(2-Hexylcyclopropyl)acetic acid

Base Information

• Chemical Name: (2-Hexylcyclopropyl)acetic acid
• CAS No.: 35936-15-3
• Molecular Formula: C11H20O2
• Molecular Weight: 184.28
• UNII: T3WVU94YXP,D6JJ5NAD77
• DSSTox Substance ID: DTXSID70458675
• Nikkaji Number: J2.100.931H
• Wikidata: Q82282147
• Metabolomics Workbench ID: 44681,74891
• Mol file: 35936-15-3.mol

Synonyms:Cascarillic acid;(2-Hexylcyclopropyl)acetic acid;Cyclopropaneacetic acid, 2-hexyl-, trans-;T3WVU94YXP;87679-85-4;D6JJ5NAD77;Cascarillic acid, (+/-)-;2-Hexylcyclopropaneacetic acid, trans-;(1S,2R)-2-Hexylcyclopropaneacetic acid;2-Hexylcyclopropaneacetic acid, (1S,2R)-;((1S,2R)-2-Hexylcycloprop-1-yl)acetic acid;Cyclopropaneacetic acid, 2-hexyl-, (1S,2R)-;Cyclopropaneacetic acid, 2-hexyl-, (1R,2S)-rel-;35936-15-3;UNII-T3WVU94YXP;UNII-D6JJ5NAD77;DTXSID70458675;LMFA01140032;(1S)-2alpha-Hexylcyclopropane-1beta-acetic acid

Chemical Property of (2-Hexylcyclopropyl)acetic acid

Chemical Property:

• Boiling Point: 282.0±8.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• PSA: 37.30000
• Density: 0.974±0.06 g/cm3(Predicted)
• LogP: 3.06760
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 184.146329876
• Heavy Atom Count: 13
• Complexity: 166

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1CC1CC(=O)O
• Isomeric SMILES: CCCCCC[C@@H]1C[C@H]1CC(=O)O

Technology Process of (2-Hexylcyclopropyl)acetic acid

There total 24 articles about (2-Hexylcyclopropyl)acetic 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: 75.0%

2-((1S,2R)-2-hexylcyclopropyl)acetonitrile (809279-04-7) → 2-((1S,2R)-2-hexylcyclopropyl)acetic acid (35936-15-3)

Guidance literature:

With sodium hydroxide; In methanol; for 6h; Reflux;

DOI:10.1039/c2ob25622c

Reference yield:

C14H26OS2 → 2-((1S,2R)-2-hexylcyclopropyl)acetic acid (35936-15-3)

Guidance literature:

With water; potassium hydroxide; In acetone; at 85 ℃; for 2h; Inert atmosphere;

DOI:10.1039/b908600e

Reference yield:

pentyltriphenylphosphonium bromide (21406-61-1) → 2-((1S,2R)-2-hexylcyclopropyl)acetic acid (35936-15-3)

Guidance literature:

Multi-step reaction with 7 steps

1: BuLi / tetrahydrofuran / -40 °C

2: LiAlH₄ / tetrahydrofuran

3: N₂H₄; NaIO₄; CH₃COOH / CuSO₄; H₂O / propan-2-ol

4: PCC / CH₂Cl₂

5: NaOMe / methanol

6: dimethylsulfoxide

7: NaOH; H₂O / ethanol

With sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; water; sodium methylate; acetic acid; pyridinium chlorochromate; hydrazine; water; copper(II) sulfate; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; isopropyl alcohol; 1: Wittig reation;

DOI:10.1016/j.tetlet.2004.09.141

upstream raw materials:

4-(1-Methylene-heptyl)-oxetan-2-one

(R,R)-2-hexylcyclopropanecarboxaldehyde

2-((1S,2R)-2-hexylcyclopropyl)acetonitrile

pentyltriphenylphosphonium bromide

Refernces

• 1、 -. "CYCLOALKYL-CONTAINING CARBOXYLIC ACIDS AND USES THEREOF". Page/Page column 47; 48-49; 69; 70. . Retrieved 2021/06/26.
• 2、 Cheeseman, Matt,Davies, Iwan R.,Axe, Phil,Johnson, Andrew L.,Bull, Steven D.. "A temporary stereocentre approach for the asymmetric synthesis of chiral cyclopropane-carboxaldehydes". experimental part. p. 3537 - 3548. Retrieved 2010/01/06.