Home Cart 0 Sign in  
X

[ CAS No. 53463-68-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 53463-68-6
Chemical Structure| 53463-68-6
Chemical Structure| 53463-68-6
Structure of 53463-68-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 53463-68-6 ]

Related Doc. of [ 53463-68-6 ]

Alternatived Products of [ 53463-68-6 ]

Product Details of [ 53463-68-6 ]

CAS No. :53463-68-6 MDL No. :MFCD00041681
Formula : C10H21BrO Boiling Point : -
Linear Structure Formula :- InChI Key :LGZMUUBPTDRQQM-UHFFFAOYSA-N
M.W : 237.18 Pubchem ID :104507
Synonyms :

Calculated chemistry of [ 53463-68-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 9
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.22
TPSA : 20.23 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) : -4.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.16
Log Po/w (XLOGP3) : 4.38
Log Po/w (WLOGP) : 3.49
Log Po/w (MLOGP) : 3.27
Log Po/w (SILICOS-IT) : 3.63
Consensus Log Po/w : 3.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.48
Solubility : 0.0793 mg/ml ; 0.000334 mol/l
Class : Soluble
Log S (Ali) : -4.52
Solubility : 0.00714 mg/ml ; 0.0000301 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.21
Solubility : 0.0146 mg/ml ; 0.0000614 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 2.97

Safety of [ 53463-68-6 ]

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 [ 53463-68-6 ]

* 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 [ 53463-68-6 ]
  • Downstream synthetic route of [ 53463-68-6 ]

[ 53463-68-6 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 112-47-0 ]
  • [ 53463-68-6 ]
  • [ 4101-68-2 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 27, p. 7735 - 7748
[2] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5837 - 5838
[3] Tetrahedron, 2009, vol. 65, # 20, p. 3961 - 3966
[4] Tetrahedron, 2004, vol. 60, # 24, p. 5237 - 5252
[5] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1215 - 1220
[6] Organic Process Research and Development, 2011, vol. 15, # 3, p. 673 - 680
[7] Helvetica Chimica Acta, 1926, vol. 9, p. 226
[8] Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632
  • 2
  • [ 629-04-9 ]
  • [ 53463-68-6 ]
  • [ 1454-85-9 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 20, p. 4851 - 4862
  • 3
  • [ 112-47-0 ]
  • [ 53463-68-6 ]
YieldReaction ConditionsOperation in experiment
93% With hydrogen bromide In water; toluene for 16 h; Inert atmosphere; Reflux; Dean-Stark 1,10-Decanediol 15 (10 g, 57.47 mmol) in toluene (600 mL) was taken in a 1 L two-neck round bottom flask equipped with a Dean Stark apparatus, to which HBr (48percent, 7.15 mL, 63.21 mmol) was added and refluxed for 16 h. After cooling, the reaction mixture was washed with 1 N HCl, 2 M aq NaOH, H2O, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (15percent EtOAc/hexanes) to give bromo-alcohol as a clear oil (12.7 g, 93percent). Rf=0.45 (20percent EtOAc/hexanes); 1H NMR (500 MHz, CDCl3): δ 3.63 (t, J=5.8 Hz, 2H), 3.39 (t, J=6.8 Hz, 2H), 1.85 (m, 2H), 1.56 (m, 2H), 1.42 (m, 2H), 1.38–1.27 (m, 10H); 13C NMR (125 MHz, CDCl3): δ 62.9, 33.9, 32.7, 32.6, 29.3, 29.2, 29.2, 28.6, 28.0, 25.6; IR (neat): νmax 2927, 2856, 1738, 1593, 1449, 1367, 1241 cm−1; HRMS (ESI) calcd for C10H22BrO [M+H]+ 237.0854, found 237.0845.
92% With hydrogen bromide In toluene at 180℃; for 24 h; To a solution of 1,10-decandiol (3) (34.8 g, 0.2 mol, 1 equiv) in toluene (400 mL) was added 48percent HBr (22.6 mL, 0.2 mol, 1 equiv) dropwise with stirring and refluxed at 180 °C using Dean-Stark trap for 24 h. The mixture was cooled to room temperature and washed with 6 N NaOH (150 mL), 10percent HCl (150 mL), H2O (2 x 250 mL) and brine (200 mL). The organic layer was dried over Na2SO4, concentrated and chromatographed on silica gel eluting with cyclohexane/ethylacetate (4:1) to give 43.5 g (92percent) of 10-bromo-1-decanol as a colourless liquid. 1H NMR δ 3.65 (t, J = 6.7 Hz, 2H, H-1), 3.43 (t, J = 7.0 Hz, 2H, H-10), 1.87 (m, 2H, H-9), 1.57 (m, 2H, H-2), 1.43 (m, 2H, H-3), 1.26-1.41 (m, 10H, H-4-8). 13C NMR δ 63.0 (C1), 34.1 (C10), 32.8, 32.6, 29.5, 29.4, 29.3, 28.6, 28.2, 25.6.To a solution of 10-bromo-1-decanol (41 g, 0.17 mol, 1 equiv) in 130 mL of acetone at -5 °C was added slowly chromic acid solution prepared from CrO3 (25.7 g, 0.26 mol, 1.5 equiv), water (25 mL) and conc H2SO4 (22.5 mL, 0.34 mol, 2 equiv) at 0 °C, then stirred for 2 h and left over night at room temperature. The mixture was extracted with diethyl ether (3 x 250 mL), washed with water (250 mL) and brine (250 mL), dried over Na2SO4 and concentrated. The residue was chromatographed on silica gel eluting with CH2Cl2 afforded 31.0 g of 10-bromodecanoic acid (4d) (73percent) as a white solid after recrystallization from petroleum ether.
90% With hydrogen bromide In water; toluene for 72 h; Heating / reflux EXAMPLE 1
To a mixture of 1,10-decanediol (35.73g, 0.205 mol) and toluene (700 mL) was added concentrated HBr (29 mL of 47percent aqueous solution, 0.24 mol).
The heterogeneous mixture was stirred and heated at reflux for 36 hours. TLC analysis indicated substantial amounts of 1,10-decanediol still remained.
Thus a further quantity of HBr (15 mL, 0.12 mol) was added and the mixture was heated at reflux for further 36 h, at which time TLC analysis showed no diol remaining.
The reaction mixture was allowed to cool to room temperature and the phases were separated.
The organic layer was concentrated by evaporating the toluene and diluted with ethyl acetate and washed with water, sodium bicarbonate and brine.
Then the organic layer was dried over Na2SO4 and concentrated to yellow liquid and purification of this crude reaction mixture by column chromatography provided pure 10-bromodecanol (43.0 g) in 90percent yield.
90% With hydrogen bromide In water; toluene for 72 h; Heating / reflux EXAMPLE 1
To a mixture of 1,10-decanediol (35.73g, 0.205 mol) and toluene (700 mL) was added concentrated HBr (29 mL of 47percent aqueous solution, 0.24 mol).
The heterogeneous mixture was stirred and heated at reflux for 36 hours. TLC analysis indicated substantial amounts of 1,10-decanediol still remained.
Thus a further quantity of HBr (15 mL, 0.12 mol) was added and the mixture was heated at reflux for further 36 h, at which time TLC analysis showed no diol remaining.
The reaction mixture was allowed to cool to room temperature and the phases were separated.
The organic layer was concentrated by evaporating the toluene and diluted with ethyl acetate and washed with water, sodium bicarbonate and brine.
Then the organic layer was dried over Na2SO4 and concentrated to yellow liquid and purification of this crude reaction mixture by column chromatography provided pure 10-bromodecanol (43.0 g) in 90percent yield.
89% With hydrogen bromide In cyclohexane; water for 6 h; Heating / reflux Synthesis Example A-(1) 1,10-Decanediol (4 g) was dissolved in 100 ml of cyclohexane, and 57percent aqueous hydrobromic acid solution (58 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 10-bromodecan-1-ol as white crystals at an 89percent yield. Molecular weight: 237.18 (C10H21BrO) TLC: (hexane-ethyl acetate=7-3) Rf value: 0.53 1H-NMR: (300MHz, CDCl3)δ: 1.26 (s large, 12H, -(CH2)6-); 1.56 (qt, 2H, J=7.0Hz, -CH2-); 1.85 (qt, 2H, J=7.1Hz, -CH2-); 3.40 (t, 2H, J=6.9Hz, -CH2-Br); 3.64 (t, 2H, J=6.6Hz, -CH2-O-) 13C-NMR: (75MHz, CDCl3) δ: 25.70; 28.14-29.45; 32.77; 32.80; 34.03; 63.05
80% With hydrogen bromide; tetra-(n-butyl)ammonium iodide In water for 0.0833333 h; Microwave irradiation A mixture of 1, 10-decanediol (0.3 g, 1.72mmol), 48percent aq. hydrogen bromide (0.29 g, 3.58 mmol) and tetrabutylammonium iodide (0.12 g, 0.34 mmol) was subjected to MWI at 355 W for 5 min. The reaction mixture was cooled, extracted with diethyl ether (3x10 mL) and washed with saturated sodium bicarbonate solution (2 x 5 mL), 10percent aq. sodium thiosulfate (2 x 5 mL), water (2 x5 mL), and brine and dried. The evaporation of solvent under reduced pressure furnished the crude product, which was purified by column chromatography over silica gel using 5percent ethyl acetate in n-hexane to afford pure product (3, 0.32 g, 80percent) as a colourless oil.
73% With hydrogen bromide In water; toluene for 16 h; Reflux HBr (48percent in H2O, w/w, 16.3 mL, 138 mmol) was added to a mixture ofdecane-1,10-diol (2; 20 g, 115 mmol) and toluene (250 mL). The resultingmixture was stirred at reflux temperature for 16 h. Afterreaching r.t. and careful addition of sat. aq Na2S2O3 (50 mL), the aqueouslayer was extracted with EtOAc (3 × 200 mL). The combined extractswere dried (MgSO4), filtered, and the solvent was evaporated.Purification of the residue by flash chromatography (silica gel, hexanes/EtOAc, 4:1 to 2:1) afforded the title compound as a colorless oil(19.8 g, 73percent).IR (ATR): 3328, 2924, 2853, 1463, 1437, 1371, 1352, 1256, 1242, 1129,1055, 899, 756, 722, 644, 562, 505, 465, 445, 428, 417 cm–1.1H NMR (400 MHz, CDCl3): δ = 3.63 (t, J = 6.6 Hz, 2 H), 3.40 (t, J = 6.9Hz, 2 H), 1.88–1.80 (m, 2 H), 1.60–1.51 (m, 2 H), 1.46–1.24 (m, 13 H).13C NMR (100 MHz, CDCl3): δ = 63.2, 34.2, 32.92, 32.89, 29.6, 29.49,29.48, 28.9, 28.3, 25.8.HRMS-ESI: m/z calcd for [C10H21BrO + Na]+: 259.0669; found:259.0668.
59% With hydrogen bromide In toluene at 20℃; for 18 h; adding toluene 500 ml in a 1 L three-necked flask, 1 175g of 10-decanediol, adding 200ml of 40percent hydrobromic acid, stirring at room temperature for 18h, separating the liquid, washing the toluene phase with 200ml saturated laboratory, drying, concentrated crude product 240g,Column chromatography (EA: PE = 4:1) gave 140 g of 10-bromofurfuryl alcohol in a yield of 59percent

Reference: [1] Tetrahedron, 2015, vol. 71, # 7, p. 1058 - 1067
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1083 - 1092
[3] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 6, p. 273 - 276
[4] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[5] Patent: EP1818336, 2007, A1, . Location in patent: Page/Page column 7
[6] Patent: US2007/191606, 2007, A1, . Location in patent: Page/Page column 4-5
[7] European Journal of Organic Chemistry, 2006, # 5, p. 1285 - 1295
[8] Patent: EP1854777, 2007, A1, . Location in patent: Page/Page column 12
[9] Patent: EP1102775, 2005, B1, . Location in patent: Page/Page column 10
[10] Tetrahedron, 1992, vol. 48, # 16, p. 3413 - 3428
[11] Chemical Research in Toxicology, 2012, vol. 25, # 10, p. 2253 - 2260
[12] Tetrahedron Letters, 2010, vol. 51, # 52, p. 6906 - 6910
[13] Polish Journal of Chemistry, 2004, vol. 78, # 7, p. 937 - 942
[14] Organic Letters, 2015, vol. 17, # 21, p. 5248 - 5251
[15] Journal of Organic Chemistry, 2001, vol. 66, # 14, p. 4766 - 4770
[16] Synthesis, 1985, # 12, p. 1161 - 1162
[17] Canadian Journal of Chemistry, 1995, vol. 73, # 12, p. 2224 - 2232
[18] Tetrahedron Letters, 1999, vol. 40, # 2, p. 337 - 340
[19] Organic Process Research and Development, 2003, vol. 7, # 3, p. 339 - 340
[20] Journal of Chemical Research, 2015, vol. 39, # 4, p. 230 - 232
[21] Organic Letters, 2015, vol. 17, # 3, p. 434 - 437
[22] Journal of Organic Chemistry, 1986, vol. 51, # 2, p. 260 - 263
[23] Gazzetta Chimica Italiana, 1982, vol. 112, # 5/6, p. 231 - 234
[24] Journal of Porphyrins and Phthalocyanines, 2013, vol. 17, # 11, p. 1080 - 1093
[25] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1233 - 1239
[26] Polymer, 2012, vol. 53, # 2, p. 359 - 369
[27] Nature Chemistry, 2017, vol. 9, # 3, p. 264 - 272
[28] Synthesis (Germany), 2017, vol. 49, # 1, p. 202 - 208
[29] Chemistry Letters, 1981, p. 703 - 706
[30] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 1216 - 1219
[31] Journal of Organic Chemistry, 1980, vol. 45, # 20, p. 3952 - 3957
[32] Patent: US5378718, 1995, A,
[33] Chemistry Letters, 1994, # 10, p. 1789 - 1792
[34] Journal of Organometallic Chemistry, 2013, vol. 730, p. 49 - 56
[35] Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1427 - 1445
[36] Journal of Chemical Ecology, 2007, vol. 33, # 3, p. 555 - 565
[37] Patent: CN108383688, 2018, A, . Location in patent: Paragraph 0014
[38] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 371 - 378
[39] Synthetic Communications, 2013, vol. 43, # 21, p. 2846 - 2852
[40] Synthesis, 1994, # SPEC. ISS., p. 1257 - 1261
[41] Tetrahedron Letters, 1989, vol. 30, # 15, p. 1991 - 1992
[42] Journal of the American Chemical Society, 1956, vol. 78, p. 2255,2256[43] Journal of Organic Chemistry, 1956, vol. 21, p. 883,885
[44] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 728 - 732
[45] Tetrahedron Letters, 1993, vol. 34, # 22, p. 3589 - 3592
[46] Agricultural and Biological Chemistry, 1988, vol. 52, # 10, p. 2459 - 2468
[47] Chemistry of Natural Compounds, 1996, vol. 32, # 3, p. 381 - 383
[48] Chemical Physics Letters, 1997, vol. 264, # 3-4, p. 376 - 380
[49] Journal of Agricultural and Food Chemistry, 2005, vol. 53, # 10, p. 3872 - 3876
[50] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2637 - 2640
[51] Synthesis, 2005, # 18, p. 3051 - 3058
[52] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 3917 - 3920
[53] Patent: US4675335, 1987, A,
[54] Patent: EP190042, 1991, B1,
[55] Tetrahedron Letters, 2010, vol. 51, # 7, p. 1124 - 1125
[56] Revue Roumaine de Chimie, 2011, vol. 56, # 7, p. 705 - 709
[57] Langmuir, 2015, vol. 31, # 39, p. 10831 - 10842
  • 4
  • [ 252316-67-9 ]
  • [ 53463-68-6 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.5 h; Inert atmosphere
Stage #2: With water In diethyl ether; dichloromethane at 20℃; for 7 h; Inert atmosphere
General procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2,2'-bipyridyl (3.0 equiv) in CH2Cl2 (0.2 M) at 0 °C under N2. The reaction mixture was stirred at the same temperature. After checking the disappearance of the starting material on TLC (30 min), H2O (2 mL/mmol) and Et2O (2 mL/mmol) were added to the reaction mixture and vigorously stirred. After disappearance of the high polar component was ascertained by TLC, the reaction mixture was extracted with CH2Cl2. The organic layer was washed with 3.5percent HCl aq twice (for removal of 2,2'-bipyridyl) and with satd NaHCO3 aq. The combined organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography to give an alcohol 2. Silica gel 60 N (neutral) was used for the purification of substrate having TBS or Tr ethers instead of Merck Silica gel 60. Compounds 2e[31a], 2f[4a], 2g31b, 2h31c, 2i31d, 2j31e, and 2k28 are known compounds.
Reference: [1] Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960
[2] Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960
[3] Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960
[4] Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960
  • 5
  • [ 1296645-25-4 ]
  • [ 53463-68-6 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.5 h; Inert atmosphere
Stage #2: With water In diethyl ether; dichloromethane at 20℃; for 5 h; Inert atmosphere
General procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2,2'-bipyridyl (3.0 equiv) in CH2Cl2 (0.2 M) at 0 °C under N2. The reaction mixture was stirred at the same temperature. After checking the disappearance of the starting material on TLC (30 min), H2O (2 mL/mmol) and Et2O (2 mL/mmol) were added to the reaction mixture and vigorously stirred. After disappearance of the high polar component was ascertained by TLC, the reaction mixture was extracted with CH2Cl2. The organic layer was washed with 3.5percent HCl aq twice (for removal of 2,2'-bipyridyl) and with satd NaHCO3 aq. The combined organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography to give an alcohol 2. Silica gel 60 N (neutral) was used for the purification of substrate having TBS or Tr ethers instead of Merck Silica gel 60. Compounds 2e[31a], 2f[4a], 2g31b, 2h31c, 2i31d, 2j31e, and 2k28 are known compounds.
Reference: [1] Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960
  • 6
  • [ 1296645-36-7 ]
  • [ 53463-68-6 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.5 h; Inert atmosphere
Stage #2: With water In dichloromethane at 20℃; for 5 h; Inert atmosphere
General procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2,2'-bipyridyl (3.0 equiv) in CH2Cl2 (0.2 M) at 0 °C under N2. The reaction mixture was stirred at the same temperature. After checking the disappearance of the starting material on TLC (30 min), H2O (2 mL/mmol) and Et2O (2 mL/mmol) were added to the reaction mixture and vigorously stirred. After disappearance of the high polar component was ascertained by TLC, the reaction mixture was extracted with CH2Cl2. The organic layer was washed with 3.5percent HCl aq twice (for removal of 2,2'-bipyridyl) and with satd NaHCO3 aq. The combined organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography to give an alcohol 2. Silica gel 60 N (neutral) was used for the purification of substrate having TBS or Tr ethers instead of Merck Silica gel 60. Compounds 2e[31a], 2f[4a], 2g31b, 2h31c, 2i31d, 2j31e, and 2k28 are known compounds.
Reference: [1] Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960
  • 7
  • [ 1296645-37-8 ]
  • [ 53463-68-6 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.5 h; Inert atmosphere
Stage #2: With water In dichloromethane at 20℃; for 3 h; Inert atmosphere
General procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2,2'-bipyridyl (3.0 equiv) in CH2Cl2 (0.2 M) at 0 °C under N2. The reaction mixture was stirred at the same temperature. After checking the disappearance of the starting material on TLC (30 min), H2O (2 mL/mmol) and Et2O (2 mL/mmol) were added to the reaction mixture and vigorously stirred. After disappearance of the high polar component was ascertained by TLC, the reaction mixture was extracted with CH2Cl2. The organic layer was washed with 3.5percent HCl aq twice (for removal of 2,2'-bipyridyl) and with satd NaHCO3 aq. The combined organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography to give an alcohol 2. Silica gel 60 N (neutral) was used for the purification of substrate having TBS or Tr ethers instead of Merck Silica gel 60. Compounds 2e[31a], 2f[4a], 2g31b, 2h31c, 2i31d, 2j31e, and 2k28 are known compounds.
Reference: [1] Tetrahedron, 2011, vol. 67, # 16, p. 2949 - 2960
  • 8
  • [ 112-47-0 ]
  • [ 53463-68-6 ]
  • [ 4101-68-2 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 27, p. 7735 - 7748
[2] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5837 - 5838
[3] Tetrahedron, 2009, vol. 65, # 20, p. 3961 - 3966
[4] Tetrahedron, 2004, vol. 60, # 24, p. 5237 - 5252
[5] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1215 - 1220
[6] Organic Process Research and Development, 2011, vol. 15, # 3, p. 673 - 680
[7] Helvetica Chimica Acta, 1926, vol. 9, p. 226
[8] Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632
  • 9
  • [ 85920-81-6 ]
  • [ 53463-68-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 11, p. 3527 - 3539
  • 10
  • [ 51309-10-5 ]
  • [ 53463-68-6 ]
Reference: [1] Synthetic Communications, 1994, vol. 24, # 5, p. 733 - 743
  • 11
  • [ 13019-22-2 ]
  • [ 53463-68-6 ]
  • [ 1275582-65-4 ]
  • [ 127102-48-1 ]
Reference: [1] Dalton Transactions, 2012, vol. 41, # 19, p. 5805 - 5815
  • 12
  • [ 50530-12-6 ]
  • [ 53463-68-6 ]
Reference: [1] Journal of Organic Chemistry, 1970, vol. 35, p. 4241 - 4244
  • 13
  • [ 1124-78-3 ]
  • [ 53463-68-6 ]
Reference: [1] Chemistry of Natural Compounds, 1996, vol. 32, # 3, p. 381 - 383
  • 14
  • [ 112-43-6 ]
  • [ 53463-68-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 11, p. 3527 - 3539
  • 15
  • [ 7766-50-9 ]
  • [ 53463-68-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 11, p. 3527 - 3539
  • 16
  • [ 130203-52-0 ]
  • [ 53463-68-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 11, p. 3527 - 3539
  • 17
  • [ 13019-22-2 ]
  • [ 53463-68-6 ]
  • [ 1275582-65-4 ]
  • [ 127102-48-1 ]
  • [ 91717-85-0 ]
Reference: [1] Inorganic Chemistry Communications, 2013, vol. 38, p. 43 - 46
  • 18
  • [ 53463-68-6 ]
  • [ 1611-56-9 ]
Reference: [1] Helvetica Chimica Acta, 1987, vol. 70, p. 822 - 861
  • 19
  • [ 53463-68-6 ]
  • [ 50530-12-6 ]
YieldReaction ConditionsOperation in experiment
73% With chromium(VI) oxide; sulfuric acid; water In acetone at -5 - 20℃; To a solution of 1,10-decandiol (3) (34.8 g, 0.2 mol, 1 equiv) in toluene (400 mL) was added 48percent HBr (22.6 mL, 0.2 mol, 1 equiv) dropwise with stirring and refluxed at 180 °C using Dean-Stark trap for 24 h. The mixture was cooled to room temperature and washed with 6 N NaOH (150 mL), 10percent HCl (150 mL), H2O (2 x 250 mL) and brine (200 mL). The organic layer was dried over Na2SO4, concentrated and chromatographed on silica gel eluting with cyclohexane/ethylacetate (4:1) to give 43.5 g (92percent) of 10-bromo-1-decanol as a colourless liquid. To a solution of 10-bromo-1-decanol (41 g, 0.17 mol, 1 equiv) in 130 mL of acetone at -5 °C was added slowly chromic acid solution prepared from CrO3 (25.7 g, 0.26 mol, 1.5 equiv), water (25 mL) and conc H2SO4 (22.5 mL, 0.34 mol, 2 equiv) at 0 °C, then stirred for 2 h and left over night at room temperature. The mixture was extracted with diethyl ether (3 x 250 mL), washed with water (250 mL) and brine (250 mL), dried over Na2SO4 and concentrated. The residue was chromatographed on silica gel eluting with CH2Cl2 afforded 31.0 g of 10-bromodecanoic acid (4d) (73percent) as a white solid after recrystallization from petroleum ether. Mp 36-37 °C. 1H NMR δ 11.23 (bs, 1H, -OH), 3.41 (t, J = 7.0 Hz, 2H, H-10), 2.36 (t, J = 7.6 Hz, 2H, H-2), 1.87 (m, 2H, H-9), 1.64 (m, 2H, H-3), 1.22-1.44 (m, 10H, H-4-8). 13C NMR δ 180.2 (C1), 34.1 (C2), 34.0 (C10), 32.9, 29.1, 28.9, 28.6, 28.4, 28.2, 24.7.
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[2] Patent: DE867243, 1943, ,
[3] Journal of the American Chemical Society, 1956, vol. 78, p. 2255,2256[4] Journal of Organic Chemistry, 1956, vol. 21, p. 883,885
[5] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 350, p. 93 - 101
[6] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4001 - 4013
  • 20
  • [ 53463-68-6 ]
  • [ 2834-05-1 ]
Reference: [1] Helvetica Chimica Acta, 1929, vol. 12, p. 478
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 53463-68-6 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 4457-67-4

[ 4457-67-4 ]

1-Bromo-4-methoxybutane

Similarity: 0.76

Chemical Structure| 3344-70-5

[ 3344-70-5 ]

1,12-Dibromododecane

Similarity: 0.71

Chemical Structure| 693-58-3

[ 693-58-3 ]

1-Bromononane

Similarity: 0.71

Chemical Structure| 4101-68-2

[ 4101-68-2 ]

1,10-Dibromodecane

Similarity: 0.71

Chemical Structure| 112-82-3

[ 112-82-3 ]

1-Bromohexadecane

Similarity: 0.71

Bromides

Chemical Structure| 4457-67-4

[ 4457-67-4 ]

1-Bromo-4-methoxybutane

Similarity: 0.76

Chemical Structure| 3344-70-5

[ 3344-70-5 ]

1,12-Dibromododecane

Similarity: 0.71

Chemical Structure| 693-58-3

[ 693-58-3 ]

1-Bromononane

Similarity: 0.71

Chemical Structure| 4101-68-2

[ 4101-68-2 ]

1,10-Dibromodecane

Similarity: 0.71

Chemical Structure| 112-82-3

[ 112-82-3 ]

1-Bromohexadecane

Similarity: 0.71

Alcohols

Chemical Structure| 627-18-9

[ 627-18-9 ]

3-Bromopropan-1-ol

Similarity: 0.67

Chemical Structure| 19812-64-7

[ 19812-64-7 ]

Tetradecane-1,14-diol

Similarity: 0.64

Chemical Structure| 112-92-5

[ 112-92-5 ]

1-Hydroxyoctadecane

Similarity: 0.64

Chemical Structure| 1454-85-9

[ 1454-85-9 ]

Heptadecan-1-ol

Similarity: 0.64

Chemical Structure| 112-47-0

[ 112-47-0 ]

1,10-Decanediol

Similarity: 0.64