113439-92-2

Basic information

• Product Name: 4,4,4-trifluorobut-2-yn-1-ol
• Synonyms: 4,4,4-trifluorobut-2-yn-1-ol;4,4,4-Trifluoro-2-butyn-1-ol
• CAS NO: 113439-92-2
• Molecular Formula: C₄H₃F₃O
• Molecular Weight: 124
• Mol File: 113439-92-2.mol

Chemical Properties

• Boiling Point: 78.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.351±0.06 g/cm3(Predicted)
• PKA: 13.09±0.10(Predicted)
• CAS DataBase Reference: 4,4,4-trifluorobut-2-yn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,4-trifluorobut-2-yn-1-ol(113439-92-2)
• EPA Substance Registry System: 4,4,4-trifluorobut-2-yn-1-ol(113439-92-2)

Safety Data

• Hazardous Substances Data: 113439-92-2(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 661-54-1 3,3,3-trifluoroprop-1-yne 

Downstream Products

• 83706-94-9 1-trifluoromethylprop-1-en-3-ol 
• 1159600-63-1 (3-phenyl-5-(trifluoromethyl)isoxazol-4-yl)methanol 
• 1236188-79-6 (3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)methanol 
• 1384267-71-3 C₁₂H₁₀F₃NO₃ 

Relevant articles and documents

Potent and Selective Agonists of Sphingosine 1-Phosphate 1 (S1P1): Discovery and SAR of a Novel Isoxazole Based Series

Sphingosine 1-phosphate (S1P) is the endogenous ligand for the sphingosine 1-phosphate receptors (S1P1-5) and evokes a variety of cellular responses through their stimulation. The interaction of S1P with the S1P receptors plays a fundamental physiological role in a number of processes including vascular development and stabilization, lymphocyte migration, and proliferation. Agonism of S1P1, in particular, has been shown to play a significant role in lymphocyte trafficking from the thymus and secondary lymphoid organs, resulting in immunosuppression. This article will detail the discovery and SAR of a potent and selective series of isoxazole based full agonists of S1P1. Isoxazole 6d demonstrated impressive efficacy when administered orally in a rat model of arthritis and in a mouse experimental autoimmune encephalomyelitis (EAE) model of multiple sclerosis.

HETEROCYCLIC COMPOUNDS AS S1P1 AGONISTS FOR THE TREATMENT OF AUTOIMMUNE AND VASCULAR DISEASES

Disclosed are compounds of Formula (I) or stereoisomers, salts, or prodrugs thereof, wherein: W is CH2 or O; Q is Formula (II), Formula (III) or Formula (IV); and R1, R2, R3, R4, n, and G are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

SPHINGOSINE-1-PHOSPHATE RECEPTOR AGONISTS

Disclosed are compounds of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein: A is formula (II) Q is a substituted 5-membered monocyclic heteroaryl group; W is CH2, O, or NH; and R1, R2, R3, R4, R5, R6, m, n, t, and x are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

4 - (5 - ISOXAZOLYL OR 5 - PYRRAZOLYL -1,2,4- OXADIAZOL - 3 - YL) -MANDELIC ACID AMIDES AS SPHINGOSIN- 1 - PHOSPHATE 1 RRECEPTOR AGONISTS

Disclosed are compounds of Formula (I) or stereoisomers, salts, or prodrugs thereof, wherein: Q is, or R1 is phenyl substituted with zero to 3 substituents; and R1, R2, R3, R4, R5, and G are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

TRICYCLIC HETEROCYCLIC COMPOUNDS

Disclosed are compounds of Formula (I) or stereoisomers or salts thereof, wherein: X1, X2, X3, W, Q1, Q2, and G2 are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

SUBSTITUTED OXADIAZOLE DERIVATIVES AS S1P AGONISTS IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISEASES

Disclosed are compounds of Formula (I) [INSERT CHEMICAL STRUCTURE HERE] (I) or pharmaceutically acceptable salts thereof, wherein Q is [INSERT CHEMICAL STRUCTURE HERE] or [INSERT CHEMICAL STRUCTURE HERE]; R1 is alkyl or aryl, said aryl optionally substituted with one to five substituents independently selected from C1 to C6 alkyl, C1 to C4 haloalkyl, OR4, and/or halogen; and R2, R3, R4, and n are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

Asymmetric synthesis of both enantiomers of anti-4,4,4-trifluorothreonine and 2-amino-4,4,4-trifluorobutanoic acid

A short and efficient enantio selective synthesis of both enantiomers of anti-4,4,4-trifluorothreonine and 2-amino-4,4,4-trifluorobutanoic acid was successfully developed. Trifluoromethylation of benzyl-protected bromoalkene 4 provided key intermediate trifluoromethylated transdi-substituted alkene 2 in good yield. The sequence then involved Sharpless asymmetric dihydroxylation, nucleophilic opening of cyclic sulfate with NaN3, palladium-catalyzed selective hydrogenation, and oxidation.

Synthesis of 3-Trifluoroethylfurans by Palladium-Catalyzed Cyclization-Isomerization of (Z)-2-Alkynyl-3-trifluoromethyl Allylic Alcohols

Hydroiodonation of trifluoromethyl propargylic alcohols 1 regio- and stereoselectively produce (Z)-2-iodo-3-trifluoromethyl allylic alcohols 2. (Z)-2-Alkynyl-3-trifluoromethyl allylic alcohols 5, available through Pd(PPh3)4-mediated coupling of 2 and terminal alkynes 4, cyclize and subsequently isomerize to 3-trifluoroethylfurans 6 upon catalysis under PdCl2(CH3CN)2 in THF at 5-10°C.

Electron Delocalisation and Stabilisation in Substituted Amino- and Hydroxypropynyl Radicals

A series of aminopropynes, RCCCH2NH2 (R = H, Me, t-Bu, Me3Si), RCCCH2N(SiMe3)2, and hydroxypropynes RCCCH2OH (R = H, Me, t-Bu, Me3Si, CF3, and EtO2C), were prepared and the corresponding α-aminopropynyl and α-hydroxypropynyl radicals were examined by e.s.r. spectroscopy.For the first series, the C-N bond rotation barriers were determined from the exchange broadening in the spectra and hence radical stabilization energies were estimated.The spin distribution in these series indicated an extra delocalisation in radicals with captodative substitution.