Endiandric acid B

Base Information

• Chemical Name: Endiandric acid B
• CAS No.: 76060-33-8
• Molecular Formula: C23H24O2
• Molecular Weight: 332.4355
• UNII: HAH2NZP9F9
• Wikidata: Q27279827
• Mol file: 76060-33-8.mol

Synonyms:Endiandric acid B;Endiandric acid B [MI];HAH2NZP9F9;76060-33-8;2-Butenoic acid, 4-((1R,1aS,3aS,4S,6aR,7aR,7bR,7cr)-1a,3a,4,6a,7,7a,7b,7c-octahydro-4-phenyl-1H-cyclobut(bc)acenaphthylen-1-yl)-, (2E)-rel-;Rel-(2E)-4-((1R,1aS,3aS,4S,6aR,7aR,7bR,7cr)-1a,3a,4,6a,7,7a,7b,7c-octahydro-4-phenyl-1H-cyclobut(bc)acenaphthylen-1-yl)-2-butenoic acid;UNII-HAH2NZP9F9;SCHEMBL3200662;2-Butenoic acid, 4-(1a,2,2a,5,5a,7a,7b,7c-octahydro-5-phenyl-1H-cyclobut(bc)acenaphthylen-1-yl)-, (1alpha(E),1aalpha,2abeta,5alpha,5aalpha,7aalpha,7balpha,7calpha)-(+/-)-;Q27279827;2-BUTENOIC ACID, 4-(1A,2,2A,5,5A,7A,7B,7C-OCTAHYDRO-5-PHENYL-1H-CYCLOBUT(BC)ACENAPHTHYLEN-1-YL)-, (1.ALPHA.(E),1A.ALPHA.,2A.BETA.,5.ALPHA.,5A.ALPHA.,7A.ALPHA.,7B.ALPHA.,7C.ALPHA.)-(+/-)-

Chemical Property of Endiandric acid B

Chemical Property:

• Vapor Pressure: 5.44E-11mmHg at 25°C
• Boiling Point: 504.3°Cat760mmHg
• Flash Point: 384.9°C
• Density: 1.173g/cm³
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 332.177630004
• Heavy Atom Count: 25
• Complexity: 624

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC(C3C2C4C1C(C4C=C3)CC=CC(=O)O)C5=CC=CC=C5
• Isomeric SMILES: C1[C@H]2C=C[C@H]([C@H]3[C@@H]2[C@H]4[C@@H]1[C@@H]([C@H]4C=C3)C/C=C/C(=O)O)C5=CC=CC=C5

Technology Process of Endiandric acid B

There total 6 articles about Endiandric acid B 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: 100.0%

endiandric acid B methyl ester (82730-19-6) → endiandric acid B (76060-33-8)

Guidance literature:

alkaline hydrolysis;

DOI:10.1021/ja00384a077

Reference yield:

(1S,1aR,2aS,5R,5aR,7aS,7bS,7cS)-1-Bromomethyl-5-phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylene (82679-79-6) → endiandric acid B (76060-33-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / hexamethylphosphoric acid triamide / 25 °C

2: 1.) Dibal / 1.) CH₂Cl₂, -78 deg C, 2.) acid

3: NaH

4: 100 percent / alkaline hydrolysis

With sodium hydride; diisobutylaluminium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/ja00384a077

Reference yield:

((1S,1aR,2aS,5R,5aR,7aS,7bS,7cS)-5-Phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-yl)-methanol (82679-78-5) → endiandric acid B (76060-33-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / CBr₄, Ph₃P / CH₂Cl₂ / 0 °C

2: 98 percent / hexamethylphosphoric acid triamide / 25 °C

3: 1.) Dibal / 1.) CH₂Cl₂, -78 deg C, 2.) acid

4: NaH

5: 100 percent / alkaline hydrolysis

With carbon tetrabromide; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1021/ja00384a077

upstream raw materials:

endiandric acid B methyl ester

((1S,1aS,2aS,5R,5aR,7aR,7bS,7cS)-5-Phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-yl)-acetaldehyde

(1S,1aR,2aS,5R,5aR,7aS,7bS,7cS)-1-Bromomethyl-5-phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylene

((1S,1aR,2aS,5R,5aR,7aS,7bS,7cS)-5-Phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-yl)-methanol

Downstream raw materials:

endiandric acid B methyl ester

methyl (E)-4-(6'-phenyltetracyclo<5,4,2,0^3.13,0^10.12>trideca-4',8'-dien-11-yl)but-2-enoate

3-hydroxyamino (E)-4-(6'-phenyltetracyclo<5,4,2,0^3.13,0^10.12>trideca-4',8'-dien-11'-yl)butanoic acid

4-(6'-phenyltetracyclo<5,4,2,0^3.13,0^10.12>tridec-11'-yl)butanoic acid