[ CAS No. 311-46-6 ] {[proInfo.proName]}

Name: 311-46-6|Ethyl 2-(dimethoxyphosphoryl)acetate|97%
Brand: Ambeed
SKU: A132470
Rating: 96 (27 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

DV 2D 3D

3d Animation Molecule Structure of 311-46-6

Structure of 311-46-6 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 311-46-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 311-46-6 ]

SDS Specification

Alternatived Products of [ 311-46-6 ]

Product Details of [ 311-46-6 ]

CAS No. :	311-46-6	MDL No. :	MFCD00015677
Formula :	C₆H₁₃O₅P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HUNISAHOCCASGM-UHFFFAOYSA-N
M.W :	196.14	Pubchem ID :	67555
Synonyms :

Calculated chemistry of [ 311-46-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.07
TPSA :	71.64 Å²

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) :	-7.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	-0.24
Log Po/w (WLOGP) :	1.04
Log Po/w (MLOGP) :	-0.18
Log Po/w (SILICOS-IT) :	-0.23
Consensus Log Po/w :	0.48

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.51
Solubility :	60.8 mg/ml ; 0.31 mol/l
Class :	Very soluble
Log S (Ali) :	-0.81
Solubility :	30.6 mg/ml ; 0.156 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.04
Solubility :	17.7 mg/ml ; 0.0904 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.35

Safety of [ 311-46-6 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P362+P364-P403+P233-P501	UN#:	3082
Hazard Statements:	H302-H315-H318-H335-H411	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 311-46-6 ]

* 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 [ 311-46-6 ]
Downstream synthetic route of [ 311-46-6 ]

[ 311-46-6 ] Synthesis Path-Upstream 1~9

1
[ 4746-97-8 ]
[ 311-46-6 ]
[ 51656-91-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 1 h; Stage #2: at 0 - 20℃; for 16 h;	Triethylphosphono acetate (6lmL, 0.3Omol) was added to a suspention KOBu-t(33g, 0.3Omol) in DMF (200mL) at 0 00, stirred for lh at RT. A solution of 1,4- dioxaspiro[4.5]decan-8-one (40g, 0.25mo1) in DMF (200mL) was added at 0 C and the whole then stirred for 16h at RT. The reaction mixture was quenched with sat NH4CI solutionand extracted with ethyl acetate (2X500mL). The combined organic layer was washed with water, brine,dried over Na2SO4 and distilled under reduced pressure to afford crude, which was purified by column chromatography (silica gel; 60-l20mesh); the product eluted with 10- 15percentethyl acetate in hexane to yield 50.Og (86percent) of Ethyl-2-(1,4-dioxaspiro-[4.5]-decan-8- ylidene)-acetate as liquid.

Reference： [1] Patent: WO2016/8582, 2016, A1, . Location in patent: Page/Page column 65
[2] Journal of the American Chemical Society, 1991, vol. 113, # 21, p. 8016 - 8024
[3] Tetrahedron Letters, 1993, vol. 34, # 22, p. 3505 - 3508

2
[ 105-39-5 ]
[ 121-45-9 ]
[ 311-46-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	at 150℃; for 0.166667 h; Large scale	The dry and clean 500mL coil was heated to 150 degree celcius , take the compound 1 (standard atmospheric pressure boiling point of 142 ~145 ° C) 1000 g (0.7 eq. 8.16 mol) was placed in a shot bottle A,Add 4000g toluene dilution, take trimethyl phosphite (standard Atmospheric pressure at the boiling point of 112 ° C) 1417g (1.0eq.11.42mol) placed in the bottle B, adding 3583g toluene diluted until The coil was started at a stable temperature and pump A (compound 1 in toluene): 25.0 g / min, pump B (trimethyl phosphite):25.0 g / min. Residence time 10min, the reaction pressure is 0.5 ~ 2.0Mpa. The discharge port is directly connected to the thin film evaporation device, control The pressure of 4 ~ 10 × 102Pa, temperature 95 ~ 105 , the final product Compound 3 (boiling point 110 ~ 112 , 466Pa) 1344 g, yield 84percent.

Reference： [1] Patent: CN107163079, 2017, A, . Location in patent: Paragraph 0068; 0069; 0070; 0071
[2] Bulletin de la Societe Chimique de France, 1965, p. 1925 - 1930
[3] Tetrahedron Letters, 1999, vol. 40, # 8, p. 1455 - 1458

3
[ 623-73-4 ]
[ 121-45-9 ]
[ 311-46-6 ]

Reference： [1] Tetrahedron, 2008, vol. 64, # 32, p. 7555 - 7560
[2] Journal of the American Chemical Society, 2003, vol. 125, # 20, p. 6034 - 6035

4
[ 67-56-1 ]
[ 16139-79-0 ]
[ 311-46-6 ]
[ 625396-71-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 1, p. 131 - 134

5
[ 67-56-1 ]
[ 16139-79-0 ]
[ 311-46-6 ]
[ 5927-18-4 ]
[ 625396-69-2 ]
[ 625396-71-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 1, p. 131 - 134

6
[ 67-56-1 ]
[ 42451-44-5 ]
[ 311-46-6 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1976, vol. 46, p. 529 - 534[2] Zhurnal Obshchei Khimii, 1976, vol. 46, # 3, p. 534 - 540

7
[ 105-36-2 ]
[ 121-45-9 ]
[ 311-46-6 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1964, vol. 259, p. 2244 - 2247

8
[ 67-56-1 ]
[ 16139-79-0 ]
[ 311-46-6 ]
[ 5927-18-4 ]
[ 625396-69-2 ]
[ 625396-71-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 1, p. 131 - 134

9
[ 311-46-6 ]
[ 79099-07-3 ]
[ 135716-08-4 ]

Reference： [1] Patent: US2003/229074, 2003, A1, . Location in patent: Page 20
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 19, p. 5652 - 5656

[ 311-46-6 ] Synthesis Path-Downstream 1~88

1
[ 311-46-6 ]
[ 33734-93-9 ]

Reference： [1]Doklady Akademii Nauk SSSR,1951,vol. 79,p. 605
Chem.Abstr.,1955,p. 15768

2
[ 311-46-6 ]
[ 57053-96-0 ]
[ 57053-97-1 ]

Reference： [1]Patent: DE2500344,1975,
Chem.Abstr.,1975,vol. 83

3
[ 105-39-5 ]
[ 121-45-9 ]
[ 311-46-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	In toluene; at 150℃; under 3750.38 - 15001.5 Torr; for 0.166667h;Large scale;	The dry and clean 500mL coil was heated to 150 degree celcius , take the compound 1 (standard atmospheric pressure boiling point of 142 ~145 C) 1000 g (0.7 eq. 8.16 mol) was placed in a shot bottle A,Add 4000g toluene dilution, take trimethyl phosphite (standard Atmospheric pressure at the boiling point of 112 C) 1417g (1.0eq.11.42mol) placed in the bottle B, adding 3583g toluene diluted until The coil was started at a stable temperature and pump A (compound 1 in toluene): 25.0 g / min, pump B (trimethyl phosphite):25.0 g / min. Residence time 10min, the reaction pressure is 0.5 ~ 2.0Mpa. The discharge port is directly connected to the thin film evaporation device, control The pressure of 4 ~ 10 × 102Pa, temperature 95 ~ 105 , the final product Compound 3 (boiling point 110 ~ 112 , 466Pa) 1344 g, yield 84%.

Reference： [1]Patent: CN107163079,2017,A .Location in patent: Paragraph 0068; 0069; 0070; 0071
[2]Bulletin de la Societe Chimique de France,1965,p. 1925 - 1930
[3]Tetrahedron Letters,1999,vol. 40,p. 1455 - 1458

4
[ 105-36-2 ]
[ 121-45-9 ]
[ 311-46-6 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1964,vol. 259,p. 2244 - 2247

5
[ 311-46-6 ]
[ 75-50-3 ]
[ 814-48-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1966,p. 932 - 937
[2]Bulletin de la Societe Chimique de France,1965,p. 1925 - 1930

6
[ 1466-88-2 ]
[ 311-46-6 ]
[ 133505-27-8 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1982,vol. 36,p. 561 - 562

7
[ 4746-97-8 ]
[ 311-46-6 ]
[ 51656-91-8 ]

Yield	Reaction Conditions	Operation in experiment
86%		Triethylphosphono acetate (6lmL, 0.3Omol) was added to a suspention KOBu-t(33g, 0.3Omol) in DMF (200mL) at 0 00, stirred for lh at RT. A solution of 1,4- dioxaspiro[4.5]decan-8-one (40g, 0.25mo1) in DMF (200mL) was added at 0 C and the whole then stirred for 16h at RT. The reaction mixture was quenched with sat NH4CI solutionand extracted with ethyl acetate (2X500mL). The combined organic layer was washed with water, brine,dried over Na2SO4 and distilled under reduced pressure to afford crude, which was purified by column chromatography (silica gel; 60-l20mesh); the product eluted with 10- 15%ethyl acetate in hexane to yield 50.Og (86%) of Ethyl-2-(1,4-dioxaspiro-[4.5]-decan-8- ylidene)-acetate as liquid.

Reference： [1]Patent: WO2016/8582,2016,A1 .Location in patent: Page/Page column 65
[2]Journal of the American Chemical Society,1991,vol. 113,p. 8016 - 8024
[3]Tetrahedron Letters,1993,vol. 34,p. 3505 - 3508

8
[ 3592-47-0 ]
[ 311-46-6 ]
[ 87482-94-8 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 4502 - 4508

9
[ 6728-26-3 ]
[ 311-46-6 ]
[ 60388-61-6 ]

Reference： [1]Journal of the Indian Chemical Society,1990,vol. 67,p. 37 - 38

10
[ 2548-87-0 ]
[ 311-46-6 ]
[ 7328-34-9 ]

Reference： [1]Journal of the Indian Chemical Society,1990,vol. 67,p. 995 - 996

11
[ 311-46-6 ]
[ 21573-31-9 ]
[ 78426-45-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 257 - 259

12
[ 311-46-6 ]
[ 30390-50-2 ]
[ 28380-08-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 760 - 762

13
[ 311-46-6 ]
[ 2426-60-0 ]
[ 138474-94-9 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1991,vol. 41,p. 1068 - 1071

14
[ 311-46-6 ]
[ 57323-08-7 ]
[ 115349-61-6 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 5255 - 5258

15
[ 311-46-6 ]
[ 124853-23-2 ]
[ 124853-24-3 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 3173 - 3188

16
[ 311-46-6 ]
[ 124853-23-2 ]
[ 124853-24-3 ]
(E)-3-{(2S,3S)-3-[(S)-1-((3R,5R,6S,8S,9S,10R,13S,14S,17R)-3,6-Diacetoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethyl]-oxiranyl}-4-methyl-pent-2-enoic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1989,p. 612 - 613

17
[ 311-46-6 ]
[ 130592-49-3 ]
[ 130592-51-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 606 - 610

18
[ 311-46-6 ]
[ 96754-41-5 ]
[ 130592-52-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 606 - 610

19
[ 311-46-6 ]
[ 130592-50-6 ]
[ 130592-53-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 606 - 610

20
[ 311-46-6 ]
[ 129047-38-7 ]
[ 129047-39-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 284 - 286

21
[ 311-46-6 ]
[ 115008-76-9 ]
[ 130759-59-0 ]
[ 130743-20-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2281 - 2286

22
[ 311-46-6 ]
[ 52911-90-7 ]
[ 57749-86-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1035 - 1042

23
[ 311-46-6 ]
[ 101128-90-9 ]
[ 101128-91-0 ]
[ 101128-91-0 ]

Reference： [1]Liebigs Annalen der Chemie,1985,vol. 1985,p. 2151 - 2164

24
[ 311-46-6 ]
[ 83323-72-2 ]
ethyl (2Z,8E)-3,7,11-trimethyl-2,8-dodecadienoate [ No CAS ]
ethyl (2E,8E)-3,7,11-trimethyl-2,8-dodecadienoate [ No CAS ]

Reference： [1]Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques,1980,vol. 28,p. 599 - 607

25
[ 311-46-6 ]
[ 33439-27-9 ]
ethyl 2-(1-tosylpiperidin-4-ylidene)acetate [ No CAS ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 3505 - 3508

26
[ 311-46-6 ]
[ 108-94-1 ]
[ 1552-92-7 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 3505 - 3508

27
[ 311-46-6 ]
[ 108-24-7 ]
[ 115008-76-9 ]
[ 130759-59-0 ]
[ 130743-20-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2281 - 2286

28
[ 311-46-6 ]
[ 403-42-9 ]
[ 147471-19-0 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1041 - 1047

29
[ 311-46-6 ]
[ 583-60-8 ]
[ 27801-76-9 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 3505 - 3508

30
[ 311-46-6 ]
[ 1131-62-0 ]
[ 67409-10-3 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1041 - 1047

31
[ 311-46-6 ]
[ 591-24-2 ]
[ 85048-23-3 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 3505 - 3508

32
[ 311-46-6 ]
[ 564-94-3 ]
trans-2-(2-ethoxycarbonylvinyl)-6,6-dimethyl-2-norpinene [ No CAS ]

Reference： [1]Russian Chemical Bulletin,1994,vol. 43,p. 1684 - 1687
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation),1994,p. 1779 - 1782

33
[ 311-46-6 ]
[ 35633-35-3 ]
[ 323195-82-0 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 2279 - 2280

34
[ 311-46-6 ]
[ 127793-62-8 ]
[ 176907-54-3 ]

Reference： [1]Chemical Communications,1996,p. 737 - 738

35
[ 311-46-6 ]
[ 131216-47-2 ]
[ 151965-41-2 ]

Reference： [1]Chemical Communications,1996,p. 737 - 738

36
[ 311-46-6 ]
[ 90-02-8 ]
dimethyl (2-oxo-2H-chromen-3-yl)phosphonate [ No CAS ]
2-Methoxy-2-oxo-2H-2λ⁵-benzo[e][1,2]oxaphosphinine-3-carboxylic acid ethyl ester [ No CAS ]
diethyl 6a,6b,12a,12b-tetrahydro-exo,exo-6,12-dimethoxy-endo,endo-6,12-dioxo-6H,12H-cyclobuta[1,2-c:3,4-c']bis[1,2]benzoxaphosphorine-trans-6a,12a-dicarboxylate [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 12597 - 12612
[2]Tetrahedron,1996,vol. 52,p. 12597 - 12612

37
[ 311-46-6 ]
[ 56583-95-0 ]
[ 193006-90-5 ]
[ 193006-89-2 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 1963 - 1966

38
[ 311-46-6 ]
[ 113800-12-7 ]
ethyl (Z)-3-(dimethyl(phenyl)silyl)-4-(phenyl)-2-butenoate [ No CAS ]
[ 889130-05-6 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 1963 - 1966

39
[ 311-46-6 ]
[ 34159-46-1 ]

Reference： [1]Tetrahedron Asymmetry,2007,vol. 18,p. 2427 - 2436

40
[ 13520-92-8 ]
[ 311-46-6 ]
Zr⁽⁴⁺⁾*2O₂P(O)CH₂CO₂H^(2-) = Zr(O₂P(O)CH₂CO₂H)2 [ No CAS ]

Reference： [1]Chemical Communications,1999,p. 1997 - 1998

41
[ 311-46-6 ]
[ 79099-07-3 ]
[ 135716-08-4 ]

Yield	Reaction Conditions	Operation in experiment
		[0140] A 2L three neck round bottom flask is charged with of ethyl dimethylphosphonoacetate and 750 ml of anhydrous THF while stirring under N2 atmosphere at 0 C. Sodium hydride (1.1 equivalents, 60% in dispersion oil) is slowly added and the mixture is stirred for 1.5 hours. Boc-protected piperidin-4-one (0.9 equivalents) is added all at once. The reaction mixture is allowed to warm to room temperature and stirred overnight. The reaction mixture is quenched with saturated NaHCO3 and transferred to a separatory funnel. The organic phase is removed and the aqueous phase is washed three times with ethyl acetate. The organic layers are combined and washed two times with brine. The organic layer is then dried over anhydrous MgSO4 and vacuum filtered. The filtrate is concentrated under reduced pressure to afford the unsaturated ester.

Reference： [1]Patent: US2003/229074,2003,A1 .Location in patent: Page 20
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5652 - 5656

42
[ 311-46-6 ]
[ 785828-28-6 ]
(R)-4-((Z)-2-ethoxycarbonyl-1-methyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]
[ 1168208-13-6 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 2756 - 2759

43
[ 311-46-6 ]
[ 1193-47-1 ]
ethyl (2E)-(2,2-dimethylcyclohexylidene)acetate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 9773 - 9784

44
2-(3-chloro-propane-1-sulfonyl)-benzaldehyde [ No CAS ]
[ 311-46-6 ]
[ 1226999-25-2 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 1885 - 1894

45
[ 311-46-6 ]
[ 1283115-91-2 ]
C₂₃H₄₅O₈P [ No CAS ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1284 - 1287

46
[ 311-46-6 ]
[ 1283115-92-3 ]
C₂₄H₄₇O₈P [ No CAS ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1284 - 1287

47
[ 311-46-6 ]
[ 1283115-93-4 ]
C₂₆H₅₁O₈P [ No CAS ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1284 - 1287

48
[ 311-46-6 ]
[ 1283115-94-5 ]
C₂₇H₅₃O₈P [ No CAS ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1284 - 1287

49
[ 311-46-6 ]
C₂₁H₄₁O₆P [ No CAS ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1284 - 1287

50
[ 311-46-6 ]
C₂₁H₄₃O₆P [ No CAS ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1284 - 1287

51
[ 311-46-6 ]
[ 55833-20-0 ]
C₂₃H₄₅O₇P [ No CAS ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1284 - 1287

52
[ 311-46-6 ]
[ 179108-67-9 ]
C₂₆H₅₁O₇P [ No CAS ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1284 - 1287

53
[ 311-46-6 ]
[ 128184-01-0 ]
[ 1364054-27-2 ]

Reference： [1]Helvetica Chimica Acta,2012,vol. 95,p. 197 - 210

54
[ 311-46-6 ]
[ 58551-83-0 ]
[ 1257121-73-5 ]

Yield	Reaction Conditions	Operation in experiment
87%		D38: Ethyl (2£)-3-(2,4,6-trifluorophenyl)-2-propenoateTo the solution of ethyl [bis(methyloxy)phosphoryl]acetate (1.980 mL, 11.99 mmol) in THF-DMF (60 mL, v/v=5: 1) at 0 C was added t-BuOK (1.458 g, 12.99 mmol) portion wise. The resultant mixture was stirred at room temperature for 30 minutes, then mixed with a solution of <strong>[58551-83-0]2,4,6-trifluorobenzaldehyde</strong> (1.6 g, 9.99 mmol) in THF (10 mL) at 0 C. It was allowed to warm to room temperature and the mixture was stirred for 45 min. It was mixed with aqueous ammonium chloride and then extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2S04, filtered, and concentrated. The residue was purified by a flash column chromatography to give the title compound as a pale yellow oil (2.0 g, 87 % yield). LCMS: rt = 3.52 min, [M+H+] = 231.1

Reference： [1]Patent: WO2012/76435,2012,A1 .Location in patent: Page/Page column 38

55
[ 311-46-6 ]
[ 1378372-30-5 ]
[ 1378372-23-6 ]
[ 1378372-47-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2714 - 2717

56
[ 311-46-6 ]
[ 1378372-31-6 ]
[ 1378372-24-7 ]
[ 1378372-48-5 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2714 - 2717

57
[ 110-62-3 ]
[ 311-46-6 ]
[ 2351-88-4 ]

Yield	Reaction Conditions	Operation in experiment
37%	With sodium hydride; In tetrahydrofuran; at 20℃; for 12h;	To a solution of 60% NaH (34.8g, 870mmol) in 500mL dry THF was added <strong>[311-46-6]ethyl 2-(dimethoxyphosphoryl)acetate</strong> (102g, 522mmo1). Then a solution of Compound 4-1 (30g, 348mmol) in 100mL dry THF was added to the mixture. The reaction mixture was stirred for 12 hours at room temperature. To the reaction mixture was added saturated aqueous NH4Cl. The reaction mixture was concentrated and extracted with ethyl acetate (3x50mL). The organic phase was washed with water (3x25mL), brine (3x25mL), dried with anhydrous Na2SO4, and concentrated in vacuo to give a crude product. The residue was purified with column chromatography (ethyl acetate in petroleum ether 10% v/v) to give Compound 4-2 (20 g, Yield 37 %) as a yellow liquid. m/z: 157 [M+H]+.
37%	With sodium hydride; In tetrahydrofuran; at 20℃; for 12h;	A. Preparation of Compound 4-2 39] To a solution of 60% NaH (34.8g, 870mmol) in 500mL dry THF was added ethyl 2- (dimethoxyphosphoryl)acetate (102g, 522mmol). Then a solution of Compound 4-1 (30g, 348mmol) in lOOmL dry THF was added to the mixture. The reaction mixture was stirred for 12 hours at room temperature. To the reaction mixture was added saturated aqueous NH4C1. The reaction mixture was concentrated and extracted with ethyl acetate (3x50mL). The organic phase was washed with water (3x25mL), brine (3x25mL), dried with anhydrous Na2S04, and concentrated in vacuo to give a crude product. The residue was purified with column chromatography (ethyl acetate in petroleum ether 10% v/v) to give Compound 4-2 (20 g, Yield 37 %) as a yellow liquid, m/z: 157 [M+H]+

Reference： [1]Patent: WO2013/13190,2013,A1 .Location in patent: Paragraph 00228
[2]Patent: WO2014/116651,2014,A1 .Location in patent: Paragraph 00239

58
[ 75-77-4 ]
[ 311-46-6 ]
[ 65868-40-8 ]
[ 74-88-4 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium iodide; In acetonitrile; at 30 - 70℃; for 1.75h;	Embodiment 1, 8 ml acetonitrile and 5 g non-radioactive potassium iodide are sequentially added into a 50mlround-bottomed reaction flask, wherein the non-radioactive potassium iodide is used to simulate a radioactive iodinesource (similarly hereinafter, which is not repeated in the following embodiments); subsequently, 2.5 ml ethyl dimethylphosphonoacetateand 3.8 ml trimethyl chlorosilane are added into the reaction flask and further mixed to be uniform;after that, such chemicals react with each other at 30C for 15min under a magnetic stirring, and the reagent for testingpurification capacity of radioactive gas in nuclear power plant is obtained thereafter. A reflux condensing is carried outon the reagent at 70C for 1.5h to collect the non-radioactive methyl iodide. According to a density analysis, the yield ofthe non-radioactive methyl iodide in the collected liquid is about 46%.

Reference： [1]Patent: EP2581359,2013,A1 .Location in patent: Paragraph 0050

59
[ 311-46-6 ]
[ 160744-60-5 ]
(E)-ethyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)acrylate [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 775 - 785

60
[ 311-46-6 ]
C₁₇H₁₉NO₃ [ No CAS ]
C₂₀H₂₃NO₄ [ No CAS ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 5781 - 5784

61
[ 311-46-6 ]
[ 79-77-6 ]
[ 17974-55-9 ]

Reference： [1]Organic Process Research and Development,2005,vol. 9,p. 302 - 305

62
[ 311-46-6 ]
[ 1204747-72-7 ]
C₂₄H₂₁N₃O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6569 - 6576

63
[ 311-46-6 ]
[ 128252-95-9 ]
ethyl bromo(dimethoxyphosphoryl)acetate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 152 - 163

64
[ 311-46-6 ]
ethyl bromo(dimethoxyphosphoryl)acetate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 152 - 163

65
[ 311-46-6 ]
[ 1555558-54-7 ]
[ 1555558-57-0 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 152 - 163
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 152 - 163

66
[ 311-46-6 ]
3-[(R)-3-allyl-3-(S)-2-((methoxymethyl)pyrrolidine-1-carbonyl)-4-oxo-cyclohex-1-enyl]propionaldehyde [ No CAS ]
(E)-5-[(R)-3-allyl-3-((S)-2-(methoxymethyl)pyrrolidine-1-carbonyl)-4-oxo-cyclohex-1-enyl]pent-2-enoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		Lithium bistrimethylsilyl amide(LHMDS) (2.3mL, 2.3 mmol, 1M in THF) was added to a solution of dimethoxyphosphoryl)acetic acid ethyl ester (0.418 mL, 2.1 mmol) in THF (30 mL) and stirred at 25 C for 20 min. A solution of aldehyde 8 (638 mg, 1.91 mmol) in THF (20 mL) was added and the resulting yellow reaction was stirred for 14 h at 25 C,followed by dilution with NH4Cl (s) and ethyl acetate. The organic layer was separated and concentrated under reduced pressure to afford an oil that was purified with column chromatography (24 g column, 0-100% EtOAc/heptane) to afford the ester 1a as an oil (518 mg, 67 %). 1HNMR (CDCl3, mix of rotamers) d 6.96-6.86 (m, 1 H), 5.87-5.83 (d, 1 H),5.81-5.75 (m, 1 H), 5.41 (s, 1 H), 5.06-5.04 (d, 1 H), 5.04-5.01 (d, 1 H),4.35-4.25 (m, 1 H), 4.21-4.16 (q, 2 H), 3.63-3.6 (m, 1 H), 3.26 (t, 3 H),3.38-3.26 (m, 2 H), 3.05-3.07 (m, 1 H), 2.66-2.64 (d, 2 H), 2.33-2.23 (m, 6 H),1.95-1.87 (m, 3 H), 1.87-1.68 (m, 3 H), 1.77-1.69 ( m, 1 H), 1.36-1.33 (m, 1H), 1.33-1.25 (t, 3 H). 13C NMR (CDCl3,mix of rotamers) d207.45, 168.47, 166.20, 147.44. 138.37, 134.24, 123.52, 122.28, 117.95, 71.55,62.48, 61.04, 58.98, 57.74, 46.39, 41.45, 36.91, 35.47, 30.73, 28.66, 26.60,24.75, 14.43. ESMS (H+) = 404.2, LCMS tR =2.82

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 4616 - 4618

67
[ 311-46-6 ]
C₁₅H₁₉NO₂ [ No CAS ]
[ 86459-88-3 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 1307 - 1311
Angew. Chem.,2015,vol. 127,p. 1323 - 1327,5

68
[ 311-46-6 ]
C₃₀H₃₀N₂O₂ [ No CAS ]
C₃₄H₃₆N₂O₃ [ No CAS ]