61448-27-9

Basic information

• Product Name: 2-Oxecanone, 10-methyl-
• CAS NO: 61448-27-9
• Molecular Formula: C10H18O2
• Molecular Weight: 170.252
• Mol File: 61448-27-9.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 2-Oxecanone, 10-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxecanone, 10-methyl-(61448-27-9)
• EPA Substance Registry System: 2-Oxecanone, 10-methyl-(61448-27-9)

Safety Data

• Hazardous Substances Data: 61448-27-9(Hazardous Substances Data)

Upstream product

• 69008-87-3 2-decen-9-olide (E isomer) 
• 116288-07-4 (S)-9-Hydroxy-decanethioic acid S-pyridin-2-yl ester 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 99631-16-0 ethyl (S)-4-hydroxypentanoate 
• 908850-87-3 R-(+)-γ-valerolactol 
• 58917-25-2 (R)-5-methyl-2-oxotetrahydrofuran 
• 35433-72-8 (+)-(S)-9-Hydroxydecansaeure 
• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 143956-84-7 (R)-5-hydroxyhexanal 
• 24395-10-6 (R)-hept-6-en-2-ol 
• 138253-40-4 Methanesulfonic acid (R)-(1R,6R,9S)-1-(11,12-dioxa-tricyclo[7.2.1.0^1,6]dodec-6-yl)-ethyl ester 
• 95422-24-5 methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 138253-36-8 (-)-(1R,6S,9S)-6-ethoxycarbonyl-11,12-dioxatricyclo<7.2.1.0^1,6>dodecane 

Downstream Products

• 131111-68-7 (3S,9S)-3-methyl-9-hydroxy-decyl tosylate 
• 131111-71-2 (3R,9S)-3-methyl-9-hydroxy-decyl tosylate 

Relevant articles and documents

Stereoselective synthesis of (R)-(?) and (S)-(+)-phoracantholide I from (R)-(+)-γ-valerolactone

A concise total synthesis of (R)-(?)-phoracantholide I 1 and (S)-(+)-phoracantholide I 2 has been developed from (R)-(+)-γ-valerolactone 6. The key steps in the synthesis of these macrolides involved enzymatic reduction of Levulinic ester 4 by asymmetric dehydrogenase, Z-selective Wittig reaction of (4-carboxybutyl)triphenylphosphonium ylide 11 with lactol 7, and cyclization of seco-acid 8 using either a Yamaguchi lactonization protocol or a Mitsunobu protocol to afford (R)-(?)-phoracantholide I and (S)-(+)-phoracantholide I respectively.

Removable Silyl Group as a "masked Proton" in Oxy-2-oxonia(azonia)-Cope Rearrangement: Applications in Stereoselective Total Synthesis of Natural Macrolides

In the presence of a Lewis acid, trimethylsilyl-substituted β,γ-unsaturated ketones and aldehydes (imines) undergo nucleophilic addition to produce zwitterionic intermediates, followed by oxy-2-oxonia(azonia)-Cope rearrangements to give homoallylic esters (amides). In the case of TMS-containing 2-vinylcycloalkanones, the process results in ring-enlargement, providing 10- to 16-membered lactones. This protocol was applied to the total synthesis of (R)-phoracantholide I.

Lipase-mediated enantioselective acylation of alcohols with functionalized vinyl esters: acyl donor tolerance and applications

Enzymatic acylation is commonly used for the kinetic resolution of alcohols and amines. The simple acyl group introduced during the enzymatic reaction is usually removed or replaced by another group. Retention of more complex acyl moieties as part of the target structures would be a more efficient strategy. We have studied the enantioselective acylation of a model alcohol substrate, 1-phenylethanol, with vinyl esters bearing various functionality on the acyl moieties in the presence of three lipases (Candida antarctica, Candida rugosa and Burkholderia cepacia) frequently used in organic synthesis. C. antarctica lipase is the most versatile lipase for this type of biotransformations. We applied this strategy to the synthesis of a protein kinase C ligand and a natural product, phoracantholide.