13861-97-7

Basic information

• Product Name: DIHYDRO-4,4-DIMETHYL-2(3H)-FURANONE
• Synonyms: DIHYDRO-4,4-DIMETHYL-2(3H)-FURANONE;4,4-Dimethyl-4,5-dihydrofuran-2(3H)-one;4,4-Dimethyltetrahydrofuran-2-one;4,5-Dihydro-4,4-dimethyl-2(3H)-furanone;2(3H)-Furanone, dihydro-4,4-diMethyl-;4,4-diMethyldihydrofuran-2(3h)-one;4,4-dimethyldihydro-2(3H)-furanone
• CAS NO: 13861-97-7
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• Mol File: 13861-97-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 55-57 °C
• Boiling Point: 191.5°C at 760 mmHg
• Flash Point: 66.9°C
• Appearance: /
• Density: 0.995g/cm³
• Vapor Pressure: 0.513mmHg at 25°C
• Refractive Index: 1.428
• CAS DataBase Reference: DIHYDRO-4,4-DIMETHYL-2(3H)-FURANONE(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDRO-4,4-DIMETHYL-2(3H)-FURANONE(13861-97-7)
• EPA Substance Registry System: DIHYDRO-4,4-DIMETHYL-2(3H)-FURANONE(13861-97-7)

Safety Data

• Hazardous Substances Data: 13861-97-7(Hazardous Substances Data)

Usage

Description

DIHYDRO-4,4-DIMETHYL-2(3H)-FURANONE is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique chemical structure, which contributes to its potential applications in the medical field.

Uses

Used in Pharmaceutical Industry:
DIHYDRO-4,4-DIMETHYL-2(3H)-FURANONE is used as a key intermediate for the preparation of pyridazinones, which are PARP7 inhibitors. These inhibitors are valuable in the treatment of cancer, as they target and inhibit the activity of PARP7, a protein involved in DNA repair and cell survival. By inhibiting PARP7, pyridazinones can potentially enhance the effectiveness of cancer therapies and improve patient outcomes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2034, 1986 DOI: 10.1021/jo00361a018Synthetic Communications, 10, p. 881, 1980 DOI: 10.1080/00397918008062773Tetrahedron Letters, 24, p. 2677, 1983 DOI: 10.1016/S0040-4039(00)87975-7

InChI:InChI=1/C6H10O2/c1-6(2)3-5(7)8-4-6/h3-4H2,1-2H3

Upstream product

• 50639-30-0 isobutyl 2-diazoacetate 
• 10303-64-7 2-hydroxy-4-methylpentanoic acid 
• 773837-37-9 sodium cyanide 
• 1755-97-1 5,5-dimethyl-1,3,2-dioxathiane-2,2-dioxide 
• 1003-85-6 5.5-dimethyl-1,3,2-dioxathiane-2-oxide 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 599-04-2 (R)-Pantolacton 
• 103804-80-4 3,3-dimethyl-4-hydroxy butyronitrile 
• 250738-85-3 3-(2-bromo-1-ethoxy-ethoxy)-2-methyl-propene 
• 5497-67-6 2,2-dimethyl-4-pentenal 
• 3420-42-6 2,2-dimethylpent-4-en-1-ol 
• 102536-88-9 4,4-Dimethyl-tetrahydro-furan-2-ol 
• 77903-45-8 methyl 2,2-dimethyl-3-(trimethylsiloxy)-1-cyclopropanecarboxylate 
• 32812-23-0 2,2-dimethylbutane-1,4-diol 

Downstream Products

• 1414356-81-2 C₂₆H₄₀N₄O₂ 
• 1034144-16-5 C₁₃H₁₇ClO₄ 
• 130838-69-6 6-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-cyclohex-2-enone 
• 599-04-2 (R)-Pantolacton 
• 79-50-5 (S)-pantolactone 
• 597-43-3 2,2-dimethylsuccinic acid 

Relevant articles and documents

2-Siloxy-Substituted Methyl Cyclopropanecarboxylates as Building Blocks in Synthesis: Efficient One-Pot Conversion to γ-Butyrolactones

A high-yield one-pot transformation to the easily available 2-siloxy-substituted methyl cyclopropanecarboxylates 3 to γ-butyrolactones 5 is described.According to the regioselective preparation of 3, isomeric lactones 5 can be synthesized without problems.Modified procedures delivering α-deuterated or side-chain functionalized lactones are disclosed.

SELECTIVE OXIDATION OF A PRIMARY HYDROXYL IN THE PRESENCE OF SECONDARY ONE

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Structural and stereochemical requirements of the spiroketal group of hippuristanol for antiproliferative activity

Hippuristanol is a natural product that has recently been shown to inhibit eukaryotic translation initiation and tumor cell proliferation. To investigate the structure and activity relationship of hippuristanol, we synthesized a series of analogs by expan

Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds

An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp3)-H bonds through radical 1,5-hydrogen abstraction. The γ-bromoamides formed are subsequently converted to γ-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp3-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of γ-lactones into complex carbon frameworks.

Diverting non-haem iron catalysed aliphatic C-H hydroxylations towards desaturations

Carboxylate-ligated, non-haem iron enzymes demonstrate the capacity for catalysing such remarkable processes as hydroxylations, chlorinations and desaturations of inert, aliphatic C-H bonds. A key to functional diversity is the enzymes' ability to divert fleeting radicals towards different types of functionalization using active site and/or substrate modifications. We report that a non-haem iron hydroxylase catalyst [Fe(PDP)] can also be diverted to catalytic, mixed hydroxylase/desaturase activity with aliphatic C-H bonds. Using a taxane-based radical trap that rearranges under Fe(PDP) oxidation to furnish a nortaxane skeleton, we provide the first direct evidence for a substrate radical using this class of stereoretentive hydroxylation catalysts. Hydroxylation and desaturation proceed by means of a short-lived radical that diverges in a substrate-dependent manner in the presence of carboxylic acids. The novel biomimetic reactivity displayed by this small molecule catalyst is harnessed to diversify natural product derivatives as well as interrogate their biosynthetic pathways.