trans-1,3-Diphenyl-2-propen-1-ol

• CAS: 62668-02-4
• Catalog Number: ACM62668024-2
• Category: Alkanes
• Molecular Weight: 210.27
• Molecular Formula: C₅H₆O₃
• Synonyms: 1,3-Diphenyl-2-propen-1-ol, 43200_ALDRICH, 1,3-diphenylprop-2-en-1-ol, 43200_FLUKA, trans-1,3-Diphenyl-2-propen-1-ol, MolPort-001-788-490, CID5712032, EC-000.1428, D2808, LT03329774, 62668-02-4
• IUPAC Name: (E)-1,3-diphenylprop-2-en-1-ol
• Canonical SMILES: C1=CC=C(C=C1)C=CC(C2=CC=CC=C2)O
• InChI Key: ORACYDGVNJGDMI-VAWYXSNFSA-N
• Boiling Point: 368.471ºC at 760 mmHg
• Melting Point: 55-57ºC
• Flash Point: 160.31ºC
• Density: 1.11 g/cm³
• Exact Mass: 210.10400
• Hazard Statements: H411
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• RIDADR: UN 3334
• Safety Description: S26-S36
• Symbol: GHS09

Case Study

Trans-Catalytic Hydrogenation of Trans-1,3-Diphenyl-2-Propene-1-Ol for Synthesis of Substituted Cyclopropanes

Kaper, Helena, et al. ChemCatChem, 2012, 4(11), 1813-1818.

Researchers created high surface area ZrO2-SiO2 mixed oxides to serve as catalysts for the trans-hydrogenation of trans-1,3-diphenyl-2-propene-1-ol. The method allows us to synthesize substituted cyclopropanes (vital intermediates in organic synthesis) in a one-pot synthesis through intramolecular alkylation followed by transfer hydrogenation.
The compound trans-1,3-diphenyl-2-propen-1-ol will initially experience intramolecular Friedel-Crafts alkylation in SiZr5's presence to form either a 5-membered or a 3-membered non-aromatic unsaturated ring. The ring structure becomes partially hydrogenated through further reaction with the residual reactants. This ring can then be hydrogenated by remaining reactants to produce a partially hydrogenated compound.
The research tested the stated hypothesis by heating trans-1,3-diphenyl-2-propen-1-ol at 110°C for 15 hours in octane solvent with SiZr5. The main products identified were 1,2-diphenyl cyclopropane and trans-1,3-diphenyl-2-propen-1-one, yielding 38% and 35%, respectively, thereby confirming the feasibility of the anticipated tandem reaction along pathway 2. To enhance the cyclopropane yield, the reaction was repeated using benzyl alcohol as both the solvent and a sacrificial reducing agent, leading to a yield of up to 63% for the cyclopropane.

Tunable Regioselective Aniline Allylation of Trans-1,3-Diphenyl-2-Propen-1-Ol

Albert-Soriano, et al. Advanced Synthesis & Catalysis, 2020, 362(12), 2494-2502.

This study demonstrated how allylic alcohols such as trans-1,3-diphenyl-2-propen-1-ol react with aniline using a metal-free catalyst to exclusively produce N-, 2-, and 4-allylaniline isomers.
· N-allylaniline isomers: When 1,3-bis(carboxymethyl)imidazolium chloride (bcmim-Cl) catalyzed the reaction between trans-1,3-diphenyl-2-propen-1-ol and aniline at 80 ºC, product 3aa formed selectively achieving an 82% conversion rate after 90 minutes while other isomers yielded less than 5%. The reaction time extended from 6 to 24 hours led to an increase in isomer 4aa formation to 14-18% and resulted in 14% conversion to isomer 5aa.
· 2-Allylaniline isomers: The 2-allylation of trans-1,3-diphenyl-2-propen-1-ol, catalyzed by bcmim-Br, was performed using various anilines. Aniline, 4-toluidine, 4-anisidine, and 4-phenoxyaniline yielded the corresponding products 4aa-4ad, with conversions ranging from 60% to 93%. Halogen-substituted anilines also produced the desired 2-allylanilines with moderate conversion rates.
· 4-Allylaniline isomers: The reaction of trans-1,3-diphenyl-2-propen-1-ol with bcmim-I and several substituted anilines was studied under optimized conditions to synthesize 4-allylaniline derivatives. Anilines with electron-withdrawing groups resulted in excellent conversions to the corresponding 4-allylanilines. Additionally, 2-Chloro-6-methylaniline and 2,6-diisopropylaniline as ortho-substituted anilines produced compounds 5am and 5an respectively in quantitative yields.

Custom Q&A

What is the IUPAC name of trans-1,3-Diphenyl-2-propen-1-ol?

The IUPAC name of trans-1,3-Diphenyl-2-propen-1-ol is (E)-1,3-diphenylprop-2-en-1-ol.

What is the molecular formula of trans-1,3-Diphenyl-2-propen-1-ol?

The molecular formula of trans-1,3-Diphenyl-2-propen-1-ol is C15H14O.

What is the molecular weight of trans-1,3-Diphenyl-2-propen-1-ol?

The molecular weight of trans-1,3-Diphenyl-2-propen-1-ol is 210.27 g/mol.

What is the CAS number of trans-1,3-Diphenyl-2-propen-1-ol?

The CAS number of trans-1,3-Diphenyl-2-propen-1-ol is 4663-33-6.

How many hydrogen bond donor counts does trans-1,3-Diphenyl-2-propen-1-ol have?

Trans-1,3-Diphenyl-2-propen-1-ol has 1 hydrogen bond donor count.

How many hydrogen bond acceptor counts does trans-1,3-Diphenyl-2-propen-1-ol have?

Trans-1,3-Diphenyl-2-propen-1-ol has 1 hydrogen bond acceptor count.

How many rotatable bond counts does trans-1,3-Diphenyl-2-propen-1-ol have?

Trans-1,3-Diphenyl-2-propen-1-ol has 3 rotatable bond counts.

What is the topological polar surface area of trans-1,3-Diphenyl-2-propen-1-ol?

The topological polar surface area of trans-1,3-Diphenyl-2-propen-1-ol is 20.2 Ų.

How many heavy atoms does trans-1,3-Diphenyl-2-propen-1-ol have?

Trans-1,3-Diphenyl-2-propen-1-ol has 16 heavy atoms.

Is trans-1,3-Diphenyl-2-propen-1-ol a canonicalized compound?

Yes, trans-1,3-Diphenyl-2-propen-1-ol is a canonicalized compound.