66810-79-5

Upstream product

• 109-69-3 n-Butyl chloride 
• 100-51-6 benzyl alcohol 
• 109-72-8 n-butyllithium 
• 18982-54-2 o-bromobenzyl alcohol 
• 100256-40-4 2-(n-Butyl)-benzoesaeuremethylester 
• 1409942-08-0 methyl 2-(but-1-yn-1-yl)benzoate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 89-95-2 2-methyl-benzyl alcohol 
• 107-08-4 1-iodo-propane 
• 109-65-9 1-bromo-butane 

Downstream Products

• 1268267-75-9 5-(2-butylbenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 
• 59059-42-6 2-butylbenzaldehyde 

Relevant academic research and scientific papers

Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands

Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.

Role of the CAI-1 fatty acid tail in the Vibrio cholerae quorum sensing response

Quorum sensing is a mechanism of chemical communication among bacteria that enables collective behaviors. In V. cholerae, the etiological agent of the disease cholera, quorum sensing controls group behaviors including virulence factor production and biofilm formation. The major V. cholerae quorum-sensing system consists of the extracellular signal molecule called CAI-1 and its cognate membrane bound receptor called CqsS. Here, the ligand binding activity of CqsS is probed with structural analogues of the natural signal. Enabled by our discovery of a structurally simplified analogue of CAI-1, we prepared and analyzed a focused library. The molecules were designed to probe the effects of conformational and structural changes along the length of the fatty acid tail of CAI-1. Our results, combined with pharmacophore modeling, suggest a molecular basis for signal molecule recognition and receptor fidelity with respect to the fatty acid tail portion of CAI-1. These efforts provide novel probes to enhance discovery of antivirulence agents for the treatment of V. cholerae.

Expeditious construction of a carbobicyclic skeleton via sp3-C-H functionalization: Hydride shift from an aliphatic tertiary position in an internal redox process

Described herein is the first example of an aliphatic, nonbenzylic hydride shift/cyclization sequence that contains two types of novel sp3-C-H functionalization: (1) construction of a tetraline skeleton via [1,5]-hydride shift/cyclization and (2) [1,6]-hydride shift/cyclization to form a five-membered ring (indane derivatives).

Process for producing cyclopropanecarboxylates

There is disclosed a process process for producing a cyclopropanecarboxylate of formula (1): 1which process comprises reacting cyclopropanecarboxylic acid of formula (2): 2with a monohydroxy compound of formula (3): R6OH??(3),in the presence of a catalyst compound comprising an element of to Group 4 of the Periodic Table of Elements.

Direct ortho-Metalation of Benzyl Alcohols. A Novel Method of Preparing ortho-Substituted Benzyl Alcohols

Benzyl alcohol and other phenylcarbinols (8a - 11a), including α-tetralol (12a), are doubly deprotonated by excess n-butyllithium/TMEDA in pentane to give lithium ortho-lithioalkoxides (2, 8b - 12b).Alkylations (-> 3a - d, table 1), reactions with heteroelectrophiles (-> 3e - k, table 2) and with carbonyl compounds (-> 6, 13 - 17, tables 3 and 4), as well as subsequent reactions of the primary adducts (-> phthalanes 7, table 3) furnish a large variety of ortho-substituted benzyl alcohol derivatives.The scope and limitations of the dilithioorganyls (sections B and C), their mode of formation (section A), and attempts to doubly metalate 2-phenylethanol are discussed.