Crystal structure of (1S,3R,8R,9R)-2,2-di­chloro-3,7,7-tri­methyl-10-methylenetri­cyclo­[6.4.0.01,3]dodecan-9-ol

نویسندگان

  • Ahmed Benzalim
  • Aziz Auhmani
  • Abdoullah Bimoussa
  • My Youssef Ait Itto
  • Jean-Claude Daran
  • Abdelwahed Auhmani
چکیده

The title compound, C16H24Cl2O, was synthesized by treating (1S,3R,8S,9R,10S)-2,2-di-chloro-3,7,7,10-tetra-methyl-9,10-ep-oxy-tri-cyclo-[6.4.0.0(1,3)]dodecane with a concentrated solution of hydro-bromic acid. It is built up from three fused rings: a cyclo-heptane ring, a cyclo-hexyl ring bearing alkene and hy-droxy substituents, and a cyclo-propane ring bearing two chlorine atoms. The asymmetric unit contains two mol-ecules linked by an O-H⋯O hydrogen bond. In the crystal, further O-H⋯O hydrogen bonds build up an R 4 (4)(8) cyclic tetra-mer. One of the mol-ecules presents disorder that affects the seven-membered ring. In both mol-ecules, the six-membered rings display a chair conformation, whereas the seven-membered rings display conformations inter-mediate between boat and twist-boat for the non-disordered mol-ecule and either a chair or boat and twist-boat for the disordered mol-ecule owing to the disorder. The absolute configuration for both mol-ecules is 1S,3R,8R,9R and was deduced from the chemical pathway and further confirmed by the X-ray structural analysis.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Absolute configuration of (1S,3R,8R)-10-bromo­methyl-2,2-di­chloro-3,7,7-tri­methyl­tri­cyclo­[6.4.0.01,3]dodec-9-ene

The absolute configuration of the title compound, C16H23BrCl2, has been deduced from the chemical pathway and fully confirmed by refinement of the Flack and Hooft parameters. The six-membered ring adopts a half-chair conformation, whereas the seven-membered ring is a twisted chair. The mol-ecular packing within the crystal is stabilized only by van der Waals inter-actions.

متن کامل

Crystal structure of (1S,3R,8R,9S,10R)-10-bromo­methyl-2,2-di­chloro-9,10-ep­oxy-3,7,7-tri­methyl­tri­cyclo­[6.4.0.01,3]dodeca­ne

The title compound, C16H23BrCl2O, was synthesized in three steps from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (cedrus atlantica). The mol-ecule is built up from two fused six- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a screw-boat conformation...

متن کامل

(1S,3R,8R,11S)-11-Bromo-10-bromo­methyl-2,2-di­chloro-3,7,7-tri­methyl­tricyclo­[6.4.0.01,3]dodec-9-ene

The title compound, C16H22Br2Cl2, was synthesized from β-him-achalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule is built up from fused six- and seven-membered rings and an appended three-membered ring. The six-membered ring has a half-chair conformation, whereas the seven-...

متن کامل

Crystal structure of (1S,3R,8R,10S)-2,2-di­chloro-10-hy­droxy-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.01,3]dodecan-9-one

The asymmetric unit of the title compound, C16H24Cl2O2, contains two independent mol-ecules (A and B) which are built from three fused rings, viz. a seven-membered heptane ring, a six-membered cyclo-hexyl ring bearing a ketone and an alcohol group, and a cyclo-propane ring bearing two Cl atoms. In the crystal, the two mol-ecules are linked via two O-H⋯O hydrogen bonds, forming an A-B dimer with...

متن کامل

Crystal structure of (1S,3R,8R,9R,10S)-2,4,6-tris­(2,2-di­chloro-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.01,3]dodec-9-yl)cyclo­triboroxane

The title compound, C48H75B3Cl6O3, was synthesized in two steps from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-hept-ene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule consists of an almost planar cyclo-triboroxane ring [maximum deviation = 0.036 (2) Å] linked to three identical fused ring systems with different c...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:

دوره 72  شماره 

صفحات  -

تاریخ انتشار 2016