Methyl 4-phenylcubanecarboxylate

Base Information

• Chemical Name: Methyl 4-phenylcubanecarboxylate
• CAS No.: 123675-82-1
• Molecular Formula: C16H14 O2
• Molecular Weight: 238.286
• Hs Code.: 2916200090
• DSSTox Substance ID: DTXSID50577732
• Wikidata: Q82467816
• Mol file: 123675-82-1.mol

Synonyms:Methyl 4-phenylcubanecarboxylate;123675-82-1;methyl 4-phenylcubane-1-carboxylate;Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1-carboxylic acid, 4-phenyl-, methyl ester;methyl (1s,2R,3r,8S)-4-phenylcubane-1-carboxylate;DTXSID50577732;Methyl 4-phenylpentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane-1-carboxylate

Chemical Property of Methyl 4-phenylcubanecarboxylate

Chemical Property:

• Vapor Pressure: 0.000184mmHg at 25°C
• Refractive Index: 1.753
• Boiling Point: 328.9°C at 760 mmHg
• Flash Point: 145.9°C
• PSA: 26.30000
• Density: 1.514g/cm³
• LogP: 1.84900
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 238.099379685
• Heavy Atom Count: 18
• Complexity: 428

Purity/Quality:

98%min ^*data from raw suppliers

Methyl (1S,2R,3R,8S)-4-phenylcubane-1-carboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C12C3C4C1C5C2C3C45C6=CC=CC=C6

Technology Process of Methyl 4-phenylcubanecarboxylate

There total 6 articles about Methyl 4-phenylcubanecarboxylate 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: 71.0%

4-(methoxycarbonyl)-1-cubanecarboxylic acid (24539-28-4) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → Methyl 1-phenylcubane-4-carboxylate (123675-82-1)

Guidance literature:

With lead(IV) acetate; for 3h; Irradiation;

DOI:10.1021/ja00053a008

Reference yield: 55.0%

phenylzinc chloride lithium chloride + C19H9Cl4NO6 → Methyl 1-phenylcubane-4-carboxylate (123675-82-1)

Guidance literature:

With (1,2-dimethoxyethane)dichloronickel(II); 4,4'-bis(carbomethoxy)-2,2'-bipyridine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/chem.201704344

Reference yield: 25.0%

1-(1,3-dioxoisoindolin-2-yl) 4-methyl cubane-1,4-dicarboxylate + diphenylzinc (1078-58-6) → Methyl 1-phenylcubane-4-carboxylate (123675-82-1)

Guidance literature:

1-(1,3-dioxoisoindolin-2-yl) 4-methyl cubane-1,4-dicarboxylate; diphenylzinc; With iron(III)-acetylacetonate; o-phenylenebis(diphenylphosphine); In tetrahydrofuran; at 0 - 25 ℃; for 1h; Inert atmosphere;

Inert atmosphere;

DOI:10.1021/jacs.6b07172

upstream raw materials:

4-(methoxycarbonyl)-1-cubanecarboxylic acid

benzene

diphenylzinc

phenylmagnesium bromide

Downstream raw materials:

4-phenyl-1-cubanecarboxylic acid

Refernces

• 1、 Kuduva, Srinivasan S.,Craig, Donald C.,Nangia, Ashwini,Desiraju, Gautam R.. "Cubanecarboxylic acids. Crystal engineering considerations and the role of C-H...O hydrogen bonds in determining O-H...Onetworks". . p. 1936 - 1944. Retrieved 1999.
• 2、 Toriyama, Fumihiko,Cornella, Josep,Wimmer, Laurin,Chen, Tie-Gen,Dixon, Darryl D.,Creech, Gardner,Baran, Phil S.. "Redox-Active Esters in Fe-Catalyzed C-C Coupling". supporting information. p. 11132 - 11135. Retrieved 2016/10/12.