462637-40-7

Basic information

• Product Name: Methyl 2-(hex-1-yn-1-yl)benzoate
• Synonyms: Methyl 2-(hex-1-yn-1-yl)benzoate;methyl 2-(hex-1-ynyl)benzoate
• CAS NO: 462637-40-7
• Molecular Formula: C₁₄H₁₆O₂
• Molecular Weight: 216.27564
• Mol File: 462637-40-7.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 328.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.04±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Methyl 2-(hex-1-yn-1-yl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-(hex-1-yn-1-yl)benzoate(462637-40-7)
• EPA Substance Registry System: Methyl 2-(hex-1-yn-1-yl)benzoate(462637-40-7)

Safety Data

• Hazardous Substances Data: 462637-40-7(Hazardous Substances Data)

Usage

Description

Methyl 2-(hex-1-yn-1-yl)benzoate is an organic compound that serves as an intermediate in the synthesis of Apigenin 5-O-β-D-Glucuronide (A426510), a metabolite of Apigenin (A726500). Methyl 2-(hex-1-yn-1-yl)benzoate plays a crucial role in various biological processes and has potential applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
Methyl 2-(hex-1-yn-1-yl)benzoate is used as an intermediate in the synthesis of Apigenin 5-O-β-D-Glucuronide, which has potential applications in the development of cancer therapeutics. Apigenin 5-O-β-D-Glucuronide has been reported to induce the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentrations by inhibiting MAP kinase activity. Additionally, it inhibits the proliferation of malignant tumor cells by G2/M arrest and induces morphological differentiation.
Furthermore, Apigenin has been reported to enhance the gap junction intracellular communication in liver cells, which may contribute to its potential use in liver-related therapies. The synthesis of Apigenin 5-O-β-D-Glucuronide through the use of Methyl 2-(hex-1-yn-1-yl)benzoate could lead to the development of novel treatments for various types of cancer and liver disorders.

Upstream product

• 610-94-6 2-bromobenzoic acid methyl ester 
• 693-02-7 hex-1-yne 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 33775-94-9 2-(methylthio)iodobenzene 

Downstream Products

• 609358-79-4 3-[2-(hex-1-ynyl)phenyl]pentan-3-ol 
• 294190-48-0 2-(1-hexyn-1-yl)-N-methoxy-N-methylbenzamide 
• 599-69-9 N,N,4-trimethylbenzenesulfonamide 
• 1190831-55-0 o-(hexyn-1-yl)benzoic acid hydrazide 
• 120870-47-5 2-(1-hexyn-1-yl)benzoic acid 
• 1314961-21-1 3-n-butyl-4-(phenylselenyl)-1H-isochromen-1-one 
• 1357469-14-7 (2E)-3-phenylprop-2-en-1-yl 2-hex-1-yn-1-ylbenzoate 
• 1357469-19-2 furan-2-ylmethyl 2-hex-1-yn-1-ylbenzoate 
• 30531-69-2 3-butylisochromen-1-one 
• 1357469-28-3 3-butyl-4-[(2E)-3-phenylprop-2-en-1-yl]-1H-isochromen-1-one 
• 1357469-30-7 4-benzyl-3-butyl-1H-isochromen-1-one 
• 1558764-09-2 (Z)-methyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-enyl)benzoate 
• 1609250-67-0 cis-methyl-2-(hex-1-en-1-yl)benzoate 
• 1311408-35-1 trans-methyl-2-(hex-1-en-1-yl)benzoate 

Relevant articles and documents

Gold-Catalyzed Amide/Carbamate-Linked N, O-Acetal Formation with Bulky Amides and Alcohols

A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.

Copper-Catalyzed Modular Access to N-Fused Polycyclic Indoles and 5-Aroyl-pyrrol-2-ones via Intramolecular N—H/C—H Annulation with Alkynes: Scope and Mechanism Probes

Copper-catalyzed intramolecular N—H/C—H annulation with alkynes has been developed. A variety of densely functionalized heterocycles, such as pyrrolo[1,2-a]indoles, indolo[1,2-c]quinazolin-2-ones, oxazolo[3,4-a]indoles, and imidazo[1,5-a]indoles, were synthesized in an atom- and step-economical manner, owing to the high modularized feature of aniline moiety, the linker moiety, as well as the alkyne moiety. By simply changing the oxidant from di-tert-butyl peroxide (DTBP) to 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), the reaction could readily be transformed to the aminooxygenation pathway, which grabs one oxygen atom from the TEMPO to generate 5-aroyl-pyrrol-2-ones. Mechanistic experiments indicate that vinyl radical is involved in this reaction and an amidyl-radical-initiated radical cascade might be responsible for this transformation.

Gold(i)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex

A benchtop-stable reagent for the catalytic Nicholas reaction was developed. By combining a propargyl dicobalt hexacarbonyl cluster with an ortho-alkynylbenzoate unit and a fluorous tag, introduction of a propargyl hexacarbonyl complex on various aromatic compounds having acid- or base-sensitive functional groups becomes possible by using a gold(i) catalyst. In addition, the presence of a fluorous tag facilitates convenient separation of the target products from byproducts.