(+)-(2S,3'R)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-1-one

Base Information

Chemical Name:(+)-(2S,3'R)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-1-one
CAS No.:1321829-53-1
Molecular Formula:C₁₇H₁₃ClO₂
Molecular Weight:284.742
Hs Code.:

Synonyms:(+)-(2S,3'R)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-1-one

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Chemical Property of (+)-(2S,3'R)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-1-one

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Technology Process of (+)-(2S,3'R)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-1-one

There total 4 articles about (+)-(2S,3'R)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-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: 98.0%

: 49545-70-2,59082-24-5,59082-35-8
2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one

: 1321829-53-1
(+)-(2S,3'R)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-1-one

Guidance literature:: With tert.-butylhydroperoxide; [(Me₃Si)₂N]₃Yb^III(μ-Cl)Li(THF)₃; (S)-2,4-di-tert-butyl-6-[[2-(hydroxydiphenylmethyl)pyrrolidin-1-yl]methyl]phenol; In tetrahydrofuran; at 20 ℃; for 4h; enantioselective reaction; Schlenk technique; Inert atmosphere;
DOI:10.1021/acs.orglett.5b00833

Reference yield: 94.0%

: 17215-80-4
2-chloro-1-tetralone

: 104-88-1
4-chlorobenzaldehyde

: 1321829-53-1
(+)-(2S,3'R)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-1-one

Guidance literature:: 2-chloro-1-tetralone; With C₃₁H₃₈N₂O₈; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;

4-chlorobenzaldehyde; In tetrahydrofuran; at 0 ℃; for 36h; enantioselective reaction;
DOI:10.1039/c7cc06194c

Reference yield: 32.0%

: 49545-70-2,59082-24-5,59082-35-8
2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one

: 1321829-53-1
(+)-(2S,3'R)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-1-one

: 1379762-73-8
(-)-(2R,3'S)-3'-(4-chlorophenyl)-3,4-dihydro-1H-spiro-(naphthalene-2,2'-oxiran)-1-one

Guidance literature:: 2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one; With tris(bis(trimethylsilyl)amido)lanthanum(III); (S,S)-N,N'-di(3,5-dimethylsalicylidene)-1,2-cyclohexanediamine; In acetonitrile; for 0.5h; Inert atmosphere;

With tert.-butylhydroperoxide; In acetonitrile; at -20 ℃; for 10h; Overall yield = 32 %; enantioselective reaction; Inert atmosphere;
DOI:10.1039/c9ra01529a