Structure of 15666-97-4
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
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 !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
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.
Batch number can be found on the product's label following the word 'Batch'.
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.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 15666-97-4 |
Formula : | C11H19NO2 |
M.W : | 197.27 |
SMILES Code : | O=C(OCCCCCCCC)CC#N |
MDL No. : | MFCD00075425 |
InChI Key : | MBCTWXWDQMXVDF-UHFFFAOYSA-N |
Pubchem ID : | 4384482 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.82 |
Num. rotatable bonds | 9 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 56.02 |
TPSA ? Topological Polar Surface Area: Calculated from |
50.09 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.3 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.8 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.8 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.7 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.55 |
Solubility | 0.558 mg/ml ; 0.00283 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.03 |
Solubility | 0.0185 mg/ml ; 0.0000939 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.29 |
Solubility | 0.102 mg/ml ; 0.000519 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 |
-5.16 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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.3 |
* 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 toluene-4-sulfonic acid; In toluene; at 80 - 125℃; | In step 1 of Figure 1, in a 1 liter round bottom flask, 136 g of 1-octanol was mixed with 350 g of toluene, the flask was placed in a heating mantle and maintained on a magnetic stirrer,The mixture was stirred vigorously at 80 DEG C to form a mixed solution.As step 120 of Figure 1,86 g of 2-cyanoacetic acid and 0.5 g of p-toluenesulfonic acid were gradually added to the flask, and a water condenser was connected to the flask through a trap and a calcium chloride guide tube.The temperature was 125 CAnd the esterification reaction was carried out.As step 130 of Figure 1, the water formed during the esterification reaction was azeotrope-formed and removed while azeotropic distillation was continued until the total amount of water collected was 17 mL. The distillation was then stopped and the flask was cooled to room temperature. The contents of the flask were filtered with a Buchner funnel, and the filtrate was extracted three times with a 10% sodium hydrogencarbonate solution and water using a 1 liter separatory funnel, respectively. The obtained organic layer was dried over anhydrous magnesium sulfate for 12 hours.Then toluene was added to 85In And then removed by rotary evaporation.Results 1-Octyl-2-cyanoacetate was analyzed by FT-IR spectrophotometer and the results are shown in FIG. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With lithium diisopropyl amide; In tetrahydrofuran; at -78℃; for 0.75h; | Preparation of aryl-bis-(2-cyano-3-hydroxy-acrylic acid) ester (102): R = N-OCTYL, I-OCTYL (102) A 1.6 m solution MMOL of n-BuLi in hexane is added at-10C to a solution of 1 mmol diiso- propylamine in THFabs (6 ML/ML DIISOPROPYLAMINE). The mixture is stirred for 15 min. and than cooled down to-78C. After that the solution of 0.5 mmol of the corresponding cyano acetate is added in THF (1 MI/ g cyanoacetate) at this temperature initially, additionally stirred for 15 min and than the SOLU- tion of 0.5 mmol of the acid chloride is added in THF (2 ML/G acid chloride). After stirring of 45 min AT-78C the reaction mixture is quenched at this temperature with 15 % HCI und warmed up to room temperature over night. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine; In chloroform; at 20℃; for 40h;Inert atmosphere; | Under argon gas protection, to a two-ported flask filled with 3T(BDT)3T(CHO)2 (1.0 g, 0.71 mmol), <strong>[15666-97-4]octyl cyanoacetate</strong> (10-folds molar equivalent) and 70 mL of dry trichloromethane was added dropwise several drops of triethylamine. The mixture was stood at room temperature for 40 h and then was poured into 100 mL of water and extracted with dichloromethane (50 mL×3). The organic phase was washed with water (100 mL), saturated saline (100 mL) and water (100 mL), successively. The organic phase was dried over anhydrous sodium sulfate. After the solvent was removed under reduced pressure, the resultant product was separated with chromatographic column, in which petroleum ether-dichloromethane (2:3) was eluant, to give a black solid (yield: 70%). MALDI-TOF MS (m/z): C106H148N2O4S8 [M]+, calculated: 1768.92; found: 1768.93. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With trifluoroacetic acid; In dichloromethane; at 22℃;Product distribution / selectivity; | To a solution of octyl triflate (0.05 mol) in dry dichloromethane (DCM, 100 mL) was added trifluoroacetic acid [TFA] (0.004 mol) and t-butylated hydroxyanisole (0.25 wt%). A solution of Dicyclohexylammonium alpha-cyanoacrylate in dry DCM (80mL) was added dropwise (2h). The resulting solution was stirred at 22 C overnight. NMR showed approx 10% of the triflate remaining with no trace of polymer. A solution of 0.078 mol of Dicyclohexylammonium alpha-cyanoacrylate in dry DCM (20 mL) was added. The mixture was stirred at 22 C until triflate had disappeared in the NMR (4h). The mixture was acidified (TFA) and reduced in vacuo. The precipitated solid was removed by filtration. Hexane (100 mL) was added. The mixture was reduced and filtered again. This was repeated. The solvents were removed to afford 1 1.5g of a yellow liquid which was -75- 80% CA monomer. The impurities are cyanoacrylic acid (due to the excess ofDicyclohexylammonium alpha-cyanoacrylate used), dioctyl ether (a byproduct carried through from the triflate formation) a small amount (<2%) of polymer, trace amounts of the amine triflate salt, octyl cyanoacetate (formed from cyanoacetic acid amine salt, a residue from incomplete formation of the Dicyclohexylammonium alpha-cyanoacrylate). There are no byproducts or side reaction evident from the CA formation reaction. The octyl CA was distilled to purify and afforded an overall yield of 65% based on triflate. The synthesis procedure is general and has been used to prepare crude samples of other monomers such as n-propyl CA, 3-methoxybutyl CA and bis-cyanoacrylic acid ester of PEG 400.[0060] NMR Analysis of distilled material: 1H NMR (CDCI3) delta : 7.05, (s, 1 H, =CHH); 6.65 (s, 1 H, =CHH); 4.27 (t, 2H, ~COOCH2CH2~); 1.73 (m, 2H, ~COOCH2CH2~); 1 .40-1.25 (br m, 10H, ~COOCH2CH2CH2CH2 CH2CH2CH2~); 0.88 (t, 3H, ~CH2CH3).[0061] 13C 5 : 163.27 ~COO~; 143.3, =CH2; 1 14.5, ~CN; 1 13.4, ~C=CH2; 66.99, ~COOCH2~; 31 .8; 29.2; 28.4; 25.8; 24.7; 22.7 (~CH2CH3); 14.1 1 (~CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triethylamine; In chloroform; at 20℃;Inert atmosphere; | Under argon gas protection, to a two-neck flask filled with bis(formyltrithiophene)silole (147 mg, 0.104 mmol), <strong>[15666-97-4]octyl cyanoacetate</strong> (10-folds molar equivalent) and 50 mL of dry trichloromethane was added dropwise several drops of triethylamine. The mixture was stirred at room temperature overnight. The mixture was poured into 100 mL of water and extracted with dichloromethane (20 mL×3). The organic phase was washed with water (50 mL), saturated saline (50 mL) and water (50 mL), successively. The organic phase was dried over anhydrous sodium sulfate. After the solvent was removed under reduced pressure, the resultant product was separated with chromatographic column, in which petroleum ether-dichloromethane (1:1) was eluant, to give a brown solid (yield: 90%). MALDI-TOF MS (m/z): C90H124N4O6S7 [M]+, calculated: 1773.9; found: 1773.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 40% | With triethylamine; In chloroform; at 75℃; for 24h;Reflux; | To a solution of residue Compound 5 (0.9 g, 1.00 mmol) in 50 mL of chloroform, <strong>[15666-97-4]octyl cyanoacetate</strong> (1.97 g, 10.0 mmol) and 1.5 ml triethylamine were added and the mixture was refluxed at 75 C for 24 h under nitrogen. After returning to room temperature dichloromethane was added, the solution was washed with water and dried over Na2SO4. After solvent removal, the residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate 1:1) to give 575 mg of black solid with a yield of ca. 40%. MALDI-TOF MS: 1436.3, calculated for C84H84N4O6S6 1436.47. 1H NMR (400 MHz, CDCl3): delta(ppm) 8.25 (s, 3H), 7.67-7.66 (d, J = 4.0 Hz, 3H), 7.41-7.38 (d, J = 8.0 Hz, 6H), 7.32-7.30 (d, J = 8.0 Hz, 3H), 7.25-7.23 (d, J = 6.0 Hz, 3H), 7.12-7.08 (d, J = 8.6 Hz, 9H), 7.04-7.00 (d, J = 10.0 Hz, 3H), 6.96-6.91 (d, J = 12.0 Hz, 3H), 4.31-4.27 (t, 6H), 1.79-1.71 (m, 6H), 1.42-1.40 (m, 6H), 1.32-1.29 (d, J = 10.0 Hz, 24H), 0.91-0.87 (t, 9H). 13C NMR (400 MHz, CDCl3): delta(ppm) 163.14, 147.55, 146.09, 145.55, 139.24, 134.24, 133.94, 127.70, 127.26, 124.43, 124.24, 116.14, 97.62, 66.65, 31.83, 29.24, 29.21, 22.70, 14.17. |
A183042 [141942-85-0]
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate
Similarity: 0.79
A183042 [141942-85-0]
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate
Similarity: 0.79
A183042 [141942-85-0]
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate
Similarity: 0.79