(5S,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene

Base Information

Chemical Name:(5S,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene
CAS No.:189231-98-9
Molecular Formula:C₂₁H₂₈O₂S
Molecular Weight:344.518
Hs Code.:

Synonyms:(5S,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene

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Chemical Property of (5S,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene

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Technology Process of (5S,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene

There total 10 articles about (5S,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene 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: 85.0%

: 189232-15-3
4-Methyl-benzenesulfinic acid 1-[2-((R)-2,5-dimethyl-cyclopent-1-enyl)-1,1-dimethyl-ethyl]-prop-2-ynyl ester

: (5R,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene

: 189231-98-9
(5S,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene

Guidance literature:: With calcium carbonate; In 1,2-dichloro-benzene; at 130 ℃; for 3h; Yield given;
DOI:10.1016/S0040-4039(97)00475-9

Reference yield:

: 189232-13-1
((R)-2,5-Dimethyl-cyclopent-1-enyl)-methanol

: 189231-98-9
(5S,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene

Guidance literature:: Multi-step reaction with 5 steps

1: (COCl)2 / dimethylformamide / 2.5 h / 0 °C

2: 70 percent / ZnCl₂ / CH₂Cl₂ / 4 h / -50 - 0 °C

3: tetrahydrofuran / 1 h / -78 - -20 °C

4: NEt₃ / CH₂Cl₂ / 3 h / -78 deg C to r.t.

5: 85 percent / CaCO₃ / 1,2-dichloro-benzene / 3 h / 130 °C

With oxalyl dichloride; triethylamine; calcium carbonate; zinc(II) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene;
DOI:10.1016/S0040-4039(97)00475-9

Reference yield:

: 189232-14-2
(R)-2-Chloromethyl-1,3-dimethyl-cyclopentene

: 189231-98-9
(5S,9R)-3,3,6,9-Tetramethyl-1-(toluene-4-sulfonylmethyl)-spiro[4.4]nona-1,6-diene

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / ZnCl₂ / CH₂Cl₂ / 4 h / -50 - 0 °C

2: tetrahydrofuran / 1 h / -78 - -20 °C

3: NEt₃ / CH₂Cl₂ / 3 h / -78 deg C to r.t.

4: 85 percent / CaCO₃ / 1,2-dichloro-benzene / 3 h / 130 °C

With triethylamine; calcium carbonate; zinc(II) chloride; In tetrahydrofuran; dichloromethane; 1,2-dichloro-benzene;
DOI:10.1016/S0040-4039(97)00475-9