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Chemical Structure| 2050-94-4 Chemical Structure| 2050-94-4

Structure of Dipentyl carbonate
CAS No.: 2050-94-4

Chemical Structure| 2050-94-4

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Product Details of [ 2050-94-4 ]

CAS No. :2050-94-4
Formula : C11H22O3
M.W : 202.29
SMILES Code : O=C(OCCCCC)OCCCCC
MDL No. :MFCD00068969
InChI Key :HSNQKJVQUFYBBY-UHFFFAOYSA-N
Pubchem ID :222266

Safety of [ 2050-94-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 2050-94-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 0
Fraction Csp3 0.91
Num. rotatable bonds 10
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 57.75
TPSA ?

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

35.53 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.6
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

4.11
Log Po/w (WLOGP)?

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

3.52
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.

2.4
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

2.82
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.29

Water Solubility

Log S (ESOL):?

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

-3.02
Solubility 0.192 mg/ml ; 0.000947 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-4.56
Solubility 0.00554 mg/ml ; 0.0000274 mol/l
Class?

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

Moderately 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

-3.33
Solubility 0.0951 mg/ml ; 0.00047 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.

-4.62 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

0.0
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

0.0 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<3.0
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)

2.48

Application In Synthesis of [ 2050-94-4 ]

* 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 [ 2050-94-4 ]

[ 2050-94-4 ] Synthesis Path-Downstream   1~13

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YieldReaction ConditionsOperation in experiment
86% With 2-Cyanopyridine; cerium(IV) oxide; at 109.84℃; under 37503.8 Torr; for 48.0h;Autoclave; General procedure: All the reactions were carried out in an autoclave reactor withan inner volume of 190 ml. A typical procedure of the reaction of CO2 + methanol with 2-cyanopyridine was as follows: 0.34 g of CeO2 catalyst, 0.64 g of methanol (20 mmol, Wako Pure Chemical Industries, 99.8percent min.), and 10.4 g of 2-cyanopyridine (100 mmol,Tokyo Chemical Industry Co., Ltd., 99.0percent min.) were put into the autoclave together with a spinner, and then, the reactor was purged and pressurized with CO2 (Shimakyu Co. Ltd., >99.5percent). Gas line was closed, and then, the reactor was heated to the reaction temperature. The time when the temperature reached the desired reaction temperature is defined as zero reaction time. The mixture was constantly stirred during the reaction. After the specific reaction time, the reactor was cooled to room temperature and the gas was collected. Ethanol (30 ml, Wako Pure Chemical Industries, 99.5percent min.) and 1-hexanol (0.2 ml, Tokyo ChemicalIndustry Co., Ltd., 98.0percent min.) were added to the liquid phase asa solvent and an internal standard substance for a quantitativeanalysis, respectively. Products in the liquid and gas phases were analyzed by using a gas chromatograph equipped with FID(Shimadzu GC-2014) and GC?MS (Shimadzu QP-2020) with a CP-Sil5 capillary column (length 50 m, i.d. 0.25 mm, film thickness0.25 mum). For the synthesis of various carbonates from CO2 and the corresponding alcohols, the procedures are the same as the case of the reaction of CO2 + methanol with 2-cyanopyridine. After the reaction time, 30 ml of ethanol or acetone (Wako Pure Chemical Industries,99.5percent min.) was added to the liquid phase as a solvent, and 0.2 ml of 1-hexanol or 1-propanol (Wako Pure Chemical Industries,99.5percent min.) was added to the liquid phase as an internal standard substance for a quantitative analysis. The products in the liquid and gas phases were analyzed by gas chromatography equippedwith an FID or quadrupole mass spectrometer (GC?MS) using a CP-Sil5 capillary column (length 50 m, i.d. 0.25 mm, film thickness 0.25 mum) or TC-WAX capillary column (length 30 m, i.d. 0.25 mm, film thickness 0.25 mum).
  • 4
  • [ 71-41-0 ]
  • [ 594-42-3 ]
  • [ 2050-94-4 ]
  • [ 94138-04-2 ]
  • 5
  • [ 71-41-0 ]
  • [ 57-13-6 ]
  • [ 2050-94-4 ]
YieldReaction ConditionsOperation in experiment
92.2% With nickel diacetate; triphenylphosphine; at 140 - 170℃; for 20.0h; The reaction apparatus was the same as in Example 1. 10 g of urea, 60 g of n-pentanol, 0.5 g of nickel acetate, 2 g of triphenylphosphine in a three-necked flask were placed in a 170 ° C oil bath, the system was boiled at 140 ° C, and refluxed for 20 hr. Gas chromatography analysis showed that the yield of di-n-pentyl carbonate was 92.2percent based on the amount of urea charged.
YieldReaction ConditionsOperation in experiment
70% With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; 1,2-dibromomethane; at 70℃; for 18.0h;Sealed tube; General procedure: For the synthesis of organic carbonates from cinnamyl alcohol, organic solvent and alcohol activating agent 1 mL of dichloromethane (DCM) and 0.1 mL of an ionic liquid of 1-butyl-3-methylimidazolium hexafluorophosphate, bmimPF6 to the mixture was added 0.5 mM cinnamyl alcohol and 2 equivalents of cesium carbonate (Cs2CO3), which is the carbon donating source, were stirred at 70C for 18 hours. Thereafter, the reaction mixture was cooled and separated and purified by column chromatography to obtain a carbonate 1a compound. Was synthesized in the same manner as in Example 1, except that 1 mL of dibromomethane (DBM) was used instead of dichloromethane to obtain a carbonate 1a compound. On the other hand, carbonate 1a was synthesized using various alcohols and cesium carbonate, including benzyl alcohol, allyl alcohol and aliphatic alcohol, in addition to the cinnamic alcohol shown in Table 1. To the solvent was added a mixture of 0.5 mM alcohol and 1.0 mM cesium carbonate in a seal tube for 18 hours at 70C. The results are shown in Table 2.
63.7% With C12H24N3(1+)*CHO3(1-); 1,3,4-triazole, cesium salt; at 80℃; under 15514.9 Torr; for 24.0h; General procedure: 1) A mixture was prepared by mixing high pressure stainless steel reactor with magnetic stirrer and electric heater of 5 mmol methanol in 100 ml, 5 mmol of an imidazolium cation and a bicarbonate anion ([IL tagged Hunig base] [HCO 3]), 5 mmol Cs [Triazolide] base and 15 ml CH2Br2 solvent. 2) The mixture was purged of carbon dioxide to the reactor at 80 psi pressure. 3) The atmosphere was evacuated three times from the mixture. 4) Stir at 500 rpm, and It was heated to 50 temperature and increase the carbon dioxide pressure at 300psi. 5) The reaction was carried out for 24 hours while maintaining the carbon dioxide pressure at 300 psi to prepare dimethyl carbonate (DMC). 6) After the reaction was completed, the reaction mixture was allowed to stand at room temperature, and the resulting mixture was transferred to a vial to calculate the conversion of methanol and the yield of dimethyl carbonate using GD-FID.
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  • Ag2CO3 [ No CAS ]
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  • [ 110-53-2 ]
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  • 9
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  • [ 108-95-2 ]
  • [ 102-09-0 ]
  • [ 917760-08-8 ]
  • [ 71-41-0 ]
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  • [ 71-41-0 ]
  • [ 616-38-6 ]
  • [ 183013-07-2 ]
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  • 11
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  • [ 108-95-2 ]
  • [ 102-09-0 ]
YieldReaction ConditionsOperation in experiment
5percent by mass titanium-containing composition; at 200 - 230℃; under 22.5023 - 1050.11 Torr;Industry scale;Product distribution / selectivity; Examples 2 to 6; Start-up operation was performed in the same manner as in the example 1 except that dialkyl carbonates of types shown in the following Table 1 were used in place of bis(3-methylbutyl)carbonate, so as to produce diphenyl carbonate (diaryl carbonate). A flow rate and a pressure were controlled depending on the type of each dialkyl carbonate in control operation.In distillation separation in a distillation column 130, a high boiling component removed from a column bottom contained about 7percent by mass, about 10percent by mass, about 8percent by mass, about 9percent by mass, and about 8percent by mass of a component having a higher boiling point than that of the diphenyl carbonate, in order of examples 2 to 6.The results of analyzing a titanium-containing high boiling component obtained from a removal line 11 are shown in Table 1. All the examples satisfied the conditions of the above-mentioned items (iv) to (vi), and could stably produce the diaryl carbonates.
  • 12
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YieldReaction ConditionsOperation in experiment
70% With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 70℃; for 18.0h;Sealed tube; General procedure: A mixture of cinnamyl alcohol (67.1 mg, 0.5mmol), Cs2CO3 (325.8 mg, 1 mmol) and 1-n-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) (0.1 mL) in dibromomethane (1 mL) was equipped with a seal tube and stirred for 18 h at 70° C. The reaction mixture was evaporated and purified by flash column chromatography (silica gel) (2percent Ether/hexane) to obtain dicinnamyl carbonate (1a) 69.0 mg (94percent).
  • 13
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YieldReaction ConditionsOperation in experiment
66% With tetraethylammonium nitrilotriacetate; at 130℃; for 2.0h; General procedure: The transesterification reaction was carried out in a 50 mLround-bottomed flask, equipped with a condenser, thermostatand magnetic stirring. A calculated amount of DMC, THFA,and APC-ILs were added to the reactor, and the reaction mixturewas stirred and allowed to proceed for 0.5?2.5h with theheating at the designed temperature (e.g., 130 °C). After thereaction was completed, qualitative analyses of products wereexamined by a Thermo Trace 1300 GC-ISQ, and quantitativeanalyses were carried out by a GC-FID (Agilent 7890B)equipped with a capillary column HP-5 (methyl polysiloxane,30 m × 0.32 mm × 1 m). The detailed analysis conditionswere described as follows: The temperatures of injector anddetector were 280 and 250 °C, respectively. The column temperaturewas increased stepwise to 200 °C, holding at 80 °Cfor 2 min, increasing to 200 °C at 40 °C min?1, holding at240 °C for 3min. Then the conversion of DMC and yield ofDTC were calculated according to the area of chromatographpeaks using 1,3,5-trimethylbenzene as an internal standard.After the completion of reaction, the reaction system wascooled down to room temperature and extracted with deionizedwater, and the system thus forms a liquid?liquid biphase,and the aqueous phase containing APC-ILs could be easilyseparated by simple decantation. After that, the catalyst APCILswere further heated in a vacuum oven at 90 °C for 6h toremove water and the residual reactants. The water contentof recycled APC-ILs was measured prior to the next run andchecked to be less than 0.15wtpercent by the Karl Fisher titration.
With tetraethylammonium L-prolinate; at 110℃; for 4.0h; In a typical procedure, [N2222][Pro] (0.5 wtpercent, based on the total weight of DMC and BuOH), DMC (20 mmol) and BuOH (80 mmol)were added into a round-bottomed flask (50 mL) fitted with a magnetic stirrer and condenser. Then, the reaction mixture was vigorously stirred and allowed to proceed for 1?6 h with the heating at the designed temperature (e.g., 110 °C). After the reaction was completed, the reactor was cooled down. About 0.2 mL of liquid sample was taken from the reactor and detected by gas chromatography (GC). Subsequently, the reaction mixture was extracted with deionized water (10 mL × 3), and the system thus forms a liquid?liquid biphase, and the aqueous phase containing ILs could be easily separated by simple decantation. After that, the catalyst ILs were further in a vacuum oven at 80 °C for 12 h to remove water and the residual reactants prior to reuse in the next run. Qualitative analyses of products were examined by a Thermo Trace 1300 GC-ISQ, and quantitative analyses were carried out by a GC-FID (Agilent 7890B).The detailed analysis conditions were described as follows: the injector and detector temperatures were 250 and 250C, respectively; the column temperature was increased stepwise to 200 °C,holding at 80 °C for 2 min, increasing to 200 °C at 40 °C min?1,holding at 200 °C for 5 min. Then the conversion and selectivity were calculated according to the area of chromatograph peak usingbiphenyl as an internal standard.
 

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