Merck
CN

12108

Sigma-Aldrich

(±)-顺式-双环[3.2.0]庚-2-烯-6-酮

≥98.0%

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Empirical Formula (Hill Notation):
C7H8O
CAS号:
分子量:
108.14
MDL编号:
PubChem化学物质编号:
NACRES:
NA.22

质量水平

检测方案

≥98.0% (GC)
≥98.0%

折射率

n20/D 1.4820 (lit.)
n20/D 1.483

bp

158-160 °C (lit.)

密度

1.025 g/mL at 25 °C (lit.)

SMILES string

O=C1C[C@@H]2C=CC[C@H]12

InChI

1S/C7H8O/c8-7-4-5-2-1-3-6(5)7/h1-2,5-6H,3-4H2/t5-,6-/m0/s1

InChI key

LNLLHUHPGPKRBM-WDSKDSINSA-N

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一般描述

(±)-cis-bicyclo(3.2.0)hept-2-en-6-one undergoes preparative scale Baeyer–Villiger biooxidation at high concentration using recombinant Escherichia coli biocatalyst and adsorbent resin (in situ substrate feeding and product removal).

应用

(±)-(1S,5R)-cis-bicyclo(3.2.0)hept-2-en-6-one may be used:
  • to study enantioselective Baeyer–Villiger oxidation of (±)-cis-bicyclo(3.2.0)hept-2-en-6-one with H2O2 mediated by Co(Salen) catalyst in water with surfactants
  • to investigate the extremophile enzymes (monooxygenase and hydrolases) in microorganisms isolated from deep-water petroleum reservoir and at high temperatures using fluorogenic assays and multibioreactions
  • in the preparation of series of chalcone derivatives via reacton with arylaldehydes

象形图

CorrosionExclamation mark

警示用语:

Danger

危险分类

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

储存分类代码

12 - Non Combustible Liquids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

法规信息

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Asymmetric Baeyer-Villiger oxidation with Co (Salen) and H2O2 in water: striking supramolecular micelles effect on catalysis.
Bianchini G, et al.
Green Chemistry, 11(10), 1517-1520 (2009)
Georgiana F da Cruz et al.
Applied microbiology and biotechnology, 87(1), 319-329 (2010-03-06)
Microbial oxidation potentials of extremophiles recovered from Pampo Sul oil field, Campos Basin, Brazil, in pure culture or in consortia, were investigated using high-throughput screening (HTS) and multibioreactions. Camphor (1), cis-jasmone (2), 2-methyl-cyclohexanone (3), 1,2-epoxyoctane (4), phenylethyl acetate (5), phenylethyl
Synthesis and Characterization of New Chalcone Derivatives from cis-Bicyclo [3.2. 0] hept-2-en-6-one
Ceylan M and Findik E.
Synthetic Communications, 39(6), 1049-1054 (2009)
Kathleen Balke et al.
Chembiochem : a European journal of chemical biology, 18(16), 1627-1638 (2017-05-16)
Baeyer-Villiger monooxygenase (BVMO)-mediated regiodivergent conversions of asymmetric ketones can lead to the formation of "normal" or "abnormal" lactones. In a previous study, we were able to change the regioselectivity of a BVMO by mutation of the active-site residues to smaller
Iris Hilker et al.
Nature protocols, 3(3), 546-554 (2008-03-08)
An efficient biocatalytic process based on the use of adsorbent resin (in situ substrate feeding and product removal) makes experiments at high substrate concentration possible by overcoming limitations due to substrate and product inhibition. This process was successfully applied to

商品

Baeyer-Villiger氧化反应

Baeyer-Villiger氧化是与羰基相邻的碳-碳键的氧化裂解,其可将酮转化为酯、环酮转化为内酯。

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

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