Title: Longifolene
CAS Registry Number: 475-20-7
CAS Name: [1S-(1a,3ab,4a,8ab)]-Decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene
Additional Names: junipene; kuromatsuene
Molecular Formula: C15H24
Molecular Weight: 204.35
Percent Composition: C 88.16%, H 11.84%
Literature References: Tricyclic sesquiterpene present to the extent of 5-10% in Indian turpentine oil which is produced commercially from the Himalayan pine, Pinus longifolia Roxb., Pinaceae: J. L. Simonsen, J. Chem. Soc. 117, 570 (1920). Structure: R. H. Moffett, D. Rogers, Chem. Ind. (London) 1953, 916; P. Naffa, G. Ourisson, ibid. 917. Abs config: G. Ourisson, Bull. Soc. Chim. Fr. 1955, 895. Identity of longifolene with junipene and kuromatsuene: S. Akiyoshi et al., Tetrahedron 9, 237 (1960). Total synthesis of naturally occurring (+)-form: E. J. Corey et al., J. Am. Chem. Soc. 86, 478 (1964); of the (±)-form: eidem, ibid. 83, 1251 (1961); J. E. McMurray, S. J. Isser, ibid. 94, 7132 (1972); R. A. Volkmann et al., ibid. 97, 4777 (1975). Review of chemistry of longifolene and its derivs: S. Dev, Acc. Chem. Res. 14, 82-88 (1981); idem, Fortschr. Chem. Org. Naturst. 40, 50-104 (1981).
Properties: Viscous oil, bp706 254-256°, bp15 126-127°. [a]D18 +42.73°. d418 0.9319; nD20 1.5040. Insol in water; sol in benzene.
Boiling point: bp706 254-256°; bp15 126-127°
Optical Rotation: [a]D18 +42.73°
Index of refraction: nD20 1.5040
Density: d418 0.9319
Derivative Type: Borane deriv
Additional Names: Dilongifolylborane
Molecular Formula: C30H51B
Molecular Weight: 422.54
Percent Composition: C 85.28%, H 12.17%, B 2.56%
Properties: Heavy, snow-white, shiny plates, mp 160-161° (sealed, evacuated capillary). Strongly dimeric. Sparingly sol in common organic solvents. Prepn and use in hydroboration: P. K. Jadhav, H. C. Brown, J. Org. Chem. 46, 2988 (1981).
Melting point: mp 160-161° (sealed, evacuated capillary)
Use: Borane deriv as a chiral hydroborating agent. |