181-15-7

Basic information

• Product Name: spiro[5.6]dodecane
• Synonyms: spiro[5.6]dodecane
• CAS NO: 181-15-7
• Molecular Formula: C12H22
• Molecular Weight: 166.3031
• Mol File: 181-15-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 229.56°C (rough estimate)
• Flash Point: 85.8°C
• Appearance: /
• Density: 0.8348 (estimate)
• Vapor Pressure: 0.0554mmHg at 25°C
• Refractive Index: 1.4850 (estimate)
• CAS DataBase Reference: spiro[5.6]dodecane(CAS DataBase Reference)
• NIST Chemistry Reference: spiro[5.6]dodecane(181-15-7)
• EPA Substance Registry System: spiro[5.6]dodecane(181-15-7)

Safety Data

• Hazardous Substances Data: 181-15-7(Hazardous Substances Data)

Usage

General Description

Spiro[5.6]dodecane, also known as 1,2,3,4,5,6,7,8,9,9a-decahydro-1,4-methano-1H-phenanthrene, is a bicyclic hydrocarbon molecule with a unique structure containing two fused cyclohexane rings in a spiro arrangement. It is a type of polycyclic hydrocarbon and belongs to the class of spiro compounds. This chemical is widely used in the pharmaceutical and fragrance industry as a building block for the synthesis of various pharmaceuticals and fragrances. Its unique structure and stability make it a valuable molecule for organic synthesis, and it also exhibits interesting biological and pharmacological properties. Spiro[5.6]dodecane has potential applications in the development of new drugs and fragrances, making it an important molecule in the field of organic chemistry and chemical industry.

InChI:InChI=1/C12H22/c1-2-5-9-12(8-4-1)10-6-3-7-11-12/h1-11H2

Upstream product

• 4728-90-9 spiro[5.6]dodecan-7-one 
• 2888-11-1 1,1'-bicyclohexane-1,1'-diol 
• 108-94-1 cyclohexanone 
• 111-24-0 1,5-dibromo-pentane 
• 42540-18-1 <5.3.2>propellanone 
• 344447-87-6 C₁₆H₂₆S₄ 
• 4728-93-2 spiro<5.6>dodecan-7-one 
• 502-42-1 cycloheptanone 
• 88288-23-7 (1S*,6R*,7S*)-7-Hydroxytricyclo<5.3.2.0^1,6>dodecan-6-yl Acetate 
• 88314-93-6 (1S*,6R*,7S*)-6-Hydroxytricyclo<5.3.2.0^1,6>dodecan-7-yl Acetate 
• 88288-30-6 spiro<5.6>dodecane-1,9-dione 
• 88314-92-5 (1S*,6R*,7S*)-Tricyclo<5.3.2.0^1,6>dodecane-6,7-diol 

Relevant articles and documents

Novel Acid-catalysed Rearrangement of - and -Propellanones

The reactions of the - and -propellanones (1) and (2) with toluene-p-sulphonic acid in acetic acid or sulphuric acid in aqueous tetrahydrofuran led to the tricyclo1,5>undecane derivatives (5) or (6) and the tricyclo1,6>dodecane derivatives (7) or (8), respectively, by a novel rearrangement.

Acid-Catalyzed Rearrangement of Propellanones

The acid-catalyzed rearrangement of propellanones (m = 3-5, n = 3,4) was studied to ascertain the effect of ring size on the mode of rearrangement.Propellanones 9 and 10, containing a five-membered cycloalkanone ring, did not rearrange.Propellanones containing a six- or seven-membered cycloalkanone ring (11-14) rearranged smoothly to cyclopentanones 17a, 18, and 19 in a nonnucleophilic medium.In the presence of a nucleophile, the course of the rearrangement depended on wether the third cycloalkane ring contained three, four, or five carbon atoms.Thus propellanones 11 and 14 rearranged to (1S*,5R*,6S*)-tricyclo1,5>undecane derivatives 20a,b and -tricyclo1,6>dodecane derivatives 22a and 23 by an unusual 1,2 alkyl shift of the central propellane bond followed by nuleophilic attack.The structures of 20a,b, 22a, and 23 were established by chemical transformations (Scheme II).The stereochemistry of methyl substituents on the cyclobutane ring of dimethylpropellanones 15 and 16 influenced the course of rearrangement in the presence of a nucleophile.