1,7-Heptanediol

de Oliveira, Adeildo Junior, et al. ChemistrySelect 4.36 (2019): 10843-10845.

Different conditions for the monobromination of α,ω-diols using HBr were tested. Three solvents were tested, toluene, isooctane, 1,2-dichloroethane, at two different molar ratios (1:1 and 1:2 equiv.) between 1,8-octanediol and HBr. All reactions were performed under reflux. After determining the optimal reaction conditions, assay reactions were performed with 1,6-hexanediol; 1,7-heptanediol; 1,8-octanediol; and 1,10-decanediol. The best reaction yields (81-95%) were obtained using toluene as solvent, with the least amount of unwanted dibrominated products produced. When HBr was used, reactions in 1,2-dichloroethane produced similar results to those with toluene. The lowest reaction efficiency recorded in these assays occurred in isooctane, with the highest amount of dibromide formed. The diols 1,7-heptanediol and 1,8-octanediol showed the best results in 1,2-dichloroethane under the conditions studied.
1,7-Heptanediol (6.7 mmol), HBr (6.7 mmol for 1 eq., 13.4 mmol for 2 eq.), 20 mL solvent, reflux for 2 h. The HBr molar equivalents were determined with reference to the diol. The ratio (%) between the mono- and di-bromo products formed in these experiments was determined by GC-MS.

Stefanello, Sílvio Terra, et al. Advanced NanoBiomed Research 2.9 (2022): 2200050.

Non-small cell lung cancer (NSCLC) accounts for the vast majority of its histological subtypes, and the survival rate of patients in the advanced stage is extremely low. Recent studies have shown that certain compounds, such as diols, are able to inhibit the migration and reduce the viability of highly metastatic NSCLC cells A549_3R. Some diols were tested for their ability to acutely impair the bioenergetics, metabolism, and viability of A549_3R cells. The results showed that 1,5-pentanediol (1,5-PD), 1,6-hexanediol (1,6-HD), and 1,7-heptanediol (1,7Hept) were the most effective. They interfere with key enzymes in glycolysis and trigger most or all of the following reactions: acute collapse of the key mitochondrial membrane potential, a significant decrease in ATP, pyruvate, and L-lactate levels, and a significant increase in the production of reactive oxygen species. Therefore, these potent sugar compounds may be promising anticancer compounds or leads for local and intratumoral applications.
The Warburg effect utilizes LDH-A to generate ATP in aerobic glycolysis by converting pyruvate and NADH to lactate and NADin, the final step of glycolysis. 1,5-pentanediol (1,5-PD), 1,6-hexanediol (1,6-HD), and 1,7-heptanediol (1,7Hept) were tested to affect the levels of these reactants and products in A549_3R cells. Bioenergetic metabolite levels were measured in A549_3R cells after 1 h exposure to 2% (v/v) 1,6-HD, 1,5-PD, and 1,7-Hept. Data were collected for ATP production, lactate production, pyruvate, NAD/NADH ratio, NADH, and NAD reactions. Data are shown as mean SEM of four separate experiments.

Abe, Katsutoshi, et al. Catalysis Today 164.1 (2011): 419-424.

The gas-phase catalytic reaction of several terminal diols on several rare earth oxides was studied. Sc2O3 showed selective catalytic activity in the dehydration of terminal diols with long carbon chains, such as 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, and 1,12-dodecanediol, to produce the corresponding unsaturated alcohols. In the dehydration of 1,6-hexanediol, 5-hexen-1-ol was produced with a selectivity of more than 60 mol% as well as by-products such as -caprolactone and oxepane. In the dehydration of 1,10-decanediol, 9-decen-1-ol was produced with a selectivity of more than 70 mol%. In addition to ScO, heavy rare earth oxides such as LuO as well as monoclinic ZrO showed moderate selectivity in the dehydration of terminal diols.
The catalytic reactions were carried out in a fixed-bed reactor. Before the reaction, the catalyst sample was preheated at 500 °C for 1 h in the flow reactor. After setting the temperature of the catalyst bed at a specified temperature between 325 and 425 °C, a liquid feed rate F of 1.80 cm^3·h^-1 and a flow rate of 27 cm^3·min^-1 were passed through the top of the reactor. A diol such as 1,7-heptanediol dissolved at 20 wt.% in ethanol was used as the reactant solution. The effluent collected every hour was analyzed by gas chromatography and mass spectrometry using a flame ionization detector and a 30 m capillary column.

Mhaskar, S. Y., and R. Subbarao. Society 70 (1993): 519-522.

A method for the synthesis of 7,10-dibenzoyloxy-8(E)-octadecenoic acid from 1,7-heptanediol is reported. One hydroxyl group of 1,7-heptanediol is protected as a tetrahydropyranyl ether, and the other hydroxyl group is chain-extended through two carbon atoms by Wittig reaction to give ethyl 9-tetrahydropyranyloxy-2(E)-nonenoate, an α,β-unsaturated ester that is reduced by Dibal-H to give the allylic alcohol. After double bond epoxidation, the hydroxyl group is converted to chlorine to give 9-tetrahydropyranyloxy-2,3-epoxypropane-1-chloro-nonane. The epoxynonyl chloride is treated with excess LiNH2/liquid NH3 followed by the addition of 1-nonanal to give 18-tetrahydropyranyloxy-9,12-dihydroxy-10-octadecyne. The conjugated hydroxyl-alkyne bond was reduced with lithium aluminum hydride, the hydroxyl group was protected as benzoate, and the primary ether group was oxidized, followed by removal of the benzoate group to give DOD.
1,7-Heptanediol and PTSA were dissolved in 200 mL of DCM and cooled to 0°C. Dihydropyran was added dropwise over 15 minutes. After removing DCM using a rotary evaporator, the crude product was extracted with ether and purified on a silica gel column to give 75% of 7-tetrahydropyranyloxy-1-heptanol. This compound was dissolved in anhydrous DCM (150 mL) and cooled to 0°C.