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[ CAS No. 2094-72-6 ] {[proInfo.proName]}

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Chemical Structure| 2094-72-6
Chemical Structure| 2094-72-6
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Product Details of [ 2094-72-6 ]

CAS No. :2094-72-6 MDL No. :MFCD00074724
Formula : C11H15ClO Boiling Point : -
Linear Structure Formula :ClC(O)C10H15 InChI Key :MIBQYWIOHFTKHD-UHFFFAOYSA-N
M.W : 198.69 Pubchem ID :98915
Synonyms :

Safety of [ 2094-72-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2094-72-6 ]

* 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 [ 2094-72-6 ]

[ 2094-72-6 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 57497-39-9 ]
  • [ 2094-72-6 ]
  • N-tert-Butyl-O-(1-adamantancarbonyl)hydroxylamin [ No CAS ]
  • N-tert-Butyl-1-adamantancarbohydroxamsaeure [ No CAS ]
  • 2
  • [ 1454-85-9 ]
  • [ 2094-72-6 ]
  • 1-heptadecyl 1-adamantanecarboxylate [ No CAS ]
  • 3
  • [ 98-55-5 ]
  • [ 2094-72-6 ]
  • dimethyl(4-methyl-3-cyclohexenyl)methyl 1-adamantanecarboxylate [ No CAS ]
  • 4
  • [ 29390-67-8 ]
  • [ 2094-72-6 ]
  • mono-6-deoxy-6-(1-adamantylcarboxamido)-β-cyclodextrin [ No CAS ]
  • 5
  • [ 71574-33-9 ]
  • [ 2094-72-6 ]
  • [ 377063-72-4 ]
YieldReaction ConditionsOperation in experiment
74% To a solution of 4,5~dimethyl-ihiazo3-2-ylamine hydrochloride (1 65 g, 10 0 mmol) in TetaF (100 mL) was added tiiethylamine (4 2 mL, 30 mmol) and adamantane-l-carbonyl chloride (2 2 g, 1 1 mmol) The mixture was heated at reflux overnight and then concentrated under reduced pressure The residue was diluted with ethyl acetate, washed with IM NaHCO3, dried (Na2SO4), filtered and concentrated Purification by column chromatography (SiO2, 10 %ethyl acetate: 90% hexanes) afforded 2 15 g (74%) of the title compound MS (ESI+) m/z 291 (M+H)+
  • 6
  • [ 2094-72-6 ]
  • [ 51169-05-2 ]
  • [ 1029433-07-5 ]
  • 7
  • [ 33893-89-9 ]
  • [ 2094-72-6 ]
  • [ 828-51-3 ]
  • [ 1415251-74-9 ]
YieldReaction ConditionsOperation in experiment
50% With pyridine;Inert atmosphere; Reflux; The reaction was performed with 5-(2'-pyridyl)-1H-tetrazole (500 mg, 3.40 mmol) and 1-adamantanecarboxylic acid chloride (675 mg, 3.40 mmol, Acros) in pyridine (3.5 mL). The reaction mixture was extracted with ether/H2O. The organic layer was washed with water (to remove pyridine) and evaporated. Purification by column chromatography was performed on silica (10 g). Elution with CH2Cl2 removed the impurities. Elution with 0.5% of CH3OH in CH2Cl2 recovered the product. It was re-dissolved in ether, and hexane (20 mL) was added. The ether was rotor-evaporated to leave a suspension of the product in hexane. The suspension was cooled to -15 C overnight and filtered. The product was washed with cold hexane. The product purified in this way contained 10% of 1-adamantanecarboxylic acid (detected by 1H and 13C NMR). To remove the acid, the product was sonicated in saturated aqueous solution of Na2CO3 for 10 min and extracted with ether. The organic layer was washed with saturated aqueous solution of Na2CO3 and water. It was evaporated, and the extraction with Na2CO3 (aq. sat.) and ether was repeated one more time. White solid: 477 mg (1.70 mmol, 50%). Anal. Calc. for C17H19N3O (MW 281.35): C, 72.57; H, 6.81; N, 14.94. Found: C, 72.54; H, 6.87; N, 14.74%. 1H NMR (400 MHz, [D6]dmso): delta = 8.79-8.74 (m, 1H), 8.19-8.13 (m, 1H), 8.03 (td, J = 8.0, 1.6 Hz, 1H), 7.62 (ddd, J = 7.6, 4.8, 1.2 Hz, 1H), 2.10-2.04 (m, br, 9H), 1.77 (br, 6H) ppm. 13C NMR (100 MHz, CD2Cl2): delta = 173.68, 163.90, 150.34, 144.25, 137.28, 125.72, 123.00, 40.12, 36.44, 34.71, 28.13 ppm. GC-EI+ MS: m/z 281 (M+, 100%).
  • 8
  • [ 2343-22-8 ]
  • [ 2094-72-6 ]
  • [ 1422444-10-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h; General procedure: A mixture of 24.5 mg (0.18 mmol) 1,2,3,4-tetrahydroquinoline, 37.3 mg (0.188 mmol) 1-adamatanecarbonyl chloride and 44.4 mg (0.34 mmol) DIPEA in 1 mL DCM was shaken at room temperature for 4 h. The mixture was evaporated, dissolved in DMF and subjected to column chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 34.9 mg (64%) of the title compound as white solid.
  • 9
  • [ 88675-24-5 ]
  • [ 2094-72-6 ]
  • ((3-aminotetrahydrofuranyl)tricyclo[3.3.1.13,7]dec-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h; DIPEA (1 .93ml, 1 1 .1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1 - carbonyl chloride (1 ) (2g, 10.1 mmol) and <strong>[88675-24-5]3-aminotetrahydrofuran</strong>; (29)(1 .0ml, 1 1 mmol) in DCM (20ml) and the solution stirred at room temperature for 4 hours. The solution was washed with 0.1 N HCI (30ml), saturated NaHC03 (30ml), dried (Na2S04), filtered and the solvents removed to give crude product which was further purified via crystallization from 15percent EA in hexanes to give as a white solid
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h; DIPEA (1 .93ml, 1 1 .1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1 - carbonyl chloride (1 ) (2g, 10.1 mmol) and <strong>[88675-24-5]3-aminotetrahydrofuran</strong>; (29)(1 .0ml, 1 1 mmol) in DCM (20ml) and the solution stirred at room temperature for 4 hours. The solution was washed with 0.1 N HCI (30ml), saturated NaHC03 (30ml), dried (Na2S04), filtered and the solvents removed to give crude product which was further purified via crystallization from 15percent EA in hexanes to give as a white solid
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h; DIPEA (1.93 ml, 11.1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1-carbonyl chloride (1) (2 g, 10.1 mmol) and <strong>[88675-24-5]3-aminotetrahydrofuran</strong>; (29)(1.0 ml, 11 mmol) in DCM (20 ml) and the solution stirred at room temperature for 4 hours. The solution was washed with 0.1N HCl (30 ml), saturated NaHCO3 (30 ml), dried (Na2SO4), filtered and the solvents removed to give crude product which was further purified via crystallization from 15percent EA in hexanes to give as a white solid.
  • 10
  • [ 27425-92-9 ]
  • [ 2094-72-6 ]
  • C32H58O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; 1g of PEG monomethyl ester (PEG5000: 0.2mmol; PEG500: 2.1mmol) was dissolved in anhydrous DCM (PEG5000: 25ml; PEG500: 150ml) and cooled to 0C. Adamantane carbonyl chloride (5eq), DIPEA (10eq) and DMAP (1% cat.) were added and the mixture warmed to room temperature and stirred overnight under nitrogen. The mixture was transferred to a separating funnel and washed with 5% citric acid (50ml), saturated NaHCO3 (50ml), and brine (50ml). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. Ad-PEG500 was purified by column chromatography over silica gel (DCM/MeOH: 9/1) to yield the product E as a yellow oil (1.1g, 83%). Ad-PEG5000 was dissolved in a minimum amount of DCM and precipitated from diethyl ether to yield the product F as a white solid (805mg, 78%).
  • 11
  • [ 2094-72-6 ]
  • [ 446065-11-8 ]
  • [ 77817-08-4 ]
  • 12
  • [ 40359-32-8 ]
  • [ 2094-72-6 ]
  • 4-haloaniline [ No CAS ]
  • N-(4-((3-(allyloxy)phenyl)(hydroxy)methyl)phenyl)adamantane-1-carboxamide [ No CAS ]
  • 13
  • [ 923283-54-9 ]
  • [ 2094-72-6 ]
  • methyl 4-[((adamantan-1-yl)carbonyl)amino]-1-methyl-1H-pyrazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% In 1,4-dioxane; General procedure: A solution of the appropriate acyl chloride (adamantane-2-carbonyl chloride or 4-substituted benzoyl chloride, 1.3mmol) in dry dioxane (3mL) was added dropwise to a solution of 7a-m, 15, 16, 17 (1.0mmol) in 10mL of the same solvent, maintained at 70C. After the addition was complete, the mixture was refluxed until the formation of hydrogen chloride stopped (1-18h). The solution was concentrated in vacuo and the residue was dissolved in DCM (30mL), washed with NaHCO3 solution (10mL), dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by recrystallization from MeOH or flash column chromatography on silica gel using the reported eluent system.
  • 14
  • [ 637336-53-9 ]
  • [ 2094-72-6 ]
  • methyl 4-[((adamantan-1-yl)carbonyl)amino]-1-methyl-1H-pyrazole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; General procedure: A solution of the appropriate acyl chloride (adamantane-2-carbonyl chloride or 4-substituted benzoyl chloride, 1.3mmol) in dry dioxane (3mL) was added dropwise to a solution of 7a-m, 15, 16, 17 (1.0mmol) in 10mL of the same solvent, maintained at 70C. After the addition was complete, the mixture was refluxed until the formation of hydrogen chloride stopped (1-18h). The solution was concentrated in vacuo and the residue was dissolved in DCM (30mL), washed with NaHCO3 solution (10mL), dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by recrystallization from MeOH or flash column chromatography on silica gel using the reported eluent system.
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