7-(3-((2-((Phenylamino)carbonyl)hydrazino)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)-5-heptenoic acid

Base Information

• Chemical Name: 7-(3-((2-((Phenylamino)carbonyl)hydrazino)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)-5-heptenoic acid
• CAS No.: 98299-61-7
• Molecular Formula: C₂₁H₂₉N₃O₄
• Molecular Weight: 387.479
• Nikkaji Number: J23.712D
• Wikidata: Q27088857
• Pharos Ligand ID: D8698PHS5D42
• Mol file: 98299-61-7.mol

Synonyms:7-(3-((2-((phenylamino)carbonyl)hydrazino)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)-5-heptenoic acid;SQ 26538;SQ 28053;SQ 29548;SQ-26,538;SQ-26538;SQ-28053;SQ-29548;SQ26,538;SQ26538

Chemical Property of 7-(3-((2-((Phenylamino)carbonyl)hydrazino)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)-5-heptenoic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: °C
• PSA: 99.69000
• Density: 1.207 g/cm³
• LogP: 4.16230
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 387.21580641
• Heavy Atom Count: 28
• Complexity: 548

Purity/Quality:

99% ^*data from raw suppliers

SQ 29,548 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(C(C1O2)CC=CCCCC(=O)O)CNNC(=O)NC3=CC=CC=C3
• Isomeric SMILES: C1C[C@H]2[C@H]([C@H]([C@@H]1O2)C/C=C\CCCC(=O)O)CNNC(=O)NC3=CC=CC=C3
• Uses: SQ-29548 is a potent and selective thromboxane A2 receptor antagonist.

Technology Process of 7-(3-((2-((Phenylamino)carbonyl)hydrazino)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)-5-heptenoic acid

There total 4 articles about 7-(3-((2-((Phenylamino)carbonyl)hydrazino)methyl)-7-oxabicyclo(2.2.1)hept-2-yl)-5-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:

C22H31N3O4 (128781-29-3) → <1α,2α(Z),3α,4α>-7-<3-<<2-<(phenylamino)carbonyl>hydrazino>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (98299-61-7,98672-91-4,125224-12-6,128821-47-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 2h; Yield given; Ambient temperature;

DOI:10.1021/jm00171a021

Reference yield:

methyl <1α,2α(Z),3α,4α>-7-<3-formyl-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate (104596-33-0) → <1α,2α(Z),3α,4α>-7-<3-<<2-<(phenylamino)carbonyl>hydrazino>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (98299-61-7,98672-91-4,125224-12-6,128821-47-6)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / 6 h / Ambient temperature

2: NaBH₃CN, glacial AcOH / methanol / Ambient temperature; pH 3-3.5

3: aq. 1 N LiOH / tetrahydrofuran / 2 h / Ambient temperature

With lithium hydroxide; sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol;

DOI:10.1021/jm00171a021

Reference yield:

C22H29N3O4 (128781-28-2,128821-63-6) → <1α,2α(Z),3α,4α>-7-<3-<<2-<(phenylamino)carbonyl>hydrazino>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (98299-61-7,98672-91-4,125224-12-6,128821-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₃CN, glacial AcOH / methanol / Ambient temperature; pH 3-3.5

2: aq. 1 N LiOH / tetrahydrofuran / 2 h / Ambient temperature

With lithium hydroxide; sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol;

DOI:10.1021/jm00171a021

upstream raw materials:

C₂₂H₃₁N₃O₄

methyl <1α,2α(Z),3α,4α>-7-<3-formyl-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

C₂₂H₂₉N₃O₄

4-phenyl-semicarbazide

Refernces