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Merck
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文件

364037

Sigma-Aldrich

2-羟基-丁酸酮

technical grade

别名:

(±)-α-羟基-γ-丁内酯

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About This Item

经验公式（希尔记法）:
C4H6O3
CAS号:
19444-84-9
分子量:
102.09
Beilstein:
80587
MDL號碼:
MFCD00134268
分類程式碼代碼:
12352100
PubChem物質ID:
24862411
NACRES:
NA.22

等級

technical grade

形狀

viscous liquid

折射率

n20/D 1.468 (lit.)

bp

133 °C/10 mmHg (lit.)

密度

1.309 g/mL at 25 °C (lit.)

SMILES 字串

OC1CCOC1=O

InChI

1S/C4H6O3/c5-3-1-2-7-4(3)6/h3,5H,1-2H2

InChI 密鑰

FWIBCWKHNZBDLS-UHFFFAOYSA-N

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相关类别

一般說明

α-Hydroxy-γ-butyrolactone is a 5-membered cyclic ester. It was obtained via tin-conversion of biomass-derived 1,3-dihydroxyacetone (DHA) and formaldehyde.

應用

α-Hydroxy-γ-butyrolactone may be employed as starting reagent in the synthesis of series of seco-pseudonucleoside synthons via aminolysis. It may be employed as starting reagent in the synthesis of enantiomerically pure orthogonally protected δ-azaproline, via Mitsunobu reaction.

儲存類別代碼

10 - Combustible liquids

水污染物質分類（WGK）

WGK 3

閃點（°F）

235.4 °F - closed cup

閃點（°C）

113 °C - closed cup

個人防護裝備

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Sho Yamaguchi et al.
Chemical communications (Cambridge, England), 50(35), 4600-4602 (2014-03-29)
The direct conversion of biomass-derived 1,3-dihydroxyacetone (DHA) and formaldehyde to α-hydroxy-γ-butyrolactone (HBL) was achieved through the use of tin(iv) chloride and a small amount of water and the yield reached up to 70%. The reaction mechanism was also investigated by
Efficient synthesis of enantiomerically pure (S)-d-azaproline starting from (R)-a-hydroxy-?-butyrolactone via the Mitsunobu reaction.
Voss E, et al.
Tetrahedron Asymmetry, 20(15), 1809-1812 (2009)
Natalia N Dioubankova et al.
Organic letters, 4(26), 4607-4610 (2002-12-20)
[reaction: see text] Two series of seco-pseudonucleoside synthons were synthesized from (R)-(+)-alpha-hydroxy-gamma-butyrolactone and (R)-(-)-pantolactone by aminolysis, side-chain protection, dimethoxytritylation, and phosphitylation or solid-phase attachment. The phosphoramidites and solid supports were used in automated DNA synthesis to prepare oligonucleotides modified with

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