xyloidone

Base Information

• Chemical Name: xyloidone
• CAS No.: 15297-92-4
• Molecular Formula: C15H12O3
• Molecular Weight: 240.258
• Hs Code.: 2914399090
• Mol file: 15297-92-4.mol

Synonyms:Dehydro-a-lapachol;Dehydro-a-lapachone;Dehydro-a-lapacone;Dehydrolapachone;NSC106453;NSC 629748;Xiloidone;Xyloidone;a-Lapachone, dehydro-;

Chemical Property of xyloidone

Chemical Property:

• Vapor Pressure: 1.87E-06mmHg at 25°C
• Melting Point: 156 °C
• Refractive Index: 1.62
• Boiling Point: 395.2 °C at 760 mmHg
• Flash Point: 177 °C
• PSA: 43.37000
• Density: 1.28 g/cm³
• LogP: 2.68470
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

Q 99 2,2-DIMETHYL-2H-NAPHTHO(2,3-B)PYRAN-5,10-DIONE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of xyloidone

There total 36 articles about xyloidone 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: 98.1%

tert-butyl 2-methylbut-3-en-2-yl carbonate (861216-48-0) + 2-hydroxynaphtho-1,4-quinone (83-72-7) → 2,2-dimethyl-2H-benzo[g]chromene-5,10-dione (15297-92-4)

Guidance literature:

With cerium(III) chloride; bis(acetylacetonato)palladium(II); potassium acetate; copper(II) bis(trifluoromethanesulfonate); acetic acid; 1-hexyl-3-methylimidazol-1-ium chloride; at 20 ℃; for 2.5h; Reagent/catalyst;

Reference yield: 91.0%

2-hydroxynaphtho-1,4-quinone (83-72-7) + 3,3-dimethyl acrylaldehyde (107-86-8) → 2,2-dimethyl-2H-benzo[g]chromene-5,10-dione (15297-92-4)

Guidance literature:

In neat (no solvent); at 20 - 120 ℃; for 12h; Microwave irradiation; Green chemistry;

DOI:10.5012/bkcs.2013.34.10.2963

Reference yield: 89.0%

3-chloro-3-methylbut-1-yne (1111-97-3) + 2-hydroxynaphtho-1,4-quinone (83-72-7) → 2,2-dimethyl-2H-benzo[g]chromene-5,10-dione (15297-92-4)

Guidance literature:

With iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride; In acetonitrile; for 24h; Concentration; Reflux;

DOI:10.1002/jhet.2087

upstream raw materials:

1-methyl-4-nitrosobenzene

3'-bromo-β-lapachone

Lapachol

α-lapachone diacetate

Downstream raw materials:

β,β-di-(bromomethyl)pyrano-1,4-naphthoquinone

3,4-dibromodehydro-α-lapachone

3,4-dehydro-β-lapachone

3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione

Refernces

• 1、 Da Rocha, David R.,Mota, Kelly,Da Silva, Illana M.C.B.,Ferreira, Vitor F.,Ferreira, Sabrina B.,Da Silva, Fernando De C.. "Synthesis of fused chromene-1,4-naphthoquinones via ring-closing metathesis and Knoevenagel-electrocyclization under acid catalysis and microwave irradiation". . p. 3266 - 3270. Retrieved 2014.
• 2、 Kumar, Sanjeev,Malachowski, William P.,DuHadaway, James B.,LaLonde, Judith M.,Carroll, Patrick J.,Jaller, Daniel,Metz, Richard,Prendergast, George C.,Muller, Alexander J.. "Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors". . p. 1706 - 1718. Retrieved 2008.
• 3、 Bian, Jinlei,Qian, Xue,Wang, Nan,Mu, Tong,Li, Xiang,Sun, Haopeng,Zhang, Lianshan,You, Qidong,Zhang, Xiaojin. "Palladium(II)-Catalyzed C-H Bond Activation/C-C Coupling/Intramolecular Tsuji-Trost Reaction Cascade: Facile Access to 2 H -Pyranonaphthoquinones". . p. 3410 - 3413. Retrieved 2015.
• 4、 Lee, Yong Rok,Choi, Jung Hyun,Trinh, Dinh Thi Lan,Kim, Nam Woo. "A concise route for the synthesis of pyranonaphthoquinone derivatives". . p. 3026 - 3034. Retrieved 2005.
• 5、 -. "Catalyzed synthesis method of dehydrogenated alpha-lapachol". Paragraph 0026; 0027; 0028; 0029. . Retrieved 2017/01/19.
• 6、 Da Silva Júnior, Paulo Eliandro,De Araujo, Natália Maria,Da Silva Emery, Flavio. "Claisen rearrangement of hydroxynaphthoquinones: Selectivity toward naphthofuran or α-xiloidone using copper salts and iodine". . p. 518 - 521. Retrieved 2015/03/30.