150884-51-8

Basic information

• Product Name: (4-CYANO-BENZYLIDENE)-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: 4-CYANO-N-BOC-BENZALDIMINE;(4-CYANO-BENZYLIDENE)-CARBAMIC ACID TERT-BUTYL ESTER;Carbamic acid, N-[(4-cyanophenyl)methylene]-, 1,1-dimethylethyl ester;tert-butyl 4-cyanobenzylidenecarbamate
• CAS NO: 150884-51-8
• Molecular Formula: C₁₃H₁₄N₂O₂
• Molecular Weight: 230.26
• Mol File: 150884-51-8.mol

Chemical Properties

• Melting Point: 85-87 °C
• Boiling Point: 349.7°Cat760mmHg
• Flash Point: 165.3°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 4.63E-05mmHg at 25°C
• Refractive Index: 1.517
• PKA: -1.40±0.50(Predicted)
• CAS DataBase Reference: (4-CYANO-BENZYLIDENE)-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (4-CYANO-BENZYLIDENE)-CARBAMIC ACID TERT-BUTYL ESTER(150884-51-8)
• EPA Substance Registry System: (4-CYANO-BENZYLIDENE)-CARBAMIC ACID TERT-BUTYL ESTER(150884-51-8)

Safety Data

• Hazardous Substances Data: 150884-51-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(4-Cyano-benzylidene)-carbamic acid tert-butyl ester is used as an intermediate in the synthesis of various organic compounds for its ability to facilitate the formation of complex molecular structures.
Used in Pharmaceutical Industry:
(4-Cyano-benzylidene)-carbamic acid tert-butyl ester is used as a building block in the production of new drugs and other biologically active molecules, owing to its potential to enhance the properties and effectiveness of these compounds.
Used in Medicinal Chemistry:
(4-Cyano-benzylidene)-carbamic acid tert-butyl ester is employed as a valuable tool for researchers in medicinal chemistry, aiding in the discovery and development of novel therapeutic agents through its unique reactivity and structural features.

InChI:InChI=1/C13H14N2O2/c1-13(2,3)17-12(16)15-9-11-6-4-10(8-14)5-7-11/h4-7,9H,1-3H3/b15-9+

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 105-07-7 4-cyanobenzaldehyde 
• 4248-19-5 tert-butyl carbazate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 68014-21-1 triphenyl(t-butoxycarbonylimino)phosphorane 

Downstream Products

• 150884-56-3 N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine 
• 158807-35-3 trans-N-Boc-3-(4-cyanophenyl)oxaziridine 
• 158807-35-3 cis-N-Boc-3-(4-cyanophenyl)oxaziridine 
• 1262642-55-6 N-tert-butyl ((4-cyanophenyl)(2-(pyridin-2-yl)phenyl)methyl)carbamate 
• 1357911-88-6 tert-butyl 2-bromo-1-(4-cyanophenyl)-2-nitroethylcarbamate 
• 1357911-79-5 tert-butyl 1-(4-cyanophenyl)-2-nitroethylcarbamate 
• 188777-45-9 (S)-2-{1-benzyl-2-[(tert-butoxy)carbonyl]hydrazino}propanoic acid 
• 188777-46-0 (S)-2-{1-benzyl-2-[(tert-butoxy)carbonyl]hydrazino}-3-methylbutanoic acid 
• 163226-33-3 N-tert-butoxycarbonyl-3-(2,3,5-trichlorophenyl)oxaziridine 

Relevant articles and documents

Synthesis of highly substituted 2-spiropiperidines

2-Spiropiperidines are a highly desirable, yet under represented structure in drug discovery. 2-Spiropiperidines were synthesised in either a two-pot or one-pot reaction. In the two-pot reaction, the addition of a Weiler dianion to N-Boc imines, followed by deprotection and in situ condensation with a cyclic ketone generated functionalised 2-spiropiperidines in good to excellent yields. In the one-pot reaction, the addition of Chan's diene to N-Boc imines under Maitland-Japp conditions, followed by the addition of sodium bicarbonate and a cyclic ketone formed functionalised 2-spiropiperidines in moderate to good yields.

STEREOSELECTIVE PROCESS

The invention relates to a method for the stereoselective preparation of compounds of formula (IV).

PYRAZOLE AMIDE DERIVATIVE

The present invention relates to a novel compound having a function of inhibiting RORγ activity. The present invention also relates to pharmaceutical composition comprising the compound, a use of the compound in treating or preventing autoimmune diseases, inflammatory diseases, metabolic diseases, or cancer diseases.

Diastereo- and enantioselective Pd(II)-catalyzed additions of 2-alkylazaarenes to N -boc imines and nitroalkenes

A chiral Pd(II)-bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkylazaarenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in high yields.

Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization

The first rhodium-catalyzed arylation of imines proceeding via C-H bond functionalization is reported. Use of a non-coordinating halide abstractor is important to obtain reactivity. Aryl-branched N-Boc-amines are formed, and a wide range of functionality is compatible with the reaction.

Discovery of a new class of macrocyclic antagonists to the human motilin receptor

A novel class of macrocyclic peptidomimetics was identified and optimized as potent antagonists to the human motilin receptor (hMOT-R). Well-defined structure-activity relationships allowed for rapid optimization of potency that eventually led to high aff

N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents

This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.

Electrophilic Amination: Preparation and Use of N-Boc-3-(4-cyanophenyl)oxaziridine, a New Reagent That Transfers a N-Boc Group to N- and C-Nucleophiles

We describe the preparation of the title compound 2b via aza-Wittig reaction of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b.Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give Nβ-Boc-hydrazines) and enolates (to give N-Boc-amino drivatives).