NORCARANE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H12
Molecular Weight	96.1702
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1[C@H]2CCCC[C@@H]12

InChI

InChIKey=WPHGSKGZRAQSGP-KNVOCYPGSA-N

InChI=1S/C7H12/c1-2-4-7-5-6(7)3-1/h6-7H,1-5H2/t6-,7+

HIDE SMILES / InChI

Molecular Formula	C7H12
Molecular Weight	96.1702
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Manganese porphyrins catalyze selective C-H bond halogenations.	2010-09-22	20806921
The effect of a complexed lithium cation on a norcarane-based radical clock.	2009	19156804
Dihalocarbene insertion reactions into C-H bonds of compounds containing small rings: mechanisms and regio- and stereoselectivities.	2007-10-26	17918998
Synthesis of novel bicyclo[4.1.0]heptane and bicyclo[3.1.0]hexane derivatives as melanin-concentrating hormone receptor R1 antagonists.	2007-09-01	17604169
A potent bicyclic inhibitor of a family 27 alpha-galactosidase.	2007-06-07	17520141
Products from enzyme-catalyzed oxidations of norcarenes.	2007-02-16	17288367
Desaturase reactions complicate the use of norcarane as a mechanistic probe. Unraveling the mixture of twenty-plus products formed in enzyme-catalyzed oxidations of norcarane.	2007-02-16	17288366
Profiling mechanisms of alkane hydroxylase activity in vivo using the diagnostic substrate norcarane.	2007-02	17317570
Oxygen-18 tracer studies of enzyme reactions with radical/cation diagnostic probes.	2005-12-09	16168953
Reaction mechanisms of non-heme diiron hydroxylases characterized in whole cells.	2005-10	16084596
Remarkable aliphatic hydroxylation by the diiron enzyme toluene 4-monooxygenase in reactions with radical or cation diagnostic probes norcarane, 1,1-dimethylcyclopropane, and 1,1-diethylcyclopropane.	2004-12-21	15595825
endo/exo isomerism in norcarane and 2-norcaranol hydrotrioxides (ROOOH).	2003-11-14	14604395
Xylene monooxygenase, a membrane-spanning non-heme diiron enzyme that hydroxylates hydrocarbons via a substrate radical intermediate.	2003-09	12811621
Evaluation of norcarane as a probe for radicals in cytochome p450- and soluble methane monooxygenase-catalyzed hydroxylation reactions.	2002-06-19	12059209
Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane.	2002-05-29	12022835
Intermediate Q from soluble methane monooxygenase hydroxylates the mechanistic substrate probe norcarane: evidence for a stepwise reaction.	2001-12-05	11724588

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:13:06 GMT 2025` Edited by `admin` on `Mon Mar 31 21:13:06 GMT 2025`
Record UNII	ZGC3T0R48Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORCARANE

Systematic Name

English

NSC-143399

Preferred Name

English

CIS-BICYCLO(4.1.0)HEPTANE

Systematic Name

English

(±)-NORCARANE

Systematic Name

English

NORCARANE [MI]

Common Name

English

BICYCLO(4.1.0)HEPTANE

Systematic Name

English

1,2-METHYLENECYCLOHEXANE

Common Name

English

Code System Code Type Description

FDA UNII

ZGC3T0R48Q