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Chemical Structure| 3130-19-6 Chemical Structure| 3130-19-6

Structure of 3130-19-6

Chemical Structure| 3130-19-6

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Product Details of [ 3130-19-6 ]

CAS No. :3130-19-6
Formula : C20H30O6
M.W : 366.45
SMILES Code : O=C(CCCCC(OCC1CC2OC2CC1)=O)OCC3CC4OC4CC3
English Name :Bis(7-oxabicyclo[4.1.0]heptan-3-ylmethyl) adipate
MDL No. :MFCD00191811
InChI Key :DJUWPHRCMMMSCV-UHFFFAOYSA-N
Pubchem ID :18410

Safety of [ 3130-19-6 ]

Computational Chemistry of [ 3130-19-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 26
Num. arom. heavy atoms 0
Fraction Csp3 0.9
Num. rotatable bonds 11
Num. H-bond acceptors 6.0
Num. H-bond donors 0.0
Molar Refractivity 94.54
TPSA ?

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

77.66 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.74
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

2.31
Log Po/w (WLOGP)?

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

2.77
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.

2.07
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

3.79
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.94

Water Solubility

Log S (ESOL):?

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

-2.84
Solubility 0.528 mg/ml ; 0.00144 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.

-3.58
Solubility 0.0966 mg/ml ; 0.000264 mol/l
Class?

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

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

-3.05
Solubility 0.324 mg/ml ; 0.000883 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

Yes
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

Yes
Log Kp (skin permeation)?

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

-6.9 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

1.0
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

2.0 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<2.0
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)

4.49

Application In Synthesis of [ 3130-19-6 ]

* 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 [ 3130-19-6 ]

[ 3130-19-6 ] Synthesis Path-Downstream   1~5

YieldReaction ConditionsOperation in experiment
Stage #1: bis((3,4-epoxycyclohexyl)methyl) adipate; pentaerythritol ethoxylate at 100℃; for 1h; Stage #2: at 80 - 150℃; for 4h; 6 EXAMPLE 6 A sample of bis(3,4-epoxycyclohexylmethyl)adipate carboxylate of epoxide content 4.9 mol/kg (78.3 g) and pentaerythritol ethoxylate (MW 770, 21.7 g) are heated at 100° C. under vacuum for 1 hour. The mixture is allowed to cool to 800° C. and then Amberlyst (TM) 15 ion exchange resin (30 g) added. This mixture is heated under vacuum at 150° C. for 4 hours by which time the epoxy value has fallen to 2.6 mol/kg. The reaction mixture is allowed to cool and the catalyst removed by filtration.
  • 2
  • [ 63905-29-3 ]
  • [ 3130-19-6 ]
YieldReaction ConditionsOperation in experiment
97.1% With dihydrogen peroxide; sodium acetate; acetic anhydride In chloroform; water at 40℃; for 0.333333h; 1-4 Example 1: Epoxidation reaction: 324.3 g of bis((3-cyclohexenyl)methyl) adipate obtained above was dissolved in 650 g of chloroform,Get solution two.37.7 g of anhydrous sodium acetate was dissolved in 321 g of a 50% aqueous solution of hydrogen peroxide (w/W).Get the solution three;The solution three and 311 g of acetic anhydride were pumped into the second mixer at a flow rate of 5.5 mL/min: 5 mL/min, respectively, and then mixed.Get the solution four;The solution 2 and the solution 4 were respectively pumped into the third mixer at a flow rate of 5.6 mL/min: 5.0 mL/min, and mixed.Then entering the second microchannel reactor,At a temperature of 40 ° C,Reaction for 20 minutes.After the reaction,Liquid separation,The lower organic phase is sequentially washed with water, alkali, washed with water and decomposed under reduced pressure.Bis((3,4-epoxycyclohexyl)methyl) adipate 343.6g,Test product refractionThe rate (n20/D) is 1.493 (lit.),The target product characteristic value;The molar yield was 97.1% (by bis((3-cyclohexenyl))(amount of adipate));Determine the epoxy equivalent of the above product according to the standard GB/T 4612-2008,Measured its epoxyThe equivalent value is 204.5g/eq; GC chromatographic analysis detects the purity of the product by 98.5%, as shown in Figure 2, using the area normalization method, retention time14min is the characteristic peak of the target product, and other small peaks are impurities or by-products. The analysis results are shown in the following table.GC chromatographic analysis results table
With dihydrogen peroxide; sodium acetate; acetic anhydride In chloroform at 13 - 20℃; for 8.5h; 2.1-2.4 The synthesis process of the diepoxide includes the following steps: (1) mixing a diene compound, a carboxylic acid substance, an alkaline salt, a solvent, and cooling to 13 ° C;(2) dropwise addition of hydrogen peroxide solution for 4.5h, and then continue the reaction for 4h, the temperature of the step is maintained at 20 ° C, the pH is maintained at 3.7;(3) standing, layering, obtaining the lower organic phase-1, adding the washing liquid, stirring for 30 min, washing the organic phase-1, maintaining the pH at 11; standing and layering, obtaining the lower organic phase-2;(4) First vacuum distillation purification, vacuum distillation under vacuum is -0.07MPa, temperature is 42 ° C, time is 0.75h, and then secondary film distillation purification, secondary film distillation temperature of the first film distillation is 50 ° C The distillation pressure was 220 Pa, the distillation time was 1 h, the secondary film distillation temperature was 90 ° C, the distillation pressure was 30 Pa, and the distillation time was 1 h.The diene compound isThe molar ratio of the carboxylic acid species to the diene compound was 2.35:1.The carboxylic acid substance is acetic anhydride, the acetic anhydride has a purity of 98%; the basic salt is sodium acetate; and the solvent is chloroform.The weight ratio of the diene compound to the solvent is 1:3.The concentration of the hydrogen peroxide was 35%; the molar ratio of the hydrogen peroxide to the diene compound was 3.6:1.The weight ratio of the washing liquid to the solvent was 1:3.The washing liquid includes an inorganic alkali solution and a reducing salt.The inorganic alkali solution is a sodium hydroxide solution; the concentration of the inorganic alkali solution is 30% by weight.The reducing salt is sodium sulfite; the reducing salt accounts for 1% by weight of the washing liquid.
With dihydrogen peroxide; acetic anhydride In water at 22 - 75℃; 4 Embodiment 4: bis(3,4-epoxycyclohexylmethyl)adipate (1) Reaction: dissolve the peroxide stabilizer in an aqueous solution of hydrogen peroxide (hydrogen peroxide 3.6eq) to obtain solution A; 3-cyclohexen-1-carboxylic acid-3-cyclohexen-1-methyl ester was dissolved in an organic solvent (olefin 1eq) to obtain solution B; Solution A and acetic anhydride (2.4eq) were pumped into the first continuous flow microstructure reactor by a precision metering pump, and the continuous reaction was carried out at a temperature of 45±2 °C for 60 seconds to obtain a peracid aqueous solution. The peracid aqueous solution and the solvent accurate metering pump were respectively pumped into the second continuous flow microstructure reactor and continuously extracted at 22±2 °C for 40s, and the extracted solution was passed through the continuous liquid-liquid separator to obtain the peracid organic solution. The peracid organic solution and solution B were respectively pumped into the third continuous flow microstructure reactor by a precision metering pump and subjected to a continuous reaction at 85±2 °C for 45 seconds to obtain the reaction solution. (0120) (2) Separation: The reaction liquid is continuously (semi-continuous) through the two-step process operation of quenching and cleaning through the continuous alkali washing tower and continuous water washing tower to obtain the clarified reaction solution. (0121) (3) Purification: Through reasonable flow control, the clarification reaction liquid passes through the continuous thin film evaporator (successively through the primary film evaporation and the secondary film evaporation) to realize the purification process operation and obtain the finished product. After the process is stabilized, it runs stably for 5 hours, and the reaction solution is collected every 1 hour after treatment, and the detection indicators are compared with the standard samples and/or literature for confirmation. (0122) (4) Maximization of resources: the alkaline water separated by quenching and extracting the acidic water can be neutralized and concentrated to obtain a saturated salt solution, and the crystalline water salt obtained by filtration after crystallization can be sold as a by-product. The water separated from the concentration, quenching and washing processes can be reused, in which the concentrated and separated water can be used for the cleaning process, and the water separated from the cleaning process can be used for the quenching process. The solvent recovered from the purification step can be recycled.
  • 3
  • [ 767-11-3 ]
  • [ 627-93-0 ]
  • [ 3130-19-6 ]
YieldReaction ConditionsOperation in experiment
90.1% With titanium tetra-n-butoxide at 105℃; for 8h; 4 Embodiment 4 In the 500L reactor, add 369.13kg 3,4-epoxycyclohexyl-1-methanol, 167.23kg dimethyl adipate, 18.5kg tetrabutoxide titanium; react at 105°C for 8 hours (there is no obvious liquid at this time) Evaporate, sample GC to detect 3,4-epoxycyclohexyl-1-methanol content≤1.0wt%), stop the reaction; The reaction solution is vacuumed at 300Pa, 105°C vacuum distillation to remove excess 3,4-epoxy ring Hexyl-1-methanol, the concentrated solution was distilled at 2Pa vacuum by molecular distillation, and distilled at 198°C under reduced pressure to obtain 317.0kg of bis((3,4-epoxycyclohexyl)methyl) adipate, molar yield: 90.1% ; Purity: 98.2%; Epoxy equivalent weight: 185g/mol, viscosity 575CP; The molar ratio of the above 3,4-epoxycyclohexyl-1-methanol, dimethyl adipate, and tetrabutoxytitanium is 3:1 : 0.06.
  • 4
  • [ 3130-19-6 ]
  • [ 79-10-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With triethylamine; triphenylphosphine at 90℃; Inert atmosphere; 3.a-3.d Example 3 (a) Put 144g of acrylic acid into a four-necked round-bottomed flask equipped with a stirrer and a thermometer, raise the temperature to 90°C and then dehydrate under reduced pressure;(b) Put in 1.5g triphenylphosphine and 1.0g triethylamine, and slowly drip in the alicyclic epoxy resin, the dripping time is about 2 hours, and pass in nitrogen for protection. The structural formula of the above alicyclic epoxy resin is:(c) After the alicyclic epoxy resin is dropped, add 500ppm hydroquinone and keep it warm for 30 minutes to measure the epoxy value;(d) Determine the epoxy value of the reaction to be 0.05 mol/100g, stop the reaction and cool to room temperature to discharge the material
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide In 1,2-dichloro-ethane at 60℃; for 4h; Inert atmosphere; 18 The reaction conditions are as follows: General procedure: In a 150mL stainless steel reactor, [BSIL]CuPW12O48(Cu-BSIL-POM-2) 0.20mmol, 50mL 1,2-dichloroethane, 30mmol double bond content in olefin and 50% hydrogen peroxide solution containing 30mmol H2O2, sealed reactor, nitrogen replacement three times, maintaining an inert gas atmosphere of nitrogen 0.5MPa, react at 60°C for 4h, at which time the catalyst precipitates from the reactionsystem, the relative hydrogen peroxide conversion rate of olefin and the selectivity of the corresponding epoxy compound are shown in the following table, the catalyst is recovered by filtration, and the obtained catalyst is vacuum dried at 50°C for 4h.
 

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