Compounds > (2.2)paracyclophane
Page last updated: 2024-12-06

(2.2)paracyclophane

Description

(2.2)Paracyclophane is a fascinating molecule with a unique structure and interesting properties, making it a valuable tool in research across various fields. Let's break down its significance:

**What is (2.2)Paracyclophane?**

(2.2)Paracyclophane is a synthetic organic molecule belonging to the class of **cyclophanes**. It consists of two benzene rings linked by two ethylene bridges, forming a rigid cage-like structure.

* **Key Structural Features:**
* **Bridged Benzene Rings:** The two benzene rings are held in close proximity by the ethylene bridges.
* **Strain:** The molecule experiences significant strain due to the forced proximity of the aromatic rings and the bent conformation of the ethylene bridges.
* **Non-Planar Benzene:** The benzene rings are distorted from their usual planar geometry due to the bridge constraints.

**Why is it Important for Research?**

(2.2)Paracyclophane serves as a valuable model system and reagent in numerous research areas:

* **Organic Chemistry:**
* **Strain Effects:** Its highly strained structure allows researchers to study the effects of strain on chemical reactivity and molecular properties.
* **Synthesis of Complex Molecules:** The rigid, pre-organized structure facilitates the synthesis of complex molecules with unique topologies.
* **Stereochemistry:** The non-planar benzene rings introduce a new dimension to stereochemical studies.
* **Physical Chemistry:**
* **Electronic Properties:** The strain and distorted aromatic rings impact the electronic properties of the molecule, making it useful for understanding electronic interactions in complex systems.
* **Spectroscopy:** The unique structure provides distinctive spectroscopic features that can be analyzed to study molecular dynamics and interactions.
* **Material Science:**
* **Supramolecular Chemistry:** The rigid, cage-like structure allows for the creation of supramolecular assemblies with tailored properties.
* **Organic Electronics:** Its unique electronic properties make it a potential candidate for use in organic electronic devices.
* **Biochemistry:**
* **Molecular Recognition:** Its specific shape and functionalization possibilities make it a promising tool for studying molecular recognition processes.
* **Drug Delivery:** The cage-like structure can be used to encapsulate and deliver drugs or other therapeutic agents.

**In Conclusion:**

(2.2)Paracyclophane's unique structure, combined with its interesting properties, has made it a versatile tool in numerous scientific fields. Researchers continue to explore its potential for understanding fundamental principles, designing new materials, and developing innovative applications in various disciplines.

(2.2)paracyclophane: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID74210
CHEMBL ID3278516
MeSH IDM0504577

Synonyms (56)

Synonym
unii-0i9pqb142o
0i9pqb142o ,
[2.2] paracyclophane
[2.2]paracyclophane ,
tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaene
di-1,4-xylylene
cyclobis(benzene-1,4-dimethylene)
tricyclo[8.2.2.24,6,10,12,13,15-hexaene
nsc-91575
di-p-xylylene
nsc91575
tricyclo[8.2.2.2~4,7~]hexadeca-1(12),4,6,10,13,15-hexaene
inchi=1/c16h16/c1-2-14-4-3-13(1)9-10-15-5-7-16(8-6-15)12-11-14/h1-8h,9-12h
1633-22-3
tricyclo[8.2.2.2~4,7~]hexadeca-4,6,10,12,13,15-hexaene
(2,2)-paracyclophane
[2.2]paracyclophane, 97%
(2.2)paracyclophane
einecs 216-644-2
nsc 91575
tricyclo(8.2.2.24,7)hexadeca-4,6,10,12,13,15-hexaene
tricyclo(8.2.2.24,7)hexadeca-1(12),4,6,10,13,15-hexaene
[2.2]paracyclophan
P1165
AKOS004909031
di-p-xylylene; tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene;[2.2]paracyclophane
A18271
tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene
paracyclophane
tricyclo[8,2,2,24,7]hexadeca-4,6,10,12,13,15-hexaene
FT-0605407
AM20030101
CHEMBL3278516
STL324933
DTXSID9061835
SY018426
mfcd00003707
[2,2]-paracyclophane
OOLUVSIJOMLOCB-UHFFFAOYSA-N
tricyclo[8.2.2.2<4,7>]hexadeca-4,6,10,12,13,15-hexaene
[2.2]-paracyclophane
W-107955
CS-W015206
(2.2)-paracyclophane
[2,2]paracyclophane
parylene dimer
(2.2)-p-cyclophane
(2.2)(1,4)cyclophane
1,4-carbophane
AS-15801
F10672
tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaene
1,4(1,4)-dibenzenacyclohexaphane
AB89907
tricyclo[8.2.2.2,4,7]hexadeca-1(12),4,6,10,13,15-hexaene
EN300-111823
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1145576Octanol-water partition coefficient, log P of the compound1976Journal of medicinal chemistry, May, Volume: 19, Issue:5
Partition coefficients and surface areas of some alkylbenzenes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.85)18.7374
1990's0 (0.00)18.2507
2000's8 (30.77)29.6817
2010's17 (65.38)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.14

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index38.14 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index51.30 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.14)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.85%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (96.15%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
benzene
[no description available]		2.3920aromatic annulene;
benzenes;
volatile organic compound		carcinogenic agent;
environmental contaminant;
non-polar solvent
methane
Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).		2.1110alkane;
gas molecular entity;
mononuclear parent hydride;
one-carbon compound		bacterial metabolite;
fossil fuel;
greenhouse gas
imidazole
imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.		2.0610imidazole
nickel
Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.		2.0310metal allergen;
nickel group element atom		epitope;
micronutrient
hydroxide ion
[no description available]		2.1710oxygen hydridemouse metabolite
pyridine
azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.		2.0610azaarene;
mancude organic heteromonocyclic parent;
monocyclic heteroarene;
pyridines		environmental contaminant;
NMR chemical shift reference compound
toluene
methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.		1.9510methylbenzene;
toluenes;
volatile organic compound		cholinergic antagonist;
fuel additive;
neurotoxin;
non-polar solvent
ethane
Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.		2.0510alkane;
gas molecular entity		plant metabolite;
refrigerant
2-xylene
2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.		1.9510xylene
tert-butylbenzene
[no description available]		1.9510
cumene
cumene : An alkylbenzene that is benzene carrying an isopropyl group.		1.9510alkylbenzene
ethylbenzene
[no description available]		1.9510alkylbenzene
n-propylbenzene
n-propylbenzene: RN given refers to parent cpd. propylbenzene : An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.		1.9510alkylbenzene
4-xylene
p-xylene : A xylene with methyl groups at positions 1 and 4.		1.9510xylene
3-xylene
m-xylene : A xylene carrying methyl groups at positions 1 and 3.		1.9510xylene
tetralin
tetralin: structure given in first source. tetralin : An ortho-fused bicyclic hydrocarbon that is 1,2,3,4-tetrahydro derivative of naphthalene.		1.9510ortho-fused bicyclic hydrocarbon;
tetralins
oxazoles
Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.		2.11101,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
indan
indan: structure in first source. indane : An ortho-fused bicyclic hydrocarbon consisting of a benzene ring fused to a cyclopentane ring; a high-boiling (176 (o)C) colourless liquid.		1.9510indanes;
ortho-fused bicyclic hydrocarbon
phenylcyclohexane
phenylcyclohexane: pyrolysis product of phencyclidine		1.9510
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		2.0610metal allergen;
nickel group element atom;
platinum group metal atom
gold
Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.		2.0610copper group element atom;
elemental gold
pyrene
pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.		2.0610ortho- and peri-fused polycyclic arenefluorescent probe;
persistent organic pollutant
carbene
carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).		2.1110carbene;
methanediyl
fullerene c60
Fullerenes: A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.. fullerene : A compound composed solely of an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. The term has been broadened to include any closed cage structure consisting entirely of three-coordinate carbon atoms.		2.4820fullerenegeroprotector
lithium
Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.		2.1310alkali metal atom
zinc protoporphyrin ix
[no description available]		2.0610
boron
Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.		2.1110boron group element atom;
metalloid atom;
nonmetal atom		micronutrient
ConditionIndicatedRelationship StrengthStudiesTrials
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