Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 707-61-9, is researched, SMILESS is CC1=CP(CC1)(C2=CC=CC=C2)=O, Molecular C11H13OPJournal, Article, Chemistry – A European Journal called Part I: The Development of the Catalytic Wittig Reaction, Author is O’Brien, Christopher J.; Nixon, Zachary S.; Holohan, Andrew J.; Kunkel, Stephen R.; Tellez, Jennifer L.; Doonan, Bryan J.; Coyle, Emma E.; Lavigne, Florie; Kang, Lauren J.; Przeworski, Katherine C., the main research direction is Wittig reaction phosphole phospholane phosphate oxide preparation catalyst; Wittig reaction; alkenes; homogeneous catalysis; olefination; organocatalysis.Computed Properties of C11H13OP.
The authors have developed the first catalytic (in phosphane) Wittig reaction (CWR). The utilization of an organosilane was pivotal for success as it allowed for the chemoselective reduction of a phosphane oxide. Protocol optimization evaluated the phosphane oxide pre-catalyst structure, loading, organosilane, temperature, solvent, and base. These studies demonstrated that to maintain viable catalytic performance it was necessary to employ cyclic phosphane oxide pre-catalysts of type 1. Initial substrate studies utilized sodium carbonate as a base, and further experimentation identified N,N-diisopropylethylamine (DIPEA) as a soluble alternative. The use of DIPEA improved the ease of use, broadened the substrate scope and decreased the pre-catalyst loading. The optimized protocols were compatible with alkyl, aryl, and heterocyclic (furyl, indolyl, pyridyl, pyrrolyl, and thienyl) aldehydes to produce both disubstituted and trisubstituted olefins in moderate-to-high yields (60-96%) by using a pre-catalyst loading of 4-10 mol%. Kinetic E/Z selectivity was generally 66:34. Complete (E)-selectivity for disubstituted α,β-unsaturated products was achieved through a phosphane-mediated isomerization event. The CWR was applied to the synthesis of a known precursor to the anti-Alzheimer drug donepezil hydrochloride, on a multi-gram scale (12.2 g, 74% yield). In addition, the described CWR is the only transition-metal-free/heavy-metal-free catalytic olefination process, excluding proton-catalyzed elimination reactions. The synthesis of the target compounds was achieved (1R,3S)-rel-3-methyl-1-phenylphospholane 1-oxide, (1R,3R)-rel-3-methyl-1-phenylphospholane 1-oxide, 1-phenylphospholane 1-oxide as catalyst precursors. 2-Phenyl-1,3,2-dioxaphospholane 2-oxide, diethylphenylphosphine oxide, 5-phenyl-5H-benzo[b]phosphindole 5-oxide, (2R,2’R,5R,5’R)-1,1′-(1,2-ethanediyl)bis[2,5-bis(1-methylethyl)phospholane], 2-[2-[(2R,5R)-2,5-dimethyl-1-phospholanyl]phenyl]-1,3-dioxolane were also evaluated.
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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem