64584-92-5

Basic information

• Product Name: (R)-(-)-PENTEN-2-OL
• Synonyms: (R)-(-)-2-HYDROXYPENT-4-ENE;(R)-(-)-PENTEN-2-OL;(r)-(-)-4-penten-2-ol;(1R)-1-Methyl-3-butene-1-ol;(2R)-4-Pentene-2-ol;(2R)-pent-4-en-2-ol
• CAS NO: 64584-92-5
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.13
• Product Categories: API intermediates;Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 64584-92-5.mol
• Article Data: 71

Chemical Properties

• Boiling Point: 115-116 °C(lit.)
• Flash Point: 78 °F
• Appearance: /
• Density: 0.837 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4240(lit.)
• PKA: 15.10±0.20(Predicted)
• Water Solubility: Soluble in water, 4.526 mg/L @ 25°C.
• CAS DataBase Reference: (R)-(-)-PENTEN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-PENTEN-2-OL(64584-92-5)
• EPA Substance Registry System: (R)-(-)-PENTEN-2-OL(64584-92-5)

Safety Data

• Hazard Codes: H226
• Statements: 10
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 64584-92-5(Hazardous Substances Data)

Usage

Description

(R)-(-)-PENTEN-2-OL, also known as (R)-2-Penten-1-ol, is an organic compound with the molecular formula C5H10O. It is a chiral secondary alcohol, characterized by its distinct (R) configuration at the chiral center. (R)-(-)-PENTEN-2-OL is a colorless liquid with a distinctive odor and is soluble in water and various organic solvents. It is an important building block in the synthesis of various organic compounds, particularly in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-PENTEN-2-OL is used as a reactant in the synthesis of aigialomycin D and its analogs, which are known to inhibit protein kinases related to cancer pathways. These compounds have potential applications in the development of novel anticancer drugs, targeting the specific protein kinases that play a crucial role in the growth and progression of cancer cells.
In the synthesis of aigialomycin D and its analogs, (R)-(-)-PENTEN-2-OL serves as a key intermediate, providing the necessary structural framework for the formation of the final product. (R)-(-)-PENTEN-2-OL's unique (R) configuration at the chiral center is essential for the biological activity of the synthesized compounds, as it ensures the correct stereochemistry for effective binding to the target protein kinases.
Furthermore, (R)-(-)-PENTEN-2-OL can be used as a starting material for the synthesis of other bioactive compounds with potential applications in the pharmaceutical industry. Its versatility as a building block allows for the development of a wide range of molecules with diverse biological activities, including those with potential therapeutic benefits.

Upstream product

• 111957-98-3 Pent-4-en-2-ol 
• 688-61-9 Triallylborane 
• 75-07-0 acetaldehyde 
• 85116-38-7 (+)-diisopinocampheylallylborane 
• 92055-65-7 B-allyldiisocaranylborane 
• 77078-92-3 (-)-(1R,2S,3S,4S)-2,3-O-Allylborylen-2-endo-methyl-3-endo-phenyl-2-exo,3-exo-bornandiol 
• 67760-74-1 (-)-(1R,2S,3S,4S)-2,3-O-Allylborylen-3-endo-phenyl-2-exo,3-exo-bornandiol 
• 7785-70-8 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 1730-25-2 allylmagnesium bromide 
• 143143-11-7 2,2,2-Trifluoro-N-[(1R,2R)-1-methyl-2-((R)-1-methyl-but-3-enyloxy)-2-phenyl-ethyl]-acetamide 
• 1826-67-1 vinyl magnesium bromide 
• 15448-47-2 (R)-propylene oxide 
• 335161-40-5 3,5-Dinitro-benzoic acid (R)-1-methyl-but-3-enyl ester 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 300-85-6 3-Hydroxybutyric acid 
• 115461-39-7 19(R)-hydroxyeicosatetraenoic acid 
• 1026503-64-9 (4R)-4-<(p-Nitrobenzoyl)oxy>pentanoic acid 
• 1158076-93-7 (1R)-1-methyl-3-butenyl (5S)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-6-heptenoate 
• 1159792-63-8 C₁₅H₂₀O₄ 
• 1147106-37-3 (2Z,4E)-((S)-pent-4-en-2-yl) 3-ethyl-4-(4-methylbenzoyl)hexa-2,4-dienoate 
• 1147106-49-7 (2Z,4E)-((S)-pent-4-en-2-yl) 4-(4-bromobenzoyl)-3-methylnona-2,4,8-trienoate 
• 1147106-57-7 (S,2Z,4E)-((R)-pent-4-en-2-yl) 4-(4-bromobenzoyl)-3-ethyl-7,11-dimethyldodeca-2,4,10-trienoate 
• 1147106-54-4 (S,2Z,4E)-((S)-pent-4-en-2-yl) 4-(4-bromobenzoyl)-3-ethyl-7,11-dimethyldodeca-2,4,10-trienoate 
• 86040-06-4 {[(2R)-pent-4-en-2-yloxy]methyl}benzene 
• 1225202-30-1 C₂₀H₃₀O₄ 
• 1333331-64-8 tert-butyl (((2S,8R,9R)-11-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-2,9-dimethyl-14-nitro-12-oxo-2,3,6,8,9,10,11,12-octahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)(methyl)carbamate 
• 1333331-66-0 tert-butyl (((2S,8R,9R)-14-amino-11-((S)-1-((4-methoxybenzyloxy)prop-2-yl)-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-ecahydrobenzo[b][1,9,5]dioxaazacyclotetradec-8-yl)methyl)-methyl)carbamate 
• 847049-72-3 1-methoxy-4-{[(2S)-pent-4-en-2-yloxy]methyl}benzene 

Relevant articles and documents

Asymmetric synthesis of (+)-stagonolide C and (-)-aspinolide A via organocatalysis

A new enantioselective synthesis of two important fungal metabolites, (+)-stagonolide C and (-)-aspinolide A, has been described from readily available raw materials. Proline catalyzed asymmetric α-aminooxylation and Jorgensen's epoxidation of aldehydes a

Total synthesis of (–)-cephalosporolide D

In this communication, a concise and efficient synthetic route for the synthesis of (–)-Cephalosporolide D in enantioselective way has been described. In this synthesis, Mitsunobu esterification and Ring Closing Metathesis (RCM) for macrocyclic ring formation have been applied as key steps.

A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.

A facile, efficient and selective deprotection of p-methoxy benzyl ethers using zinc (Ii) trifluoromethanesulfonate

Deprotection is significant and conducted over mild reaction conditions, in order to restrict any more side reactions with sensitive functional groups as well as racemization or epimerization of stereo center because the protective groups are often cleaved at last stage in the synthesis. P-Methoxy benzyl (PMB) ether appears unique due to its easy introduction and removal than the other benzyl ether protecting groups. A facile, efficient and highly selective cleavage of P-methoxy benzyl ethers was reported by using 20 mole% Zinc (II) Trifluoromethanesulfonate at room temperature in acetonitrile solvent over 15-120 min. time period. To study the generality of this methodology, several PMB ethers were prepared from a variety of substrates having different protecting groups and subjected to deprotection of PMB ethers using Zn(OTf)2 in acetonitrile. In this methodology, zinc triflate cleaves only PMB ethers without affecting acid sensitivity, base sensitivity and also chiral epoxide groups.