187242-85-9

Basic information

• Product Name: (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one
• Synonyms: (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one
• CAS NO: 187242-85-9
• Molecular Formula: C8H15NO3
• Molecular Weight: 173.2096
• Mol File: 187242-85-9.mol
• Article Data: 36

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one(187242-85-9)
• EPA Substance Registry System: (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one(187242-85-9)

Safety Data

• Hazardous Substances Data: 187242-85-9(Hazardous Substances Data)

Usage

Description

(E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one, also known as Dimethylamino-dimethoxybutenone, is a chemical compound derived from butenone with the addition of a dimethylamino group and two methoxy groups. It is recognized for its reactivity and potential to form new chemical bonds, making it a versatile component in the synthesis of organic molecules and pharmaceuticals.

Uses

Used in Pharmaceutical Synthesis:
(E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one is used as a key intermediate in the synthesis of pharmaceuticals for its ability to facilitate the formation of new chemical bonds, contributing to the development of various drugs and chemical compounds.
Used in Organic Chemistry Research and Development:
In the field of organic chemistry, (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one serves as a building block for the creation of new materials and substances, supporting research and development efforts aimed at discovering innovative applications and products.
Used in Chemical Compound Production:
(E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one is utilized as a fundamental component in the production of a range of chemical compounds, leveraging its reactivity to enhance the synthesis process and yield of desired products.

Upstream product

• 6342-56-9 Pyruvic aldehyde dimethyl acetal 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 5815-08-7 tert-Butoxybis(dimethylamino)methane 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 165807-05-6 4-(dimethoxymethyl)pyrimidin-2-amine 
• 180869-38-9 4-(dimethoxymethyl)-N-methylpyrimidin-2-amine 
• 193747-11-4 2-propylthiopyrimidine-4-carboxaldehyde dimethyl acetal 
• 878760-47-5 4-(dimethoxymethyl)-2-(trifluoromethyl)pyrimidine 
• 914347-52-7 5-bromo-4-(dimethoxymethyl)pyrimidin-2-amine 
• 180869-36-7 4-dimethoxymethyl-2-methylsulfanylpyrimidine 
• 874279-26-2 4-(dimethoxymethyl)-2-(methylsulfonyl)pyrimidine 
• 27258-32-8 1-methyl-1H-pyrazole-3-carbaldehyde 
• 27258-33-9 1-methyl-1H-pyrazole-5-carbaldehyde 
• 175277-33-5 4-(dimethoxymethyl)-2-methylpyrimidine 
• 111573-59-2 pyrazole-3-carboxaldehyde dimethylacetal 
• 156825-33-1 4-(dimethoxymethyl)-2-(2-pyridyl)pyrimidine 
• 914348-07-5 2-cyclopropyl-4-(dimethoxymethyl)pyrimidine 
• 180869-44-7 2-acetamidopyrimidine-4-carboxaldehyde 

Relevant articles and documents

Synthesis of trans-disubstituted pyrazolylcyclopropane building blocks

Diastereoselective synthesis of trans-disubstituted pyrazolylcyclopropane building blocks (i.e. carboxylic acids and amines) is described starting from easily available pyrazolecarbaldehydes. The key step of the synthesis was Corey–Chaikowsky cyclopropanation of the corresponding α,β-unsaturated Weinreb amides. The title compounds were prepared in four or six steps and 32–60 and 17–40?% overall yields, respectively, on up to 50?g scale. The building blocks obtained are good starting points for the design of lead-like libraries; they themselves can be considered as isosteric analogs of CNS-active drug tranylcyclopropamine. Graphical abstract: [Figure not available: see fulltext.]

Discovery of S64315, a Potent and Selective Mcl-1 Inhibitor

Myeloid cell leukemia 1 (Mcl-1) has emerged as an attractive target for cancer therapy. It is an antiapoptotic member of the Bcl-2 family of proteins, whose upregulation in human cancers is associated with high tumor grade, poor survival, and resistance to chemotherapy. Here we report the discovery of our clinical candidate S64315, a selective small molecule inhibitor of Mcl-1. Starting from a fragment derived lead compound, we have conducted structure guided optimization that has led to a significant (3 log) improvement of target affinity as well as cellular potency. The presence of hindered rotation along a biaryl axis has conferred high selectivity to the compounds against other members of the Bcl-2 family. During optimization, we have also established predictive PD markers of Mcl-1 inhibition and achieved both efficient in vitro cell killing and tumor regression in Mcl-1 dependent cancer models. The preclinical candidate has drug-like properties that have enabled its development and entry into clinical trials.

Macrocyclic MCL-1 inhibitors and methods of use

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents for the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).