7-<3α-<1-<<(phenylamino)thioxomethyl>hydrazono>ethyl>-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl>-5(Z)-heptenoic acid

Base Information

• Chemical Name: 7-<3α-<1-<<(phenylamino)thioxomethyl>hydrazono>ethyl>-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl>-5(Z)-heptenoic acid
• CAS No.: 129569-49-9
• Molecular Formula: C₂₃H₃₁N₃O₂S
• Molecular Weight: 413.584

Synonyms:7-<3α-<1-<<(phenylamino)thioxomethyl>hydrazono>ethyl>-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl>-5(Z)-heptenoic acid

Chemical Property of 7-<3α-<1-<<(phenylamino)thioxomethyl>hydrazono>ethyl>-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl>-5(Z)-heptenoic acid

Chemical Property:

Purity/Quality:

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Technology Process of 7-<3α-<1-<<(phenylamino)thioxomethyl>hydrazono>ethyl>-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl>-5(Z)-heptenoic acid

There total 17 articles about 7-<3α-<1-<<(phenylamino)thioxomethyl>hydrazono>ethyl>-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl>-5(Z)-heptenoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

7-(3α-acetyl-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl)-5(Z)-heptenoic acid (129569-45-5) + 4-Phenyl-3-thiosemicarbazide (5351-69-9) → 7-<3α-<1-<<(phenylamino)thioxomethyl>hydrazono>ethyl>-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl>-5(Z)-heptenoic acid (129569-49-9)

Guidance literature:

With pyridine; for 20h; Ambient temperature;

DOI:10.1021/jo00310a017

Reference yield:

(1R,2S,6R,7S)-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one (105500-35-4) → 7-<3α-<1-<<(phenylamino)thioxomethyl>hydrazono>ethyl>-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl>-5(Z)-heptenoic acid (129569-49-9)

Guidance literature:

Multi-step reaction with 10 steps

1: hydrogen / W-2 Raney nickel / tetrahydrofuran / 2 h / 25 °C / 760 Torr

2: lithium cyclohexylisopropylamide / 1) THF, hexane, -78 deg C, 2 h; 2) 0 deg C, 16 h

3: lithium dimethylcuprate / 1) Et₂O, -20 deg C, 20 h, 2) Et₂O, -20 to 20 deg C

4: sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide / 1) THF, room temp., 3 h; 2) room temp., 45 min

5: jones reagent / acetone

6: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 120 h / Ambient temperature

7: diisobutylaluminium hydride / toluene / 4 h / -78 °C

8: sodium hexamethyldisilazane / 1) THF, RT, 18 h; 2) THF, 4 h at 0 deg C, then 20 h at room temp.

9: jones reagent / acetone

10: pyridine / 22 h / Ambient temperature

With pyridine; sodium hydroxide; jones reagent; dimethylsulfide borane complex; lithium dimethylcuprate; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; lithium cyclohexylisopropylamide; 3-chloro-benzenecarboperoxoic acid; W-2 Raney nickel; In tetrahydrofuran; dichloromethane; acetone; toluene;

DOI:10.1021/jo00310a017

Reference yield:

(1aR)-1aα,1bβ,2,5,5aβ,6aα-hexahydro-2β,5β-methano-6H-indeno<1,2-b>oxiren-6-one (129569-63-7) → 7-<3α-<1-<<(phenylamino)thioxomethyl>hydrazono>ethyl>-(1R,1α,4α)-bicyclo<2.2.1>hept-2β-yl>-5(Z)-heptenoic acid (129569-49-9)

Guidance literature:

Multi-step reaction with 12 steps

1: hydrazine hydrate; acetic acid / methanol

2: jones reagent / acetone / -10 °C

3: hydrogen / W-2 Raney nickel / tetrahydrofuran / 2 h / 25 °C / 760 Torr

4: lithium cyclohexylisopropylamide / 1) THF, hexane, -78 deg C, 2 h; 2) 0 deg C, 16 h

5: lithium dimethylcuprate / 1) Et₂O, -20 deg C, 20 h, 2) Et₂O, -20 to 20 deg C

6: sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide / 1) THF, room temp., 3 h; 2) room temp., 45 min

7: jones reagent / acetone

8: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 120 h / Ambient temperature

9: diisobutylaluminium hydride / toluene / 4 h / -78 °C

10: sodium hexamethyldisilazane / 1) THF, RT, 18 h; 2) THF, 4 h at 0 deg C, then 20 h at room temp.

11: jones reagent / acetone

12: pyridine / 22 h / Ambient temperature

With pyridine; sodium hydroxide; jones reagent; dimethylsulfide borane complex; lithium dimethylcuprate; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; lithium cyclohexylisopropylamide; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; W-2 Raney nickel; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

DOI:10.1021/jo00310a017

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

(3aα,7aα)-octahydro-(1R)-1α-methyl-4α,7α-methano-2H-inden-2-one

4-Phenyl-3-thiosemicarbazide

(3aα,7aα)-octahydro-(1S)-1α-methyl-4α,7α-methano-2H-inden-2-one

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