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[ CAS No. 103-40-2 ] {[proInfo.proName]}

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Chemical Structure| 103-40-2
Chemical Structure| 103-40-2
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Product Details of [ 103-40-2 ]

CAS No. :103-40-2 MDL No. :MFCD00447717
Formula : C11H12O4 Boiling Point : -
Linear Structure Formula :- InChI Key :UGUBQKZSNQWWEV-UHFFFAOYSA-N
M.W : 208.21 Pubchem ID :8788
Synonyms :

Calculated chemistry of [ 103-40-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.69
TPSA : 63.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : 1.43
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 1.57
Log Po/w (SILICOS-IT) : 1.71
Consensus Log Po/w : 1.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.93
Solubility : 2.44 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (Ali) : -2.37
Solubility : 0.887 mg/ml ; 0.00426 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.434 mg/ml ; 0.00208 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 103-40-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 103-40-2 ]

* 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 [ 103-40-2 ]
  • Downstream synthetic route of [ 103-40-2 ]

[ 103-40-2 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 108-30-5 ]
  • [ 100-51-6 ]
  • [ 103-40-2 ]
YieldReaction ConditionsOperation in experiment
93.8% With dmap; triethylamine In dichloromethane at 20℃; a)
Succinic acid monobenzyl ester
To the ice-cooled solution of benzyl alcohol (12.96 g, 120 mmol) in methylene chloride (300 mL) was added triethylamine (25 mL, 180 mmol), 4-dimethylaminopyridine (610 mg, 5 mmol) followed by dropwise addition of succinic anhydride (10 g, 100 mmol).
The reaction mixture was stirred at room temperature overnight and washed with 1N HCl (2*100 mL) and brine (100 mL).
The organic layer was dried (Na2SO4) and concentrated.
The residue was dissolved in ethyl acetate (150 mL) and extracted with saturated aqueous NaHCO3 (3*150 mL).
The combined aqueous layers were acidified with concentrated HCl to pH=1-2, and extracted with methylene chloride (4*250 mL).
The combined organic layers were dried (Na2SO4) and concentrated to give the title acid (19.5 g, 93.8percent).
1H NMR (400 MHz, CDCl3) δ: 11.80-10.50 (br, 1H), 7.35 (m, 5H), 5.15 (s, 2H), 2.70 (m, 4H).
89% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; General procedure: To a solution of succinic anhydride (1.0g, 10mmol) in DMF (4mL) was added benzyl alcohol (0.94mL, 9.09mmol) and DIEA (1.93mL, 11mmol) at 0°C. The reaction mixture was stirred at room temperature overnight and was evaporated in Speed-vac. The residue was dissolved in ethyl acetate (50mL) and washed with saturated NaCl (10mL×2). The organic solution was extracted with aqueous NaHCO3 (5M, 5mL×3) and the aqueous extractions were combined, acidified to pH 4 by adding citric acid (5M), extracted with ethyl acetate (30mL×3). The EtOAc extractions were combined, washed with saturated NaCl, and dried over Na2SO4. Solvent was removed by evaporation in vacuo to give a white solid (1.66g, 89percent); 1H NMR (200MHz, CDCl3) δ 7.38 (s, 5H), 5.18 (s, 2H), 2.73–2.71 (m, 4H); LC–MS (ESI−) 207.0 (100percent).
88% With dmap In tetrahydrofuran for 18 h; Reflux A solution of succinic anhydride (1.0 g, 10 mmol), benzyl alcohol (1.14 g,11 mmol), and DMAP (54 mg, 0.44 mmol) in THF (5 mL) was refluxed for 18 h. The mixture was bacified with sat. NaHCO3, and washed with AcOEt. The aqueous layer was then acidified, and the precipiated solid was extracted with AcOEt. The solid was recrystalized to afford succinic acid monobenzyl ester as colorless needles, 1.85 g, 88percent. 1H NMR (400 MHz, CDCl3) d. 2.65–2.73 (m, 4H,CH2CH2), 5.15 (s, 2H, PhCH2), and 7.31–7.38 ppm(s, 5H, aromatic).
85% With dmap; triethylamine In dichloromethane at 20℃; for 18 h; Method B: Succinic anhydride (5 g, 50.0 mmol) was dissolved in anhydrous DCM (40 mL). Benzyl alcohol (5.69 mL, 55.0 mmol), triethylamine (7.50 mL, 55.0 mmol), and a catalytic amount of DMAP were added to this solution. The resulting clear solution was stirred at room temperature for 18h, after which the, all the volatiles were removed under vacuum. The crude residue was taken up in diethyl ether (200 mL) and was extracted with 2N NaOH (2 χ 75 mL). The aqueous extracts were carefully acidified to pH 2 with concentrated HC1 and then extracted with diethyl ether (2 χ 100 mL). The organic layer was dried (Na2S04), filtered and concentrated to give the title compound as a white solid (8.84 g, 85 percent). M.p. 52-54 °C, lit. 56-57 °C; 1H NMR (300 MHz, acetone-tfc): δ 2.68-2.71 (m, 4H, 2 χ CH2), 5.14 (s, 2H, CHiAr), 7.34-7.36 (m, 5H, ArH).
77% With pyridine; dmap In dichloromethane 3-Hydroxyflavone-3-hemisuccinate (15) was produced according to the reaction outlined in Figure 3. Reaction of succinic anhydride (11) and benzyl alcohol (12) in the presence of 4-dimethylaminopyridine (DMAP) and pyridine in dichloromethane produced the succinic acid monobenzyl esteT (13) as white crystalline flakes in 77percent yield. This protected succinic acid derivative was coupled to 3-hydroxyflavone (1) in the presence of DCC and DMAP, forming flavone-3-hemisuccinate monobenzyi ester(14) as yellow or brown oil that solidified upon standing, with yields of up to 96percent produced.The deprotection of the monobenzyl ester to form the corresponding hemisuccinate using a Pd(OAc)2 in the THF:EtOH;acetic acid solvent system, a larger scale reaction was undertaken to yield the requiτed 3-hydrosyflavone-3-hernisuccinate (15).
71% With dmap In dichloromethane at 0 - 25℃; for 96 h; Example 14; 1-(((4-(benzyloxy)-4-oxobutanoyl)oxy)methyl)-1-methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazin-1-ium iodide (Compound 14)Synthesis of 4-(benzyloxy)-4-oxobutanoic acidSuccinic anhydride (7 g, 70.0 mmol) and benzyl alcohol (8.7 mL, 83.9 mmol) were combined in dichloromethane (350 mL) at 0° C. and DMAP (0.85 g, 7.0 mmol) was added portion-wise. The reaction was allowed to gradually warm to 25° C. and stirred for 4 days. The reaction mixture was washed with 1M HCl (3.x.200 mL) then water (300 mL). The organic phases were then extracted with aq saturated NaHCO3 (3.x.300 mL). This was then acidified with conc HCl until pH 1 resulting in a solid precipitating which was filtered then dissolved in dichloromethane. The dichloromethane was dried (MgSO4) and concentrated in vacuo to give 4-(benzyloxy)-4-oxobutanoic acid (10.36 g, 71percent).1H-NMR (300 MHz, CDCl3) δ 7.41-7.29 (5H, m), 5.15 (2H, s), 2.74-2.63 (4H, m).
70.47% at 100℃; for 2 h; A mixture of 5.0 g (0.05 mol) of succinic acid anhydride, 5.4 g (0.05 mol) of benzyl alcohol, 16.25 g (0.05 mol) of cesium carbonate, and 50 ml of N,N-dimethylforamide was stirred at 100° C. for 2 hours.
The reaction mixture was cooled to room temperature, and then poured into 200 ml of ethyl acetate.
The mixture was washed with saturated aqueous NaCl containing 0.35 N HCl (3*100 mL).
The ethyl acetate phase, which contains the product, was collected and dried over anhydrous MgSO4.
The MgSO4 was removed via filtration, and the ethyl acetate was removed under reduced pressure.
The crude product was purified by crystallization in diethyl ether and hexane to provide 7.34 g of succinic acid monobenzyl ester, 70.47percent.
63.29% With dmap In tetrahydrofuran at 50℃; for 5 h; Succinic anhydride 1 (5.00 g, 49.96 mmol), benzyl alcohol (5.94 g, 54.96 mmol)And 4-dimethylaminopyridine (DMAP, 61 mg, 0.50 mmol) was added to 50 mL of tetrahydrofuran, and the mixture was heated to 50 ° C and stirred under heating for 5 hours.The solvent was removed under reduced pressure, 100 mL of ethyl acetate was added to the residue, washed with saturated sodium bicarbonate (100 mL) with,Discard the organic layer, adjust the water layer to pH=2 with dilute hydrochloric acid (1 mol/L), and filter.The filter cake was dried to obtain a white solid of 6.58 g, and the yield was 63.29percent.
57%
Stage #1: at 100℃; for 0.5 h; Microwave irradiation
Stage #2: With water In ethyl acetate at 20℃; for 2 h;
Succinic acid anhydride (0.66 g, 6.6 mmol) and benzyl alcohol (0.65 g, 6.0 mmol) were dissolved in CH2Cl2 (5 mL) and the mixture was kept under stirring in a microwave reactor (Biotage Initiator 8) at 100 °C (pressure: ca 7 bar) for 30 min. The solvent was removed under reduced pressure and the residue was taken up in EtOAc (80 mL) and water (10 mL). The mixture was stirred at rt for 2 h, washed with 5percent KHSO4 (2 * 20 mL) and brine (20 mL), and dried over Na2SO4. The solvent was removed under reduced pressure and the colorless oil was subjected to column chromatography (eluent: CH2Cl2/EtOAc 10:1 to CH2Cl2/EtOAc 2:1). The volatiles were removed from the eluate under reduced pressure, CH2Cl2 (20 mL) was added, the solvent was evaporated, and the process repeated. Product 10 was obtained as colourless oil, which crystallized during drying in vacuo to give a white compact solid (0.71 g, 57percent) mp 55-56 °C (lit.;31 mp 56-57 °C). Rf = 0.3 (CH2Cl2/EtOAc 5:1). 1H NMR (300 MHz, [D4]MeOH): δ (ppm) 2.57-2.68 (m, 4H), 5.13 (s, 2H), 7.26-7.38 (m, 5H). C11H12O4 (208.21).
57.7% With dmap In tetrahydrofuran at 50℃; for 5 h; The succinic anhydride (10g, 0.1mol), benzyl alcohol (11.88g, 0.11mol), 4- dimethylaminopyridine (DMAP) (120mg) was added to a 100ml flask, THF (50ml) as solvent, the outside temperature 50 ° C reaction 5h. The reaction solution was concentrated, ethyl acetate was added, the organic layer was successively washed with water, saturated NaHCO3 solution, saturated brine, dried over anhydrous Na2SO4, and concentrated to a solid with isopropyl ether / acetone and recrystallized to give a white solid 12g, yield 57.7percent,
48% for 4 h; Reflux Benzyl succinic acid was synthesized by following a known procedure.33 Here, succinic anhydride (30 g, 300 mmol) was dissolved in benzyl alcohol (31.6 mL, 33 g, 300 mmol), and the resulting solutionwas heated at reflux for 4 h. The reaction mixture was dissolvedin ether (100 mL), and the insoluble succinic acid wasremoved by filtration. The filtrate was extracted with saturatedaqueous Na2CO3 (3 100 mL), and the combined aqueous extractswere acidified with 2 M HCl (2.0 L). The precipitate was collectedby filtration and dried under vacuum to give 2 (30 g, 48percent). 1HNMR (CDCl3, 300 MHz) d 7.35 (m, 5H), 5.15 (s, 2H), 2.70 (m, 4H).13C NMR (CDCl3, 75 MHz) d 177.7, 172.1, 135.7, 128.8, 128.5,128.4, 66.9, 29.1, 29.0.
250 g With toluene-4-sulfonic acid In 5,5-dimethyl-1,3-cyclohexadiene for 5 h; Reflux A solution of Succinic anhydride (184 grams, 1.84 mol), Benzyl alcohol (200 grams, 1.849 mol) and PTSA (1 gram, 5.25 mmol) in Xylene (1200 ml) was stirred at reflux temperature for 5 hours. The reaction mixture was cooled to room temperature, poured onto 10percent Sodium bicarbonate solution (2500 ml), aqueous layer washed with Ethyl acetate (500 ml), pH made acidic with dil HCl, extracted with Chloroform, dried over Sodium sulphate, distilled under reduced pressure, precipitated the residue by using Hexane to give pure Succinic acid mono benzyl ester (250 grams) as white powder with a melting point of 61-63° C. The product was characterized by IH NMR (CDCl3) δ 2.70 (m, 4H, CH2X2), 5.20 (s, 2H, CH2), 7.35 (m, 5H, Ar), 10.25 (bs, 1H, COOH).
18.5 g With pyridine In tetrahydrofuran at 20℃; for 120 h; 10.0 g (100 mmol) of succinic anhydride, 10 ml of THF (tetrahydrofuran), 10.8 g (100 mmol) of benzyl alcohol and 4 ml of pyridine were combined and stirred for 5 days at ambient temperature. The solution was diluted with toluene. The mixture was extracted with a saturated solution of sodium hydrogen carbonate. The water phase was separated, and acidified with hydrochloric acid. The product was extracted with toluene to yield 18.5 g of succinic acid monobenzyl ester.

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  • 2
  • [ 15026-16-1 ]
  • [ 103-40-2 ]
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  • 3
  • [ 110-15-6 ]
  • [ 104-57-4 ]
  • [ 103-40-2 ]
Reference: [1] Patent: US2016/169864, 2016, A1, . Location in patent: Paragraph 0493
  • 4
  • [ 108-30-5 ]
  • [ 121-44-8 ]
  • [ 103-40-2 ]
YieldReaction ConditionsOperation in experiment
83% With hydrogenchloride; benzyl alcohol In tetrahydrofuran; ethyl acetate Butanedioic acid monobenzylester 21
To a solution of 4.13 mL (4.32 g, 40 mmol) of benzyl alcohol and 4.40 g (44 mmol) of succinic anhydride in 100 mL of THF at 0° C. was added at once 12.24 mL (8.90 g, 88 mmol) of Et3 N.
The mixture was allowed to come to room temperature and stirred for 18 h at which time it was concentrated under vacuum to a viscous oil and partitioned between 100 mL of 1 N HCl and 100 mL of EtOAc.
The EtOAc layer was extracted with 84 mL of 5percent NaHCO3 solution.
The aqueous layer was acidified with concentrated HCl solution to pH 1 and extracted with two 50 mL portions of EtOAc.
The EtOAc layers were combined and washed with brine, dried (Mg SO4), filtered, and concentrated to give 6.9 g (83percent) of 21 as a white chunky solid: 1 H NMR (CDCl3) 2.70 (s, 4H), 5.22 (s, 2H), 7.38 (s, 5H).
83% With hydrogenchloride; benzyl alcohol In tetrahydrofuran; ethyl acetate Butanedioic acid monobenzylester 21
To a solution of 4.13 mL (4.32 g, 40 mmol) of benzyl alcohol and 4.40 g (44 mmol) of succinic anhydride in 100 mL of THF at 0° C. was added at once 12.24 mL (8.90 g, 88 mmol) of Et3 N.
The mixture was allowed to come to room temperature and stirred for 18 h at which time it was concentrated under vacuum to a viscous oil and partitioned between 100 mL of 1N HCl and 100 mL of EtOAc.
The EtOAc layer was extracted with 84 mL of 5percent NaHCO3 solution.
The aqueous layer was acidified with concentrated HCl solution to pH 1 and extracted with two 50 mL portions of EtOAc.
The EtOAc layers were combined and washed with brine, dried (Mg SO4), filtered, and concentrated to give 6.9 g (83percent) of 21 as a white chunky solid: 1 H NMR (CDCl3) 2.70
(s, 4H), 5.22 (s, 2H), 7.38 (s, 5H).
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[2] Patent: US5112953, 1992, A,
  • 5
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  • [ 103-40-2 ]
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  • 7
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  • 9
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  • 13
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  • 16
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