Home Cart 0 Sign in  
X

[ CAS No. 941-37-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 941-37-7
Chemical Structure| 941-37-7
Chemical Structure| 941-37-7
Structure of 941-37-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 941-37-7 ]

Related Doc. of [ 941-37-7 ]

Alternatived Products of [ 941-37-7 ]

Product Details of [ 941-37-7 ]

CAS No. :941-37-7 MDL No. :MFCD00077197
Formula : C12H19Br Boiling Point : -
Linear Structure Formula :- InChI Key :QUCXLVDIVQWYJR-UHFFFAOYSA-N
M.W : 243.18 Pubchem ID :98317
Synonyms :
Chemical Name :1-Bromo-3,5-dimethyladamantane

Calculated chemistry of [ 941-37-7 ]

Physicochemical Properties

Num. heavy atoms : 13
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 : 60.84
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.93
Log Po/w (XLOGP3) : 4.98
Log Po/w (WLOGP) : 4.13
Log Po/w (MLOGP) : 4.5
Log Po/w (SILICOS-IT) : 4.16
Consensus Log Po/w : 4.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.49
Solubility : 0.00796 mg/ml ; 0.0000327 mol/l
Class : Moderately soluble
Log S (Ali) : -4.72
Solubility : 0.00465 mg/ml ; 0.0000191 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.02
Solubility : 0.0234 mg/ml ; 0.0000962 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 5.66

Safety of [ 941-37-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 941-37-7 ]

* 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 [ 941-37-7 ]
  • Downstream synthetic route of [ 941-37-7 ]

[ 941-37-7 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 941-37-7 ]
  • [ 702-79-4 ]
YieldReaction ConditionsOperation in experiment
100% at 90℃; for 1 h; Inert atmosphere General procedure: To a solution of thiocarbonate 5g (107 mg, 0.200 mmol) in CPME (0.5 mL) were added dropwise a solution of n-Bu3SnH (75.7 mg, 0.260 mmol) and   AIBN (6.6 mg, 0.040 mmol) in CPME (1.5 mL) with a syringe pump over 30 min at 90 °C. The resultant mixture was stirred at 90 °C for 30 min and concentrated. The residue was purified by 10percent w/w K2CO3-silica gel flash column chromatography (hexane→hexane/EtOAc=100/1→50/1→20/1) to give the cis-fused cyclized product 6g (53.6 mg, 0.140 mmol, 70percent) and 2.8:1 mixture of cis and trans-fused diastereomers (22.0 mg, 0.0572 mmol, 29percent). These isomers were separated by the repeated column chromatography for spectral analysis.#10;
Reference: [1] Tetrahedron, 2013, vol. 69, # 10, p. 2251 - 2259
[2] Organic Letters, 2008, vol. 10, # 4, p. 533 - 536
[3] Journal of Organic Chemistry, 1983, vol. 48, # 16, p. 2762 - 2765
  • 2
  • [ 941-37-7 ]
  • [ 75-16-1 ]
  • [ 702-79-4 ]
  • [ 707-35-7 ]
Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
  • 3
  • [ 702-79-4 ]
  • [ 941-37-7 ]
YieldReaction ConditionsOperation in experiment
92% With aluminum (III) chloride; bromine In 1,2-dichloro-ethane at 15℃; A) 59.9 g (0.345 mol) of bromine,Anhydrous aluminum trichloride 10 g (0.075 mol)1,2-dichloroethane (37.8 g) was added to the reactor to stir well;B) heating the reaction solution A to 15 ° C;C) 50 g (0.3 mol) of 1,3-dimethyladamantane was added to the mixture obtained in the step (b) to obtain a reaction mixtureIn the liquid B, the reaction process with 5percent sodium hydroxide solution absorption;D) Add 400 g of saturated sodium bisulfite solution to the reaction solution B until the red color in the reaction solution completely disappeared,The organic phase C and the water phase D;E) The organic phase C was washed with 400 g of water and the washed organic phase C was dried with 20 g of anhydrous sodium sulfate;F) the organic phase C obtained in step (e) is distilled off to obtain the crude product E;G) crude product E was distilled under reduced pressure to give 1-bromo-3,5-dimethyl adamantane, yield 92percent, gas chromatography purity ≥ 99percent.
85% at 150℃; for 3 h; 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] Patent: CN104592034, 2016, B, . Location in patent: Paragraph 0092-0099
[2] Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5107 - 5110
[3] Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187[4] Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199
[5] Patent: US5061703, 1991, A,
[6] Journal of Medicinal Chemistry, 1963, vol. 6, p. 760 - 763
[7] Patent: WO2008/62472, 2008, A2, . Location in patent: Page/Page column 12-13
[8] Patent: WO2010/15415, 2010, A1, . Location in patent: Page/Page column 16-17
[9] Patent: WO2010/67252, 2010, A1, . Location in patent: Page/Page column 6
[10] Patent: WO2010/83996, 2010, A1, . Location in patent: Page/Page column 20
[11] Patent: WO2006/122238, 2006, A1, . Location in patent: Page/Page column 11
[12] Patent: WO2006/122238, 2006, A1, . Location in patent: Page/Page column 14-15
[13] Patent: WO2007/132476, 2007, A2, . Location in patent: Page/Page column 5; 10; 14; 16
  • 4
  • [ 707-37-9 ]
  • [ 941-37-7 ]
Reference: [1] Tetrahedron, 2013, vol. 69, # 10, p. 2251 - 2259
  • 5
  • [ 19982-07-1 ]
  • [ 707-37-9 ]
  • [ 941-37-7 ]
  • [ 19982-08-2 ]
  • [ 41100-52-1 ]
Reference: [1] Patent: WO2008/62472, 2008, A2, . Location in patent: Page/Page column 16-17
  • 6
  • [ 702-79-4 ]
  • [ 707-37-9 ]
  • [ 941-37-7 ]
Reference: [1] Russian Journal of Organic Chemistry, 2014, vol. 50, # 1, p. 25 - 28[2] Zh. Org. Khim., 2014, vol. 50, # 1, p. 33 - 36,4
  • 7
  • [ 64-18-6 ]
  • [ 941-37-7 ]
  • [ 14670-94-1 ]
Reference: [1] , 1966, vol. 2, p. 1590 - 1592[2] Zhurnal Organicheskoi Khimii, 1966, vol. 2, # 9, p. 1612 - 1615
  • 8
  • [ 941-37-7 ]
  • [ 75-05-8 ]
  • [ 19982-07-1 ]
YieldReaction ConditionsOperation in experiment
95.5%
Stage #1: at 20 - 87℃; for 3.75 - 4.33 h;
Stage #2: at 35 - 45℃;
Example 4: l-Acetamido-3.5-dimethyladamantane (Ac-NH-DM AD) synthesis; 500 g of l-bromo-3,5-dimethyladamantane and 393 g (500 ml) of acetonitrile were loaded into a 5-liter reactor equipped with condenser, mechanical stirrer, thermometer at 20-250C under nitrogen. After about 15-20 minutes, 806 g of 75percent phosphoric acid was added. After addition of the phosphoric acid, the internal temperature of the reactor rose to 30-320C and a biphasic system was obtained. The biphasic system was warmed to 87+/-2°C over about 30 min (slight reflux) and the temperature maintained for 3-3.5 hrs. A monophasic system was then obtained. At this point, the reaction was complete (sum of 1- hydroxy-3,5-dimethyladamantane and l-bromo-3,5-dimethyladamantane less than 1percent). n-butanol (1000ml) and water (770ml) were added to the monophasic system and the system was cooled to 20-250C. Sodium hydroxide 30percent (337.5g) was added and the temperature rises to 40-450C. Two phases form and the phases were separated at 35-400C. The aqueous phase was discarded and water (385g) was added to the organic phase to form a biphasic system. Then NaOH 30percent (337.5g) was added, while maintaining the temperature at 40-450C and adjusting the pH to 5.5-7. The phases were separated at 40- 45°. The organic phase was concentrated under vacuum (res. pressure 45-50 mrnHg, external temperature 80-850C, internal temperature 40-700C) until a residual volume of 600-650ml was obtained. After cooling to 55-600C, acetone (474g) was added. The <n="22"/>resulting suspension was warmed to reflux (62-63°C) until complete dissolution was obtained. After cooling to 500C, water (2000ml) was slowly added (over about 30min) at 45-500C and crystallization of l-acetamido-S.S-dimethyladamantane occurred. At the beginning some oil separated. Usually spontaneous crystallization occurs, but if not, seeding with about 0.2-0.3percent of solid is necessary. After 1.5-2hrs at 18+/-3°C solid was filtered, washed with water and dried at 45-500C for 15hrs. Dry weight: 435g, Yield: 95.5percent, Purity: 99.84percent by GC.
Reference: [1] Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5107 - 5110
[2] Patent: WO2007/126886, 2007, A1, . Location in patent: Page/Page column 20-21
[3] Journal of Medicinal Chemistry, 1963, vol. 6, p. 760 - 763
[4] Patent: WO2010/67252, 2010, A1, . Location in patent: Page/Page column 6-7
[5] Patent: WO2007/132476, 2007, A2, . Location in patent: Page/Page column 6; 10
  • 9
  • [ 60-35-5 ]
  • [ 941-37-7 ]
  • [ 19982-07-1 ]
YieldReaction ConditionsOperation in experiment
99% at 120 - 130℃; Inert atmosphere; Autoclave General procedure: General procedure for the synthesis of N-(3,5-dimethyladamant-1-yl)acetamides. The stainless steel pressure microreactor (V = 17 mL) or glass vial was charged under argon with 0.3 mmol of manganese-containing catalyst, 10 mmol of 1-bromo-3,5-di-methyladamantane I, and 30 mmol of amide. The reac-tion mixture was heated at 120–130°C for 3–4 h with stirring. After the reaction completed, the rector (vial) was cooled to room temperature and opened. The reaction mixture was washed with water, and then the reaction product was extracted with methylene chloride (3 5 mL). The solvent was removed under a reduced pressure, and the residue was recrystallized. N-(3,5-Dimethyladamant-1-yl)amides II–V were puri-fied by column chromatography (silica gel, eluent – hexane–ethyl acetate).
94% at 125℃; Compound (IV) (60 g, 0.247 mol)Mix with acetamide (116.6 g, 1.974 mol).The oil bath was heated to 125°C and incubated for 4~5h.Stop the reaction. Cool, add 600ml of dichloromethane and 300ml of drinking water,Stir well, stand and separate the liquid. The aqueous phase is extracted once more with 300 ml of dichloromethane.Combine the organic phases. 600ml of drinking water is washed twice and the organic phase is concentrated to dryness under reduced pressure and recrystallized from water.Drying under reduced pressure gave compound (III) as a white solid (GC> 98.0percent, yield 94percent).
1548 g at 150℃; Inert atmosphere Followed by the addition of 1.8 kg of starting material,Acetamide 2.2 kg,Nitrogen protection.The reaction solution was heated to 150 ° C and stirred for 6 to 7 hours.3.6 L of water was slowly added,Stirring was continued for 5 to 10 minutes,Further 1.8 L of methylene chloride was added, Standing for 3 to 5 minutes,The organic layer was separated,Repeat the above procedure twice.To the organic layer was added 1.8 L of water,Stirring for 5 to 10 minutes,Standing for 3 to 5 minutes,Abandoned water layer.To the organic layer was added 1.8 L of saturated sodium chloride,Stirring for 5 to 10 minutes, standing for 3 to 5 minutes,Abandoned water layer. 500 g of anhydrous sodium sulfate was added to the organic layer, and the mixture was stirred and dried for 2 hours.In the water bath temperature of 40 ~ 45 , vacuum ≤-0.090MPa, the vacuum distillation of the solvent, 1 - acetylamino - 3 -1548 g of dimethyl adamantane.
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 7, p. 1771 - 1772[2] Zh. Obshch. Khim., 2015, vol. 85, # 7, p. 1210 - 1211,2
[3] Patent: CN104557567, 2018, B, . Location in patent: Paragraph 0038; 0049; 0062; 0063; 0070; 0077
[4] Patent: WO2008/62472, 2008, A2, . Location in patent: Page/Page column 13-17
[5] Patent: CN104529791, 2016, B, . Location in patent: Paragraph 0049; 0050
  • 10
  • [ 941-37-7 ]
  • [ 19982-07-1 ]
Reference: [1] Patent: WO2007/132476, 2007, A2,
  • 11
  • [ 941-37-7 ]
  • [ 41100-52-1 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: at 20 - 90℃; for 1 h; Inert atmosphere
Stage #2: With hydrogenchloride In water at 20 - 110℃; for 4 h; Inert atmosphere
24 g of 1-bromo-3,5-dimethyladamantane and 36 g of urethane were placed in a reaction flask,Add 240 ml98percent formic acid,Stirring at room temperature dissolved,Argon protection,The reaction was heated to 90 ° C for 1 hour.Cooled to room temperature,The formic acid was distilled off under reduced pressure,Then add the mass concentration of 10percent hydrochloric acid 60 ml,And the mixture was heated to 110 ° C and reacted for 4 hours. Cooled to 0 ° C, the crystal analysisOut, to be complete crystallization,Filtering to obtain memantine hydrochloride.GC purity: 99.0percent, Yield: 85percent.
Reference: [1] Patent: CN103833555, 2016, B, . Location in patent: Paragraph 0048; 0049; 0050
[2] Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5107 - 5110
[3] Patent: CN104557567, 2018, B,
[4] Patent: WO2006/122238, 2006, A1,
[5] Patent: WO2006/122238, 2006, A1,
[6] Patent: WO2006/122238, 2006, A1,
[7] Patent: WO2006/122238, 2006, A1,
[8] Patent: WO2007/126886, 2007, A1,
[9] Patent: WO2007/132476, 2007, A2,
[10] Patent: WO2007/132476, 2007, A2,
  • 12
  • [ 941-37-7 ]
  • [ 57-13-6 ]
  • [ 41100-52-1 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: at 120℃; for 4 h;
Stage #2: With sodium hydroxide In 1-methyl-pyrrolidin-2-one at 120℃; for 6 h;
Stage #3: With hydrogenchloride In 1-methyl-pyrrolidin-2-one; water at 25℃; for 16 h;
A 5 L flask was charged with 300.00 g of 1-bromo-3,5-dimethyladamantane (1233.7 mmol), urea 296.37 g (4934.6 mmol) and NMP 600 mL were added, and the mixture was stirred at 120 ° C. for 4 hours (yellow solution). The reaction solution was cooled to room temperature, 1500 mL of NMP and 493.46 g (12336.5 mmol) of sodium hydroxide were added, and the mixture was stirred at 120 ° C. for 6 hours (light yellow slurry). After cooling the reaction solution to room temperature, 2000 mL of water was added and the solution was transferred to a 10 L flask, 3400 mL of water and 1500 mL of toluene were further added and vigorously stirred for 20 minutes.The mixture was allowed to stand for 1 hour, and separated into an aqueous layer and an organic layer.The aqueous layer was returned to a 10 L flask, 1500 mL of toluene was added and vigorously stirred for 20 minutes. The mixture was allowed to stand for 20 minutes, and the aqueous layer was removed (pH 12.5).The organic layers were combined, 900 mL of water was added, vigorously stirred for 20 minutes, allowed to stand for 20 minutes, and the aqueous layer was removed. The obtained organic layer was cooled to 15 ° C. or lower, 137.44 g (1357.0 mmol) of concentrated hydrochloric acid was added, and the mixture was stirred at 25 ° C. for 16 hours.The obtained slurry was suction filtered, the cake was washed twice with 300 mL of toluene, and the obtained memantine hydrochloride wet crystals were dried under reduced pressure to obtain 258.62 g of memantine hydrochloride (yield 97percent, GC Purity 99.8percent)
Reference: [1] Patent: JP2017/39656, 2017, A, . Location in patent: Paragraph 0035
  • 13
  • [ 19982-07-1 ]
  • [ 707-37-9 ]
  • [ 941-37-7 ]
  • [ 19982-08-2 ]
  • [ 41100-52-1 ]
Reference: [1] Patent: WO2008/62472, 2008, A2, . Location in patent: Page/Page column 16-17
  • 14
  • [ 941-37-7 ]
  • [ 77287-34-4 ]
  • [ 351329-88-9 ]
YieldReaction ConditionsOperation in experiment
78% at 120 - 130℃; Inert atmosphere; Autoclave General procedure: General procedure for the synthesis of N-(3,5-dimethyladamant-1-yl)acetamides. The stainless steel pressure microreactor (V = 17 mL) or glass vial was charged under argon with 0.3 mmol of manganese-containing catalyst, 10 mmol of 1-bromo-3,5-di-methyladamantane I, and 30 mmol of amide. The reac-tion mixture was heated at 120–130°C for 3–4 h with stirring. After the reaction completed, the rector (vial) was cooled to room temperature and opened. The reaction mixture was washed with water, and then the reaction product was extracted with methylene chloride (3 5 mL). The solvent was removed under a reduced pressure, and the residue was recrystallized. N-(3,5-Dimethyladamant-1-yl)amides II–V were puri-fied by column chromatography (silica gel, eluent – hexane–ethyl acetate). N-(3,5-Dimethyladamantan-1-yl)formamide (II). Yield 78percent, mp 69–70°C (hexane). Physico-chemical constants and NMR spectral data correspond to the literature data [7].
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 7, p. 1771 - 1772[2] Zh. Obshch. Khim., 2015, vol. 85, # 7, p. 1210 - 1211,2
[3] Patent: WO2010/15415, 2010, A1, . Location in patent: Page/Page column 16-17
[4] Patent: WO2010/83996, 2010, A1, . Location in patent: Page/Page column 20-21
  • 15
  • [ 941-37-7 ]
  • [ 77287-34-4 ]
  • [ 351329-88-9 ]
  • [ 707-37-9 ]
Reference: [1] Patent: WO2006/122238, 2006, A1, . Location in patent: Page/Page column 11-12
  • 16
  • [ 941-37-7 ]
  • [ 351329-88-9 ]
  • [ 707-37-9 ]
Reference: [1] Patent: WO2006/122238, 2006, A1, . Location in patent: Page/Page column 14-15
  • 17
  • [ 941-37-7 ]
  • [ 351329-88-9 ]
Reference: [1] Patent: WO2006/122238, 2006, A1,
[2] Patent: WO2006/122238, 2006, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 941-37-7 ]

Aliphatic Cyclic Hydrocarbons

Chemical Structure| 768-90-1

[ 768-90-1 ]

1-Bromoadamantane

Similarity: 0.94

Chemical Structure| 876-53-9

[ 876-53-9 ]

1,3-Dibromoadamantane

Similarity: 0.89

Chemical Structure| 707-34-6

[ 707-34-6 ]

1,3,5-Tribromoadamantane

Similarity: 0.89

Chemical Structure| 108-85-0

[ 108-85-0 ]

Bromocyclohexane

Similarity: 0.76

Chemical Structure| 1647-26-3

[ 1647-26-3 ]

1-Bromo-2-cyclohexylethane

Similarity: 0.76

Bromides

Chemical Structure| 768-90-1

[ 768-90-1 ]

1-Bromoadamantane

Similarity: 0.94

Chemical Structure| 876-53-9

[ 876-53-9 ]

1,3-Dibromoadamantane

Similarity: 0.89

Chemical Structure| 707-34-6

[ 707-34-6 ]

1,3,5-Tribromoadamantane

Similarity: 0.89

Chemical Structure| 73908-04-0

[ 73908-04-0 ]

3-Bromo-3-ethylpentane

Similarity: 0.82

Chemical Structure| 1647-26-3

[ 1647-26-3 ]

1-Bromo-2-cyclohexylethane

Similarity: 0.76