19908-69-1

Basic information

• Product Name: Confertin
• Synonyms: Confertin;(3aR,7aα,9aα)-Dodecahydro-4aβ,8β-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione;Anhydrocumanin;3-Methylene-4aβ,8β-dimethyl-3aα,4,4aα,5,6,7,7aα,8,9,9aβ-decahydroazuleno[6,5-b]furan-2,5(3H)-dione;8-epi-Confertin
• CAS NO: 19908-69-1
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.3175
• Mol File: 19908-69-1.mol

Chemical Properties

• Boiling Point: 407.3°Cat760mmHg
• Flash Point: 181.4°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 7.61E-07mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: Confertin(CAS DataBase Reference)
• NIST Chemistry Reference: Confertin(19908-69-1)
• EPA Substance Registry System: Confertin(19908-69-1)

Safety Data

• Hazardous Substances Data: 19908-69-1(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Confertin is used as a pharmaceutical compound for its potential therapeutic properties. Its unique chemical structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs.
2. Used in Research and Development:
Confertin is utilized as a research compound for studying its chemical properties, interactions with biopolymers and macromolecules, and potential applications in various fields, including medicine and biotechnology.
3. Used in Natural Product Chemistry:
As a naturally occurring compound, Confertin is used in the study of the chemical constituents of Inula hupehensis and other related plants. This can lead to a better understanding of the plant's pharmacological properties and potential uses in traditional medicine.

InChI:InChI=1/C15H20O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h8,10-12H,2,4-7H2,1,3H3/t8-,10+,11-,12+,15-/m0/s1

Upstream product

• 114579-31-6 <3aR,4aS,5S,7aS,8S,9aR>-5-Hydroxy-4a,8-dimethyl-3-methylen-decahydroazuleno<6,5-b>furan-2(3H)-on 
• 50-00-0 formaldehyd 
• 105-36-2 ethyl bromoacetate 
• 105787-90-4 (1S,3aS,4S,8aS)-1-(t-Butyldimethylsiloxy)-4,8a-dimethyloctahydro-6(1H)-azulenon 
• 60403-28-3 dec-t-5-yl> acetic acid-γ-lactone 
• 68197-11-5 c-2,t-7-dimethyl-t-8-(t-butyloxy)-r-1H-bicyclo<5.3.0>decan-5-one 
• 74615-15-9 ((3S,3aS,8R,8aS)-3-tert-Butoxy-3a,8-dimethyl-1,2,3,3a,4,7,8,8a-octahydro-azulen-5-yl)-acetic acid methyl ester 
• 74615-16-0 (1R,3aR,4S,6R,7S,8aR)-1-tert-Butoxy-7-(2-hydroxy-ethyl)-4,8a-dimethyl-decahydro-azulen-6-ol 
• 146644-15-7 (+/-)-4-methyl-1,2,3,4,5,8-hexahydro-1-oxoazulene-7-ethanol 
• 146644-12-4 (+/-)-4-methyl-7-methylene-3,4,5,6,7,8-hexahydroazulen-1(2H)-one 
• 123130-59-6 3-(1-methylethenyl)-2-<2-<(trimethylsilyl)methyl>allyl>-2-cyclopenten-1-one 
• 60403-31-8 (3aS,4aR,5R,7aR,8S,9aR)-5-tert-Butoxy-4a,8-dimethyl-3-methylene-decahydro-azuleno[6,5-b]furan-2-one 
• 142927-70-6 (1S,3aS,4S,8aS)-1-Hydroxy-4,8a-dimethyl-octahydro-azulen-6-one 
• 72341-88-9 (3aR,4aS,5S,7aS,8S,9aR)-5-Hydroxy-4a,8-dimethyl-2-oxo-dodecahydro-azuleno[6,5-b]furan-3-carboxylic acid 

Downstream Products

• 5945-42-6 (+/-)-aromaticin 

Relevant articles and documents

Enantioselective Conjugate Addition Greatly Improves the Synthesis of (+)-Confertin

The five-membered ring building blocks 2+3 are enantioselectively produced by conjugate addition of a chiral ligand-modified organocuprate to 2-methylcyclopent-2-enone (1) (chemical yield: 88percent; e.e.: 88percent) and successfully converted in a multi-step sequence, after final enantioselection by recrystallization of an appropriate intermediate, into the pseudoguaianolide (+)-confertin (5).- Key Words: enantioselective conjugate addition; chiral ligand-modified organocuprates; total synthesis of (+)-confertin

Allylsilane-Based Annulations. Direct Stereoselective Syntheses of (+/-)-Graveolide and (+/-)-Aromaticin

An allylsilane-based annulation was used to construct a functionalized perhydroazulene.The C(1), C(5), and C(10) stereocenters, characteristic of the helenanolides, were established using a reductive alkylation strategy.Stereoselective syntheses of the pseudoguaianolides graveolide and aromaticin were achieved.

Total Synthesis of the Pseudoguaianolide (+)-Confertin

The first total synthesis of the pseudoguaianolide (+)-confertin (1) begins with the preparation of the enantiomerically pure cyclopropane derivative 6b and its stereospecific ring expansion furnishing the five-membered ring A-building block 8a.The AB ketone 21d is produced by intermolecular Michael addition, Lewis acid catalyzed intramolecular hetero-ene reaction, and a pair of oxidation/reduction reactions.Fusion of the heterocyclic five-membered ring and α-methylenation of the ABC intermediate 35c is accomplished by well-known technology.The structure of essential synthetic intermediates has been determined by 2D-NMR, CD spectroscopy, or single crystal X-ray analysis.The whole synthesis starts from α-chloroacetone and reaches the target compound 1 after 22 steps.