Arborescin

Base Information

• Chemical Name: Arborescin
• CAS No.: 6831-14-7
• Molecular Formula: C15H20O3
• Molecular Weight: 248.3175
• UNII: N534V4NHPR
• DSSTox Substance ID: DTXSID60218462
• Nikkaji Number: J15.057F
• Wikidata: Q27140382
• Mol file: 6831-14-7.mol

Synonyms:arborescin

Chemical Property of Arborescin

Chemical Property:

• Vapor Pressure: 2.33E-06mmHg at 25°C
• Melting Point: 140-142°
• Boiling Point: 392.2°Cat760mmHg
• Flash Point: 165.4°C
• PSA: 38.83000
• Density: 1.2g/cm³
• LogP: 2.45180
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 468

Purity/Quality:

99%, ^*data from raw suppliers

ARBORESCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC3(C4(O3)CC=C(C4C2OC1=O)C)C
• Isomeric SMILES: C[C@H]1[C@@H]2CC[C@]3([C@@]4(O3)CC=C([C@@H]4[C@H]2OC1=O)C)C

Technology Process of Arborescin

There total 7 articles about Arborescin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1β,10β-Epoxyguaia-3,11(13)-dien-12,6α-olide (137624-14-7,84692-91-1) → arborescin (6831-14-7)

Guidance literature:

With quinoline; hydrogen; at 25 ℃; for 2h; under 1034.32 Torr; regioselective reaction;

DOI:10.1002/ardp.201100065

Reference yield: 49.0%

(11S)-1β,10β-epoxy-3α-(mesyloxy)-4βH-guaiano-13,6α-lactone (82691-64-3) → Arborescin (6831-14-7)

Guidance literature:

With lithium carbonate; lithium bromide; In N,N-dimethyl-formamide; at 118 - 129 ℃; for 2h;

DOI:10.1021/jo00141a020

Reference yield: 22.0%

(11S)-1β-(mesyloxy)eudesm-3-eno-12,6α-lactone (149792-40-5) → arborescin (6831-14-7) + (11S)-1α,10α-epoxyguai-3-eno-12,6α-lactone (25319-03-3) + (+)-3α,4α-epoxy-5,7αH,6,11βH-guai-(1,10)-en-6,12-olide (124097-47-8) + (11S)-3β,4β-epoxyguai-1(10)-eno-12,6α-lactone (124027-52-7)

Guidance literature:

With potassium acetate; acetic acid; 3-chloro-benzenecarboperoxoic acid; Yield given. Multistep reaction. Further byproducts given; 1) reflux, 25 h, 2) chloroform, -20 deg C, 18 h;

DOI:10.1021/jo00067a056

upstream raw materials:

(11S)-1β,10β-epoxy-3α-(mesyloxy)-4βH-guaiano-13,6α-lactone

(11S)-1β,10β-epoxy-3α-hydroxy-4βH-guaiano-13,6α-lactone

(11S)-3α-(benzoyloxy)-1β,10β-epoxy-4βH-guaiano-13,6α-lactone

(11S)-1β-(mesyloxy)eudesm-3-eno-12,6α-lactone

Refernces

• 1、 Ando, Masayoshi,Yoshimura, Hideki. "Syntheses of Four Possible Diastereoisomers of Bohlmann's Structure of Isoepoxyestafiatin. The Stereochemical Assignment of Isoepoxyestafiatin". . p. 4127 - 4131. Retrieved 2007/10/02.