Home Cart 0 Sign in  
X

[ CAS No. 281-23-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 281-23-2
Chemical Structure| 281-23-2
Chemical Structure| 281-23-2
Structure of 281-23-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 281-23-2 ]

Related Doc. of [ 281-23-2 ]

Alternatived Products of [ 281-23-2 ]

Product Details of [ 281-23-2 ]

CAS No. :281-23-2 MDL No. :MFCD00074719
Formula : C10H16 Boiling Point : -
Linear Structure Formula :(CH2)6(CH)4 InChI Key :ORILYTVJVMAKLC-UHFFFAOYSA-N
M.W : 136.23 Pubchem ID :9238
Synonyms :

Calculated chemistry of [ 281-23-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.84
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.45
Log Po/w (XLOGP3) : 4.24
Log Po/w (WLOGP) : 2.83
Log Po/w (MLOGP) : 4.43
Log Po/w (SILICOS-IT) : 2.73
Consensus Log Po/w : 3.34

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.36
Solubility : 0.06 mg/ml ; 0.000441 mol/l
Class : Soluble
Log S (Ali) : -3.95
Solubility : 0.0152 mg/ml ; 0.000112 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.7
Solubility : 2.75 mg/ml ; 0.0202 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.8

Safety of [ 281-23-2 ]

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

Application In Synthesis of [ 281-23-2 ]

* 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 [ 281-23-2 ]
  • Downstream synthetic route of [ 281-23-2 ]

[ 281-23-2 ] Synthesis Path-Upstream   1~60

  • 1
  • [ 75-35-4 ]
  • [ 281-23-2 ]
  • [ 4942-47-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1975, vol. 18, p. 713 - 721
  • 2
  • [ 75-35-4 ]
  • [ 281-23-2 ]
  • [ 17768-28-4 ]
  • [ 17768-36-4 ]
  • [ 4942-47-6 ]
Reference: [1] Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992, vol. 41, # 7.2, p. 1612 - 1615,1244 - 1246
[2] Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992, vol. 41, # 7.2, p. 1612 - 1615,1244 - 1246
[3] Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992, vol. 41, # 7.2, p. 1612 - 1615,1244 - 1246
  • 3
  • [ 281-23-2 ]
  • [ 39751-07-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 947 - 956
  • 4
  • [ 281-23-2 ]
  • [ 74-88-4 ]
  • [ 702-79-4 ]
  • [ 768-91-2 ]
Reference: [1] Petroleum Chemistry, 2006, vol. 46, # 3, p. 159 - 163
  • 5
  • [ 876-53-9 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 768-91-2 ]
Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
  • 6
  • [ 768-90-1 ]
  • [ 75-76-3 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 768-91-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 7, p. 1203 - 1208[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 7, p. 1357 - 1363
[3] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 7, p. 1203 - 1208[4] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 7, p. 1357 - 1363
  • 7
  • [ 75-76-3 ]
  • [ 935-56-8 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 768-91-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 7, p. 1203 - 1208[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 7, p. 1357 - 1363
[3] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 7, p. 1203 - 1208[4] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 7, p. 1357 - 1363
  • 8
  • [ 75-76-3 ]
  • [ 281-23-2 ]
  • [ 702-79-4 ]
  • [ 768-91-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
  • 9
  • [ 876-53-9 ]
  • [ 75-16-1 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 702-77-2 ]
Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
  • 10
  • [ 75-76-3 ]
  • [ 281-23-2 ]
  • [ 702-79-4 ]
  • [ 707-35-7 ]
  • [ 768-91-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
  • 11
  • [ 768-90-1 ]
  • [ 75-76-3 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 707-35-7 ]
  • [ 768-91-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
  • 12
  • [ 876-53-9 ]
  • [ 75-16-1 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 768-91-2 ]
Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
  • 13
  • [ 67-56-1 ]
  • [ 700-56-1 ]
  • [ 702-79-4 ]
  • [ 4045-44-7 ]
  • [ 281-23-2 ]
  • [ 700-12-9 ]
  • [ 87-85-4 ]
  • [ 768-91-2 ]
  • [ 108-88-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 44, p. 11564 - 11568[2] Angew. Chem., 2013, vol. 125, # 44, p. 11778 - 11782,5
  • 14
  • [ 75-76-3 ]
  • [ 768-95-6 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 1687-36-1 ]
  • [ 707-35-7 ]
  • [ 768-91-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
  • 15
  • [ 768-90-1 ]
  • [ 75-76-3 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 1687-36-1 ]
  • [ 707-35-7 ]
  • [ 768-91-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
  • 16
  • [ 75-76-3 ]
  • [ 935-56-8 ]
  • [ 702-79-4 ]
  • [ 281-23-2 ]
  • [ 1687-36-1 ]
  • [ 707-35-7 ]
  • [ 768-91-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
  • 17
  • [ 75-76-3 ]
  • [ 281-23-2 ]
  • [ 702-79-4 ]
  • [ 1687-36-1 ]
  • [ 707-35-7 ]
  • [ 768-91-2 ]
  • [ 2109-06-0 ]
  • [ 30904-21-3 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
  • 18
  • [ 281-23-2 ]
  • [ 876-53-9 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 481 - 483[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 3, p. 540 - 542
[3] Dalton Transactions, 2014, vol. 43, # 22, p. 8530 - 8542
[4] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[5] Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 2, p. 339 - 345
[6] Journal of Organic Chemistry, 1998, vol. 63, # 14, p. 4581 - 4586
[7] MedChemComm, 2017, vol. 8, # 1, p. 135 - 147
[8] Journal of the American Chemical Society, 1993, vol. 115, # 16, p. 7293 - 7299
[9] Asian Journal of Chemistry, 2012, vol. 24, # 4, p. 1756 - 1758
[10] Tetrahedron Letters, 2009, vol. 50, # 50, p. 6938 - 6940
[11] Chemische Berichte, 1960, vol. 93, p. 1366 - 1371
[12] Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2065 - 2071
[13] Synthetic Communications, 2006, vol. 36, # 15, p. 2113 - 2119
[14] Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2177 - 2194
[15] Patent: US2004/127715, 2004, A1, . Location in patent: Page 11
  • 19
  • [ 281-23-2 ]
  • [ 768-90-1 ]
  • [ 876-53-9 ]
YieldReaction ConditionsOperation in experiment
99% Sealed tube; Inert atmosphere General procedure: The reactions were carried out in glass ampoules (20 mL) or in a pressure microreactor of stainless steel (17 mL). The results of parallel experiments were identical. Into the microreactor (ampoule) in an argon atmosphere was charged 0.3 mmol of Fe(acac)3, 10 mmol of initial adamantane, 10 mmol of CBr4, and 150 mmol of CH2Br2. The reactor was hermetically closed (the ampoule was sealed) and heated while stirring. On the completion of the reaction the reactor (ampoule) was cooled to room temperature, opened, the solvent was distilled off, the residue was crystallized from hexane or ethanol. Yields are given in respect to converted adamantane (adamantine derivatives) (GLC procedure, internal reference decene; correction factor for adamantane 1.09, for bromoadamantane 1.53). The structure of compounds obtained was proved by comparison with known samples and published data.
Reference: [1] Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187[2] Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199
[3] Tetrahedron Letters, 1986, vol. 27, # 12, p. 1399 - 1402
[4] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2041[5] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 10, p. 2239 - 2240
  • 20
  • [ 281-23-2 ]
  • [ 768-90-1 ]
  • [ 7314-85-4 ]
  • [ 876-53-9 ]
YieldReaction ConditionsOperation in experiment
35 %Spectr. With tert-butyl hypobromite; carbon tetrabromide In dichloromethane at 40℃; for 90 h; Darkness tert-Butyl hypobromite 50 (0.33 mL, freshly prepared and used immediately, 0.05 mmol, 0.1 eq.), adamantane 18 (68 mg, 0.5 mmol), carbon tetrabromide (166 mg, 0.5 mmol, 1 eq.) and dichloromethane (3.13 mL) were added to an oven-dried pressure tube and the reaction mixture was stirred at 40 °C for 90 h in the dark. The reaction mixture was cooled to RT and quenched with aqueous hydrochloric acid (1 M, 5 mL) and extracted with dichloromethane (4 x 10 mL). The organic phases were combined, dried over Na2SO4, filtered and concentrated in vacuo. The yield of adamantane 18 (29percent), 1-bromoadamantane 31 (35percent), 2-bromoadamantane 51 (14percent) and 1,3-bromoadamantane 52 (11percent) were determined by adding 1,3,5-trimethoxybenzene to the crude mixture as an internal standard for 1H-NMR.
Reference: [1] Molecules, 2018, vol. 23, # 5,
  • 21
  • [ 935-56-8 ]
  • [ 768-90-1 ]
  • [ 7314-85-4 ]
  • [ 281-23-2 ]
  • [ 876-53-9 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1987, # 13, p. 1013 - 1014
[2] Journal of the Chemical Society, Chemical Communications, 1987, # 13, p. 1013 - 1014
  • 22
  • [ 281-23-2 ]
  • [ 876-53-9 ]
  • [ 52918-86-2 ]
  • [ 33803-54-2 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991, vol. 40, # 12, p. 2528 - 2529[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991, vol. 40, # 12, p. 2897 - 2898
  • 23
  • [ 281-23-2 ]
  • [ 122-59-8 ]
  • [ 700-57-2 ]
  • [ 52804-26-9 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 9, p. 1672 - 1675[2] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 9, p. 1882 - 1886
  • 24
  • [ 281-23-2 ]
  • [ 700-58-3 ]
  • [ 768-95-6 ]
  • [ 5001-18-3 ]
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
  • 25
  • [ 281-23-2 ]
  • [ 768-95-6 ]
  • [ 5001-18-3 ]
YieldReaction ConditionsOperation in experiment
25% at 75℃; for 6 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by NHPI (1 mmol) and VO(acac)2 (50 μmol); the amount of acetic acid serving as a solvent was changed to 25 mL; and the reaction temperature was changed to 75° C.
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
[2] Journal of the American Chemical Society, 2002, vol. 124, # 47, p. 13978 - 13979
[3] Organic Letters, 2014, vol. 16, # 24, p. 6504 - 6507
[4] Tetrahedron Letters, 1999, vol. 40, # 11, p. 2165 - 2168
[5] Synthetic Communications, 1996, vol. 26, # 8, p. 1555 - 1562
[6] Chemical Communications, 2004, # 7, p. 798 - 799
[7] Chemistry - A European Journal, 2015, vol. 21, # 44, p. 15564 - 15569
[8] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[9] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
[10] Journal of the American Chemical Society, 1996, vol. 118, # 37, p. 8961 - 8962
[11] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
[12] Journal of the American Chemical Society, 1992, vol. 114, # 4, p. 1346 - 1351
[13] Organic Letters, 2005, vol. 7, # 2, p. 263 - 266
[14] Patent: US6403521, 2002, B1,
[15] Organic and Biomolecular Chemistry, 2012, vol. 10, # 15, p. 3122 - 3130
[16] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
[17] RSC Advances, 2016, vol. 6, # 96, p. 93756 - 93767
[18] Chemistry - An Asian Journal, 2018, vol. 13, # 17, p. 2458 - 2464
  • 26
  • [ 281-23-2 ]
  • [ 700-58-3 ]
  • [ 768-95-6 ]
  • [ 700-57-2 ]
  • [ 5001-18-3 ]
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
  • 27
  • [ 281-23-2 ]
  • [ 5001-18-3 ]
YieldReaction ConditionsOperation in experiment
71% at 80℃; for 2 h; Firstly, to a solution of adamantane (2.59g, 19mmol) in a mixture of acetic acid (100mL) and concentrated sulphuric acid (0.52mL 9.5mmol) was slowly added chromium trioxide (7.6g, 76mmol). The resultant reaction system was stirred at 80°C for 2h. Then the mixture was concentrated, washed with 30percent NaOH solution, and extracted with ethyl acetate. The organic extract was cooled down at room temperature overnight to give a white precipitate which was recrystallized from a mixed solvent of ethanol and hexane to afford white solid 1. 1H NMR (300MHz, DMSO-d6): δ 1.360–1.476 (m, 12H), 2.104 (s, 2H), 4.390 (s, 2H).
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 2, p. 367 - 369
[2] Tetrahedron Letters, 1996, vol. 37, # 28, p. 4993 - 4996
[3] Chemische Berichte, 1960, vol. 93, p. 1366 - 1371
[4] Patent: US7078562, 2006, B2, . Location in patent: Page/Page column 16-17; 19-20
[5] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2258 - 2265
[6] MedChemComm, 2017, vol. 8, # 1, p. 135 - 147
  • 28
  • [ 281-23-2 ]
  • [ 5001-18-3 ]
  • [ 99181-50-7 ]
Reference: [1] Patent: US2002/40170, 2002, A1,
[2] Patent: US2002/40170, 2002, A1,
[3] Patent: US2002/40170, 2002, A1,
[4] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
[5] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
  • 29
  • [ 281-23-2 ]
  • [ 111-27-3 ]
  • [ 5001-18-3 ]
  • [ 99181-50-7 ]
YieldReaction ConditionsOperation in experiment
70% With hydrogenchloride; sodium hydroxide; sodium hypochlorite In water; ethyl acetate EXAMPLE 1
Into a 10-L five-necked jacketed flask equipped with a stirring device, a thermometer, a Dimroth condenser and a pH electrode, were charged 408 g (3 mol) of adamantane, 3000 mL of ethyl acetate, 20 g of ruthenium chloride n-hydrate (corresponding to 82 mmol of dihydrate) and 500 g of water.
After heating to 46° C, the pH was adjusted to 4.
Then, a 12percent aqueous solution of sodium hypochlorite was started to be added dropwise.
The dropping speed was regulated so as to add 4120 g (7.5 mol) of the aqueous solution of sodium hypochlorite over 400 min as calculated from the reaction rate previously measured.
The content of the free alkali in the aqueous solution of sodium hypochlorite was 0.5percent.
The reaction was continued by maintaining the pH of the reaction system at 4.0 to 4.5 by adding a 5percent hydrochloric acid in an amount equivalent to the free alkali in the aqueous solution of sodium hypochlorite.
During the reaction, the hypochlorite concentration in the water phase varied between 0.03 and 0.09 mmol/g.
After the addition of the sodium hypochlorite was completed, 80 g of a 25 wt percent NaOH aqueous solution and 3000 mL of hexanol were added to separate the reaction mixture into the organic phase and the water phase.
The gas chromatographic analysis on each phase showed that the conversion of adamantane was 100percent, the yield of 1-adanantanol was 9percent, the yield of 1,3-adamantanediol was 70percent, and the yield of 1,3,5-adamantanetriol was 14percent.
The ruthenium catalyst was recovered as black precipitates by filtering the water phase.
Reference: [1] Patent: US2002/40170, 2002, A1,
  • 30
  • [ 281-23-2 ]
  • [ 111-27-3 ]
  • [ 5001-18-3 ]
  • [ 99181-50-7 ]
Reference: [1] Patent: US2002/40170, 2002, A1,
  • 31
  • [ 281-23-2 ]
  • [ 768-95-6 ]
  • [ 5001-18-3 ]
  • [ 99181-50-7 ]
Reference: [1] Patent: EP1191010, 2002, A2, . Location in patent: Page column 5-7
[2] Synthetic Communications, 2013, vol. 43, # 8, p. 1161 - 1167
  • 32
  • [ 281-23-2 ]
  • [ 64-19-7 ]
  • [ 700-58-3 ]
  • [ 19066-22-9 ]
  • [ 768-95-6 ]
  • [ 700-57-2 ]
  • [ 5001-18-3 ]
  • [ 22635-62-7 ]
  • [ 56137-59-8 ]
  • [ 29817-47-8 ]
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
  • 33
  • [ 281-23-2 ]
  • [ 700-57-2 ]
  • [ 5001-18-3 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 15, p. 1677 - 1680
  • 34
  • [ 281-23-2 ]
  • [ 75-05-8 ]
  • [ 700-58-3 ]
  • [ 768-95-6 ]
  • [ 700-57-2 ]
  • [ 5001-18-3 ]
  • [ 880-52-4 ]
Reference: [1] Applied Catalysis A: General, 2018, vol. 560, p. 171 - 184
  • 35
  • [ 281-23-2 ]
  • [ 700-58-3 ]
  • [ 768-95-6 ]
  • [ 5001-18-3 ]
  • [ 772-26-9 ]
Reference: [1] Russian Journal of Organic Chemistry, 2009, vol. 45, # 8, p. 1137 - 1142
  • 36
  • [ 281-23-2 ]
  • [ 700-58-3 ]
  • [ 5001-18-3 ]
  • [ 99181-50-7 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
  • 37
  • [ 281-23-2 ]
  • [ 700-58-3 ]
  • [ 768-95-6 ]
  • [ 5001-18-3 ]
  • [ 99181-50-7 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
  • 38
  • [ 281-23-2 ]
  • [ 768-95-6 ]
  • [ 700-57-2 ]
  • [ 5001-18-3 ]
Reference: [1] Catalysis Today, 2012, vol. 185, # 1, p. 157 - 161
[2] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
  • 39
  • [ 281-23-2 ]
  • [ 7575-82-8 ]
  • [ 5001-18-3 ]
Reference: [1] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 971 - 976[2] Zh. Org. Khim., 2017, vol. 53, # 7, p. 959 - 964,5
  • 40
  • [ 281-23-2 ]
  • [ 768-95-6 ]
  • [ 33388-08-8 ]
  • [ 5001-18-3 ]
Reference: [1] Russian Journal of Organic Chemistry, 2007, vol. 43, # 4, p. 623 - 624
  • 41
  • [ 281-23-2 ]
  • [ 74087-85-7 ]
  • [ 700-58-3 ]
  • [ 768-95-6 ]
  • [ 700-57-2 ]
  • [ 5001-18-3 ]
  • [ 22635-62-7 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 2, p. 249 - 252
  • 42
  • [ 281-23-2 ]
  • [ 768-90-1 ]
  • [ 768-95-6 ]
  • [ 33388-08-8 ]
  • [ 5001-18-3 ]
Reference: [1] Russian Journal of Organic Chemistry, 2007, vol. 43, # 4, p. 623 - 624
  • 43
  • [ 281-23-2 ]
  • [ 768-95-6 ]
  • [ 5001-18-3 ]
  • [ 700-57-2 ]
  • [ 20098-16-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1996, # 9, p. 1811 - 1820
  • 44
  • [ 281-23-2 ]
  • [ 115464-59-0 ]
  • [ 768-95-6 ]
  • [ 5001-18-3 ]
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
  • 45
  • [ 281-23-2 ]
  • [ 74087-85-7 ]
  • [ 768-95-6 ]
  • [ 5001-18-3 ]
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
  • 46
  • [ 281-23-2 ]
  • [ 707-34-6 ]
YieldReaction ConditionsOperation in experiment
250 g at 45 - 65℃; Step one, equipped with a condenser, a thermometer and a tail gas absorption 5L four reaction flask, 108g of iron powder was added slowly dropwise over anhydrous bromine 400ml, about half an hour dropwise, stirred for 30 minutes after completion; document.write(""); Step two, the remaining bromine was added dropwise to the reaction flask. After completion, was heated to 45-50 deg.] C, 600g adamantane slowly added to the reaction system, the reaction temperature was raised to 62-65 deg.] C to reflux. The reaction to 65 hours have small sample measured GC showed starting material consumed. (In the control 1) document.write(""); Wherein the molar ratio of adamantane, anhydrous bromine, iron powder is 1: 10.6: 0.44.document.write(""); Step III After completion of the reaction, the recovered bromine atmospheric distillation, and the reaction mixture was poured into ice containing 3.5L bucket chloroform, stirred 10min, filtered through celite pad.document.write(""); Step four, the filtrate was washed with a saturated aqueous solution of sodium bisulfite and excess bromine (note cooled) solid sodium bisulfite consumption 5kg. document.write(""); Fifth, the organic layer was washed organic layer with water 3kg * 2 step was concentrated to dryness to give a crude product 1.95kg. document.write(""); Step six, 13L with methanol, heated and melted, add 65g active carbon, filtered hot, the filtrate was stirred for crystallization (cooling with ice). And filtered to give 1.19kg quality, the mother liquor was concentrated to about one-third of the original volume and stirred for crystallization, and filtered to give 250g white fine.
Reference: [1] Chemische Berichte, 1960, vol. 93, p. 1366 - 1371
[2] Journal of Organic Chemistry, 2004, vol. 69, # 4, p. 1010 - 1019
[3] Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1450 - 1455
[4] Journal of Organic Chemistry, 2014, vol. 79, # 14, p. 6738 - 6742
[5] Patent: CN104628526, 2016, B, . Location in patent: Paragraph 0069-0075
  • 47
  • [ 281-23-2 ]
  • [ 707-34-6 ]
  • [ 67422-73-5 ]
  • [ 67396-54-7 ]
  • [ 34059-96-6 ]
  • [ 106578-84-1 ]
  • [ 106578-85-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 481 - 483[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 3, p. 540 - 542
  • 48
  • [ 281-23-2 ]
  • [ 935-56-8 ]
  • [ 7346-41-0 ]
  • [ 1128-76-3 ]
  • [ 121-44-8 ]
Reference: [1] Chemistry Letters, 1998, # 11, p. 1085 - 1086
  • 49
  • [ 201230-82-2 ]
  • [ 281-23-2 ]
  • [ 39269-10-8 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With Al2Br7(1-)*CBr3(1+) In 1,2-dibromomethane at 0℃; for 3 h;
Stage #2: With water In 1,2-dibromomethaneCooling
At room temperature, CBr4*2AlBr3 was prepared by stirring CBr4 with AlBr3 in a molar ratio of 1-2 in anhydrous CH2Br2. Next, at 0 °C under atmospheric CO pressure, AdH (1) (1.43 mmol) was added to the freshly prepared CBr4*2AlBr3 (2.87 mmol) in CH2Br2 (3 mL). The mixture was stirred for 3 h. Then at atmospheric CO pressure, H2O (15 mL) was added carefully with cooling. The reaction mixture was kept for 1-2 d until the precipitation of 1,3-Ad(COOH)2 was complete. The Ad(COOH)2 was filtered, washed with H2O, dried, and crystallized from AcOH. The yield of analytically pure compound was 80percent with respect to 1. Mp 285-286 °C. Calcd. for C12H16O4, (percent): C, 64.27; H, 7.19. Found (percent): C, 64.21; H, 7.24.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 27, p. 3493 - 3496
[2] Journal of Organic Chemistry, 1998, vol. 63, # 2, p. 222 - 223
[3] Journal of Organic Chemistry, 1978, vol. 43, p. 4978 - 4980
  • 50
  • [ 64-18-6 ]
  • [ 281-23-2 ]
  • [ 39269-10-8 ]
Reference: [1] Chemische Berichte, 1994, vol. 127, # 10, p. 2081 - 2088
[2] Synthetic Communications, 1984, vol. 14, # 2, p. 113 - 120
[3] Chemische Berichte, 1991, vol. 124, # 4, p. 915 - 922
  • 51
  • [ 201230-82-2 ]
  • [ 281-23-2 ]
  • [ 768-95-6 ]
  • [ 828-51-3 ]
  • [ 15897-81-1 ]
  • [ 39269-10-8 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 2, p. 222 - 223
  • 52
  • [ 281-23-2 ]
  • [ 39269-10-8 ]
Reference: [1] Chemische Berichte, 1960, vol. 93, p. 1366 - 1371
[2] MedChemComm, 2017, vol. 8, # 1, p. 135 - 147
  • 53
  • [ 281-23-2 ]
  • [ 103-84-4 ]
  • [ 700-57-2 ]
  • [ 1459-50-3 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 9, p. 1672 - 1675[2] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 9, p. 1882 - 1886
  • 54
  • [ 75-35-4 ]
  • [ 281-23-2 ]
  • [ 17768-28-4 ]
  • [ 17768-36-4 ]
  • [ 4942-47-6 ]
Reference: [1] Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992, vol. 41, # 7.2, p. 1244 - 1246[2] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1992, # 7, p. 1612 - 1615
[3] Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992, vol. 41, # 7.2, p. 1244 - 1246[4] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1992, # 7, p. 1612 - 1615
[5] Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992, vol. 41, # 7.2, p. 1244 - 1246[6] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1992, # 7, p. 1612 - 1615
  • 55
  • [ 281-23-2 ]
  • [ 26562-81-2 ]
Reference: [1] Russian Journal of Organic Chemistry, 2017, vol. 53, # 8, p. 1170 - 1175[2] Zh. Org. Khim., 2017, vol. 53, # 8, p. 1156 - 1161,6
  • 56
  • [ 281-23-2 ]
  • [ 665-66-7 ]
Reference: [1] Russian Journal of Organic Chemistry, 2015, vol. 51, # 12, p. 1703 - 1709[2] Zh. Org. Khim., 2015, vol. 51, # 12, p. 1737 - 1743,7
  • 57
  • [ 281-23-2 ]
  • [ 131211-27-3 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1990, vol. 60, # 8.1, p. 1603 - 1606[2] Zhurnal Obshchei Khimii, 1990, vol. 60, # 8, p. 1795 - 1799
[3] Patent: US9802185, 2017, B2,
  • 58
  • [ 281-23-2 ]
  • [ 157282-19-4 ]
Reference: [1] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 6, p. 801 - 811
[2] Patent: US9802185, 2017, B2,
  • 59
  • [ 1707-40-0 ]
  • [ 912361-56-9 ]
  • [ 281-23-2 ]
  • [ 6600-42-6 ]
  • [ 1660-04-4 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4362 - 4365
  • 60
  • [ 1041846-07-4 ]
  • [ 912361-56-9 ]
  • [ 281-23-2 ]
  • [ 1660-04-4 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4362 - 4365
Recommend Products
Same Skeleton Products
Historical Records