132316-71-3

Basic information

• Product Name: Acetic acid, diazo-, (2E)-3-phenyl-2-propenyl ester
• CAS NO: 132316-71-3
• Molecular Formula: C11H10N2O2
• Molecular Weight: 202.213
• Mol File: 132316-71-3.mol

Chemical Properties

• CAS DataBase Reference: Acetic acid, diazo-, (2E)-3-phenyl-2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, diazo-, (2E)-3-phenyl-2-propenyl ester(132316-71-3)
• EPA Substance Registry System: Acetic acid, diazo-, (2E)-3-phenyl-2-propenyl ester(132316-71-3)

Safety Data

• Hazardous Substances Data: 132316-71-3(Hazardous Substances Data)

Upstream product

• 14661-69-9 p-toluenesulfonylhydrazone glyoxylic acid chloride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 2158-14-7 4-acetamidobenzenesulfonyl azide 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 112654-60-1 (E)-cinnamyl bromoacetate 
• 61363-91-5 (E)-(3-phenylallyl) 3-oxo-butyrate 
• 860480-95-1 (E)-(3-phenylallyl)-2-diazo-3-oxo-butyrate 

Downstream Products

• 177188-10-2 (S)-((R)-2-Hydroxy-1-phenyl-ethylamino)-[(1R,2S,3R)-2-(morpholine-4-carbonyl)-3-phenyl-cyclopropyl]-acetonitrile 
• 177188-09-9 (R)-((S)-2-Hydroxy-1-phenyl-ethylamino)-[(1R,2S,3R)-2-(morpholine-4-carbonyl)-3-phenyl-cyclopropyl]-acetonitrile 
• 177188-11-3 (S)-((R)-2-Hydroxy-1-phenyl-ethylamino)-[(1S,2R,3S)-2-(morpholine-4-carbonyl)-3-phenyl-cyclopropyl]-acetonitrile 
• 177188-08-8 (R)-((S)-2-Hydroxy-1-phenyl-ethylamino)-[(1S,2R,3S)-2-(morpholine-4-carbonyl)-3-phenyl-cyclopropyl]-acetonitrile 
• 691001-87-3 PCCG-14 
• 691001-87-3 PCCG-15 
• 691001-87-3 PCCG-13 
• 691001-87-3 PCCG-16 
• 392656-00-7 Imidazole-1-carbothioic acid O-((1S,2S,3R)-2-phenyl-3-phenylsulfanylmethyl-cyclopropylmethyl) ester 
• 392655-81-1 (1R,2S,3S)-tert-butyl 2-acetoxymethyl-3-phenyl-cyclopropanecarboxylate 
• 392655-82-2 (1R,2S,3S)-tert-butyl 2-hydroxymethyl-3-phenyl-cyclopropanecarboxylate 
• 392655-83-3 (1R,2S,3R)-tert-butyl 2-iodomethyl-3-phenyl-cyclopropanecarboxylate 
• 392655-86-6 (3R)-3-phenyl-1-pent-4-en-1-ol 
• 248256-38-4 (1S,2S,3R)-1-methoxythiocarbonyloxymethyl-2-phenyl-3-(phenylthiomethyl)cyclopropane 

Relevant articles and documents

Water-soluble chiral ruthenium(II) phenyloxazoline complex: Reusable and highly enantioselective catalyst for intramolecular cyclopropanation reactions

The intramolecular cyclopropanation of various trans-allylic diazoacetates and alkenyl diazoketones has been achieved with excellent enantioselectivities of up to 98% ee and in quantitative yields by using a water-soluble ruthenium(II)/hydroxymethyl(phenyl)oxazoline catalyst in a water/ether biphasic medium. The catalyst could be reused at least five times.

N,N′-ditosylhydrazine: A convenient reagent for facile synthesis of diazoacetates

A novel entry to the synthesis of diazoacetates is disclosed. A variety of diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N′-ditosylhydrazine in moderate to high yields. Ease of operation with the stable crystalline reagent as well as a short reaction time offer a useful alternative to the conventional methods.

Synthesis and biological evaluation of novel 2-(1H-imidazol-4-yl)cyclopropane carboxylic acids: key intermediates for H3 histamine receptor ligands.

A new synthetic methodology to provide cis-2-(1H-imidazol-4-yl)-cyclopropane carboxylic acids is described. These cyclopropanes are useful for the preparation of novel H(3) receptor agents.

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.

Selective cleavage of the trisubstituted cyclopropanes via cyclopropylcarbinyl radical fragmentation

The fragmentation reaction of the optically pure 2-aryl-3-alkylcyclopropylcarbinyl radicals 1 proceeded selectively to generate a benzyl radical and produce the optically pure 4-aryl-3-alkyl-1-butenes 2, which can serve as synthetically useful chiral buil

Synthesis and pharmacological characterization of all sixteen stereoisomers of 2-(2'-carboxy-3'-phenylcyclopropyl)glycine. Focus on (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-phenylcyclopropyl)glycine, a novel and selective group II metabotropic glutamate receptors antagonist

All 16 2-(2'-carboxy-3'-phenylcyclopropyl)glycine (PCCGs) stereoisomers 32-47 have been prepared from the corresponding racemic aldehydes 12-15 following an enantiodivergent synthetic protocol. Compounds 32-47 were evaluated by a number of binding and functional experiments as potential ligands for several classes of excitatory amino acid receptors, including metabotropic glutamate receptors (mGluR1a, mGluR2, mGluR4) and ionotropic glutamate receptors (NMDA, KA, AMPA) as well as sodium-dependent and calcium/chloride-dependent glutamate transport systems. The stereolibrary of compounds 32-47 appears to be endowed with a peculiar pharmacological profile. PCCG-2 (33) and PCCG-3 (34) displaced labeled kainate at low micromolar concentration; PCCG-9 (40) and PCCG-11 (42) weakly interacted with the NMDA site; PCCG-5 (36), PCCG-10 (41), and PCCG-12 (43) showed to be potent inhibitors of Ca2+/Cl--dependent glutamate transport system. Most interestingly, PCCG-4(35) has been shown to be able to antagonize (IC50 = 8 μM) the effects of glutamate on forskolin-stimulated cAMP formation in BHK cells expressing mGluR2. Uneffective at mGluR1, 35 is a weak mGluR4 agonist (EC50 = 156 μM) and has no effect on either ionotropic receptors or glutamate transport systems, thus demonstrating to be a novel selective mGluR2 antagonist with a 6-fold increase in potency over previously reported antagonists.

Enantioselective intramolecular cyclopropanations of allylic and homoallylic diazoacetates and diazoacetamides using chiral dirhodium(II) carboxamide catalysts

Diazo decomposition of allylic and homoallylic diazoacetates 10a-p and 22a-j catalyzed by chiral dirhodium(II) tetrakis[methyl 2-pyrrolidone-5(S)-carboxylate], Rh2(SS-MEPY)4 (7), and its enantiomer, Rh2(5R-MEPY)4 (8), produces the corresponding intramolecular cyclopropanation products 11a-p and 23a-j in good to excellent yields and with exceptional enantioselectivity. Higher enantiocontrol is observed with allylic diazoacetates than with their homoallylic counterparts, but allylic diazoacetates are subject to greater variations in enantioselectivities with changes in substitution patterns on the carbon-carbon double bond. For example, the enantioselectivities in the intramolecular cyclopropanations of 3-alkyl/aryl-2(Z)-alken-1-yl diazoacetates are generally ≥94%, whereas the cyclizations of the homologous 4-alkyl/aryl-3(Z)-alken-1-yl diazoacetates are typically in the range of 70-90% ee. The corresponding 3-alkyl/aryl-2(E)-alken-1-yl and 4-alkyl/aryl-3(E)-alken-1-yl diazoacetates undergo cyclization with slightly lower ee's (54-85%). Although the Rh2(5S-MEPY)4-catalyzed cyclization of the 2-methallyl diazoacetate 10c proceeds with only 7% ee, alternative chiral dirhodium(II) catalysts, including those with methyl N-acylimidazolidin-2-one-4(5)-carboxylate ligands such as Rh2(4S-MACIM)4 (14) and Rh2(4S-MPAIM)4 (15), may be employed to increase the level of enantiocontrol to 78 and 65%, respectively. Some allylic diazoacetamides also undergo highly enantioselective cyclization to form cyclopropyl lactams as illustrated by the diazo decomposition of N-allyl diazoacetamide (19) in the presence of dirhodium(II) tetrakis[methyl 2-oxazolidinone-4(S)-carboxylate], Rh2(4S-MEOX)4, to give the 3-azabicyclo[3.1.0]hexan-2-one 20 in 98% ee. The absolute configuration and the level of enantiocontrol in these intramolecular cyclopropanations have been interpreted by a transition state model in which the important determinants are (i) the preferred conformation about the rhodium-carbon bond; (ii) the trajectory of approach of the double bond to the metallocarbene center; and (iii) the orientation of the double bond with respect to the chiral face of the catalyst.