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[ CAS No. 5675-51-4 ] {[proInfo.proName]}

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Chemical Structure| 5675-51-4
Chemical Structure| 5675-51-4
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Product Details of [ 5675-51-4 ]

CAS No. :5675-51-4 MDL No. :MFCD00004755
Formula : C12H26O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GHLKSLMMWAKNBM-UHFFFAOYSA-N
M.W : 202.33 Pubchem ID :79758
Synonyms :

Calculated chemistry of [ 5675-51-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 11
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 62.12
TPSA : 40.46 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) : -4.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.06
Log Po/w (XLOGP3) : 4.06
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 2.49
Log Po/w (SILICOS-IT) : 3.35
Consensus Log Po/w : 3.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.24 mg/ml ; 0.00119 mol/l
Class : Soluble
Log S (Ali) : -4.61
Solubility : 0.00492 mg/ml ; 0.0000243 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.59
Solubility : 0.0516 mg/ml ; 0.000255 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 1.89

Safety of [ 5675-51-4 ]

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 [ 5675-51-4 ]

* 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 [ 5675-51-4 ]
  • Downstream synthetic route of [ 5675-51-4 ]

[ 5675-51-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 5675-51-4 ]
  • [ 3344-77-2 ]
YieldReaction ConditionsOperation in experiment
87% With hydrogen bromide In water; toluene for 48 h; Inert atmosphere; Reflux To a solution of diol 7 (28 g, 0.14 mol) in toluene (600 mL) was added concentrated HBr [27.5 mL of a 48percent (9 M) aqueous solution, 0.162 mol]. The heterogeneous mixture was heated at reflux for 36 h, after which TLC analysis showed that 20percent of the diol still remained. Thus, a further quantity of HBr (10 mL, 0.09 mol) was added, and the mixture was heated at reflux for a further 12 h, after which TLC analysis showed no diol remaining. The reaction mixture was allowed to return to room temperature, and the phases were separated. The organic layer was diluted with ether (200 mL) and washed with 1 M NaOH solution (200 mL) and brine solution (300 mL). Drying over anhydrous Na2SO4, filtration and concentration of the organic layer gave a yellow oil, which was purified by column chromatography using hexane/ether as eluent (7:3) to provide 8 as a pale yellow oil (32.0 g, 87percent). 1H NMR (300 MHz, CDCl3): δ 3.64 (t, J = 6.6 Hz, 2H), 3.40 (t, J = 7.0 Hz, 2H), 1.89-1.80 (m, 2H), 1.61-1.51 (m, 2H), 1.44-1.27 (m, 16H); 13C NMR (75 MHz, CDCl3): δ 62.8, 33.9, 32.7, 32.6, 29.5, 29.4, 29.3, 28.7, 28.1, 25.6; IR (neat): 3358, 2923, 2362,1740,1515,1052 cm-1; ESI-MS: m/z 365 (M+H)+.
85% With hydrogen bromide In cyclohexane; water for 6 h; Reflux Example 1
Preparation of 12-bromododecan-1-ol (3)
48percent HBr in water (77 ml; 0.46 mol; 15 eq.) is added to a solution of 1,12-dodecan-ol (6.15 g; 30.4 mmol; 1 eq.) in cyclohexane (140 ml).
The heterogeneous mixture is heated under reflux.
After 6 h, the aqueous phase is extracted with ether (3*100 ml).
The organic phases are combined, washed with a saturated solution of Na2CO3, dried on MgSO4, filtered and evaporated.
The crude reaction product is purified by silica gel chromatography (eluent: hexane-AcOEt: 6-4) to yield 7.06 g of a white solid.
Yield: 85percent
Empirical formula: C12H25BrO
85% With hydrogen bromide In water; toluene for 48 h; Reflux To a solution of 1,12-dodecanediol (1.00 g, 4.94 mmol) in toluene (20 mL) was added aqueous HBr (48percent, 0.67 mL, 5.33 mmol) and the resulting mixture was refluxed until the diol was completely consumed by TLC monitoring (48 h). The mixture was cooled to room temperature and quenched with 1M NaOH. The resulting mixture was extracted with EtOAc. The combined organic layer was washed with H2O and brine, dried over MgSO4, and evaporated. The resulting residue was purified by column chromatography (SiO2, hexane/EtOAc 3:1) to furnish S1 (1.11 g, 85percent) as a pale yellow oil
78% With hydrogen bromide In water; toluene for 3 h; Reflux To a stirred solution of dodecane-1,12-diol (8.365 g, 42.75 mmol), 48percent HBr in water (9.7 ml, 85.50 mmol) and toluene (120 ml) were added and the reaction mixture refluxed for 3 h.
The reaction mixture was then concentrated, the crude compound was dissolved in DCM (150 ml), washed with water, NaHCO3 brine solution, dried over MgSO4 and concentrated.
The crude product was purified by silica gel column (5percent EtOAc in hexane) to obtain 12-bromododecan-1-ol as an off-white low melting solid (8.87 g, 78percent).
Rf=0.55 (10percent EtOAc in Hexane, KMnO4 active.).
1H NMR (300 MHz, CDCl3) δ 3.63 (t, 2H), 3.40 (t, 2H), 3.85 (m, 2H), 1.59-1.51 (m, 2H), 1.44-1.27 (m, 16H); 13C NMR (75 MHz, CDCl3) δ 62.91, 34.00, 32.82, 32.74, 29.56, 29.50, 29.41, 29.22, 28.74, 28.15, 25.73; MS (EI) m/z 220 (3.6percent), 164 (8.7percent), 162 (8.1percent), 150 (13.7percent), 148 (13.6percent), 97 (31.9percent), 83 (45.4percent), 82 (58.7percent), 69 (66.7percent), 68 (54.2percent), 55 (100percent), 41 (57.9percent); HRMS Calculated: 264.1089. Found: [M-18]+=246.09741.
73% With hydrogen bromide In cyclohexane; water for 6 h; Heating / reflux Synthesis Example B-(10) 1,10-Dodecanediol (2 g) was dissolved in 25 ml of cyclohexane, and 57percent hydrobromic acid solution (25 ml) was added to this solution. The reaction mixture was refluxed for six hours while stirring. After the reaction, the mixture was extracted three times with diethyl ether. The organic layer was neutralized with saturated sodium hydrogen carbonate solution, washed with saline solution, dried over magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel flash chromatography (hexane: ethyl acetate = 7:3) gave 12-bromododecan-1-ol as white crystals at a 73percent yield. Molecular weight: 265.23 (C12H25BrO) TLC: (hexane-ethyl acetate 7-3) Rf value=0.53 1H-NMR: (300MHz, CDCl3) δ:1.26 (s large, 16H, -(CH2)6-); 1.56 (qt, 2H, J=6.9Hz, -CH2-); 1.85 (qt, 2H, J=7.1Hz, -CH2-); 3.40 (t, 2H, J=7.1Hz, -CH2-Br); 3.64 (t, 2H, J=6.6Hz, -CH2-O-) 13C-NMR: (75MHz; CDCl3)δ: 25.72; 27.28; 28.16; 28.74; 29.40; 29.49; 29.55; 30.92; 32.79; 32.82; 34.05; 63.08
65% With hydrogen bromide In toluene at 110℃; for 24 h; General procedure: To a stirred solution of 1,6-hexanodiol 1a (1.00 equiv.), 1,9-nonanediol 1b (1.00 equiv.), or 1,12-dodecanediol 1c (1.00 equiv.), in 30 mL of toluene was added HBr 48 percent (2.00 equiv.). The reaction was stirred at 110 °C for 24 h. The solvent was removed under reduced pressure, and the residue was purified by column chromatography over silica gel, eluting with hexane/EtOAc 9:1, to yield pure haloalcohol 2a–c. These compounds were transformed into their corresponding azido alcohols 3a–c by SN2 substitution (Scheme 1). A stock solution of 0.5 M NaN3 in DMSO was prepared by stirring the solution for 24 h at room temperature. To a 100-mL round-bottom flask equipped with a magnetic stir bar was added a 0.5 M solution of NaN3 in DMSO at room temperature. To this solution was added the bromo alcohol 2a (1.00 equiv.), 2b (1.00 equiv.), or 2c (1.00 equiv.), and the mixture was stirred for 24 h at room temperature.The reaction was quenched with H2O (50 mL) and stirred until it cooled to room temperature. The mixture was extracted with Et2O (3 9 30 mL), and the resulting extracts were washed with H2O (3 x 50 mL) and brine (50 mL). The organic layer was dried (Na2SO4) and filtered, and the residue obtained was purified by column chromatography over silica gel, eluting with hexane/EtOAc 9:1, to yield pure alkyl azido alcohols 3a–c. A solution of the azido alcohol 3a (1.00 equiv.), 3b (1.00 equiv.), or 3c (1.00 equiv.) in CH2Cl2 (50 mL) was cooled to 0 °C. Et3N (2.00 equiv.) and methanesulfonyl chloride (2.00 equiv.) was added. The reaction mixture was stirred for 24 h and then allowed to reach room temperature. The reaction mixture was poured into crushed ice (70 mL) and was then extracted with methylene chloride (3 9 30 mL). The organic layer was dried (Na2SO4), filtered, and evaporated under reduced pressure. The residue obtained was purified by column chromatography over silica gel, eluting with hexane/EtOAc 9:1, to yield highly purified halo alcohol pure methanesulfonate alkyl azides compounds 4a, 4b, and 4d.

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  • [ 5675-51-4 ]
  • [ 3344-70-5 ]
  • [ 3344-77-2 ]
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[2] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5837 - 5838
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  • [ 5675-51-4 ]
  • [ 26825-95-6 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539
  • 4
  • [ 830-13-7 ]
  • [ 505-95-3 ]
  • [ 5675-51-4 ]
  • [ 3903-40-0 ]
Reference: [1] Patent: WO2013/116029, 2013, A1, . Location in patent: Paragraph 00131
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