4,5-Diacetyloxycyclopentane-1,3-dicarboxylic acid

Base Information

• Chemical Name: 4,5-Diacetyloxycyclopentane-1,3-dicarboxylic acid
• CAS No.: 13190-76-6
• Molecular Formula: C₁₁H₁₄O₈
• Molecular Weight: 274.227
• Hs Code.: 2918990090
• NSC Number: 107383
• DSSTox Substance ID: DTXSID00296062
• Mol file: 13190-76-6.mol

Synonyms:13190-76-6;4,5-diacetyloxycyclopentane-1,3-dicarboxylic acid;NSC107383;DTXSID00296062;NSC-107383

Chemical Property of 4,5-Diacetyloxycyclopentane-1,3-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 2.37E-08mmHg at 25°C
• Boiling Point: 423.3°Cat760mmHg
• Flash Point: 161.4°C
• PSA: 127.20000
• Density: 1.44g/cm³
• LogP: -0.34490
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 274.06886740
• Heavy Atom Count: 19
• Complexity: 377

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(CC(C1OC(=O)C)C(=O)O)C(=O)O

Technology Process of 4,5-Diacetyloxycyclopentane-1,3-dicarboxylic acid

There total 2 articles about 4,5-Diacetyloxycyclopentane-1,3-dicarboxylic 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: 85.0%

Acetic acid (1S,2S,3S,4R)-3-acetoxy-bicyclo[2.2.1]hept-5-en-2-yl ester (20224-40-2,20224-41-3,122306-48-3) → (1β,2α,3α,4β)-2,3-diacetoxy-1,4-cyclopentanedicarboxylic acid (13190-76-6)

Guidance literature:

With potassium permanganate; In 2,2,4-trimethylpentane; water; at 5 ℃; for 3h;

Reference yield:

→ (1β,2α,3α,4β)-2,3-diacetoxy-1,4-cyclopentanedicarboxylic acid (13190-76-6)

Guidance literature:

exo-cis-Norborn-5-en-2,3-diol-diacetat, NaMnO4*3H2O, Wasser, 2,2,4-Trimethylpentan, 10-15grad;

DOI:10.1021/ja01039a042

Reference yield:

(1β,2α,3α,4β)-2,3-diacetoxy-1,4-cyclopentanedicarboxylic acid (13190-76-6) → (+/-)-(1β,2α,3α,4β)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentanecarboxamide (105967-08-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) NH₃ / 1.) reflux, 1h, 2.) 5 deg C, 25 min

2: 79 percent / methanol

3: 93 percent / LiBH₄ / tetrahydrofuran / 2 h / Heating

With lithium borohydride; ammonia; In tetrahydrofuran; methanol;

upstream raw materials:

Acetic acid (1S,2S,3S,4R)-3-acetoxy-bicyclo[2.2.1]hept-5-en-2-yl ester

Downstream raw materials:

(+/-)-(1α,2α,3β,5β)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-(1β,2α,3α,4β)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentanecarboxamide

Refernces