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118559

Sigma-Aldrich

1,5-Hexadien-3-ol

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About This Item

Linear Formula:
H2C=CHCH2CH(OH)CH=CH2
CAS Number:
924-41-4
Molecular Weight:
98.14
EC Number:
213-102-7
MDL number:
MFCD00008662
UNSPSC Code:
12352100
PubChem Substance ID:
24847376
NACRES:
NA.22

refractive index

n20/D 1.448 (lit.)

density

0.878 g/mL at 25 °C (lit.)

functional group

allyl
hydroxyl

SMILES string

OC(CC=C)C=C

InChI

1S/C6H10O/c1-3-5-6(7)4-2/h3-4,6-7H,1-2,5H2

InChI key

SZYLTIUVWARXOO-UHFFFAOYSA-N

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.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCH9405
MKCH9287
MKCH9286
MKCC9991
MKCC9675

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Induction of rejection of successful allografts of rat islets by donor peritoneal exudate cells.
P E Lacy et al.
Transplantation, 28(5), 415-420 (1979-11-01)
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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Grapes are one of the most important fruits because of their economic and nutritional benefits, and grapevines are widely cultivated in arid and semi-arid areas. Therefore, it is critical to study the mechanism by which grapevines respond to water stress.

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