(R)-8-Hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione

Base Information

• Chemical Name: (R)-8-Hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione
• CAS No.: 681001-30-9
• Molecular Formula: C19H16O3
• Molecular Weight: 292.32900
• DSSTox Substance ID: DTXSID80459572
• Wikidata: Q82283371
• Mol file: 681001-30-9.mol

Synonyms:681001-30-9;(R)-8-Hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione;(3R)-8-hydroxy-3-methyl-1,2,3,4-tetrahydrobenzo[a]anthracene-7,12-dione;(3R)-8-hydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-7,12-dione;DTXSID80459572;GEHDQJGXSHLDCP-SNVBAGLBSA-N;(R)-1,2,3,4-TETRAHYDRO-8-HYDROXY-3-METHYLTETRAPHENE-7,12-DIONE;AKOS025295626;AG-G-59753

Chemical Property of (R)-8-Hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione

Chemical Property:

• Vapor Pressure: 1.12E-11mmHg at 25°C
• Melting Point: 162°C
• Boiling Point: 525.9±50.0 °C(Predicted)
• PKA: 6.81±0.40(Predicted)
• PSA: 54.37000
• Density: 1.303±0.06 g/cm3(Predicted)
• LogP: 3.29240
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly),Methanol (Slightly)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 292.109944368
• Heavy Atom Count: 22
• Complexity: 485

Purity/Quality:

95% ^*data from raw suppliers

(R)-8-Hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2=C(C1)C=CC3=C2C(=O)C4=C(C3=O)C(=CC=C4)O
• Isomeric SMILES: C[C@@H]1CCC2=C(C1)C=CC3=C2C(=O)C4=C(C3=O)C(=CC=C4)O
• Uses: (R)-8-Hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione (cas# 681001-30-9) is a compound useful in organic synthesis.

Technology Process of (R)-8-Hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione

There total 12 articles about (R)-8-Hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione 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:

(4S)-4-benzyl-3-((R)-2-(prop-2-ynyl)hex-5-enoyl)oxazolidin-2-one (942513-96-4) → (R)-8-hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione (681001-30-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 82 percent / LiBH₄ / methanol; tetrahydrofuran / 2 h / 0 °C

2.1: 89 percent / pyridine; DMAP / 5 h / 20 °C

3.1: 100 percent / Grubbs first generation catalyst / toluene / 12 h / 80 °C

4.1: LAH / tetrahydrofuran / 12 h / 20 °C

5.1: toluene / 12 h / 80 °C

5.2: 0.21 g / K₂CO₃ / methanol / 12 h

With pyridine; dmap; lithium aluminium tetrahydride; lithium borohydride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; toluene; 5.1: Diels-Alder reaction;

DOI:10.1021/jo070709p

Reference yield:

(R)-2-(prop-2-ynyl)hex-5-en-1-ol (942513-97-5) → (R)-8-hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione (681001-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 89 percent / pyridine; DMAP / 5 h / 20 °C

2.1: 100 percent / Grubbs first generation catalyst / toluene / 12 h / 80 °C

3.1: LAH / tetrahydrofuran / 12 h / 20 °C

4.1: toluene / 12 h / 80 °C

4.2: 0.21 g / K₂CO₃ / methanol / 12 h

With pyridine; dmap; lithium aluminium tetrahydride; Grubbs catalyst first generation; In tetrahydrofuran; toluene; 4.1: Diels-Alder reaction;

DOI:10.1021/jo070709p

Reference yield:

(R)-2-(prop-2-ynyl)hex-5-enyl 4-methylbenzenesulfonate (949087-71-2) → (R)-8-hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione (681001-30-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / Grubbs first generation catalyst / toluene / 12 h / 80 °C

2.1: LAH / tetrahydrofuran / 12 h / 20 °C

3.1: toluene / 12 h / 80 °C

3.2: 0.21 g / K₂CO₃ / methanol / 12 h

With lithium aluminium tetrahydride; Grubbs catalyst first generation; In tetrahydrofuran; toluene; 3.1: Diels-Alder reaction;

DOI:10.1021/jo070709p

upstream raw materials:

(3R)-3-methylcyclohexanone

5-acetoxy-2-bromo-1,4-naphthoquinone

tri-n-butyl(vinyl)tin

(R)-5-methyl-1-vinylcyclohex-1-ene

Downstream raw materials:

(+)-rubiginone B2

(S)-8-hydroxy-3-methyl-3,4-dihydrotetraphene-1,7,12(2H)-trione