186511
(S)-(+)-2-吡咯烷甲醇
97%
别名:
(S)-(+)-2-(羟甲基)吡咯烷, L-脯氨醇
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关于此项目
经验公式（希尔记法）:
C5H11NO
化学文摘社编号:
分子量:
101.15
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
245-605-2
Beilstein/REAXYS Number:
79843
MDL number:
Assay:
97%
InChI key
HVVNJUAVDAZWCB-YFKPBYRVSA-N
InChI
1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m0/s1
SMILES string
OC[C@@H]1CCCN1
assay
97%
optical activity
[α]20/D +31°, c = 1 in toluene
refractive index
n20/D 1.4853 (lit.)
bp
74-76 °C/2 mmHg (lit.)
density
1.025 g/mL at 25 °C (lit.)
functional group
hydroxyl
Quality Level
General description
(S)-(+)-2-吡咯烷基甲醇又称为(S)-(+)-脯氨醇，在手性有机物合成中用作手性合成砌块。还可用作不对称合成的手性助剂和不对称催化的手性配体。
Application
(S)-(+)-2-吡咯烷基甲醇可作为起始原料合成(S)-α,α-二芳基-2-吡咯烷基甲醇。在合成中起着赋予终产物手性的重要作用。
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - STOT SE 3
target_organs
Respiratory system
存储类别
10 - Combustible liquids
wgk
WGK 3
flash_point_f
186.8 °F - closed cup
flash_point_c
86 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Chuan Wang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(37), 11531-11535 (2012-07-28)
Sulfenylated oxindoles: The first asymmetric sulfenylation of N-Boc-protected oxindoles has been developed to provide products containing a tetrasubstituted stereogenic center in high to excellent yields (86-98 %) and, in most cases, excellent enantioselectivities (up to 96 % ee; see scheme).
Anna Maria Deobald et al.
Organic & biomolecular chemistry, 10(38), 7681-7684 (2012-08-25)
An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The
Patrick G McGarraugh et al.
Organic letters, 13(24), 6460-6463 (2011-11-17)
Products of a novel iminium-catalyzed oxa-Michael addition undergo a kinetic resolution by a subsequent enamine-catalyzed intermolecular reaction. This is a rare example of kinetic resolution by enamine catalysis and the first organocascade kinetic resolution. This resolution produces enantioenriched 2,6-cis-tetrahydropyrans and
Takashi Mino et al.
The Journal of organic chemistry, 70(5), 1937-1940 (2005-02-26)
Chiral diaminophosphines 4 were prepared from (S)-prolinol-derived aminophosphine oxide 5 by bromination with ring expansion followed by amination with ring contraction and reduction, using trichlorosilane. In the presence of 4 as a ligand, palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate
Tatsuya Urushima et al.
Organic letters, 12(13), 2966-2969 (2010-06-10)
Diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of commercially available polymeric ethyl glyoxylate, affording gamma-ethoxycarbonyl-beta-hydroxy aldehydes, versatile synthetic intermediates, in good yield with excellent enantioselectivity.
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