical Structure| 5405-41-4

[ 5405-41-4 ]

Ethyl 3-hydroxybutanoate

Similarity: 0.90

Chemical Structure| 15026-17-2

[ 15026-17-2 ]

4-(tert-Butoxy)-4-oxobutanoic acid

Similarity: 0.90

Chemical Structure| 843666-40-0

[ 843666-40-0 ]

18-(tert-Butoxy)-18-oxooctadecanoic acid

Similarity: 0.87

Alcohols

Chemical Structure| 18267-36-2

[ 18267-36-2 ]

Ethyl 3-hydroxy-3-methylbutanoate

Similarity: 0.93

Chemical Structure| 24915-95-5

[ 24915-95-5 ]

Ethyl (R)-3-hydroxybutyrate

Similarity: 0.90

Chemical Structure| 5405-41-4

[ 5405-41-4 ]

Ethyl 3-hydroxybutanoate

Similarity: 0.90

Chemical Structure| 5326-50-1

[ 5326-50-1 ]

Ethyl 2-(1-hydroxycyclohexyl)acetate

Similarity: 0.88

Chemical Structure| 2305-25-1

[ 2305-25-1 ]

Ethyl 3-hydroxyhexanoate

Similarity: 0.87

Esters

Chemical Structure| 18267-36-2

[ 18267-36-2 ]

Ethyl 3-hydroxy-3-methylbutanoate

Similarity: 0.93

Chemical Structure| 24915-95-5

[ 24915-95-5 ]

Ethyl (R)-3-hydroxybutyrate

Similarity: 0.90

Chemical Structure| 5405-41-4

[ 5405-41-4 ]

Ethyl 3-hydroxybutanoate

Similarity: 0.90

Chemical Structure| 15026-17-2

[ 15026-17-2 ]

4-(tert-Butoxy)-4-oxobutanoic acid

Similarity: 0.90

Chemical Structure| 5326-50-1

[ 5326-50-1 ]

Ethyl 2-(1-hydroxycyclohexyl)acetate

Similarity: 0.88