6213-89-4

Usage

Uses

Used in Organic Synthesis:
(E-3-BROMOACRYLIC ACID is used as a reagent in organic synthesis for its ability to facilitate the preparation of pharmaceuticals and other fine chemicals. Its unique properties allow it to be a key component in the creation of a wide range of organic compounds.
Used in Pharmaceutical Production:
(E-3-BROMOACRYLIC ACID is used as a building block in the synthesis of pharmaceuticals, contributing to the development of new and improved medications. Its role in this industry is crucial for the advancement of medical treatments and therapies.
Used in the Production of Polymers and Advanced Materials:
(E-3-BROMOACRYLIC ACID is used as a starting material for the production of polymers and other advanced materials, highlighting its importance in material science and the development of innovative products with enhanced properties.
Used in Research and Development:
(E-3-BROMOACRYLIC ACID is utilized in research and development settings to explore new chemical reactions and syntheses, further expanding the horizons of organic chemistry and its applications across different industries.

Upstream product

• 1609-92-3 (Z)-3-bromoacrylic acid 
• 471-25-0 Propiolic acid 

Downstream Products

• 6213-87-2 methyl (2E)-3-bromoacrylate 
• 22038-50-2 trans-2-Carboxy-vinyl-triphenylphosphoniumbromid 
• 84304-03-0 5-Benzyloxymethyl-4-bromo-5H-furan-2-one 
• 140-10-3 (E)-3-phenylacrylic acid 
• 37428-55-0 (E)-3-bromoprop-2-en-1-ol 
• 75-07-0 acetaldehyde 
• 40559-99-7 benzyl (E)-3-bromoprop-2-enoate 

Relevant academic research and scientific papers

Structure-Proving Syntheses of the Polyenoyltetramic Acids Pyranonigrin J and I

The polyenoyltetramic acids pyranonigrin J (3) and pyranonigrin I (4) had been isolated from Aspergillus niger. Their origins from and roles in biosynthesis as well as the S-configurations of their stereocenter had been deduced from expression experiments with modifications of the corresponding gene cluster. We corroborated this stereochemical assignment after executing the first total syntheses of both compounds because they had essentially the same specific rotations as their natural counterparts. Our syntheses used the β-ketothioester 18 as a conjunctive reagent. It was combined with the l-serine derivatives (S)-19 or (S)-21 (“Western building blocks”), respectively, through aminolyses. Stille couplings with the stannane 13 (“Eastern building block”) followed. The resulting β-ketoamides (S)-11 and (S)-12 underwent desilylative Lacey-Dieckmann cyclizations when exposed to 8 equiv. of Bu4NF. They rendered the polyenoyltetramic acids (S)-26 [acidolysis: → (S)-3] and (S)-4, respectively.

Stereostructure Clarifying Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone B. A Highly Acid-Labile N-Protecting Group for Amides ?

The 5S, 8′R, and 10′R configurations of militarinone B (3), which is a natural product from Paecilomyces militaris, should equal those in its biosynthetic precursor, militarinone C. The configuration at C-1′ emerged from syntheses of the militarinone B candidates 1′′S- and 1′′R-(5S,8′R,10′R)-3 from the building blocks 9, 11, 14, and 15a while introducing TMB as a more acid-labile N-protecting group for β-ketoamides than DMB. Comparisons of 1′′S- and 1′′R-(5S,8′R,10′R)-3 with natural militarinone B (3; reisolated from Nature) revealed identity versus distinctness.

Structure-Elucidating Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone C §

The (polyenoyl)tetramic acid militarinone C (1) heads a family of seven members. Before our work, the configuration of C-5 was unknown whereas the configurations of C-8′ and C-10′ were either (R,R) or (S,S). We synthesized the four stereoisomers of constitution 1, which conform with these insights. This included cross-coupling both enantiomers of the western building block (8) with both enantiomers of the eastern building block (9). The specific rotations of the resulting 1 isomers suggested that natural 1 is configured like the coupling partners (S)-8 and (R,R)-9. This conclusion was corroborated by degrading natural 1 to alcohol 35 and by proving its configurational identity with synthetic (R,R)-35.

Total Synthesis of Asparenydiol by Two Sonogashira Cross-Coupling Reactions Promoted by Supported Pd and Cu Catalysts

Asparenydiol, which is an important natural compound with potential pharmacological activities, was synthesized through two Sonogashira cross-coupling reactions catalyzed by supported Pd and Cu catalysts and by a Mitsunobu etherification. The optimization

Borylation and rearrangement of alkynyloxiranes: A stereospecific route to substituted α-enynes

1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangement of the so-formed alkynyloxiranyl borates. This stereospecific process overall transfers the cis or trans-stereochemistry of the starting alkynyloxiranes to the resulting 1,3-enynes.

QUINAZOLINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND PHARMACEUTICAL COMPOSITION AND APPLICATION THEREOF

Disclosed are a quinazoline derivative, a preparation method therefor, and a pharmaceutical composition and an application thereof. The present invention provides a compound represented by general formula I, a stereoisomer thereof and a pharmaceutical acceptable salt or a solvate thereof. The quinazoline derivative of the present invention has a unique chemical structure, is characterized by irreversibly inhibiting EGFR tyrosine kinase, has high biological activity, apparently improves the inhibiting effect on the EGFR tyrosine kinase, has quite strong tumor inhibiting effect on tumor cells and a transplantation tumor pathological model of animal tumors, and has good market developing prospects.

POLYFLUORINATED COMPOUNDS ACTING AS BRUTON TYROSINE KINASE INHIBITORS

Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.

Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration

Chiral secondary allylboronates are obtained in high enantioselectivities and 1,6:1,4 ratios by the copper-catalyzed 1,6-boration of electron-deficient dienes with bis(pinacolato)diboron (B2(pin)2). The reactions proceed efficiently using catalyst loadings as low as 0.0049 mol %. The allylboronates may be oxidized to the allylic alcohols, and can be used in stereoselective aldehyde allylborations. This process was applied to a concise synthesis of atorvastatin, in which the key 1,6-boration was performed using only a 0.02 mol % catalyst loading. 1,6-Borations of electron-deficient dienes with bis(pinacolato)diboron using copper catalyst loadings as low as 0.0049 mol % provided chiral allylboronates that, after oxidation, result in allylic alcohols in high enantioselectivities and 1,6:1,4 ratios. The allylboronates can also be used in stereoselective allylations of aldehydes. This process was applied to a concise synthesis of atorvastatin.

α- and β-Lipomycin: Total syntheses by sequential stille couplings and assignment of the absolute configuration of all stereogenic centers

40 years ago spectroscopy, derivatization, and degradation revealed the structures of α-lipomycin and its aglycon β-lipomycin except for the configurations of their side-chain stereocenters. We synthesized all relevant β-lipomycin candidates: the (12R,13S

3-Chloro-1-lithiopropene, a functional organolithium reagent, and its reactions with alkylboronates to give 3-alkylprop-1-en-3-ols

The reagent 3-chloro-1-lithiopropene (4) can be generated by treating 1-bromo-3-chloropropene with t-BuLi. It is unstable but if generated at low temperature in the presence of alkylboronic esters, such as 3, is trapped in situ to give rearrangement products 2, which on oxidation give 3-alkylprop-1-en-3-ols in good yields. The reaction works for primary, secondary, benzylic, and even tertiary alkylboronic esters, providing allylic alcohols bearing almost any alkyl group available using organoborane chemistry and incorporating all features of such groups.