74183-94-1

Basic information

• Product Name: 10-Methyloxecan-2-one
• Synonyms: 10-Methyloxecan-2-one;9-Hydroxy-9-methylnonanoic acid lactone;Phoracantholide I
• CAS NO: 74183-94-1
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• Mol File: 74183-94-1.mol
• Article Data: 40

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 10-Methyloxecan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Methyloxecan-2-one(74183-94-1)
• EPA Substance Registry System: 10-Methyloxecan-2-one(74183-94-1)

Safety Data

• Hazardous Substances Data: 74183-94-1(Hazardous Substances Data)

Upstream product

• 65371-27-9 2-decen-9-olide (Z isomer) 
• 67400-99-1 (+/-)-phoracantholide J 
• 118162-68-8 9-Decanelactam 
• 1121-66-0 2-Cyclohepten-1-one 
• 127974-26-9 ((1S,9S)-10-Chloro-3-methyl-2-oxa-bicyclo[7.1.0]dec-1-yloxy)-trimethyl-silane 
• 35433-72-8 (+)-(S)-9-Hydroxydecansaeure 
• 88851-71-2 (+)-(S)-9-Hydroxydecansaeure-methylester 
• 85852-44-4 (R)-4-(tetrahydropyranyloxy)pentyl iodide 
• 85852-46-6 (R)-4-tetrahydropyranyloxy-1-pentyl tosylate 
• 85881-63-6 (9R,4Z)-9-hydroxydec-4-enoic acid 
• 85881-62-5 methyl (R)-9-hydroxy-4(Z)-decenoate 
• 85852-47-7 methyl (R)-9-hydroxy-4-decynoate 
• 85881-64-7 (Z)-(R)-9-Hydroxy-dec-4-enethioic acid S-pyridin-2-yl ester 
• 24395-10-6 (R)-hept-6-en-2-ol 

Downstream Products

• 131111-68-7 (3S,9S)-3-methyl-9-hydroxy-decyl tosylate 
• 131111-71-2 (3R,9S)-3-methyl-9-hydroxy-decyl tosylate 
• 97466-68-7 (+/-)-pyrenolide B 

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.

Silver carboxylate promoted lactonization: A general method applicable to prepare medium and large-sized lactones without high dilution or slow addition

Efficient and applicable approach to macrolactonizations, with ready availability of starting materials and simple operation, remains a challenging task for the organic community. We developed a 'freshman-can-do' protocol to medium- and large-sized lactones, not depending on high-dilution or slow addition techniques. Application of this method for the synthesis of natural lactones or potentially pharmaceutical compounds might be useful for organic chemists and pharmacists.

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.