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[ CAS No. 602-09-5 ] {[proInfo.proName]}

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Chemical Structure| 602-09-5
Chemical Structure| 602-09-5
Structure of 602-09-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 602-09-5 ]

CAS No. :602-09-5 MDL No. :MFCD00004068
Formula : C20H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PPTXVXKCQZKFBN-UHFFFAOYSA-N
M.W : 286.32 Pubchem ID :11762
Synonyms :

Calculated chemistry of [ 602-09-5 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 20
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 90.94
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.98
Log Po/w (XLOGP3) : 5.34
Log Po/w (WLOGP) : 5.07
Log Po/w (MLOGP) : 4.02
Log Po/w (SILICOS-IT) : 4.6
Consensus Log Po/w : 4.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.59
Solubility : 0.000743 mg/ml ; 0.00000259 mol/l
Class : Moderately soluble
Log S (Ali) : -5.94
Solubility : 0.000327 mg/ml ; 0.00000114 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.11
Solubility : 0.0000222 mg/ml ; 0.0000000776 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 602-09-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310+P330-P302+P352-P305+P351+P338 UN#:2811
Hazard Statements:H301-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 602-09-5 ]

* 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.

  • Upstream synthesis route of [ 602-09-5 ]
  • Downstream synthetic route of [ 602-09-5 ]

[ 602-09-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 7693-46-1 ]
  • [ 602-09-5 ]
  • [ 5070-13-3 ]
  • [ 138537-48-1 ]
Reference: [1] Chemistry Letters, 1991, # 12, p. 2091 - 2094
  • 2
  • [ 602-09-5 ]
  • [ 74866-28-7 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 27, p. 7932 - 7934
[2] Tetrahedron Letters, 1998, vol. 39, # 28, p. 5039 - 5040
[3] Organic Syntheses, 1989, vol. 67, p. 20 - 20
[4] European Journal of Organic Chemistry, 2010, # 9, p. 1669 - 1680
  • 3
  • [ 602-09-5 ]
  • [ 74866-28-7 ]
  • [ 721457-68-7 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 20, p. 4387 - 4397
  • 4
  • [ 603-35-0 ]
  • [ 602-09-5 ]
  • [ 74866-28-7 ]
Reference: [1] Synthetic Communications, 2003, vol. 33, # 16, p. 2763 - 2767
  • 5
  • [ 1034-39-5 ]
  • [ 602-09-5 ]
  • [ 74866-28-7 ]
Reference: [1] Tetrahedron, 1984, vol. 40, # 8, p. 1245 - 1253
  • 6
  • [ 107-30-2 ]
  • [ 602-09-5 ]
  • [ 173831-50-0 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide for 0.833333 h; Cooling with ice
Stage #2: at 0℃; for 1.33333 h;
NaH (1.92 g, 80 mmol) was added to DMF (30 mL) in an ice bath. BINOL (1,1’-bi-2-naphthol) (10 g , 34 mmol) in THF (50 ml) was dropped to this solution for 20 min. After 30 min, chloromethyl methyl ether (6.4 g, 80 mmol) was dropped to this solution for 20 min. The reaction was monitored by TLC. After 1 h stirring, 3 was isolated from the organic layer by extraction of the reaction mixture with chloroform and water. The product 3 was further purified by silica gel column chromatography with a petroleum ether/ethyl acetate (5/1)mixture. Yield: 90percent.1H NMR (400 MHz, CDCl3) δ 7.95-7.93 (d, J = 9.6Hz, 2H), 7.87-7.85 (d, J = 8.4 Hz, 2H), 7.58-7.56 (d, J = 9.6 Hz, 2H),7.35-7.31 (m, 2H), 7.23-7.14 (m, 4H), 5.08-4.96 (q, J = 6.8 Hz, 4H), 3.13 (s,6H).
90%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil for 0.833333 h; Cooling with ice
Stage #2: for 1 h;
The reaction was carried out in an ice bath. Tetrahydrofuran (30 mL) was added to a solution of sodium hydride (1.92 g, 80 mmol)Three-necked flask. A solution of 1,1'-binaphthol (compound (1)) (10 g, 34 mmol) in tetrahydrofuran (50 mL) was dissolvedThe solution was slowly added dropwise to the reaction solution over a period of 20 minutes. After completion of the addition, the reaction was continued for 30 minutes, and then chloromethyl ether (6.4 g, 80 mmol) was slowly added dropwise to the reaction solution. The reaction was continued for about one hour and monitored by thin layer chromatography. After the reaction was complete, the reaction was quenched with water (20 mL). The organic material was extracted with dichloromethane and water and the solvent was removed. The compound (2) was isolated by column chromatography on silica gel using a mixture of petroleum ether and ethyl acetate (5: 1) as the eluent. Yield: 90percent.
71%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h; Inert atmosphere
Stage #2: at 20℃; for 4 h;
under nitrogen protection,2.5 g of binaphthol was dissolved in 100 ml of tetrahydrofuran,The solution was cooled to 0 ° C,Then slowly add 0.88 g of sodium hydride and stir for 15 minutes.Take 1.65 ml of 98percent chloromethyl ether slowly,The mixture was warmed to room temperature for 4 hours and quenched with water.Extracted with ethyl acetate, dried over anhydrous sodium sulfate,The column was purified by silica gel column to give 2.3 g of product as a 71percent yield.
63%
Stage #1: With sodium hydride In tetrahydrofuran for 1 h;
Stage #2: for 12 h;
To 18.3 g of sodium hydride was added 50 g (0.175 mol) of 2,2'-dihydroxy-1,1'-dinaphthyl and stirred under nitrogen in 1.0 L of dry tetrahydrofuran (THF). After 1 hour, 116 g of chloromethyl methyl ether was added to the heavy precipitate and the resulting mixture was stirred for about 12 hours and then filtered through a pad of celite. The filtrate was shaken with 500 ml of water and 1 L of methylene chloride. An aqueous layer formed and was extracted two times more with methylene chloride. The combined organic layers were washed with water saturated with potassium bicarbonate. The organic layer was dried and filtered through a squat column of alumina and the column filtrate was evaporated until crystals appeared. The crude product was purified on a silica gel column by elution with a methylene chloride/hexane solution. About 53.5 g (63percent) of 2,2'-bis(methoxymethoxy)-1,1'-dinaphthyl, m.p 93-94° C., 0.11 mol was collected. [00053] Next, 171 ml of 1.6 N butyllithium in hexane was added to a mixture of 41 g of the above bisacetal in 1 L of tetrahydrofuran and stirred under nitrogen at 0° C. for 45 minutes. The reaction mixture was then allowed to warm to 25° C. and 25.8 ml of dimethyl sulfate was added to the suspension and the mixture was stirred for 12 hours. About 30 ml of water saturated with sodium carbonate was added and the solvent was evaporated under reduced pressure at 50° C. [00054] The residue, in 300 ml of methylene chloride, was washed twice with water. An additional 300 ml of methylene chloride, 300 ml of methanol, and 25 ml of concentrated hydrochloric acid was added to the organic solution. The solution was stirred for 3 hours, and the solvent was evaporated. The yellow product was recrystallized from methylene chloride-hexane and was purified on a silica gel column (methylene chloride, hexane 1:1) to give 29.5 g (86percent) of (R)-3-3'-dimethyl-2,2'-dihydroxy-1,1'-dinaphthyl, m.p. 204-206° C.; 1HNMR:2.2(s.6H), 7.1(d.2H), 7.3(m.2H), 7.4(m.2H), 7.8(m.4H).

Reference: [1] Organic Letters, 2004, vol. 6, # 16, p. 2701 - 2704
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 19, p. 2161 - 2166
[3] Chemistry - A European Journal, 2018, vol. 24, # 48, p. 12607 - 12612
[4] Chemistry Letters, 1995, # 12, p. 1113 - 1114
[5] Organic Preparations and Procedures International, 1995, vol. 27, # 6, p. 685 - 690
[6] European Journal of Organic Chemistry, 2002, # 2, p. 319 - 326
[7] Tetrahedron Letters, 2014, vol. 55, # 2, p. 351 - 353
[8] Tetrahedron Letters, 2016, vol. 57, # 10, p. 1133 - 1137
[9] Patent: CN104478915, 2016, B, . Location in patent: Paragraph 0065; 0066
[10] Patent: CN104496997, 2016, B, . Location in patent: Paragraph 0047; 0049
[11] Patent: US6686479, 2004, B2, . Location in patent: Page column 10; 11
[12] Journal of the American Chemical Society, 1980, vol. 102, # 6, p. 2043 - 2052
[13] Journal of Chemical Research, 2005, # 12, p. 778 - 779
[14] Journal of the American Chemical Society, 2000, vol. 122, # 10, p. 2252 - 2260
[15] Tetrahedron Asymmetry, 2008, vol. 19, # 4, p. 459 - 466
[16] Tetrahedron, 2010, vol. 66, # 9, p. 1673 - 1677
[17] Journal of Molecular Catalysis A: Chemical, 2015, vol. 398, p. 407 - 412
[18] RSC Advances, 2015, vol. 5, # 128, p. 105851 - 105854
[19] Polymer, 2018, vol. 143, p. 184 - 189
[20] Journal of Polymer Science, Part A: Polymer Chemistry, 2018, vol. 56, # 12, p. 1282 - 1288
[21] Tetrahedron Letters, 2016, vol. 57, # 12, p. 1390 - 1395
  • 7
  • [ 150587-19-2 ]
  • [ 602-09-5 ]
  • [ 173831-50-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 10, p. 2382 - 2385
  • 8
  • [ 602-09-5 ]
  • [ 765278-73-7 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 7, p. 2680 - 2687
  • 9
  • [ 1608-26-0 ]
  • [ 602-09-5 ]
  • [ 157488-65-8 ]
Reference: [1] Tetrahedron Asymmetry, 1994, vol. 5, # 4, p. 699 - 708
[2] Heteroatom Chemistry, 2003, vol. 14, # 6, p. 546 - 550
  • 10
  • [ 602-09-5 ]
  • [ 265116-85-6 ]
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 10, p. 2252 - 2260
[2] Journal of the American Chemical Society, 2000, vol. 122, # 10, p. 2252 - 2260
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