(4aR)-7β-Ethenyl-4,4a,4bβ,5,6,7,10,10aβ-octahydro-1,1,4aα,7-tetramethyl-2,9(1H,3H)-phenanthrenedione

Base Information

• Chemical Name: (4aR)-7β-Ethenyl-4,4a,4bβ,5,6,7,10,10aβ-octahydro-1,1,4aα,7-tetramethyl-2,9(1H,3H)-phenanthrenedione
• CAS No.: 90044-20-5
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.441
• Mol file: 90044-20-5.mol

Synonyms:(4aR,4bS,7S,10aS)-1,1,4a,7-Tetramethyl-7-vinyl-4,4a,4b,5,6,7,10,10a-octahydro-1H,3H-phenanthrene-2,9-dione;Oryzalexin C;

Chemical Property of (4aR)-7β-Ethenyl-4,4a,4bβ,5,6,7,10,10aβ-octahydro-1,1,4aα,7-tetramethyl-2,9(1H,3H)-phenanthrenedione

Chemical Property:

• Vapor Pressure: 4.66E-07mmHg at 25°C
• Melting Point: 147 - 148 °C (hexane)
• Boiling Point: 413.8°C at 760 mmHg
• Flash Point: 154.8°C
• PSA: 34.14000
• Density: 1.05g/cm³
• LogP: 4.49950

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR)-7β-Ethenyl-4,4a,4bβ,5,6,7,10,10aβ-octahydro-1,1,4aα,7-tetramethyl-2,9(1H,3H)-phenanthrenedione

There total 14 articles about (4aR)-7β-Ethenyl-4,4a,4bβ,5,6,7,10,10aβ-octahydro-1,1,4aα,7-tetramethyl-2,9(1H,3H)-phenanthrenedione 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:

(+)-oryzalexin-A (85394-31-6) → oryzalexin C (90044-20-5)

Guidance literature:

With chromium(VI) oxide; In acetone; at 0 - 5 ℃; for 0.0833333h; Yield given;

DOI:10.1016/S0040-4020(01)91369-9

Reference yield:

(+/-) - 13-butylthiomethylene-3α-hydroxy-4α,4β,10α-trimethyl-14-oxo-5β,8α,9β-perhydrophenanthrene (105996-89-2) → oryzalexin C (90044-20-5)

Guidance literature:

Multi-step reaction with 12 steps

1: imidazole / dimethylformamide / 20 h / 25 - 30 °C

2: 1.)NaBH₄ 2.)CdCO₃, HgCl₂ / 1.)EtOH, THF, 2 h, 10 deg C_. 2.)EtOH, reflux, 5 min

3: t-BuOK / benzene; 2-methyl-propan-2-ol / 1 h

4: 1.)n-BuLi / 1.)Hexane, THF, 10 min, 0-5 deg C_. 2.)THF, overnight room temp.

5: aq HF / acetonitrile / 1.5 h / Ambient temperature

6: 42 percent / p-TsOH*H₂O / benzene / 1 h / Heating

7: 95 percent / aq HCl / methanol / 0.25 h / Ambient temperature

8: pyridine / Ambient temperature

9: SeO₂, H₂₀ / acetic acid; benzene / 0.03 h / 61 - 64 °C

10: DMSO, AcO₂ / Ambient temperature

11: K₂CO₃ / methanol / Ambient temperature

12: CrO₃ / acetone / 0.08 h / 0 - 5 °C

With 1H-imidazole; chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; selenium(IV) oxide; cadmium(II) carbonate; AcO₂; hydrogen fluoride; potassium tert-butylate; water; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; mercury dichloride; In pyridine; methanol; acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)91369-9

Reference yield:

Formic acid (4aR,4bS,8aR,10aR)-7-[1-butylsulfanyl-meth-(Z)-ylidene]-1,1,4a-trimethyl-8-oxo-tetradecahydro-phenanthren-2-yl ester (105996-90-5) → oryzalexin C (90044-20-5)

Guidance literature:

Multi-step reaction with 13 steps

1: KOH / methanol; H₂O

2: imidazole / dimethylformamide / 20 h / 25 - 30 °C

3: 1.)NaBH₄ 2.)CdCO₃, HgCl₂ / 1.)EtOH, THF, 2 h, 10 deg C_. 2.)EtOH, reflux, 5 min

4: t-BuOK / benzene; 2-methyl-propan-2-ol / 1 h

5: 1.)n-BuLi / 1.)Hexane, THF, 10 min, 0-5 deg C_. 2.)THF, overnight room temp.

6: aq HF / acetonitrile / 1.5 h / Ambient temperature

7: 42 percent / p-TsOH*H₂O / benzene / 1 h / Heating

8: 95 percent / aq HCl / methanol / 0.25 h / Ambient temperature

9: pyridine / Ambient temperature

10: SeO₂, H₂₀ / acetic acid; benzene / 0.03 h / 61 - 64 °C

11: DMSO, AcO₂ / Ambient temperature

12: K₂CO₃ / methanol / Ambient temperature

13: CrO₃ / acetone / 0.08 h / 0 - 5 °C

With 1H-imidazole; chromium(VI) oxide; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; selenium(IV) oxide; cadmium(II) carbonate; AcO₂; hydrogen fluoride; potassium tert-butylate; water; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; mercury dichloride; In pyridine; methanol; water; acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)91369-9

upstream raw materials:

(+)-oryzalexin-A

(+/-) - 13-butylthiomethylene-3α-hydroxy-4α,4β,10α-trimethyl-14-oxo-5β,8α,9β-perhydrophenanthrene

Formic acid (4aR,4bS,8aR,10aR)-7-[1-butylsulfanyl-meth-(Z)-ylidene]-1,1,4a-trimethyl-8-oxo-tetradecahydro-phenanthren-2-yl ester

tert-Butyl-dimethyl-((2S,4aR,4bS,10aR)-1,1,4a,7-tetramethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthren-2-yloxy)-silane

Refernces

• 1、 Kono, Yoshiki,Takeuchi, Setsuo,Kodama, Osamu,Akatsuka, Tadami. "Absolute Configuration of Oryzalexyn A and Structures of Its Related Phytoalexins Isolated from Rice Blast Leaves Infected with Pyricularia oryzae". . p. 253 - 256. Retrieved 2007/10/02.