49850-32-0

Basic information

• Product Name: ethyl 4-(1H-indol-3-yl)butanoate
• CAS NO: 49850-32-0
• Molecular Formula: C₁₄H₁₇NO₂
• Molecular Weight: 231.2903
• Mol File: 49850-32-0.mol

Chemical Properties

• Boiling Point: 393.8°C at 760 mmHg
• Flash Point: 191.9°C
• Density: 1.132g/cm³
• Vapor Pressure: 2.08E-06mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: ethyl 4-(1H-indol-3-yl)butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-(1H-indol-3-yl)butanoate(49850-32-0)
• EPA Substance Registry System: ethyl 4-(1H-indol-3-yl)butanoate(49850-32-0)

Safety Data

• Hazardous Substances Data: 49850-32-0(Hazardous Substances Data)

Upstream product

• 27983-42-2 5-carboethoxypentanal 
• 59-88-1 phenylhydrazine hydrochloride 
• 100-63-0 phenylhydrazine 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 133-32-4 4-indol-3-yl-butyric acid 
• 5299-60-5 6-hydroxy-hexanoic acid ethyl ester 
• 64-17-5 ethanol 
• 64802-52-4 4-(2,3-dihydro-indol-3-yl)-butyric acid ethyl ester 

Downstream Products

• 221188-37-0 4-[1-(4-fluoro-benzyl)-1H-indol-3-yl]-butyric acid ethyl ester 
• 3364-37-2 4-(1H-indol-3-yl)butan-1-ol 
• 21903-93-5 4-(1H-indol-3-yl)butyl 4-methylbenzenesulfonate 
• 1592-62-7 1-hydroxy-1,2,3,4-tetrahydrocarbazole 

Relevant articles and documents

Rhodium-Catalyzed C?H Functionalization of Indoles with Diazo Compounds: Synthesis of Structurally Diverse 2,3-Fused Indoles

A Rhodium-catalyzed C2-H functionalization of indoles with diazo compounds, followed by intramolecular nucleophilic addition to C=O or C=C bonds, is reported for divergent synthesis of 2,3-fused indoles. Besides acceptor/acceptor diazo compounds, donor/acceptor diazo compounds are broadly tolerated, giving various 2,3-fused indoles with perfect diastereocontrol. Notably, a selective C?H dialkylation reaction at C2 and C7 position of indoles has also been developed by simply changing the reaction conditions. This environmentally benign transformation proceeds under mild conditions and gives dinitrogen as the only by-product. (Figure presented.).

Indole based oxadiazole derivatives, preparation method therof

The present invention provides an indole-based oxadiazole derivative, an optical isomer thereof, or a pharmaceutically acceptable salt thereof. The indole-based oxadiazole derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof according to the present invention has little cytotoxicity and effectively inhibits urease activity, thereby exhibiting an excellent effect in the prevention or treatment of diseases related to urease activity or diseases caused by Helicobacter pylori.

Synthesis of CF3-Containing Spirocyclic Indolines via a Red-Light-Mediated Trifluoromethylation/Dearomatization Cascade

A red-light-mediated nPr-DMQA+-catalyzed cascade intramolecular trifluoromethylation and dearomatization of indole derivatives with Umemoto's reagent has been developed. This protocol provides a facile and efficient approach for the construction of functionalized and potentially biologically important CF3-containing 3,3-spirocyclic indolines with moderate to high yields and excellent diastereoselectivities under mild conditions. The success of multiple gram-scale (1 and 10 g) experiments further highlights the robustness and practicality of this protocol and the merit of the employment of red light. Mechanistic studies support the formation of a crucial CF3 radical species and a dearomatized benzyl carbocation intermediate.

METHODS AND MATERIALS FOR INCREASING OR MAINTAINING NICOTINAMIDE MONONUCLEOTIDE ADENYLYL TRANSFERASE-2 (NMNAT2) POLYPEPTIDE LEVELS

This document provides methods and materials for increasing or maintaining NMNAT2 polypeptide levels within cells. For example, compounds (e.g., organic compounds) having the ability to increase or maintain NMNAT2 polypeptide levels within cells, formulations containing compounds having the ability to increase or maintain NMNAT2 polypeptide levels within cells, methods for making compounds having the ability to increase or maintain NMNAT2 polypeptide levels within cells, methods for making formulations containing compounds having the ability to increase or maintain NMNAT2 polypeptide levels within cells, methods for increasing or maintain NMNAT2 polypeptide levels within cells, and methods for treating mammals (e.g., humans) having a condition responsive to an increase in NMNAT2 polypeptide levels are provided (or for preventing said condition).

Convergent synthesis, free radical scavenging, Lineweaver-Burk plot exploration, hemolysis and in silico study of novel indole-phenyltriazole hybrid bearing acetamides as potent urease inhibitors

In the current paper, through a convergent multi-step approach, a library of novel indole-phenyltriazole hybrids containing an amide moiety (9a-k) was synthesized. The structural verification of all synthesized molecules was accomplished by CHN and spectral analyses data. These synthesized bi-heterocyclic derivatives (9a-k) were evaluated for their anti-ulcer potential by inhibitory action against Jack bean urease enzyme and subsequently their structure-activity relationship was perceived. Moreover, these compounds were inspected for cytotoxic profile by hemolytic activity and it was professed that nearly all the synthesized compounds showed low cytotoxicity. In addition, free radical scavenging activity and kinetic analysis were also carried out for these compounds to understand their mode of inhibition. So, it was summated that these derivatives might lead to further research gateways for obtaining better and safe anti-ulcer agents.

Bi-heterocyclic benzamides as alkaline phosphatase inhibitors: Mechanistic comprehensions through kinetics and computational approaches

Novel bi-heterocyclic benzamides were synthesized by sequentially converting 4-(1H-indol-3-yl)butanoic acid (1) into ethyl 4-(1H-indol-3-yl)butanoate (2), 4-(1H-indol-3-yl)butanohydrazide (3), and a nucleophilic 5-[3-(1H-indol-3-yl)propyl]-1,3,4-oxadiazole-2-thiol (4). In a parallel series of reactions, various electrophiles were synthesized by reacting substituted anilines (5a–k) with 4-(chloromethyl)benzoylchloride (6) to afford 4-(chloromethyl)-N-(substituted-phenyl)benzamides (7a–k). Finally, the nucleophilic substitution reaction of 4 was carried out with newly synthesized electrophiles, 7a–k, to acquire the targeted bi-heterocyclic benzamides, 8a–k. The structural confirmation of all the synthesized compounds was done by IR, 1H NMR, 13C NMR, EI-MS, and CHN analysis data. The inhibitory effects of these bi-heterocyclic benzamides (8a–k) were evaluated against alkaline phosphatase, and all these molecules were identified as potent inhibitors relative to the standard used. The kinetics mechanism was ascribed by evaluating the Lineweaver–Burk plots, which revealed that compound 8b inhibited alkaline phosphatase non-competitively to form an enzyme–inhibitor complex. The inhibition constant Ki calculated from Dixon plots for this compound was 1.15 μM. The computational study was in full agreement with the experimental records and these ligands exhibited good binding energy values. These molecules also exhibited mild cytotoxicity toward red blood cell membranes when analyzed through hemolysis. So, these molecules might be deliberated as nontoxic medicinal scaffolds to render normal calcification of bones and teeth.

Novel indole based hybrid oxadiazole scaffolds with: N -(substituted-phenyl)butanamides: Synthesis, lineweaver-burk plot evaluation and binding analysis of potent urease inhibitors

In the study presented herein, 4-(1H-indol-3-yl)butanoic acid (1) was sequentially transformed in the first phase into ethyl 4-(1H-indol-3-yl)butanoate (2), 4-(1H-indol-3-yl)butanohydrazide (3) and 5-[3-(1H-indol-3-yl)propyl]-1,3,4-oxadiazole-2-thiol (4)

New indole based hybrid oxadiazole scaffolds with N-substituted acetamides: As potent anti-diabetic agents

Current study is based on the sequential conversion of indolyl butanoic acid (1) into ethyl indolyl butanoate (2), indolyl butanohydrazide (3), and 1,3,4-oxadiazole-2-thiol analogs (4) by adopting chemical transformations. In a parallel series of reaction

Catalytic Enantioselective Synthesis of Tetrahydocarbazoles and Exocyclic Pictet-Spengler-Type Reactions

A synthetic strategy for the synthesis of chiral tetrahydrocarbazoles (THCAs) has been developed. The strategy relies on two types of 6-exo-trig cyclization of 3-substituted indole substrates. Enantioselective domino Friedel-Crafts-type reactions leading to THCAs can be catalyzed by chiral phosphoric acid derivatives (with up to >99% ee), and the first examples of exocyclic Pictet-Spengler reactions to form THCAs are reported.