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Chemical Structure| 6836-19-7 Chemical Structure| 6836-19-7
Chemical Structure| 6836-19-7

7-Methoxy-1-tetralone

CAS No.: 6836-19-7

4.5 *For Research Use Only !

Cat. No.: A103898 Purity: 97%

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Product Citations

Product Citations

Hintzsche, Samuel J. ; Vang, Zoua Pa ; Rivera Torres, Emanuel , et al.

DOI: PubMed ID:

Abstract: Selective deuterium installation into small molecules is becoming increasingly desirable not only for the elucidation of mechanistic pathways and studying biological processes but also because of deuterium's ability to favorably adjust the pharmacokinetic parameters of bioactive molecules. Fused bicyclic moieties, especially those containing heteroatoms, are prevalent in drug discovery and pharmaceuticals. Herein, we report a copper-catalyzed transfer hydrodeuteration of cyclic and heterocyclic alkenes, which enables the synthesis of chromans, quinolinones, and tetrahydronaphthalenes that are precisely deuterated at the benzylic position. We also demonstrate the ability to place one deuterium atom at the homobenzylic site of these scaffolds with high regioselectivity by swapping transfer reagents for their isotopic analogs. Furthermore, examples of chemoselective transfer hydrogenation and transfer deuteration are disclosed, allowing for the simultaneous incorporation of two vicinal hydrogen or deuterium atoms into a double bond.

Keywords: copper ; deuteration ; hydrodeuteration ; hydrogenation ; transition metal catalysis

Purchased from AmBeed: ; ; ; ; 584-08-7 ; ;

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Product Details of [ 6836-19-7 ]

CAS No. :6836-19-7
Formula : C11H12O2
M.W : 176.21
SMILES Code : C1=C(OC)C=CC2=C1C(CCC2)=O
MDL No. :MFCD00001696
InChI Key :GABLTKRIYDNDIN-UHFFFAOYSA-N
Pubchem ID :81276

Safety of [ 6836-19-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis [ 6836-19-7 ]

* 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.

  • Downstream synthetic route of [ 6836-19-7 ]

[ 6836-19-7 ] Synthesis Path-Downstream   1~8

  • 2
  • [ 6836-19-7 ]
  • [ 22246-83-9 ]
YieldReaction ConditionsOperation in experiment
62% With sodium azide; PPA; at 55℃; 130a) Combined 7-Methoxy-l-tetralone (5.0 g, 0.028 mol; ) with Polyphosphoric acid (80 g, 0.7 mol; ) in 2-neck 500 ml Flask fit with overhead mechanical stirrer and septa under nitrogen flow. Sodium azide (2.2 g, 0.034 mol; ) added portionwise over 5 min and the reaction was heated to 550C. Continue stirring overnight. The mixture was poured into water and a white precipitate ensued. The mixture was filtered and washed with water then hexane and dried over 6Oh. 8-Methoxy-l ,3,4,5-tetrahydro-benzo[b]azepin-2-oneobtained as a white solid (3.34 g, 62%). MP:103-104ÂC; 1H-NMR (CDC13, 400 MHz) Î' 7.45 (broad s, IH), 7.13 (d, J = 8.3 Hz, IH), 6.72-6.69 (m, IH), 6.54 (d, J = 2.1 Hz, IH), 3.81 (s, 3H), 2.76 (t, J = 7.2 Hz, 2H), 2.38 (t, J = 7.3 Hz, 2H), 2.25-2.18 (m, 2H); LC/MS: 192.07 (M+H).
Step A: 8-Methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one Prepared from 7-methoxy-1-tetralone by the procedure described in Example 31, Step A. 1 H NMR (200 MHz, CDCl3): 2.19 (m,2H), 2.32 (m,2H), 2.70 (t,6 Hz,2H), 3.76 (s,3H), 6.57 (d,2 Hz,1H), 6.66 (dd;2,8 Hz;1H), 7.09 (d,8 Hz,1H). FAB-MS: calculated for C11 H13 NO2 191; found 192 (M+H,100%).
  • 4
  • [ 6836-19-7 ]
  • 3-amino-7-chloro-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one [ No CAS ]
  • [ 22246-83-9 ]
YieldReaction ConditionsOperation in experiment
The 8-methoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 132-134 was similarly prepared from 7-methoxy-α-tetralone. 3-Amino-7-chloro-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one was synthesised as follows:
The 8-methoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 132-4 was similarly prepared from 7-methoxy-α-tetralone. 3-Amino-7-chloro-2,3,4,5-tetrahydro-1H[1]benzazepin-2-one was synthesised as follows:
  • 5
  • [ 7664-93-9 ]
  • [ 6836-19-7 ]
  • [ 22246-83-9 ]
YieldReaction ConditionsOperation in experiment
In acetic acid; (b) Schmidt-reaction: 4 g of sodium azide are added portionwise to 8.3 g of 7-methoxy-1-tetralone in 36 ml of acetic acid. Then 17 ml of concentrated sulphuric acid are added dropwise, without a rise in temperature over 40; the solution is poured onto ice and neutralised with 2 N sodium hydroxide solution. The separating bulk of crystals is removed and recrystallized from ethyl acetate. One obtains 6.4 g of 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (m.p. 137-138).
  • 7
  • [ 6836-19-7 ]
  • [ 372-09-8 ]
  • [ 138113-08-3 ]
YieldReaction ConditionsOperation in experiment
95% With 5%-palladium/activated carbon; In dimethyl sulfoxide; at 20℃; for 4.5h;Molecular sieve; Add 400 mL of dimethylsulfoxide to the dry reaction flask(7-methoxy-3,4-naphthyl) acetonitrile200 g (1.0 mol),Stirring at room temperature;To the above solution, 20 g of 4A molecular sieve and 10 g of palladium on carbon (5%) were added,Heated to reflux for 4.5 hours,The reaction solution was filtered,The filtrate was extracted with toluene,Organic phase concentrated dry(7-methoxy-1-naphthyl) acetonitrile190g,Yield 95%
  • 8
  • [ 56442-17-2 ]
  • [ 6836-19-7 ]
  • C25H21FO3 [ No CAS ]
 

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