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Usage

Uses

Used in Pharmaceutical Industry:
(5Z,7E)-3-chloro-9-ethyl-2-[(2E)-pent-2-en-4-yn-1-yl]-2,3,4,9-tetrahydrooxonine is used as an intermediate compound for the synthesis of various pharmaceuticals due to its complex structure and the presence of multiple reactive sites, which can be exploited for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, (5Z,7E)-3-chloro-9-ethyl-2-[(2E)-pent-2-en-4-yn-1-yl]-2,3,4,9-tetrahydrooxonine serves as a valuable building block for the creation of more complex molecules. Its unique structure, including the tetrahydrooxonine ring and the various carbon-carbon double and triple bonds, allows for a wide range of chemical reactions and modifications, making it a versatile component in the synthesis of novel compounds with diverse applications.
Used in Material Science:
(5Z,7E)-3-chloro-9-ethyl-2-[(2E)-pent-2-en-4-yn-1-yl]-2,3,4,9-tetrahydrooxonine can be utilized in material science for the development of advanced materials with specific properties. The molecule's structural features, such as the presence of chlorine and ethyl groups, as well as the carbon-carbon double and triple bonds, can be exploited to create materials with tailored characteristics for various applications, including electronics, coatings, and adhesives.

Upstream product

• 137252-92-7 ((2R,3R)-3-vinyloxiran-2-yl)methanol 
• 181961-94-4 ethyl (2E,4S)-4-hydroxy-2-hexenoate 
• 488703-66-8 cis-t-butyldimethyl-{2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]ethoxy}dimethylsilane 
• 488703-73-7 cis-2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid 
• 488703-74-8 cis-2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]ethanol 
• 488703-79-3 (2S,8R,9S)-8-(t-butyldimethylsilyloxy)-2-ethyl-9-[(2Z)-5-(triisopropylsilyl)pent-2-en-4-ynyl]-1-oxa-3Z,5Z-cyclononadiene 

Relevant academic research and scientific papers

Total synthesis of (+)-brasilenyne: Via concise construction of an oxonane framework containing a 1,3- cis, cis -diene

The enantioselective total synthesis of (+)-brasilenyne has been accomplished. The key features of the synthesis include the convergent preparation of a highly functionalized endocyclization precursor via selective epoxide opening, the construction of an oxonene skeleton through perfect regioselective Pd(0)-catalyzed endocyclization, and the installation of a 1,3-cis,cis-diene unit via a decarboxylative photophenylselenylation and site-selective selenoxide elimination sequence.

Total synthesis of (+)-brasilenyne. Application of an intramolecular silicon-assisted cross-coupling reaction

The first enantioselective total synthesis of (+)-brasilenyne (1) has been achieved in 19 linear steps, with 5.1% overall yield from L-(S)-malic acid. The construction of the oxonin core containing a 1,3-cis, cis diene unit was accomplished with a tandem ring-closing metathesis/silicon-assisted intramolecular cross-coupling reaction. In addition, a key propargylic stereogenic center was created through a novel, highly diastereoselective ring opening of a 1,3-dioxolanone promoted by TiCl4. This reaction proceeded through an oxocarbenium ion intermediate and the asymmetric induction was fully controlled by L-malic acid residue. The C(8) stereogenic center was set by a reagent-controlled asymmetric allylboration.

Intramolecular silicon-assisted cross-coupling: Total synthesis of (+)-brasilenyne

The first, total synthesis of (+)-brasilenyne (1) has been achieved in 19 steps from l-(S)-malic acid. The key elements of this approach are a highly diastereoselective ring-opening of a 1,3-dioxolanone with bis(trimethylsilyl)acetylene) promoted by TiCl