59159-39-6 Usage
Description
(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is a phosphonium salt compound that serves as a versatile reagent in organic synthesis. It is characterized by its ability to act as a source of the triphenylphosphonium ylide in various chemical reactions, facilitating the formation of new chemical bonds and structures.
Uses
Used in Pharmaceutical Industry:
(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used as a reactant for the rhodium-catalyzed asymmetric hydrogenation reactions, which are crucial for the synthesis of chiral compounds with potential pharmaceutical applications. The enantioselective reduction of prochiral substrates can lead to the production of biologically active molecules with desired stereochemistry.
Used in Organic Chemistry Research:
In the field of organic chemistry, (tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used as a reactant for the Wittig reaction, a widely employed method for the synthesis of alkenes from aldehydes and ketones. This reaction allows for the formation of carbon-carbon double bonds, which are essential structural elements in many organic compounds.
Used in Synthesis of Complex Molecules:
(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used as a reactant for Wittig methylenation, a specific type of Wittig reaction that involves the conversion of aldehydes and ketones into methylene compounds. This process is useful for the synthesis of complex organic molecules with specific structural requirements.
Used in the Preparation of Chiral Ligands:
This phosphonium salt is used in the preparation of N-(phenylmethyl)-cis-pyrrolidinediacetic acid esters via a double aza-Michael addition reaction. The resulting chiral ligands can be employed in asymmetric catalysis, enabling the selective formation of enantiomerically pure compounds.
Used in Fluorination Reactions:
(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used for the stereoselective preparation of α-fluoro-α,β-unsaturated esters. This involves deprotonation, followed by fluorination and stereoselective Wittig olefination with aldehydes, allowing for the synthesis of fluorinated compounds with specific stereochemistry.
Used in Chain Extension Reactions:
In organic synthesis, (tert-Butoxycarbonylmethyl)triphenylphosphanium bromide is used for Wittig chain extension reactions, which involve the elongation of carbon chains in organic molecules. This process is valuable for the synthesis of long-chain compounds and polymers with tailored properties.
Check Digit Verification of cas no
The CAS Registry Mumber 59159-39-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,1,5 and 9 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 59159-39:
(7*5)+(6*9)+(5*1)+(4*5)+(3*9)+(2*3)+(1*9)=156
156 % 10 = 6
So 59159-39-6 is a valid CAS Registry Number.
InChI:InChI=1/C24H26O2P/c1-24(2,3)26-23(25)19-27(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-18H,19H2,1-3H3/q+1
59159-39-6Relevant articles and documents
Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones
Feng, Xiaoming,Hu, Xinyue,Lin, Lili,Wang, Kaixuan,Xu, Chaoran,Zhou, Yuqiao
supporting information, p. 8917 - 8920 (2021/09/10)
An efficient enantioselective [3+2] cycloaddition of isomünchnones with methyleneindolinones that are generated by anin situintramolecular addition of the carbonyl group to rhodium carbenes is realized with a chiralN,N′-dioxide/Zn(ii) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values.
DMAP Mediated Efficient Construction of Functionalized Chromenes through One-Pot Reaction of para-Quinone Methides with Allenoates
Song, Zefeng,Jia, Yuping,Zhang, Daizhou,Wang, De
supporting information, p. 1942 - 1948 (2021/04/05)
A novel DMAP-mediated Rauhut-Currier/oxa-Michael addition cascade reaction of hydroxylphenyl-substituted para-quinone methide with allenoate was reported for the first time. A series of functionalized chromenes were successfully obtained with moderate to
Side-Chain Modification of Peptides Using a Phosphoranylidene Amino Acid
Accorsi, Matteo,Ahsanullah,Masri, Enaam,Rademann, J?rg
supporting information, (2020/04/15)
The flexible variation of peptidomimetics is of great interest for the identification of optimized protein ligands. Here we present a general concept for introducing side-chain modifications into peptides using triarylphosphonium amino acids. Building blo
