39085-59-1 Usage
Description
2,4,6-Triisopropylbenzenesulfonyl hydrazide (TPSH) is a white crystalline compound that serves as a versatile reagent in various chemical reactions. It is primarily known for its ability to generate diimide, which is a highly reactive intermediate used in the reduction of alkenes and other double bonds. TPSH is also capable of undergoing condensation reactions with ketones and aldehydes, leading to the formation of hydrazones that can be further converted into reactive intermediates such as diazoalkanes, carbenes, carbenium ions, and alkyllithiums.
Uses
Used in Chemical Synthesis:
2,4,6-Triisopropylbenzenesulfonyl hydrazide is used as a reagent for the generation of diimide, which is essential in the reduction of alkenes and other double bonds. This selective reduction method is particularly useful in the synthesis of polymers and natural products, as it tolerates sensitive functional groups such as esters, ketones, or organometal complexes.
Used in Pharmaceutical Industry:
TPSH is used as a reagent to synthesize nitrogen-containing polycyclic compounds through intramolecular cyclopropanation of N-alkyl indoles or pyrroles. These compounds have potential applications in the development of new pharmaceuticals and drug candidates.
Used in Material Science:
In the field of material science, TPSH is utilized as a reagent to synthesize vinyl sulfones by sulfonylation reaction of vinyl bromides. These vinyl sulfones are important building blocks for the development of various polymers and materials with specific properties.
Used in Organic Chemistry:
2,4,6-Triisopropylbenzenesulfonyl hydrazide is used as a reagent to synthesize nitrile derivatives from carbonyl compounds via the formation of corresponding hydrazones. This method is valuable in organic chemistry for the synthesis of various organic compounds and intermediates.
Check Digit Verification of cas no
The CAS Registry Mumber 39085-59-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,9,0,8 and 5 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 39085-59:
(7*3)+(6*9)+(5*0)+(4*8)+(3*5)+(2*5)+(1*9)=141
141 % 10 = 1
So 39085-59-1 is a valid CAS Registry Number.
InChI:InChI=1/C15H26N2O2S/c1-9(2)12-7-13(10(3)4)15(20(18,19)17-16)14(8-12)11(5)6/h7-11,17H,16H2,1-6H3
39085-59-1Relevant articles and documents
Multiple on-resin olefin metathesis to form ring-expanded analogues of the lantibiotic peptide, Lacticin 3147 A2
Pattabiraman, Vijaya R.,Stymiest, Jake L.,Derksen, Darren J.,Martin, Nathaniel I.,Vederas, John C.
, p. 699 - 702 (2007)
Chemical synthesis of lantibiotic analogues wherein monosulfide bridges are replaced with other groups can shed light on structure-activity relationships and generate variants that are resistant to aerobic oxidation and have better metabolic stability. This work describes the first complete synthesis of a carbocyclic lantibiotic analogue 2, using sequential on-resin ring-closing olefin metathesis and solution-phase peptide synthesis. The methodology described should find wide application for the preparation of rigidified peptidomimetics containing multiple carbocyclic rings.
Total Syntheses of (-)-Englerins A/B, (+)-Orientalols E/F, and (-)-Oxyphyllol
Liu, Pengcai,Cui, Yutao,Chen, Kang,Zhou, Xinyue,Pan, Wenyan,Ren, Jun,Wang, Zhongwen
supporting information, p. 2517 - 2521 (2018/05/17)
(-)-Englerin A was synthesized in 20 steps from the commercially available material (R)-(+)-limonene. In addition, (-)-englerin B, (+)-orientalol E/F and (-)-oxyphyllol were obtained from the intermediate in the route. The key steps include a hydroxyl-directing stereoselective and regioselective intramolecular cyclopropanation and a multi-gram-scale stereoselective formal intramolecular [3 + 2] cross cycloaddition ([3 + 2]-IMCC) of a cyclopropane 1,1-diester with a carbonyl. A precursor of 7,10-diastereoisomer of englerins was also obtained.
Base-mediated tandem sulfonylation and oximation of alkenes in water
Wang, Bin,Tang, Lin,Liu, Liyan,Li, Yanan,Yang, Yu,Wang, Zhiyong
supporting information, p. 5794 - 5799 (2017/12/26)
A base-mediated bifunctionalization of alkenes for the synthesis of α-sulfonylethanone oximes was developed in water under metal-free conditions. This reaction features a wide substrate scope and facile starting materials to afford the desired products in high yields.
