Hmdra

Base Information

• Chemical Name: Hmdra
• CAS No.: 113459-56-6
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.312
• DSSTox Substance ID: DTXSID70921076
• Mol file: 113459-56-6.mol

Synonyms:10-hydroxy-11-methoxydracaenone

Chemical Property of Hmdra

Chemical Property:

• Vapor Pressure: 2.19E-11mmHg at 25°C
• Boiling Point: 518.9°Cat760mmHg
• Flash Point: 196.8°C
• PSA: 66.76000
• Density: 1.42g/cm³
• LogP: 2.06540
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 284.10485899
• Heavy Atom Count: 21
• Complexity: 493

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2COCC(C23C=CC(=O)C=C3)C4=CC(=C(C=C41)O)O
• Isomeric SMILES: C1[C@@H]2COCC(C23C=CC(=O)C=C3)C4=CC(=C(C=C41)O)O

Technology Process of Hmdra

There total 9 articles about Hmdra 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: 62.0%

C20H24O5 → 10-hydroxy-11-methoxydracaenone (113459-56-6)

Guidance literature:

With phosphotungstic acid; bis-[(trifluoroacetoxy)iodo]benzene; In acetonitrile; at -25 - -7 ℃; for 1.5h;

DOI:10.1021/acs.orglett.8b03965

Reference yield:

C25H33NO5Si → 10-hydroxy-11-methoxydracaenone (113459-56-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: titanium tetrachloride / dichloromethane / 0.08 h / Inert atmosphere; Cooling with ice

1.2: 0.33 h / Inert atmosphere; Cooling with ice

1.3: 1.5 h / Inert atmosphere; Cooling with ice

2.1: methanol; lithium borohydride / diethyl ether / 2 h / Cooling with ice

3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 1.5 h / 20 °C

4.1: dmap; triethylamine / acetonitrile / 30 h / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / Cooling with ice

7.1: bis-[(trifluoroacetoxy)iodo]benzene; phosphotungstic acid / acetonitrile / 1.5 h / -25 - -7 °C

With methanol; triethylsilane; dmap; phosphotungstic acid; lithium borohydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.8b03965

Reference yield:

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde (97315-18-9) → 10-hydroxy-11-methoxydracaenone (113459-56-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: titanium tetrachloride / dichloromethane / 0.08 h / Inert atmosphere; Cooling with ice

1.2: 0.33 h / Inert atmosphere; Cooling with ice

1.3: 1.5 h / Inert atmosphere; Cooling with ice

2.1: methanol; lithium borohydride / diethyl ether / 2 h / Cooling with ice

3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 1.5 h / 20 °C

4.1: dmap; triethylamine / acetonitrile / 30 h / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / Cooling with ice

7.1: bis-[(trifluoroacetoxy)iodo]benzene; phosphotungstic acid / acetonitrile / 1.5 h / -25 - -7 °C

With methanol; triethylsilane; dmap; phosphotungstic acid; lithium borohydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.8b03965

upstream raw materials:

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde

Refernces

• 1、 Li, Mei-Mei,Wu, Yikang,Liu, Bo. "Synthesis and Configuration of Natural Dracaenones". . p. 575 - 578. Retrieved 2019/01/24.