(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol Chemical Properties

Boiling point:

69-70 °C(Press: 3 Torr)

Density 

0.9398

Flash point:

87.0±19.6 °C

storage temp. 

2-8°C

solubility 

Chloroform (Soluble), Methanol (Soluble)

pka

14.66±0.40(Predicted)

form 

Oil

color 

Colourless

optical activity

-0.11° (C=1.00 g/100ml, CHCL3)

Water Solubility 

4.2g/L

Stability:

Light Sensitive

InChI

InChI=1S/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3/t9-,10+/m0/s1

InChIKey

MKPMHJQMNACGDI-VHSXEESVSA-N

SMILES

[C@@]1(C)(O)CC[C@@H](C(C)=C)C=C1

LogP

2.82

Safety Information

HS Code 

2906190090

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol Usage And Synthesis

Uses

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol is an acetal reagent used in the synthesis of desoxy cannabidiols and THC (T293202) related psychoactive compounds. It is formed from (+)-Limonene using a photosynthesized O2 transfer.

Definition

ChEBI: (1S,4R)-p-Mentha-2,8-dien-1-ol is a p-menthane monoterpenoid.

Hazard

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol causes skin irritation and serious eye irritation. It may cause respiratory irritation.

Synthesis

The 1S,2S,5R-N,N,2-trimethyl-2-hydroxy-5-isopropenylcyclohexylamine oxide (1.430 g, 6.7 mmol) was heated in a Kugelrohr oven at 180 °C under 1 mmHg vacuum until the solid residue completely disappeared. The yellow distillate (1.317 g) was collected and purified by fast chromatography (ether:hexane=2:3) to afford the target product (1S,4R)-1-methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol (0.752 g, 74% yield) as a colorless oil. the Rf value was 0.32 (ether:hexane=2:3); the specific optical rotation [α]D26: +60 (c=1.0, CHCl3), consistent with literature value [α]D23: +53.8 (CHCl3); IR spectrum (SeZn) showed absorption peaks: 3354 (medium, broad, O-H), 2967 (medium, C-H), 2935 (medium, CH), 2861 (medium, CH), 1644 (medium, C=C), 1105 (strong, CO), and 888 (strong, C=CH bent), 736 (strong, C=CH bent) cm-1; 1H NMR (500 MHz, CDCl3) chemical shift: δ 5.70 (1H, ddd, 3JH2-H3=10.0 Hz, 4JH2-H4=2.4 Hz, 4JH2-H6=1.4 Hz, H2), 5.65 (1H, ddd. 3JH3-H2=10.0 Hz, 3JH3-H4=2.4 Hz, 4JH3-H5=0.8 Hz, H3), 4.78 (1H, quin, 4JH9b-H10≈4JH9b-H4=1.6 Hz, H9b), 4.74 (1H, quin, 4JH9a-H10≈4JH9a-H4=0.88 Hz, H9a), 2.65 (1H, m, H4), 1.88-1.73 (2H, m, H5eq, H6eq), 1.73 (3H, s, H10), 1.66-1.51 (3H, m, H5ax, H6ax, OH), 1.29 (3H, s, H7) ppm; 13C NMR (125 MHz, CDCl3) chemical shift : 148.3 (C8), 134.1 (C2), 132.3 (C3), 110.7 (C9), 67.6 (C1), 43.6 (C4), 36.9 (C6), 29.6 (C7), 25.0 (C5), 21.0 (C10) ppm; low resolution mass spectra (GC-MS): m/z 152 (M+, 2%), 134 ( [M-H2O]+, 11%), 119 ([M-CH3-H2O]+, 32%), 91 (100%), 79 (37%), 77 (46%); Elemental analysis (C10H16O) Calculated values: C 78.90, H 10.59; Measured values: C 78.25, H 10.59, N < 0.05.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 1, p. 52 - 54

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol(22972-51-6)Related Product Information

• trans-4-Aminocyclohexanemethanol
• N,N-DIETHYLBENZAMIDE
• 2-Methylindole
• Adenosine
• 3-METHYLSTYRENE
• VINYL PROPIONATE
• Methoxyethene
• (1R)-(+)-TRANS-ISOLIMONENE
• (4R)-1-METHYL-4-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-OL
• (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol