N-benzyl-1,2,3,4-tetrahydro-6-hydroxy-6-(1-hexynyl)-cyclobutapyridin-5-one

Base Information

• Chemical Name: N-benzyl-1,2,3,4-tetrahydro-6-hydroxy-6-(1-hexynyl)-cyclobutapyridin-5-one
• CAS No.: 135831-90-2
• Molecular Formula: C₂₀H₂₃NO₂
• Molecular Weight: 309.408

Synonyms:N-benzyl-1,2,3,4-tetrahydro-6-hydroxy-6-(1-hexynyl)-cyclobutapyridin-5-one

Chemical Property of N-benzyl-1,2,3,4-tetrahydro-6-hydroxy-6-(1-hexynyl)-cyclobutapyridin-5-one

Chemical Property:

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Technology Process of N-benzyl-1,2,3,4-tetrahydro-6-hydroxy-6-(1-hexynyl)-cyclobutapyridin-5-one

There total 4 articles about N-benzyl-1,2,3,4-tetrahydro-6-hydroxy-6-(1-hexynyl)-cyclobutapyridin-5-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: 67.0%

1-hexynyllithium (17689-03-1) + N-benzyl-1,2,3,4-tetrahydrocyclobutapyridine-5,6-dione (135831-80-0) → N-benzyl-1,2,3,4-tetrahydro-6-hydroxy-6-(1-hexynyl)-cyclobutapyridin-5-one (135831-90-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/jo00022a031

Reference yield:

3-(benzylamino)-4-(3-hydroxypropyl)-3-cyclobutene-1,2-dione (135831-83-3) → N-benzyl-1,2,3,4-tetrahydro-6-hydroxy-6-(1-hexynyl)-cyclobutapyridin-5-one (135831-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / DEAD, PPh₃ / tetrahydrofuran / Ambient temperature

2: 67 percent / tetrahydrofuran / 1 h / -78 °C

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jo00022a031

Reference yield:

3-(benzylamino)-4-<3-(tetrahydropyranyloxy)propyl>-3-cyclobutene-1,2-dione (135831-82-2) → N-benzyl-1,2,3,4-tetrahydro-6-hydroxy-6-(1-hexynyl)-cyclobutapyridin-5-one (135831-90-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / conc. HCl / H₂O / 1.5 h / 60 °C / Heating

2: 65 percent / DEAD, PPh₃ / tetrahydrofuran / Ambient temperature

3: 67 percent / tetrahydrofuran / 1 h / -78 °C

With hydrogenchloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; water;

DOI:10.1021/jo00022a031

upstream raw materials:

1-hexynyllithium

N-benzyl-1,2,3,4-tetrahydrocyclobutapyridine-5,6-dione

3-(benzylamino)-4-(3-hydroxypropyl)-3-cyclobutene-1,2-dione

3-(benzylamino)-4-<3-(tetrahydropyranyloxy)propyl>-3-cyclobutene-1,2-dione

Downstream raw materials:

1-Benzyl-6-butyl-1,2,3,4-tetrahydro-quinoline-5,8-dione

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