80155-95-9

Basic information

• Product Name: defucogilvocarcin V
• Synonyms: defucogilvocarcin V;8-Ethenyl-1-hydroxy-10,12-dimethoxy-6H-benzo[d]naphtho[1,2-b]pyran-6-one
• CAS NO: 80155-95-9
• Molecular Formula: C21H16 O5
• Molecular Weight: 348.35
• Mol File: 80155-95-9.mol

Chemical Properties

• Boiling Point: 620.7°C at 760 mmHg
• Flash Point: 226.7°C
• Appearance: /
• Density: 1.339g/cm³
• Vapor Pressure: 5.3E-16mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: defucogilvocarcin V(CAS DataBase Reference)
• NIST Chemistry Reference: defucogilvocarcin V(80155-95-9)
• EPA Substance Registry System: defucogilvocarcin V(80155-95-9)

Safety Data

• Hazardous Substances Data: 80155-95-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H16O5/c1-4-11-8-14-18(16(9-11)24-2)13-10-17(25-3)19-12(6-5-7-15(19)22)20(13)26-21(14)23/h4-10,22H,1H2,2-3H3

Upstream product

• 199858-21-4 N,N-diethyl O-[4-methoxy-5-isopropoxy-2-(2-methoxy-5-methoxymethoxyphenyl)]-1-naphthylcarbamate 
• 199858-25-8 1-isopropoxy-10,12-dimethoxy-8-trifluoromethanesulfonyl-6H-naphtho[1,2-b]benzo[d]pyran-6-one 
• 1257243-83-6 1-bromo-4-isopropoxy-5-methoxynaphthalene 
• 184221-86-1 4-bromo-8-methoxynaphthalen-1-ol 
• 685829-28-1 10,12-dimethoxy-1-(methoxymethoxy)-8-vinyl-6H-benzo-[d]naphtho[1,2-b]pyran-6-one 
• 1395924-05-6 10,12-dimethoxy-1-(methoxymethoxy)-6H-benzo[d]-naphtho[1,2-b]pyran-6-one-8-carbaldehyde 
• 1395924-07-8 8-(hydroxymethyl)-10,12-dimethoxy-1-(methoxymethoxy)-6H-benzo[d]naphtho[1,2-b]pyran-6-one-8-carboxylic acid 
• 1395924-06-7 10,12-dimethoxy-1-(methoxymethoxy)-6H-benzo[d]-naphtho[1,2-b]pyran-6-one-8-carboxylic acid 
• 1395924-04-5 C₂₃H₂₀O₈ 
• 1395924-02-3 1-hydroxy-4-methoxy-5-(methoxymethoxy)-2-naphthaldehyde 
• 139711-53-8 4-methoxy-5-(methoxymethoxy)-1-naphthol 
• 1395924-01-2 1-acetoxy-4-methoxy-5-(methoxymethoxy)naphthalene 
• 1395924-00-1 4-acetoxy-8-(methoxymethoxy)-1-naphthol 
• 176040-42-9 5-(methoxymethoxy)-1,4-naphthoquinone 

Relevant articles and documents

Carbene-Catalyzed Formal [5 + 5] Reaction for Coumarin Construction and Total Synthesis of Defucogilvocarcins

An N-heterocyclic carbene-catalyzed formal [5 + 5] reaction between enals and furanones that generates multisubstituted coumarins in a single step is reported. Five atoms in each of the substrates are involved in this catalytic process to form a benzene and a lactone ring. The power of the method is further demonstrated in metal-free total syntheses of several natural products (defucogilvocarcins M, E, and V) bearing coumarin as the key structural motif.

Anti-tuberculosis compound and synthesis method and application thereof

The invention relates to an anti-tuberculosis compound with a general structural formula I shown in the description. The compound shows high inhibitory activity on mycobacterium tuberculosis. The invention further relates to a synthesis method of the anti-tuberculosis compound. In the method, a chemical total synthesis route is adopted; the convergent synthesis route is applicable to chemical synthesis of compounds of similar structures and related derivatives and opens up broad development space of new anti-tuberculosis drugs.

An inverse electron demand Diels-Alder-based total synthesis of defucogilvocarcin V and some C-8 analogues

A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.

Combined directed remote metalation-transition metal catalyzed cross coupling strategies: The total synthesis of the aglycones of the gilvocarcins V, M, and E and arnottin I

(Chemical Equation Presented) A key directed remote metalation (DreM)-carbamoyl migration strategy was applied in an efficient synthesis of the naturally occurring 6H-naphtho[1,2-b]benzopyran-6-one defucogilvocarcin V (1a, Scheme 11). The required biarylcarbamate 33d was best prepared by a high yielding Suzuki coupling reaction of 31a with the differentially protected trioxygenated naphthalene coupling partner 32d which was synthesized using a selective acylation of a juglone derivative. In the late stages of the synthesis, the triflate 39 served as the common intermediate to install the required C-8 vinyl group of 1a (Stille coupling) as well as the required substituents for the preparation of defucogilvocarcins M (1b) and E (1c). A variety of protecting group strategies were investigated and provided insight into which groups are preferred for the DreM-carbamoyl migration process. The strategic lessons learned from this total synthesis were applied in the successful total synthesis of the structurally similar natural product arnottin I (2).

Combined directed metalation-cross coupling strategies. Total synthesis of the aglycones of gilvocarcin V, M and E

Using the versatile Directed ortho and remote Metalation protocols linked with Suzuki-Miyaura cross coupling, efficient syntheses of defucogilvocarcin V, M, and E, 2-4 have been achieved.

On the Photobiology of the Gilvocarcins. Total Synthesis of Defucogilvocarcin V and a Related Photoactive Vinyl Phenol

Defucogilvocarcin V (4a) and the related vinyl phenol 5a are important for the study of the photonicking of DNA by gilvocarcin antibiotics such as 1.They have been synthesized from a common precursor, lactone 6a, which contains the complete carbon framewo

Total synthesis of the ravidomycin aglycone (defucogilvocarcin V)

The synthesis of 1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benzonaphtho-pyran-6-one 7, starting from vanillin and 1,5-dihydroxynaphthalene is described.This compound is the aglycone of the antitumor antibiotic ravidomycin and is identical with the recently reported antimicrobial agent, defucogilcocarcin V.