2033-42-3|1-Iodo-2-naphthol| Ambeed

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Quality Control of [ 2033-42-3 ] Purity: 97% SDS Specification

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Product Details of [ 2033-42-3 ]

CAS No. :	2033-42-3
Formula :	C₁₀H₇IO
M.W :	270.07
SMILES Code :	OC1=C(I)C2=C(C=CC=C2)C=C1
MDL No. :	MFCD00046371
Boiling Point :	No data available
InChI Key :	JEVGGOSILOIIHN-UHFFFAOYSA-N
Pubchem ID :	16250

Safety of [ 2033-42-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 2033-42-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	58.69
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.93
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.15
Log P_o/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.	3.38
Log P_o/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	3.45
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.08

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.32
Solubility	0.013 mg/ml ; 0.0000482 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.	-3.58
Solubility	0.0716 mg/ml ; 0.000265 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	-4.45
Solubility	0.00963 mg/ml ; 0.0000356 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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.	-5.48 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	1.0 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<0.0
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)	2.06

Application In Synthesis of [ 2033-42-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2033-42-3 ]

[ 2033-42-3 ] Synthesis Path-Downstream 1~38

1
[ 2033-42-3 ]
[ 77-78-1 ]
[ 32721-21-4 ]

References: [1]Organic Letters,2008,vol. 10,p. 1333 - 1336.
[2]Journal of the American Chemical Society,1933,vol. 55,p. 3833,3835.
[3]Synlett,2003,p. 2005 - 2008.

2
[ 135-19-3 ]
[ 2033-42-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	With sulfuric acid; dihydrogen peroxide; potassium iodide; In methanol; at 0 - 20℃;	To a stirred solution of 2-naphthol (1.0g, 6.9 mmol) and conc. H2SO4 (0.54 mL 10.4 mmol) in CH3OH (20 mL) at 0 Cwas added KI (1.27 g, 7.62 mmol) and 30% H2O2 (1.56 mL, 13.9 mmol). The mixture was stirred overnight at room temperature, and then poured into CH3Cl. The mixture was washed with saturated aq. NaHSO3,with water, and dried over MgSO4, concentrated in vacuo. The crude product was purified by flash column chromatography using hexane and EtOAc to give 1-iodo-2-naphthol as light yellow solid (1.40 g, 74%), 1H NMR (300 MHz,CDCl3) d 7.91 (d, J = 8.6 Hz, 1H), 7.73-7.70 (m, 2H), 7.53 (dd, J = 7.1, 8.2 Hz, 1H), 7.36 (dd, J= 7.0, 8.1 Hz, 1H), 7.25-7.23 (m, peak merged with CDCl3, 1H), 5.79(s, 1H); 13C NMR (75 MHz, CDCl3) d 153.7, 134.7, 130.6, 130.2, 129.6, 128.3,128.1, 124.1, 116.4, 86.2; GC-MS m/z 270, 272 (M+).
31%	With sulfuric acid; dihydrogen peroxide; potassium iodide; In methanol; at 0℃; for 1h;	This procedure has been carried out according to the following article: Synthesis 2004, No. 11, 1869 - 1873. To a solution of H2S04 (554 pL, 10.40 mmol, 1.50 equiv) in MeOH (35 mL) was added naphthalen-2-ol (1.00 g, 6.93 mmol, 1.00 equiv). The reaction was cooled at 0VC. K1 ( 1.15 g, 6.93 mmol, 1.00 equiv) and H?Oz (30% wt, 1.42 mL, 13.86 mmol, 2.00 equiv) were added. The reaction was stirred at 0C for I hour. DCM was added and the organic mixture was washed with aqueous solution of NaHS03 (0.1M), water, brine, dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography (0 - 40% of DCM in Hexanes) to give the desired compound as grey solid in 31 % yield (580 mg). NMR (600 MHz, CDCb) 5 7.93 (d, /= 8.5 Hz, 1H), 7.77 - 7.72 (m, 2H), 7.55 (t, 7.4 Hz, 1H), 7.39 (t, J = 7.5 Hz, 110, 7.26 (d, 8.8 I, 1H), 5.79 (s, HD ppm. i3C NMR (151 MHz, CDCb) 5 153.86, 134.89, 130.76, 130.38, 129.78. 128.44, 128.35, 124.32, 116.57, 86.38 ppm. HRMS (ES-) calculated for CieHdD (M - H)' 268.9469, found 268.9467. IR (neat) v 3292, 1624, 1497, 1430, 1345, 1301 , 1237, 976, 924, 807, 744 cm"1.
	With N-iodo-succinimide;zirconium tetrachloride; In dichloromethane; at -78 - 20℃; for 2 - 3h;Conversion of starting material;	lodination using NIS has been found to be applicable for use with a wide range of aromatic starting materials or substrates. As shown in Table 3, the iodination provides good yields and regioselectivities. In Entry 2, trace di-iodinated products were observed.Table 3 ZrCU Catalyzed lodination of Aromatic Compounds by NIS4-I : 2,4-di-l (99 : 1 )b EPO <DP n="28"/>4-1 : 2,4-di-l(36: 64)bReaction conditions: Substrate (O 5 mmol), NIS (O 5 mmol), ZrCIj (5 mol o), CH2CI2 (4 mL)" Determined by 1H NMR. 0 See spectroscopic data for characterization

	With sulfuric acid; dihydrogen peroxide; potassium iodide; In methanol; at 0℃; for 2h;	General procedure: At 0 C, stirring,To a solution of concentrated H2SO4 (0.98 mL, 18.0 mmol) in MeOH (20 mL)KI (2.19 g, 13.2 mmol) was added to 2-naphthol compound J (12.0 mmol) in this order.And 30% H2O2 (2.72 mL, 24.0 mmol),The mixture was stirred at 0 C for about 2 hours.After monitoring the reaction by TLC,The mixture was diluted with water and extracted twice with 50 mL of DCM. The combined organic phases were washed sequentially with 20 mL of saturated Na2S2O3, 40 mL H2O and 50 mL brine.Dried over Na2SO4 and concentrated under reduced pressure, the residue was purified by recrystallization to give the product K.
	With N-iodo-succinimide; toluene-4-sulfonic acid; In dichloromethane; at 20℃; for 0.5h;	At room temperature, WX002-1 (5 g, 34.68 mmol) was dissolved in dichloromethane (70 mL), and then Niodosuccinimide(7.80 g, 34.68 mmol) and p-toluenesulfonic acid (1.98 g, 10.40 mmol) were added successively, andthe reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, water (50 mL) wasadded for dilution, the organic phase was collected after separation, and the aqueous phase was extracted with dichloromethane(50 mL 3 2). The organic phase was combined, dried over anhydrous sodium sulfate and filtered, and thesolvent was removed from the filtrate under reduced pressure to obtain the target intermediate WX002-2. 1H NMR (400MHz, CDCl3) δ: 7.96 (d, J = 8.4 Hz, 1H), 7.76 (dd, J = 3.2, 8.4 Hz, 2H), 7.58 (t, J = 7.7 Hz, 1H), 7.46-7.37 (m, 1H),7.32-7.24 (m, 1H), 4.95 (s, 1H).
	With sodium iodide; In aq. phosphate buffer; at 30℃; for 0.5h;pH 6;	The TiaM-catalyzed chlorination of 1 was carried out accordingto our previous report [23]. Halogenation reactionswere carried out in 1.5 mL Eppendorf microtubes at 30 C ina water bath (Yuhua, China) or an Eppendorf ThermoMixerC (Germany). The enzyme assay mixtures contained 40 μM1, 3.0 μM TiaM, 0.3 μM SsuE (a flavin reductase from E.coli [27]), 0.2 mM FAD, 8 mM NADH, 100 mM NaCl (or0.1 mM to 1 M NaI) in 100 mM potassium phosphate buffer(pH 6.0-8.0) or citrate buffer (pH 3.0-6.0) at a total volumeof 200 μL. After a period of incubation time (ranging from5 min to 3 h), products were extracted by adding 400 μLethyl acetate. The ethyl acetate extracts were evaporated todryness by vacuum. The dried reaction products were dissolvedin 250 μL methanol and subjected to HPLC analysison an Agilent 1260 Workstation. HPLC was carried out usinga reversed phase column (ACE SuperC18, 250×4.6 mm,UK) with UV detection at 270 nm under the following program:solvent system (solvent A, 10% acetonitrile in water supplementing with 0.08% formic acid; solvent B, 90%acetonitrile in water); 5% B to 100% B (linear gradient,023 min), 100% B (2325 min), 100% B to 5% B(2526 min), 5% B (2630 min); flowrate at 1 mL/min.

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3
[ 30089-00-0 ]
[ 2033-42-3 ]
[ 61351-11-9 ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 2201 - 2208.

4
[ 37746-78-4 ]
[ 2033-42-3 ]
[ 111726-54-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 20℃; for 12h;	At room temperature, the intermediate WX002-2 (9 g, 33.33 mmol) was dissolved in acetonitrile (150 mL), thenpotassium carbonate (9.21 g, 66.65 mmol) and ethyl 4-bromocrotonate (6.43 g, 33.33 mmol, 4.60 mL) were addedsuccessively, and the reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction,the reaction solution was filtered, the filtrate was collected, and the filter cake was washed with ethyl acetate (30 mL 32). The filtrate and washings were combined, the solvent was removed under reduced pressure, and the resulting residuewas purified by column chromatography (eluent: petroleum ether/ethyl acetate = 1/0-20/1, volume ratio) to obtain thetarget intermediate WX002-3. 1H NMR (400 MHz, CDCl3) δ: 8.17 (d, J = 8.4 Hz, 1H), 7.81 (d, J = 8.8 Hz, 1H), 7.75 (d,J = 8.0 Hz, 1H), 7.57 (ddd, J = 1.2, 7.0, 8.5 Hz, 1H), 7.42 (ddd, J = 1.1, 6.9, 8.1 Hz, 1H), 7.19-7.10 (m, 2H), 6.46 (td, J= 2.1, 15.7 Hz, 1H), 4.90 (dd, J = 2.0, 3.6 Hz, 2H), 4.25 (q, J = 7.2 Hz, 2H), 1.33 (t, J = 7.1 Hz, 3H).

References: [1]Canadian Journal of Chemistry,1987,vol. 65,p. 2019 - 2023.
[2]Patent: EP3848363,2021,A1 .Location in patent: Paragraph 0090; 0092.

5
[ 2033-42-3 ]
[ 72345-23-4 ]
[ 428509-74-4 ]

References: [1]Chemistry - A European Journal,2002,vol. 8,p. 3327 - 3330.
[2]Tetrahedron Asymmetry,2004,vol. 15,p. 2253 - 2261.

6
[ 2033-42-3 ]
[ 550-60-7 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 6393 - 6395.

7
[ 2033-42-3 ]
[ 135-19-3 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 6391 - 6392.
[2]Journal of Organic Chemistry,2005,vol. 70,p. 8590 - 8593.
[3]Journal of Organic Chemistry,2003,vol. 68,p. 9423 - 9432.

8
[ 90-15-3 ]
[ 2033-42-3 ]