78989-37-4

Usage

InChI:InChI=1/C10H18O2/c1-3-5-6-7-8-9-10(11)12-4-2/h6-7H,3-5,8-9H2,1-2H3/b7-6+

Upstream product

• 4798-44-1 1-hexene-3-ol 
• 78-39-7 Triethyl orthoacetate 
• 1445-45-0 Trimethyl orthoacetate 

Downstream Products

• 18776-92-6 (E)-2-(pent-1-en-1-yl)benzoic acid 
• 31502-21-3 (E)-oct-4-en-1-ol 
• 212970-48-4 C₄₂H₅₅N₃O₈ 
• 212970-63-3 (2Z,6E,11Z)-2-Hexanoyl-8-oxo-pentadeca-2,6,11-trienoic acid 4-tert-butoxycarbonylamino-butyl ester 
• 212970-55-3 (2Z,6E,11E)-2-Hexanoyl-8-oxo-pentadeca-2,6,11-trienoic acid 4-tert-butoxycarbonylamino-butyl ester 

Relevant academic research and scientific papers

Synthesis of 5Z,9E-tridecadien-1-ylacetate, an attractant of Trichoplusia ni

A new synthetic scheme for 5Z,9E-tridecadien-1-ylacetate, an attractant of the cabbage looper Trichoplusia ni (Huebner) was developed using a highly stereoselective Claisen rearrangement.

Ortho-substituted iodobenzenes as novel organocatalysts for bromination of alkenes

Suitably ortho-substituted iodobenzenes act as organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes via the intermediacy of bromoiodinanes. The Royal Society of Chemistry 2006.

Reagent-Controlled Asymmetric Iodolactonization Using Cinchona Alkaloids as Chiral Sources

A novel method for reagent-controlled asymmetric iodolactonization of 5-aryl-4-pentenoic acids is reported. This work uses carboxylate ion pairs combined with cinchona alkaloids as chiral sources of carboxylate anion for the first time leading to a mixture of two regio-isomeric iodolactones with moderate enantioselectivity (exo-18.5% ee, endo-35.0% ee) under mild reaction conditions.

New stereoselective synthesis of (±)-trans-2-butyl-5-heptyl-1- methylpyrrolidine, ant venom alkaloid, by aminyl radical cyclization

New synthesis of (±)-trans-2-butyl-5-heptyl-1-methylpyrrolidine (1), ant venom alkaloid, was achieved by the use of stereoselective cyclization of aminyl radicals. Thus, orthoester Claisen rearrangement of 1-hexen-3-ol (2) gave (E)-ethyl 4-octenoate (3). Reaction of ester (3) with 2- methylaminopyridine and AlCl3 afforded the corresponding N-methyl-N-(2- pyridyl)amide (4), which was treated with heptylmagnesium iodide at -78°C to give (E)-4-pentadecen-8-one (5). Reductive amination of ketone (5) with methylamine gave N-methyl-1-heptyl-4-octenylamine (6). Treatment of amine (6) with NCS in toluene gave the corresponding N-chloroamine (12), and successive heating under reflux with Bu3SnH and AIBN resulted in stereoselective cyclization of the aminyl radical to give (±)-trans-2-butyl-5-heptyl-1- methylpyrrolidine (1) in a 59percent yield. Similarly, 1-nonen-3-ol (7) was converted into N-methyl-1-butyl-4-undecenylamine (11), which was subjected to the aminyl radical cyclization to give 1 in a 49percent yield.

Z/E-Isomerization of Unsaturated Carboxylic Acids during the Kolbe Electrolysis

Z-4-Enoic acids partially isomerize to E-configurated products in the Kolbe electrolysis.The results from methyl and deuterium labelled carboxylic acids 2 and 16 support an isomerization via a reversible ring closure to cyclopropylcarbinyl radicals.The double bonds of Z-N-enoic acids with N>/= 5 fully retain their configuration in the Kolbe electrolysis; for N=6,7 cyclic products are formed to some extent, which is in accord with the reactivity of 5- and 6-alkenyl radicals.