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Structure of Homopiperazine
CAS No.: 505-66-8
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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. : | 505-66-8 |
Formula : | C5H12N2 |
M.W : | 100.16 |
SMILES Code : | C1CNCCNC1 |
MDL No. : | MFCD00006933 |
InChI Key : | FQUYSHZXSKYCSY-UHFFFAOYSA-N |
Pubchem ID : | 68163 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H311-H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8(6.1) |
UN#: | 2923 |
Packing Group: | Ⅱ |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 37.47 |
TPSA ? Topological Polar Surface Area: Calculated from |
24.06 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.4 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.5 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.16 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.1 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.13 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.15 |
Solubility | 71.6 mg/ml ; 0.714 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.46 |
Solubility | 290.0 mg/ml ; 2.9 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.29 |
Solubility | 5.11 mg/ml ; 0.0511 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
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 |
-7.27 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 |
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) |
1.43 |
* 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 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; for 4.0h;Reflux; Inert atmosphere; | Step 4: 8-[l,4]Diazepan-l-yl-7-methoxy-quinolinehomopiperazine Pd2(dba)3, BINAP, NaOfBu, toluene [0154] A mixture of 8-bromo-7-hydroxyquinoline (126 g , 0.488 mol), homopiperazine (201g , 2.0 mol), (+/-)-BINAP (19.8 g , 31.8 mmol), and sodium tert-butoxide (75.6 g , 0.786 mol) was suspended in 900 mL of toluene and purged with nitrogen gas for an hour. Tris- benzylidineacetone dipalladium(O) (9.7 g, 10.6 mmol) was added. The mixture was purged for another hour, heated to reflux under nitrogen for 4 hr, cooled to rt, carefully diluted with 1300 mL of 20% AcOH in water and filtered through 100 g of celite. The celite pad was washed with 20% AcOH in water (IL x 2) and ethyl acetate (1 L x 1). The aqueous phase was extracted with ethyl acetate (I L x 4), adjusted to pH 10 -11 with NaOH (10 N, 500 mL), and then extracted with a mixture Of CH2Cl2 and iPrOH (80:20, 1 L x 2 and 0.5 L x 4). The combined organic phase was washed with saline (400 mL), dried over Mg2SO4 and evaporated to give the desired product (98 g). |
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