22308-12-9

Basic information

• Product Name: 1,3-BIS(TOSYLOXY)-2,2-DIMETHYLPROPANE
• Synonyms: 1,3-Bis(p-toluenesulfonyloxy)-2,2-dimethylpropane 2,2-Dimethyl-1,3-propanediol Ditosylate Neopentyl Glycol Ditosylate;NEOPENTYL GLYCOL DITOSYLATE;2,2-DIMETHYL-1,3-PROPANEDIOL DITOSYLATE;1,3-BIS(TOSYLOXY)-2,2-DIMETHYLPROPANE;1,3-BIS(P-TOLUENESULFONYLOXY)-2,2-DIMETHYLPROPANE;Bistosyloxydimethylpropane
• CAS NO: 22308-12-9
• Molecular Formula: C₁₉H₂₄O₆S₂
• Molecular Weight: 412.52
• Mol File: 22308-12-9.mol

Chemical Properties

• Melting Point: 119.0 to 123.0 °C
• Boiling Point: 568.9°Cat760mmHg
• Flash Point: 297.9°C
• Appearance: /
• Density: 1.254g/cm³
• Vapor Pressure: 2.27E-12mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: 1,3-BIS(TOSYLOXY)-2,2-DIMETHYLPROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(TOSYLOXY)-2,2-DIMETHYLPROPANE(22308-12-9)
• EPA Substance Registry System: 1,3-BIS(TOSYLOXY)-2,2-DIMETHYLPROPANE(22308-12-9)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 22308-12-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,3-BIS(TOSYLOXY)-2,2-DIMETHYLPROPANE is used as a reagent for its strong acid catalytic properties, facilitating various organic reactions and contributing to the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Preparation:
In the pharmaceutical industry, 1,3-BIS(TOSYLOXY)-2,2-DIMETHYLPROPANE is used as a reagent in the synthesis of medicinal compounds, playing a crucial role in the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
Similarly, in agrochemical manufacturing, 1,3-BIS(TOSYLOXY)-2,2-DIMETHYLPROPANE serves as a reagent, aiding in the synthesis of various agrochemicals that are essential for agricultural applications.

InChI:InChI=1/C19H24O6S2/c1-15-5-9-17(10-6-15)26(20,21)24-13-19(3,4)14-25-27(22,23)18-11-7-16(2)8-12-18/h5-12H,13-14H2,1-4H3

Upstream product

• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 98-59-9 p-toluenesulfonyl chloride 
• 6315-52-2 1,2-bis-tosyloxyethane 
• 79-37-8 oxalyl dichloride 
• 75885-59-5 2,2-dimethylcyclopropane-1-carboxylic acid 
• 5722-11-2 rac-2,2-dimethylcyclopropanecarbonitrile 

Downstream Products

• 5722-11-2 rac-2,2-dimethylcyclopropanecarbonitrile 
• 66688-49-1 1-iodo-2-iodomethyl-2-methylpropane 
• 82777-31-9 Toluene-4-sulfonic acid 2,2-dimethyl-3-phenylsulfanyl-propyl ester 
• 37608-93-8 4,4-dimethyl-1-phenylpentan-1-one 
• 121955-71-3 5,5-dimethyl-2-phenylthio-1,3-diselenane 
• 16462-89-8 2,2-dimethyl-1-phenylsulphonylcyclopropane 
• 82777-32-0 2,2-dimethyl-3-phenylsulphonyl-1-tosyloxypropane 
• 75885-59-5 2,2-dimethylcyclopropane-1-carboxylic acid 
• 50675-57-5 dl-2,2-dimethylcyclopropane-1-carboxylic acid chloride 
• 75017-17-3 (3,3-dimethylcyclobutyl)methanol 
• 76207-24-4 (3,3-dimethylcyclobutyl)methyl-4-methylbenzene-1-sulfonate 
• 59671-39-5 1-(2,2-Dimethyl-cyclopropyl)-1-phenyl-ethanol 
• 61971-68-4 1-(2,2-Dimethyl-cyclopropyl)-1-(4-trifluoromethyl-phenyl)-ethanol 
• 61971-69-5 1-(3,5-Bis-trifluoromethyl-phenyl)-1-(2,2-dimethyl-cyclopropyl)-ethanol 

Relevant articles and documents

Probing hyperconjugation experimentally with the conformational deuterium isotope effect

Hyperconjugation underlies many chemical phenomena of fundamental and practical importance. Owing to a great deal of interest in the anomeric effect, anomeric-like hyperconjugative effects have been thoroughly investigated in oxygen-containing systems. However, such interactions in the second- and third-row chalcogens are less well-understood and have generated some controversy. Here, we show that the conformational deuterium isotope effect, in combination with Saunders isotopic perturbation method, permits sensitive and direct experimental probing of the conformational equilibria in dioxane, dithiane, and diselenane analogues by variable-temperature, dynamic NMR spectroscopy. We find that the magnitude of the conformational deuterium isotope effect is 252.1, 28.3, and 7.1 J/mol (±10%) for the oxygen, sulfur, and selenium analogues, respectively. These results reveal the periodic trend for hyperconjugation in the chalcogens, which reflect a decreasing n x→σC-H(D) interaction throughout the period, as supported by IR spectroscopy and in agreement with DFT calculations and a natural bond order analysis.

A Novel Phenylchromane Derivative Increases the Rate of Glucose Uptake in L6 Myotubes and Augments Insulin Secretion from Pancreatic Beta-Cells by Activating AMPK

Purpose: A series of novel polycyclic aromatic compounds that augment the rate of glucose uptake in L6 myotubes and increase glucose-stimulated insulin secretion from beta-cells were synthesized. Designing these molecules, we have aimed at the two main pathogenic mechanisms of T2D, deficient insulin secretion and diminished glucose clearance. The ultimate purpose of this work was to create a novel antidiabetic drug candidate with bi-functional mode of action. Methods: All presented compounds were synthesized, and characterized in house. INS-1E cells and L6 myoblasts were used for the experiments. The rate of glucose uptake, mechanism of action, level of insulin secretion and the druggability of the lead compound were studied. Results: The lead compound (6-(1,3-dithiepan-2-yl)-2-phenylchromane), dose- and time-dependently at the low μM range increased the rate of glucose uptake in L6 myotubes and insulin secretion in INS-1E cells. The compound exerted its effects through the activation of the LKB1 (Liver Kinase B1)-AMPK pathway. In vitro metabolic parameters of this lead compound exhibited good druggability. Conclusions: We anticipate that bi-functionality (increased rate of glucose uptake and augmented insulin secretion) will allow the lead compound to be a starting point for the development of a novel class of antidiabetic drugs.

Substituted pyrazolo-piperazines as casein kinase 1 δ/ε inhibitors

The invention provides compounds of Formula (I): and pharmaceutically acceptable salts thereof. The compounds of Formula (I) inhibit protein kinase activity thereby making them useful as anticancer agents.

Synthesis of C3- and C2-symmetric tris- and bis-sulfoxide ligands by asymmetric oxidation

A series of tris- and bis-sulfoxides were synthesized by multiple asymmetric oxidation of the corresponding sulfides. High enantioselectivities were obtained based on Horeau-type amplification of selectivity. Naphthyl-substituted sulfoxides allowed for higher selectivity and greater ease of purification. These sulfoxides were tested as ligands in rhodium-catalyzed olefin hydroacylation and 1,4-addition of phenyl boronic acid to 2-cyclohexen-1-one. While no enantioinduction was observed in hydroacylation, up to 80% ee was obtained for a tris-sulfoxide and a bis-sulfoxide ligand in the 1,4-addition. Bis-sulfoxides with flexible backbones gave lower and inversed enantioselectivity, suggesting backbone rigidity plays a key role in enantioinduction.

INHIBITORS OF ACETYL-COA CARBOXYLASE

The present invention relates to compounds that act as acetyl-CoA carboxylase (ACC) inhibitors. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

BENZO [b][1,4] DIOXEPINE DERIVATIVES

This invention relates to compounds of the formula (I), wherein B, X, Y, Z, R1 and R2 are as defined in the description, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are modulated by ACCβ inhibitors.

Benzodioxepine derivatives

This invention relates to compounds of the formula wherein B, X, Y, Z, R1 and R2 are as defined in the description, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are modulated by ACCβ inhibitors.

Suppression of the IgE-dependent allergic response by benzimidazole analogs

The present invention is directed to small molecule inhibitors of the IgE response to allergens which are useful in the treatment of allergy and/or asthma or any diseases where IgE is pathogenic.

Enhanced nickel(II) chelation by gew-dimethyl-substituted macrocyclic tetrathioethers

The conformational and Ni(II)-binding properties of 1,4,8,11-tetrathiocyclotetradecane (1) and derivatives bearing gem-dimethyl pairs at the 6- or at the 6- and 13-positions (2 and 3, respectively) are compared. The syntheses and crystal structures of 2, 3, and their Ni(ClO4)2 complexes are reported; analogous data for I and its Ni(BF4)2 complex have been in the literature for some time. All three Ni(II) complexes show very similar 14-membered ring conformations, but the metal-free macrocycles display different conformations, in the solid state. These structural data suggest that each gem-dimethyl pair progressively biases the macrocycle toward the chelating conformation. We have examined the relative Ni(II) affinities of 1-3 in CD3NO2 by means of competition experiments monitored by 1H NMR. Tetrathioether 2 binds Ni(II) approximately 7.3 times more tightly than does 1 at room temperature, and 3 binds Ni(II) approximately 49 times more tightly than does 1. Thus, each gem-dimethyl pair leads to a 1.1 kcal/mol improvement in Ni(II) binding free energy under these conditions. We suggest that the incremental improvement in binding strength across the series 1-3 is correlated to the incremental changes in macrocycle conformation observed in the crystal structures of the metal-free thioethers.

Acceleration of the 4-exo radical cyclization to a synthetically useful rate. Cyclization of the 2,2-dimethyl-5-cyano-4-pentenyl radical

The title radical, formed in the reaction of the corresponding bromide with Bu3SnH, cyclizes in a 4-exo fashion to give the (3,3-dimethylcyclobutyl)cyanomethyl radical. At 50°C, the rate constant for cyclization is 1.9 x 104s-1.