196597-81-6

Basic information

• Product Name: (S)-2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine
• Synonyms: (S)-2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine;(8S)-;2H-Indeno[5;4-b]furan-8-ethanaMine;8-tetrahydro-;2H-Indeno[5,4-b]furan-8-ethanaMine, 1,6,7,8-tetrahydro-, (8S)-;(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-9-yl)ethylaMine;(S)-2-(1,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethanaMine
• CAS NO: 196597-81-6
• Molecular Formula: C13H17NO
• Molecular Weight: 203.283
• EINECS: 1592732-453-0
• Product Categories: Ramelteon
• Mol File: 196597-81-6.mol

Chemical Properties

• Boiling Point: 329.637 °C at 760 mmHg
• Flash Point: 156.769 °C
• Appearance: /
• Density: 1.129
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: 2-8°C
• PKA: 10.27±0.10(Predicted)
• CAS DataBase Reference: (S)-2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine(196597-81-6)
• EPA Substance Registry System: (S)-2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine(196597-81-6)

Safety Data

• Hazardous Substances Data: 196597-81-6(Hazardous Substances Data)

Usage

Uses

Given the provided materials, specific applications of THIFEA are not detailed. However, based on its classification as a potential ligand for receptors and its study for pharmacological effects, we can infer possible uses in the following areas:
Used in Pharmaceutical Development:
THIFEA is used as a chemical entity in the development of pharmaceutical drugs due to its potential as a receptor ligand. Its interaction with specific receptors may lead to the modulation of biological processes, offering therapeutic benefits for various conditions.
Used in Research Applications:
In the field of biological and medicinal research, THIFEA serves as a valuable tool for studying receptor interactions and signaling pathways. Its chiral nature allows for investigations into the effects of stereochemistry on biological activity, contributing to a deeper understanding of molecular recognition and drug action.

InChI:InChI=1/C13H17NO/c14-7-5-10-2-1-9-3-4-12-11(13(9)10)6-8-15-12/h3-4,10H,1-2,5-8,14H2/t10-/m0/s1

Upstream product

• 196597-79-2 (E)-2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile 
• 496-16-2 2.3-dihydrobenzofuran 
• 196597-65-6 ethyl (E)-3-(2,3-dihydrobenzofuran-5-yl)-2-propenoate 
• 221530-44-5 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile 
• 196597-77-0 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one 
• 1053239-39-6 2?(1,6,7,8?tetrahydro?2H?indeno[5,4?b]furan?8?yl)ethylamine hydrochloride 
• 198707-57-2 3-(2,3-dihydro-1-benzofuran-5-yl)prop-2-enoic acid 
• 217483-05-1 ethyl 3-(2,3-dihydrobenzofuran-5-yl)acrylate 
• 1185516-79-3 (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)acetonitrile 
• 448964-37-2 2?(1,6,7,8?tetrahydro?2H?indeno[5,4?b]furan?8?yl)?1?ethylamine 
• 221530-38-7 (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)acetamide 
• 1361396-60-2 (E)-3-(2,3-dihydrobenzofuran-4-yl)acrylaldehyde 
• 1361396-61-3 (S)-dimethyl 2-(1-(2,3-dihydrobenzofuran-4-yl)-3-oxopropyl)malonate 
• 1361396-62-4 (S)-3-(2,3-dihydrobenzofuran-4-yl)-5-methoxy-4-(methoxycarbonyl)-5-oxopentanoic acid 

Downstream Products

• 196597-27-0 N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide 
• 196597-16-7 N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]acetylamide 
• 196597-26-9 ramelteon 

Relevant articles and documents

Preparation method of ramelteon

The invention belongs to the field of medicinal chemistry, and mainly relates to a (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-1-ethylamine compound represented by a formula I. The method has the advantages that the operation is simple, the steps are reduced compared with the previous method, the route is shortened, and the used solvent is single in variety, convenient to recycle and high in yield, wherein the formula I is defined in the specification.

A process for the preparation of key intermediate lei meiti amine, its preparation and use

The invention discloses critical intermediates (with the structure formula (I) ) used for preparing ramelteon. In the formula (I), A is O or S; R is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, n-pentyl, isopentyl, cyclopentyl, phenyl, benzyl or p-methoxybenzyl; and when chiral carbon exists, the chemical compounds in the formula (I) are racemate or optically active compounds. When the A in the formula (I) is O and the R in the formula (I) is ethyl, the chemical compound is the chemical compound shown as the structure formula (II). In addition, the invention further discloses a preparing method of the chemical compound shown as the formula (II) and applications of the formula (II) in preparation of the ramelteon used for treating insomnia.

The thunder-splitting method for amine intermediate

The invention aims at providing lei meiti amine intermediate resolution method. The method of the invention to low cost optical pure chiral acid split (±) - 2 - (1, 6, 7, 8 - tetrahydro - 2 H - indenyl and [5, 4 - b] furan - 8 - yl) ethylamine preparing high optical purity of the (S)- 2 - (1, 6, 7, 8 - tetrahydro - 2 H - indenyl and [5, 4 - b] furan - 8 - yl) ethylamine. This method is simple in operation, and is suitable for industrial production.

Preparation of 2 - (1, 6, 7, 8 - tetrahydro - 2H - indenyl and [5, 4 - b] furan - 8 - subunit of ethylamine

The invention discloses a method for preparing 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-idenethamine. The method comprises the following steps: (a) synthesizing a compound of a structural formula (III) by taking a compound of a structural formula (II) as an initial raw material under the conditions of certain temperature, catalyst, carbonic acid ditert-butyl ester, solvent and hydrogen source; (b) generating 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-idenethamine from the compound of the structural formula (III) under the conditions of certain temperature, acid and solvent. In addition, the invention further discloses a novel compound, namely the compound of the structural formula (III). By adopting the method, the defects that the reaction of the conventional method is hard to control, the reaction time is too long and byproducts such as secondary amine and tertiary amine are easy to produce in the reaction process, are avoided.

Preparation method of high-purity ramelteon

The invention discloses a preparation method of high-purity ramelteon. The preparation method comprises the following steps: taking 1,2,6,7-tetrahydro-8H-indene[5,4-b]furan-8-ketone as a starting material; carrying out reduction and amino protection through wittig-horner reaction; carrying out amino deprotection under an acidic condition; carrying out hydrogenation reaction; then carrying out chiral resolution and acrylation reaction, thus obtaining the ramelteon. The ramelteon obtained through the invention is high in product purity and higher in yield; and formation of impurities is inhibited.

(S) - 2 - (1, 6, 7, 8-tetrahydro -2H-indeno [5,4-B] furan-8-yl) ethylamine preparation method

A disclosed preparation method for (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-B]furan-8-yl)ethylamine comprises the following steps: (1) taking a racemate (+/-)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-B]furan-8-yl)ethylamine as a raw material, performing resolution with an optically-pure organic acid Di-p-anisoyl-L-tartaric acid in a resolution solvent, so as to obtain a salt of an organic acid, wherein the resolution solvent is more than one of methanol, ethanol, tetrahydrofuran, acetonitrile and the like, and preferably more than one of methanol, ethanol and acetonitrile; and (2) recrystallizing the obtained organic-acid salt in a solvent, so as to obtain an optically-pure (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-B]furan-8-yl)ethylamine organic-acid salt crystal, and dissolving the product obtained in the step (2) in an aqueous solution of NaOH, or extracting with toluene or dichloromethane, so as to obtain (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-B]furan-8-yl)ethylamine. The method is capable of reducing production cost, is simple in resolution operation, is a purification method avoiding subsequent reaction and tedious post-treatment and is suitable for large-scale production.

Ramelteon intermediate and preparation method thereof

The invention discloses a ramelteon intermediate and a preparation method thereof. The preparation method of a compound II comprises the following steps: in a solvent, under condition of existence of a catalyst, a compound III and hydrogen are debrominate

A novel and practical synthesis of ramelteon

An efficient and practical process for the synthesis of ramelteon 1, a sedative-hypnotic, is described. Highlights in this synthesis are the usage of acetonitrile as nucleophilic reagent to add to 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one 2 and the subsequent hydrogenation which successfully implement four processes (debromination, dehydration, olefin reduction, and cyano reduction) into one step to produce the ethylamine compound 13 where dibenzoyl-l-tartaric acid is selected both as an acid to form the salt in the end of hydrogenation and as the resolution agent. Then, target compound 1 is easily obtained from 13 via propionylation. The overall yield in this novel and concise process is almost twice as much as those in the known routes, calculated on compound 2.

Synthesis of the melatonin receptor agonist Ramelteon using a tandem C-H activation-alkylation/Heck reaction and subsequent asymmetric Michael addition

An asymmetric synthesis of the melatonin receptor agonist Ramelteon 1 has been achieved, which involved a tandem C-H activation-alkylation/Heck reaction and subsequent highly diastereoselective asymmetric Michael addition to generate the corresponding chiral intermediate, which was readily converted into Ramelteon 1 in 19% overall yield in 15 linear steps.

Stereoselective synthesis of melatonin receptor agonist ramelteon via asymmetric michael addition

Highly enantioselective asymmetric Michael addition was used to synthesize ramelteon and its analogue. The asymmetric strategy provides an efficient approach for the medicinal modification of ramelteon with high ee value.