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[ CAS No. 6117-80-2 ] {[proInfo.proName]}

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Chemical Structure| 6117-80-2
Chemical Structure| 6117-80-2
Structure of 6117-80-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6117-80-2 ]

CAS No. :6117-80-2 MDL No. :MFCD00002924
Formula : C4H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ORTVZLZNOYNASJ-UPHRSURJSA-N
M.W : 88.11 Pubchem ID :643790
Synonyms :

Calculated chemistry of [ 6117-80-2 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 23.19
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : -0.81
Log Po/w (WLOGP) : -0.47
Log Po/w (MLOGP) : -0.33
Log Po/w (SILICOS-IT) : -0.2
Consensus Log Po/w : -0.12

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.26
Solubility : 159.0 mg/ml ; 1.8 mol/l
Class : Highly soluble
Log S (Ali) : 0.44
Solubility : 242.0 mg/ml ; 2.75 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.47
Solubility : 261.0 mg/ml ; 2.96 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 6117-80-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P260-P264-P270-P273-P301+P312+P330-P314-P501 UN#:N/A
Hazard Statements:H302-H373-H402 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6117-80-2 ]

* 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 [ 6117-80-2 ]
  • Downstream synthetic route of [ 6117-80-2 ]

[ 6117-80-2 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 6117-80-2 ]
  • [ 77-76-9 ]
  • [ 1003-83-4 ]
YieldReaction ConditionsOperation in experiment
72% With toluene-4-sulfonic acid In dichloromethane at 20℃; for 3 h; Inert atmosphere To a solution of cis-but-2-ene-1,4-diol (1, 9.3 mL, 113 mmol) in DCM, p-TSA·H2O (1.08 g, 6.2 mmol) was added under argon at room temperature followed by 2,2-dimethoxypropane (27.9 mL, 227 mmol). The reaction mixture was allowed to stir for 3 h. After the completion ofthe reaction, the reaction mixture was quenched with sat. NaHCO3 solution (50 mL) and extracted with DCM (2 × 50 mL). The combined organic layers were washed with brine (25 mL), dried over MgSO4 and the solvent was very slowly removed in vacuo to yield 6 as colourless oil(10.5 g, 72percent). The crude product was directly taken to the next step without purification. Rf = 0.51 (EtOAc/hexane 20percent); 1H NMR (400 MHz, CDCl3) δ 5.66 (2H, t, J = 1.6 Hz, H-1), 4.25 (4H, 2, J = 1.6 Hz, H-2), 1.43 (6H, s, H-4) ppm; 13C NMR (101 MHz, CDCl3 ): δ 129.5 (2C, C-1),102.0 (1C, C-3), 61.4 (2C, C-2), 24.0 (2C, C-4) ppm. Data matches literature
Reference: [1] Helvetica Chimica Acta, 2000, vol. 83, # 7, p. 1633 - 1644
[2] Tetrahedron Asymmetry, 1995, vol. 6, # 6, p. 1261 - 1272
[3] Patent: US5962704, 1999, A,
[4] Patent: US6133461, 2000, A,
[5] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 2883 - 2887
[6] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993, # 5, p. 871 - 877
[7] Canadian Journal of Chemistry, 1981, vol. 59, p. 2283 - 2289
  • 2
  • [ 6117-80-2 ]
  • [ 116-11-0 ]
  • [ 1003-83-4 ]
Reference: [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 2010, vol. 132, p. 3268 - 3269
  • 3
  • [ 6117-80-2 ]
  • [ 67-64-1 ]
  • [ 1003-83-4 ]
Reference: [1] Chemische Berichte, 1980, vol. 113, # 4, p. 1472 - 1479
  • 4
  • [ 6117-80-2 ]
  • [ 126-84-1 ]
  • [ 1003-83-4 ]
Reference: [1] Synthesis, 1981, # 8, p. 612 - 613
  • 5
  • [ 6117-80-2 ]
  • [ 106-40-1 ]
  • [ 5044-39-3 ]
Reference: [1] ChemSusChem, 2016, vol. 9, # 17, p. 2321 - 2325
[2] Journal of Organic Chemistry, 2018, vol. 83, # 24, p. 15406 - 15414
  • 6
  • [ 6117-80-2 ]
  • [ 108-24-7 ]
  • [ 25260-60-0 ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine In tetrahydrofuran at 20℃; for 16 h; To a stirred solution of 20.5 mL (0.25 mol) but-2-ene-1 ,4-diol and 105 mL (0.75 mol) triethylamine in 400 mL tetrahydrofuran was added 60 mL (0.63 mol) acetic anhydride at ambient temperature. After 16 h stirring, 300 mL saturated aq. sodium bicarbonate solution and 300 mL diethylether were added. The aq. layer was extracted with 200 mL diethylether and the combined organic phase was washed with 300 mL brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by vacuum distillation (3 mbar, 80-820C) to give 39.3 g of the diacetate, corresponding to a yield of 91percent based on but-2-ene-1 ,4-diol. To a stirred solution of 17.2 g diacetate (100 mmol) in a mixture of 150 mL acetone and 50 mL water were added 26 g N-methylmorpholine-N-oxide (NMO, 200 mmol) and 270 mg K2OsO4-H2O <n="19"/>(0.75 mmol) at ambient temperature. After 3 h stirring, TLC showed complete conversion of the diacetate and 300 ml. saturated aq. sodium hydrogen sulfite solution and 300 mL ethylacetate were added. The aq. layer was extracted with 600 mL ethylacetate and the combined organic phase was washed with 400 mL brine, dried (Na2SO4) and concentrated in vacuo to give 18.5 g of the diol as white crystals, corresponding to a yield of 90percent yield based on the diacetate. To a stirred solution of 8.2 g diol (40 mmol) in 150 mL dichloromethane was added 80 g sodium periodate on silica (55 mmol) at ambient temperature. After 1 .4 h stirring, TLC showed complete conversion. The silica was removed by filtration and rinsed with 100 mL dichloromethane. The combined filtrates were concentrated in vacuo and the residue purified by careful distillation to give 4.1 g of the aldehyde, corresponding to 50percent yield based on the diol. The identity of the compound was confirmed by 1H and 13C NMR spectroscopy.
89% With pyridine In dichloromethane at 0 - 20℃; for 18.5 h; Inert atmosphere The entire synthesis was performed in an inert atmosphere. First, 79.63 g (0.78 mol) fresh distilled acetic acid anhydride was added dropwise to a solution of 20.26 g(0.23 mol) cis-2-butene-1,4-diol in 20 mL abs. dichloromethane at 0 °C. Afterwards, 55.37 g (0.7 mol) pyridine was added dropwise and the solution was stirred for 30 min at 0 °C. After being stirred for 18 h at room temperature, the reaction solution was washed three times with 30 mL 2 M HCl and with 25 mL brine. The organic product phase was dried with MgSO4. After that, the solvent of the reaction was removed. A 35.10-g amount of cis-1,4-diacetoxy-2-butene 5 (0.20 mol, 89 percent) were isolated as a colorless liquid with a purity of about 98.5 percent.
Reference: [1] Synthesis, 1992, # 10, p. 1007 - 1012
[2] Tetrahedron, 1997, vol. 53, # 48, p. 16423 - 16434
[3] Tetrahedron Letters, 1997, vol. 38, # 20, p. 3595 - 3598
[4] Patent: WO2008/34598, 2008, A1, . Location in patent: Page/Page column 17-18
[5] Tetrahedron Asymmetry, 2001, vol. 12, # 5, p. 691 - 693
[6] Chemical Communications, 2003, # 15, p. 1834 - 1835
[7] JAOCS, Journal of the American Oil Chemists' Society, 2015, vol. 92, # 4, p. 603 - 611
[8] European Journal of Organic Chemistry, 2001, # 17, p. 3301 - 3305
[9] Synthesis, 1982, # 6, p. 469 - 471
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2061 - 2068
[11] Angewandte Chemie - International Edition, 2016, vol. 55, # 51, p. 15792 - 15796[12] Angew. Chem., 2016, vol. 128, # 51, p. 16024 - 16028,5
[13] Annales de Chimie (Cachan, France), 1948, vol. &lt;12&gt;3, p. 674[14] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1946, vol. 223, p. 908
[15] Journal of Organic Chemistry, 1956, vol. 21, p. 328,330
[16] Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 65
[17] Angewandte Chemie - International Edition, 2011, vol. 50, # 44, p. 10402 - 10405
  • 7
  • [ 6117-80-2 ]
  • [ 75-36-5 ]
  • [ 25260-60-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 48, p. 9270 - 9273
[2] Organic Letters, 2018, vol. 20, # 8, p. 2253 - 2256
[3] Tetrahedron, 2005, vol. 61, # 46, p. 10903 - 10907
  • 8
  • [ 108-22-5 ]
  • [ 6117-80-2 ]
  • [ 25260-60-0 ]
YieldReaction ConditionsOperation in experiment
99% at 60℃; for 2 h; General procedure: In a typical procedure, in a capped vessel alcohol 3a (0.5 mmol) and ester 2a (1.5 mmol) were added sequentially to the TEAHC (35.0 mg, 0.15 mmol); the reaction mixture was stirred for 2 h at 60 °C and then transferred in a round-bottomed flask and concentrated under reduced pressure. The residue mixture was then extracted with diethyl ether (3 times with 10 cm3). After removal of the solvent from the combined ethereal layers under reduced pressure, the crude reaction mixture was analyzed by 1H and 13C NMR and thin-layer chromatography (TLC). All products were purified by using flash chromatography (n-hexane / ethyl acetate, 95/5) and identified on the basis of NMR spectroscopic analysis by comparison with reported data.
Reference: [1] Synthetic Communications, 2016, vol. 46, # 22, p. 1840 - 1847
  • 9
  • [ 6117-80-2 ]
  • [ 108-24-7 ]
  • [ 64196-68-5 ]
  • [ 25260-60-0 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 804 - 807
[2] Synthesis, 1993, # 3, p. 321 - 324
[3] Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 312 - 316
  • 10
  • [ 6117-80-2 ]
  • [ 141-78-6 ]
  • [ 64196-68-5 ]
  • [ 25260-60-0 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 312 - 316
  • 11
  • [ 6117-80-2 ]
  • [ 141-78-6 ]
  • [ 25260-60-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 14, p. 2223 - 2225
  • 12
  • [ 6117-80-2 ]
  • [ 25260-60-0 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1960, p. 1001 - 1006[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1960, p. 1073 - 1079
  • 13
  • [ 6117-80-2 ]
  • [ 112-80-1 ]
  • [ 4494-16-0 ]
  • [ 75039-83-7 ]
  • [ 79868-94-3 ]
  • [ 5557-31-3 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1 - 8
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