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Chemical Structure| 2676865-17-9 Chemical Structure| 2676865-17-9

Structure of 2676865-17-9

Chemical Structure| 2676865-17-9

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Product Details of [ 2676865-17-9 ]

CAS No. :2676865-17-9
Formula : C15H17NO4
M.W : 275.30
SMILES Code : O=C(C1CC2=C(C([N+]([O-])=O)=C3CCCC3=C2)C1)OCC
English Name :Ethyl 4-nitro-1,2,3,5,6,7-hexahydro-s-indacene-2-carboxylate
MDL No. :N/A
InChI Key :OKFXQSCGNAREFL-UHFFFAOYSA-N
Pubchem ID :162394395

Safety of [ 2676865-17-9 ]

Application In Synthesis of [ 2676865-17-9 ]

* 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 [ 2676865-17-9 ]

[ 2676865-17-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 496-11-7 ]
  • [ 2676865-17-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 8 h / 0 - 10 °C / Large scale 2.1: sulfuric acid / 48 h / 55 °C 2.2: 2 h / 0 - 10 °C 3.1: Lithium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C 3.2: 16 h / 25 °C 4.1: trifluoroacetic acid; triethylsilane / 16 h / 70 °C
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / dichloromethane / 8 h / 0 - 10 °C / Large scale 2.1: sulfuric acid / 40 h / 55 °C 3.1: sulfuric acid; nitric acid / 1 h / 0 °C 4.1: Lithium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 16 h / 25 °C 5.1: trifluoroacetic acid; triethylsilane / 16 h / 70 °C
  • 2
  • [ 14927-64-1 ]
  • [ 2676865-17-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sulfuric acid; nitric acid / 1 h / 0 °C 2.1: Lithium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C 2.2: 16 h / 25 °C 3.1: trifluoroacetic acid; triethylsilane / 16 h / 70 °C
  • 3
  • [ 39105-39-0 ]
  • [ 2676865-17-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sulfuric acid / 48 h / 55 °C 1.2: 2 h / 0 - 10 °C 2.1: Lithium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C 2.2: 16 h / 25 °C 3.1: trifluoroacetic acid; triethylsilane / 16 h / 70 °C
Multi-step reaction with 4 steps 1.1: sulfuric acid / 40 h / 55 °C 2.1: sulfuric acid; nitric acid / 1 h / 0 °C 3.1: Lithium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C 3.2: 16 h / 25 °C 4.1: trifluoroacetic acid; triethylsilane / 16 h / 70 °C
  • 4
  • [ 620592-45-2 ]
  • [ 2676865-17-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: Lithium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 16 h / 25 °C 2.1: trifluoroacetic acid; triethylsilane / 16 h / 70 °C
  • 5
  • [ 2676865-16-8 ]
  • [ 2676865-17-9 ]
YieldReaction ConditionsOperation in experiment
47% With triethylsilane; trifluoroacetic acid at 70℃; for 16h; 332a-d.2 To a stirred solution of ethyl 3~hydroxy~4~nitro-L5,6,7~t6trahydro-s~indacene~2~carboxylate (1 g, 3.5 mmol) in TFA (30 mL) was added EtySiH (3.3 ml,, 20.7 mmolThe reaction was heated at 70 °C. After 16 hours, the reaction was quenched with saturated aqueous NaHCOs (150 mL). The aqueous layer was extracted with DCM (150 mL x 2). The combined organic layers were dried over anhydrous Na^SiXi, filtered and concentrated under reduced pressure. The crude residue was purified by flash column chromatography (silica, 5% EtOAc in petroleum ether) to give ethyl 4-nitro- 1,2, 3,5,6, 7-hexaliydro-s- indacene-2-earboxyiate (0.45 g , yield: 47%) as a light yellow oil.lH NMR (400 MHz, CDCL): d:::7.31 (s, 1 H), 4.19 (q, J - 12 Hz, 2 H), 3.64-3.54 (m, 2 H), 3.40-3.33 (m, 1 H), 3.30-3.18 (m, 4 H), 2.94 (t. ./ 7.2 Hz, 2 H), 2.18-2.10 (m, 2 H), 1.29 (t, J= 12 Hz, 3 H)
  • 6
  • [ 2676865-17-9 ]
  • [ 2676865-18-0 ]
YieldReaction ConditionsOperation in experiment
92% With diisobutylaluminium hydride In tetrahydrofuran at -78 - 20℃; for 16h; 332a-d.3 To a stirred solution of ethyl 4-nitro-I,2,3,5,6,7-hexahydro-s-indacene-2-carboxylate (0.43 g, 1.6 mmol) in THF (20 mL) was added DIBAL-H (10 mL, 10 mmol) at -78 °C. Hie reaction was wairned to room temperature. After 16 h, the reaction was quenched with water (1 mL), 15% NaOH (1 mL) and water (2 ml), then dired with anhydrous Na?.SO^, filtered and concentrated under reduced pressure. The erode residue was purified by flash column chromatography (silica, 25% EtOAc in petroleum ether) to give (4-nitro- 1 ,2,3,5,6,7-hexahydro-s-indacen-2-yl)meihanol (0.35 g, yield: 92%) as a yellow' solid.lH NMR (400 MHz, CDC13): d = 7.30 (s, 1 H), 3.76-3.59 (m, 2 H), 3.48-3.35 (m, 1 H), 3.26 (t, J= 12 Hz, 2 H), 3 13-3 04 (m, 2 H), 2 94 (t, J= 7.6 Hz, 2 H), 2.85-2.70 (m, 2 H), 2.23-2.06 (m, 2 H).
  • 7
  • [ 2676865-17-9 ]
  • [ 2676865-19-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 16 h / -78 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 2.2: 1 h / 20 °C
  • 8
  • [ 2676865-17-9 ]
  • [ 2676865-20-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 16 h / -78 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 2.2: 1 h / 20 °C 3.1: 10% Pd/C; hydrogen / ethanol / 2 h / 25 °C
 

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