2-pentyloxirane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a manner similar to that of Example 1, condensation of 1-heptene oxide (52 g.) and 1,8-octanediamine (32.8 g.) and two recrystallizations of the resulting product from methanol gave N,N'-(1,8-octylene)-bis[2-hydroxyheptylamine] (I: R= CH3 (CH2)4, R' = H, X= (CH2)8, Z= H) (17.2 g., m.p. 128.0°-132.8° C.).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a manner similar to that of Example 1, condensation of 1-heptene oxide (52 g.) and 1,8-octanediamine (32.8 g.) and two recrystallizations of the resulting product from methanol gave N,N'-(1,8-octylene)-bis[2-hydroxyheptylamine] (I: R= CH3 (CH2)4, R' = H, X= (CH2)8, Z= H) (17.2 g., m.p. 128.0°-132.8° C.).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Condensation of 1-heptene oxide and 1,7-heptanediamine affords N,N'-(1,7-heptylene)-bis[2-hydroxyheptylamine] (I: R= CH3 (CH2)4, R' = H, X= (CH2)7, Z= H).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Condensation of 1-heptene oxide and 1,7-heptanediamine affords N,N'-(1,7-heptylene)-bis[2-hydroxyheptylamine] (I: R= CH3 (CH2)4, R' = H, X= (CH2)7, Z= H).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a manner similar to that of Example 1, condensation of 1-heptene oxide (71.8 g.) and hexamethylenediamine (32 g.) and recrystallization of the resulting product from ethanol gave N,N'-(1,6-hexylene)-bis[2-hydroxyheptylamine] (I: R= CH3 (CH2)4, R' = H, X= (CH2)6, Z= H) (16.5 g., m.p. 131.2°-134.2° C.).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1.14 g (10.0 mM) of (+)-1,2-epoxyheptane ([α]D +15.1° (neat)) in 5 ml of dry ether was quickly added dropwise into ice-cooled 2 ml of hydrogen fluoride/pyridine. After the addition, the mixture was stirred for 30 minutes in an ice bath, followed by addition of 10 ml of cold water and 3 times of extraction with 10 ml of ether. The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate, followed by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distiallation apparatus, to obtain 0.492 g of crude (-)-2-fluoroheptanol. Further, by repeating the above operations, 1.35 g of the crude product was obtained and rectified by means of a Claisen flask to obtain 0.80 g (600 mM) of objective (-)-2-fluoroheptanol. Yield: 20.0%. The product showed the following properties: After the addition The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distiallation apparatus

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1.14 g (10.0 mM) of (+)-1,2-epoxyheptane ([α]D +15.1° (neat)) in 5 ml of dry ether was quickly added dropwise into ice-cooled 2 ml of hydrogen fluoride/pyridine. After the addition, the mixture was stirred for 30 minutes in an ice bath, followed by addition of 10 ml of cold water and 3 times of extraction with 10 ml of ether. The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate, followed by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distiallation apparatus, to obtain 0.492 g of crude (-)-2-fluoroheptanol. Further, by repeating the above operations, 1.35 g of the crude product was obtained and rectified by means of a Claisen flask to obtain 0.80 g (600 mM) of objective (-)-2-fluoroheptanol. Yield: 20.0%. The product showed the following properties: After the addition The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distiallation apparatus

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1.14 g (10.0 mM) of (+)-1,2-epoxyheptane ([α]D +15.1° (neat)) in 5 ml of dry ether was quickly added dropwise into ice-cooled 2 ml of hydrogen fluoride/pyridine. After the addition, the mixture was stirred for 30 minutes in an ice bath, followed by addition of 10 ml of cold water and 3 times of extraction with 10 ml of ether. The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate, followed by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distiallation apparatus, to obtain 0.492 g of crude (-)-2-fluoroheptanol. Further, by repeating the above operations, 1.35 g of the crude product was obtained and rectified by means of a Claisen flask to obtain 0.80 g (600 mM) of objective (-)-2-fluoroheptanol. Yield: 20.0%. The product showed the following properties: After the addition The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distiallation apparatus

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1.14 g (10.0 mM) of (+)-1,2-epoxyheptane ([α]D +15.1° (neat)) in 5 ml of dry ether was quickly added dropwise into ice-cooled 2 ml of hydrogen fluoride/pyridine. After the addition, the mixture was stirred for 30 minutes in an ice bath, followed by addition of 10 ml of cold water and 3 times of extraction with 10 ml of ether. The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate, followed by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distillation apparatus, to obtain 0.492 g of crude (-)-2-fluoroheptanol. Further, by repeating the above operations, 1.35 g of the crude product was obtained and rectified by means of a Claisen flask to obtain 0.80 g (600 mM) of objective (-)-2-fluoroheptanol. Yield: 20.0%. The product showed the following properties: After the addition The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distillation apparatus

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1.14 g (10.0 mM) of (+)-1,2-epoxyheptane ([α]D +15.1° (neat)) in 5 ml of dry ether was quickly added dropwise into ice-cooled 2 ml of hydrogen fluoride/pyridine. After the addition, the mixture was stirred for 30 minutes in an ice bath, followed by addition of 10 ml of cold water and 3 times of extraction with 10 ml of ether. The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate, followed by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distillation apparatus, to obtain 0.492 g of crude (-)-2-fluoroheptanol. Further, by repeating the above operations, 1.35 g of the crude product was obtained and rectified by means of a Claisen flask to obtain 0.80 g (600 mM) of objective (-)-2-fluoroheptanol. Yield: 20.0%. The product showed the following properties: After the addition The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distillation apparatus

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a manner similar to that of Example 1, condensation of 1-heptene oxide (52 g.) and 1,8-octanediamine (32.8 g.) and two recrystallizations of the resulting product from methanol gave N,N'-(1,8-octylene)-bis[2-hydroxyheptylamine] (I: R = CH3 (CH2)4, R' = H, X = (CH2)8, Z = H) (17.2 g., m.p. 128.0°-132.8° C.).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Condensation of 1-heptene oxide and 1,7-heptanediamine affords N,N'-(1,7-heptylene)-bis [2-hydroxyheptylamine] (I: R = CH3 (CH2)4, R' = H, X = (CH2)7, Z = H).