927810-77-3

Basic information

• Product Name: Ethyl Cyclopropylcarboxylate-d4
• Synonyms: Cyclopropanecarboxylic Acid Ethyl Ester-d4;Ethyl Cyclopropanecarboxylate-d4;NSC 60696-d4;Ethyl Cyclopropylcarboxylate-d4
• CAS NO: 927810-77-3
• Molecular Formula: C6H6D4O2
• Molecular Weight: 118.167047112
• Product Categories: Isotope Labelled Compounds;Miscellaneous Reagents
• Mol File: 927810-77-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl Cyclopropylcarboxylate-d4(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl Cyclopropylcarboxylate-d4(927810-77-3)
• EPA Substance Registry System: Ethyl Cyclopropylcarboxylate-d4(927810-77-3)

Safety Data

• Hazardous Substances Data: 927810-77-3(Hazardous Substances Data)

Usage

Description

Ethyl Cyclopropylcarboxylate-d4 is a deuterated organic compound that features a cyclopropane ring with an ester functional group. It is characterized by its colorless oil appearance and is commonly used as a reagent in chemical reactions involving the addition of labelled cyclopropane.

Uses

Used in Chemical Synthesis:
Ethyl Cyclopropylcarboxylate-d4 is used as a reagent for the addition of labelled cyclopropane in chemical synthesis processes. Its deuterated nature allows for the tracking and analysis of reaction mechanisms and pathways, providing valuable insights into the behavior of cyclopropane-containing compounds during synthesis.
Used in Research and Development:
In the field of research and development, Ethyl Cyclopropylcarboxylate-d4 serves as a valuable tool for studying the properties and reactions of cyclopropane rings. Its use in controlled experiments can help scientists understand the effects of isotopic substitution on reaction kinetics and the stability of intermediates, contributing to the advancement of organic chemistry knowledge.
Used in Analytical Chemistry:
Ethyl Cyclopropylcarboxylate-d4 can be employed in analytical chemistry as a reference compound or internal standard for the accurate measurement and quantification of related compounds. Its deuterated form provides a distinct signature that can be easily distinguished from non-deuterated analogs, enhancing the precision of analytical techniques such as mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl Cyclopropylcarboxylate-d4 may be utilized in the development of new drugs containing cyclopropane rings. Its deuterated form can aid in the investigation of drug metabolism, pharmacokinetics, and potential side effects, ultimately contributing to the design of safer and more effective medications.
Used in Material Science:
Ethyl Cyclopropylcarboxylate-d4 can also find applications in material science, particularly in the synthesis of novel materials with unique properties. The incorporation of deuterated cyclopropane rings into polymers or other materials can lead to altered physical or chemical characteristics, opening up new possibilities for material development and innovation.

Upstream product

• 927810-76-2 ethyl 4-chlorohexadeuteriobutanoate 

Relevant articles and documents

Stereoselective preparation of six diastereomeric quatercyclopropanes from bicyclopropylidene and some derivatives

Diastereomeric meso- and d,l-bis(bicyclopropylidenyl) (5) were obtained upon oxidation with oxygen of a higher-order cuprate generated from lithiobicyclopropylidene (4) in 50 and 31 % yield, respectively. Their perdeuterated analogues meso-[D14]- and d,l-[D14]-5 were obtained along the same route from perdeuterated bicyclopropylidene [D 8]-3 (synthesized in six steps in 7.4% overall yield from [D8]-THF) in 20.5% yield each. Dehalogenative coupling of 1,1-dibromo-2- cyclopropylcyclopropane (6) gave a mixture of all possible stereoisomers of 1,5-dicyclopropylbicyclopropylidene 16 in 69% yield, from which (Z)-cis-16 was separated by preparative gas chromatography (26% yield). The crystal structure of meso-5 looks like a super-position of the crystal structures of two outer bicyclopropylidene units (3) and one inner s-rrans-bicyclopropyl unit, whereas the two outer cyclopropyl moieties adopt a gauche orientation with respect to the cyclopropane rings at the inner bicyclopropylidene units in (Z)-cis-16. Birch reduction with lithium in liquid ammonia of meso-5 and d,l-5 gave two pairs of diastereomeric quatercyclopropanes trans,trans-(R*,S*, R*, S*)-17/cis,trans-(R*,S*,R*,R*)-18 and trans,trans-(R*,S*,S*,R*)-19/cis,trans-(R*, S*,S*,S*)-20 in 97 and 76% yield, respectively, in a ratio 9:1 for every pair. The latter diastereomer was also obtained as the sole product by Birch reduction of (Z)-cis-16 in 96% yield. Under the same conditions, tetradecadeuterio analogues trans,trans-[D14]-(R*S*, R*,S*)-17/cis,trans-[D14]-(R*, S*,R*, R*)-18 (8:1) and trans,trans[D14]-(R*,S*,S*, R*)-19/cis,trans-[D14](R*,S*,S*,S*)-20 (12:1) were prepared from mwo-[D14]-5 and d,l-[D14]-5 in 37 and 63 % yield, respectively. Reduction of meso-5 with diimine gave the cis,cisquatercyclopropane (S*,S*,R*,R*)-21 as the main product (58% yield) along with the cis,trans-diastereomer (S*,S*, R*,S*)-18 (29% yield). Thus, five of the six possible diastereomeric quatercyclopropanes were obtained from meso-5, d,l-5, and (Z)-cis-16. The X-ray crystal structure analyses of transjrans-(R*,S*,R*,S*)- 17 and cis,cis(S*,S*,R*,R*)-21 revealed for the both an unusual conformation in which the central bicyclopropyl unit adopts an s-fran.s-(antiperiplanar) orientation with φ=180.0°, and the two terminal bicyclopropyl moieties adopt a synclinal conformation with φ = 49.8 and 72.0°, respectively. In solution the vicinal coupling constants 〈3JH,H〉 in trans,trans(R*,R*, R*,S*)-[D14]-17, trans,trans(R*,S*,S*, R*)-[D14]-19, trans,trans(R*,S*,R*,R*)- [D14]-18 and trans,cis(R*,S*,S*,S*)-[D 14]-20 were found to be 4.1, 4.7, 5.9 and 5.9 Hz, respectively. This indicates a predominance of the all-gauche conformer in (R*,S*, R*,S*)-17 and a decreasing fraction of it in this sequence of the other diastereomers.