2,5-Cyclohexadien-1-one, 4-hydroxy-4-(phenylethynyl)-

Base Information

• Chemical Name: 2,5-Cyclohexadien-1-one, 4-hydroxy-4-(phenylethynyl)-
• CAS No.: 120552-88-7
• Molecular Formula: C14H10O2
• Molecular Weight: 210.232
• DSSTox Substance ID: DTXSID10451726
• Nikkaji Number: J463.399G
• Mol file: 120552-88-7.mol

Synonyms:4-Hydroxy-4-(phenylethynyl)-2,5-cyclohexadien-1-one;2,5-Cyclohexadien-1-one, 4-hydroxy-4-(phenylethynyl)-;120552-88-7;SCHEMBL9214104;DTXSID10451726;YKVBOJPUYBYFAC-UHFFFAOYSA-N;4-hydroxy-4 -(phenylethynyl)-2,5-cyclohexadiene-1-one;4-Hydroxy-4-(phenylethynyl)-2,5-cyclohexadiene-1-one

Chemical Property of 2,5-Cyclohexadien-1-one, 4-hydroxy-4-(phenylethynyl)-

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 210.068079557
• Heavy Atom Count: 16
• Complexity: 381

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC2(C=CC(=O)C=C2)O

Technology Process of 2,5-Cyclohexadien-1-one, 4-hydroxy-4-(phenylethynyl)-

There total 2 articles about 2,5-Cyclohexadien-1-one, 4-hydroxy-4-(phenylethynyl)- 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: 87.0%

phenylacetylene (536-74-3) + p-benzoquinone (106-51-4) → 4-hydroxy-4-(phenylethynyl)cyclohexa-2,5-dien-1-one (120552-88-7)

Guidance literature:

phenylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

p-benzoquinone; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03160

Reference yield:

p-benzoquinone (106-51-4) + lithium phenylacetylide (4440-01-1) → 4-hydroxy-4-(phenylethynyl)cyclohexa-2,5-dien-1-one (120552-88-7)

Guidance literature:

DOI:10.1021/ja00219a079

Reference yield: 91.0%

4-hydroxy-4-(phenylethynyl)cyclohexa-2,5-dien-1-one (120552-88-7) → 4-benzoyl-5-hydroxycyclohepta-2,4,6-trien-1-one

Guidance literature:

With 8-methylquinoline 1-oxide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); In 1,2-dichloro-ethane; at 20 ℃; for 2h; Reagent/catalyst; Solvent; Time; regioselective reaction; Inert atmosphere; Large scale;

DOI:10.1021/acs.orglett.5b03160

upstream raw materials:

p-benzoquinone

lithium phenylacetylide

phenylacetylene

Downstream raw materials:

(4S,5S)-5-(3-Dimethylamino-propyl)-4-hydroxy-4-phenylethynyl-cyclohex-2-enone

5-hydroxy-2-phenylbenzofuran

1-(4-hydroxyphenyl)-2-phenylethan-1,2-dione

4-(2-phenylethynyl)phenol

Refernces

• 1、 Schie?l, Jasmin,Stein, Philipp M.,Stirn, Judith,Emler, Kirsten,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.. "Strategic Approach on N-Oxides in Gold Catalysis – A Case Study". supporting information. p. 725 - 738. Retrieved 2018/10/20.
• 2、 Kim, Ikyon,Kim, Kyungsun,Choi, Jungeun. "A direct approach to 5-hydroxybenzofurans via a platinum-catalyzed domino rearrangement/5-endo-dig cyclization reaction of quinols". supporting information; experimental part. p. 8492 - 8495. Retrieved 2010/03/01.