120409-13-4

Basic information

• Product Name: (1R,4R,6R)-6-(benzenesulfinyl)bicyclo[2.2.1]hept-2-ene
• Synonyms: (1R,4R,6R)-6-(benzenesulfinyl)bicyclo[2.2.1]hept-2-ene;bicyclo(2.2.1)hept-5-en-2-yl phenyl sulfoxide
• CAS NO: 120409-13-4
• Molecular Formula: C₁₃H₁₄OS
• Molecular Weight: 218.31
• Mol File: 120409-13-4.mol

Chemical Properties

• Boiling Point: 382.906°C at 760 mmHg
• Flash Point: 185.375°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: (1R,4R,6R)-6-(benzenesulfinyl)bicyclo[2.2.1]hept-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R,6R)-6-(benzenesulfinyl)bicyclo[2.2.1]hept-2-ene(120409-13-4)
• EPA Substance Registry System: (1R,4R,6R)-6-(benzenesulfinyl)bicyclo[2.2.1]hept-2-ene(120409-13-4)

Safety Data

• Hazardous Substances Data: 120409-13-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,4R,6R)-6-(benzenesulfinyl)bicyclo[2.2.1]hept-2-ene is utilized as a key intermediate in organic synthesis for the creation of various complex organic molecules. Its unique structure allows for multiple points of reactivity, making it an ideal candidate for constructing intricate molecular frameworks.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (1R,4R,6R)-6-(benzenesulfinyl)bicyclo[2.2.1]hept-2-ene is employed as a building block for the synthesis of pharmaceuticals. Its incorporation into drug molecules can potentially lead to the development of new therapeutic agents with novel mechanisms of action and improved pharmacological profiles.
Used in the Development of Biologically Active Compounds:
(1R,4R,6R)-6-(benzenesulfinyl)bicyclo[2.2.1]hept-2-ene's distinctive sulfinyl group and bicyclic structure make it a promising starting point for the design of biologically active molecules. It is used as a structural motif in the development of new chemical entities that may exhibit specific biological activities, such as enzyme inhibition, receptor modulation, or other pharmacological effects.
Used in Pharmaceutical Industry:
(1R,4R,6R)-6-(benzenesulfinyl)bicyclo[2.2.1]hept-2-ene is used as a precursor in the pharmaceutical industry for the synthesis of innovative drug candidates. Its unique attributes facilitate the exploration of new chemical space, potentially leading to the discovery of breakthrough treatments for various diseases and medical conditions.

InChI:InChI=1/C13H14OS/c14-15(12-4-2-1-3-5-12)13-9-10-6-7-11(13)8-10/h1-7,10-11,13H,8-9H2/t10-,11+,13-,15+/m1/s1

Upstream product

• 74491-16-0 4-phenylsulphinyl-4-methylpentan-2-one 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 20451-53-0 Phenyl vinyl sulfoxide 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 69582-37-2 exo-5-phenylthiobicyclo[2.2.1]hept-2-ene 

Relevant articles and documents

The Structures of Different Diastereomers of Bicyclohept-5-en-2-yl Phenyl Sulfoxide

Three diastereomers of bicyclohept-5-en-2-yl phenyl sulfoxide were prepared by Diels-Alder cycloadditions between phenyl vinyl sulfoxide and cyclopentadiene.The isomers were separeted by column chromatography on silica gel and repeated recrystallizations gave the pure racemates of three of the four possible diastereomers.It proved to be impossible to assign the stereochemistry of the products from low-resolution NMR spectra.The X-ray diffraction studies of the three diastereomers showed the relative configuration at the two chiral centers and these stereochemical assignments were, subsequently, correlated with the two-dimensional NMR spectroscopic results.Compound (I), exo-(2R*,8S*)-bicyclohept-5-en-2-yl phenyl sulfoxide *,8R*)-isomer>, C13H14OS, Mr=218.31, orthorhombic, P212121, a=10.517(2), b=10.914(2), c=9.642(3) Angstroem, V=1106.7 Angstroem3, Z=4, Dx=1.31 gcm-3, Cu Kα, λ=1.54178 Angstroem, μ=22.14 cm-1, F(000)=464, T=138(2) K, R=0.042 for 1151 data.Compound (II), exo-(2RS,8RS)-bicyclohept-5-en-2-yl phenyl sulfoxide, C13H14OS, Mr=218.31, triclinic, P1, a=8.775(4), b=16.353(8), c=7.804(3) Angstroem, α=90.67(3), β=101.08(4), γ=85.64 (5) deg, V=1095.8 Angstroem3, Z=4, Dx=1.32 gcm-1, Mo Kα, λ=0.71069 Angstroem, μ=2.18 cm-1, F(000)=464, T=138(2) K, R=0.062 for 3264 data.The two molecules in the asymmetric unit are crystallographically independent, but their conformations are similar.Compound (III), endo-(2SR,8SR)-bicyclohept-5-en-2-yl phenyl sulfoxide, C13H14OS, Mr=218.31, orthorhombic, P212121, a=14.454(2), b=14.800(2), c=10.388(1) Angstroem, V=2222.2 Angstroem3, Z=8, Dx=1.31 gcm-1, Mo Kα, λ=0.71069 Angstroem, μ=2.15 cm-1, F(000)=928, T=138(2) K, R=0.029 for 2385 data.The two molecules in the asymmetric unit are enantiomeric with respect to both chiral atoms C(2) and S(8) and their conformations show small differences.For both the exo-(2RS,8RS) and endo-(2SR,8SR) conformers, the two molecules in the asymmetric unit have closely similar molecular dimensions.The results show an appreciable distortion from mirror symmetry for the norbornene ring system.The distortion is similar in size for the compounds but in opposite directions for the 2-exo- and the 2-endo-substituted norbornene system.

Preparation and Trapping of Sulphenic Acids

Benzene- and toluene-α-sulphenic acids have been prepared under mild conditions from 4-benzenesulphinyl- and 4-toluene-α-sulphinyl-4-methylpentan-2-one respectively.The acids were trapped with norbornadiene.