(E)-1α,3,4,7,8,9β,10,11-Octahydro-6,10,10-trimethyl-3-<<2-(methylamino)phenyl>sulfinyl>-2H-bicyclo<7.2.0>undecen-2-one

Base Information

Chemical Name:(E)-1α,3,4,7,8,9β,10,11-Octahydro-6,10,10-trimethyl-3-<<2-(methylamino)phenyl>sulfinyl>-2H-bicyclo<7.2.0>undecen-2-one
CAS No.:81491-38-5
Molecular Formula:C₂₁H₂₉NO₂S
Molecular Weight:359.533
Hs Code.:

Synonyms:

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Chemical Property of (E)-1α,3,4,7,8,9β,10,11-Octahydro-6,10,10-trimethyl-3-<<2-(methylamino)phenyl>sulfinyl>-2H-bicyclo<7.2.0>undecen-2-one

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Technology Process of (E)-1α,3,4,7,8,9β,10,11-Octahydro-6,10,10-trimethyl-3-<<2-(methylamino)phenyl>sulfinyl>-2H-bicyclo<7.2.0>undecen-2-one

There total 30 articles about (E)-1α,3,4,7,8,9β,10,11-Octahydro-6,10,10-trimethyl-3-<<2-(methylamino)phenyl>sulfinyl>-2H-bicyclo<7.2.0>undecen-2-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:

: 81491-37-4,81521-09-7,81570-11-8
(E)-(4S,7S)-2,6,6,10-Tetramethyl-14-oxo-14λ⁴-thia-2-aza-tricyclo[13.4.0.0^4,7]nonadeca-1(19),10,15,17-tetraen-3-one

: 81491-38-5,81521-10-0,81521-11-1
(E)-(1S,9S)-6,10,10-Trimethyl-3-(2-methylamino-benzenesulfinyl)-bicyclo[7.2.0]undec-5-en-2-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 40h; Yield given;
DOI:10.1021/jo00187a006

Reference yield:

: 81491-37-4
(E)-1α,7,8,11,12,13β,14,15-Octahydro-3,10,14,14-tetramethyl-4,5-benzo-3-aza-6-thia-2H-bicyclo<11.2.0>pentadecen-2-one 6-Oxide

: 81491-38-5
(E)-1α,3,4,7,8,9β,10,11-Octahydro-6,10,10-trimethyl-3-<<2-(methylamino)phenyl>sulfinyl>-2H-bicyclo<7.2.0>undecen-2-one

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; 1.)-78 deg C, 30 min., 2.)0 deg C, 30 min.;
DOI:10.1021/jo00187a006

Reference yield:

: 37676-91-8
methyl (3,3-dimethyl-1-cyclobutene)carboxylate

: 81491-38-5
(E)-1α,3,4,7,8,9β,10,11-Octahydro-6,10,10-trimethyl-3-<<2-(methylamino)phenyl>sulfinyl>-2H-bicyclo<7.2.0>undecen-2-one

Guidance literature:: Multi-step reaction with 16 steps

1: 357 mg / potassium tert-butoxide / tetrahydrofuran; dimethylsulfoxide / 144 h / Ambient temperature

2: 2percent KOH / H₂O; ethanol / 1.)1 h, r.t., 2.)2 h, reflux

3: pyridine / 2 h / Heating

4: K₂CO₃ / acetone / 12 h / Heating

5: 1.33 g / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

6: 1.65 g / Imidazol / dimethylformamide / Ambient temperature

7: 99.5 percent / n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.)-78 deg C, 2 h, 2.)1 h, ice-salt bath

8: 446 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

9: 84.2 percent / sodium amalgam, anh. sodium hydrogen phosphate / methanol / 1.)0 deg C, 2.)R_.T_.

10: 390 mg / Jones reagent / acetone / 0.5 h / 0 °C

11: Oxalyl chloride / benzene / 1.)30 min., r.t., 2.)2 h, 60-65 deg C

12: 550 mg / K₂CO₃ / tetrahydrofuran / 1.5 h / 0 °C

13: Dimethylsulfide, boron trifluoride etherate / CH₂Cl₂ / 0.67 h / 0 °C

14: 54.8 percent / K-tert-butylat / dioxane; 2-methyl-propan-2-ol / 55 - 60 °C

15: 89.5 percent / sodium m-periodate / H₂O; methanol / 1.)0 deg C, 2.)18 h, r.t.

16: 55 mg / Hexamethylphosphoramide, Lithium diisopropylamide / tetrahydrofuran / 1.)-78 deg C, 30 min., 2.)0 deg C, 30 min.

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium periodate; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; jones reagent; oxalyl dichloride; dimethylsulfide; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/jo00187a006