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Chemical Structure| 560-09-8 Chemical Structure| 560-09-8
Chemical Structure| 560-09-8

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(1S,3R)-(-)-Camphoric acid is a low-activity isomer of camphoric acid that stimulates osteoblast differentiation and induces the expression of glutamate receptors, as well as activating NF-κB and AP-1.

Synonyms: (-)-Camphoric acid

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of (1S,3R)-(-)-Camphoric acid

CAS No. :560-09-8
Formula : C10H16O4
M.W : 200.23
SMILES Code : CC1(C)[C@@H](CC[C@]1(C)C(O)=O)C(O)=O
Synonyms :
(-)-Camphoric acid
English Name :(1S,3R)-1,2,2-Trimethylcyclopentane-1,3-dicarboxylic acid
MDL No. :MFCD00064937
InChI Key :LSPHULWDVZXLIL-QUBYGPBYSA-N
Pubchem ID :219463

Safety of (1S,3R)-(-)-Camphoric acid

Application In Synthesis of (1S,3R)-(-)-Camphoric acid

* 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 [ 560-09-8 ]

[ 560-09-8 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 560-09-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate; p-toluenesulfonyl chloride In ethyl acetate at 20℃; for 0.583333h;
85% With thionyl chloride; sodium carbonate In 1,4-dioxane; dichloromethane for 3.5h; Heating;
78% With 2-acetoxypropene; Montmorillonite KSF for 0.0333333h; Irradiation;
With acetyl chloride
With trifluoroacetic anhydride In dichloromethane at 15℃; for 19h; 1 Step 1: (1S, 5R) -1, 8, 8-trimethyl-3-oxabicyclo [3.2.1] octane-2, 4-dione (1S, 3R) -1, 2, 2-trimethylcyclopentane-1, 3-dicarboxylic acid (1 g, 4.99 mmol) in DCM (50 mL) was added 2, 2, 2-trifluoroacetic anhydride (3.15 g, 14.98 mmol) . Then the mixture was stirred at 15 for 19 hours. The mixture was concentrated to give the crude title compound.

  • 2
  • [ 560-09-8 ]
  • [ 79-03-8 ]
  • [ 1821799-27-2 ]
YieldReaction ConditionsOperation in experiment
34% With aluminium trichloride In nitromethane at 80℃; for 3h;
  • 3
  • [ 560-09-8 ]
  • [ 75-36-5 ]
  • [ 1931930-81-2 ]
YieldReaction ConditionsOperation in experiment
85.7% With aluminium trichloride In nitromethane at 80℃; for 3h;
  • 4
  • [ 560-09-8 ]
  • [ 141-75-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
63.8% With aluminium trichloride In nitromethane at 80℃; for 3h;
  • 5
  • [ 560-09-8 ]
  • [ 462628-19-9 ]
YieldReaction ConditionsOperation in experiment
95% With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; for 5h;
95% Stage #1: (1S,3R)-(-)-camphoric acid With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; for 5h; Heating / reflux; Stage #2: With water; sodium sulfate In tetrahydrofuran; diethyl ether for 0.5h; I.a; 1 To a solution of (1S,3R)-camphoric acid (1) (3.0 g, 14.8 mmol) in dryTHF (40 ml_) and dry Et2O (30 ml_) was added LiALH4 (2.0 g, 52.6 mmol) and the reaction mixture was refluxed for 5 hours. The reaction was then quenched by the addition of Na2SO4-IOH2O (8.5 g) and the mixture stirred for0.5 hour. H2O (100 mL) was added and the aqueous layer extracted withCH2CI2 (3 x 50 mL). The combined organic layers were dried over anhydrousMgSO4 and the solvents concentrated in vacuo to a residue which was purified over silica (n-hexane/EtOAc, 6:4) to afford 2.39 g (95% yield) of the desired intermediate (2) as crystals which were characterized as follows:- Rf (ϖ-hexane/ethyl acetate, 1 :1 ) 0.30;- optical rotation [α]Drt -56.6 (c = 1 , CHCI3);- infrared (IR) spectrum (KBr film): absorption bands at 3269, 2964, 1369, 1092 and 1023 cm"1;- proton nuclear magnetic resonance (hereinafter referred as 1H NMR) (500 MHz, CDCI3): chemical shifts at 3.73 (1 H, dd, J = 9.2, 5.6 Hz), 3.58 (1 H, d, J = 10.7 Hz), 3.51 (1 H, dd, J = 9.2, 9.1 Hz), 3.46 (1 H, d, J = 10.7 Hz), 2.08 (1 H, m), 1.95 (1 H, m), 1.59 (1 H, m), 1.21 (2 H, br m), 1.01 (6 H, s) and 0.79 (3 H, s) ppm;- mass spectrum MS m/z (%) 154 (M+ - H2O, 3), 139 (57), 123 (8), 109 (26), 81 (100) and 69 (88).
  • 6
  • [ 560-09-8 ]
  • [ 146502-77-4 ]
YieldReaction ConditionsOperation in experiment
51% With sodium azide; sulfuric acid In chloroform at 50℃; for 18h;
  • 7
  • [ 560-09-8 ]
  • [ 88150-42-9 ]
  • [ 1009012-68-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol at 20℃; for 21h; Heating / reflux; 4 3.0 g of racemic amlodipine and 1.11 g of (lS,3R)-camphoric acid were added to 30 mL of isopropanol and heated to be dissolved, followed by slowly cooling down the resultant solution to room temperature. The solution was allowed to stand undisturbed at room temperature for 21 hours to precipitate crystals. The precipitated crystals were extracted, collected, and dried under reduced pressure, to yield 0.81 g of (lS,3R)-camphoric acid salt of S-amlodipine. [45] Optical purity: S-amlodipine/R-amlodipine = 1.5/98.5
  • 8
  • [ 560-09-8 ]
  • [ 462628-28-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: 95 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 5 h / 20 °C 2: 86 percent / imidazole / dimethylformamide / 5 h / 0 - 20 °C 3: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 0 °C 4: 98 percent / NaH / tetrahydrofuran / 2 h / 0 °C 5: 95 percent / H2 / 10 percent Pd/C / hexane; ethyl acetate / 15 h / 20 °C / 3040 Torr 6: DIBALH / CH2Cl2 / 3 h / -78 °C 7: (COCl)2; DMSO; Et3N / CH2Cl2 / 4 h / -78 - 0 °C 8: 90 percent / t-BuOK / tetrahydrofuran / 15 h / -78 - 0 °C 9: LDA / tetrahydrofuran / 3 h / -40 - 10 °C 10: TBAF / tetrahydrofuran / 4 h / 20 °C 11: (COCl)2; DMSO; Et3N / CH2Cl2 / 4 h / -78 - 0 °C
 

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