(R)-3alpha-Phenylindan-1-one

Base Information

• Chemical Name: (R)-3alpha-Phenylindan-1-one
• CAS No.: 634182-03-9
• Molecular Formula: C15H12O
• Molecular Weight: 208.26
• DSSTox Substance ID: DTXSID70361312
• Nikkaji Number: J2.413.352D
• Wikidata: Q82143592
• Mol file: 634182-03-9.mol

Synonyms:AC1LOJLK;(R)-3alpha-Phenylindan-1-one;634182-03-9;DTXSID70361312

Chemical Property of (R)-3alpha-Phenylindan-1-one

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 208.088815002
• Heavy Atom Count: 16
• Complexity: 265

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C2=CC=CC=C2C1=O)C3=CC=CC=C3
• Isomeric SMILES: C1[C@@H](C2=CC=CC=C2C1=O)C3=CC=CC=C3

Technology Process of (R)-3alpha-Phenylindan-1-one

There total 36 articles about (R)-3alpha-Phenylindan-1-one 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: 99.0%

2-(α-styryl)benzaldehyde (871563-46-1) → (R)-3-phenyl-2,3-dihydro-1H-inden-1-one (634182-03-9)

Guidance literature:

With ((2R,4R)-(-)-2,4-bis(diphenylphosphine)pentane); cobalt(II) chloride; zinc; In acetonitrile; at 25 ℃; for 12h; Reagent/catalyst; enantioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1021/ja509919x

Reference yield: 87.0%

(E)-1-(2-bromophenyl)-3-phenylprop-2-en-1-one (300657-41-4) → (R)-3-phenyl-2,3-dihydro-1H-inden-1-one (634182-03-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; benzoic acid; bis(dibenzylideneacetone)-palladium⁽⁰⁾; (R)-7,7'-bis[di(p-methylphenyl)phosphino]-1,1'-spirobiindane; In ethylene glycol; at 100 ℃; for 18h; Reagent/catalyst; Solvent; stereoselective reaction; Catalytic behavior; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201501712

Reference yield: 82.0%

(E)-1-(2-chlorophenyl)-3-phenylprop-2-en-1-one (144017-77-6) → (R)-3-phenyl-2,3-dihydro-1H-inden-1-one (634182-03-9)

Guidance literature:

With nickel(II) bromide dimethoxyethane; manganese; C₂₈H₃₃N₃O₂; water; lithium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 80 ℃; for 24h; enantioselective reaction; Inert atmosphere; Glovebox; Schlenk technique;

DOI:10.1021/acs.orglett.9b02130

upstream raw materials:

methyl 3-(2-benzylphenyl)-2-diazo-3-oxopropanoate

(E)-2-(3-phenylprop-2-enoyl)phenyl nonafluorobutanesulfonate

(E)-1-(2-iodophenyl)-3-phenylprop-2-en-1-one

(E)-1-(2-bromophenyl)-3-phenylprop-2-en-1-one

Downstream raw materials:

(1R,3R)-3-phenyl-2,3-dihydro-1H-inden-1-ol

(R)-4-(phenyl)-3,4-dihydrocoumarin

C₂₀H₁₄O₂

Refernces

• 1、 Qin, Xurong,Yao Lee, Marcus Wen,Zhou, Jianrong Steve. "Asymmetric Hydroarylation of Enones via Nickel-Catalyzed 5- Endo-Trig Cyclization". supporting information. p. 5990 - 5994. Retrieved 2019/08/20.
• 2、 Rastelli, Ettore J.,Truong, Ngoc T.,Coltart, Don M.. "Asymmetric Induction in Hydroacylation by Cooperative Iminium Ion-Transition-Metal Catalysis". supporting information. p. 5588 - 5591. Retrieved 2016/11/17.