420964
(1S)-(+)-酮基蒎酸
99%
别名:
(1S)-7,7-二甲基-2-氧代二环[2.2.1]庚烷-1-甲酸
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关于此项目
经验公式（希尔记法）:
C10H14O3
化学文摘社编号:
分子量:
182.22
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4180005
产品名称
(1S)-(+)-酮基蒎酸, 99%
InChI
1S/C10H14O3/c1-9(2)6-3-4-10(9,8(12)13)7(11)5-6/h6H,3-5H2,1-2H3,(H,12,13)/t6-,10+/m1/s1
SMILES string
CC1(C)C2CCC1(C(O)=O)C(=O)C2
InChI key
WDODWBQJVMBHCO-LDWIPMOCSA-N
assay
99%
optical activity
[α]23/D +58°, c = 1 in chloroform
mp
237-239 °C (lit.)
functional group
carboxylic acid
ketone
Quality Level
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Application
用于制备新型手性噁唑烷酮辅助剂和酮基蒎酸衍生聚合物，该聚合物可用于胺的去外消旋化。合成纯手性 2,10-莰烷二醇的原料。用于生成手性席夫碱前体，以制备二乙基 (S)-α-氨基-α-烷基膦酸酯。
(1S)-(+)-Ketopinic acid may be used to prepare:
- Chiral phosphine-oxazoline ligands, which can used in asymmetric palladium-catalyzed Heck reaction of aryl or alkenyl triflates with cyclic alkenes.
- A chiral imino-phosphine ligand, which can be used in palladium-catalyzed asymmetric Diels–Alder reactions to prepare six-membered carbocycles.
- A chiral iminopyridine ligand, which can be used in copper-catalyzed Henry (nitro aldol) reaction between nitromethane and o-anisol to form the corresponding β-hydroxynitroalkane.
General description
(1S)-(+)-Ketopinic acid is a chiral ketone.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
Deng, J. et al.
Synthesis, 963-963 (1991)
Yan, T.-H. et al.
Tetrahedron Letters, 32, 4959-4959 (1991)
Chiral P, N-ligands based on ketopinic acid in the asymmetric Heck reaction.
Gilbertson SR and Fu Z.
Organic Letters, 3(2), 161-164 (2001)
Palladium-catalyzed asymmetric Diels-Alder reactions with novel chiral imino-phosphine ligands.
Hiroi K and Watanabe K.
Tetrahedron Asymmetry, 12(22), 3067-3071 (2001)
Calmes, M. et al.
Tetrahedron Asymmetry, 5, 817-817 (1994)
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