Tag: M.W=150-200

Jacobson, Roy published the artcileNaturally occurring spirocyclic ketals from lactones. III, Related Products of tetrahydropyran, the publication is Journal of Organic Chemistry (1982), 47(16), 3140-2, database is CAplus.

Treatment of (S)-propylene oxide with Li acetylide-ethylenediamine complex in NH₃(l) gave (S)-4-pentyn-2-ol which was converted to the tetrahydropyranyl ether; the lithium anion was generated followed by condensation with butyrolactone to give (7S)-I with optical purity of 80% identical to the ketals isolated from Andrena and Vespula species. Addnl. obtained was II identical to that isolated from Japanese hop oil. A simplified synthesis of chalcogran (III) from γ-caprolactone and the Li reagent prepared from Br(CH₂)₃OCH(OEt)Me was described.

Journal of Organic Chemistry published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Related Products of tetrahydropyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Robertson, Dale N. published the artcileAdducts of tert-alcohols containing an ethynyl group with dihydropyran. Potentially useful intermediates, Category: tetrahydropyran, the publication is Journal of Organic Chemistry (1960), 931-2, database is CAplus.

Acetylenic alcs. of the type RR’COHCCH (I) were found to add smoothly and in high yield to dihydropyran (II) to form tetrahydropyranyl (R²) compounds of the general structure RR’C(CCH)OR² (III). The R² grouping was stable to alkali but easily removed by aqueous acid or exchangeable with lower alcs. by acid catalysis. Organometallic intermediates were easily formed by reaction at the acetylenic H and compounds such as γ-hydroxy-α,β-acetylenic acids; esters and ketones thus were readily available. General procedure; the appropriate alc. (1 mole) and 1.2-2 moles II was swirled with a few crystals of p-MeC₆H₄SO₃H (the exothermic reaction began almost at once and was usually complete within 0.5-1.0 hr.); with higher mol. weight alcs. the mixture was heated on the steam bath 0.5-1.0 hr. to ensure completion. Anhydrous K₂CO₃ (1-2 g.) was added to the cooled mixture and the whole stirred 0.5 hr. or left overnight, the salts removed, excess II distilled at atm. pressure, and the product distilled in vacuo. Even Me₃COH added readily to II, although the product was not isolated. Since an equimolar mixture of the 2 reactants would contain the same C and H values as the products, the infrared spectrum of each product was determined The following III were obtained from I and II (R, R’, and b.p./mm. given): Me, Me, 64.5-5.5°/8; Et, Me, 62.5-4.5°/3.3; Me₂CHCH₂, Me, 47-50°/0.6-0.2; Me(CH₂)₅, Me, 76-7°/0.12; Ph, Me, 99-100.5°/0.02; (R,R’ = cyclohexyl), 101.5-2.5°/3.6-3.7.

Journal of Organic Chemistry published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Category: tetrahydropyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Kaiser, Roman published the artcileThe (5R*,9S*)- and (5R*,9R*)-2,2,9-trimethyl-1,6-dioxaspiro[4.4]non-3-ene and their dihydro derivatives as new constituents of geranium oil, Formula: C10H16O2, the publication is Helvetica Chimica Acta (1984), 67(5), 1198-203, database is CAplus.

(5R ,9S )- (I) [92356-08-6] and (5R ,9R )-2,2,9-trimethyl-1,6-dioxaspiro[4.4]non-3-ene (II) [92356-04-2] and their dihydro derivatives, III  [92356-09-7] and IV  [92356-10-0], were isolated from geranium oil and their structures determined by spectra and synthesis. Other trace monoterpenes such as nerol oxide  [1786-08-9] were also isolated.

Helvetica Chimica Acta published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Formula: C10H16O2.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Jouve, Pierre published the artcileNuclear magnetic resonance of the acetylenic proton in 1-alkynes, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Compt. Rend. (1963), 1497-9, database is CAplus.

The frequency of the N.M.R. signal of the acetylenic proton (CC-H) is determined for dilute CCl₄ solutions of 1-alkynes at 60 Mc. (A Varian A-60 instrument was used). An external reference, 5% Me₄Si in CCl₄, χ_r = 0.684 × 10^-6, is used Me₄Si is taken as zero. The value of the chem. shift when dilution no longer influences its position, σ_∞CCl4, is determined for 6 linear acetylenes, 1.73-1.87 (branching caused displacement toward weak fields, contrary to the inductive effect); for 4α- and ω-diynes, 1.78-1.84 (considerable interaction between bonds at ends of chain, but with longer chains similar to linear acetylenes); for 5 ene-ynes, 2.60-2.89 (strong displacement toward weak fields, resonance stabilization); for 3 acetylenes with conjugated benzene rings in the a position, 2.92-3.06 (same as ene-ynes, but more so); for 5 α-acetylenic alcs., 2.20-2.33 (characteristic for these compounds); for 3 acetals and propargyl ethers, 2.26-2.33 (like α-alcs., conjugation is not possible, only the electroneg. character of the O being affected the displacement); for 3 alcs. with benzene rings in the β position to the ethynyl group, 2.46-2.77 (homoallyl activation with orbital electrons of the triple bonds partially conjugated with those of the ring); and for 4 γ-oxygenated acetylenes, 1.89-1.93 (more like the corresponding hydrocarbons).

Compt. Rend. published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Claesson, Alf published the artcileAllenes and acetylenes. X. Convenient method for conversion of acetylenic derivatives into conjugated dienes via α-allenic alcohols, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1975), 29(5), 609-16, database is CAplus.

4-Alkoxy- and 4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ols are in most cases quantitatively converted into conjugated dienes when treated with LiAlH4 in refluxing THF or similar solvents. The reactions proceed via α- allenic alcohols. The dienes are free from positional isomers and the formation of alkenynes, which occurs in some cases, can be completely suppressed by a combination of LiAlH4 and AlCl3. Most of the conjugated dienes seem to be formed with low stereoselectivity. The E,E form is the predominant isomer of 2,4-hexadiene while of 4,6-decadiene the E,Z isomer predominates. These latter results may indicate that the attack by hydride on the central carbon atom of the propadienyl group is sterically hindered when the double bond remaining in the same position is formed with E configuration.

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Borujeni, Kaveh Parvanak published the artcileSilica-gel-supported aluminum chloride. A stable, efficient, selective, and reusable catalyst for tetrahydropyranylation of alcohols and phenols, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Synthetic Communications (2006), 36(18), 2705-2710, database is CAplus.

A simple, effective, and highly chemoselective method to form 2-tetrahydropyranyl ethers of alcs. and phenols in the presence of silica-gel-supported aluminum chloride as a heterogeneous Lewis acid catalyst is described. The catalyst can be easily recovered and reused without appreciable change in its efficiency.

Synthetic Communications published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Eguchi, Tadashi published the artcileSynthesis and biological activities of 22-hydroxy and 22-methoxy derivatives of 1α,25-dihydroxyvitamin D₃: importance of side chain conformation for biological activities, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Bioorganic Chemistry (1989), 17(3), 294-307, database is CAplus.

Title derivatives I (R = OH, OMe, R¹ = H; R = H, R¹ = OH, OMe) were prepared from 22-aldehyde II in order to clarify the precise structural requirement for exerting various biol. activities. While the synthetic vitamin D derivatives did not show any increase of serum calcium concentration in rats by oral administration, all derivatives induced into nitroblue tetrazolium (NBT)-pos. cells at a concentration more than 1 μg/mL in the NBT reduction test for induction of differentiation of HL-60 cells. The 22S-isomers I (R = H, R¹ = OH, OMe) were at least 30 times more effective than the corresponding 22R-isomers I (R = OH, OMe, R¹ = H). The binding affinity of I (R = H, R¹ = OMe) to the chick intestinal receptor for 1α,25-dihydroxyvitamin D₃ was about 3 times as potent as that of I (R = OMe, R¹ = H). A major structural difference was their side chain conformations, which were elucidated by mol. mechanics calculation (MM2 force field) and NMR studies. A zig-zag conformation turned out to be sterically most favorable for 22S-isomers, whereas such a zig-zag conformation is energetically unfavorable for 22R-isomers due to the interaction between the 22-substituent and the 16-methylene group. The side chain conformation seems to be responsible for the difference of their biol. activity and the zig-zag conformation plays an important role for the activities.

Bioorganic Chemistry published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Kong, Wangqing published the artcileExclusive 1,2-Aryl Shift in Platinum(II) Chloride-Catalyzed Cyclization of 1-(Indol-2-yl)-2,3-allenols, Category: tetrahydropyran, the publication is Advanced Synthesis & Catalysis (2012), 354(11-12), 2339-2347, S2339/1-S2339/79, database is CAplus.

An efficient cyclization of 1-(indole-2-yl)-2,3-allenols in the presence of platinum(II) chloride leading to polysubstituted carbazoles via 1,2-Me or an exclusive 1,2-aryl migration of the metal-carbene intermediate was observed The reaction proceeds via the intermediacy of a metal carbene intermediate, which induces the carbon-carbon bond cleavage via 1,2-migration to afford the products.

Advanced Synthesis & Catalysis published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Category: tetrahydropyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Grigg, Ronald published the artcilePalladium catalyzed triscyclization-anion capture queuing cascades, Synthetic Route of 27943-46-0, the publication is Tetrahedron Letters (1997), 38(10), 1825-1828, database is CAplus.

Palladium catalyzed regio- and, where appropriate, stereospecific triscyclization-anion capture processes are described involving vinyl- and allenyl-starter species, alkene/alkyne relay and terminating species and anion capture by allene/nucleophile (PhSO₂Na or s-amine) or (2-thienyl)tributylstannane. Thus, enetriyne HCCCH₂CH₂CCCH₂C(CO₂Et)₂CH₂CH:CICH₂CH₂CCH reacted with allene and nucleophiles (piperidine, NaO₂SPh) to give tricyclic compounds I (R = piperidino, O₂SPh).

Tetrahedron Letters published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Synthetic Route of 27943-46-0.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Doutheau, Alain published the artcileSynthesis of α-functionalized allenes, Recommanded Product: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Synthetic Communications (1982), 12(7), 557-63, database is CAplus.

Propargylic compounds HCCCR₂X (R = H, Me; X = tetrahydropyranyloxy, OH, NH₂) were converted to the resp. allenes Me₂C:C:CHCR₂X in two steps. Thus, HCCCH₂OH was treated with BuLi and Me₂C(NO₂)₂, and the Me₂C(NO₂)CCCH₂OH obtained was treated with LiAlH₄ in THF to give Me₂C:C:CHCH₂OH.

Synthetic Communications published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Recommanded Product: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics