191090-36-5 Usage
Uses
Used in Pharmaceutical Industry:
(S)-(-)-5,5-DIPHENYL-4-(TERT-BUTYL)-2-OXAZOLIDINONE is used as a chiral auxiliary reagent for the synthesis of complex organic molecules with high enantiomeric purity. Its ability to induce enantioselectivity in reactions is essential for the development of pharmaceutical compounds with desired biological activities and reduced side effects.
Used in Chemical Research:
In the field of chemical research, (S)-(-)-5,5-DIPHENYL-4-(TERT-BUTYL)-2-OXAZOLIDINONE serves as a valuable tool for the synthesis of complex organic molecules. Its specific stereochemistry allows researchers to explore novel chemical reactions and develop new methodologies for asymmetric synthesis.
Used in Material Science:
(S)-(-)-5,5-DIPHENYL-4-(TERT-BUTYL)-2-OXAZOLIDINONE can be employed in the development of new materials with specific properties. Its use in asymmetric synthesis enables the creation of materials with tailored characteristics, such as improved mechanical strength, thermal stability, or optical properties.
Used in Agrochemical Industry:
(S)-(-)-5,5-DIPHENYL-4-(TERT-BUTYL)-2-OXAZOLIDINONE is also used in the agrochemical industry for the synthesis of biologically active compounds with potential applications in pest control, crop protection, and other agricultural practices. Its ability to induce enantioselectivity in reactions allows for the development of more effective and selective agrochemicals with reduced environmental impact.
Check Digit Verification of cas no
The CAS Registry Mumber 191090-36-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,1,0,9 and 0 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 191090-36:
(8*1)+(7*9)+(6*1)+(5*0)+(4*9)+(3*0)+(2*3)+(1*6)=125
125 % 10 = 5
So 191090-36-5 is a valid CAS Registry Number.
InChI:InChI=1/C19H21NO2/c1-18(2,3)16-19(22-17(21)20-16,14-10-6-4-7-11-14)15-12-8-5-9-13-15/h4-13,16H,1-3H3,(H,20,21)/t16-/m0/s1
191090-36-5Relevant academic research and scientific papers
Hintermann, Tobias,Seebach, Dieter
, p. 2093 - 2126 (1998)
The 4-isopropyl-5,5-diphenyloxazolidinone (1) is readily prepared from (R)- or (S)-valine ester, PhMgBr, and ethyl chlorocarbonate. It has a melting point of ca. 250°, a low solubility in most organic solvents, and a C=O group which is sterically protected from nucleophilic attack. Thus, the soluble N-acyl-oxazolidinones (7-16) can be prepared from 1 with BuLi at temperatures around 0°instead of - 78°(Scheme 3), their Li enolates can be generated with BuLi, rather than with LDA, and deacylation in the final step of the procedure can be achieved with NaOH at ambient temperatures (Scheme 12), with facile recovery of the precipitating auxiliary 1 (filtering, washing, and drying). The following reactions of N-acyl-oxazolidinones from 1 have been investigated: alkylations (Scheme 4), aminomethylations and hydroxymethylations (Scheme 5), aldol additions (Schemes 6 and 7), Michael additions (Schemes 9 and 10), and a (4 + 2) cycloaddition (Scheme 11). The well-known features of reactions following the Evans methodology (yield, diastereoselectivity, dependence on conditions, counter ions, additives etc.) prevail in these transformations. Most products, however, have higher melting points and a much more pronounced crystallization tendency than those derived from conventional oxazolidinones, and can thus be purified by recrystallization, avoiding chromatography (Table 1). The disadvantage of 1 having a higher molecular weight (ca. 150 Da) than the non-phenyl-substituted auxiliary is more than compensated by the ease of its application, especially on large scale. A number of crystal structures of oxazolidinones derived from 1 and a TiCl4 complex of an oxazolidinone are described and discussed in view of the diastereoselective-reaction mechanisms.
