59415-01-9

Basic information

• Product Name: ethyl 2,2-dimethyloctanoate
• Synonyms: ethyl 2,2-dimethyloctanoate;2,2-Dimethyloctanoic acid ethyl ester;Einecs 261-754-6
• CAS NO: 59415-01-9
• Molecular Formula: C₁₂H₂₄O₂
• Molecular Weight: 200.31776
• EINECS: 261-754-6
• Mol File: 59415-01-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 221.3°C at 760 mmHg
• Flash Point: 88.4°C
• Appearance: /
• Density: 0.87g/cm³
• Vapor Pressure: 0.108mmHg at 25°C
• Refractive Index: 1.429
• CAS DataBase Reference: ethyl 2,2-dimethyloctanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,2-dimethyloctanoate(59415-01-9)
• EPA Substance Registry System: ethyl 2,2-dimethyloctanoate(59415-01-9)

Safety Data

• Hazardous Substances Data: 59415-01-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H24O2/c1-5-7-8-9-10-12(3,4)11(13)14-6-2/h5-10H2,1-4H3

Upstream product

• 638-45-9 1-Iodohexane 
• 97-62-1 Ethyl isobutyrate 
• 111-25-1 1-bromo-hexane 

Downstream Products

• 29662-90-6 dimethyloctanoic acid 
• 103906-30-5 2,2-dimethyloctanamide 
• 2370-14-1 2,2-dimethyl-1-octanol 

Relevant articles and documents

Palladium-Catalyzed Arylation of Unactivated γ-Methylene C(sp3)-H and δ-C-H Bonds with an Oxazoline-Carboxylate Auxiliary

A palladium-catalyzed arylation of unactivated γ-methylene C(sp3)-H and remote δ-C-H bonds by using an oxazoline-carboxylate directing group has been developed. Arylation occurs with a broad substrate scope and high tolerance of functional groups (i.e., halogen, nitro, cyano, ether, trifluoromethyl, amine, and ester). The oxazoline-type auxiliary can be removed under acidic conditions.

Potent anandamide analogs: The effect of changing the length and branching of the end pentyl chain

To examine the effect of changing the length and branching of the end pentyl chain (C5H11) of anandamide (AN), various analogs la-h and 2a-f were synthesized from either the known aldehyde ester 6a or from the alcohol 6b and tested for their pharmacological activity. A reproducible procedure was developed for the conversion of arachidonic acid to 6a or 6b in gram quantities (overall yield 15%). The appropriate tetraene esters 7 were prepared by carrying out a Wittig reaction, between 6a and the ylide generated from the phosphonium salt of the appropriate alkyl halide or between the ylide of 6d (prepared from 6a → 6b → 6c → 6d) and the appropriate alkyl aldehydes. They were then hydrolyzed to the corresponding acids and transformed into AN analogs 1 via their acid chlorides then treated with excess ethanolamine. α-Alkylation of esters 7 gave compounds 8 which were hydrolyzed to the corresponding acids. These acids via their acid chlorides and subsequent treatment with excess fluoroethylamine gave the target compounds 2. In this way analogs 1e and 2a-c were synthesized from 6d while all the remaining analogs were prepared from 6a. In order to assess the optimal length of the alkyl terminus, analogs la-d were prepared and showed moderately high affinities(18-55 nM). However analogs la-c failed to produce significant pharmacological effects at doses up to 30 mg/kg. Analog 1d was found to be a weak partial agonist. The reason for the lack of activity in la-c is presently not clear. Like the THCs, the branching of the end pentyl chain in AN (1e-h) increased potency both in in vitro and in vive activities; the dimethylheptyl (DMH) analog 1e was the most potent in the series. Similar alkyl substitutions were carried out in the fluoro-2-methylanandamide series (2a-f), and all of these analogs had high receptor affinities (1-14 nM), the DMH analog 2a being the most potent. With a few exceptions they showed robust pharmacological effects, and AN-like profiles. It was shown that the SAR of the end pentyl chain in AN is very similar to that of THCs. However, the magnitude of enhanced potency observed when the side chain of THC was changed from straight to branched was not observed when the end chain of AN was similarly changed.