131610-03-2

Basic information

• Product Name: 2-Propen-1-ol,3-(2-pyridinyl)-(9CI)
• Synonyms: 2-Propen-1-ol,3-(2-pyridinyl)-(9CI);3-(2-Pyridyl)-2-propen-1-ol
• CAS NO: 131610-03-2
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16316
• Product Categories: PYRIDINE
• Mol File: 131610-03-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Propen-1-ol,3-(2-pyridinyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propen-1-ol,3-(2-pyridinyl)-(9CI)(131610-03-2)
• EPA Substance Registry System: 2-Propen-1-ol,3-(2-pyridinyl)-(9CI)(131610-03-2)

Safety Data

• Hazardous Substances Data: 131610-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Propen-1-ol,3-(2-pyridinyl)-(9CI) is used as a key intermediate in the synthesis of quinolizinones. It is involved in the palladium-catalyzed dearomative cyclocarbonylation of azaarene-substituted allylamines with carbon monoxide, which is a crucial step in the preparation of these compounds.
Used in Chemical Synthesis:
2-Propen-1-ol,3-(2-pyridinyl)-(9CI) is used as a starting material for the preparation of 2-[1-(substituted phenyl)-1-methoxypropyl]thiazoles and analogs. These compounds are selective 5-lipoxygenase (5-LO) inhibitors, which have potential applications in the treatment of various inflammatory and allergic conditions.

Upstream product

• 7340-23-0 (E)-ethyl 3-(2-pyridyl)-propenoate 
• 1121-60-4 pyridine-2-carbaldehyde 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 7340-23-0 ethyl 3-(pyridin-2-yl)acrylate 

Downstream Products

• 491-40-7 quinolizidin-4-one 

Relevant articles and documents

Enantioselective α-functionalization of 1,3-dithianes by iridium-catalyzed allylic substitution

An iridium-catalyzed asymmetric allylic substitution reaction with 2-alkoxy carbonyl-1,3-dithianes has been achieved with high regio- and enantioselectivities. The transformation provides a new method for the enantioselective α-functionalization of dithianes. The corresponding dithiane-containing products are easily converted into many other derivatives with high yields and enantioselectivities.

Synthesis of Allylsilanes via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Allyl Alcohols

NiCl2(PMe3)2-catalyzed reaction of allyl alcohols with silylzinc reagents, including PhMe2SiZnCl, Ph2MeSiZnCl, and Ph3SiZnCl, was performed, achieving allylsilanes in high yields. Aryl- and heteroaryl-substituted allyl alcohols, (E)-3-arylprop-2-en-1-ols, 1-aryl-prop-2-en-1-ols, and (E)-1-phenylpent-1-en-3-ol can be employed in the transformation. A range of functional groups as well as heteroaryl groups were tolerated. Reaction exhibited high regioselectivity and E/Z-selectivity when 1- or 3-aryl-substituted allyl alcohols were used as the substrates. Reaction of chiral allyl alcohol, (S,E)-1-phenylpent-1-en-3-ol, yielded a configuration-inversion product (R,E)-dimethyl(phenyl)(1-phenylpent-1-en-3-yl)silane.

Preparation of Boc-protected cinnamyl-type alcohols: A comparison of the Suzuki-Miyaura coupling, cross-metathesis, and Horner-Wadsworth-Emmons approaches and their merit in parallel synthesis

Three synthetic strategies for the construction of tert-butyl (E)-3-arylprop-2-en-1-ol carbonates are described. Complementary approaches employing Suzuki-Miyaura coupling and cross-metathesis reaction gave moderate yields of the title compounds in one-step, both methods are suitable for high-throughput and parallel chemistry. A detailed investigation into the Suzuki-Miyaura coupling reaction is provided along with the studies on the synthesis of pinacolyl 1-(tert-butyloxycarbonyl)propenol-3-ylboronate, the key building block. Conventional synthesis of the title compounds via the Horner-Wadsworth-Emmons reaction as a key step in a three-step-one-purification protocol was optimized and the results are compared with those of the latter reactions.

Palladium-Catalyzed Cyclocarbonylation of 3-(Heteroaryl)allyl Acetates1

Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130 - 170 deg C under 50 - 70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively.The synthetic utility of the reaction was demonstrated by the synthesis of canabifuran from isothymol.