[ CAS No. 29943-42-8 ] {[proInfo.proName]}

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Quality Control of [ 29943-42-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 29943-42-8 ]

Product Details of [ 29943-42-8 ]

CAS No. :	29943-42-8	MDL No. :	MFCD00006581
Formula :	C₅H₈O₂	Boiling Point :	No data available
Linear Structure Formula :	O(CH₂CH₂)₂CO	InChI Key :	JMJRYTGVHCAYCT-UHFFFAOYSA-N
M.W :	100.12	Pubchem ID :	121599
Synonyms :		Chemical Name :	Dihydro-2H-pyran-4(3H)-one

Calculated chemistry of [ 29943-42-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	25.32
TPSA :	26.3 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.28
Log Po/w (XLOGP3) :	-0.47
Log Po/w (WLOGP) :	0.37
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	1.64
Consensus Log Po/w :	0.5

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.16
Solubility :	68.5 mg/ml ; 0.685 mol/l
Class :	Very soluble
Log S (Ali) :	0.38
Solubility :	243.0 mg/ml ; 2.42 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.82
Solubility :	15.2 mg/ml ; 0.152 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.33

Safety of [ 29943-42-8 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235	UN#:	1224
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 29943-42-8 ]

* 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 [ 29943-42-8 ]
Downstream synthetic route of [ 29943-42-8 ]

[ 29943-42-8 ] Synthesis Path-Upstream 1~3

1
[ 29943-42-8 ]
[ 518990-21-1 ]

Reference： [1] Patent: CN108546266, 2018, A,

2
[ 29943-42-8 ]
[ 1403254-99-8 ]

Reference： [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1556 - 1564
[2] Patent: CN105440023, 2016, A,

3
[ 29943-42-8 ]
[ 24265-23-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide In ethanol; dichloromethaneReflux	Step one: the tetrahydropyran-4-one (10.0 g, 0 . 1mol), paratoluene [...] (18.6 g, 0 . 1mol) and ethanol 120 ml after mixing, heating reflux reaction, after the reaction to evaporate the solvent, directly adding DBU (22.8 g, 0 . 15mol) and dichloromethane 150 ml in, then dropwise NBS (26.7 g, 0 . 15mol) dissolved in 40 ml of methylene chloride solution, after the reaction is complete, by adding 10percent hydrochloric acid to adjust PH= 4-5, separating the organic layer, evaporating the solvent at normal pressure, by adding 20 ml of sulfolane, vacuum distillation to obtain 12.2 g pale yellow liquid: 3,6-dihydro -2H-pyran-4-bromo, GC: 98.4percent, yield 75percent;
62%	With triphenyl phosphite; bromine; triethylamine In dichloromethane	Step 2: 4-Bromo-3,6-dihydro-2H-pyran 4.79 g (30.0 mmol) of bromine were added dropwise to a solution of 8.52 g (27.5 mmol) of triphenyl phosphite in 78 ml of anhydrous methylene chloride at -60° C. After addition of 4.5 ml (32.5 mmol) of triethylamine, a solution of 2.5 g (25.0 mmol) of tetrahydro-4H-pyran-4-one in 2 ml of methylene chloride was added dropwise. The reaction mixture was allowed to warm slowly (over approx. 5 h) to RT and stirring was continued at RT for a further approx. 10 h. All the volatile constituents were then removed on a rotary evaporator and the residue obtained was chromatographed coarsely by filtration with suction over approx. 100 g of silica gel with methylene chloride as the mobile phase. After renewed evaporation of the solvent, the product was isolated by means of bulb tube distillation (pressure: 8 mbar; temperature: to 120° C.). 2.51 g (62percent of th.) of the title compound were obtained. ¹H-NMR (400 MHz, CDCl₃, δ/ppm): 6.07 (m, 1H), 4.13 (m, 2H), 3.83 (m, 2H), 2.55-2.50 (m, 2H). GC/MS (method L, ESIpos): R_t=2.32 min, m/z=162/164 [M]⁺.

Reference： [1] Patent: CN105503927, 2016, A, . Location in patent: Paragraph 0014
[2] Patent: US2013/196964, 2013, A1, . Location in patent: Paragraph 1214; 1215; 1216; 1217
[3] Heterocycles, 2015, vol. 91, # 8, p. 1654 - 1659
[4] Patent: CN104004006, 2016, B,

[ 29943-42-8 ] Synthesis Path-Downstream 1~10

1
[ 29943-42-8 ]
[ 6296-99-7 ]
2-[(3,6-dihydro-2<i>H</i>-pyran-4-ylamino)-methylene]-malonic acid diethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3441 - 3444

2
[ 29943-42-8 ]
[ 33024-60-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium formate;palladium 10% on activated carbon; In methanol; water; at 20℃;	Reference Example 17 Tetrahydro-2H-pyran-4-ylamine hydrochloride To a solution of tetrahydro-4H-pyran-4-one (4.30 g, 43.0 mmol) in methanol (112 ml) was added an aqueous solution (12.5 ml) of ammonium formate (25 g, 400 mmol). Insolubles were completely dissolved and then 10percent palladium carbon (5.1 g) was added thereto, which was stirred at room temperature overnight. After the insolubles were filtrated off to obtain a filtrate, which was concentrated, and to the residue was added ethanol (100 ml) and concentrated hydrochloric acid (7.5 ml). The solvent was distilled off under reduced pressure to give an objective product, which was collected by filtration and washed with ether. 1H-NMR (DMSO-d6) delta: 1.54-1.74 (2H, m), 1.82-1.98 (2H, m), 3.27-3.38 (3H, m), 3.87-3.94 (2H, m), 9.05 (3H, bs). IR (KBr) cm-1; 2966, 1377, 1163, 1088, 1015, 986, 862.

Reference： [1]Patent: EP1535922,2005,A1 .Location in patent: Page/Page column 40

3
[ 29943-42-8 ]
[ 1403257-80-6 ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 1556 - 1564
[2]Patent: CN105440023,2016,A
[3]Patent: WO2018/81530,2018,A1

4
[ 29943-42-8 ]
[ 32161-30-1 ]
[ 59795-89-0 ]
[ 22483-09-6 ]
C₂₉H₄₁N₃O₇ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 8048 - 8052

5
[ 29943-42-8 ]
[ 88333-03-3 ]
[ 32161-30-1 ]
[ 22483-09-6 ]
C₂₈H₃₉N₃O₇ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 8048 - 8052

6
[ 29943-42-8 ]
[ 32161-30-1 ]
[ 59795-89-0 ]
4-((5S)-8,9-dimethoxy-4-oxo-1,2,3,4,5,6-hexahydro-1,5-epiminobenzo[d]azocin-11-yl)-N-phenethyltetrahydro-2H-pyran-4-carboxamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 8048 - 8052

7
[ 29943-42-8 ]
[ 88333-03-3 ]
[ 32161-30-1 ]
N-benzyl-4-((5S)-8,9-dimethoxy-4-oxo-1,2,3,4,5,6-hexahydro-1,5-epiminobenzo[d]azocin-11-yl)tetrahydro-2H-pyran-4-carboxamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 8048 - 8052

8
[ 29943-42-8 ]
[ 5417-17-4 ]
3,5-bis(2-chloro-3,4-dimethoxybenzylidene)tetrahydropyran-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydroxide; In ethanol; at 5 - 27℃;	General procedure: The a,b-unsaturated carbonyl-based cyclohexanone compoundswere synthesized using direct coupling method as reportedpreviously28,37 (Table 2). The ketones were reacted with suitablearomatic aldehyde at molar ratio 1:2 using base-catalyzed claisen-schmidt condensation to synthesize 21 new compounds (3a?3u). Characterization data of only three compounds (3c, 3f, 3o)was reported previously.37 The flow diagram for the synthesis ofa,b-unsaturated carbonyl-based compounds is shown in Scheme 1.The ketone (10 mmol, 1 equiv) and aromatic aldehyde (20 mmol,2 equiv) were mixed in round bottom flask using 25 mL ethanolat 5 C. 40percent sodium hydroxide solution (in ethanol) was added tothis solution. The mixture was stirred for 1?24 h at 27 C. The precipitateappearance and color variation indicated product formation.The reaction was monitored using TLC while acidified icewas added to stop it when completed. Recrystallization and/or columnchromatography were used to isolate the compounds. 4.3.20 3,5-Bis-(2-chloro-3,4-dimethoxy-benzylidene)-tetrahydro-pyran-4-one (3t) Yield: 70percent; Mp: 106-108 °C; 1H NMR (500 MHz, CDCl3) delta: 7.79 (s, 2H), 6.89 (d, J = 8.5 Hz, 2H), 6.53 (d, J = 8.5 Hz, 2H), 3.70 (s, 12H), 2.69 (s, 4H); 13C NMR (500 MHz, CDCl3) delta: 187.4, 152.3, 143.6, 136.2, 131.0, 126.5, 124.7, 114.9, 100.2, 68.2, 56.9, 55.6; HRMS (ESI) m/z: 466.32 [M+H]+, Microanalysis calculated for C23H22Cl2O6 (465.32): C, 59.37; H, 4.77. Found: C, 59.55; H, 4.86.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2352 - 2359
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 3549 - 3561

9
[ 29943-42-8 ]
[ 186534-02-1 ]
3,5-bis-(3,5,6-trimethylpyrazin-2-ylmethylene)tetrahydropyran-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium hydroxide; In ethanol; at 5 - 27℃;	General procedure: New a, b-unsaturated carbonyl-based compounds (5a-g and 6au)were synthesized using direct coupling technique [40] (Scheme 1). The reaction was carried out using base-catalyzed Claisen-Schmidt condensation reaction, by reacting different types of ketoneswith appropriate aromatic aldehyde at molar ratio 2:1 tosynthesize new compounds (5a-g) and at molar ratio 1:1 for (6a-u).For synthesis of 6a-u first 5a-g intermediates were synthesized andin second step appropriate aldehydes were reacted with intermediates.The detailed method of synthesis has already beenreported by us previously [38,40]. Scheme 1 shows the highlights ofsynthesis of compound 3, 4 and a, b-unsaturated carbonyl-basedcompounds along with oxime derivatives. 15 mL ethanol wastaken in a round bottom flask and aromatic aldehyde (20 mmol, 2equivalent) and specific ketone (10 mmol,1 equivalent) were addedand dissolved using a stirrer for 2-3 min at 5 C. Into the abovesolution, 40% NaOH solution in ethanol was added drop wise andthe mixture was stirred for 1-24 h at 27 C. The color change andprecipitate formation in the reaction mixture showed productformation. TLC was used to monitor the reaction and acidified icewas added to quench the reaction once completed. The isolation ofcompounds was done by recrystallization and/or by using columnchromatography.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 135,p. 34 - 48

10
[ 29943-42-8 ]
[ 1187449-01-9 ]
4-bromo-5-chloro-N-(oxan-4-yl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; for 120h;	Preparation 1354-Bromo-5-chloro-N-(oxan-4-yl)pyridin-2-amine (1750) (1751) A stirred mixture of <strong>[1187449-01-9]2-amino-4-bromo-5-chloropyridine</strong> (500 mg, 2.34 mmol) and tetrahydro-4H- pyran-4-one (654 pL, 7.01 mmol) in 1 ,2-dichloroethane (6 mL) was treated with sodium triacetoxyborohydride (1.277 g, 5.84 mmol). After 5 days the mixture was treated with NaOH (1 M, 5 ml). After 30 minutes, the mixture was diluted with water and extracted with CH2CI2 (x3). The combined organic layers were washed with brine, dried over MgS04, filtered and concentrated under vacuum. The residue was purified by biotage (0-50 percent EtOAc) to yield 4- bromo-5-chloro-N-(oxan-4-yl)pyridin-2-amine (530 mg, 78 percent) as a yellow solid. MS: [M+H]+ = 291/293/295.

Reference： [1]Patent: WO2017/68412,2017,A1 .Location in patent: Page/Page column 237

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Technical Information

? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 29943-42-8 ] {[proInfo.proName]}

Quality Control of [ 29943-42-8 ]

Related Doc. of [ 29943-42-8 ]

Product Details of [ 29943-42-8 ]

Calculated chemistry of [ 29943-42-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 29943-42-8 ]

Application In Synthesis of [ 29943-42-8 ]

[ 29943-42-8 ] Synthesis Path-Upstream 1~3

[ 29943-42-8 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 29943-42-8 ]

Ketones

Related Parent Nucleus of [ 29943-42-8 ]

Aliphatic Heterocycles

Tetrahydropyrans

Precautionary Statements-General

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[ 29943-42-8 ]

Related Parent Nucleus of
[ 29943-42-8 ]