10-[4-(tert-butyldimethylsilyloxy)phenyl]dispiro[acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.1^3,7]decane]

Base Information

• Chemical Name: 10-[4-(tert-butyldimethylsilyloxy)phenyl]dispiro[acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.1^3,7]decane]
• CAS No.: 206645-79-6
• Molecular Formula: C₃₅H₄₁NO₃Si
• Molecular Weight: 551.801

Synonyms:10-[4-(tert-butyldimethylsilyloxy)phenyl]dispiro[acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.1^3,7]decane]

Chemical Property of 10-[4-(tert-butyldimethylsilyloxy)phenyl]dispiro[acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.1^3,7]decane]

Chemical Property:

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Technology Process of 10-[4-(tert-butyldimethylsilyloxy)phenyl]dispiro[acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.1^3,7]decane]

There total 9 articles about 10-[4-(tert-butyldimethylsilyloxy)phenyl]dispiro[acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.1^3,7]decane] 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:

9-Adamantan-2-ylidene-10-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-9,10-dihydro-acridine (206645-74-1) → 10-[4-(tert-butyldimethylsilyloxy)phenyl]dispiro[acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.13,7]decane] (206645-79-6)

Guidance literature:

With polymer supported Rose-Bengal; oxygen; In dichloromethane; at -78 ℃; for 2h; Yield given; Irradiation;

DOI:10.3987/COM-97-S(N)85

Reference yield:

2-Adamantanone (700-58-3) → 10-[4-(tert-butyldimethylsilyloxy)phenyl]dispiro[acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.13,7]decane] (206645-79-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / LiAlH₄, TiCl₃, Et₃N / tetrahydrofuran / 17 h / Heating

2: 98 percent / HBr / 24 h / Heating

3: 59 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

4: polymer supported Rose-Bengal, O₂ / CH₂Cl₂ / 2 h / -78 °C / Irradiation

With 1H-imidazole; lithium aluminium tetrahydride; titanium(III) chloride; polymer supported Rose-Bengal; hydrogen bromide; oxygen; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/COM-97-S(N)85

Reference yield:

2-(phenylamino)benzoic acid (91-40-7) → 10-[4-(tert-butyldimethylsilyloxy)phenyl]dispiro[acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.13,7]decane] (206645-79-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / K₂CO₃, Cu / nitrobenzene / 8 h / 200 °C

2: 22 percent / conc. H₂SO₄ / 2 h / 90 °C

3: 84 percent / LiAlH₄, TiCl₃, Et₃N / tetrahydrofuran / 17 h / Heating

4: 98 percent / HBr / 24 h / Heating

5: 88 percent / pyridine / 8 h / Ambient temperature

6: polymer supported Rose-Bengal, O₂ / CH₂Cl₂ / 2 h / -78 °C / Irradiation

With pyridine; lithium aluminium tetrahydride; titanium(III) chloride; polymer supported Rose-Bengal; sulfuric acid; hydrogen bromide; oxygen; copper; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; nitrobenzene;

DOI:10.3987/COM-97-S(N)85

upstream raw materials:

9-Adamantan-2-ylidene-10-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-9,10-dihydro-acridine

2-Adamantanone

2-(phenylamino)benzoic acid

para-iodoanisole

Downstream raw materials:

2-Adamantanone

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