67064-09-9

Usage

Molecular structure

2,5-Methanopentalene-3a(1H)-carbonyl chloride, hexahydro(9CI) has a complex molecular structure, which is a carbonyl chloride derivative of 2,5-methanopentalene, a hydrocarbon compound with a condensed ring system.

Usage

It is used in various chemical processes and reactions as a reagent.

Relevance

Its properties and potential applications are of interest to chemists, researchers, and industry professionals in the fields of organic chemistry and chemical synthesis.

Ongoing research

Further study and investigation into its chemical properties and potential uses are ongoing.

Upstream product

• 16200-53-6 3-noradamantanecarboxylic acid 

Downstream Products

• 3015-19-8 1-Hydroxy-2-aza-adamantan 
• 136199-02-5 rolofylline 
• 470485-25-7 6-benzoyloxy-2-[hexahydro-2,5-methanopentalen-3a(1H)-yl]-4H-1-benzopyran-4-one 
• 886440-14-8 hexahydro-2,5-methano-pentalene-3a-carboxylic acid [6-amino-1-(2-hydroxy-3-phenoxy-propyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-amide 

Relevant academic research and scientific papers

Generation and Reactions of 2-(1-Adamantyl)adamantene. Rearrangement to 3-(1-Adamantyl)-4-protoadamantylidene

The SN 1 methanolysis of (1-adamantyl)(3-noradamantyl)methyl heplafluorobutyrate at 100°C yielded (1-adamantyl)-(3-noradamantyl)methyl methyl ether (17), 2-(1-adamantyl)-1-methoxyadamantane (18), and 4-(1-adamantyl)-3-methoxyprotoadamantane (19) in a 2 : 65 : 33 ratio. The methanolysis of (1-adamantyl)(3-noradamantyl)diazomethane (7) at 0 °C also yielded 17, 18, and 19 in a 4 : 33 : 63 ratio. On the other hand, the photolysis of 7 in 99 : 1 (v/v) hexane-methanol gave 17,18, 2-(1-adamantyl)-2-methoxyadamantane (25), and 2-(1-adamantyl)-2,4-didehydroadamantane (20) in a 30 : 9 : 36 : 25 ratio. Presence of triethylamine decreased the yields of ethers 17, 18, and 25, and increased the yield of 20 to 46%. The formation of a considerable amount of 17 and the absence of 19 in the photolysis products indicate the generation of (1-adamantyl)(3-noradamantyl)methylidene (8). The formation of 25 and 20 suggests that the generated carbene 8 rearranges to 2-(1-adamantyl)adamantene (3b) and then gives 3-(1-adamantyl)-4-protoadamantylildene by the subsequent retro-insertion. An attempt to isolate 3b in the photolysis of 7 in cyclohexane failed, and the sole isolated product was 20.

Synthesis and biological evaluation of new berberine derivatives as cancer immunotherapy agents through targeting IDO1

To discover small-molecule cancer immunotherapy candidates through targeting Indoleamine 2,3-dioxygenase 1 (IDO1), twenty–five new berberine (BBR) derivatives defined with substituents on position 3 or 9 were synthesized and examined for repression of IFN-γ-induced IDO1 promoter activities. Structure–activity relationship (SAR) indicated that large volume groups at the 9-position might be beneficial for potency. Among them, compounds 2f, 2i, 2n, 2o and 8b exhibited increased activities, with inhibition rate of 71–90% compared with BBR. Their effects on IDO1 expression were further confirmed by protein level as well. Furthermore, compounds 2i and 2n exhibited anticancer activity by enhancing the specific lysis of NK cells to A549 through IDO1, but not cytotoxicity. Preliminary mechanism revealed that both of them inhibited IFN-γ-induced IDO1 expression through activating AMPK and subsequent inhibition of STAT1 phosphorylation. Therefore, compounds 2i and 2n have been selected as IDO1 modulators for small-molecule cancer immunotherapy for next investigation.

Palladium-catalyzed double activation and arylation of 2° and 3° C(sp3)-H bonds of the norbornane system: Formation of a C-C bond at the bridgehead carbon and bridgehead quaternary stereocenter

Pd-catalyzed activation and direct arylation of both 2° and the bridgehead 3° (sp3) C-H bonds and an unprecedented C-C bond formation at the bridgehead carbon of the norbornane system are reported. The assembly of bridgehead-substituted norbornane frameworks having contiguous stereocenters was accomplished. X-ray crystal structure analysis of representative molecules unambiguously established the stereochemistry.

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS

The present application relates to isothiazolylidene containing compounds of Formula (I) wherein R1, R2, R3, R4, and L are as defined in the specification, compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions.

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS

The present invention relates to thiophene containing compounds of formula (I) wherein m, n, p, q, r, s, R1, R2, and R3 are as defined in the description. Included also are pharmaceutical compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and pharmaceutical compositions.

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS

The present application relates to isothiazolylidene containing compounds of Formula (I) wherein R1, R2, R3, R4, and L are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF

The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and L2, are defined in th

Photolytic Generation of Anti-Bredt Imines from 1-Azidobicyclooctane, 1-Azidobicyclononane, and 3-Azidonoradamantane

Photolysis of 1-azidobicyclooctane (18), 1-acidobicyclononane (24), and 3-azidonoradamantane (37) generated the corresponding bridgehead imines 12a, 13, 14, 15, and 16, respectively.These bridgehead imines were trapped spontaneously with sol

Organic Peroxides, XIV. The Thermal Decomposition of Polycyclic tert-Butyl Bridgehead Peroxycarboxylates

Eleven bridgehead peresters (1, 2, 5 - 8, 10, 12, 14, 18, 21) have been prepared for the first time and the products and the kinetics of their thermal decomposition were investigated.The correlations of all known thermolysis constants of bridgehead peresters with the steric substituent constants φf, with the solvolysis constants of the corresponding bridgehead bromides, as well as with the change in strain enthalpy ΔHsp for hydride abstraction from the bridgehead, as calculated by the procedure of v.R.Schleyer, were analysed.The thermolysis constants of these peresters are mainly determined by the polar effect in the transition state of the perester fragmentation.