605-89-0

Basic information

• Product Name: 1,5-naphthylene di(acetate)
• Synonyms: 1,5-naphthylene di(acetate);1,5-Diacetoxynaphthalene;1,5-Naphthalenediol diacetate;Diacetic acid=1,5-naphthylene ester;Naphthalene-1,5-diol diacetate;(5-acetyloxynaphthalen-1-yl) acetate;(5-acetyloxynaphthalen-1-yl) ethanoate;acetic acid (5-acetoxy-1-naphthyl) ester
• CAS NO: 605-89-0
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24268
• EINECS: 210-098-9
• Mol File: 605-89-0.mol

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 386.5°C at 760 mmHg
• Flash Point: 196.2°C
• Appearance: /
• Density: 1.228g/cm³
• Vapor Pressure: 3.54E-06mmHg at 25°C
• Refractive Index: 1.586
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 1,5-naphthylene di(acetate)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-naphthylene di(acetate)(605-89-0)
• EPA Substance Registry System: 1,5-naphthylene di(acetate)(605-89-0)

Safety Data

• Hazardous Substances Data: 605-89-0(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1,5-Naphthylene di(acetate) is used as an intermediate in the synthesis of Plumbagin-d3 (P627002) for its potential application in cancer treatment. Plumbagin-d3 is a labeled version of Plumbagin (P627000), which is known to induce apoptosis in cancer cells, thereby exhibiting anti-cancer properties.
2. Used in Research and Development:
1,5-Naphthylene di(acetate) is utilized in the development of new compounds and drugs, particularly in the field of cancer research. Its role as an intermediate in the synthesis of Plumbagin-d3 highlights its importance in creating potential therapeutic agents.
3. Used in Chemical Synthesis:
1,5-Naphthylene di(acetate) is employed as a building block in the synthesis of various organic compounds, contributing to the development of new materials and products in the chemical industry.
4. Used in Biochemical Research:
1,5-Naphthylene di(acetate) is also used in biochemical research to study its interactions with different biological molecules, which could lead to the discovery of new applications in the fields of medicine and biotechnology.

InChI:InChI=1/C14H12O4/c1-9(15)17-13-7-3-6-12-11(13)5-4-8-14(12)18-10(2)16/h3-8H,1-2H3

Upstream product

• 83-56-7 1,5-dihydroxynaphthalene 
• 108-24-7 acetic anhydride 
• 25543-68-4 1,5-dihydroxy-2,6-naphthalenedicarboxylic acid 
• 127-09-3 sodium acetate 
• 108-05-4 vinyl acetate 
• 91-20-3 naphthalene 
• 75-36-5 acetyl chloride 

Downstream Products

• 5196-28-1 juglone acetate 
• 77189-69-6 5-acetoxy-2-bromo-1,4-naphthoquinone 
• 83-56-7 1,5-dihydroxynaphthalene 
• 94807-85-9 5-hydroxynaphthalen-1-yl acetate 
• 109972-84-1 1-Benzyloxy-5-hydroxynaphthalene 
• 221461-63-8 acetic acid 5-benzyloxy-naphthalen-1-yl ester 
• 1262052-77-6 2-(2-(1,3-dioxan-2-yl)-6-(methoxymethoxy)-4-methylphenyl)-5-hydroxynaphthalene-1,4-dione 
• 1262052-80-1 3-hydroxy-2-(5-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-5-methylbenzaldehyde 
• 4923-55-1 2-Hydroxyjuglon 
• 68963-23-5 1-hydroxy-7-methylanthracene-9,10-dione 

Relevant articles and documents

Synthesis of Barleriaquinones-I & II

Synthesis of two naturally occurring anthraquinones, Barleriaquinone-I (BQ-I) and Barleriaquinone-II (BQ-II) is achieved from commercially available naphthalene-1,5-diol. The anthraquinone core is constructed by utilizing simultaneous Heck and cross coupling reaction as the key step.

Organocatalytic asymmetric addition of naphthols and electron-rich phenols to isatin-derived ketimines: Highly enantioselective construction of tetrasubstituted stereocenters

A quinine-derived thiourea organocatalyst promoted the highly enantioselective addition of naphthols and activated phenols to ketimines derived from isatins. The reaction afforded chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields (up to 99%) with excellent enantioselectivity (up to 99%ee). To the best of our knowledge, this transformation is the first highly enantioselective addition of naphthols to ketimines.

Synthesis, molecular docking, and biological activity of thioether derived from juglone in preclinical models of chronic myeloid leukemia

In this work, 16 new thio-1,4-naphthoquinones were synthesized, and their antiproliferative effects against tumor cell lines SK-MEL-19, AGP-01, ACP-02, HL-60, K-562, K-562-Lucena-1, FEPS, and non-neoplastic human fibroblast MRC-5, were examined. The compounds were selective active against leukemia cell lines. Based on the screening results for cytotoxic activity, naphthoquinone 11a showed higher cytotoxicity on the chemoresistant leukemia (FEPS) cell line when compared to the chemosensitive (K-562) cell line. Moreover, naphthoquinone 11a presented excellent ADME/T and did not violate Lipinski's rule of five, indicating good oral absorption. Target prediction revealed DNA topoisomerase I (TOP1) as a possible target of 11a. The molecular docking prediction showed an ? 11.94 kcal/mol binding affinity interaction of 11a with TOP1, involving three hydrogen bonds to ARG364, A113, and G11 from the active site of the enzyme. In addition, naphthoquinone 11a significantly suppressed the expression of the TOP1 gene in K-562 and FEPS leukemia cell lines. The naphthoquinone 11a induced significant changes in cell morphology, demonstrating cell and nuclear shrinkage, blebbing formation as well and fragmentation of the cell into apoptotic bodies. Thus, 11a could be a drug that leads to a new set of TOP1 major inhibitors. In summary, the present study showed a cytotoxic effect of 11a against chemoresistant and chemosensitive leukemia cell lines with TOP1 as a possible target.

Naphthoquinone derivative or a salt thereof as an active ingredient and horticultural fungicide containing (by machine translation)

[A] a naphthoquinone derivative or salt thereof, or a salt thereof as an active ingredient horticultural fungicide containing said derivative, and use thereof. [Solution] the ingredient, represented by the following formula. [In the formula, R1 And R2 Is, for example, are each independently a hydrogen atom, a halogen, amino, substituted C1 - C6 The alkylcarbonyloxy groups such as shown, however, R1 And R2 Is, not simultaneously hydrogen atoms, R3 Is, for example, C1 - C6 Alkyl, C3 - C8 Cycloalkyl, C1 - C6 Alkoxy groups, R5 R6 N - shown as, R4 Is, a hydrogen atom or a halogen atom, here, R5 And R6 The, each independently hydrogen atom or C1 - C6 The alkyl groups, R5 And R6 The, the nitrogen atom to which they are attached together, may form a hetero ring, however, R5 And R6 The, are not simultaneously hydrogen atoms. ][Drawing] no (by machine translation)

Na 2 CO 3-Catalyzed O-Acylation of Phenols for the Synthesis of Aryl Carboxylates with Use of Alkenyl Carboxylates

Inorganic base-catalyzed O-acylation of phenol and its derivatives has been developed. The procedure provides an efficient catalysis system for the preparation of aryl carboxylates with alkenyl carboxylates as acyl reagents. The reaction proceeded smoothly by using ?-Na 2 CO 3 as the catalyst in MeCN to produce the corresponding aryl carboxylates in good to excellent yields.

Novel methodology for the synthesis of the benzo[b]phenanthridine and 6H-dibenzo[c,h]chromen-6-one skeletons. Reactions of 2-naphthylbenzylamines and 2-naphthylbenzyl alcohols

Novel syntheses of both the benzo[b]phenanthridine and the 6H-dibenzo[c,h]chromen-6-one motif are described. Reaction of (2-(3-bromo-1,4-dimethoxynaphthalen-2-yl)phenyl)methanamine with PIFA afforded benzo[b]phenanthridine-7,12-dione, while the related nonbrominated precursor, (2-(1,4,5-trimethoxynaphthalen-2-yl)phenyl)methanamine on treatment with PIFA, furnished the ortho-quinone 1-methoxybenzo[c]phenanthridine-11,12-dione. Unexpectedly, treatment of related oxygen analogs such as (2-(1,4-dimethoxynaphthalen-2-yl)phenyl)methanol with NBS under an O2atmosphere, afforded a chromenone, 12-methoxy-6H-dibenzo[c,h]chromen-6-one.

Toward Naphthocyclinones: Doubly Connected Octaketide Dimers with a Bicyclo[3.2.1]octadienone Core by Thiolate-Mediated Cyclization

A viable method is reported for the synthesis of the bicyclo[3.2.1]octadienone scaffold in naturally occurring octaketide dimers. The procedure employs a reductive cyclization reaction mediated by an unusual ethanedithiol monosodium salt. Doubling up: A viable method for the construction of bicyclo[3.2.1]octadienone scaffolds has been developed, involving the reductive cyclization of dimeric naphthoquinone monoacetal mediated by the monosodium salt of 1,2-ethanedithiol. Bicyclo[3.2.1]octadienones may serve as key core units in the synthesis of biologically relevant naphthocyclinones.

The first vinyl acetate mediated organocatalytic transesterification of phenols: A step towards sustainability

The present report outlines our efforts toward a simple yet elegant protocol for O-acylation of a wide variety of phenols. This highly enabling and solventless method relies on vinyl acetate as an innocuous acyl donor and DABCO as an organocatalyst. Operational simplicity, excellent yields, higher and faster conversion rates without excess reagents, a simple workup and essentially no need of columns are some of the salient features of the reported protocol.

Synthesis and cytotoxic activity of a small naphthoquinone library: First synthesis of juglonbutin

A synthetic protocol has been designed to synthesize grecoketidone (2k), 5-hydroxylapachol (2g), and the recently discovered natural products juglonbutin (2o) and its derivatives, leading to a small library of different 1,4-naphthoquinones with the intention of finding new active compounds. Within our collection, 2-O-alkylated naphthoquinones with an ester functionality in the side-chain and a free OH group at C-5 showed the best activities. Compounds 2f, 2m, and 2n showed GI50 values against 12 tumor cell lines in the lower micromolar range and juglonbutin (2o) showed remarkably efficient inhibition of the glycogen synthase kinase 3β with an IC50 value of 2.03 μM. Furthermore, studies on the mode of action of the most active cytotoxic compounds have been carried out. To the best of our knowledge, this is the first report on the synthesis of juglonbutin (2o) and its biological activity. Copyright

Total synthesis of jadomycins B, S, T, and ILEVS1080

Sweetening up jadomycin A: The first total synthesis of jadomycins B, S, T, and ILEVS1080 has been achieved, featuring construction of the unique 8H-benz[b]oxazolo[3,3-f]phenanthridine skeleton by biomimetic condensation of a quinone aldehyde with amino acid sodium salts and elaboration of the glycosides by Mitsunobu condensation (see figure). Copyright