Structure of 85-42-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 85-42-7 |
Formula : | C8H10O3 |
M.W : | 154.16 |
SMILES Code : | O=C1OC(C2CCCCC21)=O |
MDL No. : | MFCD00064863 |
InChI Key : | MUTGBJKUEZFXGO-UHFFFAOYSA-N |
Pubchem ID : | 85689 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H317-H318-H334 |
Precautionary Statements: | P261-P272-P280-P285-P302+P352-P304+P341-P305+P351+P338-P310-P333+P313-P342+P311-P363-P501 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.75 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 37.83 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.36 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.18 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.88 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.39 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.55 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.27 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.54 |
Solubility | 4.45 mg/ml ; 0.0289 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.69 |
Solubility | 3.17 mg/ml ; 0.0206 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.14 |
Solubility | 11.2 mg/ml ; 0.0726 mol/l |
Class? Solubility class: Log S scale |
Soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.4 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.62 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
tin oxide; In xylene; at 225 - 230℃; under 150.015 Torr; for 5 - 8h;Dean-Stark trap;Product distribution / selectivity; | [0472] Purified di(3,5,5-trimethylhexyl) 1,2-cyclohexanedicarboxylate was produced by the same procedure as in Example I-7 with the exception of using <strong>[3452-97-9]3,5,5-trimethylhexanol</strong> having a peroxide value of 0.4 meq/kg and a carbonyl value of 0.3 (the same as used in Example I-4). Subsequently dehydration was carried out at 130° C. under a reduced pressure of 1330 Pa for 5 hours. [0473] The total acid number and kinematic viscosity of the obtained ester are shown in Table 1. The ester had a hue of 10 in terms of Hazen color number, a water content of 28 ppm, a sulfated ash content of less than 1 ppm, a sulfur content of less than 1 ppm, a phosphorus content of less than 1 ppm, a hydroxyl value of 0.9 mgKOH/g, a peroxide value of 0.5 meq/kg and a carbonyl value of 0.2.; Example I-9 [0474] When <strong>[3452-97-9]3,5,5-trimethylhexanol</strong> was stored at room temperature for one year, it showed a peroxide value of 0.8 meq/kg and a carbonyl value of 17.2. The same procedure as in Example I-8 was performed with the exception of using said <strong>[3452-97-9]3,5,5-trimethylhexanol</strong>, thereby producing purified di(3,5,5-trimethylhexyl) 1,2-cyclohexanedicarboxylate. Then dehydration was carried out at 130° C. under reduced pressure of 1330 Pa for 5 hours. [0475] The total acid number and kinematic viscosity of the obtained ester are shown in Table 1. The ester had a hue of 30 in terms of Hazen color number, a water content of 23 ppm, a sulfated ash content of 4 ppm, a sulfur content of less than 1 ppm, a phosphorus content of less than 1 ppm, a hydroxyl value of 1.2 mgKOH/g, a peroxide value of 1.0 meq/kg and a carbonyl value of 9.8.; Example I-10 [0476] When <strong>[3452-97-9]3,5,5-trimethylhexanol</strong> was stored at room temperature for one year, it showed a peroxide value of 0.8 meq/kg and a carbonyl value of 17.2. Following the procedure of Example I-8 and using the <strong>[3452-97-9]3,5,5-trimethylhexanol</strong>, the starting materials were gradually heated to 225° C. in the presence of tin oxide catalyst (0.2 wt. percent based on the starting materials fed) in a nitrogen atmosphere. While water generated during the reaction was removed by means of water separator, the esterification reaction was conducted for 6 hours and at 225° C. under reduced pressure (20000 Pa) for 2 hours. [0477] After the reaction, excess <strong>[3452-97-9]3,5,5-trimethylhexanol</strong> was removed by distillation at 210° C. under a reduced pressure of 1330 Pa, and the obtained liquid residue was neutralized by adding thereto 33 g of a 4percent aqueous solution of sodium hydroxide and stirring the mixture at 80° C. for 2 hours, and then washed with water until the aqueous layer became neutral to thereby give a liquid crude ester. At this point, the crude ester had a total acid number of 0.01 mgKOH/g. Subsequently, to the ester was added activated alumina ("Tomita-AD 220P" manufactured by Tomita Pharmaceutical Co., Ltd.; 0.2 wt. percent based on the starting materials fed) and activated clay ("Galleon-earth V1" manufactured by Mizusawa Industrial Chemicals Ltd.; 0.2 wt. percent based on the starting materials fed), and the mixture was stirred at 90° C. and at 1330 Pa for 1 hour and filtered, whereby 390 g of purified di(3,5,5-trimethylhexyl) 4-cyclohexene-1,2-dicarboxylate was obtained. Dehydration was carried out at 130° C. under a reduced pressure of 1330 Pa for 5 hours. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[0676] In the same manner as in Example II-15, a reaction was carried out using 154.1 g (1 mole) of 1,2-cyclohexanedicarboxylic anhydride (prepared by hydrogenating 4-cyclohexene-1,2-dicarboxylic anhydride obtained by usual Diels-Alder reaction of maleic anhydride and 1,3-butadiene) and 74 g (1 mole) of isobutanol with a peroxide value of 0.1 meq/kg and a carbonyl value of 0.1 as alcohol component 1, whereby the total acid number of the reaction mixture became 246 mgKOH/g (theoretical value: 246 mgKOH/g). [0677] Then, to the reaction mixture was added tin oxide (0.2 wt. percent based on the starting materials fed) as a catalyst, and at 220° C., 7.4 g (0.1 mole) of said isobutanol and 158.4 g (1.1 moles) of <strong>[3452-97-9]3,5,5-trimethylhexanol</strong> with a peroxide value of 0.1 meq/kg and a carbonyl value of 0.2 as alcohol component 2 were further added dropwise. While water generated during the reaction was removed by water separator, the esterification reaction was carried out at 220° C. for about 9 hours until the total acid number of the reaction mixture became 3 mgKOH/g or less, and further continued at 220° C. and at 20000 Pa for 1 hour. [0678] After the reaction, the excess alcohols were removed by distillation at 180° C. under a reduced pressure of 1330 Pa, and the obtained liquid residue was neutralized by adding thereto 27 g of a 4percent aqueous solution of sodium hydroxide and stirring the mixture at 80° C. for 2 hours, and then washed with water until it became neutral, giving a crude ester mixture. At this point, the crude ester mixture had a total acid number of 0.01 mgKOH/g. Subsequently, to the crude ester mixture was added activated carbon ("Shirasagi M" manufactured by Sumitomo Chemical Co., Ltd.; 0.1 wt. percent based on the starting materials fed), and the mixture was stirred at 90° C. and at 1330 Pa for 1 hour and filtered, whereby 320 g of a purified ester mixture containing (isobutyl)(3,5,5-trimethylhexyl) 1,2-cyclohexanedicarboxylate was obtained. Dehydration was carried out at 100° C. under a reduced pressure of 1330 Pa for 6 hours. The total acid number and kinematic viscosity of the obtained ester are shown in Table 6. [0679] The ester mixture had a water content of 12 ppm, a sulfated ash content of less than 1 ppm, a sulfur content of less than 1 ppm, a phosphorus content of less than 1 ppm, a hydroxyl value of 0.2 mgKOH/g, a peroxide value of 0.1 meq/kg and a carbonyl value of 0.2. The obtained ester mixture had a cis:trans isomer ratio of 38:62 (area percent), as determined from the gas chromatogram thereof. Further, the obtained ester mixture was found to be a mixture of the following esters from the gas chromatogram thereof: [0680] (1) diisobutyl 1,2-cyclohexanedicarboxylate [0681] (2) (isobutyl)(3,5,5-trimethylhexyl) 1,2-cyclohexanedicarboxylate [0682] (3) di(3,5,5-trimethylhexyl) 1,2-cyclohexanedicarboxylate [0683] (1)/(2)/(3)=21.9/44.2/33.9 (area percent) |