What is the rel-(1R,4E,pR)-Cyclooct-4-enol?

rel-(1R,4E,pR)-Cyclooct-4-enol is , while it's Molecular Formula is C 8 H 14 O. Hydroxyl modified cyclooctene derivative. Cyclooctenes are useful in strain-promoted copper-free click chemistry cycloaddition reactions with 1,2,4,5-tetrazines. This cyclooctene will react with tetrazine functionalized compounds or biomolecules without the need for a catalyst to result in a stable covalent linkage. The 4+2 inverse electron demand Diels-Alder cycloaddition between trans-cyclooctene and tetrazines is the fastest biologically compatible ligation technology reported and has had many applications in biological labeling and imaging.

What is the CAS number for rel-(1R,4E,pR)-Cyclooct-4-enol?

The CAS number of rel-(1R,4E,pR)-Cyclooct-4-enol is 85081-69-2.

What is rel-(1R,4E,pR)-Cyclooct-4-enol (85081-69-2) used for?

TCO-OH is a TCO intermediate allowed for further derivatizion

What is the rel-(1R,4E,pR)-Cyclooct-4-enol?

rel-(1R,4E,pR)-Cyclooct-4-enol is , while it's Molecular Formula is C 8 H 14 O. Hydroxyl modified cyclooctene derivative. Cyclooctenes are useful in strain-promoted copper-free click chemistry cycloaddition reactions with 1,2,4,5-tetrazines. This cyclooctene will react with tetrazine functionalized compounds or biomolecules without the need for a catalyst to result in a stable covalent linkage. The 4+2 inverse electron demand Diels-Alder cycloaddition between trans-cyclooctene and tetrazines is the fastest biologically compatible ligation technology reported and has had many applications in biological labeling and imaging.

What is the CAS number for rel-(1R,4E,pR)-Cyclooct-4-enol?

The CAS number of rel-(1R,4E,pR)-Cyclooct-4-enol is 85081-69-2.

What is rel-(1R,4E,pR)-Cyclooct-4-enol (85081-69-2) used for?

TCO-OH is a TCO intermediate allowed for further derivatizion

Product classification

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85081-69-2

Product Name:(E)-Cyclooct-4-enol
Molecular Weight:126.199

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Product Details

Purity:99%

Manufacturers supply cost-effective and customizable (E)-Cyclooct-4-enol 85081-69-2

Molecular Formula:C₈H₁₄O
Molecular Weight:126.199
Boiling Point:202.2±29.0 °C(Predicted)
PKA:15.13±0.20(Predicted)
Density:0.954±0.06 g/cm3(Predicted)

85081-69-2 Relevant articles

A Simple, Readily Accessible, and Effective Apparatus for the Photoisomerization of cis -Cyclooctenes to trans -Cyclooctenes

Pickel, Thomas C.,Genung, Nathan E.,Guckian, Kevin M.,Shi, Xianglin

supporting information, p. 1711 - 1713 (2021/08/10)

A simple, cost effective, and readily ac...

General, Divergent Platform for Diastereoselective Synthesis of trans-Cyclooctenes with High Reactivity and Favorable Physiochemical Properties**

Pigga, Jessica E.,Rosenberger, Julia E.,Jemas, Andrew,Boyd, Samantha J.,Dmitrenko, Olga,Xie, Yixin,Fox, Joseph M.

supporting information, p. 14975 - 14980 (2021/05/31)

trans-Cyclooctenes (TCOs) are essential ...

A Bioorthogonal Click Chemistry Toolbox for Targeted Synthesis of Branched and Well-Defined Protein–Protein Conjugates

Baalmann, Mathis,Bitsch, Sebastian,Deweid, Lukas,Ilkenhans, Nadja,Kolmar, Harald,Neises, Laura,Schneider, Hendrik,Werther, Philipp,Wilhelm, Jonas,Wolfring, Martin,Wombacher, Richard,Ziegler, Michael J.

supporting information, p. 12885 - 12893 (2020/06/02)

Bioorthogonal chemistry holds great pote...

Optimization of IEDDA bioorthogonal system: Efficient process to improve trans-cyclooctene/tetrazine interaction

Béquignat, Jean-Baptiste,Boucheix, Claude,Canitrot, Damien,Chezal, Jean-Michel,Degoul, Fran?oise,Miot-Noirault, Elisabeth,Moreau, Emmanuel,Navarro-Teulon, Isabelle,Quintana, Mercedes,Rondon, Aurélie,Taiariol, Ludivine,Ty, Nancy

supporting information, (2020/07/21)

The antibody pretargeting approach for r...

85081-69-2 Process route

: 79643-80-4,85051-12-3
(+/-)-trimethyl(9-oxabicyclo[6.1.0]non-1-yl)silane

: 24454-38-4
cis-bicyclo[3.3.0]octan-endo-2-o1

: 1700-10-3
1,3-cyclooctadiene

: 4277-34-3,31598-74-0,39637-78-0,39637-79-1,39638-01-2,85081-69-2
rel-(1R-4E-pR)-cyclooct-4-enol

: 85081-70-5
(E)-5-Methoxy-cyclooctene

Conditions

Conditions	Yield
With methanol; sulfuric acid; at 80 ℃; for 0.333333h; Yield given. Further byproducts given; 3 and 4 not separated;	46 % Chromat.

: 4277-34-3
(Z)-cyclooct-4-enol

: 4277-34-3,31598-74-0,39637-78-0,39637-79-1,39638-01-2,85081-69-2
rel-(1R-4E-pR)-cyclooct-4-enol

Conditions

Conditions	Yield
With benzoic acid methyl ester; for 12h; Irradiation;	77%
With benzoic acid methyl ester; In diethyl ether; n-heptane; for 8h; Irradiation;	76%
With benzoic acid methyl ester; In diethyl ether; for 8h; Photolysis;	72%
With benzoic acid methyl ester; Inert atmosphere; UV-irradiation;	51%
With silica gel; In diethyl ether; hexane; Inert atmosphere; UV-irradiation; Flow reactor;	47%
With benzoic acid methyl ester; In diethyl ether; for 4h; UV-irradiation;	42%
With benzoic acid methyl ester; In diethyl ether; hexane; at 20 ℃; UV-irradiation;	40%
With benzoic acid methyl ester; In diethyl ether; hexane; at 20 ℃;	40%
With benzoic acid methyl ester; In diethyl ether; cyclohexane; for 8h; UV-irradiation; Cooling with ice;	23%
With benzoic acid methyl ester; In diethyl ether; hexane; for 6h; UV-irradiation;
In diethyl ether; cyclohexane; at 20 ℃; for 6h; UV-irradiation;
With benzoic acid methyl ester; In diethyl ether; hexane; for 6h; UV-irradiation;

85081-69-2 Upstream products

39637-80-4
(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (Z)-(R)-cyclooct-4-enyl ester
79643-80-4
(+/-)-trimethyl(9-oxabicyclo[6.1.0]non-1-yl)silane
4277-34-3
(Z)-cyclooct-4-enol
1018976-12-9
5-hydroxy-1-cyclooctene

85081-69-2 Downstream products

56-89-3
cysteine disulfide
4277-34-3
(Z)-cyclooct-4-enol
1354323-64-0
rel-(1R-4E-pS)-cyclooct-4-ene-1-yl (4-nitrophenyl) carbonate

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