37428-50-5

Usage

Uses

Used in Organic Synthesis:
(E)-3-iodoprop-2-en-1-ol is used as an intermediate in organic synthesis for the preparation of various chemicals and pharmaceuticals. Its unique structure and reactivity make it a valuable component in creating a range of compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (E)-3-iodoprop-2-en-1-ol is employed as a reagent, contributing to the development and synthesis of novel pharmaceuticals. Its properties allow for the creation of new drug candidates with potential therapeutic applications.
Used in Chemical Product Production:
(E)-3-iodoprop-2-en-1-ol is also utilized in the production of certain chemical products, highlighting its versatility and importance in the chemical industry.
Used in Research:
(E)-3-iodoprop-2-en-1-ol serves as a research reagent, aiding scientists in understanding various chemical reactions and mechanisms, which can lead to advancements in related fields.
It is crucial to handle (E)-3-iodoprop-2-en-1-ol with care due to its potential reactivity and toxicity, ensuring safety in both laboratory and industrial settings.

Upstream product

• 6213-88-3 3-iodoacrylic acid methyl ester 
• 1725-82-2 3-iodo-2-propyn-1-ol 
• 6214-23-9 methyl (2Z)-3-iodoprop-2-enoate 
• 107-19-7 propargyl alcohol 
• 31930-36-6 ethyl (Z)-3-iodopropenoate 
• 151502-81-7 cis-3-dimethyl(1,1-dimethylethyl)silyloxy-1-iodo-1-propene 
• 1191-15-7 diisobutylaluminium hydride 
• 31930-36-6 ethyl (E)-3-iodopropenoate 
• 6213-88-3 (E)-methyl 3-iodoacrylate 
• 82994-41-0 (E)-3-(tri-n-butylstannyl)-2-propen-1-ol 
• 6372-02-7 (E)-3-iodoacrylic acid 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 497-23-4 2-buten-4-olide 
• 129593-48-2 (Z)-5-phenyl-2-penten-4-yn-1-ol 
• 313227-83-7 N-[(2Z)-3-iodo-2-propenyl]-p-toluenesulfonamide 
• 97514-97-1 (E)-5-trimethylsilanylpent-2-en-4-yn-1-ol 
• 91060-73-0 (E)-2-decen-4,6-diyn-1-ol 
• 499158-38-2 4-Methoxy-benzoic acid (E)-3-iodo-allyl ester 
• 35042-52-5 (E)-2-penten-4-yn-1-ol 
• 7199-99-7 7-hydroxy-1-phenyl-hept-5E-ene-1,3-diyne 
• 1647100-84-2 (E)-tert-butyl (3-iodoallyl)(tosyl)carbamate 
• 1042150-46-8 (E)-1-(((3-iodoallyl)oxy)methyl)-4-methoxybenzene 
• 87832-31-3 (Z)-1-hydroxypenta-2,4-diene 
• 1197011-09-8 (Z)-1-iodo-3-(4-methoxybenzyloxy)-1-propene 

Relevant academic research and scientific papers

Stereoselective stille coupling of enantiopure haloallenes and alkenylstannanes for the synthesis of allenyl carotenoids. Experimental and computational studies

(Chemical Equation Presented) The stereoselectivity of the Stille cross-coupling of chiral enantiopure haloallenes and alkenylstannanes en route to allenic carotenoids is shown to depend on the nature of the halogen and palladium catalyst as well as on th

PREPARATION OF IODOALLYLIC ALCOHOLS VIA HYDROSTANNYLATION: SPECTROSCOPIC PROOF OF STRUCTURES

Hydrostannylation of propargylic alcohols and ethers affords either the E- or Z-β-tributylstannylallylic alcohols and ethers as the major products by the use of excess stannane or acetylenic compound, respectively; europium shift studies in the high field

Tetraquinane diterpenoids: Total synthesis of (±)-crinipellin B

The total synthesis of (±)-crinipellin B (4), via a 22-step sequence of reactions starting from 2-methylcyclopent-2-en-1-one (7), is described. Three distinctly different five-membered annulation sequences (7 → 11, Scheme 1; 11 → 15, Scheme 2; 19 → 30, Scheme 4) played pivotal roles in the synthetic pathway. The constitution and relative configuration of a key synthetic intermediate, compound 32, was confirmed by an X-ray crystallographic study.

Stereocontrolled synthesis of lissoclinolide by sequential transition metal-catalyzed lactonization / cross-coupling reactions

Lissoclinolide, 1, which is an antibiotic butenolide isolated from a Tunicate, has been synthesized stereoselectively by a reaction sequence in which the Ag(I)-catalyzed lactonization of (2E,6E)-2-bromo-8-hydroxy-2,6- octadien-4-ynoic acid, (E,E)-13, and the Pd/Cu-catalyzed cross-coupling reaction of so obtained (Z)-2-bromo-5-[(E)-4-hydroxy-2-butenylidene]-5H- furan-2-one, (Z,E)-14, with (E)-3-hydroxy-1-propenyltributylstannane, 15, have been used as the key steps.

Intramolecular Diels-Alder Approaches to the Decalin Core of Verongidolide: The Origin of the exo-Selectivity, a DFT Analysis

Verongidolide is a natural macrolactone recently isolated from a New Caledonia sponge, Verongidolae. The structure of this natural product is similar to the structure of superstolides, also isolated from a New Caledonian sponge, Neosiphonia superstes. From a biological point of view, verongidolide and superstolides A and B present potent cytotoxicity against human oral carcinoma KB (0.3 nM). By comparing the 1H NMR chemical shifts as well as the coupling constants, we conclude that verongidolide possesses a cis-decalin core and we hypothesize that the relative configuration of the cis-decalin core is similar to the one of superstolide A. To verify this hypothesis, intramolecular and transannular Diels-Alder reactions were attempted to construct the decalin core. Unexpectedly, the selectivity of the Diels-Alder reactions was exo and an in-depth DFT calculation of the key reaction mechanism was achieved in order to understand the factors controlling this unexpected selectivity.

Synthesis, radiolabeling, and preliminary in vivo evaluation of [68ga] ipcat-nota as an imaging agent for dopamine transporter

Introduction: Novel radiotracer development for imaging dopamine transporters is a subject of interest because although [99mTc]TRODAT-1, [123I]β-CIT, and [123I]FP-CIT are commercially available;99Mo/99mTc generator is in short supply and123I production is highly dependent on compact cyclotron. Therefore, we designed a novel positron emission tomography (PET) tracer based on a tropane derivative through C-2 modification to conjugate NOTA for chelating68Ga, a radioisotope derived from a68Ge/68Ga generator. Methods: IPCAT-NOTA 22 was synthesized and labeled with [68Ga]GaCl4 ? at room tem-perature. Biological studies on serum stability, LogP, and in vitro autoradiography (binding assay and competitive assay) were performed. Furthermore, ex vivo autoradiography, biodis-tribution, and dynamic PET imaging studies were performed in Sprague Dawley rats. Results: [68Ga]IPCAT-NOTA 24 obtained had a radiochemical yield of ≥90% and a specific activity of 4.25 MBq/nmol. [68Ga]IPCAT-NOTA 24 of 85% radiochemical purity (RCP%) was stable at 37°C for up to 60 minutes in serum with a lipophilicity of 0.88. The specific binding ratio (SBR%) reached 15.8 ± 6.7 at 60 minutes, and the 85% specific uptake could be blocked through co-injection at 100-and 1000-fold of the cold precursor in in vitro binding studies. Tissue regional distribution studies in rats with [68Ga]IPCAT-NOTA 24 showed striatal uptake (0.02% at 5 minutes and 0.007% at 60 minutes) with SBR% of 6%, 25%, and 62% at 5–15, 30–40, and 60–70 minutes, respectively, in NanoPET studies. The RCP% of [68Ga]IPCAT-NOTA 24 at 30 minutes in vivo remained 67.65%. Conclusion: Data described here provide new information on the design of PET probe of conjugate/pendent approach for DAT imaging. Another chelator or another direct method of intracranial injection must be used to prove the relation between [68Ga]IPCAT-NOTA 24 uptake and transporter localization.

Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis

Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.

Palladium-catalysed regio- And stereoselective arylative substitution of γ,δ-epoxy-α,β-unsaturated esters and amides by sodium tetraaryl borates

Palladium-catalysed reactions of γ,δ-epoxy-α,β-unsaturated esters and amides with NaBAr4 reagents proceeded regio- and stereoselectively, producing allylic homoallyl alcohols with aryl-substituents in the allylic position for a wide range of substrates. A

SYNTHESIS OF DISORAZOLES AND ANALOGS THEREOF AS POTENT ANTICANCER AGENTS

In one aspect, the present disclosure provides disorazole analogs of the formula: Formula (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.

Flow synthesis of (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol: Chiral building blocks for natural product synthesis

A concise procedure to prepare optically active (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol was developed. Ethyl (E)-3-iodoacrylate was converted to racemic (E)-1-iodohexa-1,5-dien-3-ol under flow and batch conditions via successive half reduction followed by Grignard reaction. Kinetic resolution of the racemic alcohol was achieved under flow conditions by using lipase packed in a column to afford (3S)-(E)-1-iodohexa-1,5-dien-3-ol and corresponding (3R)-acetate. Removal of the acetyl group was also carried out under flow conditions by using ion exchange resin packed in a column and (3R)-(E)-1-iodohexa-1,5-dien-3-ol was obtained after simple evaporation of the eluent.