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[ CAS No. 700-58-3 ] {[proInfo.proName]}

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Chemical Structure| 700-58-3
Chemical Structure| 700-58-3
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Product Details of [ 700-58-3 ]

CAS No. :700-58-3 MDL No. :MFCD00074737
Formula : C10H14O Boiling Point : -
Linear Structure Formula :- InChI Key :IYKFYARMMIESOX-UHFFFAOYSA-N
M.W :150.22 Pubchem ID :64151
Synonyms :
Adamantanone

Calculated chemistry of [ 700-58-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.04
TPSA : 17.07 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 2.01
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 2.34
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.89
Solubility : 1.92 mg/ml ; 0.0128 mol/l
Class : Very soluble
Log S (Ali) : -1.76
Solubility : 2.63 mg/ml ; 0.0175 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.6
Solubility : 3.8 mg/ml ; 0.0253 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.67

Safety of [ 700-58-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 700-58-3 ]

* 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 [ 700-58-3 ]
  • Downstream synthetic route of [ 700-58-3 ]

[ 700-58-3 ] Synthesis Path-Upstream   1~40

  • 1
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1986, # 23, p. 1701 - 1702
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  • [ 39751-07-0 ]
  • [ 19214-00-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 947 - 956
  • 3
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  • [ 108-24-7 ]
  • [ 39751-07-0 ]
  • [ 20098-14-0 ]
  • [ 63382-10-5 ]
  • [ 19214-00-7 ]
Reference: [1] Synthetic Communications, 1999, vol. 29, # 18, p. 3221 - 3225
  • 4
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YieldReaction ConditionsOperation in experiment
74%
Stage #1: at 60℃; for 74.25 h; Cooling with ice
Stage #2: for 1 h; Heating
Step (i): Preparation of compound of formula (11)Adamantanone (50 grams, 333 mmol) was added with stirring to nitric acid (98percent, 440 mL) at ice bath temperature over a period of 15 minutes. The reaction mixture was stirred at room temperature for 72 hours and then heated at 60 °C, for 2 hours until most of the nitrogen dioxide evaporated. Excess nitric acid was distilled off under reduced pressure. The light yellow oil solidified upon cooling. The reaction mixture was diluted with water (200 mL) and concentrated sulphuric acid (75 mL). The resultant clear yellow solution was heated on the steam bath in a hood for 1 hour. The reaction mixture was neutralized with 30percent aqueous sodiumhydroxide solution, and while warm, extracted with chloroform. The extracts were combined, washed with brine solution and concentrated in vacuum. The crude product was dissolved in dichloromethane ( 15 mL) and hexane was added until no more precipitate was formed. The solid material was isolated by filtration and dried under vacuum to obtain compound of formula (11) (40.9 grams). Yield: 74 percent. Melting Range: 278.8-300 °C; -NMR (CDCI3): δ 2.69 (bs, 2H), 2.36-2.32 (m, 2H), 2.12-2.02 (m, 2H), 2.02-1 :88 (m, 6H), 1.80- 1.68 (m, 1H).IR: 3410, 2929, 2855, 2645, 1725, 1539, 1452, 1351, 1288, 1 1 16, 1055, 927, 900, 797;Mass (m/z): 167 [Μ+Η+].
70%
Stage #1: With nitric acid In water at 0 - 60℃; for 74.25 h;
Stage #2: With sulfuric acid In water for 1 h; Heating / reflux
Adamantanone (12 g, 80 mmol) was added under stirring to nitric acid (98percent, 100 mL) at ice bath temperature over a period of 15 minutes. The reaction mixture was stirred at room temperature for 72 h and then heated to 60 °C, for 2 h until most of the nitrogen dioxide evaporated. Excess nitric acid was distilled off under reduced pressure. The light yellow oil solidified upon cooling (NO3 adduct of the hydroxyketone). Water (40 mL) and cone. H2SO4 (98percent, 15 mL) were added. The resulting clear yellow solution was heated on the steam bath in a hood (nitrous fumes) for 1 h. The solution was then cooled and extracted with a 2:1 mixture of n-hexane and diethylether to remove unreacted adamantanone (1.0 g). The acid layer was neutralized with 30percent aq. NaOH solution, and while warm, extracted with chloroform. The extracts were combined, washed with brine solution, and concentrated in vacuum. The crude product was dissolved in CH2Cl2 (15 mL) and hexane was added until no more precipitate was formed. The solid material was isolated by filtration and dried to get 5-hydroxy-adamantan-2-one. Yield: 9.0 g (70percent). Solid; M.R: 278.8-300 °C (decomposes) m/z (M+l) 167; 1H NMR (CDCl3) 300 MHz δ 2.70-2.55 (m, 2H)5 2.36-2.32 (m5 IH), 2.11-1.93 (m, 10H). 13C NMR (CDCl3) 75 MHz δ 217.0, 66.7, 46.7, 46.6, 44.7 (2C), 43.8, 37.9 (2C), 29.5.
Reference: [1] Russian Journal of Organic Chemistry, 2009, vol. 45, # 8, p. 1137 - 1142
[2] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1099 - 1101
[3] Patent: WO2011/30349, 2011, A1, . Location in patent: Page/Page column 23-24
[4] Patent: WO2007/113634, 2007, A1, . Location in patent: Page/Page column 49
[5] Chemical Communications, 2014, vol. 50, # 2, p. 186 - 188
[6] Synthesis, 1972, p. 374 - 375
[7] Organic Letters, 2003, vol. 5, # 16, p. 2943 - 2946
[8] Synthetic Communications, 1984, vol. 14, # 1, p. 65 - 68
[9] Russian Journal of Organic Chemistry, 2002, vol. 38, # 8, p. 1125 - 1129
[10] Patent: US6461876, 2002, B1,
[11] Patent: US2004/77018, 2004, A1,
[12] Patent: US7422908, 2008, B2,
[13] Patent: EP2048140, 2009, A1, . Location in patent: Page/Page column 13
[14] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 94, p. 111 - 118
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  • [ 73346-81-3 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 94, p. 111 - 118
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  • [ 20098-14-0 ]
Reference: [1] Patent: US6229050, 2001, B1,
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  • [ 20098-14-0 ]
Reference: [1] Patent: US6229050, 2001, B1,
[2] Patent: US6229050, 2001, B1,
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  • [ 20098-14-0 ]
Reference: [1] Patent: US6486330, 2002, B1,
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  • [ 20098-14-0 ]
Reference: [1] Patent: US6229050, 2001, B1,
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Reference: [1] Patent: US6229050, 2001, B1,
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Reference: [1] Patent: US5395846, 1995, A,
  • 12
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  • [ 108-24-7 ]
  • [ 39751-07-0 ]
  • [ 20098-14-0 ]
  • [ 63382-10-5 ]
  • [ 19214-00-7 ]
Reference: [1] Synthetic Communications, 1999, vol. 29, # 18, p. 3221 - 3225
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  • [ 20098-14-0 ]
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  • [ 19439-20-4 ]
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Reference: [1] Chemische Berichte, 1984, vol. 117, # 5, p. 1982 - 1986
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Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 13, p. 5103 - 5110
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  • [ 702-98-7 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: at 0℃; for 0.5 h;
Stage #2: With ammonium chloride In tetrahydrofuran
3M Methylmagnesium chloride in THF (44 mL), was added through a canula to adamantan-2-one(10 g, 66.66 mmol) in THF (50 mL) at 0 °C. After stirring at 0 °C for 0.5 h, the reaction mixture was quenched by adding saturated NH4C1 solution. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with water and brine, dried over Na2S04 and the solvent was removed under reduced pressure to afford 2-methyladamantan-2-ol (11 g, 99percent yield) as an off-white solid.
Reference: [1] Patent: WO2011/58582, 2011, A1, . Location in patent: Page/Page column 27
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 9, p. 2532 - 2537
[3] Heterocycles, 1986, vol. 24, # 12, p. 3441 - 3446
[4] Tetrahedron, 2000, vol. 56, # 37, p. 7237 - 7243
  • 16
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YieldReaction ConditionsOperation in experiment
95% at 0 - 20℃; Inert atmosphere 2-methyl-2-adamantol (56)To a solution of 2-adamantone (1.5Og, lOmmol) in ether was added CH3Li (7.5ml, 1.6M in ether, 12mmol) dropwise at 00C under a N2 atmosphere. The mixture was stirred for another hr at 00C, then brought to ambient temperature and stirred overnight. Saturated NH4Cl solution was added and extracted with ether for three times. The combined ether was dried over MgS 04 and concentrated in vacuo. The crude residue was separated by flash column chromatography (CH2Cl2 to 5percent CH3OH/CH2C12) to give 56 as white solid (1.58g, 95percent). 1H-NMR (360 MHz, CDCl3) δ 2.20-2.16 (m, 2H), 1.89-1.75 (m, 6H), 1.68 (br s, 4H), 1.57-1.54 (m, 2H), 1.48 (br s, IH), 1.35 (s, 3H); 13C-NMR (90 MHz, CDCl3) δ 74.06, 39.30, 38.49, 35.33, 33.16, 27.73, 27.60. 27.22; ESI-MS: Calculated for C11Hi8O (M +H)+ 167.3, Found: 167.3.
Reference: [1] Patent: WO2011/22191, 2011, A1, . Location in patent: Page/Page column 34
[2] J. Gen. Chem. USSR (Engl. Transl.), 1987, vol. 57, p. 147 - 150[3] Zhurnal Obshchei Khimii, 1987, vol. 57, # 1, p. 171 - 174
[4] Journal of the American Chemical Society, 1968, vol. 90, # 18, p. 4929 - 4939
[5] Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 1981, vol. 37, p. 129 - 134
[6] Tetrahedron, 2000, vol. 56, # 37, p. 7237 - 7243
[7] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4629 - 4639
[8] Patent: WO2015/35234, 2015, A2, . Location in patent: Page/Page column 40; 41
[9] Patent: WO2018/57973, 2018, A1, . Location in patent: Paragraph 0534
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YieldReaction ConditionsOperation in experiment
80% With methylmagnesium bromide In tetrahydrofuran; diethyl ether; hexane; dichloromethane a.
Synthesis of 2-methyl-2-adamantanol
110 ml of a solution of methyl magnesium bromide (3.0 M) in diethyl ether was diluted with 100 ml of anhydrous tetrahydrofuran (THF).
Then, the solution wasput into a 1 litre flask and then maintained at 0°C. 2-adamantanone (45 g, 0.3 mol) was dropped slowly using a dropping funnel and then the reaction was stirred at room temperature for about 12 hours.
After completion of the reaction, excess THF was removed using a rotary evaporator and then the resultant product was poured into water.
Then, the resultant product was neutralized with dilute sulfuric acid and extracted using diethyl ether and was then dried over magnesium sulfate.
The obtained crude product was recrystallized using n-hexane and a methylene chloride cosolvent to yield the desired product 2-methyl-2-adamantanol (yield: 80percent).
80% With methylmagnesium bromide In tetrahydrofuran; diethyl ether; hexane; dichloromethane a.
Synthesis of 2-methyl-2-adamantanol
110 ml of a solution of methyl magnesium bromide (3.0 M) in diethyl ether was diluted with 100 ml of anhydrous tetrahydrofuran (THF).
Then, the solution was put into a 1 liter flask and then maintained at 0° C. 2-adamantanone (45 g, 0.3 mol) was dropped slowly using a dropping funnel and then the reaction was stirred at room temperature for about 12 hours.
After completion of the reaction, excess THF was removed using a rotary evaporator and then the resultant product was poured into water.
Then, the resultant product was neutralized with dilute sulfuric acid and extracted using diethyl ether and was then dried over magnesium sulfate.
The obtained crude product was recrystallized using n-hexane and a methylene chloride cosolvent to yield the desired product 2-methyl-2-adamantanol (yield: 80percent).
Reference: [1] Patent: EP1125917, 2001, A1,
[2] Patent: US6222061, 2001, B1,
[3] Journal of Organic Chemistry, 1973, vol. 38, # 20, p. 3455 - 3459
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Reference: [1] Organic and Biomolecular Chemistry, 2010, vol. 8, # 7, p. 1551 - 1559
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2896 - 2902
[3] Journal of the American Chemical Society, 1975, vol. 97, # 9, p. 2408 - 2413
[4] Journal of the American Chemical Society, 1987, vol. 109, # 24, p. 7270 - 7276
[5] Tetrahedron, 2000, vol. 56, # 37, p. 7237 - 7243
[6] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6156 - 6160
[7] Journal of Organic Chemistry, 2012, vol. 77, # 3, p. 1340 - 1360
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  • [ 74-88-4 ]
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Reference: [1] Russian Journal of Organic Chemistry, 2005, vol. 41, # 9, p. 1286 - 1288
[2] Journal of the American Chemical Society, 1961, vol. 83, p. 182 - 187
[3] Tetrahedron, 2015, vol. 71, # 16, p. 2463 - 2481
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Reference: [1] Chemistry Letters, 2008, vol. 37, # 7, p. 800 - 801
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Reference: [1] Synthesis, 1996, # 9, p. 1127 - 1130
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Reference: [1] Patent: US4036977, 1977, A,
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  • [ 702-98-7 ]
Reference: [1] Synthetic Communications, 1983, vol. 13, # 1, p. 53 - 62
[2] Organic and Biomolecular Chemistry, 2010, vol. 8, # 7, p. 1551 - 1559
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Reference: [1] Tetrahedron, 2000, vol. 56, # 37, p. 7237 - 7243
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Reference: [1] Tetrahedron, 2000, vol. 56, # 37, p. 7237 - 7243
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 16, p. 3357 - 3359
[2] Journal of Organic Chemistry, 1981, vol. 46, # 16, p. 3357 - 3359
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YieldReaction ConditionsOperation in experiment
38% With oxygen In acetic acid tert-butyl ester at 100℃; for 96 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by a catalyst that vanadium (18 μmol) is supported on montmorillonite (i.e., a V/Mont. catalyst); the amount of adamantane employed was changed to 3 mmol; t-butyl acetate was employed as a solvent; and reaction was performed at 100° C. for 96 hours. The V/Mont. catalyst was formed through the catalyst preparation process described in Japanese Patent Application Laid-Open (kokai) No. 2004-2234. Specifically, the catalyst was obtained by adding an aqueous vanadium(III) chloride solution to montmorillonite (Kunipia F, product of Kunimine Industries Co., Ltd.), followed by ion exchange, filtration, washing with water, drying, and firing in air at 800° C.
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 17, p. 6749 - 6757
[2] Journal of the American Chemical Society, 2005, vol. 127, # 44, p. 15391 - 15393
[3] Tetrahedron Letters, 1999, vol. 40, # 11, p. 2165 - 2168
[4] Tetrahedron Letters, 1999, vol. 40, # 11, p. 2165 - 2168
[5] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[6] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4520 - 4526
[7] Tetrahedron Letters, 1996, vol. 37, # 28, p. 4993 - 4996
[8] Journal of the American Chemical Society, 1989, vol. 111, # 17, p. 6749 - 6757
[9] Journal of the American Chemical Society, 1992, vol. 114, # 26, p. 10660 - 10662
[10] Heterocycles, 1995, vol. 40, # 2, p. 867 - 904
[11] Journal of the American Chemical Society, 1989, vol. 111, # 17, p. 6749 - 6757
[12] Tetrahedron Letters, 1996, vol. 37, # 28, p. 4993 - 4996
[13] Journal of Organic Chemistry, 2000, vol. 65, # 26, p. 9186 - 9193
[14] Chemical Communications, 2001, # 2, p. 191 - 192
[15] Chemistry Letters, 2005, vol. 34, # 12, p. 1626 - 1627
[16] Journal of Organic Chemistry, 2000, vol. 65, # 26, p. 9186 - 9193
[17] Chemistry - A European Journal, 2006, vol. 12, # 12, p. 3401 - 3409
[18] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2258 - 2265
[19] Journal of the American Chemical Society, 2011, vol. 133, # 21, p. 8074 - 8077
[20] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
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YieldReaction ConditionsOperation in experiment
31.6% at 120℃; for 6 h; The procedure of Example 1 was repeated, except that the acetic acid serving as a solvent was replaced by propionic acid.
Example 7 The procedure of Example 6 was repeated, except that the amount of the catalyst was changed to 10 μmol.
Example 8 The procedure of Example 6 was repeated, except that the amount of the catalyst was changed to 1.3 μmol.
25.1% at 100℃; for 6 h; The procedure of Example 9 was repeated, except that methanesulfonic acid [CH3SO3H] was added in an amount of 0.004 mL.
23.2% at 100℃; for 6 h; The procedure of Example 9 was repeated, except that europium triflate [Eu(OTf)3] was added in an amount of 10 μmol.
21.7% at 110℃; for 6 h; The procedure of Example 6 was repeated, except that the amount of adamantane employed was changed to 5 mmol, and the catalyst was replaced by Co(acac)2.2H2O.
15.3% at 120℃; for 6 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by a vanadium oxide-TPP complex [VOTPP].
15.5% at 100℃; for 6 h; The procedure of Example 6 was repeated, except that the amount of adamantane employed was changed to 5 mmol, and the reaction temperature was changed to 100° C.

Reference: [1] Chemical Communications, 2018, vol. 54, # 50, p. 6772 - 6775
[2] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
[3] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[4] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[5] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[6] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
[7] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[8] Tetrahedron Letters, 1995, vol. 36, # 44, p. 8059 - 8062
[9] Journal of Catalysis, 2005, vol. 233, # 1, p. 81 - 89
[10] Chemistry Letters, 2005, vol. 34, # 11, p. 1486 - 1487
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YieldReaction ConditionsOperation in experiment
22.3% at 120℃; for 6 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by acetylacetonatovanadium [V(acac)3].
18% at 120℃; for 6 h; Adamantane (10 mmol, 1.36 g) and acetylacetonatovanadyl [VO(acac)2] (5 μmol, 1.3 mg) serving as a catalyst were dissolved in acetic acid (10 mL) placed in a three-neck flask, and oxygen (1 atm) was continuously blown into the flask at a flow rate of 10 mL/min under stirring with a stirrer, to thereby allow partial oxidation of adamantane (ADM) to proceed for six hours at 120° C. The resultant product was subjected to quantitative analysis by means of a gas chromatograph, and as a result, the product was found to contain 1-adamantanol (1-AdOH), 2-adamantanol (2-AdOH), 1,3-adamantanediol (1,3-(AdOH)2), acetic acid esters of them, and 2-adamantanone (2-Ad=O). In the case of this product, adamantane conversion, total yield, and turnover number (TON) were found to be 37.0percent, 25.8percent, and 517, respectively. The results are shown in Table 1. Table 1 also shows analysis results for the cases of the below-described Examples and Referential Examples. As used herein, the turnover number is obtained by use of the following equation: [amount (mol) of adamantane consumed through reaction/amount (mol) of active metal (e.g., vanadium or cobalt) contained in the employed catalyst]. The greater the turnover number, the higher the reaction rate.
Example 2 The procedure of Example 1 was repeated, except that the amount of adamantane employed was changed to 5 mmol.
10.1% at 120℃; for 6 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by ammonium metavanadate [NH4VO3].
Reference: [1] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
[2] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
[3] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
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Reference: [1] Applied Catalysis A: General, 2018, vol. 560, p. 171 - 184
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Reference: [1] Russian Journal of Organic Chemistry, 2009, vol. 45, # 8, p. 1137 - 1142
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Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
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Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
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  • [ 700-57-2 ]
  • [ 5001-18-3 ]
  • [ 22635-62-7 ]
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  • 35
  • [ 700-58-3 ]
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  • [ 700-58-3 ]
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  • [ 700-57-2 ]
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  • 39
  • [ 10467-10-4 ]
  • [ 700-58-3 ]
  • [ 75-03-6 ]
  • [ 700-57-2 ]
  • [ 14648-57-8 ]
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  • 40
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  • [ 20098-17-3 ]
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