Triptoquinone A

Base Information

• Chemical Name: Triptoquinone A
• CAS No.: 142950-86-5
• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.408
• DSSTox Substance ID: DTXSID80162236
• Nikkaji Number: J567.353D
• Wikidata: Q83030838
• Metabolomics Workbench ID: 133216
• ChEMBL ID: CHEMBL3797679
• Mol file: 142950-86-5.mol

Synonyms:triptoquinone A

Chemical Property of Triptoquinone A

Chemical Property:

• Vapor Pressure: 6.3E-11mmHg at 25°C
• Boiling Point: 489.6°Cat760mmHg
• Flash Point: 264°C
• PSA: 71.44000
• Density: 1.21g/cm³
• LogP: 3.62840
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 328.16745924
• Heavy Atom Count: 24
• Complexity: 748

Purity/Quality:

99% ^*data from raw suppliers

TriptoquinoneA 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(CCC2(C1CCC3=C2C(=O)C=C(C3=O)C(C)C)C)C(=O)O
• Isomeric SMILES: CC1=C(CC[C@]2([C@H]1CCC3=C2C(=O)C=C(C3=O)C(C)C)C)C(=O)O

Technology Process of Triptoquinone A

There total 47 articles about Triptoquinone A 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: 83.0%

(4aS*,10aR*)-5,8-Dimethoxy-1,4a-dimethyl-7-isopropyl-3,4,4a,9,10,10a-hexahydrophenanthrene-2-carboxylic acid (146356-68-5) → (+/-)-triptoquinone A (137758-96-4,142950-86-5,146389-40-4)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; for 0.583333h; Ambient temperature;

DOI:10.1021/jo00081a021

Reference yield:

2-isopropyl-6-methoxy-1-naphthol (62416-09-5) → (+/-)-triptoquinone A (137758-96-4,142950-86-5,146389-40-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 85 percent / NBS / dimethylformamide / 3 h / 0 °C

2: 96 percent / 1 N KOH / 0.75 h / 0 °C

3: 92 percent / CuI, NaOMe / dimethylformamide / 2 h / Heating

4: 1.) Na, EtOH, 2.) oxalic acid / 1.) reflux, 30 min, 2.) H₂O, MeOH, reflux, 21 h

5: 1.) pyrrolidine, molecular sieves 3 Angstroem / 1.) C₆H₆, r.t., 4.5 h, 2.) dioxane, reflux, 45 h

6: 60 percent / KOH / methanol; H₂O / 1.) -20 deg C, 1 h, 2.) r.t., 15 h

7: 1.) Li, NH₃, t-BuOH, 2.) Et₃N / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 30 min

8: 1.) MeLi / 1.) THF, Et₂O, r.t, 30 min, 2.) THF, 0 deg C, 9.5 h

9: 54 percent / n-Bu₃N, DPPF / Pd(OAc)2 / dimethylformamide / 3.5 h / 95 °C

10: 83 percent / CAN / H₂O; acetonitrile / 0.58 h / Ambient temperature

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; potassium hydroxide; N-Bromosuccinimide; copper(l) iodide; ammonium cerium(IV) nitrate; tributyl-amine; ethanol; 3 A molecular sieve; ammonia; methyllithium; sodium methylate; sodium; oxalic acid; lithium; triethylamine; tert-butyl alcohol; palladium diacetate; In methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00081a021

Reference yield:

4-Bromo-2-isopropyl-6-methoxy-1-naphthol (146356-60-7) → (+/-)-triptoquinone A (137758-96-4,142950-86-5,146389-40-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / 1 N KOH / 0.75 h / 0 °C

2: 92 percent / CuI, NaOMe / dimethylformamide / 2 h / Heating

3: 1.) Na, EtOH, 2.) oxalic acid / 1.) reflux, 30 min, 2.) H₂O, MeOH, reflux, 21 h

4: 1.) pyrrolidine, molecular sieves 3 Angstroem / 1.) C₆H₆, r.t., 4.5 h, 2.) dioxane, reflux, 45 h

5: 60 percent / KOH / methanol; H₂O / 1.) -20 deg C, 1 h, 2.) r.t., 15 h

6: 1.) Li, NH₃, t-BuOH, 2.) Et₃N / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 30 min

7: 1.) MeLi / 1.) THF, Et₂O, r.t, 30 min, 2.) THF, 0 deg C, 9.5 h

8: 54 percent / n-Bu₃N, DPPF / Pd(OAc)2 / dimethylformamide / 3.5 h / 95 °C

9: 83 percent / CAN / H₂O; acetonitrile / 0.58 h / Ambient temperature

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; potassium hydroxide; copper(l) iodide; ammonium cerium(IV) nitrate; tributyl-amine; ethanol; 3 A molecular sieve; ammonia; methyllithium; sodium methylate; sodium; oxalic acid; lithium; triethylamine; tert-butyl alcohol; palladium diacetate; In methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00081a021

upstream raw materials:

(+)-(4aS,10aR)-5,8-Dimethoxy-1,4a-dimethyl-7-isopropyl-3,4,4a,9,10,10a-hexahydrophenanthrene-2-carboxylic acid

4-bromo-2-isopropyl-phenol

2-isopropyl-6-methoxy-1-naphthol

4-Bromo-2-isopropyl-6-methoxy-1-naphthol

Refernces

• 1、 Shishido, Kozo,Goto, Kiyoto,Miyoshi, Shizuka,Takaishi, Yoshihisa,Shibuya, Masayuki. "TOTAL SYNTHESIS OF (+/-)-TRIPTOQUINONE A". . p. 339 - 340. Retrieved 2007/10/02.