1061567-18-7

Basic information

• Product Name: C₁₃H₁₇NO₄
• Synonyms: C₁₃H₁₇NO₄
• CAS NO: 1061567-18-7
• Molecular Weight: 251.282
• Mol File: 1061567-18-7.mol

Chemical Properties

• CAS DataBase Reference: C₁₃H₁₇NO₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₃H₁₇NO₄(1061567-18-7)
• EPA Substance Registry System: C₁₃H₁₇NO₄(1061567-18-7)

Safety Data

• Hazardous Substances Data: 1061567-18-7(Hazardous Substances Data)

Upstream product

• 564472-38-4 3-(4-methyl-2-pentenoyl)-2-oxazolidinone 
• 71735-01-8 1-methoxy-[3-(tert-butyldimethylsilyl)oxy]-1,3-butadiene 

Downstream Products

• 38750-01-5 (1S,2S,6R,8R,11S)-11-isopropyl-6-methyl-5-methylene-9-oxatricyclo[6.2.1.0^2,6]undecan-7,10-dione 
• 2115-91-5 dendrobine 
• 7668-77-1 Dendroxin 

Relevant articles and documents

Catalytic Enantioselective Total Synthesis of the Picrotoxane Alkaloids (-)-Dendrobine, (-)-Mubironine B, and (-)-Dendroxine

A concise enantioselective total synthesis of three sesquiterpenoid alkaloids - (-)-dendrobine, (-)-mubironine B, and (-)-dendroxine - is presented, which highlights the state-of-art catalytic methods, including enantioselective Diels-Alder cycloaddition, iron-catalyzed aerobic lactonization, copper-catalyzed cycloisomerization, and free-radical-initiated hydroazidation.

Highly enantioselective Diels Alder reactions of Danishefsky type dienes with electron-deficient alkenes catalyzed by Yb(III)-BINAMIDE complexes

1-Methoxy-3-trimethylsiloxy-1,3-butadiene (Danishefsky-s diene) is recognized as a synthetically useful diene due to its high reactivity in the Diels-Alder reaction with electron-deficient alkenes to give oxygen-functionalyzed cyclohexenes and substituted cyclohexenones, which are important building blocks for the total synthesis of natural products. However, the development of catalytic enantioselective versions of Diels-Alder reactions using Danishefsky type dienes with electron-deficient alkenes has been difficult because of the instability of the dienes under Lewis acidic conditions. Only highly reactive C=O and C=N double bonds are employed in a hetero-Diels-Alder reaction which proceeds under catalysis of chiral Lewis acids. We have developed a new chiral ligand, BINAMIDE, which is easily prepared from 1,1′-binaphtyl-2,2′-diamine by acylation. The highly diastereo- and enantioselective Diels-Alder reaction of Danishefsky type dienes with electron-deficient alkenes in the presence of an Yb(III)-BINAMIDE complex has been developed. The reaction proceeded in an exoselective mode and gave chiral highly functionalized cyclohexene derivatives in good yields. Copyright