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(R)-4-vinyldihydrofuran-2(3H)-one is a chemical compound with the molecular formula C6H8O2, belonging to the furan derivative family. It features a stereocenter, resulting in two enantiomers, (R)and (S-) forms, which may exhibit distinct biological activities. Characterized by a unique odor, (R)-4-vinyldihydrofuran-2(3H)-one is also valued for its low reactivity and stability, making it an ideal building block in organic synthesis for pharmaceuticals, agrochemicals, and fragrances.

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  • 121959-61-3 Structure
  • Basic information

    1. Product Name: (R)-4-vinyldihydrofuran-2(3H)-one
    2. Synonyms: (R)-4-vinyldihydrofuran-2(3H)-one
    3. CAS NO:121959-61-3
    4. Molecular Formula: C6H8O2
    5. Molecular Weight: 112.12652
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 121959-61-3.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 209°C at 760 mmHg
    3. Flash Point: 76.3°C
    4. Appearance: /
    5. Density: 1.154g/cm3
    6. Vapor Pressure: 0.207mmHg at 25°C
    7. Refractive Index: 1.55
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. CAS DataBase Reference: (R)-4-vinyldihydrofuran-2(3H)-one(CAS DataBase Reference)
    11. NIST Chemistry Reference: (R)-4-vinyldihydrofuran-2(3H)-one(121959-61-3)
    12. EPA Substance Registry System: (R)-4-vinyldihydrofuran-2(3H)-one(121959-61-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 121959-61-3(Hazardous Substances Data)

121959-61-3 Usage

Uses

Used in Pharmaceutical Industry:
(R)-4-vinyldihydrofuran-2(3H)-one is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique structural features and potential biological activities. Its presence in the molecular structure can contribute to the development of new drugs with specific therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-4-vinyldihydrofuran-2(3H)-one is utilized as a building block for the creation of novel agrochemicals. Its chemical properties allow for the development of compounds with targeted actions against pests or as effective plant growth regulators.
Used in Fragrance Industry:
(R)-4-vinyldihydrofuran-2(3H)-one is employed as a fragrance ingredient, capitalizing on its distinctive odor. It can be incorporated into perfumes, colognes, and other scented products to provide unique and appealing scents.
Used in Flavoring Industry:
(R)-4-vinyldihydrofuran-2(3H)-one is used as a flavoring agent in food products, enhancing taste profiles and contributing to the overall sensory experience of consumables.
Used in Manufacturing Industry:
(R)-4-vinyldihydrofuran-2(3H)-one's low reactivity and stability make it suitable for various chemical reactions and applications in the manufacturing industry, where it can be used to produce a range of chemical products and materials.

Check Digit Verification of cas no

The CAS Registry Mumber 121959-61-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,1,9,5 and 9 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 121959-61:
(8*1)+(7*2)+(6*1)+(5*9)+(4*5)+(3*9)+(2*6)+(1*1)=133
133 % 10 = 3
So 121959-61-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O2/c1-2-5-3-6(7)8-4-5/h2,5H,1,3-4H2/t5-/m0/s1

121959-61-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (4R)-4-ethenyloxolan-2-one

1.2 Other means of identification

Product number -
Other names (R)-4-Vinyldihydrofuran-2(3H)-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:121959-61-3 SDS

121959-61-3Relevant articles and documents

Insulin-like growth factor-1 receptor tyrosine kinase inhibitor and uses thereof

-

Paragraph 0062; 0065-0067, (2020/01/25)

The invention discloses a class of compounds capable of being used as an insulin-like growth factor-1 receptor tyrosine kinase inhibitor, and a preparation method thereof, a pharmaceutical compositioncontaining the compound, and applications of the pharma

Novel small molecule inhibitor of insulin-like growth factor-1 receptor and application of novel small molecule inhibitor

-

Paragraph 0046-0049, (2021/01/04)

The invention provides a novel small-molecule inhibitor of an insulin-like growth factor 1 receptor and application of the novel small-molecule inhibitor. The novel small-molecule inhibitor is a derivative of picropodophyllotoxin; fluorine atoms are used for replacing hydrogen atoms at two positions of the left side of picropodophyllotoxin, so that the capacity of molecules penetrating through a blood-brain barrier is improved; meanwhile, deuterium atoms are used for replacing hydrogen atoms, so that the half-life period of the molecules in an organism can be effectively prolonged. The small-molecule inhibitor can be used for preparing drugs for preventing and treating cancers. Compared with picropodophyllotoxin in the clinical test stage at present, the small-molecule inhibitor has higherblood-brain barrier permeability and longer in-vivo half-life while maintaining the action mechanism and biochemical characteristics of picropodophyllotoxin. When used alone, the small-molecule inhibitor can effectively inhibit proliferation and brain metastasis of various tumors, and can be synergistically combined with other anti-cancer drugs, so that proliferation of tumor cells is efficientlyinhibited, and the lifetime is remarkably prolonged.

Improved Synthesis of Racemate and Enantiomers of Taniguchi Lactone and Conversion of Their C-C Double Bonds into Triple Bonds

Malová Kri?ková, Petra,Lindner, Wolfgang,Hammerschmidt, Friedrich

, p. 651 - 657 (2017/11/15)

cis -2-Butene-1,4-diol was heated with triethyl orthoacetate and p -hydroquinone as catalyst at 170 °C to give racemic Taniguchi lactone. It was converted into diastereomeric amides with (S)-1-phenylethylamine for stereoisomer resolution. The double bonds

METHOD FOR PRODUCING LACTONE COMPOUND

-

Paragraph 0033; 0035, (2019/01/04)

PROBLEM TO BE SOLVED: To provide a method that makes it possible to efficiently produce a lactone compound in a short process from a raw material that is inexpensive and easily available. SOLUTION: The present invention provides a method for producing a lactone compound by the reaction between a diester compound and orthocarboxylate, in the presence of a Lewis acid catalyst; preferably, the Lewis acid is a metal compound; preferably, a ligand of the Lewis acid is an alkyl group, an alkoxy group, a carboxy group or an acetyl acetone; the Lewis acid is dialkyltin oxide. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Facile production scale synthesis of (S)-Taniguchi lactone: A precious building-block

Von Kieseritzky, Fredrik,Wang, Yeliu,Axelson, Magnus

, p. 643 - 645 (2014/06/09)

A cost-efficient and facile synthesis of (S)-4-vinyldihydrofuran-2(3H)-one ((S)-1), better known as (S)-Taniguchi lactone, is described. Racemic Taniguchi lactone rac-1 was ring-opened with (S)-1-benzylmethylamine providing a diastereomeric mixture of hyd

Asymmetric total syntheses of (-)-penicipyrone and (-)-tenuipyrone via biomimetic cascade intermolecular michael addition/cycloketalization

Song, Liyan,Yao, Hongliang,Zhu, Liangyu,Tong, Rongbiao

supporting information, p. 6 - 9 (2013/03/28)

The first total syntheses of (-)-penicipyrone and (-)-tenuipyrone were accomplished enantioselectively in 12 steps with an 11% yield and 6 steps with a 28% yield from the known 4-((tert-butyldimethylsilyl)oxy)-cyclopent-2-enone, respectively, by developing a biomimetic bimolecular cascade cyclization featuring an intermolecular Michael addition/cyclo-(spiro-)ketalization sequence. The relative, absolute stereochemistry and carbon connectivity of penicipyrone was further confirmed by X-ray crystallographic analysis and comparison of optical rotations.

Enantioselective Iridium-catalyzed allylic alkylations - Improvements and applications based on salt-free reaction conditions

Gnamm, Christian,F?rster, Sebastian,Miller, Nicole,Br?dner, Kerstin,Helmchen, Günter

, p. 790 - 794 (2007/12/29)

Simplified procedures for the Ir-catalyzed asymmetric allylic alkylation reaction are described that often allow substitution products to be obtained with ≥99% ee. Applications to syntheses of important chiral building blocks, such as the Taniguchi lacton

Highly stereoselective radical cyclization of haloacetals controlled by the acetal center

Villar, Felix,Kolly-Kovac, Tanja,Equey, Olivier,Renaud, Philippe

, p. 1566 - 1577 (2007/10/03)

A systematic investigation of radical haloacetal cyclizations (Ueno-Stork reaction) where the acetal center is the unique stereogenic element is reported. This highly diastereoselective reaction can be used for the preparation of polysubstituted tetrahydrofurans and γ-lactones. We report herein the full experimental details of reactions where up to three new chiral centers are created. To demonstrate the potential of this approach, short syntheses of (+)-eldanolide and of tricyclic acetals related to biologically active lignans have been achieved.

Radical cyclization on solid support: Synthesis of γ-butyrolactones

Watanabe, Yoshihiko,Ishikawa, Satoshi,Takao, Gou,Toru, Takeshi

, p. 3411 - 3414 (2007/10/03)

Synthesis of γ-butyrolactones using radical cyclization on solid-phase has been achieved. Polymer-supported β-bromoethylacetals were treated with tributyltin hydride in the presence of a catalytic amount of α,α'- azobisisobutyronitrile to generate intermediate carbon radicals which cyclize onto the intramolecular carbon-carbon double bond. The cyclization products were released by Jones oxidation from resin to give γ-butyrolactones in good yields.

Synthesis and absolute configuration of the insecticidal sesquilignan ( + )-haedoxan a in honour of professor G. H. Neil towers 75th birthday

Ishibashi, Fumito,Taniguchi, Eiji

, p. 613 - 622 (2007/10/03)

The insecticidal neolignan, ( + )-haedoxan A, was synthesized from (S)-( + )-vinyl-y-butyrolactone and (2R,3R)-(+)-6-formyl-7-methoxy-3-methoxymethyl-2-(3,4-methylenedioxyphenyl)-1,4- benzodioxane, and its absolute configuration was unequivocally establis

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