15874-80-3

Basic information

• Product Name: Benzene, [(3-methyl-2-butenyl)sulfonyl]-
• CAS NO: 15874-80-3
• Molecular Formula: C11H14O2S
• Molecular Weight: 210.297
• Mol File: 15874-80-3.mol

Chemical Properties

• CAS DataBase Reference: Benzene, [(3-methyl-2-butenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(3-methyl-2-butenyl)sulfonyl]-(15874-80-3)
• EPA Substance Registry System: Benzene, [(3-methyl-2-butenyl)sulfonyl]-(15874-80-3)

Safety Data

• Hazardous Substances Data: 15874-80-3(Hazardous Substances Data)

Upstream product

• 873-55-2 sodium benzenesulfonate 
• 870-63-3 prenyl bromide 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 556-82-1 3-methyl-2-buten-1-ol 
• 15543-64-3 prenyl tolyl sulfone 
• 72863-21-9 (dimethyl-1,1 propene-2 yl) sulfonyl-1 methyl-4 benzene 
• 72863-20-8 α,α-Dimethylallyl phenyl sulfone 
• 38442-51-2 tert-butylmercury chloride 
• 119305-97-4 3-methylbut-2-enyl toluene-p-sulphinate 
• 115125-70-7 3-(tert-butylsulfonyl)-3-methylbut-1-ene 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 
• 78-84-2 isobutyraldehyde 
• 618-41-7 Benzenesulfinic acid 
• 78-79-5 isoprene 

Downstream Products

• 52449-21-5 Phenylsulfonyl-⁽⁵⁾-dimethyl-(3,7)-octadien-(1,6)-ol-3 
• 51361-64-9 2-chloro-6-methyl-4-(phenylsulphonyl)-1,5-heptadiene 
• 68470-86-0 5-Benzenesulfonyl-2,7-dimethyl-octa-2,6-dien-4-one 
• 1071175-48-8 4-Benzenesulfonyl-3,3,6-trimethyl-hept-5-enoic acid ethyl ester 
• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 74866-54-9 2-methyl-4-(phenylsulfonyl)-(E)-2-octene 
• 84602-94-8 1,1-dichloro-3-methyl-2-butenyl phenyl sulfone 
• 84602-96-0 [Dichloro-(2-chloro-3,3-dimethyl-cycloprop-1-enyl)-methanesulfonyl]-benzene 
• 84602-86-8 2-methyl-4-(phenylsulphonyl)-2-hexene 
• 22539-80-6 diethyl (3-methylbut-2-enyl)malonate 
• 758-66-7 diethyl 2-(2-methylbut-3-en-2-yl)malonate 
• 103904-63-8 4-Benzenesulfonyl-2-methyl-tridec-2-en-5-ol 
• 78828-39-4 3-(1-Benzenesulfonyl-3-methyl-but-2-enyl)-cyclohexanone 
• 68560-64-5 2-methyl-4-(phenylsulfonyl)dec-2-ene 

Relevant articles and documents

Carbon Dioxide-Promoted Telomerization of 1,2- and 1,3-Dienes with Benzenesulfinate Catalyzed by Palladium(0)

The telomerization of 1,2- and 1,3-dienes with benzenesulfinate dihydrate catalyzed by palladium(0) has been promoted by the presence of carbon dioxide

Development of a new air-stable structure-simplified nafuredin-γ analog as a potent and selective nematode complex I inhibitor

Nafuredin-γ, obtained from natural nafuredin, has demonstrated a potent and selective inhibitory activity against nematode complex I. However, nafuredin-γ is unstable in air since its conjugated dienes are oxygen-labile. The instability in air was natural

Palladium-catalyzed substitution of allylic alcohols with sulfinate salts: A synthesis of bicalutamide

A method is presented for the direct substitution of allylic alcohols with sodium arylsulfinates. The process involves a cooperative action of palladium catalysts, phenylboronic acid and titanium tetraisopropoxide. By taking advantage of this protocol, we achieved a concise synthesis of bicalutamide, an anti-androgen compound for treating prostate cancer.

CHINONE-, HYDROCHINOME- AND NAPHTHOCHINONE-ANALOGUES OF VATIQUIONE FOR TREATMENT OF MITOCHONDRIAL DISORDER DISEASES

The disclosure provides therapeutic compositions (i.e., therapeutic agents) and methods of preventing or treating Friedreich's ataxia in a mammalian subject, reducing risk factors, signs and/or symptoms associated with Friedreich's ataxia (e.g. Complex I deficiency), and/or reducing the likelihood or severity of Friedreich's ataxia. The disclosure further provides novel intermediates for the production of said therapeutic compositions and related reduced versions of said therapeutic compositions, which reduce forms may also be used as therapeutic agents (or prodrugs of the therapeutic agent(s)).

Synthesis of Sulfones and Sulfonyl Derivatives using Sodium (tert-butyldimethylsilyl)oxymethanesulfinate

The present invention relates to a method for manufacturing a sulfone and sulfonyl derivative compound using sodium (tert-butyldimethylsilyl)oxymethanesulfinate, which is a novel organic sulfin salt, wherein the novel organic sulfin salt has good stability, environmental friendliness and economy, and is easy to handle, and thus significantly reduces the amount of transition metal catalysts and the amount of organic sulfin salts used when introducing aryl or alkenyl. Also, alkylation, arylation, amination, and fluorination are all possible during secondary functionalization. Therefore, the present invention can be usefully used in preparation and mass production of various kinds of sulfones and derivatives thereof including asymmetric sulfone derivatives.

A General Photocatalytic Route to Prenylation

Prenylation is an essential reaction on which nature relies to modify properties of molecules and build terpenoids, but remains a challenging chemical reaction. Aiming to capitalize on recent advances in photocatalysis to easily and cleanly generate a broad range of carbon based radicals, we have developed a prenyl transfer reagent that is captured by transiently generated radicals. The reagent can be made in bulk, is bench stable, and broadly applicable such that it can be used with existing photocatalytic methods with very few changes to reaction conditions. Ultimately, this provides a true drop-in solution for prenylation, expanding the scope of substrates that can be readily prenylated.

Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives

An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium tert-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO22-) equivalent. TBSOMS-Na, easily prepared from the commercial reagents Rongalite and TBSCl, serves as a potent nucleophile in S-alkylation and Cu-catalyzed S-arylation reactions with alkyl and aryl electrophiles. The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a separate unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.

Bimolecular Cross-Metathesis of a Tetrasubstituted Alkene with Allylic Sulfones

Exquisite control of catalytic metathesis reactivity is possible through ligand-based variation of ruthenium carbene complexes. Sterically hindered alkenes, however, remain a generally recalcitrant class of substrates for intermolecular cross-metathesis.

Squalene-Hopene Cyclase: On the Polycyclization Reactions of Squalene Analogues Bearing Ethyl Groups at Positions C-6, C-10, C-15, and C-19

Squalene-hopene cyclase (SHC) has been found to convert acyclic squalene into 6,6,6,6,5-fused pentacyclic triterpenes hopene and hopanol. The enzymatic reactions of squalene analogues bearing ethyl groups in lieu of methyl groups at positions C-6, C-10, C-15, and C-19 have been examined to investigate whether the larger ethyl substituents (a C1 unit increment) are accepted as substrates and to investigate how these substitutions affect polycyclization cascades. Analogue 6-ethylsqualene 19a did not cyclize, which indicates that substitution with the bulky group at C-6 completely inhibited the polycyclization reaction. In contrast, 19-ethylsqualene 19b afforded a wide spectrum of cyclization products, including mono-, bi-, tetra-, and pentacyclic products in a ratio of 6:6:1:2. The production of tetra- and pentacyclic scaffolds suggests that the reaction cavity for D-ring formation site is somewhat loosely packed and can accept the 19-ethyl group, and that a robust hydrophobic interaction exists between the 19-ethyl group and the binding site. In contrast to 19b, 10-ethylsqualene 20a and 15-ethylsqualene 20b afforded mainly mono- and bicyclic products, that is, the polycyclization cascade terminated prematurely at the bicyclic reaction stage. Therefore, the catalytic domains for the 10- and 15-methyl binding sites are tightly packed and cannot fully accommodate the Et substituents. The cyclization pathways followed by the ethyl-substituted substrates in the presence of SHC and lanosterol and β-amyrin synthases are compared.

β-Amyrin Biosynthesis: Effect of Steric Bulk at the 6-, 10- and 15-Positions in the 2,3-Oxidosqualene Backbone on Polycyclisation Cascades

β-Amyrin synthase incubation experiments have been conducted to determine the influence of steric effects at the 6-, 10- and 15-positions of 2,3-oxidosqualene on the polycyclisation pathway. Nor- and ethyl-substituted oxidosqualene analogues were synthesised. Cyclisation of the ethyl-substituted analogues did not occur, but the nor analogues underwent a polycyclisation cascade to yield fully cyclised products with 6/6/6/6/6-fused pentacyclic scaffolds generated via a final oleanyl cation. Previously, we reported that 19- and 23-ethyl-substituted analogues underwent polycyclisation reactions. Therefore, the catalytic domain involved in earlier cyclisation steps is notably compact. In contrast, the catalytic domain in the later cyclisation steps is more loosely packed (less compact) to accommodate the bulky ethyl group. The reaction cavities for recognising branched methyl groups are discussed by comparing β-amyrin synthase with other triterpene cyclases such as lanosterol and hopene synthases.