[ CAS No. 946-39-4 ] {[proInfo.proName]}

Name: 946-39-4|Rel-ethyl (1R,2R)-2-phenylcyclopropane-1-carboxylate|95%
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SKU: A422143
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2D 3D

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Quality Control of [ 946-39-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 946-39-4 ]

Product Details of [ 946-39-4 ]

CAS No. :	946-39-4	MDL No. :	MFCD00019221
Formula :	C₁₂H₁₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SRGUIJLJERBBCM-WDEREUQCSA-N
M.W :	190.24	Pubchem ID :	252496
Synonyms :

Calculated chemistry of [ 946-39-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.61
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.4
Log Po/w (XLOGP3) :	2.33
Log Po/w (WLOGP) :	2.35
Log Po/w (MLOGP) :	2.47
Log Po/w (SILICOS-IT) :	2.69
Consensus Log Po/w :	2.45

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.54
Solubility :	0.548 mg/ml ; 0.00288 mol/l
Class :	Soluble
Log S (Ali) :	-2.52
Solubility :	0.573 mg/ml ; 0.00301 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.25
Solubility :	0.107 mg/ml ; 0.000564 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.27

Safety of [ 946-39-4 ]

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

Application In Synthesis of [ 946-39-4 ]

* 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 [ 946-39-4 ]
Downstream synthetic route of [ 946-39-4 ]

[ 946-39-4 ] Synthesis Path-Upstream 1~1

1
[ 946-39-4 ]
[ 185256-47-7 ]

Reference： [1] Tetrahedron Asymmetry, 1996, vol. 7, # 12, p. 3505 - 3512
[2] Tetrahedron Asymmetry, 1996, vol. 7, # 12, p. 3505 - 3512
[3] Tetrahedron Asymmetry, 1996, vol. 7, # 12, p. 3505 - 3512
[4] Tetrahedron Asymmetry, 1996, vol. 7, # 12, p. 3505 - 3512
[5] Tetrahedron Asymmetry, 1996, vol. 7, # 12, p. 3505 - 3512
[6] Tetrahedron Asymmetry, 1996, vol. 7, # 12, p. 3505 - 3512

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Yield	Reaction Conditions	Operation in experiment
96%	With diisobutylaluminium hydride In diethyl ether; toluene at -78℃; for 0.5h; Inert atmosphere;
	With lithium aluminium tetrahydride In diethyl ether Heating;
1.04 g	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1.5h;

	With lithium aluminium tetrahydride In diethyl ether for 6h; Inert atmosphere; Reflux;
	With lithium aluminium tetrahydride In diethyl ether for 6h; Inert atmosphere; Reflux;
	With lithium aluminium tetrahydride In diethyl ether for 6h; Reflux; Inert atmosphere;
	With lithium aluminium tetrahydride In diethyl ether at 25 - 35℃;	Synthesis of 2-p-phenyl-substituted 1-hydroxymethylcyclopropanes. General procedure: A 500-mL three-necked fl ask equippedwith a power-driven stirrer, a dropping funnel, and arefl ux condenser was charged with 9.1 g (0.25 mol) ofLiAlH4 in 200 mL of absolute diethyl ether, and 85 g(0.25 mol) of ethyl 2-phenylcyclopropanecarboxylatewas added over a period of 2.0-2.5 h. The temperatureof the reaction medium was maintained in the range25-35°. After the whole amount of the ester wasadded, the mixture was stirred for an additional 30 min.After that, distilled water and then 5% HCl were addeddropwise. The ether layer was separated, and the aqueouslayer was extracted with ether (2 × 20 mL). The etherextracts were combined with the ether layer and driedover calcined Na2SO4. After distillation of the diethylether, the products were isolated by vacuum distillation.Compounds 5 and 6 were prepared similarly.The IR spectra of 4-6 contain absorption bands inthe ranges 3095-3100 (ν- ring); 2980, 2940, 2880(ν- aliph); 2900-3100 cm-1 ().2-Phenyl-1-hydroxymethylcyclopropane (4). Yield92%, bp 125-130° (9 mm Hg), nD20 1.5110, d420 1.335,RD = 43.235. 1 NMR spectrum, δ, ppm: 6.92 m(5arom), 1.93 m (1, Hcyclopropane), 2.61 m (1,Hcyclopropane), 1.63 m (1, 2cyclopropane), 1.65 m (1,2cyclopropane), 3.86 d (2, 2), 3.64 s (1, ).Found, %: 81.25, 8.05. 10H12O. Calculated, %: 81.08, 8.10.
	With lithium aluminium tetrahydride In diethyl ether for 6h; Inert atmosphere; Reflux;	General procedure: 3) To a stirred solution of LAH (1.5 equiv.) in 7 mL diethyl ether was added dropwise a solution of cyclopropane ester (0.90 mmol,1equiv.) in 3 mL diethyl ether under N2 atmosphere. After addition was completed the reaction mixture was refluxed foranother 6 h. The reaction mixture was then cooled to rt, and the excess LAH was destroyed by water. 15 mL of 10% H2SO4 and 8 mL of ether was added and the aqueous layer was extracted several times with diethyl ether. The combined organic layer was washed with water and 5% NaHCO3, dried over MgSO4 and concentrated in a rotary evaporator (90 - 95% yield). Without any further purification, the crude material (a colorless oil) was used for next step.
	With lithium aluminium tetrahydride In diethyl ether for 6h; Reflux; Inert atmosphere;
	With lithium aluminium tetrahydride In diethyl ether at 20℃; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
1: 67% 2: 27%	With copper(II) bis(2,4-pentanedionate); phenylhydrazine In dichloromethane at 40℃; optical yield given as %de;
1: 62% 2: 32%	With NaAuCl₄; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 26h; optical yield given as %de; chemoselective reaction;
58%	With chiral 2,2'-bipyridyl ligand; copper(II) bis(trifluoromethanesulfonate); phenylhydrazine In dichloromethane at 20℃; for 12h;

48%	With complex of WIVS-FM*-T₂₆₈A/C₄₀₀G with Ir(Me)-deuteroporphyrin IX In aq. phosphate buffer; N,N-dimethyl-formamide Enzymatic reaction; diastereoselective reaction;
1: 44% 2: 21%	With copper chloride (I) In chloroform at 60℃; Inert atmosphere;
32%	With Rh₂(OAc)4 In dichloromethane at 20℃; for 24h; optical yield given as %de;
1: 20 % de 2: 32%	With rhodium(II) acetate dimer In dichloromethane at 20℃; for 12h; Inert atmosphere;
1: ~ 33.333 % de 2: 15%	With copper(II) bis(2,4-pentanedionate); phenylhydrazine In dichloromethane for 5h; diastereoselective reaction;
	at 60℃; other catalysts: Rh(II)pivalate, CuCl;
	at 60℃; Yield given. Yields of byproduct given;
	at 22℃; Yield given. Title compound not separated from byproducts;
	With {RuCl₂(C₁₈H₁₅Sb)3} at 60℃; for 4h; Yield given. Yields of byproduct given;
	Ambient temperature; other catalysts: Rh₂(OOCC₃F₇)4, Rh₂(NHCOCH₃)4;
	at -12.1℃; ΔH(excit.), ΔS(excit.), other catalysts;
	With tris(triphenylphosphine)ruthenium(II) chloride at 60℃; for 4h; effect of catalyst, e.g. OsCl₂(PPh₃)3 temperature and further olefines on product/yield distribution;
	With tris(triphenylphosphine)ruthenium(II) chloride at 60℃; for 4h; Yield given. Yields of byproduct given;
	In 1,2-dichloro-ethane for 5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	at 60℃; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
	In dichloromethane at 40℃; for 12h; Yield given. Yields of byproduct given;
	In dichloromethane at 40℃; for 24h; Yield given. Yields of byproduct given;
	In dichloromethane; 1,2-dichloro-ethane at -20℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	In neat (no solvent) at 100℃; for 4h; Yield given;
	In dichloromethane
	In dichloromethane for 22h; Heating;
	In dichloromethane at 25℃; for 0.67h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	In dichloromethane at 50℃; for 0.67h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	In dichloromethane at 20℃; for 16h;
	In toluene at 110℃; for 0.333333h; microwave irradiation; Title compound not separated from byproducts;
	Ambient temperature; Yield given. Yields of byproduct given;
	Ambient temperature; Yield given. Yields of byproduct given;
	for 1h; Ambient temperature; Title compound not separated from byproducts;
	at 100℃; for 4h; Yield given. Yields of byproduct given;
	In dichloromethane at 20℃;
	In dichloromethane for 8h;
	at 40℃; for 4h;
	at 40℃; for 4h;
	In benzene for 2.66667h; Heating; Yield given. Title compound not separated from byproducts;
	In dichloromethane at 20℃; for 30h; Title compound not separated from byproducts;
	In chloroform at 20℃; for 4h;
	With (S)-2,2'-bis(benzylideneamino)-1,1'-binaphthyl Cu-complex at 40℃;
	With 2,2'-isopropylidenebis<(4S)-4-tert-butyl-4,5-dihydrooxazole>; copper trifluoromethanesulfonate In dichloromethane
	With C₁₇H₂₀N₂O₂; copper(II) bis(trifluoromethanesulfonate) at 20℃; for 20h;
	With copper atom; rhodium
	With chiral 3,7-diazabicyclo[3.3.1]nonane-based reagent; copper trifluoromethanesulfonate In hexane at 20℃; for 24h;
	With PFIEP (K⁽¹⁺⁾, Cu⁽²⁺⁾) In dichloromethane Ambient temperature; Yield given. Yields of byproduct given;
	With rhodium(II) acetate dimer In dichloromethane for 12h;
	With RuCl₂
76.9 % Chromat.	With [Me₂NN]Cu(ethylene) In dichloromethane; toluene for 2h;
	With phenylhydrazine In dichloromethane for 15h; Ambient temperature; Yield given; Yields of byproduct given;
	With tetra-4-tert-butylphthalocyanine complex of cobalt (PcCo) at 24℃; Yield given. Title compound not separated from byproducts;
	In 1,2-dichloro-ethane for 20h; Heating; in the presence of Ph₂S as well;
	In dichloromethane at 40℃; for 12h; other substrate, other temperatures, other time, other amount of catalyst, stereoselectivity;
	In toluene at 20℃; for 3h;
	In neat (no solvent) at 100℃; for 4h; effect of various catalysts and temp.;
	In dichloromethane at 25℃; for 0.67h; various catalyst and reaction conditions; also with other alkenes;
	In dichloromethane at 25℃; for 2h;
	Ambient temperature; further olefins; other rhodium(II) carboxylates; 60 ,40 deg C;
	at 50℃; for 2h;
	In dichloromethane at 20℃; for 16h;
	In 1,2-dichloro-ethane at 60℃; for 48h;
	In dichloromethane for 1h;
	With <OsCl2(p-cymene)>2 at 20 - 100℃; for 4h; cis-trans ratio as a function of temp.;
	With 5-(2-pyridyl)<2>(1,4)benzeno<2>(5,8)quinolinophane; phenylhydrazine In dichloromethane for 15h; Ambient temperature; var. of time, temp.; asymmetric induction;
1: 27 % Spectr. 2: 73 % Spectr.	With 6,6'-bis-(3,4-dimethyl-2-oxo-3-pyrrolin-5-methylidene)-methyl-2,2'-bipyridyl-copper(II) In 1,2-dichloro-ethane at 60℃; for 2h; further reagents;
1: 22 % Chromat. 2: 78 % Chromat.	With 1-methyl-1H-imidazole; 5,10,15,20-tetraphenyl-21H,23H-porphyrin cobalt(II) In toluene at 80℃; for 1h;
	With PFIEP (K⁽¹⁺⁾, Cu⁽²⁺⁾) In dichloromethane Ambient temperature; further olefins, further reagents;
	With dirhodium(II) tetraoctanoate In toluene at 0℃;
	With di-μ-chlorobis-[(η⁶-p-cymene)chlororuthenium(II)]; [(6,6,8-Me₃-5,6,7,8-H₄-5,7-methanoquinolin-2-yl)pyridine]2 In dichloromethane at 20℃; for 2h;
	With (5,10,15,20-tetra-p-tolylporpyrinato)iron(II) for 1h; var. iron porphyrin complexes and solvents, other olefins;
	With tetra-4-tert-butylphthalocyanine complex of cobalt (PcCo) at 24℃; other reagent (transition metal phthalocyanine complexes), other conc. of the reagent, other temp.,;
	In various solvent(s) at 27℃; for 6h;
1: 67 %Spectr. 2: 31 %Spectr.	With [Cu(tris(2-pyridyl)amine)(THF)]2[tetrakis(3,5-bis(trifluoromethyl)phenyl)borate]2 In dichloromethane for 12h;
	With C₁₄H₁₈BiF₆O₈Rh In dichloromethane at 40℃; Inert atmosphere; optical yield given as %de;
	In o-dimethylbenzene at 135 - 140℃; for 6h;
	With gold In toluene at 80℃; for 24h; Inert atmosphere; optical yield given as %de;
	With C₂₅H₁₉Cl₄Cu₂N₃O₈S*H₂O In 1,2-dichloro-ethane Heating; optical yield given as %de; diastereoselective reaction;
	With CuOTf*0.5C₆H₆; C₃₁H₃₄N₂O₈ In dichloromethane at 0℃; for 20h; optical yield given as %de; stereoselective reaction;
	With [Cu₃(1,3,5-benzenetricarboxylate)₂] In dichloromethane at 20℃; for 3h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;
	With [Cu(1,3,5-tris(thiocyanatomethyl)mesitylene)]2[B(C₆H₃(CF₃)2)4]2 In dichloromethane for 7h; optical yield given as %de;
	With Co(N-Me-NCTPP)py In toluene at 80℃; for 18h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;
	With C₃₇H₃₈O₆ In dichloromethane at 25℃; for 20h; Inert atmosphere; optical yield given as %de;
	With C₂₀H₁₉ClN₃ORh; trifluoromethane sulfonic acid silver salt In dichloromethane at 0℃; for 3h; Inert atmosphere; optical yield given as %de;
	With copper(II) bis(trifluoromethanesulfonate) In hexafluoropropan-2-ol at 0 - 20℃; for 4h; optical yield given as %de; diastereoselective reaction;	4.1. Cyclopropanation reaction: general procedure General procedure: To a solution of olefin (1.0 mmol) and Cu(OTf)2 (0.01 mmol) in HFIP (1.5 ml) was added ethyldiazoacetate (EDA, 1.5 mmol) at 0 °C. After stirring at room temperature until completion of reaction (monitored by GC analysis), the reaction mixture was quenched with a saturated aqueous solution of NH4Cl (2 ml), and extracted with CH2Cl2 (2× 5 ml). The organic layers were washed with brine (10 ml), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel.
	In α,α,α-trifluorotoluene at 102℃; Inert atmosphere; optical yield given as %de; diastereoselective reaction;
	With C₂₄H₂₇ClN₃ORh; trifluoromethane sulfonic acid silver salt In dichloromethane at 20℃; for 24h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;
	With C₁₉H₁₇ClN₃ORh; trifluoromethane sulfonic acid silver salt In dichloromethane at 0℃; for 24h; Inert atmosphere; diastereoselective reaction;
	With tetrakis(acetonitrile)copper(I) hexafluorophosphate; 2-(4-hydroxyphenyl)-1,1-bis[(R)-4,5-dihydro-4-phenyloxazoline-2-yl]-ethane In dichloromethane at 25℃; for 48h; optical yield given as %ee; diastereoselective reaction;
	With 2CF₃O₃S^(1-)*C₄₃H₄₉Cu₂Fe₂N₆O₂⁽²⁺⁾ In dichloromethane at 25℃; for 6.5h; Inert atmosphere; optical yield given as %de;
	With C₈H₆Cl₂CuN₃OS*2H₂O In 1,2-dichloro-ethane at 70℃; for 0.2h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;
48 % de	With Co(3,5-Di<SUP>t</SUP>Bu-Ibu-Phyrin) In N,N-dimethyl-formamide for 4h; Heating; Inert atmosphere; Schlenk technique; Overall yield = 56 %;
88.889 % de	With [Ru(TTP)(BIMe)₂] In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Overall yield = 96 %;
70 % de	With C₃₅H₃₀CuN₄⁽¹⁺⁾*ClO₄^(1-) at 60℃; for 23h;
24 % de	With C₁₈H₂₄Br₃N₇Cu⁽¹⁺⁾F₆P^(1-) In dichloromethane at 20℃; for 3h; Inert atmosphere; diastereoselective reaction;
32 % de	With C₄₀H₂₄CoN₈16C₂F₆NO₄S₂^(1-)Fe₈Zn₆⁽¹⁶⁺⁾ In [⁽²⁾H₆]acetone; water monomer at 50℃; for 24h; Schlenk technique; Inert atmosphere; Overall yield = 76 %; Overall yield = 145 mg;
22 % de	With immobilization of bis(oxazoline)copper complexe on mesoporous crystalline material In decane; dichloromethane at 20℃; for 0.5h; Overall yield = 11 %;	Homogeneous cyclopropanation General procedure: At room temperature, ethyl diazoacetate (2.5 mmol, 285 mg)dissolved in dichloromethane (0.5 mL) was added over the course of2 h with a syringe pump to a solution containing the copper catalyst(0.025 mmol), n-decane (100 mg) and styrene (2 mL for reactions inexcess of alkene or 2.5 mmol, 260 mg, in 2 mL dichloromethane forstoichiometric reactions). After the addition, the reaction was leftto stir for 30 min and then analyzed by CG [5-9].
39.394 % de	With tetrakis-2,3-{9-hexadecanoyl-9H-dibenzo[b,f]pyrazino[2,3-d]azepine}porphyrazinatocopper(II) In dichloromethane at 40℃; for 4h; Overall yield = 96 %Chromat.;	General procedure for catalytic cyclopropanation General procedure: A solution of ethyl diazoacetate (EDA)(5.0 mmol in 10 mL of CH2Cl2) was added slowly under stirring to a refluxing CH2Cl2 solution(0.2 M) consisting of alkene (12.5 mmol) and 11 or 12 (0.005 mmol). The reaction was halted when no trace of EDA [ν N=N 2110 cm-1] was detected in the IR spectrum of the mixture. Yield sand diastereomeric ratio were obtained by GC-MS and 1H NMR using examethylbenzene asinternal standard.
75 % de	With copper(I) coordinated tetra-(4-iminophenyl)methane linked mesoporous polymer organic frameworks In dichloromethane at 20℃; for 26h; diastereoselective reaction;

[ CAS No. 946-39-4 ] {[proInfo.proName]}

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