37561-42-5

Basic information

• Product Name: 2,2-dimethyl-5-phenyl-1,3-dioxan-5-amine
• Synonyms: 2,2-dimethyl-5-phenyl-1,3-dioxan-5-amine
• CAS NO: 37561-42-5
• Molecular Weight: 207.272
• Mol File: 37561-42-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,2-dimethyl-5-phenyl-1,3-dioxan-5-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethyl-5-phenyl-1,3-dioxan-5-amine(37561-42-5)
• EPA Substance Registry System: 2,2-dimethyl-5-phenyl-1,3-dioxan-5-amine(37561-42-5)

Safety Data

• Hazardous Substances Data: 37561-42-5(Hazardous Substances Data)

Upstream product

• 5428-02-4 2-nitro-2-phenyl-propane-1,3-diol 
• 622-42-4 1-nitro-1-phenylmethane 
• 100-39-0 benzyl bromide 
• 37561-37-8 2,2-dimethyl-5-nitro-5-phenyl[1,3]dioxane 

Downstream Products

• 1033409-14-1 C₁₉H₂₁NO₃ 

Relevant articles and documents

Broadening antifungal spectrum and improving metabolic stablity based on a scaffold strategy: Design, synthesis, and evaluation of novel 4-phenyl-4,5-dihydrooxazole derivatives as potent fungistatic and fungicidal reagents

5-phenylthiophene derivatives exhibited excellent antifungal activity against Candida albicans, Candida tropicalis and Cryptococcus neoformans. However, optimal compound 7 was inactive against Aspergillus fumigatus and unstable in human liver microsomes in vitro with a half-life of 18.6 min. To discover antifungal agents with a broad spectrum and improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of 4-phenyl-4,5-dihydrooxazole derivatives were designed and synthesized. It was especially encouraging that compound 22a displayed significant antifungal activities against eight susceptible strains and seven FLC-resistant strains. Furthermore, the potent compound 22a could prevent the formation of fungalbiofilms and displayed satisfactory fungicidal activity. In addition, the metabolic stability of compound 22a was improved significantly, with the half-life of 70.5 min. Compound 22a was almost nontoxic to mammalian A549, MCF-7, HepG2, and 293T cells. Moreover, pharmacokinetic studies in SD rats showed that compound 22a exhibited pharmacokinetic properties with a bioavailability of 15.22% and a half-life of 4.44 h, indicating that compound 22a is worthy of further study.

Improving the metabolic stability of antifungal compounds based on a scaffold hopping strategy: Design, synthesis, and structure-activity relationship studies of dihydrooxazole derivatives

L-amino alcohol derivatives exhibited high antifungal activity, but the metabolic stability of human liver microsomes in vitro was poor, and the half-life of optimal compound 5 was less than 5 min. To improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of antifungal compounds with a dihydrooxazole scaffold was designed and synthesized. Compounds A33-A38 substituted with 4-phenyl group on dihydrooxazole ring exhibited excellent antifungal activities against C. albicans, C. tropicalis and C. krusei, with MIC values in the range of 0.03–0.25 μg/mL. In addition, the metabolic stability of compounds A33 and A34 in human liver microsomes in vitro was improved significantly, with the half-life greater than 145 min and the half-life of 59.1 min, respectively. Moreover, pharmacokinetic studies in SD rats showed that A33 exhibited favourable pharmacokinetic properties, with a bioavailability of 77.69%, and half-life (intravenous administration) of 9.35 h, indicating that A33 is worthy of further study.

Enantioselective formation of tert-alkylamines by desymmetrization of 2-substituted serinols

Novel enantioselective desymmetrization of 2-substituted 2-amino-1,3-propanediols has been established to generate asymmetric quaternary carbon centers comprising an amino group. Enantioselective as well as chemical conversion proved to be greatly dependent on the protecting group of the amino group in the substrate, desymmetrizing reagent, base, solvent, and naturally, catalyst. The highly effective desymmetrization has been implemented by using N-benzoylated substrates with benzoyl Chloride and triethylamine in the presence of tetraphenylbisoxazoline (24)-CuCl2 complex in THF at ambient temperature. An extensive survey of catalysts revealed that dimethylmalonate- bridged bisoxazoline-CuCl2 complexes were superior. Among them, the tetraphenylbisoxazoline (24)-CuCl2 complex turned out to work most efficiently with a wide array of the substrates. All the examined substrates, with the exception of 2-phenylserinol 36, were desymmetrized in the presence of 24-CuCl2 complex to give high enantioselectivities ranging from 85 to 95% ee. Complementary use of the diisopropylbisoxazoline (22)-CuCl2 complex has remedied the mediocre desymmetrization of 36 to give a significantly improved enantioselectivity from 63 to 83% ee.