59939-11-6

Basic information

• Product Name: Methyl 3-cyclopropylacrylate
• Synonyms: Methyl 3-cyclopropylacrylate
• CAS NO: 59939-11-6
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.1531
• Mol File: 59939-11-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 3-cyclopropylacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-cyclopropylacrylate(59939-11-6)
• EPA Substance Registry System: Methyl 3-cyclopropylacrylate(59939-11-6)

Safety Data

• Hazardous Substances Data: 59939-11-6(Hazardous Substances Data)

Upstream product

• 5927-18-4 trimethyl phosphonoacetate 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 2516-33-8 Cyclopropylmethanol 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 4333-56-6 cyclopropyl bromide 
• 922-67-8 propynoic acid methyl ester 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 75424-56-5 methyl (E)-6-chlorohex-2-enoate 
• 4111-54-0 lithium diisopropyl amide 

Downstream Products

• 1142214-45-6 C₃₀H₃₃FO₄ 
• 1142214-62-7 [3H]-AM 1638 
• 1393841-41-2 C₃₄H₃₇FO₄ 
• 1142223-08-2 methyl (3S)-3-cyclopropyl-3-(3-hydroxyphenyl)propanoate 
• 158956-34-4 (E)-3-cyclopropyl-2-propen-1-ol 

Relevant articles and documents

Dramatic Effect of γ-Heteroatom Dienolate Substituents on Counterion Assisted Asymmetric Anionic Amino-Cope Reaction Cascades

We report a dramatic effect on product outcomes of the lithium ion enabled amino-Cope-like anionic asymmetric cascade when different γ-dienolate heteroatom substituents are employed. For dienolates with azide, thiomethyl, and trifluoromethylthiol substituents, a Mannich/amino-Cope/cyclization cascade ensues to form chiral cyclohexenone products with two new stereocenters in an anti-relationship. For fluoride-substituted nucleophiles, a Mannich/amino-Cope cascade proceeds to afford chiral acyclic products with two new stereocenters in a syn-relationship. Bromide- and chloride-substituted nucleophiles appear to proceed via the same pathway as the fluoride albeit with the added twist of a 3-exo-trig cyclization to yield chiral cyclopropane products with three stereocenters. When this same class of nucleophiles is substituted with a γ-nitro group, the Mannich-initiated cascade is now diverted to a β-lactam product instead of the amino-Cope pathway. These anionic asymmetric cascades are solvent- and counterion-dependent, with a lithium counterion being essential in combination with etheral solvents such as MTBE and CPME. By altering the geometry of the imine double bond from E to Z, the configurations at the R1 and X stereocenters are flipped. Mechanistic, computational, substituent, and counterion studies suggest that these cascades proceed via a common Mannich-product intermediate, which then proceeds via either a chair (X = N3, SMe, or SCF3) or boat-like (X = F, Cl, or Br) transition state to afford amino-Cope-like products or β-lactam in the case of X = NO2.

IDO INHIBITORS

There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.

Manganese dioxide can oxidise unactivated alcohols under in situ oxidation-Wittig conditions

The in situ alcohol oxidation-Wittig reaction using manganese dioxide as the oxidant has been applied to semi-activated and, for the first time, unactivated alcohols to furnish the corresponding α,β-unsaturated esters.