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Chemical Structure| 821-09-0 Chemical Structure| 821-09-0

Structure of 4-Penten-1-ol
CAS No.: 821-09-0

Chemical Structure| 821-09-0

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Synonyms: Pent-4-en-1-ol

4.5 *For Research Use Only !

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Product Details of [ 821-09-0 ]

CAS No. :821-09-0
Formula : C5H10O
M.W : 86.13
SMILES Code : C=CCCCO
Synonyms :
Pent-4-en-1-ol
MDL No. :MFCD00002975
InChI Key :LQAVWYMTUMSFBE-UHFFFAOYSA-N
Pubchem ID :13181

Safety of [ 821-09-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225
Precautionary Statements:P210-P403+P235
Class:3
UN#:1987
Packing Group:

Computational Chemistry of [ 821-09-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 6
Num. arom. heavy atoms 0
Fraction Csp3 0.6
Num. rotatable bonds 3
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 26.84
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.66
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.0
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.94
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.01
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.84
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.09

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.81
Solubility 13.5 mg/ml ; 0.156 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.01
Solubility 8.35 mg/ml ; 0.0969 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.86
Solubility 11.9 mg/ml ; 0.138 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.12 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.26

Application In Synthesis of [ 821-09-0 ]

* 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.

  • Downstream synthetic route of [ 821-09-0 ]

[ 821-09-0 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 821-09-0 ]
  • [ 928-50-7 ]
YieldReaction ConditionsOperation in experiment
95.22% With pyridine; thionyl chloride; bismuth(III) oxide; at 0 - 30℃; for 72h; In a 2000 ml four-necked flask equipped with a mechanical stirrer, a dropping funnel, a reflux condenser and a thermometer,200 g (2.33 mol) of 4-penten-1-ol, 2 g of bismuth trioxide and 700 g of pyridine were added.The temperature of the system was lowered to 0 C with ice-salt bath with stirring. At this point, 238 g (2 mol) of thionyl chloride was added dropwise to the system with a dropping funnel.Control the rate of dropping to ensure that the material temperature does not exceed 5 , dropping the end, remove the ice salt bath. Naturally heated to between 10-30 , the reaction was stirred for 72 hours.When the temperature exceeds 30 , use ice salt bath to cool below 30 . After the reaction was completed, the mixture was filtered through a Buchner funnel and the filter cake was taken as a catalyst and pyridine hydrochloride. The filter cake was rinsed twice with 200 ml of acetone.The combined filtrate and washings, poured into 1500ml of distilled water, allowed to stand, separate the lower reservoir.The oil layer was further washed with distilled water to neutrality, and then distilled under reduced pressure in a water pump to collect the distillate fraction (vacuum 255 mmHg) at a head temperature of 88-95 C.199g colorless liquid was obtained in a yield of 95.22%. Gas chromatography detection of content of 98.27%.
  • 2
  • [ 821-09-0 ]
  • [ 3356-89-6 ]
  • [ 62847-61-4 ]
  • 3
  • [ 928-50-7 ]
  • [ 96-47-9 ]
  • [ 821-09-0 ]
  • [ 15146-94-8 ]
  • 4
  • [ 91606-67-6 ]
  • [ 821-09-0 ]
  • [ 928-50-7 ]
  • 5
  • [ 110-86-1 ]
  • [ 821-09-0 ]
  • [ 7719-12-2 ]
  • [ 928-50-7 ]
  • 7
  • [ 821-09-0 ]
  • [ 6608-47-5 ]
  • [ 516522-35-3 ]
  • 8
  • [ 821-09-0 ]
  • [ 7126-57-0 ]
  • [ 934475-66-8 ]
  • 9
  • [ 821-09-0 ]
  • [ 50607-30-2 ]
  • [ 1016555-65-9 ]
  • 10
  • [ 821-09-0 ]
  • [ 20026-96-4 ]
  • [ 1511357-03-1 ]
  • 11
  • [ 105486-72-4 ]
  • [ 821-09-0 ]
  • ethyl 1-methyl-5-(pent-4-en-1-yloxy)-1H-pyrazole-4-carboxylate [ No CAS ]
  • pent-4-en-1-yl 1-methyl-5-(pent-4-en-1-yloxy)-1H-pyrazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.1.6 1-Methyl-5-(pent-4-en-1-yloxy)-1H-pyrazole-4-carboxylic acid 10b A solution of pent-4-en-1-ol (1.45?mL, 14.0?mmol) in THF (24.0?mL) was cooled to -8?C and treated with 1.0?M sodium hexamethyldisilazane in THF (14.0?mL, 14.0?mmol). The reaction mixture was stirred at the reduced temperature for 5?min before the ice bath was removed. Stirring was continued for an additional 25?min before being treated with a solution of <strong>[105486-72-4]ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate</strong> (1.1?g, 4.7?mmol) in THF (24?mL). The reaction mixture was stirred for 1 hour at room temperature before being quenched with 50?mL of sat. NH4Cl. The crude product was extracted with DCM (60?mL x 3), dried with Na2SO4 and concentrated under reduced pressure. This material purified by SiO2 chromatography (ethyl acetate: petroleum ether?=?1:5) to afford 0.65?g impure product 9b mixed with pent-4-en-1-yl 1-methyl-5-(pent-4-en-1-yloxy)-1H-pyrazole-4-carboxylate (produced through transesterification reaction), the mixed esters could both be the raw materials for next hydrolysis, so the mixture was put into next step without further separation. To a solution of the mixed esters in 5?mL MeOH/THF (VMeOH:VTHF?=?1:1) at 0? was added 5?mL 2M NaOH (aq). The mixture was stirred at room temperature for 3?h and MeOH and THF were evaporated in vacuo. The residue was acidified to pH?=?2-3 with 1?N HCl and extracted with ethyl acetate (10?mL?*?3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford compound 10b as yellow solid (0.45?g, 46%). 1 H NMR (500?MHz, CDCl3) delta 7.84 (s, 1H), 5.89-5.77 (m, 1H), 5.10-5.00 (m, 2H), 4.46 (t, J?=?6.5?Hz, 2H), 3.70 (s, 4H), 2.28-2.19 (m, 2H), 1.93-1.85 (m, 2H); ESI-MS: m/z?=?209 [M-H]-.
  • 12
  • [ 105486-72-4 ]
  • [ 821-09-0 ]
  • 1-methyl-5-(pent-4-en-1-yloxy)-1H-pyrazole-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% A solution of pent-4-en-1-ol (1.45?mL, 14.0?mmol) in THF (24.0?mL) was cooled to -8?C and treated with 1.0?M sodium hexamethyldisilazane in THF (14.0?mL, 14.0?mmol). The reaction mixture was stirred at the reduced temperature for 5?min before the ice bath was removed. Stirring was continued for an additional 25?min before being treated with a solution of <strong>[105486-72-4]ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate</strong> (1.1?g, 4.7?mmol) in THF (24?mL). The reaction mixture was stirred for 1 hour at room temperature before being quenched with 50?mL of sat. NH4Cl. The crude product was extracted with DCM (60?mL x 3), dried with Na2SO4 and concentrated under reduced pressure. This material purified by SiO2 chromatography (ethyl acetate: petroleum ether?=?1:5) to afford 0.65?g impure product 9b mixed with pent-4-en-1-yl 1-methyl-5-(pent-4-en-1-yloxy)-1H-pyrazole-4-carboxylate (produced through transesterification reaction), the mixed esters could both be the raw materials for next hydrolysis, so the mixture was put into next step without further separation. To a solution of the mixed esters in 5?mL MeOH/THF (VMeOH:VTHF?=?1:1) at 0? was added 5?mL 2M NaOH (aq). The mixture was stirred at room temperature for 3?h and MeOH and THF were evaporated in vacuo. The residue was acidified to pH?=?2-3 with 1?N HCl and extracted with ethyl acetate (10?mL?*?3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford compound 10b as yellow solid (0.45?g, 46%). 1 H NMR (500?MHz, CDCl3) delta 7.84 (s, 1H), 5.89-5.77 (m, 1H), 5.10-5.00 (m, 2H), 4.46 (t, J?=?6.5?Hz, 2H), 3.70 (s, 4H), 2.28-2.19 (m, 2H), 1.93-1.85 (m, 2H); ESI-MS: m/z?=?209 [M-H]-.
  • 13
  • [ 821-09-0 ]
  • [ 221044-05-9 ]
  • [ 201230-82-2 ]
  • pent-4-enyl 1-(pyrimidin-2-yl)-1H-indole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With rhodium(III) chloride trihydrate; copper diacetate; In N,N-dimethyl-formamide; at 90℃; under 760.051 Torr; for 10h;Sealed tube; AddN-pyrimidinylpurine 1a (0.2 mmol), RhCl3•3H2O (0.004 mmol), Cu(OAc)2(0.4 mmol) andpent-4-en-1-ol 2l (1.0 mmol) to 2.0 In mL of DMF, after replacing carbon monoxide three times in Young's tube,add carbon monoxide (1 atm), react with 90 C oil bath for 10 hours, stop the reaction, wait until the reaction solution is cooled to room temperature, addethyl acetate and saturate The saline is washed and extracted several times.The organic phase was dried over anhydrous sodium sulfate and filtered.The solvent was evaporated to dryness, andethyl acetate / petroleum ether (1:10 to 1:1) was obtained.The product was a colorless oily liquidwith a yield of 65%.
 

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Technical Information

Categories

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