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[ CAS No. 26825-95-6 ] {[proInfo.proName]}

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Chemical Structure| 26825-95-6
Chemical Structure| 26825-95-6
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Product Details of [ 26825-95-6 ]

CAS No. :26825-95-6 MDL No. :MFCD01838179
Formula : C13H25BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QNXOHINFQALBQN-UHFFFAOYSA-N
M.W : 293.24 Pubchem ID :11022721
Synonyms :

Calculated chemistry of [ 26825-95-6 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 12
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 73.76
TPSA : 26.3 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) : -4.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.98
Log Po/w (XLOGP3) : 5.35
Log Po/w (WLOGP) : 4.46
Log Po/w (MLOGP) : 3.82
Log Po/w (SILICOS-IT) : 4.69
Consensus Log Po/w : 4.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.24
Solubility : 0.017 mg/ml ; 0.000058 mol/l
Class : Moderately soluble
Log S (Ali) : -5.66
Solubility : 0.000649 mg/ml ; 0.00000221 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.25
Solubility : 0.00164 mg/ml ; 0.00000558 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.85

Safety of [ 26825-95-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 26825-95-6 ]

* 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 [ 26825-95-6 ]
  • Downstream synthetic route of [ 26825-95-6 ]

[ 26825-95-6 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 67-56-1 ]
  • [ 73367-80-3 ]
  • [ 26825-95-6 ]
YieldReaction ConditionsOperation in experiment
93% for 15 h; Inert atmosphere; Reflux Methyl 12-bromododecanoate (7) was synthesized via a standard procedure by dissolving 12-bromododecanoic acid (6) (1.0 g, 3.59 mmol) in dry MeOH (10 ml) containing concentrated H2SO4 (200 μl) under argon atmosphere and heating to reflux for 15 h.
MeOH was removed under reduced pressure, the residual was diluted with EtOAc (100 ml), washed with a saturated NaHCO3 solution (3 * 20 ml) and brine (2 * 20 ml), and dried with MgSO4.
The solvent was removed under reduced pressure.
Chromatography on silica gel with PE/EtOAc (97.5:2.5) provided the desired ester 7 (974 mg, 3.32 mmol, 93percent) as a colorless oil.
The analytical data were generally consistent with those reported previously [52–54]. TLC: Rf 0.45 (PE/EtOAc, 9:1); IR (ATR, film): 2926, 2854, 1740 (C=O), 1459, 1436, 1362, 1252, 1242, 1197, 1171, 1120, 1103, 1012, 881, 723 cm-1; 1H NMR (CDCl3): δ = 1.23-1.35 (m, 12 H, 4-H to 9-H), 1.42 (tt, J = 7.4, 7.2 Hz, 2 H, 10-H), 1.62 (tt, J = 7.6, 7.4 Hz, 2 H, 3-H), 1.85 (tt, J = 7.4, 6.9 Hz, 2 H, 11-H), 2.30 (t, J = 7.6 Hz, 2 H, 2-H), 3.41 (t, J = 6.9 Hz, 2 H, 12-H), 3.67 (s, 3 H, OCH3) ppm; 13C NMR (CDCl3): δ = 25.1 (C-3), 28.3 (C-10), 28.9, 29.3, 29.4, 29.5, 29.5, 29.6 (C-4-C-9), 33.0 (C-11), 34.2 (C-12), 34.3 (C-2), 51.6 (OCH3), 174.5 (C-1) ppm; HRMS (ESI): calcd. for [C13H26O279Br/81Br]+ ([M+H]+): 293.11107/295.10902; found: 293.11113/295.10908.
92% With sulfuric acid In tetrahydrofuran at 65℃; for 2 h; To a solution of 12-bromododecanoic acid (2.5 g, 8.95 mmol) in THF (7 mL) was added methanol (7.2 mL, 179 mmol). Sulfuric acid (0.50 mL, 8.95 mmol) was added dropwise and the reaction was allowed to stir at 65 °C for two hours. The reaction mixture was washed with 5percent NaHCC and brine. The organic layer was dried over anhydrous Na2SC>4, filtered, and concentrated in vacuo. Purification by silica gel chromatography (0-20percent EtOAc/hexanes) provided methyl 12-bromododecanoate (2.40 g, 92percent).
lH NMR (300 MHz, CDC13) δ: ppm 3.69 (s, 3H); 3.44 (t, 2H); 2.33 (t, 2H); 1.88 (br. m, 2H); 1.64 (br. m, 2H); 1.45 (br. m, 2H); 1.31 (br. m, 12H).
92% With sulfuric acid In tetrahydrofuran at 65℃; for 2 h; Step 1 : Methyl 12-bromododecanoate Chemical Formula: Ci3H25Br02 Molecular Weight: 293.25 [00618] To a solution of 12-bromododecanoic acid (2.5 g, 8.95 mmol) in THF (7 mL) was added methanol (7.2 mL, 179 mmol). Sulfuric acid (0.50 mL, 8.95 mmol) was added dropwise and the reaction was allowed to stir at 65 °C for two hours. The reaction mixture was washed with 5percent NaHCCb and brine. The organic layer was dried over anhydrous Na2SC>4, filtered, and concentrated in vacuo. Purification by ISCO silica flash chromatography (0-20percent EtOAc/hexanes) provided methyl 12-bromododecanoate (2.40 g, 92percent). Ti-NMR (300 MHz, CDCI3) δ: ppm 3.69 (s, 3H); 3.44 (t, 2H); 2.33 (t, 2H); 1.88 (br. m, 2H); 1.64 (br. m, 2H); 1.45 (br. m, 2H); 1.31 (br. m, 12H).
92% With sulfuric acid In tetrahydrofuran at 65℃; for 2 h; Nonyl 8-((2-hydroxyethyl)((9Z,12Z)-octadeca-9,12-dien-l- yl)amino)octanoate [00165] To a solution of 12-bromododecanoic acid (2.5 g, 8.95 mmol) in THF (7 mL) was added methanol (7.2 mL, 179 mmol). Sulfuric acid (0.50 mL, 8.95 mmol) was added dropwise and the reaction was allowed to stir at 65 °C for two hours. The reaction mixture was washed with 5percent NaHCCb and brine. The organic layer was dried over anhydrous Na2S04, filtered, and concentrated in vacuo. Purification by silica gel chromatography (0-20percent EtOAc/hexanes) provided methyl 12-bromododecanoate (2.40 g, 92percent). [00166] NMR (300 MHz, CDCb) δ: ppm 3.69 (s, 3H); 3.44 (t, 2H); 2.33 (t, 2H); 1.88 (br. m, 2H); 1.64 (br. m, 2H); 1.45 (br. m, 2H); 1.31 (br. m, 12H).

Reference: [1] Journal of Antibiotics, 1995, vol. 48, # 12, p. 1467 - 1480
[2] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 6, p. 1393 - 1400
[3] Analytical Biochemistry, 2014, vol. 456, # 1, p. 70 - 81
[4] Patent: WO2017/49245, 2017, A2, . Location in patent: Paragraph 00539-00540
[5] Patent: WO2017/112865, 2017, A1, . Location in patent: Paragraph 00618
[6] Patent: WO2018/170306, 2018, A1, . Location in patent: Paragraph 00165-00166
[7] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 242, p. 2647[8] Bulletin de la Societe Chimique de France, 1957, p. 1463,1469
  • 2
  • [ 558-13-4 ]
  • [ 71655-36-2 ]
  • [ 26825-95-6 ]
YieldReaction ConditionsOperation in experiment
90% With triphenylphosphine In toluene (1)
Methyl 12-hydroxydodecanoate (2.30 g, 10.0 mmol), triphenylphosphine (3.93 g, 1.5 eq), carbon tetrabromide (4.97 g, 1.5 eq) were stirred in toluene (10 ml) at room temperature for 3 hr.
The reaction solution was filtered, followed by concentration to dryness.
The residue was purified by column chromatography on silica gel (toluene-ethyl acetate (99: 1)) to give 2.65 g (90percent) of methyl 12-bromododecanoate.
1H-NMR (CDCl3) δ: 1.20-1.35 (12H, m), 1.39-1.43 (2H, m), 1.56-1.63 (2H, m), 1.82-1.88 (2H, m), 2.30 (2H, t, J = 7.6 Hz), 3.41 (2H, t, J = 7.6 Hz), 3.73 (3H, s)
IR (KBr): 1742 cm-1EI-MS m/z: 293 (M+)
Reference: [1] Patent: EP953357, 1999, A1,
  • 3
  • [ 71655-36-2 ]
  • [ 26825-95-6 ]
Reference: [1] Journal of Pharmacology and Experimental Therapeutics, 1999, vol. 288, # 1, p. 57 - 64
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 7, p. 1369 - 1372
  • 4
  • [ 87521-75-3 ]
  • [ 26825-95-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 7, p. 1369 - 1372
  • 5
  • [ 947-05-7 ]
  • [ 26825-95-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 7, p. 1369 - 1372
  • 6
  • [ 505-95-3 ]
  • [ 26825-95-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 7, p. 1369 - 1372
  • 7
  • [ 186581-53-3 ]
  • [ 73367-80-3 ]
  • [ 26825-95-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1988, # 6, p. 989 - 994
[2] Journal of Organometallic Chemistry, 1983, vol. 253, # 1, p. 31 - 38
[3] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539
  • 8
  • [ 5675-51-4 ]
  • [ 26825-95-6 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539
  • 9
  • [ 76999-24-1 ]
  • [ 26825-95-6 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 242, p. 2647[2] Bulletin de la Societe Chimique de France, 1957, p. 1463,1469
  • 10
  • [ 67-56-1 ]
  • [ 505-95-3 ]
  • [ 26825-95-6 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 2680
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