5,6,8,9-tetramethoxy-4-(methoxy-d₃)-3-(phenylmethylene)spiro<2H-benzindene-2,1'-cyclopentan>-1(3H)-one

Base Information

• Chemical Name: 5,6,8,9-tetramethoxy-4-(methoxy-d₃)-3-(phenylmethylene)spiro<2H-benzindene-2,1'-cyclopentan>-1(3H)-one
• CAS No.: 139219-27-5
• Molecular Formula: C₂₉H₃₀O₆
• Molecular Weight: 477.53

Synonyms:5,6,8,9-tetramethoxy-4-(methoxy-d₃)-3-(phenylmethylene)spiro<2H-benzindene-2,1'-cyclopentan>-1(3H)-one

Chemical Property of 5,6,8,9-tetramethoxy-4-(methoxy-d₃)-3-(phenylmethylene)spiro<2H-benzindene-2,1'-cyclopentan>-1(3H)-one

Chemical Property:

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Technology Process of 5,6,8,9-tetramethoxy-4-(methoxy-d₃)-3-(phenylmethylene)spiro<2H-benzindene-2,1'-cyclopentan>-1(3H)-one

There total 10 articles about 5,6,8,9-tetramethoxy-4-(methoxy-d₃)-3-(phenylmethylene)spiro<2H-benzindene-2,1'-cyclopentan>-1(3H)-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: 4.0%

<1-(phenylseleno)-cyclopentyl><1,5,6,8-tetramethoxy-4-(methoxy-d3)-3-(phenylethynyl)-2-naphthalenyl>methanone (153617-90-4) → 5,6,8,9-tetramethoxy-4-(methoxy-d3)-3-(phenylmethylene)spiro<2H-benzindene-2,1'-cyclopentan>-1(3H)-one (139219-27-5) + 3,3a-dihydro-6,7,9,10-tetramethoxy-3-phenylspiro<4H-benz<5,6>indeno<7,1-bc>pyran-4,1'-cyclopentan>-5(2H)-one-2,2,3-d3

Guidance literature:

With 2,2'-azobis(isobutyronitrile); triphenylstannane; In benzene; Heating;

DOI:10.1016/S0040-4020(01)88016-9

Reference yield:

3-bromo-4,5,7,8-tetramethoxy-2-(phenylethynyl)-1-naphthalenol (139219-31-1) → 5,6,8,9-tetramethoxy-4-(methoxy-d3)-3-(phenylmethylene)spiro<2H-benzindene-2,1'-cyclopentan>-1(3H)-one (139219-27-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / NaH (60percent in oil) / dimethylformamide / 2.5 h / Ambient temperature

2: 1) n-BuLi / 1) THF, hexane, -78 deg C, 5 min, 2) THF, hexane, -78 deg C, 20 min

3: 60 percent / DDQ / dioxane / 100 °C

4: 88 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

5: tetrahydrofuran / -78 - 20 °C

6: 75 percent / Ph₃SnH, AIBN / benzene / Heating

With n-butyllithium; 2,2'-azobis(isobutyronitrile); triphenylstannane; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)88016-9

Reference yield:

α-cyclopentyl-1,5,6,8-tetramethoxy-4-(methoxy-d3)-3-(phenylethynyl)-2-naphthalenemethanol (139219-33-3) → 5,6,8,9-tetramethoxy-4-(methoxy-d3)-3-(phenylmethylene)spiro<2H-benzindene-2,1'-cyclopentan>-1(3H)-one (139219-27-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / DDQ / dioxane / 100 °C

2: 88 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: tetrahydrofuran / -78 - 20 °C

4: 75 percent / Ph₃SnH, AIBN / benzene / Heating

With 2,2'-azobis(isobutyronitrile); triphenylstannane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)88016-9

upstream raw materials:

<1-(phenylseleno)-cyclopentyl><1,5,6,8-tetramethoxy-4-(methoxy-d₃)-3-(phenylethynyl)-2-naphthalenyl>methanone

cyclopentanealdehyde

3-bromo-4,5,7,8-tetramethoxy-2-(phenylethynyl)-1-naphthalenol

2-bromo-1,5,6,8-tetramethoxy-4-(methoxy-d₃)-3-(phenylethynyl)naphthalene

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