Home Cart Sign in  
Chemical Structure| 13361-34-7 Chemical Structure| 13361-34-7

Structure of 13361-34-7

Chemical Structure| 13361-34-7

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 13361-34-7 ]

CAS No. :13361-34-7
Formula : C11H19NO2
M.W : 197.27
SMILES Code : O=C(OCC(CC)CCCC)CC#N
MDL No. :MFCD00019843
InChI Key :ZNYBQVBNSXLZNI-UHFFFAOYSA-N
Pubchem ID :96359

Safety of [ 13361-34-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501

Computational Chemistry of [ 13361-34-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 0
Fraction Csp3 0.82
Num. rotatable bonds 8
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 56.02
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

50.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.54
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.13
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.66
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.88
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.63
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.57

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.51
Solubility 0.614 mg/ml ; 0.00311 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.85
Solubility 0.0278 mg/ml ; 0.000141 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.91
Solubility 0.242 mg/ml ; 0.00123 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.28 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.75

Application In Synthesis of [ 13361-34-7 ]

* 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.

  • Downstream synthetic route of [ 13361-34-7 ]

[ 13361-34-7 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 32161-06-1 ]
  • [ 13361-34-7 ]
  • 6-acetyl-2-amino-4,5,6,7-tetrahydro-thieno[2,3-<i>c</i>]pyridine-3-carboxylic acid 2-ethyl-hexyl ester [ No CAS ]
  • 2
  • [ 13361-34-7 ]
  • [ 774584-07-5 ]
  • 2-cyano-3-[2-(2-hydroxyphenyl)bezoxazol-6-yl]acrylic acid 2-ethylhexyl ester [ No CAS ]
  • 3
  • [ 13361-34-7 ]
  • 6-acetyl-2-isobutyrylamino-4,5,6,7-tetrahydro-thieno[2,3-<i>c</i>]pyridine-3-carboxylic acid 2-ethyl-hexyl ester [ No CAS ]
  • 4
  • [ 556-18-3 ]
  • [ 13361-34-7 ]
  • [ 479053-95-7 ]
YieldReaction ConditionsOperation in experiment
66% acetic acid; diethylamine; In 2-methyl-propan-1-ol; for 9h;Heating / reflux; 4-Aminobenzaldehyde oligomer (36.3 g, 0.3 mol) is suspended in 450 ml of isobutanol. 2-ethylhexyl cyanoacetate (59.1 g, 0.3 mol) and a catalyst consisting of diethylamine (0.375 ml) and of acetic acid (1.12 ml) are added thereto. The mixture is refluxed for 5 hours. A second addition of catalyst was performed and the reaction mixture refluxed for a further 4 hours. A light amount of insoluble material is filtered off while hot. After cooling the filtrate, it is concentrated to a volume of 300 ml and allowed to crystallize under cold conditions. After drying, 59.6 g (yield: 66%) of the expected derivative are obtained in the form of an orange-coloured solid.
  • 5
  • [ 556-18-3 ]
  • [ 109-89-7 ]
  • [ 13361-34-7 ]
  • 2-ethylhexyl 3-(4-aminophenyl)-2-cyanoacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With acetic acid; In isopropyl alcohol; a) Preparation of 2-ethylhexyl 3-(4-aminophenyl)-2-cyanoacrylate 36.3 g (0.3 mol) of p-aminobenzaldehyde are suspended in 450 ml of isopropanol. A mixture of 59.1 g (0.3 mol) of 2-ethylhexyl cyanoacetate and of catalyst (0.375 ml of diethylamine and 1.125 ml of acetic acid) is introduced therein. The mixture is refluxed for 5 hours. The same amount of catalyst is added again and refluxing is continued for a further 4 hours. The insoluble materials are removed by hot filtration and the mixture is concentrated to a volume of 300 ml and left to crystalize. After filtration and drying, 59.6 g (66% yield) of an orange-coloured powder are obtained, and are used without further purification for the following step.
  • 6
  • [ 122-85-0 ]
  • [ 13361-34-7 ]
  • 2-ethylhexyl 3-(4-acetylaminophenyl)-2-cyanoacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% In isopropyl alcohol; a) Preparation of 2-ethylhexyl 3-(4-acetylaminophenyl)-2-cyanoacrylate A mixture of 35 g (0.18 mol) of 2-ethylhexyl cyanoacetate and 30 g (0.18 mol) of 4-acetamidobenzaldehyde in 300 ml of isopropanol is refluxed for 3 hours. The reaction mixture is then allowed to cool and is crystallized. The crystals formed are separated out by filtration and are recrystallized from a minimum amount of isopropanol. After filtration and drying, 33.3 g (54% yield) of 2-ethylhexyl 3-(4-acetylaminophenyl)-2-cyanoacrylate are obtained in the form of a pale yellow powder. Melting point: 119 C. UW absorption (as a solution in ethanol): λmax=351 nm, εmax=30 960, EI %=904 Elemental analysis for C20H26N2O3 calculated: C 70.15; H 7.65; N 8.18; O 14.02 found: C 70.08; H 7.65; N 8.16; O 14.03
  • 7
  • [ 104-76-7 ]
  • [ 372-09-8 ]
  • [ 13361-34-7 ]
YieldReaction ConditionsOperation in experiment
92% With toluene-4-sulfonic acid; In water; at 110℃; under 760.051 Torr; for 1h;Heating / reflux; To a 1000 ml four neck flask fitted with mechanical agitator, thermometer, Dean and Stark apparatus and water condenser, add 237.5g (2.23 mol on pure substance) 80 wt.-% cyanoacetic acid in water, 44Og (3.38 mol) 2-ethylhexanol and 1.2g (6.3 mmol) p-toluenesulfonic acid monohydrate. Afterwards, the mixture is heated to reflux (1 100C) under atmospheric pressure for 1 hour and the water (both initial and formed) is azeotropically distilled out using a Dean and Stark apparatus returning the upper organic layer to the reactor. After 1 hour and at a temperature of 1300C gradually a vacuum of 400 mbar is applied using a water respirator. The azeotropic distillation is maintained for further 6 hours while gradually increasing the vacuum from 400 mbar to 30 mbar in order to maintain a temperature of 1300C until no further water is removed. After releasing the vacuum the reaction mixture is cooled to 900C. After the addition of about 100ml water (pre heated to 900C), the mixture is stirred at 85-900C for 10 minutes before separation of the phases. The upper organic layer is transferred to a 1000 ml four neck flask fitted with mechanical agitator, thermometer, packed column (ID=30mm, H=I 200mm, packing metal raschid rings D=7mm), water condenser and distillate flasks. Excess 2-Ethylhexanol is distilled out at 130- 1400C under a vacuum of 10-30 mbar. When complete increase the vacuum to 1.5 mbar and distilled out 2-ethylhexyl cyanoacetate at 130-1400C. 2-Ethylhexyl cyanoacetate is obtained as a colourless liquid. The reaction yield is 92% (based on cyanoacetic acid).
  • 8
  • [ 119-61-9 ]
  • [ 13361-34-7 ]
  • [ 6197-30-4 ]
YieldReaction ConditionsOperation in experiment
76.3% With ammonium acetate; acetic acid; In water; at 85 - 90℃; under 400 - 420 Torr; for 16h; A 1000 mL four neck round bottom flask, equipped with a mechanical stirrer, a thermometer and a condenser, was charged with 2-ethylhexyl cyanoacetate (347 g, 1.76 gmol), benzophenone (200 g, 1.1 gmol) , recovered acetic acid (168.3 g containing 2% water, 2.75 gmol) and ammonium acetate (3 lg, 0.4 gmol). The stirred reaction mass was then heated to 85-90C. Azeotrope of acetic acid/water mixture was distilled off oyer a period of 16 h. under reduced pressure from 400-420 mm of Hg A till the Gas chromatographic analysis showed no further decrease in benzophenone concentration in reaction mass. The loss of acetic acid was continuously adjusted by adding the corresponding recovered acetic acid. The acetic acid was then recovered under reduced pressure (30-60 mm of Hg A). The HPLC analysis of reaction mass showed BPCA content of 0.19%. The crude reaction mixture was cooled and washed twice with 300 g portion of water and subsequently distilled to yield pale yellow colored viscous liquid (303 g, Yield 76.3%) which was found to be of 99.48% purity by Gas chromatographic analysis.
66.18 - 93.09% With propionic acid;ammonium acetate; In n-heptane; at 110℃; under 760.051 Torr; for 5h;Product distribution / selectivity; Into a 500ml four-neck round-bottom flask, equipped with a mechanical stirrer, a thermometer and a condenser is charged with 62.2 g (0.32mol) of 2-Ethylhexyl cyanoacetate (EHCA) and 81.Og (0.45 mol) of Benzophenone (BP) (molar ratio EHCA:BP = 0.71 : 1) and 27.7g (0.36 mol) of ammonium acetate and 81.0g (1.1 mol) of propionic acid and 81.0g of heptane. The mixture is heated under stirring. When the temperature reach H O0C, a mixture of propionic acid, water, heptane is distilled off over a period of 5 hours at normal pressure. Heptane phase is returned back to the flask. Then the reactant is cooled to 900C, and 100 ml of hot water is added to the reaction mixture. The mixture is kept at 85C for 10 minutes, and then transferred to a funnel for separation. To a flask equipped with a column 256.Og of crude 2-ethylhexyl 2-cyano-3,3- diphenylacrylate solution is added. Rectification is carried out at 1 mbar. 2-Ethylhexyl 2-cyano- <n="9"/>3,3-diphenylacrylate is distilled out at 2100C (vapor). After distillation, light yellow 2-ethylhexyl 2-cyano-3,3-diphenylacrylate is obtained. Reaction yields are as indicated in table 1 and assume recycle of unreacted benzophenone and 2-EHCA.The experiment is repeated by adjusting the amount of 2-EHCA in order to give the molar ratios as indicated in the table 1 below.
  • 9
  • [ 119-61-9 ]
  • [ 13361-34-7 ]
  • [ 731-48-6 ]
  • [ 6197-30-4 ]
YieldReaction ConditionsOperation in experiment
0.42 - 0.7%Chromat. With propionic acid;ammonium acetate; In n-heptane; at 95 - 110℃; under 525.053 - 760.051 Torr; for 6h;Heating / reflux;Product distribution / selectivity; A 2000ml reactor is charged with 3 U g of 2-ethylhexyl cyanoacetate, 70 g of ammoniumacetate, 404 g of benzophenones, 405 g of propionic acid and 405 g of n-heptane. The mixture is heated to about 950C under stirring at reduced pressure (about 700 mbar in order to maintain the reaction at reflux). When the temperature reached 950C a mixture of heptane, water and propionic acid is distilled off azeotropically over a period of 6h wherein the organic phase is recharged back in the reactor. During this time every hour 25 g of additional ammonium acetate is added stepwise (5 portions, 1 per hour). After the reaction is finished heptane and propionic acid are distilled off at reduced vacuum (up to 20 mbar while keeping the temperature below about 95C). When no more distillate is observed, 500g of water is added and the mixture is stirred for 10 min at 75C. After adding 340 g of n-heptane the organic phase is collected and the washing procedure is repeated. After evaporation of the solvent at reduced pressure (temperature is maintained below 95C) the crude product (comprising about 0.04 % of 2-cyano-3,3-diphenyl-2-propenamide) is collected followed by distillation using a wiped thin film evaporator. A second distillation yielded 388 g of light yellow octocrylene comprising about 0.38 % of 2-cyano-3,3-diphenyl- 2-propenamide (determined via HPLC). The reaction is repeated at normal pressure and a temperature of about HO0C (reflux temperature) resulting after purification in an amount of 0.7 % of 2-cyano-3,3- diphenyl- 2-propenamide
  • 10
  • [ 109-89-7 ]
  • [ 4485-89-6 ]
  • [ 13361-34-7 ]
  • C18H30N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.5% [N- (3-ANILINO-ALLYLIDENE)-ANILINE] (4.5 g, 0.02 mol) and cyanoacetic acid 2-ethylhexyl ester (4.2 g, 0.021 mol) are stirred in 10 ml of acetanhydride for 2 hours at [85-90XB0;C.] After removing the excess of acetanhydride in vacuo, the reaction batch is poured onto ice, and the resulting precipitate is filtered off and washed with copious amounts of water. After drying in vacuo at [60XB0;C,] the intermediate product is taken up in 10 ml of dry ethanol, and diethylamine (3.1 g, 0.042 mol) is added. The reaction mixture is stirred for 2 hours at 50- [55XB0;C.] The ethanol and the excess of amine are then distilled off in vacuo. The residue, in a mixture of toluene and acetone (9.5 : 0.5), is subjected to fractionated filtration over silica gel 60 from Merck and isolated. The pure product is dried under a high vacuum at [60XB0;C.] Yield : 4.5 g (73.5 % of theory).
  • 11
  • [ 110-85-0 ]
  • [ 4485-89-6 ]
  • [ 13361-34-7 ]
  • C32H48N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% [N- (3-ANILINO-ALLYLIDENE)-ANILINE] (4.5 g, 0.02 mol) and cyanoacetic acid 2-ethylhexyl ester [(4. 2] g, 0.021 mol) are stirred in 10 ml of acetanhydride for 2 hours at [85-90XB0;C.] After removing the excess of acetanhydride in vacuo, the reaction batch is poured onto ice, and the resulting precipitate is filtered off and washed with copious amounts of water. After drying in vacuo at [60XB0;C,] the intermediate product is taken up in 10 mi of dry ethanol, and piperazine (0.8 g, 0.01 mol) is added. After stirring for 2 hours at [50-55XB0;C,] the ethanol is distilled off in vacuo. Subsequent column chromatography over silica gel 60 from Merck using a mixture of toluene and acetone (9: 1) yields the pure product, which is [DRIED IN VACUO] at [60XB0;C.] Yield : 3.9 g (69 % of theory).
  • 12
  • [ 10061-68-4 ]
  • [ 4485-89-6 ]
  • [ 13361-34-7 ]
  • C35H56N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% [N- (3-ANILINO-ALLYLIDENE)-ANILINE] (4.5 g, 0.02 mol) and cyanoacetic acid 2-ethylhexyl ester (4.2 g, 0.021 mol) are stirred in 10 ml of acetanhydride for 2 hours at [85-90XB0;C.] After removing the excess of acetanhydride in vacuo, the reaction batch is poured onto ice, and the resulting precipitate is filtered off and washed with copious amounts of water. After drying in vacuo at [60XB0;C,] the intermediate product is taken up in 10 ml of dry ethanol, and diethyl- 1,3-propanediamine (1.3 g, 0.01 mol) is added. The reaction mixture is stirred for 2 hours at [50XB0;C.] The ethanol is then distilled off, and the residue, in a mixture of toluene and acetone (9: 1), is subjected to fractionated filtration over silica gel 60 from Merck and isolated. The pure product is then [DRIED IN VACUO] at [60XB0;C.] Yield : 4.4 g (73 % of theory).
  • 13
  • 2C6H5O2(1-)*C16H22N2O2S4(2+) [ No CAS ]
  • [ 13361-34-7 ]
  • [ 1118625-27-6 ]
YieldReaction ConditionsOperation in experiment
96% In 1-methyl-pyrrolidin-2-one; at 70℃; for 3h;Inert atmosphere; 30 ml of N-methylpyrrolidone was added to 8.0 g (0.02 moles) of Exemplified compound M-2 and 5.7 g (0.029 moles) of 2-ethylhexyl cyanoacetate. Then the mixture was stirred at an inner temperature of 70 C. for 3 hours under a nitrogen atmosphere. After cooling down to room temperature, 40 ml of methanol followed by 8 ml of acetic acid were added thereto. The deposited crystals were filtrated and washed with methanol. Thus, 8.0 g of Exemplified compound N-17 was obtained (Yield: 96.0%).1H NMR (DMSO-d6) δ(ppm) 4.25-4.05 (m, 4H), 1.70-1.54 (m, 2H), 1.45-1.20 (m, 16H), 0.97-0.78 (m, 12H)
  • 14
  • 2C6H5O2(1-)*C16H22N2O2S4(2+) [ No CAS ]
  • [ 13361-34-7 ]
  • [ 1118625-27-6 ]
YieldReaction ConditionsOperation in experiment
96.0% In 1-methyl-pyrrolidin-2-one; at 70℃; for 3h;Inert atmosphere; The exemplified compound (86) could also be prepared by the following preparation method. N-methylpyrrolidone (30 ml) was added to a mixture of 8.0 g (0.02 mol) of the synthetic intermediate M-2 and 5.7 g (0.029 mol) 2-ethylhexyl cyanoacetate, and the solution was allowed to react in the nitrogen atmosphere at inner temperature of 70C for 3 hours. After cooling to room temperature, 40 ml of ethyl acetate and 8 ml of acetic acid were added in this order. The precipitated crystals were filtrated, washed with methanol, to give 8.0 g of the exemplified compound (86) (yield: 96.0%).
  • 15
  • [ 113728-72-6 ]
  • [ 13361-34-7 ]
  • (Z,Z)-5,5'''-bis[α-cyano-α-(2-ethylhexyl)oxycarbonylmetylene]-5,5'-dihydro-Δ2,2':5',2'':5'',2'''-quaterthiophene [ No CAS ]
  • 16
  • [ 155904-20-4 ]
  • [ 13361-34-7 ]
  • [ 1239599-15-5 ]
  • 17
  • C57H33NO3S9 [ No CAS ]
  • [ 13361-34-7 ]
  • C90H84N4O6S9 [ No CAS ]
  • 18
  • [ 611-94-9 ]
  • [ 13361-34-7 ]
  • [ 947753-66-4 ]
  • 19
  • [ 1429739-55-8 ]
  • [ 13361-34-7 ]
  • [ 1429739-59-2 ]
  • 20
  • [ 1017260-46-6 ]
  • [ 13361-34-7 ]
  • [ 1429739-58-1 ]
  • 21
  • [ 291279-14-6 ]
  • [ 13361-34-7 ]
  • [ 1429739-56-9 ]
  • 22
  • [ 762269-61-4 ]
  • [ 13361-34-7 ]
  • [ 1429739-57-0 ]
  • 23
  • C92H103N5O3S6 [ No CAS ]
  • [ 13361-34-7 ]
  • C114H137N7O5S6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56.6% With piperidine; In chloroform; acetonitrile; at 80℃; for 12h;Inert atmosphere; Compound 2 (0.10 g, 0.066 mmol), 2-ethylhexyl cyanoacetate(0.52 g, 2.63 mmol), and piperidine (1.0 mL) were dissolved inCHCl3 (20 mL) and CH3CN (40 mL), and the solutionwas refluxed at80 C for 12 h under nitrogen atmosphere. Then the solution waspoured into a diluted aqueous HCl (10 mL) solution and extractedwith dichloromethane. The organic phase was dried over anhydrousMgSO4, and the solvent was removed by rotary evaporation.The crude product was purified by silica gel column chromatographyusing petroleum ether/dichloromethane (1:1, v:v) as eluentto give 0.07 g TPA-DTBT-CAO as a purple-red solid (Yield: 56.6%).FT-IR (KBr, cm1): 2214 (nC^N), 1720 (nC]OOR), 949(nC]C). 1H NMR(400 MHz, CDCl3, d/ppm): 8.46 (s, 2H), 8.20 (s, 2H), 8.07 (s, 2H),8.02e8.01 (d, J 7.8 Hz, 2H); 7.87e7.85 (d, J 7.7 Hz, 2H); 7.68 (s,2H); 7.52e7.50 (d, J 8.4 Hz, 2H); 7.41e7.39 (m, 2H); 7.15e7.05 (m,12H); 4.25e4.24 (m, 4H); 3.85e3.83 (d, J 4.9 Hz, 2H); 2.91e2.87(t, J 7.5 Hz, 4H); 2.81e2.77 (t, J 7.5 Hz, 4H); 2.34e2.30 (m, 6H);1.97e1.94 (m, 1H); 1.73e1.72 (m, 10H); 1.45e1.35 (m, 32H); 1.14e1.10 (t, J 7.4 Hz, 6H); 0.98e0.89 (m, 30H). 13C NMR (CDCl3,100 MHz, d/ppm): 163.56, 155.65, 154.28, 152.47, 152.39, 147.78,147.57, 145.30, 143.62, 142.63, 139.83, 136.82, 136,16, 133.85, 132.72,131.61, 131.35, 130.85, 130.75, 129.97, 129.89, 129.86, 128.86, 127.86,127.67, 127.60, 124.80, 124.63, 124.57, 123.75, 123.49, 123.42, 123.00,122.70, 120.52, 116.20, 110.02, 96.93, 78.46, 69.51, 68.78, 68.52,65.53, 49.05, 41.14, 38.97, 38.77, 35.20, 31.77, 31.59, 31.46, 31.34,30.95, 30.86, 30.63, 30.50, 30.32, 30.30, 29.68, 29.27, 29.23, 29.14,29.06, 28.88, 28.67, 24.10, 23.94, 23.71, 23.34, 22.98, 22.92, 22.66,22.59, 22.55, 20.82, 20.77, 19.20, 14.32, 14.10, 14.01, 13.68, 11.88,11.45, 11.07, 10.89. Calcd for C90H103N5O2S6: C, 72.92; H, 7.35; N,5.22; S, 10.25. Found: C, 72.84; H, 7.48; N, 5.62; S, 10.79. MALDI-TOFMS (C114H137N7O5S6) m/z: calcd for 1877.742; found 1877.004.
  • 24
  • [ 127653-16-1 ]
  • [ 13361-34-7 ]
  • (2E,2'E)-bis(2-ethylhexyl) 3,3'-([1,2]dithiolo[4,3-c][1,2]dithiole-3,6-diylbis(4,1-phenylene))bis(2-cyanoacrylate) [ No CAS ]
  • 25
  • [ 127653-16-1 ]
  • [ 13361-34-7 ]
  • [ 1616462-08-8 ]
  • 26
  • C92H118O2S10 [ No CAS ]
  • [ 13361-34-7 ]
  • C114H152N2O4S10 [ No CAS ]
  • 27
  • C80H86O2S12 [ No CAS ]
  • [ 13361-34-7 ]
  • C118H152N2O4S12 [ No CAS ]
  • 28
  • [ 107-19-7 ]
  • [ 109-89-7 ]
  • [ 13361-34-7 ]
  • 2-ethylhexyl (2E,4E)-2-cyano-5-(diethylamino)-penta-2,4-dienoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% Example 5 Preparation of 2-ethylhexyl (2E,4E)-2-cyano-5-(diethylamino)-penta-2,4-dienoate Diethylamine (30 g, 0.41 mol) and propargyl alcohol (18.4 g, 0.328 mol) are dissolved in 250 ml of toluene. 72.6 g of manganese dioxide (activated, <5 μm; 2.5 equiv.) are added portionwise while controlling the strong exotherm (temperature <50 C.) and the mixture is left stirring at 90 C. for 5 hours. The reaction mixture is filtered. The yellow filtrate is poured into a reactor surmounted by a Dean and Stark apparatus. 2-Ethylhexyl cyanoacetate (61.5 g, 0.312 mol) and catalyst (0.1 equiv., 1.77 ml of acetic acid and 3.2 ml of N,N-diethylamine) are added with stirring and the reaction mixture is brought to reflux. It is left at reflux for 5 hours 30 minutes. After cooling, 500 ml of dichloromethane are added and washing is carried out once with a saturated sodium bicarbonate solution and then twice with water. The organic phase is dried and then purified on a silica bed. The first fractions are recovered and concentrated under vacuum. 21.9 g (yield: 23%) of the pure fractions of the derivative of Example 5 are thus obtained in the form of an orange-coloured gum which crystallizes; recrystallization from heptane gave the derivative of Example 5 in the form of a yellow powder: M.P.: 32-37 C. UV (Ethanol): λmax=381 nm, E1%=2240.
  • 29
  • [ 628-51-3 ]
  • [ 13361-34-7 ]
  • 2-ethylhexyl α-cyanoacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With piperazine; dodecylbenzene-sulphonic acid; at 120 - 130℃; for 2h; General procedure: 1.40 moles of butyl cyanoacetate and 2.1 moles of methylene diacetate, obtained through the preparative example 1, were added to a 1 L reactor. Subsequently, the mixture was heated to a temperature comprised between 120 and 130 C. Then 5 mol% of piperazine and 15 mol% of p-toluenesulfonic acid monohydrate were added. The reaction was monitored by gas chromatography or nuclear magnetic resonance every 30 min. After 1 hour, the reaction was terminated, and the n-butyl cyanoacrylate was obtained with a selectivity of 94%, where the selectivity is understood as the amount of monomer produced with respect to the cyanoacetate that has reacted. Subsequently, acetic acid was removed under vacuum and stabilizers were added to the residue for the distillation of the monomer.
  • 30
  • [ 14510-07-7 ]
  • [ 13361-34-7 ]
  • C21H24N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.1% With cadmium(II) iodide; at 75℃; for 1h; 4-carbaldehyde-8-hydroxyquinoline (1.16 g, 6.70 mmol), 2-ethylhexyl cyanoacetate (1.5 ml, 6.70 mmol) and cadmium iodide (0.25 g, 0.67 mmol) were put into a 25 ml round flaskand thoroughly mixed and heated at 75 C for 1 hour. After cooled to room temperature, the mixture was washed with 1% aqueous alcohol and extracted with CH2Cl2, dried with anhydrous MgSO4 and then the solvent was removed on a rotary evaporator. The crude product was purification using column chromatography (silica gel) with the mixture of dichloromethane (CH2Cl2) and n-hexane (2:3, v/v) as the eluent to give a yellow solid (1.96 g, yield 83.1%). δH (400 MHz; (CD3)2SO; Me4Si): 10.19 (s, 1H), 9.03 (d, 1H, J=4 Hz), 9.00 (s, 1H), 7.94 (d, 1H, J=4 Hz), 7.58 (t, 1H, J=8 Hz), 7.44 (d, 1H, J=8 Hz), 7.22 (d, 1H, J=8 Hz), 4.26 (m, 2H), 1.71 (m, 1H), 1.27-1.45 (m, 8H), 0.87-0.94 (m, 6H). δC (600 MHz; (CD3)2CO; Me4Si): 161.8, 154.5, 151.6, 148.7, 139.6, 138.4, 130.2, 126.8, 122.0, 114.8, 114.4, 112.1, 112.0, 69.7, 39.7, 31.1, 29.7, 24.5, 23.6, 14.3, 11.4. MS (MALDI-TOF): Calcd for C21H24N2O3 (M+1): 352.43, Found: 352.39.
  • 31
  • C96H118O2S12 [ No CAS ]
  • [ 13361-34-7 ]
  • C118H152N2O4S12 [ No CAS ]
  • 32
  • [ 110046-60-1 ]
  • [ 13361-34-7 ]
  • C20H22BrNO2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With triethylamine; In chloroform; at 20℃; for 12h; Take compound 20 (1.66g, 6.1mmol) and isooctyl cyanoacetate (5.99g, 30.5mmol) in anhydrous chloroform (50mL), was added a small amount of triethylamine (0.1mL), and then for 12 hours at room temperature, the reaction after washing with water, dried, filtered and the solvent was removed by rotary evaporation with petroleum ether to silica gel column chromatography eluent, to give an orange-yellow solid 21 (2.32g, 84%).
  • 33
  • 5',5'"-(2,1,3-benzothiadiazole-4,7-diyl)bis-[(2,2'bithiophene)-5-carboxaldehyde] [ No CAS ]
  • [ 13361-34-7 ]
  • C46H46N4O4S5 [ No CAS ]
  • 34
  • [ 882303-63-1 ]
  • [ 13361-34-7 ]
  • C38H42N4O4S3 [ No CAS ]
  • 35
  • 5-(7-(5-bromothiophen-2-yl)-5,6-difluoro-2-(2-hexyldecyl)-2H-benzo[d][1,2,3]triazole-4-yl)thiophene-2-carbaldehyde [ No CAS ]
  • [ 13361-34-7 ]
  • 2-ethylhexyl (E)-3-(5-(7-(5-bromothiophen-2-yl)-5,6-difluoro-2-(2-hexyldecyl)-2H-benzo[d][1,2,3]triazol-4-yl)thiophen-2-yl)-2-cyanoacrylate [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 13361-34-7 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 15666-97-4

A168263 [15666-97-4]

Octyl 2-cyanoacetate

Similarity: 0.90

Chemical Structure| 17686-43-0

A501914 [17686-43-0]

Decyl 2-cyanoacetate

Similarity: 0.90

Chemical Structure| 19823-28-0

A146748 [19823-28-0]

Ethyl 2-cyano-3-methylhexanoate

Similarity: 0.89

Chemical Structure| 7352-02-5

A721456 [7352-02-5]

Ethyl 2-cyano-4-methylpentanoate

Similarity: 0.89

Chemical Structure| 7391-39-1

A742301 [7391-39-1]

Ethyl 2-cyanohexanoate

Similarity: 0.89

Esters

Chemical Structure| 15666-97-4

A168263 [15666-97-4]

Octyl 2-cyanoacetate

Similarity: 0.90

Chemical Structure| 17686-43-0

A501914 [17686-43-0]

Decyl 2-cyanoacetate

Similarity: 0.90

Chemical Structure| 7501-71-5

A607978 [7501-71-5]

Ethyl 2-cyano-2-cycloheptylacetate

Similarity: 0.89

Chemical Structure| 7352-02-5

A721456 [7352-02-5]

Ethyl 2-cyano-4-methylpentanoate

Similarity: 0.89

Chemical Structure| 7391-39-1

A742301 [7391-39-1]

Ethyl 2-cyanohexanoate

Similarity: 0.89

Nitriles

Chemical Structure| 15666-97-4

A168263 [15666-97-4]

Octyl 2-cyanoacetate

Similarity: 0.90

Chemical Structure| 17686-43-0

A501914 [17686-43-0]

Decyl 2-cyanoacetate

Similarity: 0.90

Chemical Structure| 7501-71-5

A607978 [7501-71-5]

Ethyl 2-cyano-2-cycloheptylacetate

Similarity: 0.89

Chemical Structure| 7352-02-5

A721456 [7352-02-5]

Ethyl 2-cyano-4-methylpentanoate

Similarity: 0.89

Chemical Structure| 7391-39-1

A742301 [7391-39-1]

Ethyl 2-cyanohexanoate

Similarity: 0.89