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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[1]. It undergoes Sharpless kinetic resolution and ring-closing metathesis to yield nine membered oxocene[2].

Application

1,5-Hexadien-3-ol was used in the synthesis of (+)-obtusenyne[2].

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

84.2 °F - closed cup

Flash Point(C)

29 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCH9405
MKCH9287
MKCH9286
MKCC9991
MKCC9675

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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
Yan-Lun Ju et al.
Plant physiology and biochemistry : PPB, 130, 501-510 (2018-08-11)
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.
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)

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