Structure of Methyl 5-Bromovalerate
CAS No.: 5454-83-1
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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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CAS No. : | 5454-83-1 |
Formula : | C6H11BrO2 |
M.W : | 195.05 |
SMILES Code : | O=C(OC)CCCCBr |
MDL No. : | MFCD00000265 |
InChI Key : | RAVVJKCSZXAIQP-UHFFFAOYSA-N |
Pubchem ID : | 79557 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.83 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 40.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.87 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.72 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.79 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.73 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.83 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.9 |
Solubility | 2.47 mg/ml ; 0.0127 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.04 |
Solubility | 1.76 mg/ml ; 0.00904 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.43 |
Solubility | 0.723 mg/ml ; 0.00371 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 |
-6.16 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 |
1.0 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) |
2.12 |
* 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 |
---|---|---|
100% | Step 10a: Ethyl 4-(benzyloxy)-3-(5-methoxy-5-oxopentyloxy)benzoate (Compound 503-18) The title compound 503-18 (1.5 g, 100%) was prepared as a yellow oil from compound 502 (1.0 g, 3.7 mmol), methyl 5-bromopentanoate (1.0 g, 4.4 mmol) using a procedure similar to that described for compound 307-9 (Example 3): LCMS: 437 [M+23]+; 1H NMR (DMSO-d6): delta 7.54 (d, J=8.7 Hz, 1H), 7.44-7.33 (m, 6H), 7.14 (d, J=8.4 Hz, 1H), 5.18 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.01 (t, J=6.0 Hz, 2H), 3.56 (s, 3H), 2.33 (m, 2H), 1.80-1.61 (m, 4H), 1.28 (t, J=7.2 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In water; N,N-dimethyl-formamide; | Example 1 Synthesis of 5-(2-tert-Butyl-4-chlorophenoxy)pentanoic Acid Methyl 5-bromovalerate (1.52 mL, 2.09 g, 10.7 mmol), 2-tert-butyl-4-chloro-phenol (2.4 g, 13 mmol) and potassium carbonate (1.4 g, 10.1 mmol) were suspended in dry DMF (10 mL) and stirred for 2 h at 120 C. To the resulting mixture water was added (80 mL) and extracted with ethyl acetate (3*20 mL). The organic layers were washed two times with 10% sodium hydroxide (2*20 mL), water (1*20 mL), dried over sodium sulfate and evaporated in vacuo. To afford 3.46 g (quant) crude la that was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) delta ppm 7.21 (d, J=2.6 Hz, 1H), 7.10 (dd, J=8.6, 2.6 Hz, 1H), 6.75 (d, J=8.6 Hz, 1H), 3.97 (t, J=5.8 Hz, 2H), 2.46 (t, J=6.9 Hz, 2H), 1.84-1.94 (m, 4H), 1.36 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong> 1 (HHTP) was prepared according to the reported procedure [34]. To give compounds 2, 3 and 4, th e mixture of HHTP (1 mmol) and K2CO3 (8 mmol) in 50.0 mL of dry acetone was refluxed for 1 h. Then, ethyl bromoacetate, methyl 5-bromovalerate or methyl (4-bromomethyl)benzoate (8 mmol) upon this solution were added and refluxed for 24 h. The reactionwas monitored by TLC. The resulting solutionwas allowed to warm up to room temperature. At the end of the reaction, the reaction mixture was filtered and the organic layer was removed under reduced pressure. The observed solid product was dissolved in CHCl3 and washed twice with 0.2 N HCl and water. The combined organic phase was dried over Na2SO4 filtered, andconcentrated under reduced pressure to afford the desired pure product (2, 3 and 4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.3 g | With triethylamine; In N,N-dimethyl-formamide; at 80 - 90℃; | a: Compound 1 (10.0 g), methyl 5-bromovalerate (8.5 g), triethylamine (2.7 g) were added to DMF (20 mL),Keep warm at 80-90C until the reaction of compound 1 is complete. After cooling down to 20-30C,The reaction solution was slowly poured into 200 mL of water and the precipitated white solid was collected by suction filtration under reduced pressure.After drying, 10.3 g of compound 3 was obtained. |