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1700-10-3

  • Product Name:(1Z,3Z)-Cycloocta-1,3-diene
  • Molecular Formula:C8H12
  • Molecular Weight:108.183
  • Appearance:colourless liquid
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Product Details

pd_meltingpoint:-53 – -51 °C

Appearance:colourless liquid

Purity:99%

Cost-effective customized wholesale (1Z,3Z)-Cycloocta-1,3-diene 1700-10-3

  • Molecular Formula:C8H12
  • Molecular Weight:108.183
  • Appearance/Colour:colourless liquid 
  • Vapor Pressure:4.98mmHg at 25°C 
  • Melting Point:-53 – -51 °C 
  • Refractive Index:n20/D 1.494  
  • Boiling Point:150.1 °C at 760 mmHg 
  • Flash Point:25.1 °C 
  • PSA:0.00000 
  • Density:0.841 g/cm3 
  • LogP:2.67280 

1,3-Cyclooctadiene(Cas 1700-10-3) Usage

General Description

1,3-Cyclooctadiene, particularly its (Z,Z)-isomer, can undergo enantiodifferentiating photoisomerization to produce chiral (E,Z)-1,3-cyclooctadiene with significant enantiomeric excess (up to 18% ee) when sensitized by chiral aromatic carboxylates, such as (-)-menthyl benzenehexacarboxylate, in nonpolar solvents. The process is highly sensitive to solvent polarity, with polar solvents diminishing enantioselectivity, likely due to radical ionic intermediates. The resulting optically active (E,Z)-isomer exhibits exceptionally high specific rotation and circular dichroism, confirming theoretical predictions about its chiroptical properties. Supramolecular systems, such as γ-cyclodextrin-based rotaxanes, further enhance enantioselectivity (up to 15.3% ee) by providing chiral binding sites for sensitization.

InChI:InChI=1/C8H12/c1-2-4-6-8-7-5-3-1/h1-4H,5-8H2

1700-10-3 Relevant articles

Enantiodifferentiation in the Photoisomerization of (Z,Z)-1,3-Cyclooctadiene in the Cavity of γ-Cyclodextrin-Curcubit[6]uril-Wheeled [4]Rotaxanes with an Encapsulated Photosensitizer

Yan, Zhiqiang,Huang, Qinfei,Liang, Wenting,Yu, Xingke,Zhou, Dayang,Wu, Wanhua,Chruma, Jason J.,Yang, Cheng

, p. 898 - 901 (2017)

A biphenyl photosensitizer axle was impl...

Optically active (E,Z)-1,3-cyclooctadiene: First enantioselective synthesis through asymmetric photosensitization and chiroptical property

Inoue, Yoshihisa,Tsuneishi, Hiroshi,Hakushi, Tadao,Tai, Akira

, p. 472 - 478 (1997)

Enantiodifferentiating photoisomerizatio...

Resolution, Circular Dichroism Spectrum, Molecular Structure, and Absolute Configuration of cis,trans-1,3-Cyclooctadiene

Isaksson, Roland,Roschester, Jan,Sandstroem, Jan,Wistrand, Lars-Goeran

, p. 4074 - 4075 (1985)

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Enantiodifferentiating photoisomerization of (Z, Z)-1,3-cyclooctadiene included and sensitized by naphthoyl-curdlan

Fukuhara, Gaku,Imai, Mami,Yang, Cheng,Mori, Tadashi,Inoue, Yoshihisa

supporting information; experimental part, p. 1856 - 1859 (2011/06/22)

6-O-(2-Naphthoyl)curdlan was newly synth...

1700-10-3 Process route

tetrahydrofuran
109-99-9,24979-97-3,77392-70-2

tetrahydrofuran

1,3-cyclooctadiene
3806-59-5

1,3-cyclooctadiene

bicyclo[3.3.0]oct-2-ene
5549-09-7

bicyclo[3.3.0]oct-2-ene

cyclooctadienyl anion
1700-10-3,3806-59-5,3806-60-8,96612-29-2,96612-30-5

cyclooctadienyl anion

4-Ethylbicyclo<3.3.0>oct-2-en
87291-52-9

4-Ethylbicyclo<3.3.0>oct-2-en

Conditions
Conditions Yield
With [(trimethylsilyl)methyl]potassium; at 0 ℃; Mechanism; Product distribution;
1-trimethylsilyl-cis-cyclo-octene
79643-79-1

1-trimethylsilyl-cis-cyclo-octene

1,3-cyclooctadiene
1700-10-3

1,3-cyclooctadiene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 84.7 percent / m-chloroperbenzoic acid, disodium hydrogen phosphate / CH2Cl2 / 1 h
2: conc. H2SO4, MeOH / 0.33 h / 80 °C / 3 and 4 not separated
With methanol; disodium hydrogenphosphate; sulfuric acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

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    1-trimethylsilyl-cis-cyclo-octene

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    tetrahydrofuran

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