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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 75885-59-5
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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.
4.5
*For Research Use Only !
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 75885-59-5 |
Formula : | C6H10O2 |
M.W : | 114.14 |
SMILES Code : | CC1(C)CC1C(O)=O |
MDL No. : | MFCD04972493 |
InChI Key : | BFNMOMYTTGHNGJ-UHFFFAOYSA-N |
Pubchem ID : | 260708 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H227-H314 |
Precautionary Statements: | P210-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P370+P378-P403+P235-P405-P501 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅱ |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.83 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 30.35 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.39 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.08 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.12 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.89 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.07 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.16 |
Solubility | 7.86 mg/ml ; 0.0689 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.46 |
Solubility | 4.0 mg/ml ; 0.0351 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.56 |
Solubility | 31.5 mg/ml ; 0.276 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 |
-6.23 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 |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 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) |
1.39 |
* 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 |
---|---|---|
With potassium cyanide; sodium hydroxide; In pyridine; methanol; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; | First, 2,2-dimethyl-1,3-propane-ditosylate was synthesised by adding p-toluenesulfonyl chloride (1000 g, 5.25 mol) at 0 C. to a solution of neopentyl glycol (218 g, 2.1 mol) in 500 ml pyridine with stirring. The mixture was stirred for 1.5 hr and then poured into 1500 ml water in a slow stream while stirring vigorously. It was stirred for an additional 1.5 hr and then filtered. The crude solid was recrystallized from acetone (2.0 L), filtered, washed with water (2*0.5 L), hexane (1*0.5 L) and dried. Snow white solid (814 g) m.p. 120-121 C. 2,2-Dimethyl-cyclopropyl nitrile was synthesised by stirring the 2,2-dimethyl-1,3-propane-ditosylate prepared above (412 g, 1.0 mol) with KCN (195.4 g, 3.0 mol) in 2.0 L of ethylene glycol with heating (E. R. Nelson et al., JACS, 1957, p. 3467). At around 80 C., a clear solution was formed. The desired product began to distill out at about 175 C. The distillation was continued until the temperature reached 200 C. The distillate (300 ml) formed two layers. The upper layer was separated and the lower layer was extracted with hexane (3*200 ml). The combined extracts were dried over Na2CO3, concentrated and re-distilled at normal pressure. The yield was 41.7 g (43.8%), b.p. 151-152 C. 2,2-Dimethyl-cyclopropyl carboxylic acid was prepared by mixing 2,2-dimethyl-cyclopropyl nitrile (41.7 g, 0.43 mol) with sodium hydroxide (44 g, 1.05 mol) in water (100 ml) and methanol (50 ml). The mixture was heated to reflux for 48 hr until a clear solution formed. Methanol was distilled off and the aqueous portion was extracted with ether (50 ml) and the aqueous layer was diluted with water (500 ml) and carefully acidified with conc. HCl. The acidified mixture was extracted with ether (5*300 ml), CH2Cl2 (5*300 ml). The extract was evaporated to yield a liquid which was distilled to give 44.9 g (91.6%) of oil, b.p. 55-57 C. at 0.3 mm. 2,2-Dimethyl-cyclopropyl carboxylic acid chloride was prepared by mixing 2,2-dimethyl-cyclopropyl carboxylic acid (20.0 g, 0.18 mol) in CH2Cl2 (100 ml) with 45.7 g (0.36 mol, 31.4 ml) of oxalyl chloride. The mixture was stirred for 1.0 hr and then a small amount of DMF was added to ensure the completion of the reaction. The mixture was then distilled to give 17.8 g (75%) of the desired product, b.p. 84-87 C. Compound III.1, Bis-[4-(2',2'-dimethyl-cyclopropyl carboxy-amido phenol)]-methane, was prepared by combining a solution of 4,4'-methylenedianiline (0.67 g, 3.4 mol) and diisopropyl-ethyl-amine (1.94 g, 2.61 ml, 0.019 mol) in THF (10 ml). The mixture was treated slowly with a solution of 2,2-dimethyl-cyclopropyl carboxylic acid chloride (1.0 g, 7.5 mmol) in THF (10 ml). The reaction mixture was stirred for 1.0 hr and then decomposed with water (250 ml). The precipitated solid was filtered and washed with 10% HCl (10 ml), 10% sodium hydroxide (10 ml), water and ether. The yield was 1.2 g, m.p. 207-210 C. |
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