61363-91-5

Upstream product

• 141-97-9 ethyl acetoacetate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 674-82-8 4-methyleneoxetan-2-one 
• 104-54-1 3-Phenylpropenol 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 105-45-3 acetoacetic acid methyl ester 
• 127-09-3 sodium acetate 

Downstream Products

• 50552-30-2 4-phenyl-5-hexen-2-one 
• 33599-88-1 (E)-6-phenylhex-5-en-2-one 
• 76003-03-7 3-<3-phenyl-2(E)-propen-1-yl>-6-phenyl-5(E)-hexen-2-one 
• 74959-17-4 cinnamyl 2-chloroacetoacetate 
• 132412-14-7 cinnamyl 2-methylacetoacetate 
• 860480-95-1 (E)-(3-phenylallyl)-2-diazo-3-oxo-butyrate 
• 132316-71-3 trans-cinnamyl α-diazoacetate 
• 103909-86-0 (E)-3-phenyl-2-propene-1-yl 3-aminocrotonate 
• 61363-95-9 2-Chloro-3-oxo-butyric acid (E)-3-phenyl-allyl ester 
• 860480-97-3 (E)-(3-phenylallyl)-2-diazo-3-[tri(isopropyl)silanyloxy]-but-3-enoate 
• 248936-93-8 1α,2α,3β-3-phenyl-1,2-cyclopropanedimethanol 

Relevant academic research and scientific papers

N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack adducts with 1,3,5-triazine compounds as efficient catalysts for the transesterification of β-ketoesters

N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack (VH) adducts with 1,3,5-triazine compunds such as trichloroisocyanuric acid (TCCA) and trichlorotriazine (TCTA) were prepared by replacing classical oxy chlorides POCl3, and SOCl2, which were explored as efficient catalysts for the transesterification of β-ketoesters. The prepared (TCCA/DMF) and (TCTA/DMF) adducts improved greenery of the classical Vilsmeier–Haack reagents (POCl3/DMF), and (SOCl2/DMF), and demonstrated their better efficient catalytic ativity. Reaction times were in the range: 3.5 to 6.5 hr (SOCl2/DMF); 2.8–5.2 hr (POCl3/DMF); 2.5–5.2 hr (TCCA/DMF) and 2.5–5.0 hr (TCTA/DMF) catalytic systems. Ultrasonically (US) assisted protocols with these reagents further reduced the reaction times (two to three times), while microwave assisted (MW) protocols with these reagents were much more effective. The reactions could be completed in only few seconds (less than a minute) in MWassisted protocols as compared to US assited reactions, followed by good product yields.

Layered double hydroxides-supported diisopropylamide: Synthesis, characterization and application in organic reactions

The layered double hydroxides-supported diisopropylamide (LDH-DA) catalyst is found to be an efficient and selective solid base for aldol, Knoevenagel, Henry, Michael, transesterification and epoxidation reactions under liquid phase conditions. LDH-DA is synthesized by the interaction of lithium diisopropylamide with LDH-NO3 (as-synthesized) and calcined LDH-NO3. The LDH-DA (Mg/Al, 3/1) and their precursors are well characterized by using various instrumental techniques such as FT-IR, TGA and DTA, powder XRD, solid state 27Al MAS NMR spectroscopy, SEM and XPS (ESCA).

Structure-activity relationship study of 1,4-dihydropyridine derivatives blocking N-type calcium channels

Cilnidipine is a 1,4-dihydropyridine derived L/N-type calcium channel dual blocker possessing neuroprotective and analgesic effects which are related to its N-type calcium channel inhibitory activity. In order to find specific N-type calcium channel blockers with the least effects on cardiovascular system, we performed structure-activity relationship study on APJ2708, which is a derivative of cilnidipine, and found a promising N-type calcium channel blocker 21b possessing analgesic effect in vivo with a 1600-fold lower activity against L-type calcium channels than that of cilnidipine.

3-Nitrobenzeneboronic acid as an efficient and environmentally benign catalyst for the selective transesterification of β-keto esters

An efficient and high-yielding procedure for the selective transesterification of various β-keto esters using 3-nitrobenzeneboronic acid as a catalyst in an environmentally acceptable process is described. Georg Thieme Verlag Stuttgart.

Enantioselective intramolecular cyclopropanation of allyl 2-diazo-3-silanyloxybut-3-enoates

The performance of the [Rh2{(S)-ntt}4]-catalyst in comparison to [Rh2{(S)-pttl}4] and [Rh2{(S)- dosp}4] has been examined with allyl 2-diazo-3-silanyloxybut-3- enoates. The best results were obtained with [Rh2{(S)-pttl} 4], where enantioselectivity culminated at 89% ee at -78°C. [Rh2{(S)-ntt}4] was slightly less selective, while [Rh2{(S)-dosp}4] was found less suitable for these substrates. However, even the results obtained with [Rh2{(S)-pttl} 4] are much less satisfactory than those for the intramolecular cyclopropanation of allyl diazoacetates in the presence of [Rh 2{(S)-mepy}4].

Facile and selective transesterification of β-keto esters using NaIO4, KIO4, and anhydrous CaCl2 as inexpensive catalysts under neutral conditions

NaIO4, KIO4 and anhydrous CaCl2 catalyzed selective transesterification of β-keto esters is described. Neutral reaction conditions and inexpensive catalysts are important features of this method.

Fragmentation reactions of optically active trisubstituted cyclopropylcarbinyl radicals

Fragmentation reactions of optically active trisubstituted cyclopropylcarbinyl radicals and their application to the synthesis of natural products are described. Preparation of the optically pure substrates for radical fragmentation reactions was efficiently accomplished by lipase-mediated desymmetrization of σ-symmetrical 3-substituted-1,2-cy-clopropanedimethanols. In the presence of a radical stabilizing group, e.g., aryl, ester, or α,β-unsaturated ester, the fragmentation occurs selectively to generate the radical on the α-carbon of the group and provide the optically pure alkene derivatives. These derivatives possess three chemically distinct functionalities, making them excellent chiral building blocks for the construction of biologically active molecules. The synthetic usefulness of the procedure developed here has been demonstrated by an application to the enantioselective synthesis of both enantiomers of the key intermediate, 4-(3,4-methylenedioxybenzyl)dihydrofuran-2(3H)-one (54), for the total synthesis of biologically active lignans.

Chemoselective transesterification of β-keto esters under neutral conditions using NBS as a catalyst

Facile and selective transesterification of β-keto esters using N-bromosuccinimide (NBS) as an efficient and neutral catalyst is described.

Sodium perborate catalyzed selective transesterification of β-keto esters under neutral conditions

Transesterification of β-keto esters with various alcohols has been carried out using sodium perborate as an inexpensive catalyst under neutral conditions. The effectiveness of the protocol is manifested in its selectivity towards β-keto esters whereas other esters are found to be unreactive under these reaction conditions.