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[ CAS No. 56013-01-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 56013-01-5
Chemical Structure| 56013-01-5
Structure of 56013-01-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 56013-01-5 ]

CAS No. :56013-01-5 MDL No. :
Formula : C28H32BrP Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 479.43 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 56013-01-5 ]

* 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 [ 56013-01-5 ]

[ 56013-01-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 40834-42-2 ]
  • [ 56013-01-5 ]
  • [ 14398-44-8 ]
  • 2
  • [ 472-20-8 ]
  • [ 6399-81-1 ]
  • [ 56013-01-5 ]
YieldReaction ConditionsOperation in experiment
78% In methanol; at 20℃; for 18h; To a stirred solution of <strong>[6399-81-1]triphenylphosphine hydrobromide</strong> (20.0 g, 58.3 mmol) in MeOH (50 mL) was added a solution of 23 (8.99 g, 58.4 mmol) in methanol (40 mL) and the reaction mixture stirred at room temperature for 18 h. The reaction solution was concentrated under reduced pressure, the residue triturated with a mixture of acetone (15 mL) and diethyl ether (200 mL) and the solvent decanted. The resulting residue was then triturated with a mixture of acetone (10 mL), ethyl acetate (50 mL) and diethyl ether (300 mL) and the solvent decanted again. The residue was dried in vacuo to provide coupling triphenyl((2,6,6- trimethylcyclohex- 1 -enyl)methyl)phosphonium bromide (26) as a white foam. Yield (21.9 g, 78%: 1H NMR(500 MHz, DMSO-d6) delta 7.90-7.70 (m, 15H), 4.30 (d, J= 15.1 Hz, 2H), 2.02 (m, 2H), 1.61 (d, J= 5.7 Hz, 3H), 1.54 (m, 2H), 1.37 (m, 2H), 0.72 (s, 6H); ESI MS m/z 399 [M - Br]+.
With sodium tetrahydroborate; In methanol; for 72h;Inert atmosphere; Synthesis of 11-cis-7-ring retinals was performed as described previously with some modifications (Fujimoto et al., Chirality 14:340-46 (2002); Akito et al., J. Am. Chem. 102:6370-72 (1980); Caldwell et al., J. Org. Chem. 58:3533-37 (1993). All of the reactions were performed in a dried nitrogen atmosphere unless otherwise specified. 2-Cycloheptenone was first converted into allyl acetate by N-bromosuccinimide bromination in CCl4 followed by treatment with KOAc in hexamethylphosphoramide. Purified 4-acetoxy-2-cycloheptenone (46% from 2-cycloheptenone) was subjected to a Horner-Emmons reaction with diethyl (2-cyanoethyl)phosphonate, which gave an isomeric mixture of two trans/cis (E/Z) cyanoacetates in a 2:1 ratio. The mixture was hydrolyzed with K2CO3 in MeOH:H2O (5:1), and then the hydroxy group of the resulting allylic alcohol was protected with tert-butyldimethylsilyl chloride in pyridine (80% from cycloheptenonyl acetate). The resulting cyano compound was reduced with diisobutylaluminium hydride in CH2Cl2 to an aldehyde and purified by flash chromatography on a silica gel (63%). beta-Cyclocitral was reduced with. NaBH4 to beta-cyclogeraniol and then reacted with <strong>[6399-81-1]triphenylphosphine hydrobromide</strong> in MeOH over 3 days to afford beta-cyclogeranyltriphenylphosphonium bromide after the removal of solvent and drying of the residue in vacuum. Wittig reaction of the silylated aldehyde with an excess of phosphonium salt in the presence of potassium tert-butoxide and a catalytic amount of 18-crown-6 in methylene chloride at ambient temperature afforded protected cyclic alcohol in 75% yield. The tert-butyldimethylsilyl protecting group was removed by treatment with tetrabutylammonium fluoride in dry THF, and the resulting alcohol was oxidized with MnO2 in CH2Cl2 to a mixture of two (E/Z) cyclic ketones (2:1 ratio) in 96% yield. This mixture was condensed with triethyl phosphonoacetate under Homer-Emmons conditions, followed by lithium aluminum hydride reduction of the resulting isomeric mixture of ethyl 7-ring retinoates and oxidation of retinols with MnO2 (86%) in CH2Cl2.
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