3-Isobutylglutaric anhydride

Base Information

• Chemical Name: 3-Isobutylglutaric anhydride
• CAS No.: 185815-59-2
• Molecular Formula: C9H14O3
• Molecular Weight: 170.208
• Hs Code.: 2917190090
• European Community (EC) Number: 606-065-7
• DSSTox Substance ID: DTXSID30467187
• Nikkaji Number: J1.706.528I
• Mol file: 185815-59-2.mol

Synonyms:3-Isobutylglutaric anhydride;185815-59-2;4-Isobutyldihydro-2H-pyran-2,6(3H)-dione;4-(2-methylpropyl)oxane-2,6-dione;2H-Pyran-2,6(3H)-dione, dihydro-4-(2-methylpropyl)-;3-isobutyl glutaric anhydride;3-isobutyl-glutaric anhydride;SCHEMBL338034;3-isobutylglutaric acid anhydride;AMY3881;DTXSID30467187;XLSGYCWYKZCYCK-UHFFFAOYSA-N;MFCD27946568;AKOS023203260;DS-7390;CS-0154236;FT-0715509;C73571;A880702;4-(2-Methylpropyl)tetrahydropyran-2,6-dione (3-Isobutylglutaric Anhydride);Dihydro-4-(2-methylpropyl)-2H-pyran-2,6(3H)-dione;3-Isobutylglutaric Acid Anhydride

Chemical Property of 3-Isobutylglutaric anhydride

Chemical Property:

• Vapor Pressure: 0.00406mmHg at 25°C
• Refractive Index: 1.451
• Boiling Point: 279.3 °C at 760 mmHg
• Flash Point: 124 °C
• PSA: 43.37000
• Density: 1.054 g/cm³
• LogP: 1.51230
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 170.094294304
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

3-IsobutylglutaricAnhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1CC(=O)OC(=O)C1
• Uses: 3-Isobutylglutaric anhydride is an impurity of Pregabalin (P704800), a ligand for the alpha-2-delta subunit of voltage-gated calcium channels that exhibits anticonvulsant and analgesic activity.

Technology Process of 3-Isobutylglutaric anhydride

There total 7 articles about 3-Isobutylglutaric anhydride 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: 91.0%

5-methyl-3-carboxymethylhexanoic acid (75143-89-4) → 3-isobutylglutaric anhydride (185815-59-2)

Guidance literature:

With propionic acid anhydride; at 140 - 145 ℃; for 6h;

Reference yield: 65.0%

isovaleraldehyde (590-86-3) + cyanoacetic acid amide (107-91-5) → 3-isobutylglutaric anhydride (185815-59-2)

Guidance literature:

isovaleraldehyde; cyanoacetic acid amide; piperidine; In dichloromethane; water; at 22 - 25 ℃; for 6h;

With hydrogenchloride; In water; for 20h; Heating;

With acetic anhydride; for 2h; Further stages.; Heating;

DOI:10.1016/j.tetasy.2007.06.014

Reference yield: 61.0%

→ 3-isobutylglutaric anhydride (185815-59-2)

Guidance literature:

With acetic anhydride; at 130 ℃;

upstream raw materials:

5-methyl-3-carboxymethylhexanoic acid

isovaleraldehyde

cyanoacetic acid amide

diethyl 2-(3-methylbutylidene)malonate

Downstream raw materials:

(-)-(R)-3-isobutyl-pentanedioic acid mono-(3-phenyl-allyl) ester

(3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid

C₁₈H₂₄O₄

(R)-1-(2,4,6-trimethyl-phenyl)-ethanethiol

Refernces

• 1、 -. "Method for synthesizing optically pure (R)-3-carbamoymethyl-5-methylhexanoic acid". Paragraph 0019; 0021; 0025; 0028; 0032. . Retrieved 2019/09/14.
• 2、 -. "Method for preparing Pregabalin intermediate". Page/Page column 5-9. . Retrieved 2019/01/06.