Temarotene

Base Information

• Chemical Name: Temarotene
• CAS No.: 89410-65-1
• Molecular Formula: C₂₃H₂₈
• Molecular Weight: 304.475
• UNII: A28G39IJ7K
• Nikkaji Number: J328.485I
• Wikidata: Q27273528
• NCI Thesaurus Code: C63953
• ChEMBL ID: CHEMBL554474
• Mol file: 89410-65-1.mol

Synonyms:1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-(1-methyl)-2-(phenylethenyl)naphthalene;Ro 15-0778;temarotene;temarotene, (E)-isomer

Chemical Property of Temarotene

Chemical Property:

• PSA: 0.00000
• LogP: 6.59610
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 304.219100893
• Heavy Atom Count: 23
• Complexity: 433

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1=CC=CC=C1)C2=CC3=C(C=C2)C(CCC3(C)C)(C)C
• Isomeric SMILES: C/C(=C\C1=CC=CC=C1)/C2=CC3=C(C=C2)C(CCC3(C)C)(C)C

Technology Process of Temarotene

There total 25 articles about Temarotene 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: 86.0%

(E)-1-fluoro-4-(2-phenylprop-1-enyl)benzene (83832-05-7) + 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (27452-17-1) → (E)-1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-(1-methyl-2-phenylethenyl)-naphthalene (75078-91-0,89410-65-1)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine; In N,N-dimethyl-formamide; at 80 ℃; Inert atmosphere;

DOI:10.1039/c0cc04496b

Reference yield: 55.0%

(E)-1-phenylthio-2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl]-1-propene (1398115-53-1) + phenylzinc(II) bromide (38111-44-3) → (E)-1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-(1-methyl-2-phenylethenyl)-naphthalene (75078-91-0,89410-65-1)

Guidance literature:

With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; In tetrahydrofuran; for 2.5h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2012.07.092

Reference yield: 50.0%

C14H19BN2 + 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (27452-17-1) → (Z)-1,1,4,4-tetramethyl-6-(1-phenylprop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene (89410-65-1)

Guidance literature:

C₁₄H₁₉BN₂; With N-chloro-succinimide; In 1,4-dioxane; at 20 ℃; for 0.25h;

6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium carbonate; for 3h; Reflux;

DOI:10.1002/anie.201804515

upstream raw materials:

benzaldehyde

[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-ethyl]-triphenylphosphonium bromide

6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene

phenylacetylene