15431-03-5

Basic information

• Product Name: 3-Methyl-1-morpholino-1-propene
• Synonyms: 1-Morpholino-1-butene;3-Methyl-1-morpholino-1-propene;4-(1-Butenyl)morpholine;4-(1-buten-1-yl)Morpholine
• CAS NO: 15431-03-5
• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.21
• Mol File: 15431-03-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Methyl-1-morpholino-1-propene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-1-morpholino-1-propene(15431-03-5)
• EPA Substance Registry System: 3-Methyl-1-morpholino-1-propene(15431-03-5)

Safety Data

• Hazardous Substances Data: 15431-03-5(Hazardous Substances Data)

Usage

General Description

3-Methyl-1-morpholino-1-propene, also known as MMP, is a chemical compound with the molecular formula C8H15NO. It is commonly used as a monomer in the production of polycarboxylate superplasticizers, which are concrete admixtures that improve workability, strength, and durability of concrete. MMP is a colorless liquid with a pungent odor and is considered to be a flammable and potentially hazardous substance. It is also used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. Additionally, MMP has been found to have anti-inflammatory and analgesic properties, and it is being studied for its potential medical applications.

Upstream product

• 110-91-8 morpholine 
• 123-72-8 butyraldehyde 

Downstream Products

• 1905-28-8 2-(1-ethyl-2-morpholin-4-yl-vinyl)-benzene-1,4-diol 
• 111922-89-5 1-(2,4-Dinitro-phenyl)-2-[1-morpholin-4-yl-meth-(E)-ylidene]-butan-1-one 
• 145326-19-8 4-[(4R,5S)-5-Ethyl-3-(2-nitro-phenyl)-4,5-dihydro-3H-[1,2,3]triazol-4-yl]-morpholine 
• 79379-53-6 5-Ethyl-6-morpholin-4-yl-3-phenyl-5,6-dihydro-4H-[1,2]oxazine 
• 105423-46-9 4-((E)-2-Phenylselanyl-but-1-enyl)-morpholine 
• 113290-21-4 N-(6-Ethyl-4-oxo-7-p-tolyl-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide 
• 111922-88-4 2-[1-Morpholin-4-yl-meth-(E)-ylidene]-1-(4-nitro-phenyl)-butan-1-one 
• 66757-48-0 methyl 4-formylhexanoate 
• 111922-90-8 2-[1-Morpholin-4-yl-meth-(E)-ylidene]-1-(2-nitro-phenyl)-butan-1-one 
• 145326-24-5 [1-Morpholin-4-yl-but-(E)-ylidene]-(2-nitro-phenyl)-amine 
• 142327-76-2 3-nitro-5-ethyl-6-benzyloxymethylpyridin-2(1H)-one 

Relevant articles and documents

Rhodium(III)/Amine Synergistically Catalyzed Enantioselective Alkylation of Aldehydes with α,β-Unsaturated 2-Acyl Imidazoles

A synergistic catalysis combination of chiral-at-metal rhodium complex and amine catalyst was developed for enantioselective alkylation of aldehydes with α,β-unsaturated 2-acyl imidazoles. The corresponding adducts were obtained in good yields with excellent enantioselectivities (up to 99% ee).

Three-Step One-Pot Process of 3-Methyl-5-Benzofuranol from Amine, Aldehydes, and p-Benzoquinone

3-Methyl-5-benzofuranol was prepared by a one-pot process from morpholine, propionaldehyde, and p-benzoquinone in 85-87% isolated yields. Avoiding the tedious multistep isolation and purification operations, this practical and efficient process dramatically enhanced the production efficiency as well as reduced the amount of chemical wastes of reaction. The scale-up results showed that the performance was maintained, suggesting potential large-scale applications. Furthermore, the synthesis strategy showed high efficiency for a wide range of aliphatic aldehydes and ketone derivatives.

Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile

In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control β-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H … π interactions with Trp105 and Phe178 residues compared to the control β-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation.