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Merck
CN

669490

(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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关于此项目

经验公式(希尔记法):
C22H30O
化学文摘社编号:
分子量:
310.47
UNSPSC Code:
12352112
PubChem Substance ID:
MDL number:
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assay

95%

form

liquid

optical activity

[α]20/D +98±5°, c = 0.7 in chloroform

reaction suitability

reaction type: click chemistry

refractive index

n20/D 1.5205

functional group

ether, phenyl

SMILES string

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

Application

(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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.


存储类别

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

法规信息

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历史批次信息供参考:

分析证书(COA)

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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

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Enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylheteroarenes
Pattison G, et al.
Journal of the American Chemical Society, 132(41), 14373-14375 (2010)
Rhodium-catalyzed 1, 4-additions to enantiopure acceptors: Asymmetric synthesis of functionalized pyrrolizidinones
Zoute L, et al.
Organic Letters, 11(12), 2491-2494 (2009)
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



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货号GTIN
669490-100MG04061833499658