Pentyl compounds

The 6-(N-methyl-2-acetamido)ethylamino derivative. Presumably the n-pentyl compound. 

It is especially interesting that the duration of action of the propyl cannabinoids is significantly shorter than that of the pentyl compounds. Smoking marijuana with large amounts of THCV should produce a shorter high than usual, but human ex-... 

TABLE 10.5 Dependence of Elimination Products on Leaving Group in Elimination of HL from 2-Pentyl Compounds ... 

Table 2 gives the thermal and analytical properties of the series of p-alkylphenyl esters of 1,4-cyclohexanedlcarboxyllc acid. Four members of this series were prepared In which the alkyl group was varied from ethyl through n-pentyl. The first two members, the ethyl and propyl substituted compounds, have straightforward thermal transitions, both showing only enantlotropic nematic mesophases. A smectic phase first appears In the n-butyl member and the butyl and pentyl compounds are both smectic and nematic. The solids In this series are less complex than In the alkoxy series, and there Is no Indication of solid polymorphism. The n-pentyl does become more complex In Its mesophase and three smectics are observed, two of which are monotropic. The transition temperatures of these are too close to allow resolution of the peaks on the DSC, and no determination of the separate heats was made. 

The results of such solubility measurements at 310 K and up to about 20 MPa on the methyl, ethyl, propyl, butyl, pentyl, and octyl derivatives are presented in Fig. 28. The solubilities increase with increasing pressure. It should, however, be mentioned here that such curves can also run through inflexion points, and even extreme values may occur [42,45,46,76,77]. It is remarkable that according to Fig. 28 not only the octyl compound but also the methyl and ethyl derivatives are less soluble than the butyl and pentyl compounds. This unexpected effect has... 

Reactions of Sulphones.—The first report of pyrolytic elimination of aryl-sulphinic acid from an aryl alkyl sulphone has appeared, for 2-pentyl compounds these give pent-l-ene in constant proportion with cis- and t/ /i5-pent-2-ene, with exceptions for mesityl and p-nitrophenyl 2-pentyl sulphones. Base-catalysed elimination reactions leading to vinyl sulphones are well known, amine-promoted elimination from PhSOzCHa CHF-SPh following a jy/i-stereospecific course through an Elcb mechanism involving ion-pairs. A mild decarbomethoxylative elimination is the last step in a synthesis of ( )-versimide (131). ... 

Pyrolysis of the 1-pentyl and 3-pentyl structures shows that in the former case although the 1-ene is the main product, a considerable amount of double bond migration to the 2 position occurs. With the 3-pentyl compound, over 90% of the product appears as pentene-2, only 7.7% pentene-1 being observed. 

The prefix tert can be used for both r rt-butyl and f rf-pentyl compounds because each of these substituent names describes only one alkyl group. The name f rf-hexyl cannot be used because it describes two different alkyl groups. 

Titanium(IV) is a powerful but selective Lewis acid which can promote the coupling of allylsilanes with carbonyl compounds and derivatives In the presence of titanium tetrachlonde, benzalacetone reacts with allyltnmethylsilane by 1,4-addition to give 4-PHENYL-6-HEPTEN-2-ONE. Similarly, the enol silyl ether of cyclopentanone is coupled with f-pentyl chloride using titanium tetrachlonde to give 2-(tert-PENTYL)CYCLOPENTANONE, an example of a-tert-alkylation of ketones. 

Bridgeheads. The Sn2 mechanism is impossible at most bridgehead compounds (p. 392). Nucleophilic attack in [l.l.l]propellane has been reported, however. In general, a relatively large ring is required for an SnI reaction to take place (p. 396). " The SnI reactions have been claimed to occur for l-iodobicyclo[l.l.l]pentane via the bicyclo[l.l.l]pentyl cation, but this has been disputed and the bicyclo[1.1.0]butyl carbinyl cation was... 

Structure of 4-cyano-4 -n-pentyl-p-terphenyl (T15) is shown in Fig. 12. This compound, first prepared by Gray et al. [82], exhibits a nematic phase with a wide temperature range. 

Mandal et al. [89-91] investigated the crystal structures of three members of the homologous series of 5-(4 -n-alkylcyclohexyl)-2-(4"-cyanophenyl)-pyrimi-dines. The crystal structures of the ethyl (ECCPP), pentyl (PCCPP), and heptyl (HCCPP) compounds were determined. The chemical structure of the compounds is presented in Fig. 15. The two lower homologues possess only a nematic phase, while the heptyl compound has a smectic phase in addition to a nematic phase. 

The lUPAC name of cannabidiol is 2-[(lS, 6iI)-3-methyl-6-prop-l-en-2-yl-l-cyclohex-2-enyl]-5-pentyl-benzene-1,3-diol. Cannabidiol (CBD, 2.9) in its acidic form cannabidiolic acid (CBDA, 2.10) is the second major cannabinoid in C. sativa besides A9-THC. As already mentioned for A9-THC, variations in the length of the side chain are also possible for CBD. Important in this context are the propyl side chain-substituted CBD, named cannabidivarin (CBDV, 2.11), and CBD-C4 (2.12), the homologous compound with a butyl side chain. Related to the synthesis starting from CBD to A9-THC as described in Sect. 3.1, it was accepted that CBDA serves as a precursor for THCA in the biosynthesis. Recent publications indicate that CBDA and THCA are formed from the same precursor, cannabigerolic acid (CBGA), and that it is unlikely that the biosynthesis of THCA from CBDA takes place in C. sativa. 

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