118559
1,5-Hexadien-3-ol
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About This Item
Linear Formula:
H2C=CHCH2CH(OH)CH=CH2
CAS Number:
Molecular Weight:
98.14
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
213-102-7
MDL number:
InChI key
SZYLTIUVWARXOO-UHFFFAOYSA-N
InChI
1S/C6H10O/c1-3-5-6(7)4-2/h3-4,6-7H,1-2,5H2
SMILES string
OC(CC=C)C=C
refractive index
n20/D 1.448 (lit.)
density
0.878 g/mL at 25 °C (lit.)
functional group
allyl, hydroxyl
General description
1,5-Hexadien-3-ol is the starting reagent for the enantioselective synthesis of (+)-rogioloxepane A. It undergoes Sharpless kinetic resolution and ring-closing metathesis to yield nine membered oxocene.
Application
1,5-Hexadien-3-ol was used in the synthesis of (+)-obtusenyne.
signalword
Warning
hcodes
Hazard Classifications
Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
84.2 °F - closed cup
flash_point_c
29 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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Michael T Crimmins et al.
Journal of the American Chemical Society, 125(25), 7592-7595 (2003-06-19)
A total synthesis of the laurencia metabolite (+)-obtusenyne has been completed. The key steps include a Sharpless kinetic resolution and an asymmetric glycolate alkylation to establish the stereogenic centers adjacent to the ether linkage and a ring-closing metathesis reaction to
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