1H-Indene-4-carboxylic acid, 2,3,5,6,7,7a-hexahydro-6,7-dihydroxy-, methyl ester, (6R,7S,7aR)-rel- (9CI)

Base Information

• Chemical Name: 1H-Indene-4-carboxylic acid, 2,3,5,6,7,7a-hexahydro-6,7-dihydroxy-, methyl ester, (6R,7S,7aR)-rel- (9CI)
• CAS No.: 452976-62-4
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.246
• Mol file: 452976-62-4.mol

Synonyms:1H-Indene-4-carboxylic acid, 2,3,5,6,7,7a-hexahydro-6,7-dihydroxy-, methyl ester, (6R,7S,7aR)-rel- (9CI)

Chemical Property of 1H-Indene-4-carboxylic acid, 2,3,5,6,7,7a-hexahydro-6,7-dihydroxy-, methyl ester, (6R,7S,7aR)-rel- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Indene-4-carboxylic acid, 2,3,5,6,7,7a-hexahydro-6,7-dihydroxy-, methyl ester, (6R,7S,7aR)-rel- (9CI)

There total 17 articles about 1H-Indene-4-carboxylic acid, 2,3,5,6,7,7a-hexahydro-6,7-dihydroxy-, methyl ester, (6R,7S,7aR)-rel- (9CI) 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:

2,3,5,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester (452976-60-2) → (4RS,5SR,6SR)-4,5-dihydroxy-2-(methoxycarbonyl)bicyclo[4.3.0]non-1-ene (452976-61-3,452976-62-4)

Guidance literature:

With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; acetone; tert-butyl alcohol; at -20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)00102-3

Reference yield:

6-trimethylsilanyl-hex-5-yn-1-ol (103437-52-1) → (4RS,5SR,6SR)-4,5-dihydroxy-2-(methoxycarbonyl)bicyclo[4.3.0]non-1-ene (452976-61-3,452976-62-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

2.1: 43.0 g / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 99 percent / DIBAH / hexane / 0.5 h / -78 °C

4.1: 79 percent / N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C

5.2: 87 percent / tetrahydrofuran; hexane / 0.5 h / -20 - 0 °C

6.1: MeLi / tetrahydrofuran; diethyl ether / 1.5 h / 0 °C

6.2: 67 percent / tetrahydrofuran; diethyl ether / 0.5 h / -30 °C

7.1: toluene / 2.5 h / Heating

8.1: 691 mg / N-methylmorpholine N-oxide / OsO₄ / acetone; 2-methyl-propan-2-ol; H₂O / 0.5 h / -20 °C

With n-butyllithium; 4 A molecular sieve; methyllithium; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; osmium(VIII) oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 2.1: Wittig reaction / 5.2: Wittig reaction / 7.1: Diels-Alder reaction;

DOI:10.1016/S0040-4020(02)00102-3

Reference yield:

6-trimethylsilanyl-hex-5-yn-1-ol (103437-52-1) → (4RS,5SR,6RS)-4,5-dihydroxy-2-(methoxycarbonyl)bicyclo[4.3.0]non-1-ene (452976-61-3,452976-62-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

2.1: 43.0 g / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 99 percent / DIBAH / hexane / 0.5 h / -78 °C

4.1: 79 percent / N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C

5.2: 87 percent / tetrahydrofuran; hexane / 0.5 h / -20 - 0 °C

6.1: MeLi / tetrahydrofuran; diethyl ether / 1.5 h / 0 °C

6.2: 67 percent / tetrahydrofuran; diethyl ether / 0.5 h / -30 °C

7.1: toluene / 2.5 h / Heating

8.1: I₂ / acetic acid; H₂O / 2 h / Heating

9.1: 370 mg / aq. KOH / methanol / 24 h

With potassium hydroxide; n-butyllithium; 4 A molecular sieve; methyllithium; iodine; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetic acid; toluene; 2.1: Wittig reaction / 5.2: Wittig reaction / 7.1: Diels-Alder reaction;

DOI:10.1016/S0040-4020(02)00102-3

upstream raw materials:

2,3,5,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

6-trimethylsilanyl-hex-5-yn-1-ol

6-(trimethylsilyl)-5-hexynal

ethyl 8-(trimethylsilyl)-(E)-2-octen-7-ynonate

Refernces