[ CAS No. 496-16-2 ] {[proInfo.proName]}

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Quality Control of [ 496-16-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 496-16-2 ]

SDS Specification

Alternatived Products of [ 496-16-2 ]

Product Citations

An efficient behavioral screening platform classifies natural products and other chemical cues according to their chemosensory valence in C. elegans

Fryer, Emily ; Guha, Sujay ; Rogel-Hernandez, Lucero E , et al. bioRxiv,2023.06.02.542933. DOI: 10.1101/2023.06.02.542933 PubMed ID: 37333363

Abstract: Throughout history, humans have relied on plants as a source of medication, flavoring, and food. Plants synthesize large chemical libraries and release many of these compounds into the rhizosphere and atmosphere where they affect animal and microbe behavior. To survive, nematodes must have evolved the sensory capacity to distinguish plant-made small molecules (SMs) that are harmful and must be avoided from those that are beneficial and should be sought. This ability to classify chemical cues as a function of their value is fundamental to olfaction, and represents a capacity shared by many animals, including humans. Here, we present an efficient platform based on multi-well plates, liquid handling instrumentation, low-cost optical scanners, and bespoke software that can efficiently determine the chemotaxis valence of single SMs in the model nematode, Caenorhabditis elegans. Using this integrated hardware-wetware-software platform, we screened 90 plant SMs and identified 37 that attracted or repelled wild-type animals, but had no effect on mutants defective in chemosensory transduction. Genetic dissection indicates that for at least 10 of these SMs, response valence emerges from the integration of opposing signals, arguing that olfactory valence is often determined by integrating chemosensory signals over multiple lines of information. This study establishes that C. elegans is an effective discovery engine for determining chemotaxis valence and for identifying natural products detected by the chemosensory nervous system.

Purchased from AmBeed: 106-22-9 ; 474-58-8 ; 496-16-2

Product Details of [ 496-16-2 ]

CAS No. :	496-16-2	MDL No. :	MFCD00005855
Formula :	C₈H₈O	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	HBEDSQVIWPRPAY-UHFFFAOYSA-N
M.W :	120.15	Pubchem ID :	10329
Synonyms :	2,3-Dihydrobenzofuran	Chemical Name :	2,3-Dihydrobenzo[b]furan

Calculated chemistry of [ 496-16-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	35.79
TPSA :	9.23 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.89
Log Po/w (XLOGP3) :	2.14
Log Po/w (WLOGP) :	1.62
Log Po/w (MLOGP) :	1.75
Log Po/w (SILICOS-IT) :	2.62
Consensus Log Po/w :	2.0

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.45 mg/ml ; 0.00375 mol/l
Class :	Soluble
Log S (Ali) :	-1.97
Solubility :	1.3 mg/ml ; 0.0108 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.64
Solubility :	0.276 mg/ml ; 0.0023 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.49

Safety of [ 496-16-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 496-16-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 496-16-2 ]
Downstream synthetic route of [ 496-16-2 ]

[ 496-16-2 ] Synthesis Path-Upstream 1~4

1
[ 496-16-2 ]
[ 76429-69-1 ]

Reference： [1] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7529 - 7537
[2] Synlett, 2005, # 18, p. 2837 - 2842
[3] Patent: WO2007/27917, 2007, A2, . Location in patent: Page/Page column 26

2
[ 496-16-2 ]
[ 42933-43-7 ]

Reference： [1] ACS Catalysis, 2016, vol. 6, # 12, p. 8162 - 8165
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6430 - 6446
[3] Patent: EP2532665, 2012, A1,
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601

3
[ 496-16-2 ]
[ 42933-43-7 ]
[ 13414-56-7 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567

4
[ 496-16-2 ]
[ 869885-60-9 ]

Reference： [1] Patent: US2008/227744, 2008, A1,

Yield	Reaction Conditions	Operation in experiment
22 - 35%Chromat.	With sodium methylate; carbonic acid dimethyl ester; In methanol; at 85℃; for 5h;Product distribution / selectivity;	Example 5 Mixtures of diols, dimethyl carbonate and the selected base were refluxed in an oil bath under nitrogen atmosphere as reported in Tables 3 and 4. Cooled samples of the reaction mixtures were filtered on silica pads and the recovered clear solutions were analysed by gas chromatography.
100%Chromat.	With potassium tert-butylate; carbonic acid dimethyl ester; at 90℃; for 0.5h;Product distribution / selectivity;	Example 5 Mixtures of diols, dimethyl carbonate and the selected base were refluxed in an oil bath under nitrogen atmosphere as reported in Tables 3 and 4. Cooled samples of the reaction mixtures were filtered on silica pads and the recovered clear solutions were analysed by gas chromatography.
92%Chromat.	With sodium methylate; carbonic acid dimethyl ester; at 90℃; for 2h;Product distribution / selectivity;	Example 5 Mixtures of diols, dimethyl carbonate and the selected base were refluxed in an oil bath under nitrogen atmosphere as reported in Tables 3 and 4. Cooled samples of the reaction mixtures were filtered on silica pads and the recovered clear solutions were analysed by gas chromatography.

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