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Chemical Structure| 955117-18-7 Chemical Structure| 955117-18-7

Structure of 955117-18-7

Chemical Structure| 955117-18-7

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Product Details of [ 955117-18-7 ]

CAS No. :955117-18-7
Formula : C24H24N2O
M.W : 356.46
SMILES Code : N(=CC=CC1=CC=CC=C1)[C@@]\23C4=C(C[C@@H](/C2=C\C)C=C(C)C3)NC(=O)C=C4
MDL No. :N/A

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* 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 [ 955117-18-7 ]

[ 955117-18-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 92138-20-0 ]
  • [ 104-55-2 ]
  • [ 955117-18-7 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; for 3h;Heating / reflux; Example 2 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 20 mg Huperzine A, and 77 mg cinnamaldehyde were refluxed in 2 mL isopropanol for 3 hours. Solvent was removed under vacuum. The crude reaction mixture was dissolved in 3 mL anhydrous THF and purified with prep. TLC (CHCl3: methanol=9:1) to give 28 mg of title product. MS: 357 (M+H).
In isopropyl alcohol; for 3h;Heating / reflux; Example 2 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 20 mg of Huperzine A, 77 mg of cinnamaldehyde were refluxed in 2 mL of isopropanol for 3 hours, and then solvent was removed under vacuum, 3 mL of anhydrous THF added and purified with prep. TLC (CHCl3: methanol=9:1) to give 28 mg of title product. MS: 357 (M+H).
  • 2
  • [ 955117-18-7 ]
  • [ 92138-20-0 ]
YieldReaction ConditionsOperation in experiment
With artificial gastric fluid; for 0.25 - 3.83333h;Conversion of starting material; Studies of the release of Huperzine A by H064-5-2 (title compound of Example 2, (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one) in artificial gastric fluidInstruments and ReagentsHPLC: Shimadzu SCL-10Avp, LC-10Atvp pump, SPD-M10Avp, DGU-14A. UV-VIS spectrophotometer: SHIMADZU UV-260. Huperzine A check sample (purity 99%). H064-5-2 (title compound of Example 2, (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one): prepared by Tianjin Hemay BioTech Co. Ltd). Methanol (chromatographic grade). Purified H2O. All other reagents are analytically pure.Experiment and Results1) Determination of wavelength: 1 mg cinnamaldehyde, 1 mg H064-5-2 and 1 mg Huperzine A check sample were precisely measured out. Methanol was then added to obtain a constant volume of 10 mL. 0.5 mL solution was subsequently taken out from the original solution to obtain a constant volume of 10 mL by adding methanol. Samples were scanned at 190-500 nm to identify absorption with methanol as blank. The results are the following: absorption peaks of H064-5-2 are 204.4 nm and 286.8 nm. The absorption peaks of cinnamaldehyde are 205.8 nm, 210.6 nm, 223.2 nm and 285.0 nm. The absorption peaks of huperzine A are 202.2 nm, 228.6 nm, 311.0 nm, 354.2 nm and 373.6 nm.Conclusion: H064-5-2 has characteristic absorption peak at 287 nm.2) Chromatography conditions: C18 (150×4.6 mm, 5 mum), methanol/water (1:1) as mobile phase containing 0.02% triethanolamine. Flow rate 1 mL/min. Detection conditions are the following: detector: SPD-M10Avp. Detection wavelength: 287 nm. Injected sample volume: 20 mul.3) Blank test: 0.3 mL grastric fluid was extracted, and 5 mL methanol was added to obtain a constant volume, injected sample volume is 20 mul, there are no peaks appearing at the retention times of the control sample.4) Chromatogram of Huperzine A:A) 1.0 mg Huperzine A check sample was precisely measured and added in a 10 mL volumetric flask; methanol was added to obtain a constant volume. 0.05 mL was then precisely extracted and 10 mL methanol was added to obtain a 10 mL constant volume, the injected sample volume is 20 mul. The chromatogram was recored.B) 1.0 mg Huperzine A check sample was precisely measured and added in a 10 mL volumetric flask, gastric fluid was added to get a constant volume. 0.05 mL was taken out and methanol was added to get a constant volume of 10 mL with 0.5 ng/mul. The injected sample volume is 20 mul. Chromatogram was recorded.5) Chromatogram of cinnamaldehyde: a small volume of cinnamaldehyde check sample was dissolved in methanol, and its chromatogram was recorded.6) Standard curve: 1.0 mg Huperzine A check sample was precisely measured and added into a 10 mL volumetric flask, methanol was added to get a constant volume. 0.05 mL was taken out and methanol was added to it to get a constant volume of 10 mL, the concentration of which is 0.5 ng/mul. 2, 4, 5, 10, 25, and 50 mul solution were separately taken out, and injected according to the above stated chromatographic conditions. After linear regression analysis, the standard curve was plotted with the injected volume (ng) of huperzine A check sample as Y-axis, the area of main peak as x-axis. The results are shown in the Table 1; 7) Sample measurement: 1.0 mg H064-5-2 sample was precisely measured, dissolved in gastric fluid with 2 min ultrasound; a constant volume of 10 mL with the concentration of 0.1 mg/mL was then obtained. 0.03 mL was precisely extracted at prescribed times, and methanol was added to get a constant volume of 5 mL, which was measured. The main peak area of Huperzine A was recorded, and the concentration was determined to be 0.6 ng/mul. The injected sample volume was 20 mul (12 ng). The results are listed in Table 2 and in FIG. 1.
 

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