(1S,3R)-cyclopentane-1,3-dicarboxylic acid

Base Information

• Chemical Name: (1S,3R)-cyclopentane-1,3-dicarboxylic acid
• CAS No.: 876-05-1
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• Hs Code.: 2917209090
• Mol file: 876-05-1.mol

Synonyms:(1R,3S)-Cyclopentane-1,3-dicarboxylic acid;1,3-Cyclopentanedicarboxylic acid, cis-;cis-Cyclopentan-1,3-dicarbonsaeure;cis-Norcamphoric acid;cis-cyclopentane-1,3-dicarboxylic acid;cis-1,3-cyclopentanedicarbonsaeure;cis-1,3-cyclopentane dicarboxylic acid;

Chemical Property of (1S,3R)-cyclopentane-1,3-dicarboxylic acid

Chemical Property:

• Melting Point: 121°C
• Refractive Index: 1.6400 (estimate)
• Boiling Point: 320.7°Cat760mmHg
• PKA: pK1:4.26;pK2:5.51 (25°C)
• Flash Point: 161.9°C
• PSA: 74.60000
• Density: 1.396g/cm³
• LogP: 0.57190
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly, Heated), Water (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

cis-Cyclopentane-1,3-dicarboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1R,3S)-Cyclopentane-1,3-dicarboxylic Acid is used in preparation of bis(Amino Acid) derivatives as inhibitors of human immunodeficiency virus replication and use for treatment of HIV infection.

Technology Process of (1S,3R)-cyclopentane-1,3-dicarboxylic acid

There total 29 articles about (1S,3R)-cyclopentane-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: 99.0%

norborn-2-ene (498-66-8) → cis-1,3-cyclopentanedicarboxylic acid (876-05-1,826-02-8)

Guidance literature:

With sodium periodate; 2C₁₆H₁₃N₂O₁₀Ru₂^(1-)*Ca⁽²⁺⁾; In water; acetone; at 45 ℃; for 16h; Solvent; Reagent/catalyst; Green chemistry;

DOI:10.1002/ejic.201403156

Reference yield: 91.1%

norbornene (498-66-8) → cis-1,3-cyclopentanedicarboxylic acid (876-05-1,826-02-8)

Guidance literature:

With ruthenium trichloride; sodium periodate; In ethyl acetate; acetonitrile; at 25 ℃; for 45h;

DOI:10.1007/s00775-020-01809-9

Reference yield: 72.0%

(1R,2S,3R,4S)-bicyclo[2.2.1]heptane-2,3-diol (16329-23-0) → cis-1,3-cyclopentanedicarboxylic acid (876-05-1,826-02-8)

Guidance literature:

With sodium hydrogencarbonate; potassium carbonate; at 20 ℃; for 24h; electrolysis: nickel oxide hydroxide electrode, 0.3 A;

DOI:10.1055/s-1988-27462

upstream raw materials:

norborn-2-ene

2,3-dimethylenebicyclo<2.2.1>heptane

bicyclo<2.2.1>heptane-2,3-dione

norbornene

Downstream raw materials:

methyl (1R,3S)-3-aminocyclopentane-1-carboxylate

(+)-cis-(1S,3R)-3-carbomethoxycyclopentane carboxylic acid

(1R,3S)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid

Refernces

• 1、 Hoeschele, James D.,Kasparkova, Jana,Kostrhunova, Hana,Novakova, Olga,Pracharova, Jitka,Pineau, Paul,Brabec, Viktor. "Synthesis, antiproliferative activity in cancer cells and DNA interaction studies of [Pt(cis-1,3-diaminocycloalkane)Cl2] analogs". . p. 913 - 924. Retrieved 2020/09/01.
• 2、 Lee, Chia-Han,Wu, Cai-Ling,Hua, Shao-An,Liu, Yi-Hung,Peng, Shie-Ming,Liu, Shiuh-Tzung. "Complexation of tetrakis(acetato)chloridodiruthenium with naphthyridine-2,7-dicarboxylate - Characterization and catalytic activity". . p. 1417 - 1423. Retrieved 2015/03/18.