(5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Base Information

Chemical Name:(5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline
CAS No.:1007589-02-7
Molecular Formula:C₁₈H₁₉NO
Molecular Weight:265.355
Hs Code.:

Synonyms:(5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Suppliers and Price of (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

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Technology Process of (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

There total 7 articles about (5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline 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: 91.0%

: (5S,7R)-6,6-dimethyl-2-phenyl-5,7-methanoquinolin-8(5H)-one

: 1007589-02-7
(5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 20 - 22 ℃; for 0.333333h; Inert atmosphere;
DOI:10.1016/j.tet.2011.05.075

Reference yield:

: 1316251-07-6
C₁₈H₁₉NO

: 1007589-02-7
(5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

: (5S,7R,8R)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Guidance literature:: C₁₈H₁₉NO; With acetic anhydride; at 110 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In water; for 1.5h; Reflux; Inert atmosphere;

With sodium hydroxide; In water; pH=12 - 13; optical yield given as %de; Cooling with ice; Inert atmosphere;
DOI:10.1016/j.tet.2011.05.075

Reference yield:

: 110-86-1
pyridine

: 1007589-02-7
(5S,7R,8S)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

: (5S,7R,8R)-2-phenyl-8-hydroxy-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinoline

Guidance literature:: Multi-step reaction with 4 steps

1.1: iodine

2.1: ammonium acetate

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: acetic anhydride / 2 h / 110 °C / Inert atmosphere

4.2: 1.5 h / Reflux; Inert atmosphere

4.3: pH 12 - 13 / Cooling with ice; Inert atmosphere

With ammonium acetate; iodine; acetic anhydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 2.1: Krohnke reaction / 4.1: Boekelheide rearrangement;
DOI:10.1016/j.tet.2011.05.075