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[ CAS No. 1552-96-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1552-96-1
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Chemical Structure| 1552-96-1
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Product Details of [ 1552-96-1 ]

CAS No. :1552-96-1 MDL No. :MFCD00004397
Formula : C11H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CQNPVMCASGWEHM-VMPITWQZSA-N
M.W : 191.23 Pubchem ID :1540638
Synonyms :

Calculated chemistry of [ 1552-96-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.18
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.32
TPSA : 40.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 1.33
Consensus Log Po/w : 1.7

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.821 mg/ml ; 0.0043 mol/l
Class : Soluble
Log S (Ali) : -2.42
Solubility : 0.734 mg/ml ; 0.00384 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.97
Solubility : 2.03 mg/ml ; 0.0106 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 1552-96-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1552-96-1 ]

* 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 [ 1552-96-1 ]

[ 1552-96-1 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 110-89-4 ]
  • [ 141-82-2 ]
  • [ 100-10-7 ]
  • [ 1552-96-1 ]
  • 2
  • [ 91-22-5 ]
  • [ 141-82-2 ]
  • [ 100-10-7 ]
  • [ 1552-96-1 ]
  • 3
  • [ 141-82-2 ]
  • [ 2929-79-5 ]
  • [ 1552-96-1 ]
  • 5
  • [ 1552-96-1 ]
  • 5-methyl-1,3-benzodithiol-2-ylium perchlorate [ No CAS ]
  • 2-(4-dimethylamino-styryl)-5-methyl-benzo[1,3]dithiolylium; perchlorate [ No CAS ]
  • 7
  • [ 1552-96-1 ]
  • [ 73718-09-9 ]
  • 8
  • [ 1552-97-2 ]
  • [ 1552-96-1 ]
  • 9
  • [ 141-82-2 ]
  • [ 100-10-7 ]
  • [ 1552-96-1 ]
YieldReaction ConditionsOperation in experiment
70% With lithium perchlorate; In pyridine; for 5h;Reflux; General procedure: To a stirred solution of benzaldehyde (1a, 1.7 ml, 16.04mmol, 1 equiv) and malonic acid (2, 2 g, 24.06 mmol, 1.5equiv) in pyridine (5 mL) was added LiClO4 (0.34 g, 3.2mmol, 0.2 equiv) and refluxed for 5 hrs. The progress ofreaction was monitored by TLC using eluent EtOAc: nhexane(4:6). After completion of reaction, the solution wasacidified with concentrated HCl to afford a white precipitate.The precipitate was filtered and washed with water (10 ml)twice, further dried to afford 2.2 g (93%) of 3a as the finalproduct. All synthesized compounds were characterized byIR, NMR and mass with satisfactory spectral data.
40% With piperidine; pyridine; at 120℃; for 4h; General procedure: To a solution of the substituted benzaldehyde (1 eq.) and malonate(1.2 eq.) in pyridine (2.5 mL/mmol) at 120 C piperidine (0.04 eq.) wasadded, and the reaction mixture was heated under reflux for 4 h [31].The solvents were removed in vacuo as an azeotrope with toluene(3×70 mL). Water (100 mL) was added, and the aqueous phase wasextracted with ethyl acetate (3×100 mL), brine (1×100 mL), dried(MgSO4) and concentrated. Compounds 1a and 1c-1m were preparedfollowing procedure A.
With piperidine; pyridine; at 80 - 90℃; for 24h; General procedure: A mixture of aromatic aldehydes (3.2 mmol), malonic acid (3.87 mmol), piperidine (0.387 mmol) was dissolved in pyridine and stirred on 80-90 C for 24 h. The pyridine was removed at the vacuum. The reaction mixture was poured into water and washed with HCl. And the precipitate was filtered and washed with hexane for three times, and dried under vacuum to afford the cinnamic acids (Scheme 1).
  • 11
  • [ 17570-30-8 ]
  • [ 74-88-4 ]
  • [ 1552-96-1 ]
  • 12
  • [ 14218-11-2 ]
  • [ 1552-96-1 ]
  • [ 112289-77-7 ]
  • [ 14125-75-8 ]
  • [ 2592-58-7 ]
  • 13
  • [ 41864-22-6 ]
  • [ 1552-96-1 ]
  • [ 150020-94-3 ]
  • 14
  • [ 6066-82-6 ]
  • [ 1552-96-1 ]
  • 4-(Dimethylamino)cinnamic acid N-hydroxysuccinimide ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; N,N-dimethyl-formamide; a. 4-(Dimethylamino)cinnamic acid N-hydroxysuccinimide ester A solution of 4-(dimethylamino)cinnamic acid (0.50 g: commercially available from Aldrich Chemical Company), N-hydroxy-succinimide (0.37 g) and EDCl (0.56 g) in methylene chloride (20 mL) and DMF (5 mL) was stirred at ambient temperature for 18 hours. The product was isolated as described in Example 3a to yield 0.15 g of the title compound as a yellow solid. MS(Cl/NH3) m/e 289 (M+H)+. 1 H NMR(CDCl3, 300 MHz) delta2.86 (br s,4H), 3.05 (s,6H), 6.32 (d,J=16 Hz,1H), 6.67 (dt,J=9 Hz,2H), 7.46 (dt,2H), 7.83 (d,1H).
  • 15
  • [ 5440-00-6 ]
  • [ 1552-96-1 ]
  • [ 1025972-39-7 ]
  • 17
  • [ 1552-96-1 ]
  • [ 156-05-8 ]
  • O-(trans-p-(dimethylamino)cinnamoyl)-L-β-phenyllactate [ No CAS ]
  • 18
  • [ 1552-96-1 ]
  • [ 86052-17-7 ]
  • (E)-3-(4-Dimethylamino-phenyl)-N-[4-(1-ethoxy-ethoxy)-3-methoxy-benzyl]-acrylamide [ No CAS ]
  • 19
  • [ 1552-96-1 ]
  • 3-Bromo-3-(4-dimethylamino-phenyl)-propionic acid [ No CAS ]
  • 20
  • [ 1552-96-1 ]
  • [ 530-62-1 ]
  • p-Dimethylaminocinnamic acid imidazole ester [ No CAS ]
  • 21
  • [ 1552-96-1 ]
  • [ 594-19-4 ]
  • 3-(4-dimethylamino-phenyl)-4,4-dimethyl-pentanoic acid [ No CAS ]
  • 2-(4-dimethylaminophenylmethyl)-3,3-dimethylethylbutanoic acid [ No CAS ]
  • 22
  • [ 1552-96-1 ]
  • 2-(1-amino-ethyl)-5-methyl-thieno[2,3-<i>d</i>][1,3]oxazin-4-one; compound with trifluoro-acetic acid [ No CAS ]
  • 3-(4-dimethylamino-phenyl)-<i>N</i>-[1-(5-methyl-4-oxo-4<i>H</i>-thieno[2,3-<i>d</i>][1,3]oxazin-2-yl)-ethyl]-acrylamide [ No CAS ]
  • 23
  • [ 1552-96-1 ]
  • [ 199678-00-7 ]
  • (E)-2-(4-(3-(4-Dimethylaminophenyl)propenoyl)aminobutyl)-7-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
  • 26
  • [ 1552-96-1 ]
  • [ 1024109-26-9 ]
  • 3-(4-dimethylamino-phenyl)-<i>N</i>-{5-[4-(1<i>H</i>-indol-3-yl)-piperidin-1-yl]-pentyl}-acrylamide [ No CAS ]
  • 27
  • [ 1552-96-1 ]
  • [ 2878-86-6 ]
  • 3-(4-dimethylamino-phenyl)-acrylic acid 2-{2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1<i>H</i>-indol-3-yl]-acetylamino}-ethyl ester [ No CAS ]
  • 28
  • [ 65946-59-0 ]
  • [ 100-10-7 ]
  • [ 1552-96-1 ]
  • 29
  • [ 47705-70-4 ]
  • [ 1552-96-1 ]
  • 10-(4-dimethylaminophenyl)-7-hydroxy-2-(3,4-dihydroxyphenyl)-pyrano[4,3,2-de]chromen-1-ylium-3-O-β-D-glucoside [ No CAS ]
  • 30
  • [ 18470-06-9 ]
  • [ 1552-96-1 ]
  • 10-(4-dimethylaminophenyl)-7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-pyrano[4,3,2-de]chromen-1-ylium-3-O-β-D-glucoside [ No CAS ]
  • 31
  • [ 1552-96-1 ]
  • [ 71-43-2 ]
  • [ 22965-98-6 ]
  • 33
  • {4-[(E)-isopropyliminomethyl]phenyl}dimethylamine [ No CAS ]
  • [ 141-82-2 ]
  • (Z)-3-(4-dimethylaminophenyl)acrylic acid [ No CAS ]
  • [ 1552-96-1 ]
  • 34
  • [ 141-82-2 ]
  • [ 97221-11-9 ]
  • (Z)-3-(4-dimethylaminophenyl)acrylic acid [ No CAS ]
  • [ 1552-96-1 ]
  • 35
  • (E)-(S)-4-((S)-2-Amino-3-phenyl-propionylamino)-5-phenyl-pent-2-enoic acid ethyl ester; hydrochloride [ No CAS ]
  • [ 1552-96-1 ]
  • (E)-(S)-4-{(S)-2-[(E)-3-(4-Dimethylamino-phenyl)-acryloylamino]-3-phenyl-propionylamino}-5-phenyl-pent-2-enoic acid ethyl ester [ No CAS ]
  • 37
  • [ 1552-96-1 ]
  • (6R,7R)-7-(4'-N,N-dimethylaminocinnamoyl)amino-3-acetoxymethyl-3-cephem-4-carboxylic acid [ No CAS ]
  • 38
  • [ 1552-96-1 ]
  • methyl 4,4-dimethyl-3-(4-dimethylaminophenyl)pentanoate [ No CAS ]
  • 39
  • [ 1552-96-1 ]
  • (S)-3-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-6-[(E)-3-(4-dimethylamino-phenyl)-acryloylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid [ No CAS ]
  • 40
  • [ 1552-96-1 ]
  • N-(4-hydroxy-3-methoxybenzyl)-(E)-3-<4-(dimethylamino)phenyl>propenamide [ No CAS ]
  • 41
  • [ 1552-96-1 ]
  • [ 147700-14-9 ]
  • 42
  • [ 1552-96-1 ]
  • 8-[(E)-2-(4-Dimethylamino-phenyl)-vinyl]-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione [ No CAS ]
  • 43
  • [ 1552-96-1 ]
  • 1(R),2(R)-trans-cyclohexanediol bis<3-<4-(dimethylamino)phenyl>-2-propenoate> [ No CAS ]
  • 44
  • [ 1552-96-1 ]
  • (E)-3-(4-Dimethylamino-phenyl)-acrylic acid (2R,3R,5S,8R,9R,10R)-2-acetoxy-10-[(E)-3-(4-dimethylamino-phenyl)-acryloyloxy]-8,12,15,15-tetramethyl-4-methylene-13-oxo-5-[(E)-(3-phenyl-acryloyl)oxy]-tricyclo[9.3.1.03,8]pentadec-11-en-9-yl ester [ No CAS ]
  • 45
  • [ 1552-96-1 ]
  • (E)-3-(4-Dimethylamino-phenyl)-acrylic acid (3S,4S,5R,6S)-4,5-bis-[(E)-3-(4-dimethylamino-phenyl)-acryloyloxy]-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl ester [ No CAS ]
  • 47
  • [ 1552-96-1 ]
  • (E)-3-(4-(Dimethylamino)phenyl)-1-((S)-2-((pyrrolidin-1-yl)methyl)pyrrolidin-1-yl)propenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 19 (General Procedure (A)) (E)-3-(4-(Dimethylamino)phenyl)-1-((S)-2-((pyrrolidin-1-yl)methyl)pyrrolidin-1-yl)propenone 74 mg of the title compound were synthesised as described for (E)-3-(4-bromophenyl)-1-((S)-2-((pyrrolidin-1-yl)methyl)pyrrolidin-1-yl)propenone, using <strong>[1552-96-1](E)-4-(dimethylamino)cinnamic acid</strong> instead of (E)-4-bromocinnamic acid. 1H-NMR (CDCl3, 2 sets of signals) delta 1.50-2.15 (m, 8 H); 2.45-2.80 (m, 6 H); 3.00 (s, 6 H); 3.60 and 3.65 (both m, together 2 H); 4.15 and 4.45 (both m, together 1 H); 6.50 and 6.65 (both d, together 1 H); 6.67 (m, 2 H); 7.40 (d, 2 H); 7.65 (d, 1 H). HPLC method A: elution at 7.23 min. MS: calc. for [M+H]+: 328; found: 328.
  • 48
  • 2-(4-aminophenylethenyl)benzothiazole [ No CAS ]
  • [ 1552-96-1 ]
  • [ 137-07-5 ]
  • 2-(4-Dimethylaminophenylethenyl)benzothiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
560 mg (48.7%) With (1S,2R)-(+)-norphedrine; potassium carbonate; (e) 2-(4-Dimethylaminophenylethenyl)benzothiazole (16) A mixture of 2-aminothiophenol 9 (0.51 g, 4.1 mmol) trans-4-dimethylaminocinnamic acid 14 (0.79 g,, 4.1 mmol) and PPA (10 g) was heated to 220 C. for 4 hrs. The reaction mixture was cooled to room temperature and poured into 10% of potassium carbonate solution (~400 mL). The residue was collected by filtration under reduced pressure. Purification with flush column (hexanes: ethyl acetate=2:1) gave 560 mg (48.7%) of product 15 as a yellow solid.
  • 49
  • [ 5440-00-6 ]
  • [ 1552-96-1 ]
  • [ 2592-95-2 ]
  • [ 147700-14-9 ]
YieldReaction ConditionsOperation in experiment
With EDAC; In N,N-dimethyl-formamide; 1,3-Dimethyl-8-(4-dimethylaminostyryl)xanthine (30a) A solution of 4-dimethylaminocinnamic acid (0.1 g, 0.52 mmol), 1-hydroxy benzotriazole (0.14 g, 1.04 mmol) and EDAC (0.19 g, 1.04 mmol) in DMF (1 ml) was sonicated for 1 h. 1,3-Dimethyl-5,6-diaminouracil (0.088 g, 0.52 mmol) was added and the mixture was heated for 3 h at 80 C. The dark red solution was cooled to room temperature and the product was obtained as a deep yellow precipitate (0.045 g).
  • 50
  • [ 1552-96-1 ]
  • [ 75567-86-1 ]
YieldReaction ConditionsOperation in experiment
(1) 0.37 g (1.79 mmol) of methyl 3-(4-dimethylaminophenyl)propionate was obtained as a colorless oily substance using 0.57 g (3.0 mmol) of <strong>[1552-96-1]p-dimethylaminocinnamic acid</strong> as a starting material the same manner as in Production Example 10 (1). Its spectroscopic data are as follows: 1 H-NMR (CDCl3) delta (ppm) 2.58 (2H, t, J=7.8 Hz), 2.86 (2H, t, J=7.8 Hz), 2.91 (6H, s), 3.67 (3H, s), 6.69 (2H, d, J=8.8 Hz), 7.07 (2H, d, J=8.8 Hz).
  • 51
  • [ 1552-96-1 ]
  • 2-(4-Dimethylaminostyryl)-5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]azepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
16.3% EXAMPLE 96 2-(4-Dimethylaminostyryl)-5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]azepine The title compound was obtained by reacting 4-dimethylaminocinnamic acid, 3-amino-epsilon-caprolactam and phosphorus pentasulfide in the method described in Example 18. Yield 16.3% m.p. 207-210 (recrystallized from ethyl acetate). IR(KBr)cm: 3274, 1604, 1548, 1525, 1443, 1365, 1165. NMR(CDCl3)delta: 1.67(2H,m). 1.81(2H,m), 2.88(2H,t), 3.09(2H,t), 2.98(6H,s), 6.68(2H,d, J=8.91 Hz), 6.93(2H,d), 7.36(2H,d). Elemental analysis for C17 H21 N3 S.0.4H2 O. Calculated: C, 66.59; H, 7.17; N, 13.70; S, 10.46. Found: C, 66.77; H, 6.93; N, 13.62; S, 10.85.
  • 52
  • [ 1552-96-1 ]
  • [ 5970-45-6 ]
  • [ 5144-89-8 ]
  • [Zn(1,10-phenanthroline)((4-dimethylamino)cinnamic acid(-1H))2] [ No CAS ]
  • 53
  • [ 4112-65-6 ]
  • [ 1552-96-1 ]
  • [ 1242154-14-8 ]
  • 54
  • [ 63511-96-6 ]
  • [ 1552-96-1 ]
  • 55
  • [ 1552-96-1 ]
  • [ 3366-95-8 ]
  • [ 1326302-68-4 ]
YieldReaction ConditionsOperation in experiment
57.1% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h; General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).
  • 56
  • [ 98-10-2 ]
  • [ 1552-96-1 ]
  • [ 1332498-90-4 ]
YieldReaction ConditionsOperation in experiment
75% General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 × 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).
  • 57
  • [ 98-64-6 ]
  • [ 1552-96-1 ]
  • [ 1332498-93-7 ]
YieldReaction ConditionsOperation in experiment
81% General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 × 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).
  • 58
  • [ 701-34-8 ]
  • [ 1552-96-1 ]
  • [ 1332498-94-8 ]
YieldReaction ConditionsOperation in experiment
84% General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 × 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).
  • 59
  • [ 1552-96-1 ]
  • [ 402-46-0 ]
  • [ 1332498-92-6 ]
YieldReaction ConditionsOperation in experiment
77% General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 × 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).
  • 60
  • [ 1552-96-1 ]
  • [ 70-55-3 ]
  • [ 1332498-91-5 ]
YieldReaction ConditionsOperation in experiment
85% General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 × 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).
  • 61
  • [ 1552-96-1 ]
  • [ 1187423-42-2 ]
  • 62
  • [ 1552-96-1 ]
  • [ 79-22-1 ]
  • C13H15NO4 [ No CAS ]
  • 63
  • [ 887144-94-7 ]
  • [ 1552-96-1 ]
  • [ 1380394-84-2 ]
  • [ 1380394-77-3 ]
  • 64
  • [ 1552-96-1 ]
  • [ 4244-84-2 ]
  • [ 1400452-56-3 ]
YieldReaction ConditionsOperation in experiment
81% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h; General procedure: trans-Cinnamic acid (1.49, 10.0 mmol) and HOBt (2.263 g, 15 mmol) were dissolved in DMF (50 mL). EDC.HCl (2.865 g, 15 mmol) was added, followed by beta-alanine ethyl ester hydrochloride (1.53 g, 10 mmol) and DIPEA (5.3 mL, 30 mmol) and the solution was stirred at RT for 16 h. The solvent was removed in vacuo and the residual oil was re-dissolved in EtOAc (100 mL), the organic phase was washed with 5% w/v aqueous sodium hydrogen carbonate solution (2 ×100 mL) then 5% w/v citric acid solution (2× 30 mL) and brine, before being dried on MgSO4. The solvent was evaporated in vacuo to afford the product (1.48 g, 59.8% yield).
  • 65
  • [ 1779-81-3 ]
  • [ 1552-96-1 ]
  • [ 1427204-77-0 ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; Inert atmosphere; II. Experimental Procedure General procedure: (E)-3-(4-ethylphenyl)acrylic acid (100 mg, 0.567 mmol), 3-((ethylimino)methyleneamino)-N,N-dimethylpropan-1-aminium chloride (163 mg, 0. 851 mmol), and N,N-dimethylpyridin-4-amine (13 mg, 0.19 mmol) were dissolved in dichloromethane (10 mL). N-ethyl-N-isopropylpropan-2-amine (161 mg, 1.248 mmol) was added followed by 4,5-dihydrothiazol-2-amine (64 mg, 0.624 mmol). The reaction mixture was stirred for 12 hours at room temperature. The reaction was concentrated under vacuum. Purification by column chromatography provided (E)-N-(4,5-dihydrothiazol-2-yl)-3-(4-ethylphenyl)acrylamide as a white powder (58 mg, 40% yield).
  • 66
  • [ 115545-85-2 ]
  • [ 1552-96-1 ]
  • [ 1176235-11-2 ]
YieldReaction ConditionsOperation in experiment
89% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere; General procedure: To a solution of 4-(dimethylamino)cinnamic acid (10b) (92.1mg, 0.48mmol) in DMF (5mL) were added d-Cys(S-Trt)-OMe (101mg, 0.53mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (311mg, 1.62mmol), and 4-(dimethylamino)pyridine (DMAP) (151mg, 1.23mmol) under Ar. After the reaction mixture was stirred at room temperature for 24h, water (100mL) was added. The products were extracted with EtOAc (3×100mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue obtained was purified by silica gel column chromatography (Hex/EtOAc=1:1) to give an N-acyl-S-trityl d-cysteine methyl ester derivative, (S)-methyl 2-((E)-3-(4-(dimethylamino)phenyl)acrylamido)-3-(tritylthio)propanoate (259mg, 89%) as a yellow oil (step g in Scheme 1). 1H NMR (500MHz, CDCl3) delta 2.72 (m, 2H, ABX system), 3.01 (s, 6H), 3.72 (s, 3H), 4.78 (m, 1H, ABX system), 6.15 (d, J=15.5Hz, 1H), 6.20 (d, J=5.9Hz, 1H, NH), 6.68 (d, J=8.6Hz, 2H, AA?BB? system), 7.20-7.42 (complex, 17H), 7.52 (d, J=15.5Hz, 1H); ESI-MS m/z: 573 [(M+Na) +]. To a solution of the amide obtained above (118mg, 0.21mmol) in dry CH2Cl2 (10mL) were added triphenylphosphine oxide (Ph3PO) (124mg, 0.45mmol) and trifluoromethanesulfonic anhydride (Tf2O) (360muL, 2.14mmol) under Ar.37 After the reaction mixture was stirred at room temperature for 40min, the reaction was quenched by adding water (50mL), and the products were extracted with CHCl3 (50mL), and then EtOAc (2×50mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc=1:2) to give thiazoline ester 11b (44.2mg, 71%) as a yellow solid (step h in Scheme 1). 1H NMR (500MHz, CDCl3) delta 2.96 (s, 6H), 3.53 (m, 2H, ABX system), 3.79 (s, 3H), 5.14 (dd, J=8.6, 8.6Hz, 1H, ABX system), 6.63 (d, J=7.5Hz, 2H, AA?BB? system), 6.88 (d, J=15.5Hz, 1H), 7.04 (d, J=15.5Hz, 1H), 7.34 (d, J=7.5Hz, 2H, AA?BB? system); FT-IR numax (cm-1): 1724; ESI-MS m/z: 291 [(M+H)+]. To a mixture of thiazoline ester 11b (21.1mg, 0.07mmol) in EtOH (2mL) and 10mM NH4HCO3 (6mL) was added porcine liver esterase (9.2mg), and the reaction mixture was stirred at 37C under Ar for 19h. After evaporation of the reaction mixture, the residue obtained was suspended in a mixture of MeOH/CHCl3. The precipitate was filtered off, and the filtrate and washings of the residue were combined and concentrated to give anaolg 2b (14.1mg, 71%) as an orange solid (step i in Scheme 1). 26% ee from chiral HPLC (retention time of l-isomer: 13.2min, d-isomer: 12.9min); 1H NMR (500MHz, CD3OD) delta 3.00 (s, 6H), 3.62 (m, 2H, ABX system), 5.01 (dd, J=8.6, 8.6Hz, 1H, ABX system), 6.72 (d, J=9.0Hz, 2H, AA?BB? system), 6.86 (d, J=16Hz, 1H) 7.21 (d, J=16Hz, 1H), 7.44 (d, J=9.0Hz, 2H, AA?BB? system); 13C NMR (125MHz, CD3OD, delta): 31.2 (t), 34.5 (q)×2, 79.7 (d), 112.5 (d)×2, 115.9 (d), 122.5 (s), 130.1 (d)×2, 144.1 (d), 152.1 (s), 170.4 (s), 172.2 (s); FT-IR numax (cm-1): 3392, 1602; HR-ESI-MS m/z: [M+H]+ calcd for C14H17N2O2S, 277.1011; found, 277.0989.
  • 67
  • [ 1552-96-1 ]
  • [ 95-54-5 ]
  • [ 2562-90-5 ]
YieldReaction ConditionsOperation in experiment
With polyphoshporic acid; at 220℃; for 4h; t-DMASBI was synthesized by heating the equimolar mixture of 4-N,N-dimethylaminocinnamic acid (Sigma Aldrich Chemicals) and 1,2-diaminobenzene (Sigma Aldrich Chemicals) in polyphoshporic acid at 220 C for 4 h by following the procedure reported in the literature for the synthesis of similar molecules [35]. The compound was first purified by column chromatography followed by thin layer chromatography. The compound was confirmed by 1H NMR spectroscopy and mass spectrometry as follows: 1H NMR (400 MHz, CDCl3, ppm) delta 7.62 (d, J = 7.6 Hz, 1H); 7.50 (d, J = 16.4 Hz, 1H); 7.43 (d, J = 8 Hz, 1H); 7.17 (d, J = 5.2 Hz, 2H); 7.07 (dd, J = 8, 17.2 Hz, 2H); 6.79 (d, J = 16.4 Hz, 1H), 6.45 (d, J = 8, 2H), 5.73 (brs, 1H), 2.85 (s, 6H). From HRMS the molecular mass (M+1) was found to be m/z: 264.035.
  • 68
  • N-2'-hydroxyethyl-5-(α-hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide [ No CAS ]
  • [ 1552-96-1 ]
  • N-[2'-(4''-(dimethylamino)cinnamoyloxy)ethyl]-5-(α-hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 16h;Reflux; N-[2'-(4M-((Dimethylamino)cinnamoyloxy)ethyl]-5-(a-hydroxy-a-2-pyridylbenzyl)-7-(-2- pyridyIbenzylidene)-5-norbornene-2,3-dicarboximide (131) Compound 131 was prepared by a procedure similar to that of Kalgutkar and co-workers (Kalgutkar, A. S. et al. J. Med. Chem. 2000, 43, 2860-2870). To a mixture of 4- (dimethylamino)cinnamic acid (76 mg, 0.40 mmol), dicyclohexylcarbodiimide (88 mg, 0.43 mmol) and 4-dimethylaminopyridine (5 mg) in dry dichloromethane (9 mL) was added 102 (247 mg, 0.4 mmol) in dichloromethane (10 mL), and the mixture heated under reflux for 16 h. The mixture was taken up in water (30 mL), extracted with ethyl acetate (2 x 30 mL), dried over anhydrous magnesium sulfate and the solvent removed in vacuo. Purification by flash chromatography (hexane/ethyl acetate 1 :1) afforded 131 as a yellow solid (58 mg, 0.08 mmol, 18%). mp 121-126 C; 1H NMR (300 MHz, CDC13) £2.97-3.06 (6H, m, NMe2), 3.34-3.38 (0.1H, m, W/H-3), 3.40 (0.4H, dd, J= 8.2 and 3.4 Hz, Y/H-3), 3.47-3.52 (0.5H, m, V/H-2), 3.57-3.72 (2.1H, m, 1H NCH2, 0.5H V/H-3, 0.2H W H-2 and W/H-4, 0.4H Y/H-2), 3.82-3.92 (1.5H, m, 1H NCH2 and 0.5H V/H-l), 3.94-3.96 (0.4H, m, Y/H-4), 4.24^1.38 (2.5H, m, 2H CH20 and 0.5H V/H-4), 4.45^1.48 (0.5H, m, O.IH W/H-1 and 0.4H Y/H-1), 5.53-5.66 (1.9H, m, 0.5H V/H-6, 0.4H Y/H-6 and 1H OH), 6.05-6.06 (O.IH, m, W/H-6), 6.10-6.15 (1H, m,OCOCH ), 6.64-7.60 (21H, m, 1H CHAr and 20Eta Ar), 8.46-8.53 (1.5Eta, m, 1Eta 2V/Pyr, 0.1Eta W/aPyr and 0.4Eta Y/oPyr), 8.62-8.63 (0.5Eta, m, 0.1Eta W/aPyr and 0.4Eta Y/aPyr); vmax/cnf 1 1154 and 1256 (C-0 ester), 1599 (C=0 imide), 1702 (C=0 ester); m/z (FAB+) 729 (MH+, 4%), 120 (100); (Found: MH+ 729.3080, C46H4iN405 requires 729.3077).
  • 69
  • [ 1391625-30-1 ]
  • [ 1552-96-1 ]
  • [ 1391627-41-0 ]
  • 70
  • [ 1188382-13-9 ]
  • [ 1552-96-1 ]
  • (3S,6R,8S)-6-hydroxy-3,6,9-trimethyl-2-oxo-2,3,3α,4,5,6,6α,7,8,9β-decahydroazuleno[4,5-β]furan-8-yl (E)-3-(4-(dimethylamino)phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% General procedure: To a solution of compound 5 (20 mg, 0.075 mmol) and acid (0.075 mmol) in DCM (10 mL) at room temperature was added DMAP (18.3 mg, 0.15 mmol). After stirring for 10 min, EDCI (71.9 mg, 0.34 mmol) was added in one portion. The reaction was allowed to stir overnight. Then, water (15mL) was added. The reaction mixture was extracted with DCM (3·10mL). The organic layer was then washed with brine, dried over Na2SO4, and concentrated in vacuum. Purification by flash column chromatography (PE: EtOAc=4:1) provided the derivatives of interest.
  • 71
  • [ 65786-13-2 ]
  • [ 1552-96-1 ]
YieldReaction ConditionsOperation in experiment
85% With dihydrogen peroxide; potassium carbonate; In acetonitrile; at 20℃; for 5h; General procedure: To a 5 mL round bottom flask equipped with a stirbar, trans-2?-hydroxychalcone 1a (1 mmol), K2CO3(1.38 g, 10 mmol), 35% H2O2 solution (0.5 mL) and2 mL acetonitrile were added. The reaction was stirredat room temperature and monitored by TLC (thin layerchromatograph) until disappearance of the starting material.The solvent was evaporated with reduced pressure. To theresidue, it was added 1 mol L-1 hydrochloric acid, the solidwas filtered to afford 2a as white solid (133 mg, 90%);1H NMR (300 MHz, DMSO-d6) d 7.58 (d, 1H, J 16 Hz),7.42-7.69 (m, 5H), 6.53 (d, 1H, J 16 Hz); 13C NMR(300 MHz, DMSO-d6) d 167.7, 144.0, 134.3, 130.3, 128.9,128.2, 119.3.
  • 72
  • [ 110-91-8 ]
  • [ 1552-96-1 ]
  • (E)-N,N-dimethyl-4-(3-morpholinoprop-1-enyl)aniline [ No CAS ]
  • 73
  • [ 1809-20-7 ]
  • [ 1552-96-1 ]
  • diisopropyl (E)-(4-(dimethylamino)styryl)phosphonate [ No CAS ]
  • 74
  • [ 1552-96-1 ]
  • (E)-N,N-dimethyl-4-(2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)vinyl)aniline [ No CAS ]
  • 75
  • [ 1552-96-1 ]
  • [ 873-55-2 ]
  • [ 67229-91-8 ]
  • 76
  • [ 100-10-7 ]
  • malonic [ No CAS ]
  • [ 1552-96-1 ]
  • 77
  • [ 1552-96-1 ]
  • (E)-3-(4-(dimethylamino)phenyl)-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)acrylamide [ No CAS ]
  • 78
  • [ 1557201-10-1 ]
  • [ 1552-96-1 ]
  • (E)-4-(2-(2,3-dihydro-1H-inden-2-yl)vinyl)-N,N-dimethylaniline [ No CAS ]
  • 79
  • [ 38191-34-3 ]
  • [ 1552-96-1 ]
  • N,N-dimethyl-4-[(1E)-2-(6-bromo-2-benzoxazolyl)ethenyl]benzenamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.6% With polyphosphoric acid; at 180℃; for 1h; 2-Amino-5-bromophenol (935 mg, 5.00 mmol) and 4- (dimethylamino) cinnamic acid (955 mg, 5.00 mmol) were dissolved in polyphosphoric acid (12 g)Followed by stirring at 180 C. for 1 hour.After returning to room temperature,After adding purified water and neutralizing with potassium carbonate,And extracted with ethyl acetate (50 mL × 2).The organic layer was washed with saturated brine,After dehydration with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/1, volume ratio) as an elution solvent,Compound 23 was obtained in a yield of 130 mg (yield 7.60%).
  • 80
  • [ 1552-96-1 ]
  • N,N-dimethyl-4-[(1E)-2-(6-tributylstannyl-2-benzoxazolyl)ethenyl]benzenamine [ No CAS ]
  • 81
  • [ 1552-96-1 ]
  • N,N-dimethyl-4-[(1E)-2-(6-iodo-2-benzoxazolyl)ethenyl]benzenamine [ No CAS ]
  • 82
  • [ 1552-96-1 ]
  • [ 108-93-0 ]
  • (E)-cyclohexyl 3-(4-(dimethylamino)phenyl)acrylate [ No CAS ]
  • 83
  • [ 68820-12-2 ]
  • [ 1552-96-1 ]
  • 2-((4-methylphenyl)sulfonamido)cyclohexyl (E)-3-(4-(dimethylamino)phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 50℃;Green chemistry; General procedure: A mixture of aziridine 1 (0.20 mmol), carboxylic acid 2 (0.24 mmol), and DBU (0.08 mmol, 40 mol%) inTHF (2.0 mL) were added subsequently. The mixture was stirred at 50 C for 24-36 h. After completionof the reaction as indicated by TLC, evaporation of the solvent followed by purification on silica gelprovided the corresponding product 3.2-((4-Methylphenyl)sulfonamido)cyclohexyl cinnamate (3aa) This compound was obtained as a whitesolid; Yield: 74.2 mg (93%); mp 93-94 C; 1H NMR (400 MHz, CDCl3): delta 7.71 (d, J = 8.0 Hz, 2H),7.49-7.39 (m, 6H), 7.12 (d, J = 7.6 Hz, 2H), 5.99 (d, J = 16.0 Hz, 1H), 5.41 (d, J = 7.6 Hz, 1H), 4.71 (td,J = 10.0, 4.0 Hz, 1H), 3.33-3.25 (m, 1H), 2.17-2.15 (m, 4H), 2.00 (d, J = 11.6 Hz, 1H), 1.71-1.69 (m,2H), 1.40-1.26 (m, 4H); 13C NMR (100 MHz, CDCl3): delta 167.1, 144.9, 142.7, 138.4, 134.1, 130.4, 129.5,128.9, 128.0, 126.8, 117.4, 74.1, 57.3, 34.1, 31.2, 24.2, 23.7, 21.1; IR (KBr) (cm-1) v 3430, 3309, 3061,2944, 2863, 1723, 1636, 1598, 1448, 1366, 1329, 1163, 1025; HRMS (ESI): m/z [M+Na]+ calcd forC22H25NO4SNa: 422.1402, found: 422.1423.
  • 84
  • [ 1552-96-1 ]
  • C15H22N6O [ No CAS ]
  • 86
  • [ 1552-96-1 ]
  • [ 1154-78-5 ]
  • 2-(3,4-dihydroxyphenyl)-8-hydroxy-5-(4''-(dimethylamino)phenyl)pyrano[4,3,2-de]chromen-1-ium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% In ethanol; water; at 37℃; for 168h;pH 3.5; General procedure: The synthesis of the pyranoluteolinidin-type pigments 4-7 followed a procedure described elsewhere.35 Briefly, these pigments were obtained by the reaction of individual mixtures of luteolinidin 3a (30.7 mg, 0.10 mmol) with 1,3-acetonedicarboxylic acid (50 equiv), caffeic acid (10 equiv), 4-(dimethylamino)cinnamic acid (10 equiv) or oxaloacetic acid (30 equiv.) in aqueous solution with 20% of ethanol (50 mL) at pH 3.5 (except for pigment 7, which pH was set to 2.6). The reactions were stirred at room temperature during one week. The formation of the respective pyranoluteolinidins 4-7 was monitored every 24 h by HPLC-DAD. When the products reach their maximum intensity, the reaction were stopped, ethanol was evaporated and the samples were pre-purified on a Buchner funnel loaded with C18 silica gel. The final purification was achieved by column chromatography using reversed-phase C18 silica gel or Toyopearl HW-40S as stationary phase (250 * 16 mm i.d.), using mixtures of acidified water (with HCl 2%) with increasing percentages of methanol as eluent. Pyranoluteolinidin-based dyes 4-6 presented identical spectroscopic data to those previously reported in the literature. 10-Carboxy-pyranoluteolinidin (7) was obtained as an orange solid (3.6 mg, 9.6%). 1H NMR (600.13 MHz, DMSO-d6/TFA 90:10), delta (ppm): 7.89 (s, 1H, H-9), 7.72 (dd, J = 2.2 and 8.6 Hz, 1H, H-6'), 7.69 (s, 1H, H-3), 7.65 (d, J = 2.2 Hz, 1H, H-2'), 7.04 (d, J = 8.6 Hz, 1H, H-5'), 7.30 and 7.16 (2d, J = 2.0 Hz, 2H, H-6 and H-8). 13C NMR (125.77 MHz, DMSO-d6/TFA 90:10), delta (ppm): 169.9 (C-10), 169.9 (COOH), 168.1 (C-7), 160.5 (C-2), 154.3 (C-4'), 153.9 (C-5), 153.0 (C-8a), 146.9 (C-3'), 122.9 (C-6'), 120.5 (C-1'), 117.1 (C-5'), 115.0 (C-2'), 109.4 (C-4a), 109.3 (C-3), 103.2 (C-9), 100.8 (C-8 and C-6). LC-DAD/ESI-MS: 7 [M]+ m/z 339, lambdamax 492 nm.
  • 87
  • [ 1552-96-1 ]
  • (E)-3-(4-(dimethylamino)phenyl)acryloyl fluoride [ No CAS ]
  • 88
  • [ 353-83-3 ]
  • [ 1552-96-1 ]
  • [ 1427737-86-7 ]
YieldReaction ConditionsOperation in experiment
42% With copper(II) bis(trifluoromethanesulfonate); triethylamine; silver carbonate; In dimethyl sulfoxide; at 80℃; for 24h;Inert atmosphere; General procedure: Cinnamic acid (0.4 mmol), CF3CH2I (2.0 equiv), Cu(OTf)2 (40 mol%), Ag2CO3 (2.0 equiv), Et3N (2.0 equiv) and DMSO (3.0 mL) were added to a one-neck flask. The flask was sealed, and the reaction mixture was allowed to stir at 80 C for 24 h under Ar atmosphere. Then the reaction solution was cooled down to the room temperature. The mixture was then poured into water and extracted with CH2Cl2 (3×15 mL). The combined organic layers were washed with water and brine, dried over MgSO4, and filtered. The solvent was removed under vacuum. The residue was purified by flash column chromatography to afford 2,2,2-trifluoroethylated alkenes.
  • 89
  • [ 20432-35-3 ]
  • [ 1552-96-1 ]
  • 90
  • [ 1552-96-1 ]
  • 1,3-dioxoisoindolin-2-yl 1-tosylpiperidine-4-carboxylate [ No CAS ]
  • dimethyl(4-{2-[1-(toluene-4-sulfonyl)piperidin-4-yl]vinyl}phenyl)amine [ No CAS ]
  • 91
  • [ 626-62-0 ]
  • [ 1552-96-1 ]
  • (E)-4-(2-cyclohexylvinyl)-N,N-dimethylaniline [ No CAS ]
  • 92
  • [ 121-69-7 ]
  • [ 1552-96-1 ]
  • 93
  • [ 1552-96-1 ]
  • (R)-6-(1-aminoethyl)-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]
  • (R,E)-N-(1-(1-cyclopentyl-4-oxo-4, 5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)ethyl)-3-(4-(dimethylamino)phenyl)acrylamide [ No CAS ]
  • 94
  • [ 1552-96-1 ]
  • [ 1316830-38-2 ]
  • 95
  • [ 1552-96-1 ]
  • C11H14N2S [ No CAS ]
  • 96
  • [ 1552-96-1 ]
  • cyclobutanone O-perfluorobenzoyl oxime [ No CAS ]
  • 6-(4-(dimethylamino)phenyl)hex-5-enenitrile [ No CAS ]
  • 6-(4-(dimethylamino)phenyl)hex-5-enenitrile [ No CAS ]
  • 97
  • [ 1552-96-1 ]
  • [ 3282-30-2 ]
  • C16H21NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 0℃; for 0.5h; General procedure: Step 1: to a solution of cinnamic acid 59 (1.0 eq.) in THF (~0.3 M) was added Et3N (1.3 eq.) and then trimethylacetyl chloride (1.2 eq.) dropwise at 0 C. The mixture was stirred at 0 C for 30 min and then filtered. The filtrate was used for the next step without further purification. Step 2: to a solution of lactam 61 (1.0 eq.) in THF (~0.3 M) was added n-BuLi (1.6 M in THF, 1.2 eq.) dropwise at -78 C. After stirring at -78 C for 45 min, the filtrate from last step (1.0 eq.) was added. The resulting mixture was allowed to stir at -78 C until completion, monitored by TLC. The reaction was then quenched with saturated aqueous NH4Cl solution and extracted with EtOAc (3 ×). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography. Compounds 6,1,2 73, 10,2 12,2 14,1 18,4 20,4 26,5 30,4 31,1 32,1 37,1 and 385 were reported previously.
  • 98
  • [ 1552-96-1 ]
  • (E)-1-(3-(4-dimethylaminophenyl)prop-2-enoyl)-5,6-dihydropyridin-2(1H)-one [ No CAS ]
  • 99
  • [ 1552-96-1 ]
  • C18H24FN3O4 [ No CAS ]
  • C29H35FN4O5 [ No CAS ]
  • 100
  • [ 66235-11-8 ]
  • [ 1552-96-1 ]
  • (E)-2-(2-(4-(3-(4-(dimethylamino)phenyl)acryloyl)piperazin-1-yl)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
  • 101
  • [ 108-85-0 ]
  • [ 1552-96-1 ]
  • (Z)-4-(2-cyclohexylvinyl)-N,N-dimethylaniline [ No CAS ]
  • (E)-4-(2-cyclohexylvinyl)-N,N-dimethylaniline [ No CAS ]
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