(1S,9S)-(+)-5-(2-fluorophenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

Base Information

• Chemical Name: (1S,9S)-(+)-5-(2-fluorophenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene
• CAS No.: 409319-21-7
• Molecular Formula: C₁₈H₁₈FN
• Molecular Weight: 267.346

Synonyms:(1S,9S)-(+)-5-(2-fluorophenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

Chemical Property of (1S,9S)-(+)-5-(2-fluorophenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

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Technology Process of (1S,9S)-(+)-5-(2-fluorophenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

There total 3 articles about (1S,9S)-(+)-5-(2-fluorophenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene 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: 67.0%

(1S)-pinocarvone (19890-00-7) + 1-[2-(2-fluorophenyl)-2-oxoethyl]pyridinium iodide → (1S,9S)-(+)-5-(2-fluorophenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-triene (409319-21-7)

Guidance literature:

With ammonium acetate; acetic acid; for 6h; Heating;

DOI:10.1021/jo800246g

Reference yield:

2'-Fluoroacetophenone (445-27-2) → (1S,9S)-(+)-5-(2-fluorophenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-triene (409319-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / I₂ / 0.75 h / 100 °C

2: 46 percent / ammonium acetate / acetic acid / 4 h / 120 °C

With ammonium acetate; iodine; In acetic acid;

DOI:10.1016/S0040-4020(01)01002-X

Reference yield:

(-)-α-pinene (7785-26-4,25766-18-1) → (1S,9S)-(+)-5-(2-fluorophenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-triene (409319-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 5,15,10,20-tetraphenylporphyrin; acetic anhydride / Inert atmosphere

2.1: ammonium acetate / acetic acid / 110 °C / Inert atmosphere

2.2: 48 h / 110 °C / Inert atmosphere

With ammonium acetate; 5,15,10,20-tetraphenylporphyrin; acetic anhydride; In acetic acid; 2.1: |Kroehnke Pyridine Synthesis / 2.2: |Kroehnke Pyridine Synthesis;

DOI:10.1002/chem.201203817

upstream raw materials:

(1S)-pinocarvone

2'-Fluoroacetophenone

(-)-α-pinene

Downstream raw materials:

(1R,8S,9S)-(+)-5-(2-fluorophenyl)-8-isopropyl-10,10-dimethyl-6-azatricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

(1R,8S,9S)-(+)-5-(2-fluorophenyl)-8,10,10-trimethyl-6-azatricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

C₁₉H₂₀FNO

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