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Merck
CN

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%

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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
经验公式(希尔记法):
C22H30O
分子量:
310.47
MDL编号:
UNSPSC代码:
12352112
PubChem化学物质编号:

检测方案

95%

形式

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

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

(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.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves

法规信息

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Rhodium-catalyzed 1, 4-additions to enantiopure acceptors: Asymmetric synthesis of functionalized pyrrolizidinones
Zoute L, et al.
Organic Letters, 11(12), 2491-2494 (2009)
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)
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.
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
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

商品

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

相关内容

The Carreira Research Group is focused on expanding and creating access to uncharted landscape in chemical space. In joint efforts with SpiroChem, Carreira develops innovative spirocyclic building blocks, seeking to make them available to the community at large. Molecules constructed from these building blocks take on unique three-dimensional profiles due to the underlying spirocyclic scaffold, enriched by the presence of diverse combinations of exit vectors as sites for functionalization. Importantly, the spirocyclic building blocks possess physicochemical properties useful in the drug discovery process. Thus, drug leads can be tuned through appending these subunits to the periphery of a given scaffold. Moreover, these compact modules represent a useful collection of unprecedented inputs for fragment-based libraries. In all applications, the inherent novelty of the structure affords researchers new opportunities to run wild in their designs and avenues to chemical space – with their imagination as the sole limitations. We are proud to partner in the efforts to make these building blocks widely available.

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