[ CAS No. 6240-11-5 ] {[proInfo.proName]}

Name: 6240-11-5|1-Adamantaneethanol|98%
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SKU: A981370
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Quality Control of [ 6240-11-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6240-11-5 ]

SDS Specification

Alternatived Products of [ 6240-11-5 ]

Product Details of [ 6240-11-5 ]

CAS No. :	6240-11-5	MDL No. :	MFCD00074756
Formula :	C₁₂H₂₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZBIDZPHRNBZTLT-UHFFFAOYSA-N
M.W :	180.29	Pubchem ID :	110810
Synonyms :

Calculated chemistry of [ 6240-11-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.36
TPSA :	20.23 Å²

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) :	-5.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.46
Log Po/w (XLOGP3) :	3.36
Log Po/w (WLOGP) :	2.59
Log Po/w (MLOGP) :	3.02
Log Po/w (SILICOS-IT) :	2.78
Consensus Log Po/w :	2.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.94
Solubility :	0.206 mg/ml ; 0.00114 mol/l
Class :	Soluble
Log S (Ali) :	-3.46
Solubility :	0.0621 mg/ml ; 0.000345 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.18
Solubility :	1.19 mg/ml ; 0.00662 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.89

Safety of [ 6240-11-5 ]

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 [ 6240-11-5 ]

* 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.

Downstream synthetic route of [ 6240-11-5 ]

[ 6240-11-5 ] Synthesis Path-Downstream 1~109

1
[ 6240-11-5 ]
[ 773-37-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sulfuric acid; hydrogen bromide; In water; for 6h;Reflux; Cooling with ice;	In a 1 L round bottom flask equipped with a reflux condenser, 126.20 g (0.70 mol) of 2- (1-adamantyl) ethanol was added while 164 g of concentrated sulfuric acid and 200 g (48% aqueous solution) of hydrobromic acid were cooled in an ice bath, . The mixture was refluxed for 6 hours, cooled to room temperature and then added to 400 g of ice. The aqueous phase was extracted with 400 ml of pentane. The organic phase was washed with 2 M NaOH solution and water, dried over magnesium sulfate and the solvent was removed in vacuo. The product was distilled in vacuo to give 153.2 g (90%) of (1- (2-bromo-ethyl) -adamantane as a colorless oil.
		Halide 24: 2-(1-Adamantyl)ethyl bromide Using the procedure described in Can. J. Chem., 46, 86, (1968), this bromide was obtained from 2-(1-adamantyl)ethanol (Aldrich) by the conversion of the hydroxyl group to the bromide by carbon tetrabromide with the presence of triphenylphosphine.
		Halide 24: 2-(1 -Adamantyl)ethyl bromide Using the procedure described in Can. J. Chem., 46, 86 (1968), this bromide was obtained from 2-(1-adamantyl)ethanol (Aldrich) by the conversion of the hydroxyl group to the bromide by CBr4 and triphenylphosphine.

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 8720 - 8731
[2]Patent: JP6196581,2017,B2 .Location in patent: Paragraph 0198
[3]Journal of Medicinal Chemistry,1995,vol. 38,p. 443 - 452
[4]New Journal of Chemistry,2020,vol. 44,p. 7071 - 7079
[5]Journal of medicinal chemistry,1972,vol. 15,p. 1313 - 1321
[6]Patent: US5202321,1993,A
[7]Patent: US5314900,1994,A
[8]Patent: US6335343,2002,B1 .Location in patent: Page column 65
[9]Synthetic Communications,2013,vol. 43,p. 1772 - 1777
[10]Supramolecular Chemistry,2015,vol. 27,p. 364 - 371
[11]Russian Journal of Organic Chemistry,2018,vol. 54,p. 996 - 1002
Zh. Org. Khim.,2018,vol. 54,p. 994 - 1000,7

2
[ 358-23-6 ]
[ 6240-11-5 ]
[ 133807-78-0 ]
[ 133825-26-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 97 - 108

3
[ 6240-11-5 ]
[ 3223-20-9 ]
[ 155388-70-8 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 845 - 859

4
[ 6240-11-5 ]
[ 114652-98-1 ]
[ 114653-00-8 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1651 - 1656

5
[ 6240-11-5 ]
[ 18220-83-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 4h;	Example 6 <n="97"/>Synthesis of Compound 902To a solution of compound 901 (2.00 g, 11.1 mmol) in dichloromethane (30 niL) was added Dess-Martin periodinane (5.59 g, 153 mmol), and the mixture was stirred at room temperature for 4 hrs. After completion of the reaction, the reaction mixture was diluted with DCM, washed with water followed by brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford compound 902 (1.8 g, 91%). 1H NMR (200 MHz, CDCl3): delta 9.6 (s, IH), 2.57 (s, 2H), 1.6-2.0 (m, 15H).
90%	With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; In dichloromethane; water; for 0.333333h;pH 8.6;Cooling with ice;	General procedure: (1-Adamantyl)methanol (3.0 g, 18 mmol), KBr (214 mg, 1.8 mmol) and TEMPO (28 mg, 0.18 mmol)2 were dissolved in DCM (50 mL). The solution was cooled in an icebath. A commercial 5 % bleach-solution (30 mL) was buffered to pH 8.6 using solid NaHCO3 and then added to the TEMPOsolution. After 20 min of rapid stirring, the layers were separated. The DCM layer was dried over Na2SO4, filtered and concentrated in vacuo. This affords the product as a white to light-orange solid (2.25 g, 74%)
79%	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃;	1-Adamantaneethanol (1.0 gram, 5.6 mmol, Sigma, 188115) was dissolved in DCM (15 mL). To the solution was added Dess-Martin periodinane (5.0 mL) at 0 C. After being stirred overnight at room temperature, the mixture was purified by ISCO to afford intermediate 6 (780 mg, 79%). 1H NMR (600 MHz, CDCb) delta 9.86 (t, J= 3.2 Hz, 1H), 2.12 (d, J = 3.2 Hz, 2H), 1.98 (brs, 3H), 1.67 - 1.64 (m, 12H). Intermediate 3 (100 mg, 0.16 mmol) and intermediate 6 (35 mg, 0.20 mmol) were dissolved in DCM (3.0 mL), and methanol (3.0 mL). To the solution was added sodium triacetoxyborohydride (55 mg, 0.26 mmol) at 0 C. After being stirred overnight at room temperature, the mixture was filtered and purified by preparative HPLC to afford AM16-91 A as yellow solid in TFA salt form (99 mg, 80%). 1H NMR (600 MHz, CD3OD) delta 8.53 (brs, 1H), 8.37 (s, 1H), 8.12 - 8.02 (m, 1H), 7.93 (s, 1H), 7.76 (s, 1H), 7.03 (d, J= 8.7 Hz, 1H), 6.14 (s, 1H), 5.11 - 5.03 (m, 1H), 4.57 (s, 2H), 4.49 (brs, 2H), 3.69 (brs, 2H), 3.34 - 3.03 (m, 6H), 2.42 (s, 3H), 2.24 (s, 3H), 1.96 (brs, 3H), 1.79 - 1.73 (m, 3H), 1.70 - 1.65 (m, 3H), 1.59 - 1.54 (m, 14H).

64%	In ethyl acetate; at 45℃; for 10h;Inert atmosphere; Irradiation;	General procedure: To a three-necked, cylindrical Pyrex glass reaction vessel equipped with a rubber balloon, rubberseptum, and glass stopper, a N2 atmosphere was introduced by flowing via cannula for 5 min. Au(0.6 wt %)/TiO2 (117.3 mg, 0.17 mol % Au), 1a (271.5 mg, 1.99 mmol), and dehydrated ethylacetate (25 mL) were added successively to the vessel. After N2 gas was reintroduced more than 5min, the rubber balloon was connected to the vessel and the mixture was sonicated. The vessel wasimmersed in a oil bath (kept at 45 oC) and stirred for 10 h under irradiation (lambda = 300-470 nm). 1HNMR analysis of this crude mixture using mesitylene as an internal standard indicated 97%conversion of 1a and the formation of 2a in 86% yield, as determined based on the signals at delta 3.61ppm and 2.94 ppm (shifted from 2.89 ppm due to the presence of ethyl acetate), respectively. Theproduct was purified by silica gel column chromatography (n-hexane/ethyl acetate 3:1) to afford 2a(180 mg, 66% yield, with inclusion of small amounts of unidentified impurities).
	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; for 1h;	Adamantyl acetaldehyde: To a flask containing 2-adamantyl-1-ethanol (5 g, 27.7 mmol) in CH2Cl2 (28 mL) was added TEMPO (433 mg, 2.77 mmol) followed by iodobenzene diacetate (9.8 g, 30.5 mmol). The reaction was stirred 1 hour and then diluted with CH2Cl2 (100 mL). Saturated aqueous solution of Na2S2O3 (100 mL) was added and extracted with CH2Cl2 (3×50 mL). The combined organics were washed with saturated aqueous NaHCO3 (150 mL) and brine (150 mL), dried over Na2SO4, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (5% Et2O/pentanes) to provide the title compound, which was identical to the reported literature compound (see Luly et al. (1987) J. Org. Chem. 52: 1487).
		General Procedure: To a dry 25 ml 3-neck round bottom flask equipped with magnetic stirring bar, thermometer, Ar inlet, and dropping funnel was added dry dimethyl sulfoxide (4 mmol, 0.32g, 0.29 ml) diluted with dry DCM ((3 ml), and the solution was cooled bellow -60 C in dry ice-acetone bath. Then trifluoroacetic anhydride (3 mmol, 0.63 g, 0.42 ml), in 2 ml of dry DCM was added. After 10 min of efficient stirring 1-adamantane methanol (2 mmol, 0.33 g) in 2 ml of dry DCM was added dropwise. The rate of addition of alcohol was controlled to keep temperature bellow -60 C. Mixture was stirred for 20 min at -65 C, then ice bath was removed and mixture was allowed to warm up to room temperature. Next, triethylamine (0.8 ml) was added in portions during 10 minutes, and mixture was stirred for another 10 minutes. The reaction mixture was poured into separatory funnel and washed with diluted HCl, then with water, and combined aqueous fractions were extracted once with DCM. Organic fractions were combined, dried over sodium sulfate, and solvent was evaporated. Residue was dried in vacuum giving yellow solid (0.052 g).

Reference： [1]Patent: WO2008/73623,2008,A2 .Location in patent: Page/Page column 95; 96
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3384 - 3393
[3]Chemical Communications,2020,vol. 56,p. 5969 - 5972
[4]Journal of Organic Chemistry,1987,vol. 52,p. 1487 - 1492
[5]Organic Letters,2019,vol. 21,p. 3866 - 3870
[6]Patent: WO2018/81530,2018,A1 .Location in patent: Page/Page column 59
[7]Organic and Biomolecular Chemistry,2018,vol. 16,p. 2541 - 2548
[8]Chemistry Letters,2017,vol. 46,p. 580 - 582
[9]Helvetica Chimica Acta,1979,vol. 62,p. 956 - 964
[10]Journal of the American Chemical Society,2005,vol. 127,p. 8826 - 8828
[11]Patent: US2006/189830,2006,A1 .Location in patent: Page/Page column 8
[12]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1066 - 1070
[13]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2177 - 2182
[14]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5353 - 5357
[15]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2532 - 2537
[16]Journal of Medicinal Chemistry,2016,vol. 59,p. 6826 - 6837

6
[ 51849-10-6 ]
[ 6240-11-5 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 5404 - 5406

7
[ 6240-11-5 ]
[ 124-63-0 ]
[ 36949-72-1 ]

Yield	Reaction Conditions	Operation in experiment
96%		A solution of 1-adamantylethanol (3 g, 16.64 mmol) in methylen chloride (50 mL) and triethylamine (2.8 mL, 19.95 mmol) was stirred for 10 minutes. Then methanesulfonyl chloride (1.55 mL, 20.03 mmol) was added and the resulting reaction mixture was stirred at room temperature for 72 hours. The crude was partitioned between methylen chloride and a solution of sodium hydrogen carbonate (4%). The organic layer was washed with water and brine and the solvent was removed under reduced pressure to give the title compound as a yellow oil (4.1 g, 96%), which was used in the next step without further purification.

Reference： [1]Patent: WO2009/68177,2009,A1 .Location in patent: Page/Page column 34-35
[2]Journal of Organic Chemistry,1991,vol. 56,p. 7162 - 7167
[3]Chemistry - A European Journal,2018,vol. 24,p. 17225 - 17229

8
[ 6240-11-5 ]
[ 98-59-9 ]
[ 26831-48-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In dichloromethane; at 0 - 20℃;	To a solution of 1-adamantaneethanol (3.06 g, 16.9 mmol) and triethylamine (2.8 mL, 20.1 mmol) in methylen chloride (30 mL) was added at O0C a suspension of 4- methylbenzene-1-sulfonyl chloride (3.88 g, 20.3 mmol) in methylen chloride (40 mL). The reaction mixture was stirred at room temperature overnight. Then, ice and a solution of ammonia 50% in water were added into the reaction mixture. The mixture was extracted with pentane and the organic layer was washed with water and brine. The solvent was removed under reduced pressure and the title compound was obtained as an oil (5.4 g, 90%). MS (M+): 335.
89.4%	With pyridine; at 20℃;	1-Adamantaneethanol (4.80 g, 26.6 mmol) was dissolved in 25 mL of pyridine, cooled to 0 C on ice bath and p-toluenesulfonyl chloride (8.37 g, 43.9 mmol) was added to the solution. The reaction mixture was allowed to warm and stirred overnight at room temperature. The solvent was evaporated under reduced pressure and the product was redissolved in 100 mL of EtOAc. The organic layer was washed once with saturated NaHCO3 and twice with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The subsequent filtration through a silica pad (40 g, EtOAc/n-heptane = 1/25) yielded the final product as a white solid.
		Under ice bath, 7.0 g (37 mmol) of p-toluenesulfonyl chloride and 5.0 mL (37 mmol) of triethylamine were added to 40 mL of dichloromethane solution.After 10 min, 4.15 g (23 mmol) of adamantane ethanol was slowly added to the mixture.The temperature was controlled to not exceed 8 C. After 5 h of reaction, TLC was detected (petroleum ether: ethyl acetate = 25:1) until the reaction was completed, and 10 mL of dichloromethane was added.The reaction solution was poured into ice water (10 mL × 2), and the reaction was stirred for 15 min.Wash with 10% hydrochloric acid solution, saturated sodium bicarbonate, and saturated brine.The organic phase is dried over anhydrous sodium sulfate, filtered, and the filtrate is evaporated under reduced pressure.The residue is passed through a silica gel column.Compound adamantyl ethyl p-toluenesulfonate(J13),For the preparation of 13j.1.7 g (4.5 mmol) of 10 and 2.1 g (6.8 mmol) of cesium carbonate were added to 9 mL of N,N-dimethylformamide under an oil bath of 55 C for 13 min.1.97 g (5.9 mmol) of (J13) was added in an oil bath at 60 C.The reaction was stirred for 15 h, then brine was added and ethyl acetate was evaporated.The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated.The residue was subjected to silica gel column chromatography (dichloromethane:methanol = 20:1)2.34g of colorless viscous solid 13j, yield 73.2%.

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 51 - 56
[2]Patent: WO2009/68177,2009,A1 .Location in patent: Page/Page column 17
[3]Carbohydrate Polymers,2015,vol. 133,p. 473 - 481
[4]Journal of Medicinal Chemistry,2012,vol. 55,p. 9562 - 9575
[5]Journal of Medicinal Chemistry,2017,vol. 60,p. 9067 - 9089
[6]Patent: CN108285439,2018,A .Location in patent: Paragraph 0038; 0139-0142

9
[ 4942-47-6 ]
[ 6240-11-5 ]

Yield	Reaction Conditions	Operation in experiment
42%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 25℃; for 3h;	To a suspension of LiAlH4 (39 mg, 1.03 mmol) in dry THF (3.0 mL) cooled at 0 C, a solution of 2-(adamantan-1-yl)acetic acid (200 mg, 1.03 mmol) in dry THF (3.0 mL) was added. The reactionmixture was stirred for 3 hours at 25 C then water was added dropwise at 0 C and the resultingmixture was extracted with diethyl ether (2 x 10 mL). The organic layers were extracted and driedover anhydrous Na2SO4, filtered and evaporated to afford the title compound 14j as an amorphouswhite solid (42% yield). 1H NMR (300 MHz, CDCl3): delta 3.75 (t, 2H, J = 6.0 Hz), 1.98 (s, 2H), 1.82 - 1.56(m, 12H), 1.38 (t, 2H, J = 6.4 Hz).

Reference： [1]Chemical Communications,2020,vol. 56,p. 5969 - 5972
[2]Organic Letters,2019,vol. 21,p. 3866 - 3870
[3]Chemical Communications,2020,vol. 56,p. 3843 - 3846
[4]New Journal of Chemistry,2020,vol. 44,p. 7071 - 7079
[5]Bioorganic Chemistry,2019,vol. 89
[6]Bulletin of the Chemical Society of Japan,1968,vol. 41,p. 238 - 240
[7]Pharmaceutical Chemistry Journal,1992,vol. 26,p. 616 - 618
Khimiko-Farmatsevticheskii Zhurnal,1992,vol. 26,p. 58 - 59
[8]Synthetic Communications,2013,vol. 43,p. 1772 - 1777
[9]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2532 - 2537
[10]Chemistry - A European Journal,2018,vol. 24,p. 17225 - 17229

10
[ 6240-11-5 ]
[ 147-94-4 ]
[ 93604-99-0 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 171 - 177

11
[ 6240-11-5 ]
[ 201230-82-2 ]
adamantano[2,1-c]tetrahydro-2H-pyran-2-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1994,vol. 116,p. 5473 - 5474

12
[ 29817-45-6 ]
[ 6240-11-5 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7259 - 7266

13
[ 6240-11-5 ]
[ 32159-15-2 ]
[ 34375-86-5 ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 58 - 60

14
[ 75-15-0 ]
[ 6240-11-5 ]
[ 74-88-4 ]
[ 22516-02-5 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1969,vol. 5,p. 88 - 89
Zhurnal Organicheskoi Khimii,1969,vol. 5,p. 91 - 92

15
[ 6240-11-5 ]
[ 677-24-7 ]
bis-<2-(1-adamantyl)ethyl> phosphate [ No CAS ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 377 - 388

16
[ 1499-17-8 ]
[ 6240-11-5 ]
Phosphoric acid 2-adamantan-1-yl-ethyl ester 2-hydroxy-phenyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1977,vol. 310,p. 894 - 905

17
[ 6240-11-5 ]
[ 546-67-8 ]
[ 29817-45-6 ]

Reference： [1]Journal of the Chemical Society C: Organic,1970,p. 2124 - 2126

18
[ 6240-11-5 ]
[ 546-67-8 ]
[ 29817-46-7 ]

Reference： [1]Journal of the Chemical Society C: Organic,1970,p. 2124 - 2126

19
[ 6240-11-5 ]
[ 546-67-8 ]
[ 29978-85-6 ]

Reference： [1]Journal of the Chemical Society C: Organic,1970,p. 2124 - 2126

20
[ 6240-11-5 ]
[ 99-76-3 ]
[ 166663-32-7 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3271 - 3281

21
[ 6240-11-5 ]
[ 16937-99-8 ]
[ 184646-14-8 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4775 - 4782

22
[ 2018-66-8 ]
[ 6240-11-5 ]
[ 139143-48-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1782 - 1787

23
[ 6240-11-5 ]
[ 75014-39-0 ]

Reference： [1]ChemMedChem,2019,vol. 14,p. 147 - 168
[2]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 579 - 583
[3]Chemical Communications,2020,vol. 56,p. 3843 - 3846
[4]Soft Matter,2015,vol. 11,p. 6432 - 6443
[5]Patent: WO2006/44381,2006,A2 .Location in patent: Page/Page column 38
[6]Journal of Medicinal Chemistry,1998,vol. 41,p. 346 - 357

Yield	Reaction Conditions	Operation in experiment
76%		Example 1-11 Synthesis of Monomer 11 By following the same procedures as in Examples 1-1-1 to 1-1-3 aside from using 2-adamantylethanol instead of 2-adamantanol, 1-[(2-adamantyl)ethoxy]-2-methylpropyl methacrylate was produced (four step yield 76%).

26
[ 6240-11-5 ]
[ 74-88-4 ]
CS₂ [ No CAS ]
[ 22516-02-5 ]

Reference： [1]Helvetica Chimica Acta,1984,vol. 67,p. 2128 - 2142

27
[ 6240-11-5 ]
(2-acetyl-benzofuran-7-yl)-acetyl chloride [ No CAS ]
[ 273736-82-6 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1525 - 1532

28
[ 6240-11-5 ]
[ 2094-72-6 ]
adamantane-1-carboxylic acid 2-adamantan-1-yl-ethyl ester [ No CAS ]

Reference： [1]Russian Journal of Applied Chemistry,2003,vol. 76,p. 105 - 107

29
[ 75-44-5 ]
[ 6240-11-5 ]
[ 766546-16-1 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 6653 - 6656
[2]Journal of Organic Chemistry,2004,vol. 69,p. 8751 - 8757

30
[ 937-32-6 ]
[ 6240-11-5 ]
[ 316377-87-4 ]

Reference： [1]Synthesis,2004,p. 1671 - 1679

31
1-(2-benzyloxy-ethyl)-adamantane [ No CAS ]
[ 6240-11-5 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 7307 - 7309

32
[ 51694-22-5 ]
[ 6240-11-5 ]
[ 317835-34-0 ]

Reference： [1]Chemical Communications,2000,p. 2031 - 2032

33
[ 6240-11-5 ]
[ 1835-65-0 ]
[ 921206-56-6 ]

Reference： [1]Canadian Journal of Chemistry,2006,vol. 84,p. 1380 - 1387

34
[ 6240-11-5 ]
[ 71939-50-9 ]
C₂₇H₄₂O₅ [ No CAS ]
C₂₇H₄₂O₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7227 - 7233

35
[ 6240-11-5 ]
[ 10378-06-0 ]
[ 913816-31-6 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2005,vol. 31,p. 576 - 582

36
[ 136918-14-4 ]
[ 6240-11-5 ]
N-(2-adamantan-1-ylethyl)phthalimide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4898 - 4908
[2]European Journal of Medicinal Chemistry,2009,vol. 44,p. 303 - 311

37
[ 6240-11-5 ]
[ 6600-42-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1969,vol. 5,p. 88 - 89
Zhurnal Organicheskoi Khimii,1969,vol. 5,p. 91 - 92
[2]Helvetica Chimica Acta,1984,vol. 67,p. 2128 - 2142
[3]Synthetic Communications,2013,vol. 43,p. 1772 - 1777

38
[ 6240-11-5 ]
[ 770-69-4 ]

Reference： [1]Synlett,2012,vol. 23,p. 1235 - 1239
[2]Journal of Organic Chemistry USSR (English Translation),1969,vol. 5,p. 88 - 89
Zhurnal Organicheskoi Khimii,1969,vol. 5,p. 91 - 92
[3]Journal of Medicinal Chemistry,1982,vol. 25,p. 51 - 56

39
[ 6240-11-5 ]
[ 22516-04-7 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1969,vol. 5,p. 88 - 89
Zhurnal Organicheskoi Khimii,1969,vol. 5,p. 91 - 92

40
[ 6240-11-5 ]
[ 913816-39-4 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2005,vol. 31,p. 576 - 582

41
[ 6240-11-5 ]
[ 913816-35-0 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2005,vol. 31,p. 576 - 582

42
[ 6240-11-5 ]
[ 913816-43-0 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2005,vol. 31,p. 576 - 582

43
[ 6240-11-5 ]
2-[7-acetylamino-6-(2-adamantan-1-yl-ethoxy)-2,2-dimethyl-hexahydro-pyrano[3,2-<i>d</i>][1,3]dioxin-8-yloxy]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2005,vol. 31,p. 576 - 582

44
[ 6240-11-5 ]
O-[2-(adamant-1-yl)ethyl 2-acetamido-2,3-dideoxy-β-D-glucopyranos-3-yl]-D-lactoyl-L-alanyl-D-isoglutamine [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2005,vol. 31,p. 576 - 582

45
[ 6240-11-5 ]
[ 913816-47-4 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2005,vol. 31,p. 576 - 582

46
[ 6240-11-5 ]
4-(2-{2-[7-acetylamino-6-(2-adamantan-1-yl-ethoxy)-2,2-dimethyl-hexahydro-pyrano[3,2-<i>d</i>][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2005,vol. 31,p. 576 - 582

47
[ 6240-11-5 ]
(R)-2-adamantyl-2-fluoro-1-ethanol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 8826 - 8828

48
[ 6240-11-5 ]
6-(adamant-1'-yl)hexanethiol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 8720 - 8731

49
[ 6240-11-5 ]
[ 858972-37-9 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 8720 - 8731

50
[ 6240-11-5 ]
[ 112298-63-2 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 8720 - 8731

51
[ 6240-11-5 ]
C₂₅H₂₇F₁₇N₂O₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8751 - 8757

52
[ 6240-11-5 ]
[ 766546-18-3 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 6653 - 6656

53
[ 6240-11-5 ]
1-adamantan-1-yl-prop-2-en-1-ol [ No CAS ]

Reference： [1]Chemical Communications,2000,p. 2031 - 2032

54
[ 6240-11-5 ]
C₁₉H₂₃NO₃Se [ No CAS ]

Reference： [1]Chemical Communications,2000,p. 2031 - 2032

55
[ 6240-11-5 ]
(2-oxiranyl-benzofuran-7-yl)-acetic acid 2-adamantan-1-yl-ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1525 - 1532

56
[ 6240-11-5 ]
[ 273736-88-2 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1525 - 1532

57
[ 6240-11-5 ]
[ 273736-85-9 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1525 - 1532

58
[ 6240-11-5 ]
[ 270587-28-5 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1525 - 1532

59
[ 6240-11-5 ]
(S)-2-Amino-4-methyl-pentanoic acid 2-adamantan-1-yl-ethyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1782 - 1787

60
[ 6240-11-5 ]
(1R,2R)-2-(3-Adamantan-1-yl-propionyl)-cyclopropanecarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 346 - 357

61
[ 6240-11-5 ]
(1R,2R)-2-(3-Adamantan-1-yl-propionyl)-cyclopropanecarboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 346 - 357

62
[ 6240-11-5 ]
(1R,2R)-2-(3-Adamantan-1-yl-1-amino-1-carboxy-propyl)-cyclopropanecarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 346 - 357

63
[ 6240-11-5 ]
(1R,2R)-2-[4-(2-Adamantan-1-yl-ethyl)-2,5-dioxo-imidazolidin-4-yl]-cyclopropanecarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 346 - 357

64
[ 6240-11-5 ]
(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-4-methyl-pentanoic acid 2-adamantan-1-yl-ethyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1782 - 1787

65
[ 6240-11-5 ]
[ 139143-50-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1782 - 1787

66
[ 6240-11-5 ]
(S)-2-[(S)-2-(2-{(R)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid 2-adamantan-1-yl-ethyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1782 - 1787

67
[ 6240-11-5 ]
[ 139143-52-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1782 - 1787

68
[ 6240-11-5 ]
[ 1027205-13-5 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4775 - 4782

69
[ 6240-11-5 ]
(R)-2-((S)-2-{2-[(R)-2-((S)-3-(4-Hydroxy-phenyl)-2-{(S)-2-[(pyridine-3-carbonyl)-amino]-propionylamino}-propionylamino)-propionylamino]-acetylamino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid 2-adamantan-1-yl-ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4775 - 4782

70
[ 6240-11-5 ]
C₅₂H₆₇N₇O₉ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4775 - 4782

71
[ 6240-11-5 ]
4-(2-adamantan-1-yl-ethoxy)-benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3271 - 3281

72
[ 6240-11-5 ]
4-(2-Adamantan-1-yl-ethoxy)-benzoic acid 2,4,5-trichloro-phenyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3271 - 3281

73
[ 6240-11-5 ]
C₅₃H₇₃N₇O₁₇ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3271 - 3281

74
[ 6240-11-5 ]
[ 114653-06-4 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1651 - 1656

75
[ 6240-11-5 ]
[ 114653-12-2 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1651 - 1656

76
[ 6240-11-5 ]
[ 101479-70-3 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1651 - 1656

77
[ 6240-11-5 ]
[ 878-61-5 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 51 - 56

78
[ 6240-11-5 ]
[ 60931-65-9 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 51 - 56

79
[ 6240-11-5 ]
[ 41100-45-2 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 51 - 56

80
[ 6240-11-5 ]
[ 96220-78-9 ]

Reference： [1]Helvetica Chimica Acta,1984,vol. 67,p. 2128 - 2142

81
[ 6240-11-5 ]
<2-(1-adamantyl)ethyl>(dimethylamino)dimethylsilane [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1984,vol. 67,p. 2128 - 2142

82
[ 6240-11-5 ]
[ 107202-68-6 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1487 - 1492
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 6826 - 6837

83
[ 6240-11-5 ]
[ 107202-67-5 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1487 - 1492
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 6826 - 6837

84
[ 6240-11-5 ]
[ 107202-69-7 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1487 - 1492

85
[ 6240-11-5 ]
[ 107202-63-1 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1487 - 1492

86
[ 6240-11-5 ]
[ 107202-63-1 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1487 - 1492

87
[ 6240-11-5 ]
[ 136586-91-9 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 7162 - 7167

88
[ 6240-11-5 ]
[ 136586-92-0 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 7162 - 7167

89
[ 6240-11-5 ]
[ 70873-74-4 ]

Reference： [1]Helvetica Chimica Acta,1979,vol. 62,p. 956 - 964

90
[ 6240-11-5 ]
[ 70893-43-5 ]

Reference： [1]Helvetica Chimica Acta,1979,vol. 62,p. 956 - 964

91
[ 6240-11-5 ]
[ 1137-42-4 ]
[ 845273-11-2 ]

Yield	Reaction Conditions	Operation in experiment
53%	With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 20 - 45℃;	4-[2-(Adamantan-1-yl)ethoxy]benzophenone. In a round-bottom flask equipped with magnetic stirrer, room temperature water bath and dropping funnel 4-hydroxybenzophenone (1.98 g, 10 mmol), 1-adamantaneethanol (1.98 g, 11 mmol) and triphenylphosphine (3.15 g, 12 mmol) were dissolved in dry dioxane (50 mL). DIAD (2.46 ml, 12.5 mmol) was added dropwise within 20 min with stirring. The reaction mixture was heated to 40-45C until starting benzophenone is consumed according to TLC (CHCl3-MeOH 9:1), then cooled to room temperature; the precipitate formed was filtered off, washed successively with cold dioxane and MeOH and dried in vacuo. The solid was purified by column chromatography on silica gel (eluation with benzene). The appropriate fractions were combined and evaporated. The residue was triturated in petroleum ether to give the desired product (1.91 g, 53%), colorless crystals, mp 96C. Rf 0.17 (toluene), 0.57 (toluene-EtOAc, 9:1), 0.64 (toluene-EtOAc, 4:1). NMR (DMSO-d6): 7.74 (d, 2H, J = 8.7 Hz, ArH); 7.70-7.62 (m, 3H, ArH); 7.55 (m, 2H, ArH); 7.07 (d, 2H, J= 8.7 Hz, ArH); 4.14 (t, 2H, J= 7.2 Hz, OCH2); 1.93 (br. s, 3H, H-3,5,7 (adamantane)); 1.70-1.60 (m, 6H, H-4,6,10 (adamantane)); 1.58-1.50 (m, 8H, H-2,8,9 (adamantane), OCH2CH2).

Reference： [1]Patent: EP1506959,2005,A2 .Location in patent: Page 58

92
[ 74124-79-1 ]
[ 6240-11-5 ]
2-(adamant-1-yl)ethyl-succinimidyl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; acetonitrile;	A. A mixture of <strong>[6240-11-5]2-(adamant-1-yl)ethanol</strong> (2.1 g, 12 mmoles), disuccinimidyl carbonate (3.3 g, 13 mmoles) and pyridine (0.86 ml, 10 mmoles) in acetonitrile (50 ml) was stirred at room temperature for 24 hours, then the solvent was evaporated off in the cold and the residue was dissolved in methylene chloride (100 ml). The solution was washed with water (50 ml), 1N HCl (50 ml) and water again (50 ml). The organic phase was dried over anhydrous sodium sulfate and the solvent was evaporated off to give 3 g (9 mmoles) of crude 2-(adamant-1-yl)ethyl-succinimidyl carbonate which was redissolved in THF (30 ml).

Reference： [1]Patent: US6034096,2000,A

93
[ 27174-71-6 ]
[ 6240-11-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	In diethyl ether; water;	Referential Example 11 Production of 2-adamantyl ethanol: 2-adamantyl acetic acid methyl ester 0.57 g (2.47 mill) was added to diethyl ether 20 ml solution of lithium aluminum hydride 0.16 g (4.2 mkf), and the reaction mixture was refluxed under heating for 2 hours. The reaction mixture was cooled and added water. Insoluble material was filtered and the filtrate was extracted with ether, then dried by anhydrous sodium sulfate, which was thereafter removed by filtration. The filtrate was concentrated in vacuo to obtain the product. Yield: 0.23 g (Yield 47%)

Reference： [1]Patent: US5658923,1997,A
[2]Synthetic Communications,2013,vol. 43,p. 1772 - 1777

94
[ 6240-11-5 ]
[ 7693-46-1 ]
2-(1-adamantyl)ethyl (4-nitrophenyl) carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In diethyl ether;	a. 4-Nitrophenyl 2-[tricyclo(3.3.1.13,7)dec-1-yl]ethyl carbonate To a solution of p-nitrophenyl chloroformate (1.17 g, 5.82 mmol) in Et2 O (25 ml) at 0 C. was added pyridine (5 ml) followed by addition of 2-(1-adamant-yl)ethanol (1.00 g, 5.54 mmol) in Et2 O (20 ml) dropwise over 1 hr. The resulting mixture was stirred at room temperature for 12 hr. and partitioned between H2 O and Et2 O. The ethereal layer was washed with 5% aqueous HCl, pH 7.0 phosphate buffer, dried over MgSO4, filtered and the solvents removed under vacuum. The crude product was purified by flash chromatography on silica gel eluding with EtOAc:hexane (5:95) to give the product (1.10 g) as a white powder; TLC, Rf =0.29, silica gel, EtOAc:hexane (5:95).

Reference： [1]Patent: US4910190,1990,A
[2]Chemistry and Biology,2015,vol. 22,p. 1347 - 1361

95
[ 6240-11-5 ]
[ 102196-84-9 ]

Yield	Reaction Conditions	Operation in experiment
46%		(a) 2-[2-(1-Adamantyl)ethyloxy]ethylamine The desired intermediate was obtained, according to the procedure of Example 11, starting from 1-(2-hydroxyethyl)adamantane. Yield: 46%.

Reference： [1]Patent: US4634701,1987,A

96
[ 6240-11-5 ]
[ 7664-93-9 ]
[ 773-37-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; In water;	(a) Preparation of 1-(Adamantan-1-yl)-2-bromoethane A mixture of hydrobromic acid (26.2 g, 48%), concentrated sulphuric acid (10.82 g), and 2-(adamantan-1-yl)ethanol (10.82 g, 0.06 mol) was stirred and heated under reflux for 6 h. After cooling, water (60 ml) was added to the reaction mixture and the mixture was shaken. The organic layer was separated, and was then extracted with ether (3100 ml). The extracts were combined, washed with water (120 ml) and with sodium carbonate solution (20 ml, 10% w/v) and the ether solution was then dried (MgSO4). The ether solution was concentrated under reduced pressure to give a solid, which was recrystallized from aqueous ethanol, to afford 1-(adamantan-1-yl)-2-bromoethane as white plates, m.p. 71-72.

Reference： [1]Patent: US4328234,1982,A

97
[ 6240-11-5 ]
[ 20898-43-5 ]
[ 114787-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethanesulfonic acid anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane;	EXAMPLE 1 Methyl-1-(2-(1-adamantyl)ethyl)-5-diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate. A solution of 11.8 mL trifluoromethanesulfonic anhydride in 70 mL dichloromethane is chilled to -70 C. and treated dropwise with a solution composed of 12.6 g 1-adamantyl-2-hydroxyethane, 12.2 mL diisopropylethylamine and 70 mL dichloromethane. The solution is allowed to warm to -55 C. over 45 min then a solution of 25 g N,1-bis-BOC-histidine methyl ester (J. Chem. Soc., Perkin Trans. I 1982; 1553-61.) in 70 mL dichloromethane is added dropwise. The reaction is then stirred at 25 C. for 24 hr and poured into pH=7, 0.25M potassium phosphate buffer (500 mL), stirring vigorously. The organic layer is separated, washed with the same buffer, dried and concentrated. 3-(2-(1-Adamantyl)ethyl)-N-BOC-histidine methyl ester is isolated by chromatography on silica gel (chloroform-methanol, 99:1) as a gum. NMR (CDCl3) 3.85 (m,2H,NCH2).
	With trifluoromethanesulfonic acid anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane;	EXAMPLE 1. A solution of 11.8 mL trifluoromethanesulfonic anhydride in 70 mL dichloromethane is chilled to -70C and treated dropwise with a solution composed of 12.6 g 1-adamantyl-2-hydroxyethane, 12.2 mL diisopropylethylamine and 70 mL dichloromethane. The solution is allowed to warm to -55C over 45 min then a solution of 25 g N,1-bis-BOC-histidine methyl ester (J. Chem. Soc., Perkin Trans. I 1982; 1553-61.) in 70 mL dichloromethane is added dropwise. The reaction is then stirred at 25C for 24 hr and poured into pH=7, 0.25 M potassium phosphate buffer (500 mL), stirring vigorously. The organic layer is separated, washed with the same buffer, dried and concentrated. 3-(2-(1-Adamantyl)ethyl)-N-BOC-histidine methyl ester is isolated by chromatography on silica gel (chloroform-methanol, 99:1) as a gum. NMR (CDCl3) 3.85 (m,2H,NCH2).

Reference： [1]Patent: US4812462,1989,A
[2]Patent: EP245637,1991,B1

98
[ 156-38-7 ]
[ 6240-11-5 ]
[ 114653-06-4 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In benzene;	EXAMPLE 19 1-Adamantaneethanol (10 g, 0.05 mol), 4-hydroxyphenylacetic acid (8.43 g, 0.05 mol) and p-toluenesulfonic acid (1 g, 0.006 mol) were refluxed in benzene (100 mL) with continuous water separation for 8 hours, then allowed to stir overnight. The residue was washed, first with 5% aqueous sodium bicarbonate solution (50 mL) and then twice with water (50 mL), then was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo. The product, (adamant-1-yl)ethyl 4-hydroxyphenylacetate, was taken up in epichlorohydrin (50 mL) and refluxed for 2 hours in the presence of DBU (1 mL, 0.007 mol).

Reference： [1]Patent: US4829086,1989,A

99
[ 6240-11-5 ]
Methylpyridinium dichlorophosphate [ No CAS ]
bis-<2-(1-adamantyl)ethyl> phosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 20℃;	1- Adamantane ethanol (4.758 g, 26.4 mmol, Aldrich, Milwaukee, WI) was added, and the sealed mixture was stirred overnight at room temperature. It was then poured into 10% NaHCO3 solution (50 mL) and the pyridine was evaporated under vacuum. The slightly yellow solid was dissolved in 1 L of water and extracted with ether (three 150 mL portions). The aqueous phase was acidified with 2 N HCl to pH 1, and then extracted with three 150 mL portions of CHCl3 :H-BUOH (7:3). The combined organic layer (ether and CHCl3 :w-BuOH) was washed with water and a slightly yellow precipitate was formed in the mixed solvents, at which point the solvents were evaporated under vacuum. A slightly yellow solid was formed and was recrystallized from acetone/hexane. The solid was dried under vacuum, yield 60 %

Reference： [1]Patent: WO2006/89007,2006,A2 .Location in patent: Page/Page column 112

100
[ 463-71-8 ]
[ 6240-11-5 ]
[ 1047648-17-8 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 2875 - 2880

101
[ 6240-11-5 ]
[ 59481-71-9 ]
[ 1159340-38-1 ]

Yield	Reaction Conditions	Operation in experiment
22%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 80℃; for 48h;	To a solution of Intermediate 15 (1 g, 4.3 mmol) in tetrahydrofuran (6 ml_) and 1- Adamantaneethanol (0.77 g, 4.2 mmol) in tetrahydrofuran (6 ml_) was added a solution of diethyl azodicarboxylate (2.9 mL, 6.4 mmol) and triphenylphosphine (1.6 g, 6.4 mmol) in tetrahydrofuran (4 mL). The reaction mixture was stirred at 8O0C for 48 hours. The solvent was removed under reduced pressure and partitioned between methylen chloride and water. The organic layer was washed with water, sodium hydrogen carbonate (4%) and brine. The solvent was removed under reduced pressure and the crude was purified by column chromatography with silica gel, eluting with hexane/ethyl acetate (30:1). The title compound was obtained as a solid (0.39 g, 22%). MS (M+): 414.

Reference： [1]Patent: WO2009/68177,2009,A1 .Location in patent: Page/Page column 21

102
[ 6240-11-5 ]
[ 154591-45-4 ]
[ 1193377-72-8 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 8378 - 8383

103
[ 6240-11-5 ]
[ 67688-89-5 ]
[ 530-62-1 ]
[ 1221412-20-9 ]

Yield	Reaction Conditions	Operation in experiment
25%		A mixture of 2-(l-adamantyl)ethanol (0.35 g, 1.9 mmol) and CDI (0.63 g, 3.9 mmol) in THF(15 mL) was stirred at room temperature for 2 hours. Methyl (2£)-3-[4- (aminomethyl)phenyl]acrylate.HCl (0.44 g, 1.9 mmol), DBU (0.3 mL, 1.9 mmol) andDIPEA (0.33 mL, 1.9 mmol) were added and stirred at room temperature for overnight.Reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2x100 mL). Collective EtOAc layer was dried over anhydrous Na2SO4. Concentrated and dried to afford the pure title compound (0.2 g, 25% yield).

Reference： [1]Patent: WO2010/43953,2010,A2 .Location in patent: Page/Page column 38

104
[ 6240-11-5 ]
[ 3443-45-6 ]
[ 1218927-54-8 ]

Reference： [1]Chemistry - An Asian Journal,2009,vol. 4,p. 1562 - 1572

105
[ 6240-11-5 ]
[ 1243599-65-6 ]
C₂₄H₃₄N₄O₇S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4479 - 4482

106
[ 6240-11-5 ]
[ 1243599-67-8 ]
C₂₅H₃₆N₄O₇S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4479 - 4482

107
[ 6240-11-5 ]
[ 773-37-5 ]
1-(2-Bromo-ethyl)-adamantine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
153.2 g (90%)	With hydrogen bromide; In sulfuric acid; water;	1-(2-Bromo-ethyl)-adamantine In a 1 l-roundbottom flask equipped with a reflux condenser 164 g concentrated sulphuric acid and 200 g hydrobromic acid (48% in water) were added subsequently under cooling with an ice bath to 126.20 g (0.70 mole) 2-(1-adamantyl)ethanol. The mixture was refluxed for 6 h and after cooling to room temperature given to 400 g of ice. The aqueous phase was extracted with 400 ml pentane. The organic layer was washed with a 2 M NaOH-solution and with water, dried over magnesium sulphate, and the solvent was removed in vacuo. The product was distilled in vacuo to yield 153.2 g (90%) of (1-(2-Bromo-ethyl)-adamantane as a colourless oil. 1H-NMR (400 MHz, CDCl3): delta=3.29 (t, 2H, CH2Br), 1.71 (t, 2H, CCH2CH2Br), 1.56-1.17 (m, 15H, aliphatic) ppm.

Reference： [1]Patent: US2010/267907,2010,A1

108
[ 6240-11-5 ]
[ 19333-10-9 ]
[ 916429-17-9 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 9041 - 9048

109
[ 6748-68-1 ]
[ 6240-11-5 ]
[ 1262046-86-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7255 - 7258

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Isomers

Technical Information

• Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols are Weakly Basic • Alcohols as Acids • Alcohols Convert Acyl Chlorides into Esters • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alcoholysis of Anhydrides • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldol Addition • Alkene Hydration • Alkene Hydration • Appel Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Carboxylic Acids React with Alcohols to Form Esters • Chloroalkane Synthesis with SOCI2 • Chromium Reagents for Alcohol Oxidation • Chugaev Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Convert Esters into Aldehydes Using a Milder Reducing Agent • Convert Haloalkanes into Alcohols by SN2 • Corey-Kim Oxidation • Decarboxylation of 3-Ketoacids Yields Ketones • Decomposition of Lithium Aluminum Hydride by Protic Solvents • Dess-Martin Oxidation • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Friedel-Crafts Alkylations Using Alcohols • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • Grignard Reagents Transform Esters into Alcohols • Grignard Reagents Transform Esters into Alcohols • Haloalcohol Formation from an Alkene Through Electrophilic Addition • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Halogenation • Heat of Combustion • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydroboration-Oxidation • Hydroboration-Oxidation • Hydrolysis of Haloalkanes • Jones Oxidation • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Osmium Tetroxide Reacts with Alkenes to Give Vicinal Diols • Osmium TetroxideReacts with Alkenes to Give Vicinal Diols • Oxidation of Alcohols by DMSO • Oxymercuration-Demercuration • Preparation of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkoxides with Alkyllithium • Preparation of Amines • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Alcohols • Reactions of Amines • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Ring Opening of an Oxacyclopropane by Lithium Aluminum Hydride • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation • Synthesis of Alcohols from Tertiary Ethers • Synthesis of an Alkyl Sulfonate • The Nucleophilic Opening of Oxacyclopropanes • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Transesterification • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vicinal Anti Dihydroxylation of Alkenes • Williamson Ether Syntheses

Historical Records

Related Functional Groups of
[ 6240-11-5 ]

Aliphatic Cyclic Hydrocarbons

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6240-11-5 ] {[proInfo.proName]}

Quality Control of [ 6240-11-5 ]

Related Doc. of [ 6240-11-5 ]

Product Details of [ 6240-11-5 ]

Calculated chemistry of [ 6240-11-5 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6240-11-5 ]

Application In Synthesis of [ 6240-11-5 ]

[ 6240-11-5 ] Synthesis Path-Downstream 1~109

Technical Information

Related Functional Groups of [ 6240-11-5 ]

Aliphatic Cyclic Hydrocarbons

Alcohols

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 6240-11-5 ]