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Product Details of [ 7310-97-6 ]

CAS No. :7310-97-6 MDL No. :MFCD00017606
Formula : C10H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :YSIIHTHHMPYKFP-UHFFFAOYSA-N
M.W : 194.18 Pubchem ID :606648
Synonyms :

Calculated chemistry of [ 7310-97-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.2
TPSA : 52.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 0.79
Log Po/w (WLOGP) : 1.33
Log Po/w (MLOGP) : 0.19
Log Po/w (SILICOS-IT) : 2.18
Consensus Log Po/w : 1.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.59
Solubility : 4.94 mg/ml ; 0.0254 mol/l
Class : Very soluble
Log S (Ali) : -1.48
Solubility : 6.5 mg/ml ; 0.0335 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.55
Solubility : 0.542 mg/ml ; 0.00279 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 7310-97-6 ]

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 [ 7310-97-6 ]

* 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 [ 7310-97-6 ]
  • Downstream synthetic route of [ 7310-97-6 ]

[ 7310-97-6 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 3752-97-4 ]
  • [ 7310-97-6 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: With hexamethylenetetramine In chloroform for 24 h; Reflux
Stage #2: With acetic acid In chloroform; water at 90℃; for 24 h;
To a solution of 1,4-dimethoxybenzene (1) (10.0 g,72.3 mmol) in 1,4-dioxane (30 mL), HCHO solution (38percent inwater, 5 mL) and paraformaldehyde (3.0 g, 99.0 mmol) wereadded in turn [27]. The resulting mixture was heated to90 °C, concentrated HCl (2×5 mL) was added during 30 minintervals. Heating continued for 1 h and a further 30 mL ofconcentrated HCl was added. The reaction mixture wascooled to room temperature to afford a white precipitate,which was obtained by filtration and dried under vacuum.The crude product was recrystallized with acetone to giveproduct 1 (4.5 g, 26percent) as a white precipitate. A solution ofproduct 1 (15.0 g, 63.8 mmol) and hexamethylenetetramine(18.0 g, 127.6 mmol) in chloroform (50 mL) was stirred atreflux for 24 h. After cooling to r.t., the pale yellow precipitatewas collected by filtration and redissolved in water(30 mL). The aqueous solution was acidified withCH3COOH (10 mL) and stirred at 90 °C for 24 h. The mixturewas cooled to r.t. and extracted with DCM (200 mL).The organic phase was washed three times with H2O(200 mL) and dried over anhydrous Na2SO4. After solventevaporation, the residue was recrystallized from CH3CH2OHto yield DMA (5.5 g, 45percent) as a bright yellow solid. 1H NMR(300 MHz, CDCl3) δ 10.50 (s, 2H), 7.26 (s, 2H), 3.95 (s, 6H).13C NMR (101 MHz, CDCl3) δ 189.19, 155.73, 129.15,110.92, 77.33, 77.01, 76.70, 56.23. FTMS for C10H10O4:calcd, m/z 195.1 [M+1]+; Anal. Calcd. (194.1).
10%
Stage #1: With hexamethylenetetramine In chloroformReflux
Stage #2: With acetic acid In water for 12 h; Reflux
Stage #3: With hydrogenchloride In water for 8 h; Reflux
This precursor center was prepared in three synthetic steps, from a procedure involving small modifications of the method already reported [33] . Initially, we dissolved 24.1 g (0.10 mol) of I and 30.0 g (0.21 mol) of urotropine (hexamethylenetetramine) in 200 mL of chloroform. The mixture was refluxed overnight. At the end of this first stage, after leaving the mixture cool to room temperature, the solvent was removed under reduced pressure and the solid residue obtained was dissolved in 320 mL of a 50percent acetic acid aqueous solution, being refluxed subsequently for 12 h. In the last part of the process, 25 mL of concentrated HCl was dropwise added to the solution, which was then refluxed for 8 h. After cooling, we observed the formation of a yellow precipitate, which was filtered off, washed with cold water and ethanol and dried under vacuum. Yield: 2.1 g (∼10percent), m.p. 207 °C (literature m.p.: 207 °C). From the filtrate, anadditional 0.8 g of the product could be obtained; its m.p. was 200 °C. Thesubstance was used in the next step without further purification. Elemental analysis - Percentages found: C, 61.9; H, 5.2. Calcd. for C10H10O4: C, 61.9; H,5.2. Main IR bands (KBr): 3435, 3069, 3048, 2992, 2953, 2932, 2870, 2833, 1679,1503, 1483, 1466, 1408, 1398, 1302, 1131, 1042, 878, 660 cm-1. 1H NMR (CDCl3,300 MHz): 3.93 ppm (s, 6H, -OCH3); 7.44 ppm (s, 2H, aromatic ring); 10.48 ppm(s, 2H, -CHO).
Reference: [1] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 10, p. 2755 - 2756
[2] Science China Chemistry, 2018, vol. 61, # 7, p. 857 - 862
[3] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 984 - 992
[4] Journal of Molecular Structure, 2016, vol. 1106, p. 121 - 129
[5] Journal of the American Chemical Society, 1950, vol. 72, p. 2992
[6] Journal of the Chemical Society, 1950, p. 2141,2142,2144
[7] Journal of Physical Chemistry, 1996, vol. 100, # 50, p. 19303 - 19309
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2385 - 2394
  • 2
  • [ 68-12-2 ]
  • [ 150-78-7 ]
  • [ 7310-97-6 ]
YieldReaction ConditionsOperation in experiment
62%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 0℃; for 5.5 h; Inert atmosphere; Reflux
Stage #2: at -78℃; for 1 h; Inert atmosphere
A three-necked reactor equipped with a thermometer was charged with 7.0 g (50.67 mmol) of 1,4-dimethoxybenzene, 29.44 g (253.33 mmol) of N,N,N′,N′-tetramethylethylenediamine, and 280 ml of diethyl ether under a nitrogen stream to prepare a homogeneous solution. After cooling the solution to 0° C., 97.4 ml (253.33 mmol) of 2.6 M n-butyllithium (n-hexane solution) was added dropwise to the solution over 30 minutes. After the dropwise addition, the reaction mixture was reacted for 5 hours under reflux, and then cooled to −78° C. After the addition of 18.52 g (253.33 mmol) of N,N-dimethylformamide, the mixture was stirred at −78° C. for 1 hour. After the addition of 350 ml of a 3 N hydrochloric acid aqueous solution to the reaction mixture at −78° C., the mixture was heated to 25° C., and 300 ml of distilled water and 200 ml of a saturated sodium chloride solution were added to the mixture, followed by extraction with 700 ml of chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. The solvent was evaporated from the filtrate under reduced pressure using a rotary evaporator. The resulting solid was added to 100 ml of toluene. After stirring the mixture for 5 minutes, the resulting crystals were filtered off to obtain 6.1 g of an intermediate A as yellow crystals (yield: 62percent). (0225) The structure of the target product was identified by 1H-NMR. (0226) 1H-NMR (500 MHz, CDCl3, TMS, δ ppm): 10.51 (s, 2H), 7.46 (s, 2H), 3.95 (s, 6H).
Reference: [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 7, p. 1157 - 1170
[2] Tetrahedron Letters, 2013, vol. 54, # 26, p. 3419 - 3423
[3] Patent: US2015/274647, 2015, A1, . Location in patent: Paragraph 0223-0226
[4] Organometallics, 2012, vol. 31, # 9, p. 3636 - 3646
[5] New Journal of Chemistry, 2016, vol. 40, # 7, p. 5877 - 5884
[6] Patent: CN107382905, 2017, A, . Location in patent: Paragraph 0008; 0081; 0087; 0088
  • 3
  • [ 2674-34-2 ]
  • [ 68-12-2 ]
  • [ 7310-97-6 ]
YieldReaction ConditionsOperation in experiment
30%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h;
Stage #2: at -78 - 20℃; for 15 h;
1,4-Dibromo-2,5-dimethoxybenzene (2.0 g, 6.76 mmol) was added dissolved in THF 35 mL, it was added dropwise a 1.6 M BuLi slowly at -78 . After stirring the reaction solution for 2 hours at -78 , it was added dropwise to DMF (2.8 mL, 33.7 mmol). The reaction solution is stirred at room temperature for 15 hours (20 ). 2 N HCl in a 20 mL reaction mixture was stirred slowly dropping off. The resulting solid was then filtered under reduced pressure, dried to obtain a 2,5-dimethoxyterephthalaldehyde 267 mg (30percent).
Reference: [1] Organic Letters, 2011, vol. 13, # 19, p. 5208 - 5211
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11310 - 11315[3] Angew. Chem., 2018, vol. 130, p. 11480 - 11485,6
[4] Organic and Biomolecular Chemistry, 2003, vol. 1, # 7, p. 1157 - 1170
[5] Patent: KR101493823, 2015, B1, . Location in patent: Paragraph 0107-0109
[6] Journal of Materials Chemistry A, 2017, vol. 5, # 44, p. 22933 - 22938
[7] Journal of Materials Chemistry A, 2018, vol. 6, # 2, p. 374 - 382
  • 4
  • [ 50874-27-6 ]
  • [ 7310-97-6 ]
YieldReaction ConditionsOperation in experiment
34%
Stage #1: With hexamethylenetetramine In chloroform for 3.5 h; Reflux
Stage #2: With acetic acid In water for 4.5 h; Reflux
2,5-Dimethoxy-1,4-benzenedicarboxaldehyde (2)
A mixture of hexamethylenetetramine (12.60 g, 90 mmol), 1 (9.72 g, 30 mmol) and CHCl3 (200 mL) was heated under reflux for 3.5 h, the solvent was evaporated under reduced pressure and 50percent acetic acid (200 mL) was added to the residue, heated under reflux for 4.5 h, then concentrated hydrochloric acid (10 mL) was added to the mixture, cooled to room temperature, extracted with CHCl3 and dried with anhydrous sodium sulfate.
after the solvent was evaporated under reduced pressure and the residue was recrystallized from ethyl alcohol to give bright yellow needle crystals (1.98 g, 34.0percent).
m.p. = 202-203 °C (Lit. m.p. = 201 °C
[32]
); 1H NMR (500 MHz, CDCl3) δ: 10.52 (s, 2H), 7.47 (s, 2H), 3.96 (s, 6H); FT-IR (KBr) v/cm-1: 3047, 2985, 2953, 2870, 1679, 1483, 1411, 1396, 1301, 1214, 1130, 1027, 878, 660.
Reference: [1] Synthesis, 1984, vol. NO. 9, p. 747 - 752
[2] Tetrahedron, 1983, vol. 39, # 5, p. 781 - 792
[3] Synthetic Communications, 2005, vol. 35, # 1, p. 49 - 53
[4] Journal of Molecular Structure, 2015, vol. 1093, p. 33 - 38
[5] European Journal of Organic Chemistry, 1998, # 4, p. 595 - 604
[6] New Journal of Chemistry, 2014, vol. 38, # 7, p. 3042 - 3049
[7] Patent: WO2015/163817, 2015, A1, . Location in patent: Paragraph 00328-00329
[8] Tetrahedron, 2017, vol. 73, # 20, p. 2886 - 2893
[9] Journal of Photochemistry and Photobiology A: Chemistry, 2017, vol. 346, p. 194 - 205
[10] Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 364, p. 705 - 714
  • 5
  • [ 2591-86-8 ]
  • [ 150-78-7 ]
  • [ 7310-97-6 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; ethyl acetate at 0℃; Inert atmosphere; Reflux
Stage #2: at 0 - 20℃; for 1 h;
To a solution of 1-1 1 ,4-dimethoxybenzene (11.5 g, 83.26 mmol, 1 eq) in distilled Et20(276 mL) was added TMEDA (37,4 mL, 249.78 mmol, 3 eq). At 000, nBuLi at 2.5 M inhexane (100 mL, 249.78 mmol, 3 eq) was added dropwise. The mixture was stirred atreflux overnight under inert atmosphere. At 000, 1-formylpiperidine (27.74 mL, 249.78mmol, 3 eq). was added dropwise. The mixture was stirred at room temperature for 1 h.Following the addition of distilled water (300 mL) and HCI 3 M (57.5 mL), the mixture was extracted with hot CHCI3 (300 mLx4). The organic phase was dried over an hydrous Na2SO4 and filtered. After removing the solvent, the remaining residue was purified by recrystallization in CHCI3 to give an orange solid (9.51 g, 51 percent).1H NMR (300 MHz, ODd3) 6 ppm = 10.51 (s, 2 H, CHO), 7.46 (s, 2 H, Ar), 3.95 (s, 6 H,OH3) data matched with literature reference
Reference: [1] Patent: WO2017/211985, 2017, A1, . Location in patent: Page/Page column 35; 36
  • 6
  • [ 4394-85-8 ]
  • [ 2674-34-2 ]
  • [ 7310-97-6 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 37, p. 11241 - 11248
  • 7
  • [ 150-78-7 ]
  • [ 7310-97-6 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 37, p. 11241 - 11248
[2] European Journal of Organic Chemistry, 1998, # 4, p. 595 - 604
[3] Journal of Medicinal Chemistry, 1984, vol. 27, # 8, p. 1071 - 1077
[4] Tetrahedron, 1983, vol. 39, # 5, p. 781 - 792
[5] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 10, p. 2755 - 2756
[6] New Journal of Chemistry, 2014, vol. 38, # 7, p. 3042 - 3049
[7] Journal of Molecular Structure, 2016, vol. 1106, p. 121 - 129
[8] Patent: WO2015/163817, 2015, A1,
[9] Tetrahedron, 2017, vol. 73, # 20, p. 2886 - 2893
[10] Journal of Materials Chemistry A, 2018, vol. 6, # 2, p. 374 - 382
[11] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 984 - 992
[12] Journal of Photochemistry and Photobiology A: Chemistry, 2017, vol. 346, p. 194 - 205
[13] Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 364, p. 705 - 714
[14] Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11310 - 11315[15] Angew. Chem., 2018, vol. 130, p. 11480 - 11485,6
  • 8
  • [ 3752-97-4 ]
  • [ 7310-97-6 ]
  • [ 120475-79-8 ]
Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2007, vol. 62, # 1, p. 66 - 74
  • 9
  • [ 51829-43-7 ]
  • [ 7310-97-6 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 4, p. 1053 - 1059
[2] Journal of Organic Chemistry, 1987, vol. 52, # 24, p. 5364 - 5374
  • 10
  • [ 114558-97-3 ]
  • [ 7310-97-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2385 - 2394
[2] Journal of Physical Chemistry, 1996, vol. 100, # 50, p. 19303 - 19309
  • 11
  • [ 52251-27-1 ]
  • [ 7310-97-6 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 4, p. 1053 - 1059
  • 12
  • [ 67-56-1 ]
  • [ 51829-43-7 ]
  • [ 7310-97-6 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 4, p. 1053 - 1059
  • 13
  • [ 123-31-9 ]
  • [ 7310-97-6 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 26, p. 3419 - 3423
  • 14
  • [ 51560-21-5 ]
  • [ 93-61-8 ]
  • [ 7310-97-6 ]
  • [ 90064-47-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 8, p. 1071 - 1077
  • 15
  • [ 90064-46-3 ]
  • [ 93-61-8 ]
  • [ 90064-48-5 ]
  • [ 7310-97-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 8, p. 1071 - 1077
  • 16
  • [ 28221-89-8 ]
  • [ 7310-97-6 ]
Reference: [1] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 743,747
  • 17
  • [ 1951-36-6 ]
  • [ 77-78-1 ]
  • [ 7310-97-6 ]
Reference: [1] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 743,747
  • 18
  • [ 90064-46-3 ]
  • [ 93-61-8 ]
  • [ 90064-48-5 ]
  • [ 7310-97-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 8, p. 1071 - 1077
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