102369-06-2

Basic information

• Product Name: 2,3-EPOXYDECANAL
• Synonyms: 2,3-EPOXYDECANAL;3-HEPTYL-OXIRANECARBOXALDEHYDE
• CAS NO: 102369-06-2
• Molecular Formula: C10H18O2
• Molecular Weight: 170.25
• Mol File: 102369-06-2.mol

Chemical Properties

• Boiling Point: 242.0±15.0 °C(Predicted)
• Appearance: /
• Density: 0.995±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,3-EPOXYDECANAL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-EPOXYDECANAL(102369-06-2)
• EPA Substance Registry System: 2,3-EPOXYDECANAL(102369-06-2)

Safety Data

• Hazardous Substances Data: 102369-06-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,3-EPOXYDECANAL is used as a key intermediate in the synthesis of polymers, resins, and other organic compounds. Its reactive epoxide group allows for the formation of various chemical bonds, making it a versatile building block in the chemical industry.
Used in Flavoring Agents for the Food Industry:
Leveraging its distinctive odor, 2,3-EPOXYDECANAL is used as a flavoring agent in the food industry. It contributes to the development of specific taste profiles in various food products, enhancing the sensory experience for consumers.
Used in Pharmaceutical Development:
2,3-EPOXYDECANAL is studied for its potential antimicrobial and antifungal properties. Its ability to combat microorganisms makes it a candidate for the development of new pharmaceuticals, particularly in the area of antimicrobial resistance.
Used in Disinfectant Products:
Due to its antimicrobial and antifungal properties, 2,3-EPOXYDECANAL is of interest in the development of disinfectant products. It could be incorporated into formulations to enhance their effectiveness against a range of pathogens.
Used in Research:
2,3-EPOXYDECANAL is also used in research settings to study its chemical properties and potential applications. This includes exploring its reactivity, stability, and interactions with other compounds, which can lead to new discoveries and applications in various fields.
It is important to handle 2,3-EPOXYDECANAL with care due to its potential to cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken during its use to minimize any adverse effects.

Upstream product

• 99745-00-3 (2S,3S)-2,3-epoxydecan-1-ol 
• 123932-68-3 (2R,3S)-3-heptyloxirane methanol 
• 3913-81-3 (E)-2-decenal 
• 629-04-9 1-Bromoheptane 
• 4117-14-0 2-decyn-1-ol 
• 4194-71-2 (Z)-2-decen-1-ol 
• 107796-95-2 ((2R,3R)-3-heptyloxiran-2-yl)methanol 

Downstream Products

• 1308381-54-5 tert-butyl[(Z)-3-[(2S,3S)-3-heptyloxiran-2-yl]allyloxy]diphenylsilane 
• 107033-43-2 [(2S,3R)-3-heptyloxiran-2-yl]methanol 

Relevant articles and documents

Total syntheses of 9-epoxyfalcarindiol and its diastereomer

The first total syntheses of 9-epoxyfalcarindiol 1a and its diastereomer 1b have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)4.

Stereoselective Total Synthesis of (+)-Virol C

A highly stereoselective synthesis of (+)-Virol C (1) has been achieved starting from octan-1-ol (6) using two different strategies, elimination reactions of epoxyallyl chloride 12 and epoxy chloride 16 to hydroxyenyne 2 and trans-hydroxyalkenyl chloride 4 as key reactions in route a and route b, respectively.

Green asymmetric synthesis of epoxypeptidomimetics and evaluation as human cathepsin K inhibitors

Cathepsin K (CatK) is a cysteine protease known for its potent collagenolytic activity, being recognized as an important target to the development of therapies for the treatment of bone disorders. Epoxypeptidomimetics have been reported as potent inhibitors of cathepsins, thus in this work we present a green synthesis of new peptidomimetics by using a one-pot asymmetric epoxidation/Ugi multicomponent reaction. The compounds were evaluated against CatK showing selectivity when compared with cathepsin L, with an inhibition profile in the low micromolar IC50 range. Investigation of the mechanism of action carried out for compounds LSPN428 and LSPN694 suggested a mixed inhibition mode and docking studies allowed a better understanding about interactions of inhibitors with the enzyme.

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions

An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The one-pot procedure showed great efficiency in promoting stereoselective multicomponent transformations in a tandem, 'green' fashion. Because of its non-residual, efficient and selective character, this synthetic design shows promise for large-scale applications in both diversity and target-oriented syntheses. The Royal Society of Chemistry 2012.

Synthesis of syn and anti 1,4-diols by copper-catalyzed boration of allylic epoxides

Two sides of the same coin: Syn and anti 1,4-diols have been synthesized through the regio- and diastereoselective CuI-catalyzed boration of allylic epoxides (see scheme; pin=pinacolato, TES=triethylsilyl). In situ protection of the alcohol all

Asymmetric formal trans -dihydroxylation and trans -aminohydroxylation of α,β-unsaturated aldehydes via an organocatalytic reaction cascade

This study demonstrates the first formal asymmetric trans-dihydroxylation and trans-aminohydroxylation of α,β-unsaturated aldehydes in an organocatalytic multibond forming one-pot reaction cascade. This efficient process converts α,β-unsaturated aldehydes into optically active trans-2,3-dihydroxyaldehydes and trans-3-amino-2-hydroxyaldehydes with the aldehyde moiety protected as an acetal. The elaborated one-pot protocol proceeds via the formation of 2,3-epoxy and 2,3-aziridine aldehyde intermediates, which subsequently participate in a novel NaOMe-initiated rearrangement reaction leading to the formation of acetal protected trans-2,3-dihydroxyaldehydes and trans-3-amino-2-hydroxyaldehydes in a highly stereoselective manner. Advantageously, this multibond forming reaction cascade can be performed one-pot, thereby minimizing the number of manual operations and purification procedures required to obtain the products. Additionally, for the purpose of trans-aminohydroxylation of the α,β-unsaturated aldehydes, a new enantioselective aziridination protocol using 4-methyl-N-(tosyloxy) benzenesulfonamide as the nitrogen source has been developed. The mechanism of the formal trans-dihydroxylation and trans-aminohydroxylation of α,β-unsaturated aldehydes is elucidated by various investigations including isotopic labeling studies. Finally, the products obtained were applied in the synthesis of numerous important molecules.

Alkylative Elimination of α,β-Epoxy Tosylhydrazones

Optically pure allyl alcohols have been prepared from tosylhydrazones derived from chiral epoxy aldehydes by alkylative elimination utilizing alkyl magnesium reagents.

An expeditious approach to the synthesis of chiral butadienyl alcohols

A highly regioselective reduction of epoxy allylic alcohols to chiral butadienyl alcohols and its application to taxol skeleton is described.