22555-67-5

Basic information

• Product Name: cis-9-Phenyl-2,6-dimethyl-nonadien-(2,6)
• Synonyms: cis-9-Phenyl-2,6-dimethyl-nonadien-(2,6)
• CAS NO: 22555-67-5
• Molecular Weight: 228.378
• Mol File: 22555-67-5.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: cis-9-Phenyl-2,6-dimethyl-nonadien-(2,6)(CAS DataBase Reference)
• NIST Chemistry Reference: cis-9-Phenyl-2,6-dimethyl-nonadien-(2,6)(22555-67-5)
• EPA Substance Registry System: cis-9-Phenyl-2,6-dimethyl-nonadien-(2,6)(22555-67-5)

Safety Data

• Hazardous Substances Data: 22555-67-5(Hazardous Substances Data)

Upstream product

• 110-93-0 6-Methyl-hept-5-en-2-on 
• 7484-37-9 (3-phenylpropyl)triphenylphosphonium bromide 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 6921-34-2 benzylmagnesium chloride 
• 1589-82-8 phenylmagnesium bromide 
• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 74408-52-9 geraniol acetate 
• 106-24-1 Geraniol 
• 1309466-61-2 C₁₆H₃₁O₃PS 
• 100-44-7 benzyl chloride 
• 637-59-2 1-Bromo-3-phenylpropane 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 6138-90-5 trans-geranyl bromide 
• 20536-36-1 neryl chloride 

Downstream Products

• 471-79-4 (+/-)-10-epi-podocarpa-8,11,13-triene 
• 1182121-24-9 (E)-(8-azido-7-bromo-4,8-dimethylnon-3-enyl)benzene 
• 10064-16-1 podocarpa-8,11,13-triene 

Relevant articles and documents

Design, synthesis and anthelmintic activity of 7-keto-sempervirol analogues

The plant-derived, diterpenoid 7-keto-sempervirol was recently reported to display moderate activity against larval stages of Schistosoma mansoni (IC50 = 19.1 μM) and Fasciola hepatica (IC50 = 17.7 μM), two related parasitic blood and liver flukes responsible for the neglected tropical diseases schistosomiasis and fascioliasis, respectively. Here, we aimed to increase the potency of 7-keto-sempervirol by total synthesis of 30 structural analogues. Subsequent screening of these new diterpenoids against juvenile and adult lifecycle stages of both parasites as well as the human HepG2 liver cell line and the bovine MDBK kidney cell line revealed structure-activity relationship trends. The most active analogue, 7d, displayed improved dual anthelmintic activity over 7-keto-sempervirol (IC50 ≈ 6 μM for larval blood flukes; IC50 ≈ 3 μM for juvenile liver flukes) and moderate selectivity (SI ≈ 4–5 for blood flukes, 8–13 for liver flukes compared to HepG2 and MDBK cells, respectively). Phenotypic studies using scanning electron microscopy revealed substantial tegumental alterations in both helminth species, supporting the hypothesis that the parasite surface is one of the main targets of this family of molecules. Further modifications of 7d could lead to greater potency and selectivity metrics resulting in a new class of broad-spectrum anthelmintic.

Synthetic Study of Phainanoids. Highly Diastereoselective Construction of the 4,5-Spirocycle via Palladium-Catalyzed Intramolecular Alkenylation

An efficient strategy to synthesize the western part of phainanoids is reported. The benzofuranone-based 4,5-spirocyclic motif is constructed diastereoselectively via a palladium-catalyzed intramolecular alkenylation. The computational study suggests that

Highly enantioselective proton-initiated polycyclization of polyenes

This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantioselective proton-initiated polycyclization promoted by the 1:1 complex of o,o′-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.