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Merck
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669490

Sigma-Aldrich

(1R,4R,8R)-5-苄基-8-甲氧基-1,8-二甲基-2-(2′-甲基丙基)-双环[2.2.2]辛-2,5-二烯

95%

别名:

(1R,4R,8R) Carreira DOLEFIN 配体, (1R,4R,8R)-5-苄基-2-异丁基-8-甲氧基-1,8-二甲基-2-双环[2.2.2]辛-2,5-二烯

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About This Item

经验公式（希尔记法）:
C22H30O
CAS号:
948594-95-4
分子量:
310.47
MDL编号:
MFCD08702680
UNSPSC代码:
12352112
PubChem化学物质编号:
24885054

方案

95%

表单

liquid

旋光性

[α]20/D +98±5°, c = 0.7 in chloroform

反应适用性

reaction type: click chemistry

折射率

n20/D 1.5205

官能团

ether
phenyl

SMILES字符串

CO[C@]1(C)C[C@]2(C)C=C(Cc3ccccc3)[C@H]1C=C2CC(C)C

InChI

1S/C22H30O/c1-16(2)11-19-13-20-18(12-17-9-7-6-8-10-17)14-21(19,3)15-22(20,4)23-5/h6-10,13-14,16,20H,11-12,15H2,1-5H3/t20-,21+,22-/m1/s1

InChI key

ACWLDJOHMGJACE-BHIFYINESA-N

应用

Carreira DOLEFIN Ligands
(1R, 4R, 8R) Carreira DOLEFIN Ligand is a chiral diene ligand that can be used in:
  • The asymmetric Rh-catalyzed arylation of alkenylheterocycles by conjugate additions with various aryl boronic acids.
  • The enantioselective synthesis of 3,3-diarylpropanals by conjugate addition of aromatic boronic acids to cinnamaldehyde derivatives in the presence of a rhodium catalyst.
  • The asymmetric synthesis of pyrrolizidinones by rhodium-catalyzed 1,4-addition of aryl boronic acids to pyrrolidine acceptor.

包装

Bottomless glass bottle. Contents are inside inserted fused cone.

储存分类代码

10 - Combustible liquids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCC2213
MKBV8557V
MKBN3483V
MKBF0760V
MKBD5021

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Asymmetric Synthesis of 3, 3-Diarylpropanals with Chiral Diene- Rhodium Catalysts
Paquin J-F, et al.
Journal of the American Chemical Society, 127(31), 10850-10851 (2005)
Rhodium-catalyzed 1, 4-additions to enantiopure acceptors: Asymmetric synthesis of functionalized pyrrolizidinones
Zoute L, et al.
Organic Letters, 11(12), 2491-2494 (2009)
Enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylheteroarenes
Pattison G, et al.
Journal of the American Chemical Society, 132(41), 14373-14375 (2010)
Jean-François Paquin et al.
Journal of the American Chemical Society, 127(31), 10850-10851 (2005-08-04)
A general route to enantioenriched 3,3-diarylpropanals is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to cinnamaldehyde derivatives in the presence of chiral dienes. The addition of both electron-poor as well as
Jean-François Paquin et al.
Organic letters, 7(17), 3821-3824 (2005-08-12)
A general route to enantioenriched tert-butyl 3,3-diarylpropanoates is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to unsaturated tert-butyl esters in the presence of chiral dienes as ligands. The addition of both

商品

Carreira DOLEFIN Ligands

The selective preparation of diarylmethine stereogenic centers is a challenging endeavor in chemical synthesis, especially when there is little differentiation between the two aryl groups

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