4773-13-1Relevant articles and documents
NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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Paragraph 468, (2016/09/15)
Described herein are neuroactive steroids of the Formula (I): (I) or a pharmaceutically acceptable salt thereof; wherein R1, R2, Ra, G, X, Y, Z, and n are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. Also provided are pharmaceutical compositions comprising a compound described herein and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.
Preparation of cyclic sulfites by transesterification of diols and diisopropyl sulfite
King, Steven A.,Pipik, Brenda,Conlon, David A.,Bhupathy
, p. 701 - 707 (2007/10/03)
Cyclic sulfites of 1,2-, 1,3- and 1,4-diols can be prepared in high yield by acid or base catalyzed transesterification with diisopropyl sulfite.
Reaction of α-Peroxy Lactones with C, N, P, and S Nucleophiles: Adduct Formation and Nucleophile Oxidation by Nucleophilic Attack at and Biphilic Insertion into the Peroxide Bond
Adam, Waldemar,Biancafort, Lluis
, p. 1623 - 1629 (2007/10/03)
The reactions of the α-peroxy lactones 1 with a variety of carbon, nitrogen, phosphorus, and sulfur nucleophiles yield, on SN2 attack at the more electrophilic alkoxy oxygen of the peroxide bond, diverse addition and oxygen transfer products, together with the catalytic Grob-type fragmentation. The nature of the nucleophile determines the fate of the open-chain intermediate I. Thus, protic nucleophiles such as primary and secondary amines and thiols lead to the second intermediate I′ through proton shift subsequent to the SN2 step, while nonprotic amines and sulfides, as well as diazoalkanes, lead to oxidation products or to the cycloadducts 10-15. Trivalent phosphorus nucleophiles such as phosphines and phosphites and diisopropyl sulfoxylate prefer biphilic insertion, as documented by the fact that the nucleophilicity rather than the steric demand of these reagents controls their reactivity. The labile adducts undergo a variety of transformations to the final stable products. For protic nucleophiles, the amine adducts 5 and 6 are sufficiently persistent for isolation, whereas the sulfenic esters formed by thiol addition are further oxidized to the sulfinic esters 7 and 8 or react with excess thiol to the corresponding disulfides. For aprotic nucleophiles, the dipolar intermediates I decompose into acetone and CO2 with regeneration of the nucleophile (Grob-type fragmentation), as seen for DABCO and pyridine N-oxide, or they extrude the α-lactone to afford the oxygen transfer product. The corresponding ketones, pyridine N-oxide, sulfoxides, and sulfones are obtained by this route from diazoalkanes, pyridine, sulfides and sulfoxides. Additionally, the diazoalkane intermediates I also cyclize to the cycloadducts 10-12. The thermally labile phosphorus adducts 13-15, which were observed by low-temperature NMR spectroscopy, decompose to the α-lactone and the phosphorus oxides. Analogously, diisopropyl sulfite is obtained from the sulfoxylate adduct. As for the fate of the α-lactones (the reduction products of the α-peroxy lactones), the dimethyl derivative either oligomerizes to the oligoester 2a or is trapped by methanol as the α-methoxy acid 4a, while the spiroadamantyl α-lactone decarbonylates to adamantanone.
