138647-49-1

Basic information

• Product Name: 1-(tertbutoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yltrifluoromethanesulfonate
• Synonyms: 1-(tertbutoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yltrifluoromethanesulfonate;TERT-BUTYL 4-(TRIFLUOROMETHYLSULFONYLOXY)-5,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE;3,6-Dihydro-4-[[(trifluoromethyl)sulfonyl]oxy]-1(2H)-pyridinecarboxylic acid tert-butyl ester;1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydro-4-[[(trifluoromethyl)sulfonyl]oxy]pyridine;1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-4-[[(trifluoromethyl)sulfonyl]oxy]-, 1,1-dimethylethyl ester;N-Boc-4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine;4-[(trifluoromethyl)sulfonyloxy]-5,6-dihydropyridine-1(2H)-carboxylate;tert-Butyl-4{[(trifluoroMethyl)sulfonyl]oxy}-1,2,3,6-tetrahydro-1-pyridinecarboxylate
• CAS NO: 138647-49-1
• Molecular Formula: C₁₁H₁₆F₃NO₅S
• Molecular Weight: 331.31
• Mol File: 138647-49-1.mol
• Article Data: 142

Chemical Properties

• Boiling Point: 361.24 °C at 760 mmHg
• Flash Point: 172.272 °C
• Appearance: /
• Density: 1.4 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.481
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: -3.55±0.40(Predicted)
• CAS DataBase Reference: 1-(tertbutoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yltrifluoromethanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(tertbutoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yltrifluoromethanesulfonate(138647-49-1)
• EPA Substance Registry System: 1-(tertbutoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yltrifluoromethanesulfonate(138647-49-1)

Safety Data

• Hazardous Substances Data: 138647-49-1(Hazardous Substances Data)

Usage

General Description

1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yltrifluoromethanesulfonate is a chemical compound used in organic synthesis and drug development. Its chemical structure includes a tetrahydropyridine ring and a trifluoromethanesulfonate group, which make it a versatile building block for the preparation of various pharmaceuticals and biologically active compounds. The tert-butoxycarbonyl (t-Boc) protecting group is commonly used in organic synthesis to protect amines and other reactive functional groups, making the compound suitable for use in the preparation of peptides and other complex molecules. Additionally, the presence of the trifluoromethanesulfonate group enhances the compound’s reactivity and solubility in organic solvents. Overall, this compound is valuable in the field of medicinal chemistry and organic synthesis for the development of new pharmaceuticals and research compounds.

InChI:InChI=1/C11H16F3NO5S/c1-10(2,3)19-9(16)15-6-4-8(5-7-15)20-21(17,18)11(12,13)14/h4H,5-7H2,1-3H3

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 456-64-4 phenyl trifluoromethanesulfonamide 
• 4111-54-0 lithium diisopropyl amide 
• 109-72-8 n-butyllithium 
• 108-18-9 diisopropylamine 
• 159503-90-9 C₁₀H₁₇NO₃ 
• 24424-99-5 di-tert-butyl dicarbonate 
• 41979-39-9 4-piperidone hydrochloride 
• 40906-82-9 bis(trifluoromethylsulfonyl)phenylmethane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 145100-51-2 N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide 

Downstream Products

• 138647-54-8 4-(2,4-Dichloro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 194669-38-0 2-[1-tert-butoxycarbonyl-(1.2.3.6-tetrahydropyridin-4-yl)]benzonitrile 
• 256951-75-4 4-(2-cyano-4-fluorophenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 186347-72-8 4-phenyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 370864-42-9 4-(3-cyanophenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 184368-74-9 3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester 
• 138647-51-5 4-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 138647-50-4 4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 138647-53-7 1-tert-butyloxycarbonyl-4-(4-methylphenyl)-1,2,3,6-tetrahydropyridine 

Relevant articles and documents

Structure based design of 4-(3-aminomethylphenyl)piperidinyl-1-amides: Novel, potent, selective, and orally bioavailable inhibitors of βII tryptase

Tryptase is a serine protease found almost exclusively in mast cells. It has trypsin-like specificity, favoring cleavage of substrates with an arginine (or lysine) at the P1 position, and has optimal catalytic activity at neutral pH. Current evidence suggests tryptase β is the most important form released during mast cell activation in allergic diseases. It is shown to have numerous pro-inflammatory cellular activities in vitro, and in animal models tryptase provokes broncho-constriction and induces a cellular inflammatory infiltrate characteristic of human asthma. Screening of in-house inhibitors of factor Xa (a closely related serine protease) identified β-amidoester benzamidines as potent inhibitors of recombinant human βII tryptase. X-ray structure driven template modification and exchange of the benzamidine to optimize potency and pharmacokinetic properties gave selective, potent and orally bioavailable 4-(3-aminomethyl phenyl)piperidinyl-1-amides.

Synthesis of 2-or/and 6-methylated analogues of isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) a GABAA agonist

1,2,3,6-Tetrahydropyridine-4-carboxylic acid (isoguvacine) and related 2-and/or 6-methylated analogues (1-4) were synthesized using the methoxycarbonylation [Pd(OAc)2, PPh3, CO, MeOH)] of their corresponding vinylic triflates. Analogue (5), the 6-methyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid was obtained after a reductive deoxygenation of the corresponding β-keto ester.

Nitroimidazole compound as well as preparation method and application thereof

The invention discloses a novel nitroimidazole compound as well as a preparation method and application thereof. The nitroimidazole compound has a general formula (I) shown in the specification.

Design, Synthesis, and Preclinical Efficacy of Novel Nonretinoid Antagonists of Retinol-Binding Protein 4 in the Mouse Model of Hepatic Steatosis

Retinol-binding protein 4 (RBP4) serves as a transporter for all-trans-retinol (1) in the blood, and it has been proposed to act as an adipokine. Elevated plasma levels of the protein have been linked to diabetes, obesity, cardiovascular diseases, and nonalcoholic fatty liver disease (NAFLD). Recently, adipocyte-specific overexpression of RBP4 was reported to cause hepatic steatosis in mice. We previously identified an orally bioavailable RBP4 antagonist that significantly lowered RBP4 serum levels in Abca4-/- knockout mice with concomitant normalization of complement system protein expression and reduction of bisretinoid formation within the retinal pigment epithelium. We describe herein the discovery of novel RBP4 antagonists 48 and 59, which reduce serum RBP4 levels by >80% in mice upon acute oral dosing. Furthermore, 59 demonstrated efficacy in the transgenic adi-hRBP4 murine model of hepatic steatosis, suggesting that RBP4 antagonists may also have therapeutic utility for the treatment of NAFLD.