tert-Butyl 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azaspiro[5.5]undec-8-ene-3-carboxylate

Name: tert-Butyl 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azaspiro[5.5]undec-8-ene-3-carboxylate
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CAS No. 1628502-01-1
Cat. No. CS-0863835
Purity≥97%
MDL No.MFCD22683429

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tert-Butyl 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azaspiro[5.5]undec-8-ene-3-carboxylate|CS-0863835

Structure of 1628502-01-1

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General Information

CAS No. 1628502-01-1
Cat. No. CS-0863835
Purity ≥97%
MDL No. MFCD22683429
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₃₆BNO₄
Molecular Weight 377.33
Synonym(s) None
SMILES O=C(N1CCC2(CC1)CC=C(CC2)B3OC(C)(C(C)(C)O3)C)OC(C)(C)C

Description

tert-Butyl 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azaspiro[5.5]undec-8-ene-3-carboxylate is a bench-stable boronate building block featuring a spirocyclic azaspiro framework. The tetramethylboronate moiety enables efficient Suzuki-Miyaura coupling under standard conditions. This structure integrates a sterically protected boron group with a rigid, electron-deficient core, facilitating selective functionalization in complex molecule synthesis.

Application

tert-Butyl 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azaspiro[5.5]undec-8-ene-3-carboxylate serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling with aryl and heteroaryl halides under mild conditions, while the spirocyclic azaspiro[5.5]undecane core provides structural rigidity and three-dimensional character valuable in medicinal chemistry. The tert-butyl ester facilitates straightforward deprotection to the free carboxylic acid, enhancing utility in peptide and macrocycle synthesis.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319
Precautionary Statements : P264-P270-P280-P302+P352-P362+P364-P501

Quality Control

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Computational Chemistry Data

TPSA 48
LogP 4.7454
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Functional Group Amide

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Fatty ring compounds Cyclohexane compounds

Key Words

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tert-Butyl 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azaspiro[5.5]undec-8-ene-3-carboxylate

CAS No. 1628502-01-1

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