46275-03-0

Basic information

• Product Name: methyl (2E)-3-(2,6-dichlorophenyl)prop-2-enoate
• Synonyms: methyl (2E)-3-(2,6-dichlorophenyl)prop-2-enoate
• CAS NO: 46275-03-0
• Molecular Weight: 231.078
• Mol File: 46275-03-0.mol

Chemical Properties

• CAS DataBase Reference: methyl (2E)-3-(2,6-dichlorophenyl)prop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2E)-3-(2,6-dichlorophenyl)prop-2-enoate(46275-03-0)
• EPA Substance Registry System: methyl (2E)-3-(2,6-dichlorophenyl)prop-2-enoate(46275-03-0)

Safety Data

• Hazardous Substances Data: 46275-03-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 20595-49-7 (2E)-3-(2,6-dichlorophenyl)prop-2-enoic acid 
• 5927-18-4 trimethyl phosphonoacetate 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 541-73-1 1,3-Dichlorobenzene 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 38169-98-1 5-Chlor-2H-1-benzopyran-2-on 
• 85995-42-2 2-chloro-6-methoxy-cis-cinnamic acid 
• 59507-35-6 methyl (2Z)-3-(2,6-dichlorophenyl)prop-2-enoate 

Relevant articles and documents

Efficient synthesis of acrylates bearing an aryl or heteroaryl moiety: One-pot method from aromatics and heteroaromatics using formylation and the horner-wadsworth-emmons reaction

Acrylates bearing an aryl or heteroaryl moiety were efficiently prepared by a one-pot process employing a sequence of lithiation, formylation and the Horner-Wadsworth-Emmons reaction starting from aromatic and heteroaromatic compounds. This method can efficiently introduce an acrylate moiety into aromatic and heteroaromatic compounds.

Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.

METHODS FOR PHOSPHINE OXIDE REDUCTION IN CATALYTIC WITTIG REACTIONS

A method for increasing the rate of phosphine oxide reduction, preferably during a Wittig reaction comprising use of an acid additive is provided. A room temperature catalytic Wittig reaction (CWR) the rate of reduction of the phosphine oxide is increased due to the addition of the acid additive is described. Furthermore, the extension of the CWR to semi-stabilized and non-stabilized ylides has been accomplished by utilization of a masked base and/or ylide-tuning.

Breaking the ring through a room temperature catalytic wittig reaction

One ring no longer rules them all: Employment of 2.5-10 mol % of 4-nitrobenzoic acid with phenylsilane led to the development of a room temperature catalytic Wittig reaction (see scheme). Moreover, these enhanced reduction conditions also facilitated the use of acyclic phosphine oxides as catalysts for the first time. A series of alkenes were produced in moderate to high yield and selectivity. Copyright

Part I: The development of the catalytic wittig reaction

We have developed the first catalytic (in phosphane) Wittig reaction (CWR). The utilization of an organosilane was pivotal for success as it allowed for the chemoselective reduction of a phosphane oxide. Protocol optimization evaluated the phosphane oxide precatalyst structure, loading, organosilane, temperature, solvent, and base. These studies demonstrated that to maintain viable catalytic performance it was necessary to employ cyclic phosphane oxide precatalysts of type 1. Initial substrate studies utilized sodium carbonate as a base, and further experimentation identified N,N-diisopropylethylamine (DIPEA) as a soluble alternative. The use of DIPEA improved the ease of use, broadened the substrate scope, and decreased the precatalyst loading. The optimized protocols were compatible with alkyl, aryl, and heterocyclic (furyl, indolyl, pyridyl, pyrrolyl, and thienyl) aldehydes to produce both di- and trisubstituted olefins in moderate-to-high yields (60-96 %) by using a precatalyst loading of 4-10 mol %. Kinetic E/Z selectivity was generally 66:34; complete E selectivity for disubstituted α,β-unsaturated products was achieved through a phosphane-mediated isomerization event. The CWR was applied to the synthesis of 54, a known precursor to the anti-Alzheimer drug donepezil hydrochloride, on a multigram scale (12.2 g, 74 % yield). In addition, to our knowledge, the described CWR is the only transition-/heavy-metal-free catalytic olefination process, excluding proton-catalyzed elimination reactions. A point of difference: By utilizing an organosilane to chemoselectively reduce a phosphane oxide precatalyst to a phosphane (see scheme), the first catalytic (in phosphane) Wittig reaction has been developed. The methodology has been applied to the synthesis of 22 disubstituted and 24 trisubstituted olefins, including a multigram synthesis of a precursor to the anti-Alzheimer drug donepezil hydrochloride.

Substituted isoxazole analogs of farnesoid X receptor (FXR) agonist GW4064

Starting from the known FXR agonist GW 4064 1a, a series of alternately 3,5-substituted isoxazoles was prepared. Several of these analogs were potent full FXR agonists. A subset of this series, with a tether between the isoxazole ring and the 3-position aryl substituent, were equipotent FXR agonists to GW 4064 1a, with the 2,6-dimethyl phenol analog 1t having greater FRET FXR potency than GW 4064 1a.

Photocyclization of 2,6-Dichlorocinnamic Acid Derivatives to 5-Chlorocoumarin

On UV irradation, 2,6-dichlorocinnamic acid and its esters undergo photocyclization with elimination of the elements of HCl or RCl (R = alkyl or aryl) to yield 5-chlorocoumarin (2); amide derivatives yield the corresponding imino analogues.Low-temperature