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Structure of 2631-77-8

Chemical Structure| 2631-77-8

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Product Details of [ 2631-77-8 ]

CAS No. :2631-77-8
Formula : C7H4I2O2
M.W : 373.91
SMILES Code : O=CC1=CC(I)=CC(I)=C1O
MDL No. :MFCD00003321
InChI Key :MYWSBJKVOUZCIA-UHFFFAOYSA-N
Pubchem ID :75829

Safety of [ 2631-77-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 2631-77-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 59.29
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.83
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

2.88
Log Po/w (WLOGP)?

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

2.41
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.

2.57
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

3.44
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.63

Water Solubility

Log S (ESOL):?

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

-4.31
Solubility 0.0183 mg/ml ; 0.0000489 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-3.32
Solubility 0.178 mg/ml ; 0.000475 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

-3.61
Solubility 0.0909 mg/ml ; 0.000243 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

Yes
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

Yes
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.

-6.54 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

0.0
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

2.0 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<1.0
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)

1.82

Application In Synthesis of [ 2631-77-8 ]

* 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 [ 2631-77-8 ]

[ 2631-77-8 ] Synthesis Path-Downstream   1~36

  • 1
  • [ 2631-77-8 ]
  • [ 94-02-0 ]
  • [ 101422-40-6 ]
YieldReaction ConditionsOperation in experiment
With piperidine; In ethanol; General procedure: 3-Carbonyl coumarins were obtained by Knoevenagel cyclization between substituted salicylaldehydes (1 mmol) and methyl acetoacetate (1 mmol) or ethyl benzoylacetate (1 mmol) in ethanol (25 mL) with catalytic amounts of piperidine. The ethyl ester of coumarin-3-carboxylic acid was prepared by Knoevenagel reaction between diethyl malonate (1 mmol) and the appropriate salicylaldehyde (1 mmol) with catalytic amounts of piperidine in ethanol (50 mL). Then, if there was an hydroxyl group at position 7, etherification was performed by adding a suitable benzyl bromide (1 mmol) or cycloheptyl bromide (1 mmol), and potassium carbonate (1 mmol) in anhydrous acetone (100 mL), using N,N'-dicyclohexyl-18-crown-6-ether (1 mmol) as a chelating agent. Final products were purified by chromatography. Ethyl ester derivatives (1 mmol) were dissolved and stirred at room temperature in a solution of LiOH.H2O (6 mmol) in H2O/MeOH (1:5, v/v; 50 mL); then HCl 3 N (50 mL) was added. The suspension was filtered and the solid was dried under vacuum. 3-Carboxyhydrazido derivatives were obtained by dissolving at reflux 3-coumarin carboxylic acid (1 mmol) in thionyl chloride (20 mL). After solvent evaporation under vacuum, the reactive acyl chloride (1 mmol) was reacted with a suitable hydrazine hydrochloride (2 mmol) in the presence of sodium acetate (2 mmol) in H2O/CH3CN (1/4, v/v).
  • 2
  • [ 90-02-8 ]
  • [ 2631-77-8 ]
YieldReaction ConditionsOperation in experiment
72% With sodium periodate; sulfuric acid; iodine; potassium iodide; sodium sulfite; In water; acetic acid; at 25℃; for 3h; General procedure: Iodination of phenol (1d) in the presence of Na2SO3 (typical procedure). A 100-mL round-bottom flask was charged with a solution of 3 mmol of phenol in 10 mL of acetic acid, and a solution of KI3 and Na2SO3 (prepared preliminarily by addition of 3 mmol of iodine and 3 mmol of Na2SO3 to a solution of 3 mmol of potassium iodide in 3 mL of water) was added rapidly. At the same time, a solution of 3 mmol of NaIO4 in 5 mL of water was added, and 0.5 mL of sulfuric acid was rapidly added using a pressure-equalizing dropping funnel. The mixture was stirred at 25C, the progress of the reaction being monitored by TLC. When the reaction was complete, the mixture was poured into ice-cold water, and the solid product was separated by vacuum filtration, washed twice with deionized water, and dried.
  • 3
  • [ 2631-77-8 ]
  • [ 105-53-3 ]
  • [ 99970-76-0 ]
YieldReaction ConditionsOperation in experiment
With piperidine; In ethanol; General procedure: 3-Carbonyl coumarins were obtained by Knoevenagel cyclization between substituted salicylaldehydes (1 mmol) and methyl acetoacetate (1 mmol) or ethyl benzoylacetate (1 mmol) in ethanol (25 mL) with catalytic amounts of piperidine. The ethyl ester of coumarin-3-carboxylic acid was prepared by Knoevenagel reaction between diethyl malonate (1 mmol) and the appropriate salicylaldehyde (1 mmol) with catalytic amounts of piperidine in ethanol (50 mL). Then, if there was an hydroxyl group at position 7, etherification was performed by adding a suitable benzyl bromide (1 mmol) or cycloheptyl bromide (1 mmol), and potassium carbonate (1 mmol) in anhydrous acetone (100 mL), using N,N'-dicyclohexyl-18-crown-6-ether (1 mmol) as a chelating agent. Final products were purified by chromatography. Ethyl ester derivatives (1 mmol) were dissolved and stirred at room temperature in a solution of LiOH.H2O (6 mmol) in H2O/MeOH (1:5, v/v; 50 mL); then HCl 3 N (50 mL) was added. The suspension was filtered and the solid was dried under vacuum. 3-Carboxyhydrazido derivatives were obtained by dissolving at reflux 3-coumarin carboxylic acid (1 mmol) in thionyl chloride (20 mL). After solvent evaporation under vacuum, the reactive acyl chloride (1 mmol) was reacted with a suitable hydrazine hydrochloride (2 mmol) in the presence of sodium acetate (2 mmol) in H2O/CH3CN (1/4, v/v).
  • 4
  • (1S)-1-(β-naphthylmethyl)-1,2-ethylenediamine [ No CAS ]
  • [ 2631-77-8 ]
  • N,N'-bis(3',5'-diiodosalicylidene)-(1S)-(β-naphthylmethyl)-1,2-ethylenediamine [ No CAS ]
  • 5
  • (1S)-(α-naphthylmethyl)-1,2-ethylenediamine dihydrochloride [ No CAS ]
  • [ 2631-77-8 ]
  • N,N'-bis(3',5'-diiodosalicylidene)-(1S)-(α-naphthylmethyl)-1,2-ethylenediamine [ No CAS ]
  • 6
  • [ 2631-77-8 ]
  • [ 62779-70-8 ]
  • N,N'-bis(3',5'-diiodosalicylidene)-(1S)-phenyl-1,2-ethylenediamine [ No CAS ]
  • 7
  • [ 2631-77-8 ]
  • [ 85612-60-8 ]
  • N,N'-bis(3',5'-diiodosalicylidene)-(1S)-benzyl-1,2-ethylenediamine [ No CAS ]
  • 8
  • [ 2631-77-8 ]
  • [ 208725-29-5 ]
  • N,N'-bis(3',5'-diiodosalicylidene)-[1R-(1α,2α,5α)]-2-amino-7,7-dimethyl-2-bicyclo[3.3.1]heptane-ethanamine [ No CAS ]
  • 9
  • 2,6-bis[4-hydroxy-3,5-di(tert-butyl)phenyl]aniline [ No CAS ]
  • [ 2631-77-8 ]
  • 3,5,3'',5''-Tetra-tert-butyl-2'-[1-(2-hydroxy-3,5-diiodo-phenyl)-meth-(E)-ylidene]-amino}-[1,1';3',1'']terphenyl-4,4''-diol [ No CAS ]
  • 10
  • [ 2631-77-8 ]
  • [ 98-59-9 ]
  • [ 904324-23-8 ]
  • 11
  • [ 2631-77-8 ]
  • [ 958876-86-3 ]
  • [ 958635-03-5 ]
  • 12
  • [ 2631-77-8 ]
  • [ 958634-97-4 ]
  • [ 958635-08-0 ]
  • 13
  • [ 2631-77-8 ]
  • [ 1097192-03-4 ]
  • C29H27I2N3O [ No CAS ]
  • 14
  • [ 2631-77-8 ]
  • [ 1097192-02-3 ]
  • C25H15F2I2NO [ No CAS ]
  • 15
  • [ 2631-77-8 ]
  • [ 17798-71-9 ]
  • C27H21I2NO [ No CAS ]
  • 16
  • [ 2631-77-8 ]
  • [ 340187-66-8 ]
  • C27H21I2NO3 [ No CAS ]
  • 17
  • [ 2631-77-8 ]
  • [ 340187-67-9 ]
  • C33H33I2NO [ No CAS ]
  • 18
  • [ 2631-77-8 ]
  • [ 109-77-3 ]
  • [ 122-52-1 ]
  • [ 1170000-24-4 ]
  • 19
  • [ 2631-77-8 ]
  • [ 590-17-0 ]
  • [ 944682-30-8 ]
  • 20
  • [ 2631-77-8 ]
  • [ 106-96-7 ]
  • [ 359644-42-1 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 10h; General procedure: Salicylaldehyde was dissolved in DMF (5 mL, distilled from CaH2). Propargyl bromide andpotassium carbonate were added at 0 C, and the reaction mixture was stirred at roomtemperature for prescribed time indicated. After completion of the reaction (monitored byTLC), water (10 mL) was added and extracted with ethyl acetate (3x15 mL). The combinedorganic layers were washed with brine, dried over Na2SO4, filtered, and concentrated underreduced pressure. Subsequent column chromatography using silica gel with ethylacetate-hexanes yielded the corresponding 2-(prop-2-ynyloxy)benzaldehydes in good yield.
  • 21
  • [ 2631-77-8 ]
  • [ 112245-13-3 ]
  • [ 778625-56-2 ]
YieldReaction ConditionsOperation in experiment
79% With sodium sulfate; In ethanol; for 16h;Reflux; General procedure: Commercially available salicylaldehyde (1 mmol) and sodium sulfate(0.5 g) were added to a solution of (S)-tert-leucinol (1 mmol) or Lvalinol(1 mmol) in ethanol (20 mL). The reaction mixture was stirredunder reflux for 16 h, filtered, and concentrated under reducedpressure. The reaction mixture was then dissolved in dichloromethane(10 mL) and washed with water (3 × 10 mL) and brine (15 mL). Theorganic layer was dried and concentrated under reduced pressure toleave the crude product, which was purified by column chromatographyon silica gel (8:2 hexane/ethyl acetate) to yield the pure ligand. (S)-2-(N-3,5-Diiodosalicylidene)-amino-3,3-dimethyl-1-butanol(10, Table 4):.22,36 Yellow solid, 79%, mp 164-165 C (lit. mp163-164);22 1H NMR δH (300 MHz) 1.00 (9H, s), 2.53 (1H, brs),3.08 (1H, dd, J = 9.5 and 2.5 Hz), 3.68 (1H, dd, J = 11.1 and 9.8 Hz),3.93-4.07 (1H, brm), 7.51 (1H, d, J = 2.1 Hz), 8.01 (1H, d, J = 2.1Hz), 8.10 (1H, s); IR νmax/cm-1 (KBr) 3320, 2965, 1638, 1479, 1217,1060; [α]D20 = -18.5 (c 0.1, acetone), lit.22 [α]D20 = -16.6 (c 1.0 for S inacetone).
  • 22
  • [ 2631-77-8 ]
  • [ 5509-65-9 ]
  • [ 894810-11-8 ]
YieldReaction ConditionsOperation in experiment
65% With formic acid; In ethanol; at 20℃; for 3h; General procedure: To a stirred solution of 3,5-dichlorosalicylaldehyde (2.00 g,10.47 mmol) in ethanol (20 mL) was slowly added 2,6-difluoroaniline (1.37 g, 10.47 mmol) at room temperature in the presence of trace amount of formic acid as a catalyst. The reaction mixture was stirred at room temperature for 3 h. Orange crystals were formed and then filtered. The product was obtained in 64%yield (2.74 g). 1H NMR data (500.13 MHz, CDCl3, 298 K): δ 13.77(s, 1H, OH), 8.87 (s, 1H, NCH), 7.48 (d, 4JHH 2.5, 1H, salicyl-H), 7.31(d, 4JHH 2.5, 1H, salicyl-H), 7.23e7.16 (m, 1H, aniline-H), 7.06e6.98(m, 2H, aniline-H). 13C NMR data (125.77 MHz, CDCl3, 298 K):δ 166.50 (HCN), 157.61 (d, CF), 156.22 (COH), 155.57 (d, CF), 133.61(salicyl-CH), 130.50 (salicyl-CH), 128.15 (t, aniline-CN), 124.14(t, CCHN), 123.90 (CCl), 123.35 (CCl), 120.68 (aniline-CH), 112.64(d, aniline-CH). Elemental analysis for C13H7Cl2F2NO: C, 51.68; H,2.34; N, 4.64%. Found C, 51.89; H, 2.31; N, 4.66%.
  • 23
  • [ 2631-77-8 ]
  • [ 109-76-2 ]
  • [ 1088976-74-2 ]
YieldReaction ConditionsOperation in experiment
68% In ethanol;Reflux; General procedure: To a stirred ethanolic (25 mL) solution of 3,5-dihalosalicylaldehyde(2 mmol) was added an ethanolic (25 mL) solutionof the diamine (1 mmol). The reaction mixture was refluxedfor 1-3 h at 80-90 C in a water bath. The resulting solutionwas cooled to room temperature, and the resulting precipitatewas collected by suction filtration and washed withcold ethanol (3 × 10 mL) to afford the desired Schiff base. Single crystals of the isen, bspn and isbn suitable for X-ray diffraction experiments were obtained by slow evaporationof the hot ethanolic solution of the compounds.
  • 24
  • [ 2631-77-8 ]
  • [ 109-77-3 ]
  • C10H4I2N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With piperidine; In ethanol; at 20℃; General procedure: To a stirred solution of salicylaldehyde (1 mmol) and malononitrile (1 mmol) in ethanol (5 ml), was added piperidine (40 mol %) and allowed stirring until the formation of precipitate. To this formed precipitate, was added azido ketone (1.5 mmol) and stirring was continued for the specified time. The progress of the reaction was monitored by thin layer chromatography using ethyl acetate: pet ether (3: 7) as an eluent. After the specified reaction time the ethanol was removed under vacuo and the crude product was purified by flash chromatography on silica gel (neutralized with five drops triethyl amine) (petroleum ether-ethyl acetate, 90/10-75/25).
  • 25
  • [ 3731-51-9 ]
  • [ 2631-77-8 ]
  • 2,4-diiodo-6-((pyridin-2-ylmethylimino)methyl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In methanol; at 30℃; for 0.5h; The ligand (L) was prepared by a slow addition of 2-picolyamine(0.1446 g, 1 mmol) in methanol to 3,5-diiodosalicyaldehyde (0.5 g,1 mmol). The mixture was stirred for 30 min at 30 C and the progressof reaction was monitored by TLC. The obtained yellow precipitatewas filtered off, washed thoroughly with methanol anddried in vacuo: Yield: 84%; M.P: 110 C; Color: yellow. IR (KBr,cm1): 3448 (AOH), 1633 (CHN), 1573(m), 1462(w) (CC),1437 (CN), 1429, 1356(m), 1276(m) (CAO).1H NMR (300 MHz, CDCl3) d:14.70 (s, 1H, OH), 8.56 (d, J = 4.8 Hz,1H, ArH), 8.32 (s, 1H, ACN), 8.04 (d, J = 2.1 Hz, 1H, ArH), 7.69 (td, J= 7.7, 1.8 Hz, 1H, ArH), 7.55 (d, J = 2.1 Hz, 1H, ArH), 7.33 (d, J= 7.8 Hz, 1H, ArH), 7.24-7.16 (m, 1H, ArH), 4.93 (s, 2H, ACH2).UV-vis (MeOH, nm) 235, 344, 406; ESI-MS (MeOH) Foundm/z = 464.75 [M + H] (calculated m/z = 463.89 for M+).
  • 26
  • [ 107-10-8 ]
  • [ 2631-77-8 ]
  • [ 1370047-13-4 ]
YieldReaction ConditionsOperation in experiment
75% With diphenyl hydrogen phosphite; In toluene; for 3h;Reflux; General procedure: Taking I-4a for example, 2-hydroxybenzaldehye (1 mmol), ethylamine (1 mmol), and diphenyl phosphite (1.2 mmol) were ordinally added in a single-port round bottom flask (25 mL), equipped with a reflux condenser and a drying tube, and then anhydrous toluene (3 mL) was added. The residue was precipitated after 2 h under reflux. Reflux the reaction mixture gently for a further hour. After cooling, methanol (3 mL) was added to the reaction and was filtered out. Then the filtered residue was washed with methanol (44 mL). The pure product I-4a could be obtained and dried in a vacuum dryer. The other products were obtained by this similar method.
  • 27
  • [ 2631-77-8 ]
  • [ 109-73-9 ]
  • [ 1370047-14-5 ]
YieldReaction ConditionsOperation in experiment
69% With diphenyl hydrogen phosphite; In toluene; for 3h;Reflux; General procedure: Taking I-4a for example, 2-hydroxybenzaldehye (1 mmol), ethylamine (1 mmol), and diphenyl phosphite (1.2 mmol) were ordinally added in a single-port round bottom flask (25 mL), equipped with a reflux condenser and a drying tube, and then anhydrous toluene (3 mL) was added. The residue was precipitated after 2 h under reflux. Reflux the reaction mixture gently for a further hour. After cooling, methanol (3 mL) was added to the reaction and was filtered out. Then the filtered residue was washed with methanol (44 mL). The pure product I-4a could be obtained and dried in a vacuum dryer. The other products were obtained by this similar method.
  • 28
  • [ 2631-77-8 ]
  • [ 23364-44-5 ]
  • [ 1397334-48-3 ]
YieldReaction ConditionsOperation in experiment
56% In methanol; at 20℃; for 72h; To a solution of (1S,2R)-(+)-2-amino-1,2-diphenylethanol (200.0 mg, 0.94 mmol, 1.0 equiv) in anhydrous methanol (3 mL) and MgSO4 (564.4 mg, 5.0 equiv) a solution of <strong>[2631-77-8]3,5-diiodosalicylaldehyde</strong> (350.6 mg, 0.94 mmol, 1.0 equiv) in methanol (14 mL) was added dropwise. After the reaction mixture was stirred for 3 d at room temperature, MgSO4 was filtered off, and the solution was concentrated and purified by flash column chromatography (SiO2, PE/EtOAc 3:1) to afford the desired product in 56% yield (300.0 mg) as an orange foam. 1H NMR (300 MHz, CDCl3): δ=2.04 (br s, 1H), 4.48 (d, J=7.3 Hz, 1H), 5.00 (d, J=7.3 Hz, 1H), 7.19-7.39 (m, 11H), 7.77 (s, 1H), 7.98 (d, J=2.0 Hz, 1H), 14.44 (s, 1H). 13C NMR (100 MHz, CDCl3): 78.0, 79.3, 79.7, 87.3, 119.8, 127.0, 127.9, 128.3, 128.4, 128.9, 138.4, 139.7, 139.9, 148.7, 160.4, 163.6. FAB: m/z=570 [M+H]+.
  • 29
  • [ 2631-77-8 ]
  • [ 2033-24-1 ]
  • [ 98994-72-0 ]
YieldReaction ConditionsOperation in experiment
52% With piperdinium acetate; In ethanol; for 2h;Reflux; General procedure: A mixture of the appropriate aldehyde (8.06 mmol), Meldrum’s acid (1) (1.16 g, 8.06 mmol) and piperidinium acetate (29 mg, 0.2 mmol) in ethanol (25 mL) was stirred at room temperature for 20 mins and then heated under reflux for 2 h. The reaction mixture was allowed to cool to room temperature before being stirred at 0 C for another hour. The solid which precipitated out of solution was filtered off, washed thoroughly with ethanol and dried in vacuo to afford the desired product.
  • 30
  • [ 2631-77-8 ]
  • [ 143300-64-5 ]
  • [ 1370554-82-7 ]
YieldReaction ConditionsOperation in experiment
64% With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; Step 1: Synthesis of Intermediate, 2-[4-(diethylamino)piperidin-1-yl]methyl}- 4,6-diiodophenol 1: Sodium triacetoxyborohydride (8.56g, 38.4mmol) was added portionwise to a solution of <strong>[2631-77-8]2-hydroxy-3,5-diiodobenzaldehyde</strong> (9.8g, 26.0mmol),/V,/V-diethylpiperidin-4-amine (4.0g, 26.0mmol) and acetic acid (1 .5ml_, 26.0mmol) in dichloromethane (60ml_). After 4-5h of stirring at rt, the reaction was diluted with dichloromethane before being washed with saturated aqueous solution of NaHC03. The organic layer was dried over Na2S04, filtered and evaporated. The residue was purified on silica gel (dichloromethane/methanol 99/1 to 95/5 with 1 % triethylamine) to provide 2-[4-(diethylamino)piperidin-1 -yl]methyl}-4,6- diiodophenol (8.5g, 1 6.5mmol, 64% yield) as a beige foam.
  • 31
  • [ 2631-77-8 ]
  • [ 951322-70-6 ]
  • 4,6-diiodo-2-{(trans-2-(isoindolin-2-yl)-1,2-diphenylethylimino)methyl}phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In ethanol; at 20℃;Inert atmosphere; Schlenk technique; Molecular sieve; General procedure: To a mixture of salicylaldehyde 1a-f, 1,3-dihydro-α,β-diphenyl-2H-isoindole -2-ethanamine 2 (equivalent to 1a-f), and several 4 Å sieves in a septum capped Schlenk tube was added anhydrous ethanol (ca. 10 mL per mmol of 1a-f) via syringe at 20 C with stirring under nitrogen. After stirring the resulting mixture overnight, the solvent was removed under vacuum, and the residue was purified by flash chromatography on silica gel (Vethyl acetate/Vpetroleum ether = 1/20) to give the brown target ligands 3a-f.
  • 32
  • [ 2631-77-8 ]
  • C22H38N2O [ No CAS ]
  • C29H40I2N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% In methanol; at 40℃; for 12h;Inert atmosphere; General procedure: To a solution of 8 (1.73 g, 5 mmol) in MeOH (20 mL) was added salicylaldehyde (5 mmol) 9a-d and the resulting mixture was warmed to 40 C and stirred for 12 h. After cooling to 0 C, the precipitate was filtered off and washed with cold methanol to give the target ligand precursors H(La-d).
  • 33
  • [ 2631-77-8 ]
  • [ 5351-69-9 ]
  • 3,5-diiodosalicylaldehyde,N(4)-phenylthiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In methanol; for 3h;Reflux; The ligand was prepared by the following method. A solution of <strong>[2631-77-8]3,5-diodosalicylaldehyde</strong> (1 mmol, 0.4 g) in methanol (15 ml) was added dropwise to a solution of 4-phenylthiosemicarbazide (1 mmol, 0.17 g) in methanol (15 ml) with stirring at reflux. After being stirred for 3 h, the resulting white solids were removed by filtration, washed with cold ethanol and dried in vacuo over anhydrous CaCl2. M.p: 192 C, Yield: 80%.
  • 34
  • [ 2631-77-8 ]
  • [ 697-88-1 ]
  • 2-((4-bromo-2,6-dichlorophenylimino)methyl)-4,6-diiodophenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With acetic acid; In ethanol;Reflux; Schiff base ligand were synthesized by refluxing of 3,5 diiodosalicylaldehyde (0.01M) and 4-bromo-2,6-dichlorobenzenamine (0.01 M) in 50ml ethanol on water bath for 4-5 hours inpresence of 2-3 drops of glacial acetic acid. The reaction mixture was kept for overnight, where yellow color precipitate was obtained. It was filtered by whatmann paper, washed with distilled water then alcohol, dried in vacuum dessicator. Pure Schiff base was recrystallized from ethanol. The purity ofligand was checked by TLC.
  • 35
  • [ 2631-77-8 ]
  • [ 18162-48-6 ]
  • 2-((tert-butyldimethylsilyl)oxy)-3,5-diiodobenzaldehyde [ No CAS ]
  • 36
  • [ 120-72-9 ]
  • [ 2631-77-8 ]
  • [ 1076-38-6 ]
  • C24H13I2NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% General procedure: A mixture of salicylaldehyde (1 mmol), 4-hydroxycoumarin (1mmol), and L-proline (0.1 mmol) in EtOH (5 mL) was heated to reflux for 6 h. Indole or barbituric acid (1 mmol) was then added to the reaction mixture and reflux continued with stirring for a further 6-8 h (monitoring by TLC). The solid formed was filtered washed with EtOH then with H2O to afford analytically pure product.
 

Historical Records

Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Halogenation of Phenols • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reformatsky Reaction • Reimer-Tiemann Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 2631-77-8 ]

Aryls

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