4488-59-9

Usage

Uses

Used in Organic Synthesis:
(1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl chloroacetate is used as a reagent in organic synthesis for the preparation of various organic compounds. Its unique structure and reactivity contribute to the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl chloroacetate is used for the synthesis of active pharmaceutical ingredients. Its specific stereochemistry and functional groups make it a valuable component in the development of new drugs.
Used in Fragrance and Flavoring Industry:
(1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl chloroacetate may have potential applications as a fragrance or flavoring agent. Its unique chemical structure could contribute to the creation of novel scents and tastes in the fragrance and flavoring industries.

Upstream product

• 464-45-9 endo-borneol 
• 79-11-8 chloroacetic acid 
• 464-43-7 d-borneol 
• 79-04-9 chloroacetyl chloride 
• 464-48-2 (1S)-camphor 
• 124-76-5 isoborneol 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 464-43-7 borneol 
• 507-70-0 1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol 
• 80-56-8 rac-α-pinene 

Downstream Products

• 20314-75-4 (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-morpholinoacetate 
• 20314-75-4 (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-morpholinoacetate 
• 39850-78-7 5-Ketoborneol 
• 509-08-0 isovaleryloxy-acetic acid isobornyl ester 

Relevant academic research and scientific papers

Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process

In this study, we screened a large library of (+)-camphor and (?)-borneol derivatives to assess their filovirus entry inhibition activities using pseudotype systems. Structure-activity relationship studies revealed several compounds exhibiting submicromolar IC50 values. These compounds were evaluated for their effect against natural Ebola virus (EBOV) and Marburg virus. Compound 3b (As-358) exhibited the good antiviral potency (IC50 = 3.7 μM, SI = 118) against Marburg virus, while the hydrochloride salt of this compound 3b·HCl had a strong inhibitory effect against Ebola virus (IC50 = 9.1 μM, SI = 31) and good in vivo safety (LD50 > 1000 mg/kg). The results of molecular docking and in vitro mutagenesis analyses suggest that the synthesized compounds bind to the active binding site of EBOV glycoprotein similar to the known inhibitor toremifene.

PHENYLPROPIONATE COMPOUND, PREPARATION METHOD FOR SAME, AND APPLICATIONS THEREOF

Provided in the present invention are a phenylpropionate compound, a preparation method for same, and applications. The phenylpropionate compound has the structure as represented by formula I. The phenylpropionate compound of the present invention, a pharmaceutically acceptable salt, a solvate, a prodrug, and a tautomer or stereochemical isomer or pharmaceutical composition of the compound provide improved anti-inflammatory and antiplatelet effects and, at the same time, provide an extended time window for treatment, are free of obvious side effects, safe and effective, applicable in an antithrombus, anti-inflammatory, and cerebral stroke treating medicament, and have broad application prospects.

Phenylacrylate compound as well as preparation method and application thereof

The invention provides a phenylacrylate compound as well as a preparation method and application thereof. The phenylacrylate compound has the structure shown in a formula I. The phenylacrylate compound and pharmaceutically acceptable salt, solvent compound, predrug, tautomer or stereoisomer or medicinal composition thereof have good anti-inflammatory and antiplatelet effects, have a long treatmenttime window, do not have remarkable side effect, is safe and effective, can serve as antithrombus, anti-inflammatory and stroke-treating medicines and have wide application prospects.

Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus

Herein, we present the design and synthesis of a series of novel heterocyclic derivatives of (-)-borneol and (-)-isoborneol as potent inhibitors of the influenza A virus. All compounds were tested for their toxicity against MDCK cells and for virus-inhibiting activity against the influenza virus A/Puerto Rico/8/34 (H1N1). Compounds 7, 16 and 26 containing a morpholine fragment exhibited the highest efficiency as agents inhibiting the replication of the influenza virus A(H1N1) with selectivity indices of 82, 45 and 65, correspondingly. Derivatives 9 (SI = 23) and 18 (SI = 25) containing a 1-methylpiperazine motif showed moderate antiviral activity. Structure-activity analysis of this new series of borneol derivatives revealed that a 1,7,7-trimethylbicyclo[2.2.1]heptan scaffold is required for the antiviral activity.

Synthesis and biological activity of heterocyclic borneol derivatives

(figure presented) A series of novel heterocyclic derivatives of (–)-borneol has been prepared by the interaction of (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-yl 2-chloroacetate and (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 3-chloropropanoate with different N- and S-nucleophiles. The obtained products were screened for antiviral, antiulcer, and analgesic activity.

S-Substituted-2-mercaptobenzthiazolium-based chiral ionic liquids: efficient organocatalysts for enantioselective sodium borohydride reductions of prochiral ketones

Novel chiral ionic liquids having chirality in their cationic part have been synthesized for evaluation of their catalytic potential as organocatalysts in sodium borohydride reduction of prochiral ketones to yield optically active secondary alcohols. The chiral ionic liquids have been synthesized from the reaction of (?)-menthol or (?)-borneol, chloroacetic acid and S-methyl/benzyl-2-mercaptobenzthiazole. The synthesized chiral ionic liquids have been characterized by 1H, 13C NMR and Mass spectrometry. Moderate to excellent enantiomeric excess (ee?>?99%) has been obtained in asymmetric sodium borohydride reduction of prochiral ketones using these salts as chiral catalysts.

New benzimidazolium-based chiral ionic liquids: Synthesis and application in enantioselective sodium borohydride reductions in water

New chiral ionic liquids based on benzimidazolium salts have been synthesized from the reaction of (-)-menthol or (-)-borneol, chloroacetic acid and 1-methylbenzimidazole. The structures of these chiral ionic liquids have been confirmed from 1H

Danshensu mixes turns on lathe to a method for the synthesis of

The invention relates to a synthesis method of racemic bornyl beta-(3,4-dihydroxyphenyl)-alpha-hydroxypropionate. The method comprises the following steps: carrying out Darzens epoxidation on an initial raw material benzyl protected protocatechualdehyde, and carrying out palladium catalyst/hydrogen or Raney nickel/hydrogen catalytic reduction to obtain racemic bornyl beta-(3,4-dihydroxyphenyl)-alpha-hydroxypropionate. The purity and the yield of a product synthesized by adopting the method reach 98% and 48.6% respectively. The synthesis method has the advantages of simple and easily available raw material, short route, high yield, and suitableness for large scale industrialized production.

Cyclopentadienyl molybdenum alkyl ester complexes as catalyst precursors for olefin epoxidation

New molybdenum complexes of the type [CpMo(CO)3X] containing ligands of the formula X = CHR2CO(OR1) where R1 = ethyl (1), menthyl (4), and bornyl (5) and R2 = H; R1 = ethyl and R2 = methyl (2) and phenyl (3) have been synthesized and characterized by NMR and IR spectroscopy and X-ray crystallography. These compounds have been applied as catalyst precursors for achiral and chiral epoxidation of unfunctionalized olefins with tert-butyl hydroperoxide (TBHP) as the oxidant at 22 °C (in CH2Cl2) and 55°C (in CHCl3). The substrates cis-cyclooctene, 1-octene, cis- and trans-stilbene, and trans-β-methylstyrene were selectively and quantitatively converted into their epoxides using a catalyst:substrate:oxidant ratio of 1:100:200 within 4 h at room temperature in CH2Cl2 and within 15 min at 55°C in CHCl3. Complexes 1-5 are precursors of active epoxidation catalysts and turnover frequencies (TOFs) of ca. 1200 h-1 are obtained with cis-cyclooctene as the substrate. No enantioselectivity is observed with trans-β-methylstyrene as the substrate despite the application of enantiomerically pure precatalysts. In situ monitoring of catalytic epoxidation of cis-cyclooctene with complex 5 by 1H and 13C NMR spectroscopy suggests that the chiral alkyl ester side chain is retained during oxidation with TBHP. During epoxidation, the primary catalytic species is the dioxo complex [CpMoO2X]. After near complete conversion of cis-cyclooctene to its epoxide, further oxidation of the dioxo complex to oxo-peroxo complex [CpMo(η2-O2)(O)X] takes place. The oxo-peroxo complex is also an active epoxidation catalyst.

Stereoselective oxidation of methyl phenyl sulfide in the presence of chiral ionic liquids

Several ionic liquids containing a chiral center either in the cation or in the anion have been prepared. They have been applied as catalysts and solvents for stereoselective oxidation of methyl phenyl sulfide to obtain the respective sulfoxide.