74591-03-0

Basic information

• Product Name: [(1S,1aS,2aS,5R,5aR,7aR,7bS,7cS)-5-phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-yl]acetic acid
• Synonyms: 74591-03-0; Endiandric Acid A
• CAS NO: 74591-03-0
• Molecular Formula: C₂₁H₂₂O₂
• Molecular Weight: 306.3982
• Mol File: 74591-03-0.mol

Chemical Properties

• Melting Point: 147-149°
• Boiling Point: 476.806°C at 760 mmHg
• Flash Point: 373.364°C
• Density: 1.194g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.607
• PKA: 5.1, 5.0(at 25℃)
• CAS DataBase Reference: [(1S,1aS,2aS,5R,5aR,7aR,7bS,7cS)-5-phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-yl]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(1S,1aS,2aS,5R,5aR,7aR,7bS,7cS)-5-phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-yl]acetic acid(74591-03-0)
• EPA Substance Registry System: [(1S,1aS,2aS,5R,5aR,7aR,7bS,7cS)-5-phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-yl]acetic acid(74591-03-0)

Safety Data

• Hazardous Substances Data: 74591-03-0(Hazardous Substances Data)

Upstream product

• 127390-81-2 5-(tert-butyldimethylsilanyloxy)pent-2-ynal 
• 82679-77-4 tert-Butyl-diphenyl-((1S,1aR,2aS,5R,5aR,7aS,7bS,7cS)-5-phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-ylmethoxy)-silane 
• 82679-78-5 ((1S,1aR,2aS,5R,5aR,7aS,7bS,7cS)-5-Phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-yl)-methanol 
• 82679-79-6 (1S,1aR,2aS,5R,5aR,7aS,7bS,7cS)-1-Bromomethyl-5-phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylene 
• 20390-71-0 2-hydroxy-3-cyclohexen-1-acetic acid lactone 

Downstream Products

• 74635-24-8 methyl 2-(6'-phenyltetracyclo<5,4,2,0^3,13,0^10,12>trideca-4',8'-dien-11'-yl)acetate 

Relevant articles and documents

Total synthesis of endiandric acid A via an intramolecular Diels-Alder strategy

The total synthesis of endiandric acid A (1), featuring an intramolecular Diels-Alder approach for elaboration of the 6-5-6 carbocyclic array and an intramolecular Majetich reaction for construction of the four-membered ring, is described.

Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F

A measure of the strength of a synthetic strategy is its versatility: specifically, whether it allows structurally distinct targets to be prepared. Herein we disclose a unified approach for the total synthesis of natural products of three distinct structural types, all of which occur naturally as racemic mixtures. The point of divergence involves the terminal alkylation of a conjugated tetrayne, and culminates in a significantly shortened synthesis of endiandric acid A (8 steps), the first total synthesis of kingianic acid E (8 steps), and a second-generation synthesis of kingianins A, D, and F (11 steps). Evidence for redox catalysis in the biosynthesis of kingianic acid E is presented.

Constituents of Some Species of Beilschmiedia and Endiandra (Lauraceae): New Endiandric acid and Benzopyran Derivatives Isolated from B. oligandra

On the basis of a preliminary u.v. assay of the dried leaf of nine species of Beilschmiedia and 26 species of Endiandra, several were selected for closer examination.Magnolol (9) was found in B. volckii and (+)-sesamin (10) was isolated from E. xanthocarpa.Endiandric acid B (2) and endiandric acid C (3) were obtained from both E. jonesii and B. tooram, and endiandric acid A (1) was found in B. obtusifolia.The new endiandric acid derivative (1'RS,3'RS,6'SR,7'SR,10'SR,11'RS,12'RS,13'RS)-2-3,13.010,12>trideca-4',8'-dien-11'-yl>acetic acid (3'',4''-methylenedioxyendiandric acid A) (4) was extracted from B. oligandra which also yielded the new phenolic benzopyran derivative (-)-(E)-2-(4',8'-dimethylnona-3',7'-dienyl)-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-6-ol (oligandrol) (12a).Several known hydrocarbon derivatives and terpenoids were isolated from from the leaf of E. palmerstonii and E. bailonii, both of which were devoid of endiandric acids.