2-((3-((((Phenylamino)carbonyl)hydrazono)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)methyl)benzenepropanoic acid

Base Information

• Chemical Name: 2-((3-((((Phenylamino)carbonyl)hydrazono)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)methyl)benzenepropanoic acid
• CAS No.: 135613-36-4
• Molecular Formula: C24H27N3O4
• Molecular Weight: 421.4889
• DSSTox Substance ID: DTXSID301103278
• Mol file: 135613-36-4.mol

Synonyms:2-((3-((((phenylamino)carbonyl)hydrazono)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)methyl)benzenepropanoic acid;SQ 35,091;SQ 35091;SQ-35091

Chemical Property of 2-((3-((((Phenylamino)carbonyl)hydrazono)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)methyl)benzenepropanoic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.32g/cm³
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 421.20015635
• Heavy Atom Count: 31
• Complexity: 649

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(C(C1O2)CC3=CC=CC=C3CCC(=O)O)C=NNC(=O)NC4=CC=CC=C4
• Isomeric SMILES: C1C[C@@H]2[C@H]([C@H]([C@H]1O2)CC3=CC=CC=C3CCC(=O)O)/C=N/NC(=O)NC4=CC=CC=C4

Technology Process of 2-((3-((((Phenylamino)carbonyl)hydrazono)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)methyl)benzenepropanoic acid

There total 13 articles about 2-((3-((((Phenylamino)carbonyl)hydrazono)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)methyl)benzenepropanoic 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: 53.0%

C25H29N3O4 (135613-50-2,135682-57-4) → syn-<1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid (135682-58-5) + anti-<1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid (135613-36-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1021/jm00113a030

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → anti-<1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid (135613-36-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 98 percent / tetrahydrofuran / 18 h / 25 °C

2: 97 percent / H₂ / 5percent Rh/Al₂O₃ / methanol / 3 h

3: 100 percent / diisobutylaluminum hydride / toluene / 1.) -78 deg C, 2 h, 2.) from -78 deg C to 0 deg C, 2 h

4: 92 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 4 h / 25 °C

5: 1.) tert-butyllithium / 1.) ether, pentane, a) -100 deg C, 15 min, b) 0 deg C, 15 min, 2.) ether, pentane, THF, 0 deg C, 1 h

6: 55 percent / H₂, glacial HOAc / 20percent Pd(OH)2/C / 5 h / 760 Torr

7: 4-(dimethylamino)pyridine, pyridine / 2 h / 25 °C

8: CrO₃, H₂SO₄ / acetone / 2 h / 0 °C

9: 1 M aq. NaOH / tetrahydrofuran / 0.5 h / 25 °C

10: HCl / 2 h / 0 °C

11: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 25 °C

12: 92 percent / methanol / 40 h / 25 °C

13: 53 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 3 h / 25 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; palladium dihydroxide; Rh/Al₂O₃; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene;

DOI:10.1021/jm00113a030

Reference yield:

3-(2-bromophenyl)propanoic acid,methyl ester (66191-86-4) → anti-<1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid (135613-36-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / diisobutylaluminum hydride / toluene / 1.) -78 deg C, 2 h, 2.) from -78 deg C to 0 deg C, 2 h

2: 92 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 4 h / 25 °C

3: 1.) tert-butyllithium / 1.) ether, pentane, a) -100 deg C, 15 min, b) 0 deg C, 15 min, 2.) ether, pentane, THF, 0 deg C, 1 h

4: 55 percent / H₂, glacial HOAc / 20percent Pd(OH)2/C / 5 h / 760 Torr

5: 4-(dimethylamino)pyridine, pyridine / 2 h / 25 °C

6: CrO₃, H₂SO₄ / acetone / 2 h / 0 °C

7: 1 M aq. NaOH / tetrahydrofuran / 0.5 h / 25 °C

8: HCl / 2 h / 0 °C

9: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 25 °C

10: 92 percent / methanol / 40 h / 25 °C

11: 53 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 3 h / 25 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene;

DOI:10.1021/jm00113a030

upstream raw materials:

C₂₅H₂₉N₃O₄

(1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

ortho-bromobenzaldehyde

3-(2-bromophenyl)propanoic acid,methyl ester

Refernces