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[ CAS No. 5272-36-6 ] {[proInfo.proName]}

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Chemical Structure| 5272-36-6
Chemical Structure| 5272-36-6
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Product Details of [ 5272-36-6 ]

CAS No. :5272-36-6 MDL No. :MFCD00002913
Formula : C6H12OSi Boiling Point : -
Linear Structure Formula :- InChI Key :ZVGCJDPEKKEYES-UHFFFAOYSA-N
M.W : 128.24 Pubchem ID :78930
Synonyms :

Calculated chemistry of [ 5272-36-6 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.15
TPSA : 20.23 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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 1.61
Log Po/w (WLOGP) : 0.94
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : -0.41
Consensus Log Po/w : 1.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.65
Solubility : 2.87 mg/ml ; 0.0224 mol/l
Class : Very soluble
Log S (Ali) : -1.65
Solubility : 2.89 mg/ml ; 0.0226 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.02
Solubility : 12.3 mg/ml ; 0.0957 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.83

Safety of [ 5272-36-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5272-36-6 ]

* 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 [ 5272-36-6 ]
  • Downstream synthetic route of [ 5272-36-6 ]

[ 5272-36-6 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 5272-36-6 ]
  • [ 5683-31-8 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1985, # 7, p. 421
[2] Chemische Berichte, 1988, vol. 121, p. 1151 - 1158
[3] Journal of Chemical Research, 2004, # 2, p. 107 - 110
[4] Journal of Chemical Research, Miniprint, 1981, # 9, p. 3261 - 3278
[5] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8344 - 8347
  • 2
  • [ 5272-36-6 ]
  • [ 59376-64-6 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4 h; Heating / reflux
Stage #2: With water; ammonium chloride In tetrahydrofuran
Example 41; (2E)-3-(Trimethylsilyl)prop-2-en-1-ol; The alcohol produced in Example 40 (1.54 g, 12 mmol, 1 eq) in dry THF (12 mL) was added dropwise, with stirring, to a suspension of LiAlH4 (0.7 g, 18 mmol, 1.5 eq) in THF (15 mL) at room temperature, under argon. The mixture was then refluxed for 4 hours and quenched with sat. NH4.Cl. This was extracted with Et2O (3.x.50 mL) and the combined organic layers were washed with brine, dried over MgSO4 and the solvent removed in vacuo to furnish the product (1.39 g, 10.6 mmol, 89percent yield) as a colourless liquid. 1H NMR (400 MHz, CDCl3) δ 6.19 (1H, m, H-3), 5.93 (1H, dt, J2-3=18.8 Hz, J2-4=1.45 Hz, H-2), 4.18 (2H, dd, J4-3=2.72, J4-2=1.45, H-4), 1.56 (1H, s, H-5), 0.09 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 144.8 (C-3), 129.5 (C-2), 65.5 (C-4), -1.37 (C-5); IR (neat, cm-1) 3331 (b, OH) 1622 (s, CC).
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 20, p. 4682 - 4693
[2] Journal of the American Chemical Society, 1989, vol. 111, # 24, p. 8834 - 8841
[3] Tetrahedron, 1996, vol. 52, # 21, p. 7487 - 7510
[4] Chinese Journal of Chemistry, 2018, vol. 36, # 10, p. 916 - 920
[5] Patent: US2007/142632, 2007, A1, . Location in patent: Page/Page column 26
[6] Tetrahedron Letters, 1986, vol. 27, # 12, p. 1411 - 1414
[7] Chemische Berichte, 1988, vol. 121, p. 1151 - 1158
[8] Chemische Berichte, 1982, vol. 115, # 12, p. 3737 - 3746
[9] Helvetica Chimica Acta, 2002, vol. 85, # 12, p. 4165 - 4181
[10] Organic Syntheses, 1986, vol. 64, p. 182 - 182
[11] Organic and Biomolecular Chemistry, 2014, vol. 12, # 35, p. 6842 - 6854
[12] Organic Letters, 2006, vol. 8, # 4, p. 597 - 600
[13] Journal of Organic Chemistry, 1977, vol. 42, p. 3109 - 3113
[14] Journal of the American Chemical Society, 1974, vol. 96, # 11, p. 3684 - 3686
[15] Tetrahedron Letters, 1984, vol. 25, # 26, p. 2821 - 2822
[16] Journal of the Chemical Society, Chemical Communications, 1982, # 19, p. 1126 - 1127
[17] Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 5743 - 5753
[18] Tetrahedron Letters, 2007, vol. 48, # 48, p. 8442 - 8448
[19] Tetrahedron, 1986, vol. 42, # 16, p. 4427 - 4436
[20] Angewandte Chemie - International Edition, 2007, vol. 46, # 24, p. 4554 - 4558
[21] Organic and Biomolecular Chemistry, 2016, vol. 14, # 45, p. 10667 - 10673
  • 3
  • [ 5272-36-6 ]
  • [ 59376-64-6 ]
YieldReaction ConditionsOperation in experiment
90% With sulfuric acid In hexane; ethyl acetate; toluene EXAMPLE 38
Preparation of (E)-3-Trimethylsilyl-2-Propen-1-Ol
2 g (15.6 mmol) of 3-trimethylsilyl-2-propyn-1-ol in 10 ml of dry ether are added dropwise to an ice-cooled solution of sodium bis(2-methoxyethoxy) aluminum [Red-Al. 3.4M in toluene, (7.3 ml, 25.1 mmol)] in 10 ml of dry ether.
The reaction mixture is then further stirred during 2 hours at room temperature and poured into an ice-cooled sulfuric acid (1N) ether mixture.
If necessary the pH is adjusted to be slightly basic, the organic phase is then removed and the aqueous phase is further extracted with ether.
The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure.
Rapid flash chromatography of the residue on a silica gel column eluted with a 8:2 mixture of hexane and ethyl acetate affords the expected (E)-3-trimethylsilyl-2-propen-1-ol as a colorless liquid (1.8 g, 90percent).
90% With sulfuric acid In hexane; ethyl acetate; toluene EXAMPLE 38
Preparation of (E)-3-Trimethylsilyl-2-Propen-1-Ol
2 g (15.6 mmol) of 3-trimethylsilyl-2-propyn-1-ol in 10 ml of dry ether are added dropwise to an ice-cooled solution of sodium bis(2-methoxyethoxy) aluminum [Red-A1. 3.4M in toluene, (7.3 ml, 25.1 mmol)] in 10 ml of dry ether.
The reaction mixture is then further stirred during 21/2 hours at room temperature and poured into an ice-cooled sulfuric acid (1N) ether mixture.
If necessary the pH is adjusted to be slightly basic, the organic phase is then removed and the aqueous phase is further extracted with ether.
The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure.
Rapid flash chromatography of the residue on a silica gel column eluted with a 8:2 mixture of hexane and ethyl acetate affords the expected (E)-3-trimethylsilyl-2-propen-1-ol as a colorless liquid (1.8 g, 90percent).
Reference: [1] Patent: US5536732, 1996, A,
[2] Patent: US5252587, 1993, A,
  • 4
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  • [ 62861-80-7 ]
  • [ 59376-64-6 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1982, # 19, p. 1126 - 1127
  • 5
  • [ 5272-36-6 ]
  • [ 59376-64-6 ]
  • [ 192064-71-4 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 22, p. 3829 - 3832
  • 6
  • [ 36551-06-1 ]
  • [ 5272-36-6 ]
YieldReaction ConditionsOperation in experiment
96% With Amberlyst® 15 In methanol at 0 - 40℃; for 8 h; Inert atmosphere In a flask containing methanol (4.0 mL) and Amberlyst-15 (0.025 g) under N2, compound 5 (0.250 g,1.17 mmol) was added dropwise at 0 °C. The mixture was stirred at 40 °C for 8 hr, then the resin was filtered, and washed with ethyl acetate (10 mL). A 10 percent aqueous solution of HCl (10 mL) was added and the organic layer was extracted with ethyl acetate (3 × 10 mL), and dried over Na2SO4. After concentration, the residue was purified by column chromatography (hexane/ethyl acetate 9:1) to afford compound 6 in 96 percent yield (0.143 g, 1.12 mmol).
Reference: [1] Tetrahedron, 1996, vol. 52, # 21, p. 7487 - 7510
[2] Journal of the Brazilian Chemical Society, 2013, vol. 24, # 12, p. 1933 - 1941
[3] Chemistry - A European Journal, 2015, vol. 21, # 27, p. 9662 - 9665
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987, p. 1077 - 1082
[5] Journal of Organic Chemistry, 1995, vol. 60, # 14, p. 4650 - 4652
[6] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9206 - 9209
  • 7
  • [ 75-77-4 ]
  • [ 107-19-7 ]
  • [ 5272-36-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 2, p. 330 - 344
[2] Journal of Chemical Research, 2004, # 2, p. 107 - 110
[3] Organic letters, 2002, vol. 4, # 4, p. 565 - 568
[4] Journal of the American Chemical Society, 2016, vol. 138, # 3, p. 770 - 773
[5] Organic Letters, 2006, vol. 8, # 17, p. 3761 - 3764
[6] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 9040 - 9045
[7] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6127 - 6130
[8] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8122 - 8126
[9] Chemical Communications, 2015, vol. 51, # 35, p. 7493 - 7496
[10] Organic Syntheses, 1986, vol. 64, p. 182 - 182
[11] Organic Letters, 2008, vol. 10, # 24, p. 5529 - 5531
[12] Helvetica Chimica Acta, 2002, vol. 85, # 12, p. 4165 - 4181
[13] Organic Letters, 2002, vol. 4, # 4, p. 485 - 488
[14] Journal of the American Chemical Society, 2009, vol. 131, # 41, p. 14673 - 14675
[15] Organic and Biomolecular Chemistry, 2014, vol. 12, # 35, p. 6842 - 6854
[16] Tetrahedron Letters, 2003, vol. 44, # 27, p. 4989 - 4992
[17] Chemistry - A European Journal, 2005, vol. 11, # 5, p. 1610 - 1624
[18] Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13692 - 13696
[19] European Journal of Organic Chemistry, 2013, # 29, p. 6584 - 6600
[20] Canadian Journal of Chemistry, 2004, vol. 82, # 2, p. 215 - 226
[21] Canadian Journal of Chemistry, 2004, vol. 82, # 2, p. 227 - 239
[22] Tetrahedron, 1994, vol. 50, # 31, p. 9425 - 9438
[23] Organic Letters, 2006, vol. 8, # 4, p. 597 - 600
[24] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 307 - 314
[25] Tetrahedron Letters, 1973, p. 3964 - 3966
[26] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 1981 - 1987
[27] Synthesis, 1976, p. 777 - 794
[28] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1960, p. 1208 - 1210[29] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1960, # 7, p. 1300 - 1302
[30] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1960, p. 1911 - 1913[31] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1960, # 11, p. 2059 - 2061
[32] Tetrahedron Letters, 1988, vol. 29, # 37, p. 4773 - 4776
[33] Tetrahedron, 1983, vol. 39, # 6, p. 935 - 948
[34] Tetrahedron, 1985, vol. 41, # 24, p. 5861 - 5869
[35] Journal of Organic Chemistry, 1987, vol. 52, # 10, p. 1889 - 1902
[36] Journal of Medicinal Chemistry, 1984, vol. 27, # 10, p. 1351 - 1354
[37] Tetrahedron Letters, 1994, vol. 35, # 51, p. 9497 - 9500
[38] Tetrahedron, 1996, vol. 52, # 35, p. 11601 - 11624
[39] Journal of Organometallic Chemistry, 1998, vol. 564, # 1-2, p. 61 - 70
[40] Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 5743 - 5753
[41] Angewandte Chemie - International Edition, 2007, vol. 46, # 24, p. 4554 - 4558
[42] Chemistry - A European Journal, 2011, vol. 17, # 15, p. 4118 - 4130
[43] Macromolecules, 2010, vol. 43, # 3, p. 1438 - 1443
[44] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 5, p. 831 - 835
[45] ChemCatChem, 2013, vol. 5, # 10, p. 2939 - 2945
[46] ChemMedChem, 2018, vol. 13, # 11, p. 1124 - 1130
  • 8
  • [ 50-00-0 ]
  • [ 1066-54-2 ]
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Reference: [1] Chemistry - A European Journal, 2005, vol. 11, # 8, p. 2577 - 2590
[2] Chinese Journal of Chemistry, 2018, vol. 36, # 10, p. 916 - 920
[3] Tetrahedron Letters, 1999, vol. 40, # 43, p. 7605 - 7609
[4] Chemical Communications, 2006, # 39, p. 4113 - 4115
[5] Journal of the American Chemical Society, 2000, vol. 122, # 9, p. 1937 - 1944
[6] European Journal of Organic Chemistry, 2009, # 21, p. 3605 - 3612
  • 9
  • [ 50965-66-7 ]
  • [ 5272-36-6 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 10, p. 837 - 847
[2] Journal of Organic Chemistry, 1986, vol. 51, # 18, p. 3451 - 3453
[3] Tetrahedron Letters, 1994, vol. 35, # 21, p. 3525 - 3528
[4] Chemistry - A European Journal, 2004, vol. 10, # 20, p. 5087 - 5110
[5] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8648 - 8651[6] Angew. Chem., 2013, vol. 125, # 33, p. 8810 - 8813,4
  • 10
  • [ 75-77-4 ]
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YieldReaction ConditionsOperation in experiment
37%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333 h;
Stage #2: at -78 - 20℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 16 h;
Example 40; 3-(Trimethylsilyl)prop-2-yn-1-ol; n-BuLi (27.3 mL, 44 mmol, 2.2 eq.) was added dropwise to a stirred solution of 2-propyn-1-ol (1.16 mL, 20 mmol, 1 eq.) in THF (60 mL) at -78° C. under argon. After 20 minutes, trimethylsilyl chloride (52 mL, 60 mmol, 2 eq.) was added dropwise and the mixture allowed to warm to room temperature. 2M HCl (40 mL) was added at 0° C., and the reaction mixture was stirred at room temperature for 16 hours. The organic layer was separated and the aqueous layer extracted with Et2O (3.x.60 mL), the combined organics were washed with brine, dried over MgSO4 and the solvent removed in vacuo. Column chromatography (cyclohexane followed by Et2O), distillation using Kugelrohr apparatus (95-100° C., 11 mbar) and further column chromatography (hexane:Et2O 60:40) furnished the product (0.96g, 7.5 mmol, 37percent yield) as a colourless liquid. Rf=0.55 (cyclohexane:Et2O 1:1); 1H NMR (400 MHz, CDCl3) δ 4.28 (2H, s, H-4), 1.64 (1H, s, H-5), 0.18 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 104.10 (C-3), 91.03 (C-2), 51.99 (C-4), 0.00 (C-1); IR (neat, cm-1) 3426 (b, OH), 2253 (s, C.ident.C); MS (lit.- Bunce, R.; Hertzler, D., J. Org. Chem 1986, 51, 3451-3453: m/z 128.0695).
Reference: [1] Patent: US2007/142632, 2007, A1, . Location in patent: Page/Page column 26
  • 11
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YieldReaction ConditionsOperation in experiment
45% With sec.-butyllithium In tetrahydrofuran; hexane at -45 - 20℃; for 6 h; Inert atmosphere A cold (-50 °C) solution of ether 1 (10.2 g, 0.08 mol) in anhydrous THF (50 mL) was added to a solution of BusLi (obtained from BusCl (7.4 g, 0.08 mol) and fine dispersion of lithium (1.39 g, 0.2 mol)) in anhydrous hexane (50 mL) cooled to -60 °C over 10 min. The reaction mixture was stirred under an inert atmosphere for 1 h at -45 °C, then the temperature was gradually increased to ambient over 5 h. The reaction mixture was quenched with 10percent aqueous HCl and extracted with diethyl ether. The extract was dried with MgSO4, the solvent was evaporated. The residue was distilled in vacuo to obtain 3-trimethyl-silylprop-2-yn-1-ol (4) (4.6 g, 45percent), b.p. 74—75 °C (11 Torr). IR (microlayer), n/cm-1: 2174 (Si—CC—), 1240 (CH3—Si). 1H NMR (CDCl3), d: 4.28 (s, 2 H, CH2O); 0.17 (s, 9 H, (CH3)3SiC). 13 NMR (CDCl3), d: 104.15 (Si—CC); 89.82 (Si—CC); 51.58 (CH2O); -0.29 ((CH3)3Si—C); -0.11 (OSi(CH3)3).
Reference: [1] Russian Journal of Organic Chemistry, 1996, vol. 32, # 12, p. 1770 - 1773
[2] Journal of Organometallic Chemistry, 1998, vol. 553, # 1-2, p. 481 - 482
[3] Russian Journal of Organic Chemistry, 1996, vol. 32, # 12, p. 1770 - 1773
[4] Synthesis, 1991, # 11, p. 979 - 982
[5] Russian Journal of Organic Chemistry, 2001, vol. 37, # 11, p. 1549 - 1552
[6] Russian Chemical Bulletin, 2017, vol. 66, # 12, p. 2264 - 2268
[7] Russian Journal of General Chemistry, 1994, vol. 64, # 7.2, p. 1101 - 1102[8] Zhurnal Obshchei Khimii, 1994, vol. 64, # 7, p. 1224
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Reference: [1] Journal of Organometallic Chemistry, 1998, vol. 553, # 1-2, p. 129 - 133
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  • [ 233282-84-3 ]
Reference: [1] Russian Journal of Organic Chemistry, 1998, vol. 34, # 10, p. 1426 - 1431
  • 14
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Reference: [1] Patent: EP244962, 1991, B1,
  • 15
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  • [ 1092574-48-5 ]
Reference: [1] Synthesis, 2011, # 9, p. 1347 - 1360
  • 16
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  • [ 2170-06-1 ]
Reference: [1] Russian Journal of Organic Chemistry, 2001, vol. 37, # 11, p. 1549 - 1552
  • 17
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Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 23, p. 4595 - 4597
  • 20
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Reference: [1] Russian Journal of Organic Chemistry, 1996, vol. 32, # 12, p. 1770 - 1773
  • 23
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Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 17, p. 2823 - 2826
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Reference: [1] Russian Journal of Organic Chemistry, 1996, vol. 32, # 12, p. 1770 - 1773
  • 25
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Reference: [1] Mendeleev Communications, 2005, vol. 15, # 6, p. 263 - 265
[2] Chemistry - A European Journal, 2015, vol. 21, # 27, p. 9662 - 9665
[3] Advanced Synthesis and Catalysis, 2017, vol. 359, # 18, p. 3207 - 3216
[4] Synthesis, 1991, # 11, p. 979 - 982
[5] Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 10, p. 837 - 847
[6] Chemistry - A European Journal, 2005, vol. 11, # 5, p. 1610 - 1624
[7] Synthesis, 2008, # 23, p. 3797 - 3800
[8] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9206 - 9209
[9] Journal of the American Chemical Society, 1994, vol. 116, # 14, p. 6121 - 6129
[10] Organic Letters, 2008, vol. 10, # 24, p. 5529 - 5531
[11] European Journal of Organic Chemistry, 2013, # 29, p. 6584 - 6600
[12] Tetrahedron, 1995, vol. 51, # 27, p. 7389 - 7402
[13] European Journal of Organic Chemistry, 2005, # 7, p. 1444 - 1458
[14] Chemistry - A European Journal, 2004, vol. 10, # 20, p. 5087 - 5110
[15] Organic letters, 2002, vol. 4, # 4, p. 565 - 568
[16] Chemistry - A European Journal, 2007, vol. 13, # 19, p. 5378 - 5387
[17] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 11, p. 1457 - 1463
[18] Chemistry - A European Journal, 2011, vol. 17, # 15, p. 4118 - 4130
[19] Chemistry - A European Journal, 2013, vol. 19, # 39, p. 13017 - 13029
[20] Journal of the American Chemical Society, 2016, vol. 138, # 3, p. 770 - 773
[21] ChemMedChem, 2018, vol. 13, # 11, p. 1124 - 1130
  • 26
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YieldReaction ConditionsOperation in experiment
70% With bromine; triphenylphosphine In dichloromethane at 0℃; for 1 h; Inert atmosphere To a solution of triphenylphosphine (9.735 g, 37.11 mmol) in dry dichloromethane (46.0 mL) under N2, bromine (5.438 g, 34.03 mmol) was added at 0 °C. After 30 min, when the solution color changed from orange to white, compound 6 (3.960 g, 30.93 mmol) was slowly added. The mixture was stirred for 1 h, and then it was washed with water (3 × 30 mL) and a 10 percent aqueous solution of HCl (2 × 20 mL). The aqueous layer was extracted with ethyl acetate (3 × 20 mL), and then the combined organic layers was dried over Na2SO4 and concentrated in vacuum. The residue was purified by column chromatography, using hexane as eluent, to afford compound 7 in 70 percent yield (4.125 g, 21.6 mmol).
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8122 - 8126
[2] Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13692 - 13696
[3] Tetrahedron, 1996, vol. 52, # 35, p. 11601 - 11624
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6127 - 6130
[5] Bulletin de la Societe Chimique de France, 1993, vol. 130, # 2, p. 154 - 159
[6] Journal of the American Chemical Society, 1981, vol. 103, # 7, p. 1831 - 1835
[7] Journal of the Brazilian Chemical Society, 2013, vol. 24, # 12, p. 1933 - 1941
[8] Organic Letters, 2002, vol. 4, # 4, p. 485 - 488
[9] Journal of Medicinal Chemistry, 1984, vol. 27, # 10, p. 1351 - 1354
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  • [ 5272-36-6 ]
  • [ 62108-37-6 ]
  • [ 74542-82-8 ]
Reference: [1] Organic Syntheses, 1988, vol. 66, p. 1 - 1
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