N-(trans-3-Hydroxy-2,2,4,4-tetramethylcyclobutyl)carbamic acid 1,1-dimethylethyl ester
[CAS# 1338812-41-1]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: N-(trans-3-Hydroxy-2,2,4,4-tetramethylcyclobutyl)carbamic acid 1,1-dimethylethyl ester
• Synonyms: tert-butyl N-(3-hydroxy-2,2,4,4-tetramethylcyclobutyl)carbamate
• Molecular Formula: C₁₃H₂₅NO₃
• Molecular Weight: 243.34
• CAS Registry Number: 1338812-41-1
• SMILES: CC1(C(C(C1O)(C)C)NC(=O)OC(C)(C)C)C

Properties

• Solubility: Slightly soluble (2.9 g/L) (25 °C), Calc.^*
• Density: 1.03±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.483, Calc.^*
• Boiling Point: 326.7±31.0 °C (760 mmHg), Calc.^*
• Flash Point: 151.4±24.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P312-P330

Discovery and Applications

N-(trans-3-Hydroxy-2,2,4,4-tetramethylcyclobutyl)carbamic acid 1,1-dimethylethyl ester is a chemical compound that belongs to the class of carbamates. This compound features a cyclobutane ring with tetramethyl groups at specific positions, a hydroxyl group at the 3-position, and a carbamic acid ester functionality. The chemical formula is C12H23NO3, and it contains a tert-butyl ester group, which is commonly used in organic synthesis to increase stability and influence the solubility and bioavailability of molecules.

The compound is known for its unique structure, which incorporates a cyclobutane ring, an unusual feature in many biologically active compounds. Cyclobutanes are often studied due to their strained ring structure, which can contribute to the reactivity and potential biological activity of the compound. The presence of the hydroxyl group on the cyclobutane ring suggests that this molecule may participate in hydrogen bonding interactions, which could influence its interaction with biological targets.

The discovery of N-(trans-3-hydroxy-2,2,4,4-tetramethylcyclobutyl)carbamic acid 1,1-dimethylethyl ester is associated with ongoing research in the area of medicinal chemistry, specifically in the development of new bioactive compounds. The ester group, in particular, can play a crucial role in modulating the pharmacokinetic properties of the compound, such as its absorption, distribution, and metabolism in biological systems.

While specific applications of N-(trans-3-hydroxy-2,2,4,4-tetramethylcyclobutyl)carbamic acid 1,1-dimethylethyl ester are not extensively documented in readily available literature, compounds of similar structure and functional groups, such as carbamates, are often investigated for their biological properties. Carbamate derivatives have been known for their wide range of uses, including insecticides, herbicides, and as intermediates in the synthesis of pharmaceutical agents.

Overall, N-(trans-3-hydroxy-2,2,4,4-tetramethylcyclobutyl)carbamic acid 1,1-dimethylethyl ester is a structurally interesting compound that could potentially contribute to drug design or other chemical applications, though further research is needed to fully establish its biological properties and potential uses.

References

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Arvinas Operations, Inc. (2022). Small molecule androgen receptor protein degraders. WO-2022011204-A1, 2022-01-13.
Priority Date: 2020-07-10.

Arvinas Operations, Inc. (2022). Androgen receptor protein degraders. WO-2022011205-A1, 2022-01- 13.
Priority Date: 2020-07-10.