CAS 1207355-31-4

dibenzazepine glutarylamino tetraethylene glycol acetyl pipecolate methyl ester

Other Click Chemistry Reagents

About This Compound

This category encompasses diverse reagents used across various click chemistry reactions, including activated esters, Michael acceptors, epoxides, and multi-functional building blocks. These compounds participate in thiol-ene reactions, Michael additions, ring-opening reactions, and other modular coupling strategies that meet the criteria of click chemistry — high yield, wide scope, simple conditions, and easy purification.

Molecular FormulaC20H17NO3 Molecular Weight319.36 g/mol InChIKeyKDYPHAQTQRXDCD-UHFFFAOYSA-N CAS Registry1207355-31-4 Literature Refs196 references

Synthesis Routes

Showing 3 of 12 available routes, sorted by yield.

Route 1

1 step Yield: 92%
methyl 5-(didehydrodibenzo[b,f]azocin-5(6H)-yl)-5-oxopentanoate
CAS 1207355-30-3
C21H19NO3
dibenzazepine glutarylamino tetraethylene glycol acetyl pipecolate methyl ester
Conditions With water; lithium hydroxide In tetrahydrofuran at 20℃; for 3h;
Reference Debets, Marjoke F.; Van Berkel, Sander S.; Schoffelen, Sanne; Rutjes, Floris P. J. T.; Van Hest, Jan C. M.; Van Delft, Floris L. [Chemical Communications, 2010, vol. 46, # 1, p. 97 - 99] DOI
Source Reaxys

Route 2

1 step Yield: 61%
5-[11,12-didehydrodibenzo[b,f ]azocin-5(6H)-yl]-5-oxopentanoic acid
CAS 1207355-31-4
C20H17NO3
+
1,5-bis(2-{2-[2-(azide)ethoxy]ethoxy}ethoxy)naphthalene
CAS 1033920-85-2
C18H22N6O4
+
cyclobis(paraquat-1,4-phenylene) tetrakis(hexafluorophosphate)
C36H32N4*4F6P
dibenzazepine glutarylamino tetraethylene glycol acetyl pipecolate methyl ester
Conditions In acetonitrile at 0℃; for 48.5h;
Reference Hou, Zhan-Yao; Yeniad, Bahar; Van Guyse, Joachim; Woisel, Patrice; Mullen, Kathleen M.; Rutjes, Floris P. J. T.; van Hest, Jan C. M.; Hoogenboom, Richard [European Journal of Organic Chemistry, 2017, vol. 2017, # 21, p. 3107 - 3113] DOI
Source Reaxys

Route 3

1 step Yield: —
5-[11,12-didehydrodibenzo[b,f ]azocin-5(6H)-yl]-5-oxopentanoic acid
CAS 1207355-31-4
C20H17NO3
+
aminotetraethylene glycol acetyl pipecolate methyl ester
CAS 3048192-41-9
C17H32N2O7
dibenzazepine glutarylamino tetraethylene glycol acetyl pipecolate methyl ester
Conditions With triethanolamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochlor
Reference Current Patent Assignee: YINGBAIRUI HANGZHOU BIOMEDICAL - CN117482246, 2024, A Location in patent: Paragraph 0257; 0282-0286
Source Reaxys
9 additional routes available in the full dataset. Contact us for complete synthesis route data.

Related Compounds

Other Other Click Chemistry Reagents in our catalog:

Frequently Asked Questions

What defines a reaction as "click chemistry"?

According to Sharpless (2001), click reactions must be modular, wide in scope, high-yielding, generate only inoffensive byproducts, be stereospecific, and use readily available starting materials. They should proceed under simple conditions (ideally insensitive to oxygen and water), use benign solvents, and products should be easy to isolate without chromatography.

How do I choose the right click reaction for my application?

For in vitro bioconjugation: CuAAC is the gold standard. For live-cell work: use SPAAC or IEDDA (copper-free). For protein labeling: SuFEx or Staudinger ligation. For polymer chemistry: thiol-ene or thiol-Michael. For prodrug activation: click-to-release (IEDDA-based elimination). Consider reaction speed, biocompatibility, and orthogonality requirements.

Can click reactions be performed in aqueous media?

Most click reactions are compatible with aqueous conditions. CuAAC works in water/t-BuOH mixtures. SPAAC and IEDDA proceed rapidly in pure aqueous buffer. Thiol-ene reactions can be performed in water with water-soluble photoinitiators. SuFEx reactions work in organic/aqueous biphasic systems. This aqueous compatibility is one of the key advantages of click chemistry for biological applications.

How do I confirm click reaction completeness?

For CuAAC/SPAAC: disappearance of the azide stretch at ~2100 cm⁻¹ in IR spectroscopy. For IEDDA: loss of the tetrazine UV-Vis absorption (pink color fades). General methods: TLC, HPLC, ¹H NMR (triazole peak), and mass spectrometry. For bioconjugation: SDS-PAGE with fluorescent readout or western blot.

What is the typical shelf life of click chemistry reagents?

Azides: 6–12 months at −20 °C (avoid light). Terminal alkynes: 12+ months at −20 °C. Cyclooctynes (DIBO, DBCO, BCN): 6–12 months at −20 °C (light-sensitive). Tetrazines: 6–12 months at −20 °C (light and moisture sensitive). TCO derivatives: 3–6 months at −20 °C (isomerization-prone). Sulfonyl fluorides: 12+ months at room temperature.

Last updated: July 27, 2026