[ CAS No. 2605-67-6 ] {[proInfo.proName]}

Name: 2605-67-6|Methyl 2-(triphenylphosphoranylidene)acetate|98%
Brand: Ambeed
SKU: A197326
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Quality Control of [ 2605-67-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2605-67-6 ]

SDS Specification

Alternatived Products of [ 2605-67-6 ]

Product Details of [ 2605-67-6 ]

CAS No. :	2605-67-6	MDL No. :	MFCD00008455
Formula :	C₂₁H₁₉O₂P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NTNUDYROPUKXNA-UHFFFAOYSA-N
M.W :	334.35	Pubchem ID :	17453
Synonyms :

Calculated chemistry of [ 2605-67-6 ]

Physicochemical Properties

Num. heavy atoms :	24
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.05
Num. rotatable bonds :	5
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	103.17
TPSA :	36.11 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) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.98
Log Po/w (WLOGP) :	2.96
Log Po/w (MLOGP) :	4.51
Log Po/w (SILICOS-IT) :	5.19
Consensus Log Po/w :	3.33

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.65
Solubility :	0.00757 mg/ml ; 0.0000226 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.44
Solubility :	0.0122 mg/ml ; 0.0000363 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.64
Solubility :	0.00000771 mg/ml ; 0.0000000231 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.05

Safety of [ 2605-67-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P310+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501	UN#:	2811
Hazard Statements:	H301-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2605-67-6 ]

* 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.

Downstream synthetic route of [ 2605-67-6 ]

[ 2605-67-6 ] Synthesis Path-Downstream 1~9

1
[ 16619-55-9 ]
[ 2605-67-6 ]
[ 134898-25-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	In benzene Ambient temperature;

Reference： [1]Abdou, Wafaa M.; Ganoub, Neven A. F. [Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 60, # 1.2, p. 49 - 55]

2
[ CAS Unavailable ]
[ 2605-67-6 ]
[ 15790-88-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	In tetrahydrofuran for 4h; Reflux;	Representative example for the synthesis of methyl trans-2 pentenoate (MtE-b): In a round flask equipped with a magnetic bar TPA (10.02 g 0.03 mmol) was dissolved in anhydrous THF(150 mL), propionaldehyde (1.32 g, 0.03 mmol) was added to the solution and the reaction mixture was refluxed for 4 h. The reaction was filtered and evaporated for purification. The product was purified by flash chromatography on silica gel (hexanes/ethyl acetate) to give 5.2 g of a colorless liquid (M(E)E-b) (86% yield).
85%	In benzene for 2h; Heating;
85%	In benzene for 2h; Heating;

83%	In benzene Heating;
65%	In dichloromethane at 20℃; for 20h; Inert atmosphere; Sealed tube;

Reference： [1]Pérez-Venegas, Mario; Reyes-Rangel, Gloria; Neri, Adrián; Escalante, Jaime; Juaristi, Eusebio [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1728 - 1734]
[2]Kandula, SubbaRao V.; Kumar, Pradeep [Tetrahedron Letters, 2003, vol. 44, # 9, p. 1957 - 1958]
[3]Kandula, Subba Rao V.; Kumar, Pradeep [Tetrahedron Asymmetry, 2005, vol. 16, # 19, p. 3268 - 3274]
[4]Fujita, Mari; Nagano, Takashi; Schneider, Uwe; Hamada, Tomoaki; Ogawa, Chikako; Kobayashi, Shu [Journal of the American Chemical Society, 2008, vol. 130, # 10, p. 2914 - 2915]
[5]Tang, King Hung Nigel; Uchida, Kanako; Nishihara, Kazuki; Ito, Mamoru; Shibata, Takanori [Organic Letters, 2022, vol. 24, # 6, p. 1313 - 1317]

3
[ 2605-67-6 ]
[ 1132669-90-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
71%	In toluene at 90℃; for 18h;

Reference： [1]Lautens, Mark; Marquardt, Tzvetelina [Journal of Organic Chemistry, 2004, vol. 69, # 14, p. 4607 - 4614]

4
[ 19306-93-5 ]
[ 21204-67-1 ]
[ 15227-42-6 ]
[ 2181-97-7 ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	In dichloromethane Ph3P=CHCO2Me was added to soln. Pt(IV) complex in CH2Cl2, react. mixt. was kept at room temp. for 3 h; solvent was evapd., residue was chromed. on silica using CH2Cl2/Et2O (9:1) as eluent;

Reference： [1]Wagner; Pakhomova; Bokach; Frausto da Silva; Vicente; Pombeiro; Kukushkin [Inorganic Chemistry, 2001, vol. 40, # 7, p. 1683 - 1689]

5
[ 673-22-3 ]
[ 21204-67-1 ]
[ 531-59-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With N,N-diethylaniline; at 210℃; for 2h;	Compound 6 was synthesized following a literature procedure. ADDIN EN.CITE Starevi2011251712517251717tefan StareviBroi, PetraTurk, SamoCesar, JokoRiner, Tea LaninikGobec, StanislavSynthesis and Biological Evaluation of (6- and 7-Phenyl) Coumarin Derivatives as Selective Nonsteroidal Inhibitors of 17beta-Hydroxysteroid Dehydrogenase Type 1Journal of Medicinal ChemistryJournal Of Medicinal ChemistryJ Med ChemJ. Med. Chem.248-6154120111 A mixture of 2-hydroxy-4-methoxybenzaldehyde (1.0 g, 6.58 mmol) and ((methoxycarbonyl)-methylene)triphenylphosphorane (2.75 g, 7.89 mmol) was heated in DMF (65 mL) at 210 C for 2 h. After cooling to room temperature, the reaction mixture was diluted with 5% HCl solution (70 mL) and extracted with ether. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and then filtered and concentrated in vacuum. The product was purified by column chromatography (0-20% ethyl acetate in petroleum ether). Yield: 822 mg (71%), white solid (mp 111-114 C). 1H NMR (400 MHz, CDCl3) delta 7.60 (d, J = 9.4 Hz, 1H), 7.33 (d, J = 8.6 Hz, 1H), 6.79 (dd, J = 8.6, 2.4 Hz, 1H), 6.73 (d, J = 2.4 Hz, 1H), 6.19 (d, J = 9.5 Hz, 1H), 3.82 (s, 3H). 13C NMR (100 MHz, CDCl3) delta 162.76, 161.16, 155.77, 143.54, 128.83, 112.89, 112.45, 100.75, 55.75.

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 5204 - 5213
[2]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3531 - 3539
[3]Journal of Medicinal Chemistry,2011,vol. 54,p. 248 - 261

6
[ 2605-67-6 ]
[ 140174-48-7 ]
[ 1372976-40-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: methyl (triphenylphosphoranylidene)acetate With dimethylbromosulphonium bromide In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: 4-formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide With triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere;

Reference： [1]Jiang, Biao; Wang, Jue; Huang, Zuo-Gang [Organic Letters, 2012, vol. 14, # 8, p. 2070 - 2073]

7
[ 154748-49-9 ]
[ 2605-67-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
96%	In toluene Reflux; Inert atmosphere;	II.1.1 (3-tert-Butoxycarbonylaminocyclobutylidene)acetic acid methyl ester To a solution of (3-oxo-cyclobutyl)-carbamic acid tert-butyl ester (5.6 g, 30.2 mmol) in anhydrous toluene (100 mL) was added methyl (triphenylphosphoranylidene)- acetate (10.7 g, 45.4 mmol) and heated to reflux overnight under N2. After cooling to room temperature, the mixture was poured into water and extracted with EA. The organic phase was dried over Na2S04, concentrated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (eluted with PE:EA = 20: 1) to give the title compound (7 g, yield 96 %) as a white solid. 1H NMR (400 MHz, CDCl3): δ 5.71 (s, 1H), 4.86 (br, 1H), 4.25 (br, 1H), 3.70 (s, 3H), 3.60 (br, 1H), 3.23-3.18 (br, 1Η),2.97-2.92 (br, 1H), 2.79-2.73 (br, 1H), 1.46 (s, 9H).
78.8%	In dichloromethane at 20℃; for 48h;
76.8%	In toluene for 16h; Inert atmosphere; Reflux;	2.2 Step 2: Step 2: Methyl 2-(3-((tert-butoxycarbonyl)amino)cyclobutylidene)acetate Tert-butyl (3-oxocyclobutyl)carbamate (450 mg, 2.43 mmol) and toluene (20 mL) were added to a 50 mL eggplant-shaped flask successively, followed by the slow addition of methyl (triphenylphosphoranylidene)acetate (1.22 g, 3.64 mmol). The reaction solution was refluxed under a nitrogen atmosphere for 16 hours, cooled, and concentrated to dryness by rotary evaporation to obtain the crude product. The crude product was purified by column chromatography (petroleum ether/ethyl acetate: 6/1) to obtain methyl 2-(3-((tert-butoxycarbonyl)amino)cyclobutylidene)acetate (450 mg, yield: 76.8%). 1H NMR (400 MHz, CDCl3) δ 5.76 - 5.66 (m, 1H), 4.80 (br, 1H), 4.24 (s, 1H), 3.69 (s, 3H), 3.63 - 3.49 (m, 1H), 3.27 - 3.10 (m, 1H), 3.00 - 2.86 (m, 1H), 2.82 - 2.64 (m, 1H), 1.45 (s, 9H).

76.8%	In toluene for 16h; Inert atmosphere; Reflux;	2.2 Step 2: Step 2: Methyl 2-(3-((tert-butoxycarbonyl)amino)cyclobutylidene)acetate Tert-butyl (3-oxocyclobutyl)carbamate (450 mg, 2.43 mmol) and toluene (20 mL) were added to a 50 mL eggplant-shaped flask successively, followed by the slow addition of methyl (triphenylphosphoranylidene)acetate (1.22 g, 3.64 mmol). The reaction solution was refluxed under a nitrogen atmosphere for 16 hours, cooled, and concentrated to dryness by rotary evaporation to obtain the crude product. The crude product was purified by column chromatography (petroleum ether/ethyl acetate: 6/1) to obtain methyl 2-(3-((tert-butoxycarbonyl)amino)cyclobutylidene)acetate (450 mg, yield: 76.8%). 1H NMR (400 MHz, CDCl3) δ 5.76 - 5.66 (m, 1H), 4.80 (br, 1H), 4.24 (s, 1H), 3.69 (s, 3H), 3.63 - 3.49 (m, 1H), 3.27 - 3.10 (m, 1H), 3.00 - 2.86 (m, 1H), 2.82 - 2.64 (m, 1H), 1.45 (s, 9H).
		2.2 Step 2: Step 2: Methyl 2-(3-((tert-butoxycarbonyl)amino)cyclobutylidene)acetate Tert-butyl (3-oxocyclobutyl)carbamate (450 mg, 2.43 mmol) and toluene (20 mL) were added to a 50 mL eggplant-shaped flask successively, followed by the slow addition of methyl (triphenylphosphoranylidene)acetate (1.22 g, 3.64 mmol). The reaction solution was refluxed under a nitrogen atmosphere for 16 hours, cooled, and concentrated to dryness by rotary evaporation to obtain the crude product. The crude product was purified by column chromatography (petroleum ether/ethyl acetate: 6/1) to obtain methyl 2-(3-((tert-butoxycarbonyl)amino)cyclobutylidene)acetate (450 mg, yield: 76.8%). 1H NMR (400 MHz, CDCl3) δ 5.76 - 5.66 (m, 1H), 4.80 (br, 1H), 4.24 (s, 1H), 3.69 (s, 3H), 3.63 - 3.49 (m, 1H), 3.27 - 3.10 (m, 1H), 3.00 - 2.86 (m, 1H), 2.82 - 2.64 (m, 1H), 1.45 (s, 9H).

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2014/64038, 2014, A1 Location in patent: Page/Page column 47
[2]Current Patent Assignee: CULLGEN SHANGHAI - WO2022/100710, 2022, A1 Location in patent: Page/Page column 149
[3]Current Patent Assignee: HANSOH PHARMACEUTICAL GROUP CO LTD - EP4053110, 2022, A1 Location in patent: Paragraph 0112-0114
[4]Current Patent Assignee: HANSOH PHARMACEUTICAL GROUP CO LTD - EP4053110, 2022, A1 Location in patent: Paragraph 0112-0114
[5]Current Patent Assignee: HANSOH PHARMACEUTICAL GROUP CO LTD - EP4053110, 2022, A1

8
[ 708-76-9 ]
[ 21204-67-1 ]
[ 487-06-9 ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 5204 - 5213

9
[ 1638771-06-8 ]
[ 2605-67-6 ]
[ 2247990-59-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	In tetrahydrofuran at 20℃; for 18h;	14.2; 15.2 Step 2: (E)-methyl 3-(3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1] pentan-1- yl)acrylate: tert-butyl (3-formylbicyclo[1 .1. 1]pentan-1-yl)carbamate (1 eq.) from the previous step was dissolved in THF (0.034 M) and methyl 2-(triphenylphosphoranylidene)acetate (1 eq.) was added. The resulting solution was stirred at RT for 18 h and then diluted with TBME and washed sequentially with 1 N aq. HC1, water and brine. The organic extract was then dried over Mg504 and filtered. Concentration of the filtrate in vacuo furnished the crude reaction product as a viscous oil. Further purification by way of column chromatography (5i02, 9:1 (v/v) Hex:EtOAc to 3:7 (v/v) Hex:EtOAc) afforded the product as a colorless oil (94% yield).

Reference： [1]Current Patent Assignee: TEMPEST THERAPEUTICS INC - WO2018/195123, 2018, A1 Location in patent: Paragraph 00289

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H316	Causes mild skin irritation
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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

[ CAS No. 2605-67-6 ] {[proInfo.proName]}

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