7,8-dihydroxy-5,6-epoxy-1,4-dimethyl-5,6,7,8-tetrahydrophenanthrene

Base Information

• Chemical Name: 7,8-dihydroxy-5,6-epoxy-1,4-dimethyl-5,6,7,8-tetrahydrophenanthrene
• CAS No.: 122033-85-6
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.301
• Mol file: 122033-85-6.mol

Synonyms:Phenanthro[3,4-b]oxirene-2,3-diol,1a,2,3,9c-tetrahydro-6,9-dimethyl-, (1aa,2a,3b,9ca)-(?à)-

Chemical Property of 7,8-dihydroxy-5,6-epoxy-1,4-dimethyl-5,6,7,8-tetrahydrophenanthrene

Chemical Property:

• Vapor Pressure: 1.27E-10mmHg at 25°C
• Boiling Point: 495.2°Cat760mmHg
• Flash Point: 253.3°C
• PSA: 52.99000
• Density: 1.372g/cm³
• LogP: 2.30440

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7,8-dihydroxy-5,6-epoxy-1,4-dimethyl-5,6,7,8-tetrahydrophenanthrene

There total 13 articles about 7,8-dihydroxy-5,6-epoxy-1,4-dimethyl-5,6,7,8-tetrahydrophenanthrene 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: 93.0%

(7R,7aS,10aS,11S)-11-Bromo-7-hydroxy-1,4-dimethyl-7,7a,10a,11-tetrahydro-phenanthro[2,3-d][1,3]dioxol-9-one (122033-86-7) → (1aR,2R,3S,9cS)-6,9-Dimethyl-1a,2,3,9c-tetrahydro-1-oxa-cyclopropa[c]phenanthrene-2,3-diol (122033-85-6,122089-49-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 0.333333h; Ambient temperature;

DOI:10.1021/ja00176a062

Reference yield:

2-bromo-5,8-dimethyl-1-naphthyl p-toluenesulfonate (123674-24-8) → (1aR,2R,3S,9cS)-6,9-Dimethyl-1a,2,3,9c-tetrahydro-1-oxa-cyclopropa[c]phenanthrene-2,3-diol (122033-85-6,122089-49-0)

Guidance literature:

Multi-step reaction with 6 steps

1: n-BuLi / tetrahydrofuran / 12 h / -78 - 20 °C

2: H₂ / PtO₂ / benzene; ethanol / 4 h / Ambient temperature

3: BF₃*Et₂O, EtSH / CH₂Cl₂ / 6 h / 0 °C

5: 83 percent / BBr₃ / -40 °C

6: 93 percent / 4.0 M aq. NaOH / tetrahydrofuran / 0.33 h / Ambient temperature

With sodium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; boron tribromide; ethanethiol; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; benzene;

DOI:10.1021/ja00176a062

Reference yield:

2-bromo-5,8-dimethyl-1-naphthyl p-toluenesulfonate (123674-24-8) → (1aR,2S,3R,9cS)-6,9-Dimethyl-1a,2,3,9c-tetrahydro-1-oxa-cyclopropa[c]phenanthrene-2,3-diol (122033-85-6,122089-49-0)

Guidance literature:

Multi-step reaction with 7 steps

1: n-BuLi / tetrahydrofuran / 12 h / -78 - 20 °C

2: H₂ / PtO₂ / benzene; ethanol / 4 h / Ambient temperature

3: BF₃*Et₂O, EtSH / CH₂Cl₂ / 6 h / 0 °C

5: 83 percent / BBr₃ / -40 °C

6: 81 percent / Cr(ClO₄)2

7: 1.) N-bromoacetamide (NBA), H₂O, 2.) KO-t-Bu / 1.) THF, 0 deg C, 3 h, 2.) O deg C, 1 h

With n-butyllithium; chromium(II) perchlorate; boron trifluoride diethyl etherate; potassium tert-butylate; water; hydrogen; boron tribromide; ethanethiol; N-bromoacetamide; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; benzene;

DOI:10.1021/ja00176a062

upstream raw materials:

(7R,7aS,10aS,11S)-11-Bromo-7-hydroxy-1,4-dimethyl-7,7a,10a,11-tetrahydro-phenanthro[2,3-d][1,3]dioxol-9-one

C₁₆H₁₆O₃

C₁₇H₁₄O₄

2-bromo-5,8-dimethyl-1-naphthyl p-toluenesulfonate