(E)-13-(2-Bromophenyl)micheliolide

Narsimha Reddy Penthala; Shobanbabu Bommagani; Venumadhav Janganati; Sean Parkin; Peter A. Crooks

doi:10.1107/S1600536814002177

(E)-13-(2-Bromophenyl)micheliolide

Narsimha Reddy Penthala
, Shobanbabu Bommagani
, Venumadhav Janganati
, Sean Parkin
, Peter A. Crooks

Chemistry

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

Abstract

The title compound, C₂₁H₂₃BrO₃ [systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromobenzylidene)-9-hydroxy-6,9-dimethyl-3, 3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodobenzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9, 9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] under Heck reaction conditions. The title compound exhibits intramolecular O - H⋯O hydrogen bonding between the hydroxy group and the lactone ring O atom, forming a ring of graph-set motif S(6). The 2-bromophenyl group is trans to the lactone ring, indicating that this is the E isomer (geometry of the exocyclic C=C bond). The dihedral angle between the benzene ring of the 2-bromophenyl moiety and the mean plane of the lactone ring is 51.68 (7)°.

Original language	English
Pages (from-to)	o251-o252
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	70
Issue number	3
DOIs	https://doi.org/10.1107/S1600536814002177
State	Published - Mar 2014

Funding

Funders	Funder number
National Childhood Cancer Registry – National Cancer Institute	CA158275
National Institutes of Health (NIH)

Keywords

Data-to-parameter ratio = 18.0
Mean σ(C-C) = 0.004 Å
R factor = 0.025
Single-crystal X-ray study
T = 90 K
wR factor = 0.064

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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10.1107/S1600536814002177

Cite this

@article{62d61354574547c2a3966057d83f018b,

title = "(E)-13-(2-Bromophenyl)micheliolide",

abstract = "The title compound, C21H23BrO3 [systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromobenzylidene)-9-hydroxy-6,9-dimethyl-3, 3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodobenzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9, 9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] under Heck reaction conditions. The title compound exhibits intramolecular O - H⋯O hydrogen bonding between the hydroxy group and the lactone ring O atom, forming a ring of graph-set motif S(6). The 2-bromophenyl group is trans to the lactone ring, indicating that this is the E isomer (geometry of the exocyclic C=C bond). The dihedral angle between the benzene ring of the 2-bromophenyl moiety and the mean plane of the lactone ring is 51.68 (7)°.",

keywords = "Data-to-parameter ratio = 18.0, Mean σ(C-C) = 0.004 {\AA}, R factor = 0.025, Single-crystal X-ray study, T = 90 K, wR factor = 0.064",

author = "Penthala, \{Narsimha Reddy\} and Shobanbabu Bommagani and Venumadhav Janganati and Sean Parkin and Crooks, \{Peter A.\}",

year = "2014",

month = mar,

doi = "10.1107/S1600536814002177",

language = "English",

volume = "70",

pages = "o251--o252",

number = "3",

}

TY - JOUR

T1 - (E)-13-(2-Bromophenyl)micheliolide

AU - Penthala, Narsimha Reddy

AU - Bommagani, Shobanbabu

AU - Janganati, Venumadhav

AU - Parkin, Sean

AU - Crooks, Peter A.

PY - 2014/3

Y1 - 2014/3

N2 - The title compound, C21H23BrO3 [systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromobenzylidene)-9-hydroxy-6,9-dimethyl-3, 3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodobenzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9, 9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] under Heck reaction conditions. The title compound exhibits intramolecular O - H⋯O hydrogen bonding between the hydroxy group and the lactone ring O atom, forming a ring of graph-set motif S(6). The 2-bromophenyl group is trans to the lactone ring, indicating that this is the E isomer (geometry of the exocyclic C=C bond). The dihedral angle between the benzene ring of the 2-bromophenyl moiety and the mean plane of the lactone ring is 51.68 (7)°.

AB - The title compound, C21H23BrO3 [systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromobenzylidene)-9-hydroxy-6,9-dimethyl-3, 3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodobenzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9, 9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] under Heck reaction conditions. The title compound exhibits intramolecular O - H⋯O hydrogen bonding between the hydroxy group and the lactone ring O atom, forming a ring of graph-set motif S(6). The 2-bromophenyl group is trans to the lactone ring, indicating that this is the E isomer (geometry of the exocyclic C=C bond). The dihedral angle between the benzene ring of the 2-bromophenyl moiety and the mean plane of the lactone ring is 51.68 (7)°.

KW - Data-to-parameter ratio = 18.0

KW - Mean σ(C-C) = 0.004 Å

KW - R factor = 0.025

KW - Single-crystal X-ray study

KW - T = 90 K

KW - wR factor = 0.064

UR - https://www.scopus.com/pages/publications/84897675388

UR - https://www.scopus.com/pages/publications/84897675388#tab=citedBy

U2 - 10.1107/S1600536814002177

DO - 10.1107/S1600536814002177

M3 - Article

AN - SCOPUS:84897675388

SN - 1600-5368

VL - 70

SP - o251-o252

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 3

ER -

(E)-13-(2-Bromophenyl)micheliolide

Abstract

Funding

Keywords

ASJC Scopus subject areas

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