405873-05-4

Usage

Uses

Used in Pharmaceutical Industry:
(3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE is used as a synthetic intermediate for the preparation of tricyclic steroid precursors, which are essential in the development of various pharmaceutical compounds. Its chiral nature and specific functional groups make it a valuable building block in the synthesis of biologically active molecules with potential therapeutic applications.
Used in Chemical Synthesis:
(3R)-(-)-3-(1-METHYL-1H-INDOL-3-YL)-1-BUTYRALDEHYDE is used as a substrate in the synthesis of 2-alkyl cyclohexanone intermediates, which are important in the preparation of complex organic molecules and materials. Its unique structure allows for further functionalization and modification, enabling the development of novel compounds with diverse applications in various industries.

Upstream product

• 603-76-9 1-methylindole 
• 123-73-9 trans-Crotonaldehyde 
• 123-73-9 crotonaldehyde 
• 949489-76-3 1-(1-methyl-1H-imidazol-2-yl)-3-(1-methyl-1H-indol-3-yl)-butan-1-ol 
• 860772-44-7 (R)-1-(1-methyl-1H-imidazole-2-yl)-3-(1-methyl-1H-indol-3-yl)butan-1-one 

Downstream Products

• 406920-66-9 (+/-)-3-(1-methyl-1H-indol-3-yl)butanol 
• 406920-66-9 (R)-3-(1-methyl-1H-indol-3-yl)-3-methylpropan-1-ol 

Relevant academic research and scientific papers

Highly stereoselective imidazolethiones mediated Friedel-Crafts alkylation of indole derivatives

The asymmetric Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes was promoted by the novel imidazolethiones to afford the corresponding adducts in moderate to excellent yields and high enantioselectivities under mild reaction conditions.

Enantioselective Friedel-Crafts alkylations catalysed by well-defined iridium and rhodium half-sandwich complexes

Aqua-complexes (SM,RC)-[CpM{(R)-prophos}(H 2O)][SbF6]2 (M = Rh 1, Ir 2) catalysed the alkylation of α,β-unsaturated aldehydes with aromatics and heteroaromatics but in some cases, mixtures of products

CaSH organocatalysis: Enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes

Enantioselective Friedel-Crafts alkylation of indole with α,β-unsaturated aldehyde was catalyzed by camphor sulfonyl hydrazine (CaSH) with good enantioselectivity (81-88%). Georg Thieme Verlag Stuttgart.

Enantioselective friedel-crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes

The enantioselective Friedel-Crafts addition of a variety of indoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes (Sc(III)-pybox) was accomplished utilizing a series of β-substituted α,β-unsaturated phosphonates and α,β-unsaturate

Intra- and intermolecular reactions of indoles with alkynes catalyzed by gold

Indoles react intramolecularly with alkynes in the presence of gold catalysts to give from six- to eight-membered-ring annulated compounds. The cationic AuI complex [Au(P{C6H4-(o-Ph))(tBu) 2)(NCMe)]SbF6 is the best catalyst for the formation of six- and seven-membered rings by 6-endo-dig, 6-exo-dig, and 7-exo-dig cyclizations. Indoloazocines are selectively obtained with AuCl3 as catalyst in a rare 8-endodig process. In this process alienes or tetracyclic annulated derivatives are also formed as a result of an initial fragmentation reaction. The intermolecular reaction of indoles with alkynes proceeds to form 3-alkenylated intermediates that react with a second equivalent of indole to give bisindolyl derivatives. Indoles that are substituted at the 3-position react intermolecularly with alkynes to give 2-alkenylated intermediates that can be trapped intramolecularly with the appropriate nucleophiles.

Enantioselective Friedel-Crafts alkylations of α,β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes

An enantioselective Friedel-Crafts alkylation with α,β-unsaturated 2-acyl imidazoles and electron-rich aromatic nucleophiles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes has been accomplished. These α,β-unsaturated 2-acyl imidazol

Enantioselective transformation of alpha, beta-unsaturated aldehydes using chiral organic catalysts

Nonmetallic organic catalysts are provided that facilitate the enantioselective reaction of α,β-unsaturated aldehydes. The catalysts are chiral imidazolidinone compounds having the structure of formula (IIA) or (IIB) or are acid addition salts thereof, wherein, in one preferred embodiment, R1 is C1-C6 alkyl, R2 is tri(C1-C6 alkyl)-substituted methyl, R3 and R4 are hydrogen, and R5 is phenyl optionally substituted with 1 or 2 substituents selected from the group consisting of halo, hydroxyl, and C1-C6 alkyl. The chiral imidazolidinones are useful in catalyzing a wide variety of reactions, including cycloaddition reactions, Friedel-Crafts alkylation reactions, and Michael additions.

Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis

The indole framework has become widely identified as a "privileged" structure with representation in over 3000 natural isolates and 40 medicinal agents of diverse therapeutic action. A new strategy for asymmetric access to this important pharmacaphore has