124755-24-4|Ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)acetate| Ambeed

CAS No. :	124755-24-4
Formula :	C₈H₁₁F₆O₅P
M.W :	332.13
SMILES Code :	CCOC(=O)CP(=O)(OCC(F)(F)F)OCC(F)(F)F
MDL No. :	MFCD01318337
InChI Key :	HBYHPBCAZBLFTD-UHFFFAOYSA-N
Pubchem ID :	11759356

Safety of [ 124755-24-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H227-H315-H319-H335
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 124755-24-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	0
Fraction Csp3	0.88
Num. rotatable bonds	10
Num. H-bond acceptors	11.0
Num. H-bond donors	0.0
Molar Refractivity	53.07
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.64 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.96
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.99
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	5.42
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.42
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.58

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.49
Solubility	1.07 mg/ml ; 0.00321 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.12
Solubility	0.252 mg/ml ; 0.000757 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.82
Solubility	0.503 mg/ml ; 0.00151 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.91 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.47

Application In Synthesis of [ 124755-24-4 ]

* 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.

Downstream synthetic route of [ 124755-24-4 ]

[ 124755-24-4 ] Synthesis Path-Downstream 1~54

1
[ 119-61-9 ]
[ 124755-24-4 ]
[ 17792-17-5 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 869 - 875.

2
[ 124755-24-4 ]
[ 76985-26-7 ]
[ 128443-00-5 ]

References: [1]Tetrahedron,1989,vol. 45,p. 391 - 402.

3
[ 124755-24-4 ]
(2R,3R)-3-(2-Benzyloxy-ethyl)-2-methyl-oxirane-2-carbaldehyde [ No CAS ]
[ 138152-66-6 ]
[ 138283-90-6 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 115 - 123.

4
[ 124755-24-4 ]
[ 114762-39-9 ]
[ 128442-98-8 ]

References: [1]Tetrahedron,1989,vol. 45,p. 391 - 402.

5
[ 124755-24-4 ]
[ 108-94-1 ]
[ 1552-92-7 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 869 - 875.
[2]Synthetic Communications,1990,vol. 20,p. 869 - 875.

6
[ 124755-24-4 ]
[ 100-52-7 ]
[ 4610-69-9 ]
[ 4192-77-2 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 869 - 875.

7
Lithium; (E)-2-[bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-1-ethoxy-ethenolate [ No CAS ]
[ 124755-24-4 ]

References: [1]Synthetic Communications,1991,vol. 21,p. 2391 - 2396.

8
[ 124755-24-4 ]
[ 120-92-3 ]
[ 1903-22-6 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 869 - 875.

9
[ 124755-24-4 ]
[ 98-86-2 ]
[ 945-93-7 ]
[ 945-93-7 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 869 - 875.

10
[ 124755-24-4 ]
[ 96-22-0 ]
[ 15249-93-1 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 869 - 875.

11
[ 124755-24-4 ]
[ 129600-97-1 ]
[ 161454-43-9 ]
[ 161454-44-0 ]

References: [1]Heterocycles,1994,vol. 38,p. 2253 - 2260.

12
[ 124755-24-4 ]
(R)-2-Methoxymethoxy-5-methyl-hex-4-enal [ No CAS ]
ethyl (4R,2Z)-4-O-(methoxymethyl)-7-methyl-2,6-octadienoate [ No CAS ]

References: [1]Synthetic Communications,1995,vol. 25,p. 203 - 214.

13
[ 124755-24-4 ]
6-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-hexanal [ No CAS ]
(E)-8-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-oct-2-enoic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,1996,vol. 52,p. 8143 - 8158.

14
[ 23100-12-1 ]
[ 124755-24-4 ]
[ 201293-11-0 ]

References: [1]Journal of Organic Chemistry,1998,vol. 63,p. 760 - 768.

15
[ 124755-24-4 ]
[ 98014-77-8 ]
(Z)-5-(Benzyl-tert-butoxycarbonyl-amino)-pent-2-enoic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 7621 - 7624.

16
[ 124755-24-4 ]
/PXJOB₁₅₅-1350/ [ No CAS ]
[ 124755-25-5 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 1540 - 1547.

17
[ 92466-70-1 ]
[ 105-36-2 ]
[ 124755-24-4 ]

References: [1]Organic Preparations and Procedures International,1999,vol. 31,p. 240 - 243.

18
[ 27607-77-8 ]
[ 124755-24-4 ]
[ 286458-76-2 ]
ethyl (4S,5R,6S,7R)(Z)-7-((2R,3S,4R)-3-bromo-2,4-dimethyltetrahydrofuran-2-yl)-4,6-dimethyl-7-(methanesulfonyloxy)-5-trimethylsilyloxyhept-2-enoate [ No CAS ]
[ 286458-78-4 ]

References: [1]Organic Letters,2000,vol. 2,p. 1669 - 1672.
[2]Organic Letters,2000,vol. 2,p. 1669 - 1672.

19
[ 124755-24-4 ]
[ 69610-41-9 ]
[ 104700-41-6 ]
[ 356788-89-1 ]

References: [1]Tetrahedron,2001,vol. 57,p. 4903 - 4923.

20
[ 124755-24-4 ]
[ 79069-50-4 ]
[ 104700-37-0 ]
[ 356788-81-3 ]

References: [1]Tetrahedron,2001,vol. 57,p. 4903 - 4923.

21
[ 124755-24-4 ]
[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-acetaldehyde [ No CAS ]
[ 339291-63-3 ]
(E)-4-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-2-methyl-but-2-enoic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 2692 - 2699.

22
[ 4501-58-0 ]
[ 124755-24-4 ]
(E)-2-Bromo-4-(2,2,3-trimethyl-cyclopent-3-enyl)-but-2-enoic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5929 - 5931.

23
[ 124755-24-4 ]
[ 102308-32-7 ]
[ 240137-29-5 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5929 - 5931.

24
[ 124755-24-4 ]
ethyl bis(2,2,2-trifluoroethyl)-dibromophosphonoacetate [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5929 - 5931.

25
[ 124755-24-4 ]
[ 555-16-8 ]
[ 91348-52-6 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5929 - 5931.

26
[ 124755-24-4 ]
[ 100-52-7 ]
[ 59106-34-2 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5929 - 5931.

27
[ 124755-24-4 ]
[ 123-11-5 ]
[ 871893-64-0 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5929 - 5931.

28
[ 124755-24-4 ]
[ 15186-48-8 ]
ethyl (S,E)-2-bromo-3-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-enoate [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5929 - 5931.

29
[ 40663-68-1 ]
[ 124755-24-4 ]
[ 515834-87-4 ]

References: [1]Synlett,2003,p. 87 - 90.

30
[ 124755-24-4 ]
(1S,6S)-1,3,5-Trimethyl-6-(4-nitro-phenyl)-cyclohexa-2,4-dienecarbaldehyde [ No CAS ]
(Z)-3-[(1R,6R)-1,3,5-Trimethyl-6-(4-nitro-phenyl)-cyclohexa-2,4-dienyl]-acrylic acid ethyl ester [ No CAS ]

References: [1]Organic Letters,2003,vol. 5,p. 1701 - 1704.

31
[ 18031-40-8 ]
[ 124755-24-4 ]
[ 639009-29-3 ]

References: [1]Tetrahedron,2003,vol. 59,p. 8919 - 8930.

32
[ 124755-24-4 ]
[ 197955-69-4 ]
(2Z,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid ethyl ester [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 161 - 164.

33
[ 124755-24-4 ]
[ 91202-70-9 ]
[ 817642-38-9 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 15968 - 15969.

34
[ 124755-24-4 ]
[ 72496-37-8 ]
[ 856675-66-6 ]
[ 322765-15-1 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 4762 - 4773.

35
[ 69152-87-0 ]
[ 124755-24-4 ]
[ 872326-43-7 ]
[ 144895-69-2 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 10576 - 10578.

36
[ 869348-28-7 ]
[ 124755-24-4 ]
[ 869348-29-8 ]

References: [1]Organic Letters,2005,vol. 7,p. 4819 - 4822.

37
[ 124755-24-4 ]
[ 100-52-7 ]
(E)-2-[Bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-3-phenyl-acrylic acid ethyl ester [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 2099 - 2100.

38
[ 124755-24-4 ]
[ 123-11-5 ]
ethyl (Z)-2-[bis(2,2,2-trifluoroethyl)phosphonato]-3-(4-methoxyphenyl)-2-propenoate [ No CAS ]
ethyl (E)-2-[bis(2,2,2-trifluoroethyl)phosphonato]-3-(4-methoxyphenyl)-2-propenoate [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 2099 - 2100.

39
[ 124755-24-4 ]
[ 1122-91-4 ]
(E)-2-[Bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-3-(4-bromo-phenyl)-acrylic acid ethyl ester [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 2099 - 2100.

40
[ 499144-88-6 ]
[ 124755-24-4 ]
[ 863921-79-3 ]
ethyl (2E,4E,7S)-7-(tert-butyldimethylsilyloxy)-8-(trityloxy)octa-2,4-dienoate [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 11291 - 11298.

41
[ 124755-24-4 ]
[ 354113-67-0 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5929 - 5931.

42
[ 757-95-9 ]
[ 124755-24-4 ]

References: [1]Synthetic Communications,1991,vol. 21,p. 2391 - 2396.

43
[ 124755-24-4 ]
(2E,8Z,13Z,21Z)-(4R,5R,10S,11S,12S,17R,18S,19S,20S)-19-(tert-Butyl-dimethyl-silanyloxy)-5,11,17-tris-(4-methoxy-benzyloxy)-4,10,12,18,20-pentamethyl-tetracosa-2,8,13,21,23-pentaenal [ No CAS ]
[ 479673-34-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -79℃; for 6h;	The above alcohol (47 mg, [49] [JUMOL)] in [CH2C12] (2 mL) was treated with Dess- Martin periodinane (31 mg, [73] [CYMOL).] After 2 h, the mixture was quenched with saturated [NAHC03] (5 mL). The aqueous layer was extracted with ethyl ether (5 mL x 2) and the combined extracts were dried over anhydrous [MGS04.] Filtration and concentration followed by short flash column chromatography filtration (hexane/EtOAc 3: 1) to remove the residue from Dess-Martin reagent provided crude aldehyde as a colorless oil which was used for the next reaction without further purification. To a stirred solution of bis (2,2, 2-trifluoroethyl) - (methoxycarbonylmethyl) phosphate (0.013 ml, [59] [MOL),] 18-crown-6 (0.065 g, 0.25 mmol) in THF (1 ml) cooled to-78 °C was added dropwise potassium bis (trimethylsilyl) amide (0.12 ml, [59 AMOL, 0. 5M] solution in toluene). Thereafter the above aldehyde in THF (1 ml) was added and the solution was stirred for 6 h [AT-78 °C.] The reaction mixture was quenched by addition of a sat'd [NH4C1] solution [(1] ml) and diluted with diethyl ether (10 ml). The layer was separated and organic phase was washed with brine (10 ml) and dried with [MGS04,] filtered, and concentrated. The residue was purified by flash chromatography (EtOAc/Hexane 1: 5), yielding 40 mg of [(E, Z)-DOUBLY] unsaturated ester 53 (85percent for 2 steps): IR [(CHC13)] 2956,2856, 1717,1612, 1513,1462, 1301,1248, 1173,1037, 820 [CMAPOS;] [; 1H NMR (300 MHZ,] CDC13) [8] 7.53 (dd, [J=] 15.4, 11.3 Hz, 1H), 7.43-7. 37 [(M,] 6H), 7.03-6. 98 [(M,] 6H), 6.68 (dd, J [= 11.] 4,11. 3 Hz, [1H),] 6. [53] (ddd, [J=] 17.0, 10.7, 10.4 Hz, [1H),] 6.19 (dd, [J=] 15.4, 7.6 Hz, [1H),] 6.09 (apparent t, J= 11.2 Hz, 1H), 5.73 (d, J= 11.4 Hz, 1H), 5.64 (d, J= 10.3 Hz, 1H), 5.56 (d, J= 11.0 Hz, 1H), 5.45-5. 41 [(M,] 3H), 5.28 (d, J= 15.3 Hz, 1H), 5. [18] (d, J= 10.0 Hz, 1H), 4.71-4. 45 [(M,] 6H), 3.94 (s, 6H), 3.93 (s, 3H), 3.87 (s, 3H), 3.70 (dd, J= 6.1, 3.2 Hz, 1H), 3.44-3. [38] [(M,] 1H), 3.19 (dd, J= 6.9, 4.2 Hz, 1H), 2. [85-2.] 77 [(M,] 3H), 2.34-2. 31 [(M,] 2H), 2.08-2. 04 [(M,] 3H), 1.84-1. 55 [(M,] [5H),] 1.20 (d, J= 6.8 Hz, 3H), 1.14 (d, J= 6.9 Hz, 3H), 1.12 (d, J= 8.2 Hz, 3H), 1.07-1. 01 [(M,] 15H), 0.16 (s, 6H); [13C] NMR (75 MHz, CDC13) [8] 166.9, 159.1, 158.9, 147.6, 145.6, 134.7, 133.7, 132.7, 132.4, 131.3, 130.9, 130.8, 129.5, 129.4, 129.0, 128.9, 128.4, 126.4, 117.2, 115.4, 113.7, 87.9, 82.1, 78. 8,74. 7,71. 4,70. 8,55. 2,53. 4, 51.1, 40.0, 36.4, 35.4, 35.2, 31.4, 31.3, 29.7, 26.2, 23.7, 23.6, 18.9, 18.6, 18. 5,17. 1,15. 4, 10.9,-3. 3, -3.4 ; LRMS (API-ES) 1045.5 (M+K) +, 1029.5 (M+Na) [+] ; [[A]] [20D] +35.3 (c 0.96, [CHC13)]

References: [1]Patent: WO2004/22552,2004,A1 .Location in patent: Page 60.

44
C₂₃H₄₁IO₂Si [ No CAS ]
[ 124755-24-4 ]
C₂₇H₄₇IO₃Si [ No CAS ]

References: [1]Synlett,2006,p. 2649 - 2651.

45
[ 124755-24-4 ]
[ 107-02-8 ]
[ 25522-27-4 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 6610 - 6615.

46
C₆₄H₁₁₀O₈Si₃ [ No CAS ]
[ 124755-24-4 ]
[ 672296-53-6 ]

Yield	Reaction Conditions	Operation in experiment
82%		7 (S), 9 (S), [19-TRIS-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-13 (R),] 21 [(S)-BIS- (4-] methoxy-benzyloxy)-6 (R), 12 [(S),] 14 [(S),] 16 [(5),] 20 [(R),] 22 [(S)-HEXAMETHYL-HEXACOSA-] 2,4, 10,23, 25-pentaenoic acid methyl ester (79). A solution of 77 (18.6 mg) in CH2C12 (0.2 ml) was cooled to-78 °C and B-chlorocatecholborane (0.25 M in [CH2CL2,] 0.17 ml) was added. The solution was stirred at-78 °C for 1 h followed by treatment with sat'd aqueous [NAHC03] (1 ml). The resulting reaction mixture was then diluted with [CH2CL2] (10 ml) and [H20] (3 ml). The layers were separated and the aqueous layer was further extracted with [CH2C12] (2 x 5 ml). The combined organic layers were washed with brine, dried over MgS04 and concentrated under vacuum. The residue was purified by flash chromatography [(HEXANE/ETOAC] 4; 1) on silica gel to yield [78] (9.4 mg) as a colorless oil. The alcohol 78 (20 mg, 0. [018] [UMOL)] in [CH2CL2] (0.5 mL) was treated with Dess-Martin periodinane (12 mg, 0. [028] mol). After [1] h, the mixture was quenched with saturated [NAHC03] [(1] ml). The aqueous layer was extracted with ethyl ether (3 ml x 2) and the combined extracts were dried over anhydrous MgS04. Filtration and concentration followed by short flash column chromatography filtration (hexane/EtOAc 4.5 : 1) to remove the residue from Dess-Martin reagent provided crude aldehyde as a colorless oil which was used for the next reaction without further purification. To a stirred solution of bis (2,2, 2-trifluoroethyl) - (methoxycarbonylmethyl) phosphate (0.005 ml, 0.024 [CYMOL),] 18-crown-6 (0.024 g, 0.09 mmol) in THF (0.5 ml) cooled to-78 °C was added dropwise potassium bis (trimethylsilyl) amide (0.044 ml, 0.022 [DMOL,] [0.] 5M solution in toluene). Thereafter the above aldehyde in THF (0.5 ml) was added and the solution was stirred for 6 h at-78 [°C.] The reaction mixture was quenched by addition of a sat'd [NH4C1] solution (1 ml) and diluted with diethyl ether (5 ml). The layers were separated and organic phase was washed with brine (5 ml) and dried with [MGS04,] filtered, and concentrated. The residue was purified by flash chromatography (EtOAc/Hexane 1: 9) yielding 17 mg of [(E, Z)-DOUBLY] unsaturated ester 79 (82 percent for 2 steps): IR [(CHC13)] 2956,2929, [2856,] 1720,1613, 1514,1462, 1249,1173, 1075, 836,773 [CM-1] [; 1H] NMR (300 MHz, [CDC13)] [5] 7.22 [(M,] [5H),] 6. 82 [(M,] 4H), 6.55 (ddd, [J= 16. 8,] 10.8, 10. [8] Hz, 1H), 6. [38] (t, J= 11.4 Hz, 1H), 6.05 (dd, J= 15.4, 6.2 Hz, 1H), 5.98 (t, [J= 11.] 0 Hz, [1H),] 5. [55] (t, [J=] 10.5 Hz, [1H),] 5.48 (d, [J=] 11.5 Hz, [1H),] 5.31 [(M,] 2H), 5.14 (d, [J=] 16. [8] Hz, 1H), 5.05 (d, [J =] 10.1 Hz, 1H), 4.54 [(M,] 1H), 4.49 [(M,] 3H), 4.31 (d, [J =] 10.9 Hz, 1H), 3. 87 [(M,] 1H), 3.77 (s, 3H), 3.75 (s, 3H), 3.68 (s, 3H), 3.57 [(M,] 1H), 3.29 (dd, J= 7.7, 3.1 Hz, 1H), 2.94 [(M,] 2H), 2.68 [(M,] 1H), 2.48 [(M,] 1H), 1.65 [(M,] 3H), 1. [43-1.] 28 [(M,] 6H), 1.20 [(M,] 2H), 1.08 (d, J= 6.8 Hz, 3H), 0.96 (d, J= 6.9 Hz, 3H), 0.94 (d, J= 6.1 Hz, 3H), 0.90 (s, 9H), 0.86 [(M,] 21H), 0.81 (d, J= 6.7 Hz, 3H), 0.71 (d, J= 6.4 Hz, 3H), 0.06 (s, 3H), 0.05 (s, 3H), 0.04 (s, 3H), 0.02 (s, 6H) [; 13C NMR] (75 MHz, [CDC13)] [8] 166.9, 159.0, 158.8, 147.7, 146.9, 145. 8, 134.6, 133.5, 132.7, 132.5, 131.6, 131.4, 129.1, 128.9, 128. 8,128. 7,128. 4,127. 9, 127.7, 127.3, 126.4, 117.2, 114.9, 113.7, 113.6, 87.6, 84.3, 77.2, 74.9, 74.2, 72.9, 72.7, 66.4, 55.3, 55.2, 50.9, 43.1, 42.5, 42.1, 40.6, 35.8, 35.3, 33.6, 33.2, 32.9, 18.14, 18. 11,14. 6,13. 9, 9.3,-2. 9, -3.6,-3. 9, -4.1,-4. 4; HRMS [(ESI)] calcd for [C67HLL4O9SI3K] 1185.7408 [(M+K) +,] found [1185.] 7464; [[OC] 2°D-12.] 6 (c 0.75, [CHC13).]

References: [1]Patent: WO2004/22552,2004,A1 .Location in patent: Page 75-77.

47
[ 1092490-80-6 ]
[ 124755-24-4 ]
[ 1092490-81-7 ]
C₃₀H₄₂O₅Si [ No CAS ]

References: [1]Synlett,2008,p. 2459 - 2460.

48
C₂₈H₃₅NO₄ [ No CAS ]
[ 124755-24-4 ]
[ 1078789-79-3 ]

References: [1]Organic Letters,2008,vol. 10,p. 5031 - 5033.
[2]Chemistry - A European Journal,2011,vol. 17,p. 14593 - 14602.

49
[ 124755-24-4 ]
[ 87938-77-0 ]
C₁₅H₁₇BrO₄ [ No CAS ]

References: [1]Heterocycles,2009,vol. 77,p. 201 - 206.

50
[ 960409-30-7 ]
[ 124755-24-4 ]
[ 960409-32-9 ]

Yield	Reaction Conditions	Operation in experiment
81%		In a three-necked round bottom flask, sodium hydride 60percent (1.04 g, 26.0 mmol) was suspended in dimethoxyethane (15 mL) at 0° C. Ethyl[bis(2,2,2-trifluoroethoxy)phosphinyl] acetate (8.63 g, 26.0 mmol) was added and the mixture was stirred at room temperature for 15 minutes. A solution of 1-{3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]phenyl}ethanone (6.60 g, 17.3 mmol) and dimethoxyethane (20 mL) was added and the mixture was brought to reflux and stirred for 1 hr. The reaction mixture was hydrolyzed with saturated aqueous ammonium chloride (80 mL). The aqueous layer was extracted with ethyl acetate (3.x.100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2) to yield 7.5 g (81percent) of the desired product as a colorless oil of a mixture of E and Z isomers.

References: [1]Patent: US2009/203696,2009,A1 .Location in patent: Page/Page column 24.

51
[ 57978-00-4 ]
[ 124755-24-4 ]
[ 1193752-55-4 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 16016 - 16017.
[2]Journal of the American Chemical Society,2010,vol. 132,p. 427 - 427.

52
[ 124755-24-4 ]
[ 147513-32-4 ]
(Z)-ethyl 3-[(2S,3S)-3-heptyloxiran-2-yl]acrylate [ No CAS ]
[ 158391-41-4 ]

References: [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 3950 - 3953.

53
(2E,4Z)-2,4-undecadienal [ No CAS ]
[ 124755-24-4 ]
[ 1325759-05-4 ]

References: [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 11344 - 11349.

54
[ 123-73-9 ]
[ 124755-24-4 ]
[ 53282-25-0 ]

References: [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 11344 - 11349.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

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CAS No.: 124755-24-4

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CAS No.: 124755-24-4

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