.+/-.-2-Methoxy-3,8-dioxocephalotax-1-ene

Base Information

• Chemical Name: .+/-.-2-Methoxy-3,8-dioxocephalotax-1-ene
• CAS No.: 114942-83-5
• Molecular Formula: C18H17 N O5
• Molecular Weight: 327.33
• Mol file: 114942-83-5.mol

Synonyms:4H-Cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine,cephalotaxine deriv.

Chemical Property of .+/-.-2-Methoxy-3,8-dioxocephalotax-1-ene

Chemical Property:

• PSA: 65.07000
• LogP: 1.46710

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .+/-.-2-Methoxy-3,8-dioxocephalotax-1-ene

There total 33 articles about .+/-.-2-Methoxy-3,8-dioxocephalotax-1-ene 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: 97.0%

Trimethylmethoxysilane (1825-61-2) + 2,3,8-trioxocephalotaxane (114956-74-0) → 2-methoxy-3,8-dioxocephalotax-1-ene (114942-83-5)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; for 24h;

DOI:10.1021/jo00250a008

Reference yield: 43.0%

C19H23NO6 (121588-67-8) → 2-methoxy-3,8-dioxocephalotax-1-ene (114942-83-5) + C19H21NO6 (121588-68-9)

Guidance literature:

With dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; at -60 ℃;

DOI:10.1248/cpb.36.4229

Reference yield:

1-(benzo[1,3]dioxol-5-yl)-2-bromoethanone (40288-65-1) → 2-methoxy-3,8-dioxocephalotax-1-ene (114942-83-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 80 percent / 4 h / 85 °C

2: 98 percent / sodium borohydride / methanol / -18 - -15 °C

3: 82 percent / hydrogen, 70percent perchloric acid / 10percent Pd-C / acetic acid

4: 100 percent / potassium hydroxide / ethanol; H₂O

5: 75 percent / trifluoroacetic anhydride, boron trifluoride etherate / 1,2-dichloro-ethane / 4 h / Heating

6: 23 percent / sodium hydride / dimethylformamide

7: 69 percent / PdCl₂-CuCl, oxygen / dimethylformamide / 3.5 h / 75 °C / Wacker oxidation

8: 94 percent / 10percent potassium hydroxide / methanol / 1 h / Heating

9: 64 percent / hydrogene / 10percent Pd-C / acetic acid

10: 58 percent / iodosobenzene, potassium hydroxide / -8 - -5 °C

11: 10 percent / (CF₃CO)2O, DMSO / CH₂Cl₂ / -60 °C

With potassium hydroxide; sodium tetrahydroborate; perchloric acid; iodosylbenzene; boron trifluoride diethyl etherate; hydrogen; oxygen; sodium hydride; dimethyl sulfoxide; trifluoroacetic anhydride; copper(l) chloride; palladium dichloride; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.36.4229

upstream raw materials:

Trimethylmethoxysilane

2,3,8-trioxocephalotaxane

C₁₉H₂₁NO₆

C₁₉H₂₃NO₆

Downstream raw materials:

(±)-cephalotaxine

Refernces

• 1、 Yasuda,Yamamoto,Yoshida,Hanaoka. "A total synthesis of (±)-cephalotaxinamide". . p. 4229 - 4231. Retrieved 2007/10/02.