Moracin D

Base Information

• Chemical Name: Moracin D
• CAS No.: 69120-07-6
• Molecular Formula: C19H16O4
• Molecular Weight: 308.334
• European Community (EC) Number: 826-027-5
• DSSTox Substance ID: DTXSID301178570
• Wikidata: Q104958500
• Metabolomics Workbench ID: 45981
• ChEMBL ID: CHEMBL463241
• Mol file: 69120-07-6.mol

Synonyms:Moracin D;69120-07-6;7-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethylchromen-5-ol;7-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethyl-2H-chromen-5-ol;7-(6-Hydroxybenzofuran-2-yl)-2,2-dimethyl-2H-chromen-5-ol;starbld0006163;CHEMBL463241;SCHEMBL6822795;CHEBI:174942;DTXSID301178570;BDBM50062362;AKOS032962426;HY-122943;CS-0090596;7-(6-hydroxy-1-benzouran-2-yl)-2,2-dimethylchromen-5-ol;2H-1-benzopyran-5-ol, 7-(6-hydroxy-2-benzofuranyl)-2,2-dimethyl-;7-(6-Hydroxy-2-benzofuranyl)-2,2-dimethyl-2H-1-benzopyran-5-ol;7-(6-Hydroxy-2-benzofuranyl)-2,2-dimethyl-2H-1-benzopyran-5-ol, 9CI

Chemical Property of Moracin D

Chemical Property:

• Boiling Point: 406.9±45.0 °C(Predicted)
• PKA: 9.06±0.40(Predicted)
• PSA: 62.83000
• Density: 1.295±0.06 g/cm3(Predicted)
• LogP: 4.69520
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 308.10485899
• Heavy Atom Count: 23
• Complexity: 474

Purity/Quality:

99%, ^*data from raw suppliers

MoracinD ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C=CC2=C(C=C(C=C2O1)C3=CC4=C(O3)C=C(C=C4)O)O)C

Technology Process of Moracin D

There total 29 articles about Moracin D 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: 92.0%

moracin D diacetate (69120-12-3) → moracin D (69120-07-6)

Guidance literature:

With ammonium hydroxide; In methanol; at 20 ℃; for 2h;

DOI:10.1039/c7ob02459b

Reference yield:

6-hydroxybenzofuran-3-one (6272-26-0) → moracin D (69120-07-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: sodium tetrahydroborate / methanol / 4 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: -78 - 20 °C

3.3: 20 °C / pH 5

4.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere

5.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C

6.1: n-butyllithium / hexane; cyclohexane / 0.5 h / Inert atmosphere; Heating

6.2: 2 h / Inert atmosphere; Heating

7.1: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane; benzene / 2 h / Reflux

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; palladium diacetate; potassium carbonate; diphenylphosphane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tricyclohexylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; hexane; cyclohexane; water; benzene;

DOI:10.1016/j.tetlet.2015.05.093

Reference yield:

recorcinol (108-46-3) → moracin D (69120-07-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1H-imidazole / tetrahydrofuran / 4 h / 20 °C

2: bromine / dichloromethane / 0.5 h / 0 °C

3: Pd(PPh₃)₂Cl₂; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C

4: ruthenium trichloride; sodium periodate; benzyltriethylammonium chloride / ethyl acetate / 2 h / 20 °C

5: tetrahydrofuran / 0 °C

6: toluene-4-sulfonic acid / toluene / Reflux

7: lithium diphenylphosphide / tetrahydrofuran / Reflux

8: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane; benzene / 2 h / Reflux

With 1H-imidazole; ruthenium trichloride; sodium periodate; copper(l) iodide; Pd(PPh₃)₂Cl₂; bromine; toluene-4-sulfonic acid; benzyltriethylammonium chloride; triethylamine; lithium diphenylphosphide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/j.tetlet.2015.05.093

upstream raw materials:

3-((tert-butyldimethylsilyl)oxy)phenol

C₁₂H₁₉BrO₂Si

moracin C

6-(tert-butyl-dimethylsilanyloxy)-[2H]-benzofuran-3-one

Refernces

• 1、 Wu, Deyan,Mei, Hanbing,Tan, Ping,Lu, Weiqiang,Zhu, Jin,Wang, Wei,Huang, Jin,Li, Jian. "Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus". . p. 4383 - 4387. Retrieved 2015/06/22.