[ CAS No. 19833-96-6 ] {[proInfo.proName]}

Name: 19833-96-6|Methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate|98%
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Quality Control of [ 19833-96-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 19833-96-6 ]

Product Details of [ 19833-96-6 ]

CAS No. :	19833-96-6	MDL No. :	MFCD00019295
Formula :	C₁₄H₁₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FGMUSNHTKNGVQD-UHFFFAOYSA-N
M.W :	234.29	Pubchem ID :	89233
Synonyms :

Calculated chemistry of [ 19833-96-6 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	65.27
TPSA :	46.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.61
Log Po/w (XLOGP3) :	2.81
Log Po/w (WLOGP) :	2.13
Log Po/w (MLOGP) :	2.12
Log Po/w (SILICOS-IT) :	2.55
Consensus Log Po/w :	2.44

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.06
Solubility :	0.204 mg/ml ; 0.000871 mol/l
Class :	Soluble
Log S (Ali) :	-3.44
Solubility :	0.0842 mg/ml ; 0.00036 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.11
Solubility :	0.181 mg/ml ; 0.000773 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.55

Safety of [ 19833-96-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 19833-96-6 ]

* 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 [ 19833-96-6 ]
Downstream synthetic route of [ 19833-96-6 ]

[ 19833-96-6 ] Synthesis Path-Upstream 1~4

1
[ 427-49-6 ]
[ 74-88-4 ]
[ 19833-96-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2 h;	To a mixture of racemic cyclopentylmandelic acid R/S(+/-)1 (4.47 g, 20 mmol) and potassium carbonate (7.01 g, 50 mmol) in DMF (50 ml), methyl iodide (8.64 g, 60 mmol) was added at room temperature. The mixture was stirred at room temperature for 2 h, and then poured into water and extracted with hexanes three times. Evaporation of the dried hexanes extract gave a crude product. Flash chromatography of the crude product on silica gel with 1.5:1 hexanes:methylene chloride gave the pure product 2 (3.02 g, 64percent). ¹H NMR(CDCl₃, 300 MHz): 1.32-1.37, 1.43-1.69 [8H, m, (CH₂)₄], 2.90 [1H, p, CHC(OH)], 3.74(1H, s, OH), 3.77 (3H, s, CH₃), 7.25-7.37, 7.63-7.65 (5H, m, Ph) ppm.

Reference： [1] Patent: US2007/123557, 2007, A1, . Location in patent: Page/Page column 9

2
[ 15206-55-0 ]
[ 542-92-7 ]
[ 19833-96-6 ]

Reference： [1] Patent: US6028198, 2000, A,

3
[ 15206-55-0 ]
[ 19833-96-6 ]

Reference： [1] Patent: US6028198, 2000, A,

4
[ 15206-55-0 ]
[ 137-43-9 ]
[ 19833-96-6 ]

Reference： [1] Organic Process Research and Development, 2012, vol. 16, # 11, p. 1754 - 1769

[ 19833-96-6 ] Synthesis Path-Downstream 1~36

1
[ 19833-96-6 ]
[ 60204-53-7 ]
cyclopentyl-hydroxy-phenyl-acetic acid 4a,6a-dimethyl-tetrahydro-1,4-dioxa-6b-aza-cyclopenta[<i>cd</i>]pentalen-2a-ylmethyl ester [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1976,vol. 13,p. 337 - 348

2
[ 19833-96-6 ]
[ 106650-02-6 ]
[ 96784-26-8 ]

Reference： [1]Journal of Pharmaceutical Sciences,1985,vol. 74,p. 208 - 210

3
[ 15433-79-1 ]
[ 19833-96-6 ]
Cyclopentyl-hydroxy-phenyl-acetic acid 5-dimethylaminomethyl-furan-2-ylmethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 4278 - 4287

4
[ 19833-96-6 ]
[ 158786-33-5 ]
Cyclopentyl-hydroxy-phenyl-acetic acid 5-[(isopropyl-methyl-amino)-methyl]-furan-2-ylmethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 4278 - 4287

6
[ 19833-96-6 ]
[ 1619-34-7 ]
[ 26758-53-2 ]

Reference： [1]Journal of Chemical Research,2005,p. 787 - 788

7
[ 19833-96-6 ]
endo-2-(2-cyclopentyl-2-hydroxy-2-phenyl)acetoxy-7-methyl-7-azabicyclo<2.2.1>heptane methobromide [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,1985,vol. 74,p. 208 - 210

8
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[ 19833-96-6 ]

Yield	Reaction Conditions	Operation in experiment
76.9%		(2) Using the same method as described for (1) of example 3, raw materials at equal weight were added successively. The difference was using a reaction temperature of -10-6 C. during dropuise addition of the toluene solution of 82 g of methyl phenylglyoxylate to cyclopentadiene Grignard reagent. 90 g of methyl 2-phenyl-2-cyclopentyl-2-hydroxy-acetate was obtained in 76.9% yield, nD25 1.5203, boiling point 82-5 C./0.03 mmHg. Silicagel GF 254 thin layer plate; developer: 1,2-dichloroethane, ultraviolet 254 nm fluorescence localization, main spot: Rf=0.72, without impurity spot.

Reference： [1]Patent: US6028198,2000,A

9
[ 15206-55-0 ]
[ 542-92-7 ]
[ 19833-96-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic acid;aluminum nickel; In toluene;	(1) Preparation of methyl 2-phenyl-2-cyclopentyl-2 hydroxy acetate: 22 g (0.90 mol, grade 4) of magnesium filings and 250 ml of absolute ether were added into a three-necked flask. 110 g (1.0 mol, grad 3) of ethyl bromide in 250 ml of absolute ether solution were added dropwise to form Grignard reagent. Dry nitrogen gas was bubbled and ether was evaporated. When te inner temperature rose to 60 C., 200 ml of anhydrous toluene was added and ether was distilled continuously until the inner temperature rose to 95 C. 60 g (0.9 mol) of Cyclopentadiene (industrial grade, freshly distilled, boiling point 40-41 C.) in 250 ml of anhydrous toluene solution were added dropwise with stirring. After addition the temperature was reduced to 80 C. and distilling apparatus was used. 20 ml of ether was added and the mixture was distilled to inner temperature rising to 100 C. After cooling the reaction mixture to -5-0 C., toluene solution of 82 g (0.50 mol) of methyl phenylglyoxylate was added dropwise. After addition, the reaction mixture was stirred for 10 min and ice bath was removed, followed by stirring for 50 min at room temperature (21-23 C.) and cooling. 300 ml of 30% acetic acid and 25 ml of concentrate hydrochloric acid were added dropwise with stirring to dissolve all solid. The toluene layer was separated and washed successively with water, sodium bicarbonate solution and water. The toluene solution was transferred into a hydrogenator and 20 g of T-1-type Raney nickel was added. Reaction proceeded at room temperature until hydrogenation slowed down obviously. The material was taken out and fillered off the catalyst. The residue was washed with toluene. The washings and the filtrate were put together and toluene was evaporated, followed by distillation under reduced pressure. The fraction at 82-5 C./0.03 mm Hg was collected to obtain 96 g of the product in 82% yield, nD25 1.5205, IR: VOH 3535 cm-1, Vc=0 1725 cm-1.

Reference： [1]Patent: US6028198,2000,A

10
[ 19833-96-6 ]
[ 104641-60-3 ]
C₁₈H₂₅NO₃ [ No CAS ]

Reference： [1]Patent: WO2004/54971,2004,A1 .Location in patent: Page/Page column 11-12

11
[ 427-49-6 ]
[ 74-88-4 ]
[ 19833-96-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;	To a mixture of racemic cyclopentylmandelic acid R/S(+/-)1 (4.47 g, 20 mmol) and potassium carbonate (7.01 g, 50 mmol) in DMF (50 ml), methyl iodide (8.64 g, 60 mmol) was added at room temperature. The mixture was stirred at room temperature for 2 h, and then poured into water and extracted with hexanes three times. Evaporation of the dried hexanes extract gave a crude product. Flash chromatography of the crude product on silica gel with 1.5:1 hexanes:methylene chloride gave the pure product 2 (3.02 g, 64%). 1H NMR(CDCl3, 300 MHz): 1.32-1.37, 1.43-1.69 [8H, m, (CH2)4], 2.90 [1H, p, CHC(OH)], 3.74(1H, s, OH), 3.77 (3H, s, CH3), 7.25-7.37, 7.63-7.65 (5H, m, Ph) ppm.

Reference： [1]Patent: US2007/123557,2007,A1 .Location in patent: Page/Page column 9

12
[ 13220-33-2 ]
[ 19833-96-6 ]
[ 13118-11-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium; In n-heptane; for 3h;	A solution of 2 (2.20 g, 9.4 mmol) and N-methyl-3-pyrrolidinol (3, 1.30 g, 13 mmol) in 40 ml of n-heptane was heated until 20 ml of heptane had been distilled. About 0.003 g of sodium was added, and the solution was stirred and heated for 2 h as the distillation was continued. More heptane was added at such a rate as to keep the reaction volume constant. Additional sodium was added at the end of an hour. The solution was then cooled and extracted with 3N HCl. The acid extract was made alkaline with concentrated NaOH and extracted three times with ether. Removal of the dried ether solution gave a crude oil. Flash chromatography of the crude product on silica gel with 8:1 EtOAc:EtOH gave pure product 4 (2.053 g, 72percent). Analysis for C18H25NO3. Calcd: C, 71.26; H, 8.31; N, 4.62. Found: C, 71.55; H, 8.44; N, 4.68. 1H NMR(CDCl3, 500 MHz): 1.27-1.35, 1.40-1.47, 1.54-1.60, 1.75-1.90 [8H, m, (CH2)4], 2.12-2.30, 2.52-2.57, 2.64-2.81 (6H, m CH2NCH2CH2), 2.33, 2.36 (3H, 2s, NCH3), 2.93 [(1H, p, CHC(OH)], 3.83 (1H, bs, OH), 5.23 (1H, m, CO2CH), 7.23-7.36, 7.64-7.67 (5H, m, Ph) ppm.

Reference： [1]Patent: US2007/123557,2007,A1 .Location in patent: Page/Page column 9

13
HNA [ No CAS ]
[ 19833-96-6 ]
[ 25333-42-0 ]
[ 440676-21-1 ]

Yield	Reaction Conditions	Operation in experiment
13.1 g (69%)	In toluene; mineral oil;	Preparation of 2-Cyclopentyl-2-hydroxy-2-phenylacetic Acid (3R)-1-azabicyclo[2.2.2]oct-3-yl Ester Prepared using the same method as for Intermediate I-1, but from 13.5 g (0.0576 mol) of <strong>[19833-96-6]2-Cyclopentyl-2-hydroxy-2-phenylacetic acid methyl ester</strong> (commercially available) dissolved in 350 ml of toluene, 8.0 g (0.063 mol) of (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane and 0.91 g (0.023 mol) of HNa (60% dispersion in mineral oil). The yield was 13.1 g (69%) of the title product as an oil mixture of diastereomers, structure confirmed by 1H-NMR. The two diastereomers I-5a and I-5b were separated after several crystallizations.

Reference： [1]Patent: US2004/72863,2004,A1

14
[ 15206-55-0 ]
[ 137-43-9 ]
[ 19833-96-6 ]