trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-dimethanol

Base Information

• Chemical Name: trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-dimethanol
• CAS No.: 26495-88-5
• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.34
• NSC Number: 135356
• DSSTox Substance ID: DTXSID20949366
• Nikkaji Number: J1.470.014E
• ChEMBL ID: CHEMBL1377175
• Mol file: 26495-88-5.mol

Synonyms:26495-88-5;trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-dimethanol;(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)dimethanol;tetracyclo[6.6.2.0~2,7~.0~9,14~]hexadeca-2,4,6,9,11,13-hexaene-15,16-diyldimethanol;5445-55-6;Maybridge3_001027;Oprea1_148579;CBDivE_000123;MLS000851196;SCHEMBL561629;CHEMBL1377175;DTXSID20949366;JRUAWKGGVJZZQC-UHFFFAOYSA-N;JRUAWKGGVJZZQC-VNGAXPGBSA-N;HMS1433O15;HMS2807D21;NSC135356;CCG-242635;NSC-135356;IDI1_012414;SMR000457439;SR-01000194976;SR-01000194976-1;[16-(hydroxymethyl)tetracyclo[6.6.2.0~2,7~.0~9,14~]hexadeca-2,4,6,9,11,13-hexaen-15-yl]methanol

Chemical Property of trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-dimethanol

Chemical Property:

• Vapor Pressure: 4.97E-09mmHg at 25°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 266.130679813
• Heavy Atom Count: 20
• Complexity: 297

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C3C(C(C(C2=C1)C4=CC=CC=C34)CO)CO

Technology Process of trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-dimethanol

There total 35 articles about trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-dimethanol 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: 98.0%

trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid dimethyl ester (23194-04-9,33216-01-2,33741-21-8,33741-22-9,36326-56-4,41204-41-5) → 9,10-dihydro-9,10-ethanoanthracene-11,12-dimethyl alcohol (5445-55-6,26495-88-5,33216-02-3,41063-84-7,41204-44-8,71991-70-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2013.08.046

Reference yield: 92.0%

(11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid (23194-05-0,27069-21-2,33216-00-1,36326-57-5,70738-17-9,36326-58-6) → (R,R)-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene (5445-55-6,26495-88-5,33216-02-3,41063-84-7,41204-44-8,71991-70-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

Reference yield: 89.0%

(11S,12S)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid (33216-00-1) → (S,S)-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene (5445-55-6,26495-88-5,33216-02-3,41063-84-7,41204-44-8,71991-70-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

upstream raw materials:

racemic-9,10-dihydro-9,10-ethanoanthacene trans-dicarboxylic acid

dimethyl 2,3:5,6-dibenzobicyclo<2.2.2>octa-2,5-diene-trans-7,8-dicarboxylate

trans-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid (11,12)-diethyl ester

anthracene

Downstream raw materials:

C₃₂H₃₀O₆S₂

(+/-)-trans-11,12-bis-(toluene-4-sulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracene

(S,S)-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene

Refernces

Copper(I)-catalyzed intramolecular C_aryl-O bond-forming cyclization for the synthesis of 1,4-benzodioxines and its application in the total synthesis of sweetening isovanillins

10.1055/s-0030-1258206

The study presents a copper(I)-catalyzed intramolecular C-O bond-forming cyclization approach for the synthesis of various substituted 1,4-benzodioxines, utilizing a BINOL-CuI complex as a catalyst. This method was effectively applied to the total synthesis of isovanillyl sweetening agents, specifically 5-(2,3-dihydro-1,4-benzodioxin-2-yl)-2-methoxyphenol and 5-(2,3-dihydro-1,4-benzoxathiin-2-yl)-2-methoxyphenol, which are known to be significantly sweeter than sucrose. The process involves a five-step synthesis from isovanillin, yielding the sweetening agents in 15.8% and 14.85% overall yields, respectively. The research also explores the scope and limitations of the method, discussing the impact of different ligands, copper salts, solvents, and bases on the reaction efficiency. The study further proposes a possible mechanism for the Ullmann-type intramolecular C-O coupling cyclization reaction and provides detailed experimental procedures, characterization data, and spectral information for the synthesized compounds.