162612-26-2

Basic information

• Product Name: 2(3H)-Furanone, 4-ethynyldihydro-3,5-dimethyl-, [3R-(3alpha,4alpha,5alpha)]- (9CI)
• Synonyms: 2(3H)-Furanone, 4-ethynyldihydro-3,5-dimethyl-, [3R-(3alpha,4alpha,5alpha)]- (9CI)
• CAS NO: 162612-26-2
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.1638
• Mol File: 162612-26-2.mol

Chemical Properties

• Melting Point: 44.5-45.5 °C
• Boiling Point: 225.1±29.0 °C(Predicted)
• Appearance: /
• Density: 1.04±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2(3H)-Furanone, 4-ethynyldihydro-3,5-dimethyl-, [3R-(3alpha,4alpha,5alpha)]- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, 4-ethynyldihydro-3,5-dimethyl-, [3R-(3alpha,4alpha,5alpha)]- (9CI)(162612-26-2)
• EPA Substance Registry System: 2(3H)-Furanone, 4-ethynyldihydro-3,5-dimethyl-, [3R-(3alpha,4alpha,5alpha)]- (9CI)(162612-26-2)

Safety Data

• Hazardous Substances Data: 162612-26-2(Hazardous Substances Data)

Upstream product

• 188911-98-0 1-(trimethylsilyl)-3(R*,S*)-methoxy-4(S)-(benzyloxy)-1-pentyne 
• 145071-98-3 (2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid 

Downstream Products

• 162612-32-0 2(R)-methyl-3(R)-<1'(S)-hydroxyethyl>-4-pentynoic acid N-(4'-methoxybenzyl)amide 
• 188923-17-3 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidin-(2Z)-ylidenemethyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 162612-34-2 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

Dihydropyrromethenones by Pd(0)-Mediated Coupling of Iodopyrroles and Acetylenic Amides. Synthesis of the A,B-Ring Segment of Phytochrome

Dihydropyrromethenone derivative 32b, which constitutes the A,B-ring segment of phytochrome (6), has been prepared in enantiomerically pure form beginning with acetylenic amide 47b and iodopyrrole 27. The key steps involved the TBAF-catalyzed 5-exo-dig cyclization of the acetylenic pyrrole 48b, followed by thia-Mitsunobu inversion of the resulting alcohol derivative 31b.

Enantioselective syntheses of (+)- and (-)-phaseolinic acid

(+)- and (-)-Phaseolinic acid (1) have been prepared in an enantioselective fashion from acetylenic acid 26 (or ent-26) by a three step sequence involving lactonization, epimerization at C3, and oxidative cleavage. 26 was obtained as a single enantiomer using a Nicholas-Schreiber reaction.

Toward the synthesis of biologically important chlorins, isobacteriochlorins, and corrins. Cyclic enamides from acetylenic amides

Cyclic enamides 1 of a type useful in the synthesis of naturally occurring chlorins, isobacteriochlorins, and corrins have been prepared by a process involving 5-exo-dig cyclization of the appropriate acetylenic amides 11. The desired cyclization is catalyzed by either n-Bu4NF or LiAl-(NHBn)4.

An Unequivocal Synthesis of the Ring-A,B Dihydropyrromethenone of Phytochrome

Dihydropyrromethenone 1b (R= p-methoxybenzyl), a potential precursor for the synthesis of phytochrome (3), has been prepared in enantiomerically pure form beginning with the homochiral acetylenic lactone 18.