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663107

Sigma-Aldrich

(2S,5S)-(−)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone

97%

동의어(들):

(2S,5S)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinone, (2S,5S)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone

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크기 선택

500 MG
₩287,448
1 G
₩546,172

₩287,448

출고 가능일2025년 4월 18일세부사항

벌크 견적 요청
모든 사진(2)

크기 선택

보기 변경
500 MG
₩287,448
1 G
₩546,172

About This Item

실험식(Hill 표기법):
C15H22N2O
CAS Number:
346440-54-8
Molecular Weight:
246.35
MDL number:
MFCD03426982
UNSPSC 코드:
12352005
PubChem Substance ID:
24884185
NACRES:
NA.22

₩287,448

출고 가능일2025년 4월 18일세부사항

벌크 견적 요청

분석

97%

양식

solid

mp

93-100 °C (lit.)

작용기

phenyl

SMILES string

CN1[C@H](N[C@@H](Cc2ccccc2)C1=O)C(C)(C)C

InChI

1S/C15H22N2O/c1-15(2,3)14-16-12(13(18)17(14)4)10-11-8-6-5-7-9-11/h5-9,12,14,16H,10H2,1-4H3/t12-,14-/m0/s1

InChI key

SKHPYKHVYFTIOI-JSGCOSHPSA-N

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관련 카테고리

일반 설명

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a chiral imidazolidinone organocatalyst, developed by MacMillan and co-workers.[1]

애플리케이션

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a second-generation MacMillan catalyst, which can be used as a chiral organocatalyst in:
  • The chiral transformation reaction, including Friedel-Crafts and Mukaiyama-Michael reactions.[2]
  • The preparation of substituted spiroundecenetriones via asymmetric domino Knoevenagel/Diels-Alder reactions.[3]
  • The asymmetric synthesis of β-hydroxy aldehydes and their dimethylacetals via aldehyde-aldehyde aldol condensation reaction.[4]
  • The enantioselective α-fluorination of aldehydes using N-fluorobenzenesulfonamide as a fluorinating agent.[5]
  • The stereoselective preparation of (oxomethyl)oxabicyclo[3.2.1]octenones and tricyclic pyrroles via [4+3] cycloaddition of (trialkylsiloxy)pentadienals to furans.[6]

Metal-free OrganoCatalyst technology for asymmetric catalysis. Catalyzes asymmetric indole alkylations, Friedel-Crafts alkylations, and a broad range of conjugate addition reactions in high enantiomeric excess.

특징 및 장점

Advantages of MacMillan imidazolidinone organocatalysts:[1]
  • Superior enantiocontrol in numerous transformations
  • High activities at low catalyst loadings
  • Extraordinary functional group tolerance

법적 정보

U.S. Pat. 6,369,243 and related patents apply. For research purposes only.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves, type N95 (US)

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시험 성적서(COA)

Lot/Batch Number
MKCL0239
MKCB9631
MKCC0040
MKBR2222V
MKBL8730V

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문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

The Importance of Iminium Geometry Control in Enamine Catalysis: Identification of a New Catalyst Architecture for Aldehyde-Aldehyde Couplings
Mangion IK, et al.
Angewandte Chemie (International Edition in English), 116(48), 6890-6892 (2004)
Teresa D Beeson et al.
Science (New York, N.Y.), 316(5824), 582-585 (2007-03-31)
The asymmetric alpha-addition of relatively nonpolar hydrocarbon substrates, such as allyl and aryl groups, to aldehydes and ketones remains a largely unsolved problem in organic synthesis, despite the wide potential utility of direct routes to such products. We reasoned that
Asymmetric organocatalysis of 4+ 3 cycloaddition reactions
Harmata M, et al.
Journal of the American Chemical Society, 125(8), 2058-2059 (2003)
Organocatalytic Asymmetric Domino Knoevenagel/Diels-Alder Reactions: A Bioorganic Approach to the Diastereospecific and Enantioselective Construction of Highly Substituted Spiro [5, 5] undecane-1, 5, 9-triones
Ramachary DB, et al.
Angewandte Chemie (International Edition in English), 42(35), 4233-4237 (2003)
Nick A Paras et al.
Journal of the American Chemical Society, 124(27), 7894-7895 (2002-07-04)
The first enantioselective organocatalytic alkylation of electron-rich benzene rings with alpha,beta-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective construction of benzylic stereogenicity, an important chiral synthon for natural product and
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문서

Macmillan Imidazolidinone Organocatalysts

Discover Professor David MacMillan's groundbreaking metal-free asymmetric catalysis using imidazolidinone-based organocatalysts for versatile transformations.

질문

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활성 필터

자사의 과학자팀은 생명 과학, 재료 과학, 화학 합성, 크로마토그래피, 분석 및 기타 많은 영역을 포함한 모든 과학 분야에 경험이 있습니다..

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