16274-34-3

Usage

Uses

Used in Pharmaceutical Industry:
1-Hydroxy-2-prenylnaphthalene is used as a potential anticancer agent for its ability to inhibit the growth of various cancer cells, making it a subject of interest in the development of new pharmaceuticals.
Used in Traditional Medicine:
1-Hydroxy-2-prenylnaphthalene is used as a natural remedy for its antibacterial, antifungal, and antiprotozoal properties, which have been recognized and utilized in traditional medicine.
Used in Dye Industry:
1-Hydroxy-2-prenylnaphthalene is used as a yellow pigment in the dye industry, leveraging its historical use as a dye.
While the potential applications of plumbagin are promising, its use is currently limited due to concerns about its toxicity. Ongoing research is essential to fully understand its pharmacological effects and to develop safe and effective applications in various industries.

Upstream product

• 90-15-3 α-naphthol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 78-79-5 isoprene 
• 87-41-2 2-benzofuran-1(3H)-one 
• 54109-51-2 ethyl 5-methyl-2-methylenehex-4-enoate 
• 20213-31-4 1-naphthyl prenyl ether 
• 115-18-4 2-methyl-3-buten-2-ol 
• 598-25-4 Dimethylallene 
• 574-00-5 1,2-Dihydroxynaphthalene 
• 870-63-3 prenyl bromide 

Downstream Products

• 16274-33-2 3,4-dihydro-2,2-dimethyl-2H-naphtho[1,2-b]-pyran 

Relevant academic research and scientific papers

Benzannulation for the regiodefined synthesis of 2-alkyl/aryl-1-naphthols: Total synthesis of arnottin i

The annulation of phthalides with α-alkyl/arylacrylates in the presence of LDA/LHMDS is shown to directly give alkyl/aryl-1-naphthols. The method involving a novel dealkoxycarbonylation obviates the regiochemical issues in the synthesis of polysubstituted naphthalenes, and it forms the key step in a three-step total synthesis of arnottin I, a naphthobenzopyranone natural product.

Benzylation and allylation of naphthols using amberlyst-15

A simple and efficient method has been developed for benzylation and allylation of naphthols by treatment of the compounds with benzylic and allylic alcohols, respectively, in the presence of amberlyst-15. Several heterogeneous catalysts were screened for

Bismuth triflate catalyzed [1,3] rearrangement of aryl 3-methylbut-2-enyl ethers

An efficient bismuth triflate catalyzed [1,3] rearrangement of aryl 3-methylbut-2-enyl ethers has been developed. The reaction proceeds rapidly and affords the corresponding para- and ortho-prenylated phenols and naphthols in moderate to good yields (up t

Water-Accelerated Claisen Rearrangements

Allyl aryl ethers undergo accelerated Claisen and [1,3] rearrangements in the presence of a mixture of trialkylalanes and water or aluminoxanes. The ratio of ortho-, meta-, and pora-Claisen products depends to a large extent on the presence of water and to a much lesser extent on the nature of the alane.

Synthesis and vasorelaxant activity of 4-(cyclic amido)-2H-naphtho[1,2-b]pyrans

A series of 4-(cyclic amido)-2H-naphtho[1,2-b]pyrans related to cromakalim (1) has been prepared and their vasorelaxant activities on isolated rat thoracic aorta precontracted with phenylephrine have been evaluated. The relaxant mechanism of 3a was found not through ATP-sensitive K+ channels as cromakalim, but through opening voltage-sensitive K+ channels.

Reaction between phenols and isoprene under zeolite catalysis. Highly selective synthesis of chromans and o-isopentenylphenols

Chromans 3 and o-isopentenylphenols 4 are synthesized in satisfactory to good yields and selectivities by the reaction of phenols and isoprene in the presence of the commercially available acid faujasite zeolite HSZ-360.

REGIOSPECIFIC CATALYTIC ALKENYLATION OF AROMATIC SUBSTRATES WITH COORDINATED DIENES: REACTIONS ON NAPHTHALENE DERIVATIVES. PRELIMINARY RESULTS ON HETEROAROMATIC SUBSTRATES

α- and β-naphthol undergo regiospecific alkenylation by 1,1-dimethylallene (DMA) at the OH-adjacent β- and α-positions, respectively, when allowed to react with DMA-Pt(II) complex.A catalytic process can be achieved with conversions higher than 90percent.A Pd(II) complex as promotor and isoprene as alkenylating diene can also be used.Similar results were obtained with N-acetyl-β-naphthylamine.Preliminary results indicated that nitrogen-containing heteroaromatic substrates can afford N-, O- or C-isopentenyl derivatives depending on the particular features of the organic ring.

Selective Allylation of Sodium Naphtholate

The reaction of 1- or 2-naphthol with allylic halides (1-chloro-3-methyl-2-butene, 1-chloro-3,7-dimethyl-2,6-octadiene, trans-1-chloro-2-butene and trans-1-chloro-2-hexene) in the presence of metallic sodium gave naphthols having the corresponding allylic group selectively.

TWO NAPHTHOPYRAN DERIVATIVES FROM FARAMEA CYANEA

Four anthraquinones and two new products, faramol (3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-naphthopyran) and 7-methoxyfaramol (3,4-dihydro-3-hydroxy-7-methoxy-2,2-dimethyl-2H-naphthopyran), have been isolated from Faramea cyanea. Key Word Index - Faramea cyanea; Rubiaceae; naphthopyrans; anthraquinones; lichexanthone.

SILICON-MEDIATED C-ISOPRENYLATION OF PHENOLS

C-isoprenylation of phenols has been effected using a combination of isoprene and in situ generated iodotrimethylsilane or hydrogen iodide.