Hydroxy-3-n-pentyl

Cannabis preparations in the form of marihuana, hashish, etc. have been known and used for many years for their psychoactive and therapeutic properties. The major active constituent of the resin which is exuded by the female plants of Cannabis sativa L. is (-)-6a,10a- rans-1 - hydroxy-3-n-pentyl-6,6,9-trimethyl-6a,7,8,l Oa-tetrahydr odibenzo[b,d]pyran, also known as (-)-6a,10a- rans-A-9-tetrahydrocan-nabinol or A9-THC. The structure and absolute configuration of this material was first reported by Gaoni et al. in J. Amer. Chem. Soc., 86, 1646 (1964). Since that time considerable research has been directed towards the preparation of this compound via a synthetic method, thereby eliminating the need to obtain the material by extraction from natural sources. 

A mixture of 153 mg (0.85 mmol) of olivetol, 132 mg (0.87 mmol) of (-i-)-cjs//rans-p-mentha-2,8-dien-l-ol and 200 mg of anhydrous magnesium sulfate in 5 mL of methylene chloride was stirred and cooled to ice bath temperature. Fifty microliters of anhydrous stannic chloride (0.111 g, 0.4 mmol) was added and stirring and cooling was continued. After 10 minutes, the reaction mixture was analyzed by gas-liquid chromatography and shown to contain 30 percent of (-)-6a,10a- rans-l-hydroxy-3-n-pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrodibenzo[b,d]pyran. After quenching the reaction with sodium carbonate, the desired compound can be isolated from the reaction mixture. 

Neofuscelia depsidella From 4-benzyloxy-2-hydroxy-6-n-pentyl-benzoic acid and 1,3-dihydroxy-5- -propylbenzene with DCCD and subsequent debenzylation (267)... 

By condensation of 2,4-dibenzyloxy-6-methylbenzoic acid and benzyl 4-benzyloxy-3-(2, 4 -dihydroxy-6 -methyl-benzoyloxy)-6-hydroxy-2-methylbenzoate with TFAA and subsequent debenzylation From 4-benzyloxy-2-hydroxy-6-/i-pentylbenzoic acid and olivetol with DCCD and subsequent debenzylation From 2-hydroxy-4-methoxy-6-n-propyl-benzoic acid and divarol with DCCD From 2-hydroxy-4-methoxy-6-n-propyl-henzoic acid and 3-methoxy-5-n-propylphenol with DCCD From 4-benzyloxy-2-hydroxy-6-n-pentyl-benzoic acid and 3-methoxy-5-n-propylphenol with DCCD and subsequent debenzylation... 

Deleting a cluster of 16 Vlr genes (2 of the 12 Vlr gene families representing about 12% of the Vlr repertoire) impairs sexual and maternal behavior. Gene-deficient male mice initiate fewer sexual encounters, and lactating females attack intruders less. Furthermore, both mutant male and female mice showed specific anosmia in that VNO did not respond to three of eight tested pheromonal compounds (6-hydroxy-6-methyl-3-heptanone, n-pentyl acetate, and isobutylamine) (Del Punta etal., 2002). 

A mixture of potassium hydroxide in methanol (300 ml) and water (5 mL) is added to [3aR-[3aa,4a(lE,3S),5p,6aa]]-5-(benzoyloxy)hexahydro-4-(3 -hydroxy-5-phenyl-l-pentyl)-2H-cyclopenta[b]furan-2-one. The mixture is stirred and heated in an 80°C for 2 hours. When the reaction is complete, the mixture is concentrated under reduced pressure. Water (100 mL) and MTBE (100 mL) are added and the mixture stirred at 20-25°C for 15 min. The phases are allowed to separate. The product is in the aqueous phase and the organic phase is removed. The pH of the aqueous phase is adjusted to 1 to 1.5 by the addition of hydrochloric acid (3 N, about 60 mL are required). The solution is stirred at 20-25°C. After 30 min, MTBE (100 mL) is added and the mixture stirred for 12 hours. The phases are separated and the aqueous phase extracted once with MTBE (50 mL). The MTBE phases are combined and washed with sodium carbonate (1 N, 50 mL). The MTBE mixture is stirred with a solution of potassium hydroxide (2.8 g, 42.5 mmole) in water (100 mL) for 30 min. The phases are separated and the aqueous phase is added to a slurry... 

The reaction of the formally dipole-stabilized carboanions with a variety of electrophiles gives 2,3-substituted thiiranes (Scheme 74). Ethyl jV,7V-dimethylthiocarbamate (209) undergoes lithiation to give (210), which readily reacts with benzaldehyde to give the thiirane (212) in 81% yield by way of the i -hydroxy adduct (211). The synthesis of thiirane (214) from n-pentyl-jV,jV-dimethyl-thiocarbamate (213) is shown in Equation (33) <82JOC3855>. 

Kennedy et al. used living cationic polymerization from a tricumyl initiator to prepare an allyl-terminated 3-arm star of pIB, followed by hydroboration/oxida-tion to generate hydroxy chain ends which were esterified with 2-bromoisobutyryl bromide to generate the ATRP trifunctional macroinitiator (Scheme 58) [354]. They subsequently carried out ATRP of MMA in toluene using the Cu(I)/N-( -pentyl)2-pyridylmethanimine catalyst system with the addition of Cu° powder [242] to maintain a sufficient concentration of active Cu(I) [354]. Macroinitiators of Mn=9200 and 15,000 were prepared and both had narrow molecular weight distributions (Mw/Mn=1.15 and 1.09, respectively). The formation of block copoly-... 

Di-t-pentyl-2-hydroxyphenyl)-2H-benzotriazole. See 2-(2 -Hydroxy-3,5 -di-t-amylphenyl) benzotriazole Dipentyl oxalate. See Diamyl oxalate N,N-Dipentyl-1-pentanamine. See Tri-n-amylamine... 

Hydroxy-4-methoxy-6-(3 -oxo-n-pentyl)-benzoic acid [2-Hydroxy-4-methoxy-6-(3 -oxo-n-pentyl)-benzoesaure]... 

From 2-hydroxy-4-methoxy-6-n-pentyl-benzoic acid and benzyl 4-hydroxy-2-methoxy-6-n-propylbenzoate with TFAA and subsequent debenzylation From 2,4-dimethoxy-6-n-pentylbenzoic acid and benzyl 4,6-dibenzyloxy-3-hydroxy-2-n-pentylbenzoate with TFAA and subsequent debenzylation From 2-n-heptyl-4,6-dimethoxybenzoic acid and benzyl 2,4-dihydroxy-6-n-pentylbenzoate with TFAA and subsequent debenzylation From 2- -heptyl-4-methoxy-6-hydroxy-benzoic acid and benzyl 2-O-methyl-olivetolcarboxylate with TFAA and subsequent debenzylation... 

The relative stereochemistry of hyperaspine 93 was determined by 2-D NMR spectroscopic and mass spectrometry (MS) methods. It has a m-fused bicyclic conformation 93a <2001TL4621>. The trans-fused one is disfavored by an axial pentyl group at C-8 and by a destabilizing dipole-dipole interaction between the N- and O-atoms, which does not exist in the alternative //.(-conformation. The geminal coupling constant of C( 1 )H2 in 93 (11.0 Hz), and that of its 6-hydroxy derivative (11.2 Hz), indicates that they exist preferentially in / //-conformations, whereas their 6-epimers adopt trans-conformations (9.3 and 8.4 Hz, respectively) <2005EJ01378>. Nuclear Overhauser enhancement spectroscopy (NOESY) studies also confirmed the stereochemistry of 93 by the marked nuclear Overhauser effect (NOE) correlation between H-3 and H-4a <20030L5063>. 

Chemical Name 1(2H)-Pyrimidineacetamide, N-((lS,3S,4S)-4-(((2,6-dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-l-(phenylmethyl) pentyl)tetrahyrdo-a-l-methylethyl)-2-oxo-, (aS)-... 

Following the examples of Schemes 2.5 and 2.7, the target may be synthesized from butyraldehyde as shown below. An altemative is radical addition of an enantiopure 2 hydroxy 1 pentyl group (perhaps from Jacobsen hydrolytic kinetic resolution of 1,2 epoxypentane,) to the N acylhydrazone derived from 5 chloropentanal. 

Rather surprisingly, if the hydroxy group is replaced by a halogen atom, elimination of HX (X = Cl or Br) appears to prefer a five-membered transition state (Equation 2.53). Deuterium-labeling studies with n-butyl and -pentyl chloride demonstrate that abstraction of the hydrogen from the y-carbon is the favored process. There are also indications that cyclic chlorides and bromides eliminate HX by the 1,3-mechanism. 

Di-t-butyl-4-hydroxybenzolc acid, n-hexadecyl ester 3,5-Di-t-butyl-4-hydroxyhydrocinnamic acid, 1,3,5-tris (2-hydroxyethyl)-s-triazine-2,4,6-(1H,3H,5H)-trione triester Dicetyl thiodipropionate Dicyandiamide Didodecyl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate Dimyristyl thiodipropionate p,p -Dioctyldiphenylamine 2,4-Di-t-pentyl-6-(1-(3,5-di-t-pentyl-2-hydroxyphenyl) ethyl) phenyl acrylate Distearyl pentaerythrityl diphosphite Drometrizole Ethylenebis (oxyethylene) bis (3-t-butyl-4-hydroxy-5-methylhydrocinnamate) 2,2 -Ethylidenebis (4,6-di-t-butylphenol) 2,2 -Ethylidenebis (4,6-di-t-butylphenyl) fluorophosphonite N,N -Hexamethylene bis (3,5-di-t-butyl-4-hydroxyhydrocinnamamide) Hexamethylenebis (3,5-di-t-butyl-4-hydroxycinnamate)... 

A soln. of (+)-(3R)-4-methyl-3-(tetrahydropyran-2-yloxy)pentane-l,4-diol in benzene added dropwise at room temp, under Ng to a stirred suspension of NaH in dry benzene, after 1.5 hrs. mesitoyl chloride in benzene added, and the product isolated after 6 hrs. at room temp. (+)-(3R)-4-hydroxy-4-methyl-3-(tetrahydropyran-2-yloxy)pentyl mesitoate. Y 80%. M. A. Abdallah and J. N. Shah, Soc. Perkin I 1975, 888. 

---