cis-2-methyl-5-(1-methylvinyl)cyclohex-2-en-1-yl acetate

The 2-Cyclohexen-1-ol,2-methyl-5-(1-methylethenyl)-, 1-acetate, (1R,5R)-rel-, with its CAS registry number 1205-42-1, has the IUPAC name of [(1R,5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-yl] acetate. And as a kind of colourless to light yellow liquid, it has the molecular formula of C₁₂H₁₈O₂ and the molecular weight of 194.27. Besides, it could be made form the direct esterification of levorotatory almost alcohol, acetic anhydride and sodium acetate. When comes to its usage, it is often used in ingredient of all kind of essence, such as fragrance and food flavor.

The characteristics of 2-Cyclohexen-1-ol,2-methyl-5-(1-methylethenyl)-, 1-acetate, (1R,5R)-rel- are as follows: (1)ACD/LogP: 3.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.52; (4)ACD/LogD (pH 7.4): 3.52; (5)ACD/BCF (pH 5.5): 279.37; (6)ACD/BCF (pH 7.4): 279.37; (7)ACD/KOC (pH 5.5): 1961.49; (8)ACD/KOC (pH 7.4): 1961.49; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Ų; (13)Index of Refraction: 1.474; (14)Molar Refractivity: 56.59 cm³; (15)Molar Volume: 201 cm³; (16)Polarizability: 22.43×10^-24cm³; (17)Surface Tension: 30.3 dyne/cm; (18)Density: 0.96 g/cm³; (19)Flash Point: 97.8 °C; (20)Enthalpy of Vaporization: 54.03 kJ/mol; (21)Boiling Point: 300.2 °C at 760 mmHg; (22)Vapour Pressure: 0.00114 mmHg at 25°C; (23)Exact Mass: 194.13068; (24)MonoIsotopic Mass: 194.13068; (25)Topological Polar Surface Area: 26.3; (26)Heavy Atom Count :14; (27)Complexity: 276; (28)Defined Atom StereoCenter Count: 2; (29)Covalently-Bonded Unit Count: 1; (30)Feature 3D Acceptor Count: 1; (31)Feature 3D Ring Count: 1.

Use of this chemical: 2-Cyclohexen-1-ol,2-methyl-5-(1-methylethenyl)-, 1-acetate, (1R,5R)-rel- could react with (benzhydrylidene-amino)-acetic acid methyl ester to produce cis methyl N-(diphenyl methylene)-2-carvenyl glycinate, and this reaction could happen in the reagent of LDA&dppe and the solvent of tetrahydrofuran with the catalyst of bis(dibenzylideneacetone)palladium(o) at the temperature of 25 °C, with the reaction time of 6 hours.

Production method of this chemical: Acetic acid anhydride could react with cis-(-)-carveol to produce 2-cyclohexen-1-ol,2-methyl-5-(1-methylethenyl)-, 1-acetate, (1R,5R)-rel-, and this reaction could happen in the reagent of DMAP and the solvent of CH₂Cl₂ with its yield of 98%.

What's more, the following datas could be converted into the molecular structure:
(1)Canonical SMILES: CC1=CCC(CC1OC(=O)C)C(=C)C
(2)Isomeric SMILES: CC1=CC[C@H](C[C@H]1OC(=O)C)C(=C)C
(3)InChI: InChI=1S/C12H18O2/c1-8(2)11-6-5-9(3)12(7-11)14-10(4)13/h5,11-12H,1,6-7H2,2-4H3/t11-,12-/m1/s1
(4)InChIKey: YTHRBOFHFYZBRJ-VXGBXAGGSA-N