Diisoamyl (1R, 4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Brandon Quillian; Kennedy Musso; Elizabeth M. Vinson; Joseph G. Bazemore; Allison R. Marks; Clifford W. Padgett

doi:10.3390/M1852

Diisoamyl (1R, 4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Brandon Quillian, Kennedy Musso, Elizabeth M. Vinson, Joseph G. Bazemore, Allison R. Marks, Clifford W. Padgett

Southern University

Research output: Contribution to journal › Article › peer-review

Abstract

Diisoamyl (1R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (2) was prepared by reacting exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1) with isoamyl alcohol in the presence of a sulfuric acid catalyst under sonication conditions. Compound 2 was characterized by ¹H, ¹³C NMR, DEPT-135, infrared, and UV-vis spectroscopy. Gas chromatography–mass spectrometry, elemental analysis, and melting point determination were used to assess purity. The structure of compound 2 was also determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P2₁/c (14) with cell values of a = 15.5647(3) Å, b = 12.8969(2) Å, c = 9.0873(2) Å; β= 99.3920(10)°.

Original language	English
Journal	MolBank
Volume	2024
Issue number	3
DOIs	https://doi.org/10.3390/M1852
State	Published - Sep 2024
Externally published	Yes

Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Keywords

7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
7-oxanorbornene diesters
Diels–Alder
Fischer Esterification
Grubb’s catalysis monomer
isoamyl ester

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10.3390/M1852

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@article{ab97e6fff2d24fef9e46b79d3ffbb946,

title = "Diisoamyl (1R, 4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate",

abstract = "Diisoamyl (1R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (2) was prepared by reacting exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1) with isoamyl alcohol in the presence of a sulfuric acid catalyst under sonication conditions. Compound 2 was characterized by 1H, 13C NMR, DEPT-135, infrared, and UV-vis spectroscopy. Gas chromatography–mass spectrometry, elemental analysis, and melting point determination were used to assess purity. The structure of compound 2 was also determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P21/c (14) with cell values of a = 15.5647(3) {\AA}, b = 12.8969(2) {\AA}, c = 9.0873(2) {\AA}; β= 99.3920(10)°.",

keywords = "7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate, 7-oxanorbornene diesters, Diels–Alder, Fischer Esterification, Grubb{\textquoteright}s catalysis monomer, isoamyl ester",

author = "Brandon Quillian and Kennedy Musso and Vinson, {Elizabeth M.} and Bazemore, {Joseph G.} and Marks, {Allison R.} and Padgett, {Clifford W.}",

note = "Publisher Copyright: {\textcopyright} 2024 by the authors.",

year = "2024",

month = sep,

doi = "10.3390/M1852",

language = "English",

volume = "2024",

journal = "MolBank",

issn = "1422-8599",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "3",

}

TY - JOUR

T1 - Diisoamyl (1R, 4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

AU - Quillian, Brandon

AU - Musso, Kennedy

AU - Vinson, Elizabeth M.

AU - Bazemore, Joseph G.

AU - Marks, Allison R.

AU - Padgett, Clifford W.

PY - 2024/9

Y1 - 2024/9

N2 - Diisoamyl (1R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (2) was prepared by reacting exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1) with isoamyl alcohol in the presence of a sulfuric acid catalyst under sonication conditions. Compound 2 was characterized by 1H, 13C NMR, DEPT-135, infrared, and UV-vis spectroscopy. Gas chromatography–mass spectrometry, elemental analysis, and melting point determination were used to assess purity. The structure of compound 2 was also determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P21/c (14) with cell values of a = 15.5647(3) Å, b = 12.8969(2) Å, c = 9.0873(2) Å; β= 99.3920(10)°.

AB - Diisoamyl (1R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (2) was prepared by reacting exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1) with isoamyl alcohol in the presence of a sulfuric acid catalyst under sonication conditions. Compound 2 was characterized by 1H, 13C NMR, DEPT-135, infrared, and UV-vis spectroscopy. Gas chromatography–mass spectrometry, elemental analysis, and melting point determination were used to assess purity. The structure of compound 2 was also determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P21/c (14) with cell values of a = 15.5647(3) Å, b = 12.8969(2) Å, c = 9.0873(2) Å; β= 99.3920(10)°.

KW - 7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

KW - 7-oxanorbornene diesters

KW - Diels–Alder

KW - Fischer Esterification

KW - Grubb’s catalysis monomer

KW - isoamyl ester

UR - http://www.scopus.com/inward/record.url?scp=85205289197&partnerID=8YFLogxK

U2 - 10.3390/M1852

DO - 10.3390/M1852

M3 - Article

AN - SCOPUS:85205289197

SN - 1422-8599

VL - 2024

JO - MolBank

JF - MolBank

IS - 3

ER -

Diisoamyl (1R, 4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Abstract

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Keywords

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