[ CAS No. 134532-03-9 ] {[proInfo.proName]}

Name: 134532-03-9|2'-Amino-[1,1'-binaphthalen]-2-ol|97%
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Quality Control of [ 134532-03-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 134532-03-9 ]

SDS Specification

Alternatived Products of [ 134532-03-9 ]

Product Details of [ 134532-03-9 ]

CAS No. :	134532-03-9	MDL No. :	N/A
Formula :	C₂₀H₁₅NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	285.34	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 134532-03-9 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	20
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	93.32
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.83
Log Po/w (XLOGP3) :	5.01
Log Po/w (WLOGP) :	4.96
Log Po/w (MLOGP) :	4.02
Log Po/w (SILICOS-IT) :	4.36
Consensus Log Po/w :	4.23

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-5.37
Solubility :	0.00121 mg/ml ; 0.00000424 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.72
Solubility :	0.000542 mg/ml ; 0.0000019 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.33
Solubility :	0.0000134 mg/ml ; 0.0000000471 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.93

Safety of [ 134532-03-9 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P273-P280-P305+P351+P338-P310-P391-P501	UN#:	3077
Hazard Statements:	H303-H318-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 134532-03-9 ]

* 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 [ 134532-03-9 ]

[ 134532-03-9 ] Synthesis Path-Downstream 1~7

1
[ 91-59-8 ]
[ 135-19-3 ]
[ 194-59-2 ]
[ 4488-22-6 ]
[ 134532-03-9 ]
[ 602-09-5 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2156 - 2163

2
[ 91-59-8 ]
[ 135-19-3 ]
[ 4488-22-6 ]
[ 134532-03-9 ]
[ 602-09-5 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 2035 - 2042

3
[ 134532-03-9 ]
[ 137848-28-3 ]
[ 137848-29-4 ]

Yield	Reaction Conditions	Operation in experiment
39%; 37%		To a solution of rac-2 (5.7 g, 20 mmol) in anhydrous acetone (100 mL), was added N-benzylcinchonidinium chloride (N-BC; 5.0 g, 12 mmol). The reaction mixture was refluxed for 12 h, and then cooled to 25 C. The resulting molecular complex of (R)-2-N-BC was collected by filtration, and then was washed with acetone (30 mL). The mother liquid was evaporated under reduced pressure to yield the enriched (S)-2. The (R)-2-N-BC was dissolved in 1N HCl (50 mL) and ethyl acetate (100 mL) by stirring for 10 min. The organic layer was washed with brine (20 mL) and dried over Na2SO4. After the solvent was evaporated under reduced pressure, the solid residue was recrystallized from benzene to afford (R)-2 (2.2 g, 39%). (S)-2 was extracted and purified using a similar method that described for (R)-2 (2.1 g, 37%). Enantiomeric purities were obtained by chiral HPLC (eluents: hexane:IPA = 80:20 v/v, flow rate: 1 mL min-1, monitoring wavelength: 256 nm). Each fraction at 11 min and 22 min was attributed to (R)-2 and (S)-2 with > 99% ee (Figure S1). (R)-2: [alpha]D25 = +124.0 (c 1.0, THF); 1H-NMR (300 MHz, CDCl3). delta = 3.73 (s, 2H, binaphthyl-NH2), 5.12 (s, 1H, binaphthyl-OH), 7.05 (d, 1H, J = 7.2 Hz, aromatic ring), 7.14-7.40 (m, 8H, aromatic ring), 7.79-7.95 (m, 4H, aromatic ring); 13C-NMR (75 MHz, CDCl3): delta = 108.47, 114.21, 117.67, 118.13, 122.73, 123.62, 123.70, 124.50, 126.39, 127.28, 128.21, 128.28, 128.32, 129.47, 130.32, 130.57, 133.15, 134.07, 143.67, 151.78. (S)-2: [alpha]D25 = -122.0 (c 1.0, THF); 1H-NMR (300 MHz, CDCl3). delta = 3.74 (s, 2H, binaphthyl-NH2), 5.12 (s, 1H, binaphthyl-OH), 7.05 (d, 1H, J = 7.2 Hz, aromatic ring), 7.14-7.40 (t, 8H, aromatic ring), 7.79-7.95 (m, 4H, aromatic ring); 13C-NMR (75 MHz, CDCl3): delta = 108.53, 114.22, 117.69, 118.15, 122.75, 123.63, 123.72, 124.51, 126.95, 127.30, 128.23, 128.29, 128.34, 129.48, 130.34, 130.58, 133.16, 134.09, 143.67, 151.80.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 99 - 102
[2]Organic Letters,2005,vol. 7,p. 5821 - 5823

4
[ 134532-03-9 ]
[ 2492-87-7 ]
2-amino-2'-hydroxy-1,1'-binaphthyl 2'-O-β-D-glucoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With Aloearborescensglycosyltransferase*GT3; UDP; Cleland's reagent; In aq. buffer; at 30℃; for 12.0h;pH 7.4;Enzymatic reaction;	The model reaction was performed with 4-nitrophenyl-beta-D-glucopyranoside (7) as a ?sugar donor? and 2-amino-2'-hydroxy-1,1'-binaphthalene (5) as an acceptor (Figure S5) (50 mM Tris-HCl buffer, pH 7.4; 1 mM DTT; 100 muM 7 ; 10 muM UDP; 50 muM 5; 0.5 mg purified AaGT3; 30 oC for 12 h). Aliquots were withdrawn, stopped by methanol addition and analyzed by HPLC-UV/MS as described.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2118 - 2121

5
[ 602-09-5 ]
[ 194-59-2 ]
[ 134532-03-9 ]

Yield	Reaction Conditions	Operation in experiment
8%; 85%	With ammonium hydroxide; ammonium sulfite monohydrate; at 200℃; for 5h;Autoclave;	General procedure: Racemic 2,2'-dihydroxy-1,1'-binaphthyl (rac-BINOL, 5.0 g, 17.5 mmol), ammonium sulfite monohydrate (AR, 23.5 g, 175 mmol) and aqueous ammonia (32 mL, 464 mmol)Was placed in an autoclave.The mixture in the autoclave was stirred at the reaction temperature and reaction time described in Table 1. The reaction mixture was cooled to 25 C., and the resulting solid was washed with water and filtered.By recrystallizing the filtrate with benzene,Racemic 2-amino-2'-hydroxy-1,1'-binaphthyl (rac-NOBIN) and DBC were separated.The reaction yield was calculated by chiral HPLC. In addition, the isolation yield of the compound after recrystallization from benzene was calculated. These reaction yields and isolation yields are described in Table 1.
	With ammonium sulfite monohydrate; ammonia; In water; at 200℃;Autoclave;	1 (2.0 g, 6.9 mmol) and the aminating reagent (AR; (NH4)2SO3·H2O:NH3aq. = 1:2.6 mol/mol, equivalent ratio of 1:AR = 1:10 to 1:36 mol/mol) were placed in the autoclave. The mixture was stirred at 200 or 220 C at various reaction times. After the mixture was cooled to 25 C, the crude products were washed with water, and were collected by filtration. Separation of 2 and 3 was achieved by recrystallization from benzene. Reaction time, reaction temperature, equivalent ratio of 1:AR, reaction conversion, and isolated yields for each experiment were listed in Table 1. 2: 1H-NMR (300 MHz, CDCl3): delta = 3.75 (s, 2H, binaphthyl-NH2), 5.18 (s, 1H, binaphthyl-OH), 7.03-7.06 (d, 1H, J = 7.2 Hz, aromatic ring), 7.14-7.40 (m, 8H, aromatic ring), 7.79-7.94 (m, 4H, aromatic ring); 13C-NMR (75 MHz, CDCl3): delta = 108.65, 114.19, 117.68, 118.15, 122.75, 123.62, 123.71, 124.49, 126.39, 127.28, 128.21, 128.31, 128.35, 129.46, 130.33, 130.55, 133.15, 134.60, 143.54, 151.78. 3: mp: 159 C (lit.S3 156-159 C); 1H-NMR (400 MHz, CDCl3): delta = 7.54 (dd, 2H, J = 8.0, 7.2 Hz, aromatic ring), 7.64 (d, 2H, J = 8.8 Hz, aromatic ring), 7.70 (dd, 2H, J = 7.2, 7.2 Hz, aromatic ring), 7.87 (d, 2H, J = 8.8 Hz, aromatic ring), 8.05 (d, 2H, J = 7.6 Hz, aromatic ring), 8.68 (s, 1H, DBC-NH), 9.23 (d, 2H, J = 8.4 Hz, aromatic ring); 13C-NMR (75 MHz, CDCl3): delta = 112.56, 117.62, 123.27, 125.15, 125.43, 126.78, 129.17, 129.92, 136.10; FT-IR (nu cm-1): 3400, 3000, 1600, 1400, 900, 675; HRMS calcd. for C20H13N ([M+Na]+): 290.0940, found: 290.0940.

Reference： [1]Patent: JP2019/43941,2019,A .Location in patent: Paragraph 0048-0053; 0061
[2]Tetrahedron Letters,2018,vol. 59,p. 99 - 102

6
[ 134532-03-9 ]
[ 194-59-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With ammonium sulfite monohydrate; ammonia; In water; at 200℃; for 240h;Autoclave;	Compound 2 (2.0 g, 7.0 mmol), (NH4)2SO3·H2O (22.5 g, 168 mmol) and NH3aq. (60 mL, 436 mmol) were placed in the autoclave, and then the reaction mixture was stirred for 10 days at 200 C (a, entry 1 in Table 2) or at 190 C (b, entry 2 in Table 2). The resulting product was washed with water, and then was dissolved in benzene. The solvent was evaporated under reduced pressure to afford 3. Conversion: 99% (entry 1, Figure S14) and 73% (entry 2, Figure S15), isolated yield: 96% (1.8 g, entry 1) and 69 % (1.3 g, entry 2), respectively.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 99 - 102

7
[ 134532-03-9 ]
[ 137848-28-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5244 - 5248

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[ CAS No. 134532-03-9 ] {[proInfo.proName]}

Quality Control of [ 134532-03-9 ]

Related Doc. of [ 134532-03-9 ]

Product Details of [ 134532-03-9 ]

Calculated chemistry of [ 134532-03-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 134532-03-9 ]

Application In Synthesis of [ 134532-03-9 ]

[ 134532-03-9 ] Synthesis Path-Downstream 1~7

Precautionary Statements-General

Prevention

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Health hazards

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