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Cas Database

100420-75-5

100420-75-5

Identification

  • Product Name:(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

  • CAS Number: 100420-75-5

  • EINECS:

  • Molecular Weight:206.309

  • Molecular Formula: C12H14OS

  • HS Code:

  • Mol File:100420-75-5.mol

Synonyms:

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Relevant articles and documentsAll total 2 Articles be found

STEREOSPECIFIC CYCLISATIONS OF SUBSTITUTED α'-LITHIATED α(Z),γ-BUTADIENYL SULFOXIDES

Reglier, Marius,Julia, Sylvestre A.

, p. 2655 - 2658 (1985)

The title compounds 2(b-d) were prepared and converted stereospecifically to the lithiated derivatives of cyclic sulfoxides 3(b-d) through a proposed concerted disrotatory electrocyclisation.

Synthesis and properties of substituted α'-lithiated α(Z),γ-butadienyl sulfoxides. Part I : Structural studies on sulfoxides obtained by stereospecific cyclisation of these compounds.

Reglier, M.,Julia, S. A.

, p. 226 - 235 (2007/10/02)

The lithio-derivatives of sulfoxides 2b,c were prepared and gave stereospecifically after protonation the 2β-substituted 3,6-dihydro-4-methyl-2H-thiopyran-1α-oxides 3b,c.The latter were converted into the 1β-oxide 9b, the 2-substituted 3,6-dihydro-4-methyl-2H-thiopyrans 8b,c and the corresponding sulfones 10b,c.By comparison of the NMR spectra of these compounds as well as the effects of solvent (benzene) and europium salts on the chemical shifts of sulfoxides, the trans orientation of the sulfoxide group and R for 3b,c has been established.

Process route upstream and downstream products

Process route

3-Methyl-1-benzylsulfinylbuta-1(Z),3-diene
100420-59-5

3-Methyl-1-benzylsulfinylbuta-1(Z),3-diene

(3-Methylbuta-1(E),3-dienylsulfinyl)methylbenzene
100440-52-6

(3-Methylbuta-1(E),3-dienylsulfinyl)methylbenzene

(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

Conditions
Conditions Yield
With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h;
55%
18%
With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h; Var. time and temp.;
18%
55%
4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran
87362-82-1

4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran

(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

Conditions
Conditions Yield
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 15 ℃; Yield given. Yields of byproduct given;
4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran
87362-82-1

4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran

(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

Conditions
Conditions Yield
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 15 ℃; Yield given. Yields of byproduct given;
((Z)-3-Methyl-buta-1,3-dienylsulfanylmethyl)-benzene
87362-76-3

((Z)-3-Methyl-buta-1,3-dienylsulfanylmethyl)-benzene

(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 55 percent / m-CPBA / CH2Cl2 / -78 - 15 °C
2: 55 percent / LDA / tetrahydrofuran / 2 h / -78 °C / Var. time and temp.
With 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
((Z)-3-Methyl-buta-1,3-dienylsulfanylmethyl)-benzene
87362-76-3

((Z)-3-Methyl-buta-1,3-dienylsulfanylmethyl)-benzene

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 55 percent / m-CPBA / CH2Cl2 / -78 - 15 °C
2: 55 percent / LDA / tetrahydrofuran / 2 h / -78 °C / Var. time and temp.
3: 1.) Et3O(1+)*BF4(1-), 2.) NaOH / 1.) CH2Cl2
With sodium hydroxide; triethyloxonium fluoroborate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran
87362-82-1

4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: m-CPBA / CH2Cl2 / -78 - 15 °C
2: 1.) Et3O(1+)*BF4(1-), 2.) NaOH / 1.) CH2Cl2
With sodium hydroxide; triethyloxonium fluoroborate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
3-Methyl-1-benzylsulfinylbuta-1(Z),3-diene
100420-59-5

3-Methyl-1-benzylsulfinylbuta-1(Z),3-diene

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 55 percent / LDA / tetrahydrofuran / 2 h / -78 °C / Var. time and temp.
2: 1.) Et3O(1+)*BF4(1-), 2.) NaOH / 1.) CH2Cl2
With sodium hydroxide; triethyloxonium fluoroborate; lithium diisopropyl amide; In tetrahydrofuran;
(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1R,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide
100420-64-2,100420-75-5

(1S,2S)-4-Methyl-2-phenyl-3,6-dihydro-2H-thiopyran 1-oxide

Conditions
Conditions Yield
With sodium hydroxide; triethyloxonium fluoroborate; Yield given. Multistep reaction; 1.) CH2Cl2;
3-Methyl-1-benzylsulfinylbuta-1(Z),3-diene
100420-59-5

3-Methyl-1-benzylsulfinylbuta-1(Z),3-diene

(3-Methylbuta-1(E),3-dienylsulfinyl)methylbenzene
100440-52-6

(3-Methylbuta-1(E),3-dienylsulfinyl)methylbenzene

3,6-Dihydro-4-methyl-1α-oxydo-2β-phenyl 2H-thiopyrane
100420-64-2,100420-75-5

3,6-Dihydro-4-methyl-1α-oxydo-2β-phenyl 2H-thiopyrane

Conditions
Conditions Yield
Mechanism; multistep reaction, structural studies on sulfoxides obtained by stereospecific cyclisation of α'-lithiated α(Z),γ-butadienyl sulfoxides;
56%
18%
With water; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -30 deg C, 2 h, 2.) -30 deg C to ambient temperature, 30 min;
3,6-Dihydro-4-methyl-1α-oxydo-2β-phenyl 2H-thiopyrane
100420-64-2,100420-75-5

3,6-Dihydro-4-methyl-1α-oxydo-2β-phenyl 2H-thiopyrane

Conditions
Conditions Yield
With triethyloxonium fluoroborate; In dichloromethane;
50%

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