25047-20-5

Usage

Cyclopropane derivative

It is a derivative of cyclopropane A three-carbon ring structure, indicating its cyclic and strained nature.

Vinyl group attachment

The compound has a vinyl group (C=C) attached to the cyclopropane ring, contributing to its reactivity and versatility in organic synthesis.

Hexenyl group attachment

A (2E)-hex-2-en-1-yl group is attached to the vinyl group, further enhancing the compound's reactivity and potential applications.

Colorless liquid at room temperature

The compound appears as a colorless liquid under standard conditions, which is typical for many organic compounds.

Synthetic intermediate

1-ethenyl-1-[(2E)-hex-2-en-1-yl]cyclopropane is primarily used as a synthetic intermediate in organic chemistry, allowing for the construction of more complex molecules.

Precursor in organic compound production

The compound has potential use as a precursor, which means it can be used to produce a variety of other organic compounds through chemical reactions.

Reactivity

The presence of the vinyl and hexenyl groups makes the compound highly reactive, which is useful for various organic synthesis applications.

Versatile applications

Due to its unique structure and reactivity, 1-ethenyl-1-[(2E)-hex-2-en-1-yl]cyclopropane has a wide range of applications in organic synthesis and chemical research.

Upstream product

• 29541-98-8 pentylidenetriphenylphosphorane 
• 145987-96-8 (Z)-(2S)-1,2-epoxy-6-(trimethylsilyl)-4-hexene 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 177853-64-4 1-[(1R,2R)-((Z)-2-Hex-1-enyl)-cyclopropyl]-ethanone 
• 124062-47-1 (3S,7aR)-3-tert-Butyl-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 124062-48-2 (3S,7aR)-3-tert-Butyl-7a-methyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one 
• 760-56-5 N-allyl-N-nitrosourea 
• 39491-65-1 1,3-octadiene 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 18185-81-4 (E)-oct-3-en-1-ol 
• 72184-74-8 2-[(1S,2R)-((Z)-2-Hex-1-enyl)-cyclopropyl]-[1,3]dioxolane 
• 77188-88-6 (R)-1-[(1R,2S)-2-(2-Phenylsulfanyl-ethyl)-cyclopropyl]-hexan-1-ol 
• 77188-88-6 (S)-1-[(1R,2S)-2-(2-Phenylsulfanyl-ethyl)-cyclopropyl]-hexan-1-ol 
• 77188-87-5 Methanesulfonic acid (Z)-1-(2-phenylsulfanyl-ethyl)-non-3-enyl ester 

Downstream Products

• 33156-91-1 R-(-)-Dictyopterene C' 

Relevant academic research and scientific papers

General Cyclopropane Assembly by Enantioselective Transfer of a Redox-Active Carbene to Aliphatic Olefins

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates, and reagents, even when targeting similar compounds. This approach slows down discovery and limits available chemical space. Introduced herein is a practical and versatile diazocompound and its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. The redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect allowed the asymmetric cyclopropanation of various olefins, including unfunctionalized aliphatic alkenes, that enables the three-step total synthesis of (?)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons.

Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl Fluorides: Stereospecific Synthesis of Vinylcyclopropanes

The stereospecific reductive cross-electrophile coupling reaction of 2-vinyl-4-halotetrahydropyrans for vinylcyclopropane synthesis is reported. The nickel-catalyzed reaction occurs with both alkyl fluorides and alkyl chlorides. To the best of our knowledge, this is the first reported cross-electrophile coupling reaction of an alkyl fluoride. Ring contraction proceeds with high stereospecificity, providing selective synthesis of either diastereomer of di- and trisubstituted cyclopropanes. The utility of this methodology is demonstrated by several synthetic applications including the synthesis of the natural product dictyopterene A. 2-Vinyl-4-fluorotetrahydrofurans also undergo stereospecific ring contractions, providing access to synthetically useful hydroxymethyl cyclopropanes.

Enantiomerically Pure Vinylcyclopropylboronic Esters

Vinylcyclopropanes are versatile intermediates and products in organic synthesis. The corresponding enantiomerically pure boronic esters should lead to highly flexible building blocks with a variety of applications. A detailed study towards the selective

Synthesis of dictyopterene A

The total synthesis of dictyopterene A was accomplished via an enantiomerically pure cyclopropylboronic ester building block. Crucial olefination steps were carried out employing the Julia-Kocienski as well as the Wittig reactions. The Matteson homologation was the final key step for the total synthesis. Georg Thieme Verlag Stuttgart.

Synthesis of dictyopterene A: Optically active tributylstannylcyclopropane as a chiral synthon

Synthesis of (IS,2R)-1-[(E)-hex-1-en-1-yl]-2-vinylcyclopropane (dictyopterene A), which was isolated from the essential oil of algae of the genus Dictyopteris in Hawaii, has been demonstrated using optically active tributylstannylcyclopropane as a starting chiral synthon.

Synthesis of Vinylcyclopropanes by Intramolecular Epoxide Ring Opening. Application for an Enantioselective Synthesis of Dictyopterene A

The reaction of functionalized oxiranes 1 with the sulfur- or silicon-stabilized anions 2 provides β-heteroatom-substituted γ,δ-unsaturated epoxides 5 with, for 5e,f, a trans C=C moiety.A cis compound 9 is obtained using acetylide anion 2c via 7 and subse

Diastereoselective cyclopropanations of chiral bicyclic lactams leading to enantiomerically pure cyclopropanes. Application to the total synthesis of CIS-(1S, 3R)-deltamethrinic acid and R-(-)- dictyopterene C

A novel diastereoselective cyclopropanation based on readily available chiral bicylic lactams (1b-c, 6a-b) has provided a number of enantiomerically pure cyclopropanes. Cyclopropanations of unsaturated lactams (10a-h, 12-14) were performed using sulfur ylides as well as a 3+2 cycloaddition-photolysis sequence and furnished the desired cyclopropane adducts (16, 17, 19, 22) in fair to excellent yields. In all cases involving sulfur ylides, cyclopropanations proceeded with a high degree of exo/endo diastereoselectivity (>;90%). However, the mode of addition, exo vs endo, was found to be highly dependent on the angular substituent of the unsaturated lactam. In the case of diazoalkane cycloadditions, high regioselectivity was observed in all cases although exo/endo selectivity was governed by the diazoalkane employed. Diazoisopropane, being more reactive than diazomethane, normally led to lower diastereomeric ratios. Minor diastereomers could be readily removed by chromatography or in most cases by a single recrystallization to provide diastereomerically pure cyclopropyl bicyclic lactams (16, 17, 19, 22). Applications of this methodology to compounds of biological significance was exemplified by an asymmetric, total synthesis of cis-(1S, 3R)-deltamethrinic acid (34) and R-(-)- dictyopterene C′ (42) in high enantiomeric purity.

Synthesis of Enantiomerically Pure Pheromones of South-Pacific Brown Algae: Hormosirene and Dictyopterene A

Hormosirene ((-)-1; (1R,2R)-1-((1E,3Z)-1,3-hexadienyl)-2-vinylcyclopropane) is the specific sex attractant of several brown algae of the Australian shelf, while dictyopterene A ((+)-2; (1R,2R)-1-((1E)-1-hexenyl)-2-vinylcyclopropane) is found as a minor co

Signalstoffe und ihre Reception im Sexualcyclus mariner Braunalgen

Lockung und Schreck sind Antworten auf chemische Reize, die bereits von einzelligen Organismen ohne morphologisch abgegrenztes Nervensystem wahrgenommen und verarbeitet werden.Chemische Substanzen loesen Ereignisketten aus, die bei membrangebundenen Signalreceptoren beginnen und ueber regulierende und modulierende Glieder schliesslich die Steuerung motorischer Erfolgsorgane bewirken.Untereinheiten dieser Receptoren werden durch die bindenden Signalstoffe in gegenseitiger Abhaengigkeit konformativ veraendert, chemisch modifiziert und in ihrer molekularen Aktivitaet beeinflusst.Dieses Wechselspiel fuehrt, zusammen mit der eigentuemlichen Motorik, zu einem zielgerichteten physiologischen Verhalten, durch das die begeisselten Geschlechtszellen (Gameten) mariner Braunalgen schliesslich ihren Partner finden koennen.Die einfachen, aber jeweils hochspezifischen Systeme der Braunalgengameten wurden strukturell aufgeklaert und in ihrer biologischen Wirkung analysiert.Bei den Signalstoffen handelt es sich ueberwiegend um Monocyclen mit ungesaettigten Seitenketten (Summenformel z.B.C11H14, C11H16, C11H18).Diese Systeme erleichtern als Modelle das Verstaendnis der komplexen Ganglienschaltungen bei hoeheren Lebewesen, in denen die Sinnesorgane ueber Nervenbahnen dem Zentralnervensystem Nachrichten aus der Umwelt uebermitteln, die dort verarbeitet und, ueber ableitende Bahnen, durch den Bewegungsapparat beantwortet werden.

BIOGENETIC-TYPE SYNTHESIS OF (+/-)-DICTYOPTERENE A, AN ODORIFEROUS SUBSTANCE OBTAINED FROM BROWN SEAWEEDS, DICTYOPTERIS

Biogenetic-type synthesis of (+/-)-dictyopterene A (1) was achieved employing 1,cis-5-undecadien-3-ol (2) postulated to be a biosynthetic intermediate of 1: this synthesis means that transformation of dictyoprolene (4) into dictyopterene A (1) was formally made.