18521-02-3

Basic information

• Product Name: ethyl (2Z)-3-cyclohexylprop-2-enoate
• CAS NO: 18521-02-3
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.2594
• Mol File: 18521-02-3.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 246.4°C at 760 mmHg
• Flash Point: 113.4°C
• Density: 1.019g/cm³
• Vapor Pressure: 0.0272mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: ethyl (2Z)-3-cyclohexylprop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2Z)-3-cyclohexylprop-2-enoate(18521-02-3)
• EPA Substance Registry System: ethyl (2Z)-3-cyclohexylprop-2-enoate(18521-02-3)

Safety Data

• Hazardous Substances Data: 18521-02-3(Hazardous Substances Data)

Upstream product

• 16139-79-0 ethyl diphenylphosphonoacetate 
• 2043-61-0 cyclohexanecarbaldehyde 
• 623-73-4 diazoacetic acid ethyl ester 
• 188945-41-7 ethyl di-O-tolylphosphonoacetate 
• 851348-65-7 ethyl 2-(bis(2-(tert-butyl)phenoxy)phosphoryl)acetate 
• 24045-02-1 (benzothiazole-2-sulfonyl)-acetic acid ethyl ester 
• 188945-44-0 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 851348-19-1 [bis-(biphenyl-2-yloxy)-phosphoryl]-acetic acid ethyl ester 
• 851348-42-0 [bis-(2,4-di-tert-butyl-phenoxy)-phosphoryl]-acetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 623-47-2 propynoic acid ethyl ester 
• 110-82-7 cyclohexane 
• 1071-46-1 hydrogen ethyl malonate 

Downstream Products

• 673456-32-1 (Z)-3-cyclohexylpropenoic acid 
• 42134-55-4 (Z)-3-cyclohexyl-2-propene-1-ol 

Relevant articles and documents

Evidence against Reversible Wittig Reaction of a Stabilized Ylide: High (E)-Olefin Selectivity under Kinetic Control

The betaine 10, generated by deprotonation from deuterium-labeled 8-d, decomposes stereospecifically to the (Z)-alkene.The corresponding Wittig reaction of ylide 4 with cyclohexanecarboxaldehyde, which gives a 95:5 (E)-/(Z)-alkene ratio, therefore occurs under kinetic control, without equilibration or Wittig reversal.

Highly syn-selective elimination of peterson anti-adducts to give Z-α,β-unsaturated esters

Peterson adducts have been known to stereospecifically give syn-elimination products upon treatment with base except when the product olefin is in conjugation with an electron-withdrawing group. The missing piece has been put in place by using a catalytic amount of DBU, by which syn-elimination could be effected to provide the thermally less stable Z-olefin from the anti-adduct with high selectivity.

Stereoselective synthesis of either (E)- or (Z)-silyl enol ether from the same acyclic α,β-unsaturated ketone using cationic rhodium complex-catalyzed 1,4-hydrosilylation

The stereoselective synthesis of either (E)- or (Z)-silyl enol ether from the same acyclic α,β-unsaturated ketone is reported. Highly (Z)-selective conditions were the use of [Rh(cod)2]BF 4/DPPE at room temperature with no solvent, whereas (E)-selective conditions were the use of [Rh(cod)2]BF4/P(1-Nap) 3 (1-Nap = 1-naphthyl) under refluxing dichloromethane.