[ CAS No. 85920-63-4 ] {[proInfo.proName]}

Name: 85920-63-4|5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione|97%
Brand: Ambeed
SKU: A418477
Price: 7.0 USD
Availability: InStock
Rating: 93 (22 reviews)

,{[proInfo.pro_purity]}

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

DV 2D 3D

3d Animation Molecule Structure of 85920-63-4

Structure of 85920-63-4 * 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 [ 85920-63-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 85920-63-4 ]

SDS Specification

Alternatived Products of [ 85920-63-4 ]

Product Details of [ 85920-63-4 ]

CAS No. :	85920-63-4	MDL No. :	MFCD18072503
Formula :	C₈H₁₀O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WIIDJHLROTYVRD-UHFFFAOYSA-N
M.W :	186.16	Pubchem ID :	54693142
Synonyms :

Calculated chemistry of [ 85920-63-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	0
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.16
TPSA :	72.83 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) :	-6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.65
Log Po/w (XLOGP3) :	1.48
Log Po/w (WLOGP) :	0.65
Log Po/w (MLOGP) :	0.02
Log Po/w (SILICOS-IT) :	0.79
Consensus Log Po/w :	0.92

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.93
Solubility :	2.2 mg/ml ; 0.0118 mol/l
Class :	Very soluble
Log S (Ali) :	-2.62
Solubility :	0.45 mg/ml ; 0.00242 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.85
Solubility :	26.0 mg/ml ; 0.14 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	4.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.75

Safety of [ 85920-63-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 85920-63-4 ]

* 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 [ 85920-63-4 ]
Downstream synthetic route of [ 85920-63-4 ]

[ 85920-63-4 ] Synthesis Path-Upstream 1~4

1
[ 2033-24-1 ]
[ 75-36-5 ]
[ 85920-63-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: With pyridine In dichloromethane at 0℃; for 0.25 h; Stage #2: at 0 - 20℃; for 3 h;	General procedure: Method A: Adapted from the procedure of Srensen et al.¹⁴ To a solution of Meldrum’s acid (1equiv) in dichloromethane at 0°C was added pyridine (2equiv) drop wise, and the resulting solution was stirred for 15min. The corresponding acid chloride (1equiv) was added to this reaction mixture. Thereafter, the reaction was stirred for 1.5h at 0°C, and for an additional 1.5h at room temperature. The reaction was quenched with 2M hydrochloric acid, and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography using a gradient from 5percent to 10percent ethyl acetate in hexane, 1percent acetic acid to yield acyl Meldrum’s acids (11a–e, j, l, p).
7.44 g	Stage #1: With pyridine In dichloromethane at -5℃; for 0.166667 h; Stage #2: at 20℃; for 1.33333 h;	Meldrum's acid (7.2g, 0.05M) and was dissolved in dichloromethane (60mL), was added pyridine inner temperature as -5°C (7.9g, 0.1M) and slowly mixed and stirred for about 10 minutes to obtain a liquid.Then, to the resulting mixture was added dropwise acetyl chloride (4.3g, 0.055M) in dichloromethane (20mL) solution of over 20 minutes. Thereafter, the resulting solution was reacted at room temperature for 1 hour, the reaction mixture was acidified with 1N-HCl, washed with water, after performing drying over MgSO_4,evaporated, red-brown oil was obtained.The oil was repeated twice purified by silica gel chromatography (Hexane: AcOEt = 10: 1 ~ 5: 1), to give 7.44g of compound A.

Reference： [1] Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1003 - 1007
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 6, p. 1321 - 1340
[3] Acta Chimica Slovenica, 2013, vol. 60, # 2, p. 403 - 410
[4] Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1427 - 1445
[5] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 10, p. 1303 - 1306
[6] Tetrahedron Letters, 1998, vol. 39, # 41, p. 7487 - 7490
[7] Chemical Communications, 1999, # 12, p. 1113 - 1114
[8] European Journal of Organic Chemistry, 2003, # 3, p. 537 - 541
[9] Synthetic Communications, 2005, vol. 35, # 16, p. 2139 - 2141
[10] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 365 - 369
[11] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 12, p. 3203 - 3214
[12] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 20, p. 9349 - 9358
[13] Tetrahedron Letters, 2010, vol. 51, # 3, p. 548 - 549
[14] Tetrahedron, 2011, vol. 67, # 17, p. 3062 - 3070
[15] Patent: KR2015/43489, 2015, A, . Location in patent: Paragraph 0278-0280; 0283
[16] Organic Syntheses, 2000, vol. 77, p. 114 - 114

2
[ 2033-24-1 ]
[ 78-39-7 ]
[ 85920-63-4 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 365 - 369

3
[ 2033-24-1 ]
[ 64-19-7 ]
[ 85920-63-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 10, p. 3117 - 3121
[2] Journal of the American Chemical Society, 2012, vol. 134, # 4, p. 1962 - 1965

4
[ 112182-59-9 ]
[ 85920-63-4 ]

Reference： [1] Journal of Organic Chemistry, 2006, vol. 71, # 13, p. 4795 - 4802
[2] Journal of Organic Chemistry, 2006, vol. 71, # 13, p. 4795 - 4802

[ 85920-63-4 ] Synthesis Path-Downstream 1~88

1
[ 1452-77-3 ]
[ 85920-63-4 ]
[ 82437-55-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 3505 - 3512

2
[ 2033-24-1 ]
[ 75-36-5 ]
[ 85920-63-4 ]

Yield	Reaction Conditions	Operation in experiment
83%		General procedure: Method A: Adapted from the procedure of Srensen et al.14 To a solution of Meldrum?s acid (1equiv) in dichloromethane at 0C was added pyridine (2equiv) drop wise, and the resulting solution was stirred for 15min. The corresponding acid chloride (1equiv) was added to this reaction mixture. Thereafter, the reaction was stirred for 1.5h at 0C, and for an additional 1.5h at room temperature. The reaction was quenched with 2M hydrochloric acid, and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography using a gradient from 5% to 10% ethyl acetate in hexane, 1% acetic acid to yield acyl Meldrum?s acids (11a-e, j, l, p).
	With pyridine; In dichloromethane; at 0 - 20℃; for 15h;	General procedure: Pyridine (2 equiv) was added to a solution of Meldrum?s acid (1 equiv) in DCM (0.7 M). The acyl chloride (1 equiv) was dissolved in DCM (1.4 M) and was added dropwise to the Meldrum?s acid solution at 0 C. The reaction was stirred for 1.5 h at 0 C and 1.5 h at room temperature. An additional portion acyl chloride (0.5 equiv) was added and stirring was continued for 12 h at room temperature. Then the reaction was stopped by adding HCl (2 M) and diluted with DCM. The organic phase was separated, dried over Na2SO4 and evaporated. The crude product was either purified by column chromatography or crystallized to yield the pure acyl Meldrum?s acid.
7.44 g		Meldrum's acid (7.2g, 0.05M) and was dissolved in dichloromethane (60mL), was added pyridine inner temperature as -5C (7.9g, 0.1M) and slowly mixed and stirred for about 10 minutes to obtain a liquid.Then, to the resulting mixture was added dropwise acetyl chloride (4.3g, 0.055M) in dichloromethane (20mL) solution of over 20 minutes. Thereafter, the resulting solution was reacted at room temperature for 1 hour, the reaction mixture was acidified with 1N-HCl, washed with water, after performing drying over MgSO4,evaporated, red-brown oil was obtained.The oil was repeated twice purified by silica gel chromatography (Hexane: AcOEt = 10: 1 ~ 5: 1), to give 7.44g of compound A.

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 12446 - 12450
Angew. Chem.,2019,vol. 131,p. 12576 - 12580,5
[2]Journal of Organic Chemistry,2000,vol. 65,p. 1003 - 1007
[3]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 1321 - 1340
[4]Acta Chimica Slovenica,2013,vol. 60,p. 403 - 410
[5]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445
[6]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1303 - 1306
[7]Tetrahedron Letters,1998,vol. 39,p. 7487 - 7490
[8]Chemical Communications,1999,p. 1113 - 1114
[9]European Journal of Organic Chemistry,2003,p. 537 - 541
[10]Synthetic Communications,2005,vol. 35,p. 2139 - 2141
[11]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 365 - 369
[12]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3203 - 3214
[13]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9349 - 9358
[14]Tetrahedron Letters,2010,vol. 51,p. 548 - 549
[15]Tetrahedron,2011,vol. 67,p. 3062 - 3070
[16]Patent: KR2015/43489,2015,A .Location in patent: Paragraph 0278-0280; 0283
[17]Organic Syntheses,2000,vol. 77,p. 114 - 114

3
[ 10160-24-4 ]
[ 85920-63-4 ]
[ 85920-66-7 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 253 - 256
[2]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

4
[ 85920-63-4 ]
[ 928-51-8 ]
[ 91116-20-0 ]

Reference： [1]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

5
[ 85920-63-4 ]
[ 34626-51-2 ]
[ 85920-64-5 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 253 - 256
[2]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

6
[ 85920-63-4 ]
[ 4286-55-9 ]
[ 85920-65-6 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 253 - 256
[2]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

7
[ 85920-63-4 ]
[ 55362-80-6 ]
[ 85920-68-9 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 253 - 256
[2]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

8
[ 85920-63-4 ]
[ 53463-68-6 ]
[ 85920-69-0 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 253 - 256
[2]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

9
[ 85920-63-4 ]
[ 1611-56-9 ]
[ 85920-70-3 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 253 - 256
[2]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

10
[ 85920-63-4 ]
[ 50816-19-8 ]
[ 85920-67-8 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 253 - 256
[2]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

11
[ 85920-63-4 ]
[ 22835-64-9 ]
[ 77060-85-6 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 1987 - 1990

12
[ 85920-63-4 ]
[ 2699-89-0 ]
[ 77060-84-5 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 1987 - 1990

13
[ 85920-63-4 ]
[ 60078-92-4 ]
[ 118798-09-7 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 1539 - 1543

14
[ 85920-63-4 ]
[ 91029-31-1 ]
[ 118798-08-6 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 1539 - 1543

15
[ 85920-63-4 ]
[ 18804-33-6 ]
(6'-Chloro-2'-hexyl)-3-oxobutanoate [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

16
[ 85920-63-4 ]
[ 85920-77-0 ]
[ 85920-79-2 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 253 - 256
[2]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

17
[ 85920-63-4 ]
[ 118798-06-4 ]
[ 118798-07-5 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 1539 - 1543

18
[ 85920-63-4 ]
[ 145122-75-4 ]
[ 145122-77-6 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 253 - 256
[2]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

19
[ 85920-63-4 ]
[ 145122-76-5 ]
[ 145122-78-7 ]

Reference： [1]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445
[2]Tetrahedron Letters,1983,vol. 24,p. 253 - 256

20
[ 85920-63-4 ]
[ 84447-15-4 ]
[ 27991-08-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 3097 - 3105

21
[ 85920-63-4 ]
[ 1453-82-3 ]
[ 82437-57-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 3505 - 3512

22
[ 85920-63-4 ]
[ 98-92-0 ]
[ 82437-56-7 ]

Reference： [1]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 3505 - 3512

23
[ 85920-63-4 ]
[ 107-18-6 ]
[ 1118-84-9 ]

Reference： [1]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445
[2]European Journal of Organic Chemistry,2003,p. 537 - 541

24
[ 85920-63-4 ]
[ 538-75-0 ]
[ 93598-46-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2602 - 2608

25
[ 85920-63-4 ]
[ 540-51-2 ]
[ 88488-47-5 ]

Reference： [1]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

26
[ 85920-63-4 ]
[ 627-18-9 ]
[ 88593-98-0 ]

Reference： [1]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

27
[ 85920-63-4 ]
[ 691-45-2 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 1686 - 1695

28
[ 85920-63-4 ]
[ 582-52-5 ]
[ 66888-11-7 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 3427 - 3434
[2]Journal of Organic Chemistry,1995,vol. 60,p. 7879 - 7883

29
[ 110-87-2 ]
[ 85920-63-4 ]
3-[1-Hydroxy-eth-(E)-ylidene]-tetrahydro-pyrano[2,3-b]pyran-2,4-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 6499 - 6502

30
[ 111-34-2 ]
[ 85920-63-4 ]
6-Butoxy-3-[1-hydroxy-eth-(E)-ylidene]-dihydro-pyran-2,4-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 6499 - 6502
[2]Tetrahedron Letters,1998,vol. 39,p. 7487 - 7490

31
[ 85920-63-4 ]
[ 928-55-2 ]
6-Ethoxy-3-[1-hydroxy-eth-(E)-ylidene]-5-methyl-dihydro-pyran-2,4-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 6499 - 6502

32
[ 85920-63-4 ]
[ 926-02-3 ]
6-tert-Butoxy-3-[1-hydroxy-eth-(E)-ylidene]-dihydro-pyran-2,4-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 6499 - 6502

33
[ 85920-63-4 ]
[ 5848-33-9 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 6499 - 6502

34
[ 85920-63-4 ]
[ 75-03-6 ]
[ 100-63-0 ]
[ 22717-41-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1303 - 1306

35
[ 85920-63-4 ]
[ 638-45-9 ]
[ 100-63-0 ]
[ 192209-26-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1303 - 1306

36
[ 85920-63-4 ]
[ 105-36-2 ]
[ 100-63-0 ]
[ 24246-11-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1303 - 1306

37
[ 85920-63-4 ]
[ 4333-56-6 ]
[ 100-63-0 ]
4-cyclopropyl-3-methyl-1-phenyl-5-pyrazolone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1303 - 1306

38
[ 85920-63-4 ]
[ 3815-09-6 ]
[ 100-63-0 ]
4-(2,2-Dimethyl-cyclopropyl)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1303 - 1306

39
[ 2033-24-1 ]
[ 78-39-7 ]
[ 85920-63-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 365 - 369

40
[ 4721-98-6 ]
[ 85920-63-4 ]
9,10-dimethoxy-2-methyl-6,7-dihydro-4H-pyrido[2,1-a]isoquinolin-4-one [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 935 - 938

41
[ 85920-63-4 ]
[ 525-41-7 ]
6,7-dihydro-2-methyl-indolo[2,3-a]quinolizin-4-one [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 935 - 938

42
[ 85920-63-4 ]
[ 72345-23-4 ]
[ 736177-39-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3203 - 3214

43
[ 112182-59-9 ]
[ 85920-63-4 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 4795 - 4802
[2]Journal of Organic Chemistry,2006,vol. 71,p. 4795 - 4802

44
[ 85920-63-4 ]
[ 1068658-13-8 ]
[ 35219-19-3 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 9368 - 9376

45
[ 85920-63-4 ]
[ 1068658-15-0 ]
[ 35219-19-3 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 9368 - 9376

46
[ 85920-63-4 ]
C₂₁H₃₄NO₃PolSi [ No CAS ]
C₂₅H₃₈NO₅PolSi [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 3117 - 3121

47
[ 2033-24-1 ]
[ 64-19-7 ]
[ 85920-63-4 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 16h;Inert atmosphere;	General procedure: Freshly recrystallized Meldrum?s acid 1 (1.0 g, 6.9 mmol) and benzoic acid 3a (0.85 g, 6.9 mmol) were dissolved in dry CH2Cl2 (10 mL) and stirred at room temperature for 5 minutes. DMAP (1.7 g, 13.9 mmol) followed by DCC (2.0 g, 9.7 mmol) were added to the reaction mixture and the mixture was stirred for 16 h under nitrogen. It was noted colourless reaction mixture turned to brown over a period of time. After the complete consumption of Meldrum?s acid 1 (monitored by TLC) solution was quenched with 1 M HCl (10 mL). The reaction was filter through a sintered funnel over celite. The organic layer was collected and washed with 1 M HCl (10 mL X 3) followed by with brine and dried over anhydrous Na2SO4. The solvent was removed in vacuo. A crude product 4a (95% yield, 1.64 g) was used immediately without any purification (compound 4a slowly undergoes hydrolysis and decarboxylation to give acetophenone 4a?). Likewise, compounds 4b-4i were prepared following the similar general procedure. The compound 4j (55% yield, 0.66 g) was prepared following the literature procedure.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 3117 - 3121
[2]Journal of the American Chemical Society,2012,vol. 134,p. 1962 - 1965
[3]Tetrahedron Letters,2019,vol. 60,p. 197 - 200

48
[ 85920-63-4 ]
C₄H₈NO₂Pol [ No CAS ]
C₈H₁₂NO₄Pol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 7240 - 7245
Angewandte Chemie,2009,vol. 121,p. 7376 - 7381

49
[ 85920-63-4 ]
C₅H₁₀NO₂Pol [ No CAS ]
C₉H₁₄NO₄Pol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 7240 - 7245
Angewandte Chemie,2009,vol. 121,p. 7376 - 7381

50
[ 85920-63-4 ]
C₁₁H₁₄NO₃Pol [ No CAS ]
C₁₅H₁₈NO₅Pol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 7240 - 7245
Angewandte Chemie,2009,vol. 121,p. 7376 - 7381

51
[ 85920-63-4 ]
C₁₂H₁₆NO₄Pol [ No CAS ]
C₁₆H₂₀NO₆Pol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 7240 - 7245
Angewandte Chemie,2009,vol. 121,p. 7376 - 7381

52
[ 85920-63-4 ]
C₁₃H₂₄NO₂Pol [ No CAS ]
C₁₇H₂₈NO₄Pol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 7240 - 7245
Angewandte Chemie,2009,vol. 121,p. 7376 - 7381

53
[ 85920-63-4 ]
C₁₃H₁₈NO₂Pol [ No CAS ]
C₁₇H₂₂NO₄Pol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 7240 - 7245
Angewandte Chemie,2009,vol. 121,p. 7376 - 7381

54
[ 85920-63-4 ]
[ 623-33-6 ]
[ 1254960-13-8 ]

Reference： [1]Journal of Molecular Structure,2010,vol. 976,p. 377 - 391

55
[ 85920-63-4 ]
[ 3182-93-2 ]
[ 1254960-21-8 ]

Reference： [1]Journal of Molecular Structure,2010,vol. 976,p. 377 - 391

56
[ 85920-63-4 ]
[ 3417-91-2 ]
[ 1254960-24-1 ]

Reference： [1]Journal of Molecular Structure,2010,vol. 976,p. 377 - 391

57
[ 5813-89-8 ]
[ 85920-63-4 ]
[ 1207108-25-5 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 548 - 549

58
[ 541-35-5 ]
[ 85920-63-4 ]
[ 77656-05-4 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 548 - 549

59
[ 85920-63-4 ]
[ 626-97-1 ]
[ 84449-27-4 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 548 - 549

60
[ 85920-63-4 ]
[ 55-21-0 ]
[ 3283-23-6 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 548 - 549

61
[ 85920-63-4 ]
[ 609-66-5 ]
[ 84449-22-9 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 548 - 549

62
[ 85920-63-4 ]
(9S,9aR)-7,7-dimethyl-2-(toluene-4-sulfonyl)-2,6a,7,8,9,9a-hexahydro-6H-isoindolo[4,5,6-cd]indole-9-carboxylic acid ethyl ester [ No CAS ]
C₂₇H₂₆N₂O₅S [ No CAS ]
C₂₇H₂₆N₂O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Acetyl-Meldrum?s acid (309 mg, 1.66 mmol) was added to a solution of the denosylated precursor from the preceding reaction (300 mg, 663 mumol) in dioxane (15 mL). The reaction was stirred for 90 min at 80 C. Then a solution of KOH in MeOH (0.1 M, 16.6 mL, 1.66 mmol) was added and stirring was continued for another 60 min at 80 C. The solvent was removed under reduced pressure and the residue separated between DCM and aqueous ammonium chloride. The aqueous phase was extracted twice with DCM and the combined organic layers were dried over Na2SO4. Filtration and evaporation of the solvent under reduced pressure gave a crude product (347 mg), which yielded 16 (260, 80%) as a 1:1 mixture of diastereomers after chromatographic purification (DCM/MeOH 25/1). The diastereomers of a small sample were separated by semipreparative HPLC (ACN/H2O 70/30). Rf (DCM/MeOH 95/5): 0.45. (6aR,11aS,11bR)-N-tosyl-CPA 16a (cis-C/D ring connection): 1H NMR (600 MHz; CDCl3): delta=7.85 (d, J=8.4 Hz, 2H), 7.78 (d, J=8.3 Hz, 1H), 7.55 (s, 1H), 7.30-7.27 (m, 1H), 7.25 (d, J=8.2 Hz, 2H), 7.05 (d, J=7.3 Hz, 1H), 4.00 (d, J=10.9 Hz, 1H), 3.58 (dd, J=10.9, 6.0 Hz, 1H), 3.02 (dd, J=16.3, 5.8 Hz, 1H), 2.94 (dd, J=16.1, 11.7 Hz, 1H), 2.59 (Psidt, J=11.6, 5.9, 5.9 Hz, 1H), 2.49 (s, 3H), 2.36 (s, 3H), 1.67 (s, 3H), 1.58 (s, 3H); 13C NMR (125 MHz; CDCl3): delta=194.3, 185.0, 175.4, 144.7, 135.6, 133.1, 129.8 (CH), 129.3, 128.4, 126.9 (CH), 125.5 (CH), 122.9 (CH), 120.6 (CH), 116.2, 111.6 (CH), 105.4, 70.7 (CH), 63.6, 52.4 (CH), 35.4 (CH), 26.1 (CH3), 26.1 (CH2), 24.4 (CH3), 21.5 (CH3), 19.8 (CH3); HR-ES-MS: m/z=513.1449 (calcd 513.1455 for C27H26N2NaO5S); IR: nu=3415, 1709, 1614 cm-1. (6aS,11aS,11bR)-N-Tosyl-CPA 16b (trans-C/D ring connection): 1H NMR (600 MHz; CDCl3): delta=7.85 (d, J=8.4 Hz, 2H), 7.82 (d, J=8.2 Hz, 1H), 7.55 (d, J=1.7 Hz, 1H), 7.29 (Psit, J=7.8 Hz, 1H), 7.25 (d, J=8.1 Hz, 2H), 7.06 (d, J=7.3 Hz, 1H), 4.09 (d, J=10.7 Hz, 1H), 2.95 (Psidt, J=11.4, 1.7 Hz, 1H), 2.92 (dd, J=15.6, 4.6 Hz, 1H), 2.88 (dd, J=15.5, 11.8 Hz, 1H), 2.52 (s, 3H), 2.37 (s, 3H), 2.32, (Psidt, J=11.8, 11.8, 4.6 Hz, 1H), 1.60 (s, 3H), 1.53 (s, 3H); 13C NMR (125 MHz; CDCl3): delta=193.6, 185.6, 174.6, 144.7, 135.7, 133.7, 130.9 (CH), 129.9, 129.4, 126.9 (CH), 125.6 (CH), 121.3 (CH), 121.2 (CH), 118.0, 111.9 (CH), 105.3, 71.2 (CH), 62.1, 58.0 (CH), 38.4 (CH), 28.0 (CH3), 27.2 (CH2), 21.5 (CH3), 19.8 (CH3), 19.7 (CH3); HR-ES-MS: m/z=489.1497 (calcd 489.1490 for C27H25N2O5S); IR: nu=3362, 1611 cm-1.

Reference： [1]Tetrahedron,2011,vol. 67,p. 3062 - 3070

63
[ 85920-63-4 ]
[ 762-42-5 ]
[ 603-35-0 ]
[ 1265596-23-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	In dichloromethane; at 20℃; for 1h;	To a magnetically stirred solution of acetyl meldrum's acid (0.18 g, 1 mmol) and triphenylphosphine (0.26 g, 1 mmol) in CH2CI2 (10 mL) a mixture of dimethylacetylenedicarboxylate (0.12 mL, 1 mmol) in CH2CI2 (5 mL) was added drop wise at room temperature and the mixture was allowed to stirred for 1 h. The solvent was removed under reduced pressure and ylide (4) (0.57 g, m.p. (decompose) 137 C, yield 97%) was obtained as an orange powder.

Reference： [1]Journal of Molecular Structure,2011,vol. 985,p. 120 - 127
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2012,vol. 187,p. 1109 - 1117

64
[ 85920-63-4 ]
[ 1313424-83-7 ]
[ 1313424-94-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In 1,2-dichloro-ethane; at 140℃; for 0.0333333h;Microwave irradiation;	In an adaptation of GP 7a: At room temperature 1 ,2-dichloroethane (2 mL), pre-saturated with hydrochloric acid (g), was added to the solution of 2-phenethyl-4,5-dihydro-thiazole-4- carboxylic acid methyl ester (intermediate E.1 ) (446 mg, 1 .79 mmol) and commercially available Acetyl-Meldrum's acid (1 g, 5 mmol, 3.0 eq.) in 1 ,2-dichloroethane (13 mL). The reaction mixture was heated to 140C for 120 seconds in a Biotage Initiator microwave oven. TLC analysis showed complete turnover. After removal of the solvent the target compound was isolated by filtration of the crude product over a pad of silica gel followed by flash column chromatography (yield: 500 mg).1H-NMR (CDCIs, 300 MHz): 2.03 (d, 3H); AB-Signal (deltaAlpha = 3.54, deltaBeta = 3.74, 2 x 1 H); 3.75 (s, 2H); 3.82 (s, 3H); 5.66 (dd, 1 H); 6.18 (d, 1 H); 7.09 - 7.15 (m, 2H); 7.17 - 7.24 (m, 1 H); 7.26 - 7.32 (m, 2H).MS (EI+): M+ = 315

Reference： [1]Patent: WO2011/76687,2011,A1 .Location in patent: Page/Page column 135

65
[ 85920-63-4 ]
[ 1313424-92-8 ]
[ 1313425-02-3 ]

Yield	Reaction Conditions	Operation in experiment
		In an adaptation of general procedure 29b: Acetyl meldrum's acid (27.4 g, 147 mmol, 3 eq.) and 2-[2-(2-fluoro-6-trifluoromethyl-phenyl)-ethyl]-4,5-dihydro-oxazole-4-carboxyl i c aci d methyl ester (intermediate E.8) (15.6 g, 49.0 mmol) in toluene (300 mL) were heated to reflux for 20 min. Then trifluoro acetic acid (18.9 mL, 27.9 g, 245 mmol, 5 eq.) was added and reflux was continued for 1 hour. The reaction mixture was partitioned between water and ethyl acetate. After phase separation, extraction of the aqueous layer with ethyl acetate, washing of the combined organic layers with brine and evaporation of the solvent flash chromatography yielded the desired title compound (yield: 4.7 g)1H-NMR (methanol-d4, 300 MHz): 3.77 (s, 3H); 3.99 (s, 2H); 4.64 (dd, 1 H); 4.75 (t, 1 H); 5.23 (dd, 1 H); 5.96 (s, 1 H); 7.30 (m, 1 H); 7.38 - 7.47 (m, 1 H); 7.48 - 7.55 (m, 1 H).MS (ESI+): [M + H]+ = 386

Reference： [1]Patent: WO2011/76687,2011,A1 .Location in patent: Page/Page column 138

66
[ 85920-63-4 ]
[ 1326706-84-6 ]
[ 1326706-75-5 ]

Yield	Reaction Conditions	Operation in experiment
67%		Acetyl Meldrum?s acid was prepared as described by Crimmins31 and recrystallized from cyclohexane. Acetyl Meldrum?s acid (269 mg, 1.44 mmol) was added to a solution of isoquinoline 16 (158 mg, 0.72 mmol) in freshly dried toluene (5 mL). The reaction was heated to 110 C and monitored by TLC every 15 min until the starting material was consumed completely. Then KOtBu (122 mg, 1.08 mmol) was added and the mixture refluxed for another 2 h. After evaporation of the solvent, the residue was dissolved in methanol (2 mL) and the pH was adjusted to 1 by slow addition of 1 M HCl. The mixture was extracted with dichloromethane twice, the combined organic layers were dried with Na2SO4 and the solvents were removed under reduced pressure. Column chromatography of the crude product (ethyl acetate-EtOH 9:1) yielded tetramic acid 6 (131 mg, 67%) as an oil. IR (film): 3419, 1601, 1661, 879 cm-1; 1H NMR (400 MHz, CDCl3): delta 1.79 (s, 3H), 1.84/1.87 (s, 3H), 2.43 (br s, 3H), 2.62 (t, J = 13.7 Hz, 1H), 3.17 (dd, J = 14.8, 2.5 Hz, 1H), 3.68 (m, 1H), 7.18 (m, 2H), 7.26 (t, J = 6.1 Hz, 1H), 7.35 (d, J = 8.1 Hz, 1H); 13C NMR (100 MHz, CDCl3): delta 26.7, 27.5, 31.5, 33.2, 33.5, 58.6, 58.8, 60.8, 61.3, 103.84, 126.4, 127.3, 127.4, 128.1, 128.3, 129.9, 133.9, 134.1, 145.5, 146.0, 174.5, 175.2, 195.3, 195.8; MS (ESI): m/z (%) 272.1 ([M+H]+, 100); HR MS (ESI) calcd for C16H16NO3 ([M-H]-): 270.1136, found 270.1137.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4669 - 4678

67
[ 85920-63-4 ]
[ 1326706-88-0 ]
[ 1326706-76-6 ]

Yield	Reaction Conditions	Operation in experiment
71%		Acetyl Meldrum?s acid (92 mg, 0.48 mmol) was added to dihydro-isoindole 23 (50 mg, 0.24 mmol) in toluene (2 mL). The reaction mixture was heated to 80 C and monitored every 15 min until complete consumption of the starting material. Then the solvent was evaporated and the residue was dried in high vacuum for 12 h. A 0.5 M sodium ethoxide solution (1 mL, 0.50 mmol) was added to the raw material (68 mg, 0.23 mmol) of step one in EtOH (2 mL) at 0 C. The reaction was refluxed for 2 h, the solvent evaporated after that time and the residue dissolved in methanol (2 mL). Aq HCl (1 M) was added until pH 1. The solution was extracted with dichloromethane (3 × 25 mL), the organic phase was dried with Na2SO4, filtered and concentrated in vacuo. Chromatographic purification of the crude product (ethyl acetate-EtOH 100:8) afforded tetramic acid 7 (40.0 mg, 71%) as a white amorphous powder. IR (KBr): 1615, 2965, 3432 cm-1; 1H NMR (400 MHz, CDCl3): delta 1.19/1.20 (s, 3H), 2.12/2.13 (s, 3H), 2.57/2.58 (s, 3H), 4.94 (s, 1H), 7.19-7.65 (m, 4H); 13C NMR (100 MHz, CDCl3): delta 23.3/25.1, 26.7/28.9, 31.6/32.2, 66.2, 69.4, 119.3, 120.9, 122.0, 127.4, 128.0, 136.2, 148.3, 159.6, 178.2,195.3; MS (ESI): m/z (%) 258.1 ([M+H]+, 100); HR MS (ESI): calcd for C15H14NO3 ([M-H]-): 256.0979, found 256.0978.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4669 - 4678

68
[ 85920-63-4 ]
rac-(1R,3aR,7aS)-3,3-dimethyl-octahydro-isoindole-1-carboxylic acid methyl ester [ No CAS ]
rac-(5aR,9aS,9bR)-2-(1-hydroxyethylidene)-5,5-dimethyloctahydro-1H-pyrrolo[2,1-a]isoindole-1,3(2H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		A solution of octahydro-isoindole 24 (67 mg, 0.32 mmol) and acetyl Meldrum?s acid (118 mg, 0.63 mmol, freshly prepared) in toluene (5 mL) was refluxed for 2 h, cooled to room temperature and evaporated. The residue was dried in high vacuum for 12 h, dissolved in 1 M NaOEt in EtOH (1 mL) and refluxed for 2 h at 80 C. After cooling to room temperature the reaction was poured in 2 M HCl solution (20 mL) and extracted with dichloromethane (3 × 25 mL). The combined organic phases were dried with Na2SO4, filtered and evaporated. Pure tetramic acid 8 (52.0 mg, 61%) was obtained after reversed phase column chromatography (acetonitrile-water 6:4) as a white amorphous powder. IR (KBr): 1572, 1682, 3320 cm-1; 1H NMR (600 MHz, acetonitril-d3): delta 4.24 (d, J = 6 Hz, 1H), 2.36 (s, 3H), 2.35 (m, 1H), 2.30 (m, 1H), 1.73 (m, 2H), 1.66 and 1.24 (m, each 1H), 1.67 (s, 3H), 1.54 and 1.04 (m, each 1H), 1.48-1.45 (m, 2H), 1.39 (s, 3H); 13C NMR (150 MHz, acetonitril-d3): delta 19.6, 22.2, 22.7, 24.3, 24.4, 24.6, 30.8, 39.5, 51.0, 63.6, 71.7, 106.8, 174.2, 184.4, 194.7; MS (ESI): m/z (%): 264.2 ([M+H]+, 100); HR MS (ESI): calcd. for C15H22NO3 ([M+H]+): 264.1594, found 264.1596.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4669 - 4678

69
[ 85920-63-4 ]
rac-(1S,3aR,7aS)-3,3-dimethyloctahydroisoindole-1-carboxylic acid methyl ester [ No CAS ]
rac-(5aR,9aS,9bS)-2-(1-hydroxyethylidene)-5,5-dimethyloctahydro-1H-pyrrolo[2,1-a]isoindole-1,3(2H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		A solution of octahydro-isoindole 25 (29 mg, 0.14 mmol) and acetyl Meldrum?s acid (51 mg, 0.27 mmol) in toluene (5 mL) was refluxed for 2 h at 110 C, cooled to room temperature and evaporated. Then a 0.3 M NaOEt solution (1 mL, 0.30 mmol) was added to the dried residue (12 h high vacuum) dissolved in EtOH (2 mL). The mixture was refluxed at 80 C for 2 h, cooled to room temperature and evaporated. The resulting residue was dissolved in of 2 M HCl solution (25 mL) and extracted with dichloromethane (3 × 25 mL). The combined organic phases were dried with Na2SO4 and evaporated. Chromatographic purification on a reversed phase column (acetonitrile-water 6:4) yielded tetramic acid 9 (21.0 mg, 74%) as a white amorphous powder. IR (KBr): 1572, 1682, 3320 cm-1; 1H NMR (600 MHz, acetonitril-d3): delta 4.24 (d, J = 12 Hz, 1H), 2.34 (s, 3H), 2.33 (m, 1H), 2.14 and 1.67 (m, each 1H), 1.71 and 1.44 (m, each 1H), 1.81 and 1.21 (m, each 1H), 1.59 and 1.44 (m, each 1H), 1.49 and 1.40 (s, each 3H); 13C NMR (150 MHz, acetonitril-d3): delta 19.8, 21.5, 24.4, 24.9, 25.0, 25.9, 26.1, 38.6, 53.3, 64.5, 69.1, 106.5, 176.7, 185.3, 197.0; MS (ESI): m/z (%): 264.2 ([M+H]+, 100); HR MS (ESI): calcd for C15H22NO3 ([M+H]+): 264.1594, found 264.1597.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4669 - 4678

70
[ 85920-63-4 ]
5-(acetyl-O-methoxyoxime)-5-bromo-Meldrum's acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 1962 - 1965

71
[ 85920-63-4 ]
5-(acetyl-O-methoxyoxime)-5-(N-(N,O-bis(t-butoxycarbonyl))-hydroxylamine)-Meldrum's acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 1962 - 1965

72
[ 85920-63-4 ]
[ 1354790-93-4 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 1962 - 1965

73
[ 85920-63-4 ]
C₉H₁₂NO₅^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 1962 - 1965

74
[ 85920-63-4 ]
[ 593-56-6 ]
5-(acetyl-O-methoxyoxime)-Meldrum's acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 1962 - 1965

75
[ 2033-24-1 ]
acetyl halide [ No CAS ]
[ 85920-63-4 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2012,vol. 187,p. 1109 - 1117

76
[ 85920-63-4 ]
[ 603-35-0 ]
[ 762-21-0 ]
[ 1384486-04-7 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2012,vol. 187,p. 1109 - 1117

77
[ 85920-63-4 ]
C₂₃H₃₃NO₈ [ No CAS ]
[ 1430068-89-5 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 3421 - 3424
Angew. Chem.,2013,vol. 125,p. 3505 - 3508,4

78
methyl 2-(cyclopropylmethyl)Δ²-1 ,3-thiazoline-4-carboxylate [ No CAS ]
[ 85920-63-4 ]
methyl (3R)-8-cyclopropyl-7-methyl-5-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With trifluoroacetic acid; In 1,2-dichloro-ethane; at 120℃; for 0.05h;Microwave irradiation;	General procedure: Ring-fused thiazolino 2-pyridones were prepared from dihydrothiazolines and acyl Meldrum's acid by adaptation of the procedure reported by Chorell et al.n TFA (1.0 eq.) was added to a solution of the 2-alkyl-A -thiazoline (1.0 eq.) and acyl Meldrum's acid (2.75 eq.) in 1 ,2-dichloroethane (5 mL) and heated by MWI at 120 C for 3 min. After cooling to rt, the reaction mixture was quenched with saturated aqueous NaHC03 solution (20 mL) and extracted with CH2C12 (3 chi 15 mL). The combined organic extracts were washed successively with H20 and brine (50 mL each), dried (Na2S04) and the solvent removed under reduced pressure. Purification by flash chromatography (Si02, EtOAc in heptane) afforded the product.

Reference： [1]Patent: WO2014/185853,2014,A1 .Location in patent: Page/Page column 51-53
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 2094 - 2108

79
[ 3230-65-7 ]
[ 85920-63-4 ]
[ 256378-46-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 205 - 210

80
4-(dodecylamino)phenol [ No CAS ]
[ 85920-63-4 ]
N-dodecyl-N-(4-hydroxyphenyl)-3-oxobutanamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 2064 - 2077

81
4-(dodecylamino)phenol [ No CAS ]
[ 85920-63-4 ]
N-(4-hydroxybenzyl)-N-dodecyl-3-oxobutanamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 2064 - 2077

82
[ 85920-63-4 ]
[ 103-14-0 ]
[ 1309579-57-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 2064 - 2077

83
copper(ll) sulfate pentahydrate [ No CAS ]
[ 85920-63-4 ]
C₁₆H₁₈CuO₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.6 g		In water 80mL, Compound A 1.86g a (10mmol) was added, and further added 10mL of 1mol / L sodium hydroxide solution, stirred for about 10 minutes to dissolve the Compound A, to give Compound A solution 2.Then added a solution of copper sulfate pentahydrate 1.24g (5mmol) of water 20mL Compound A solution 2, and stirred at room temperature for 30 minutes.Resulting crystals were collected by filtration, washed over the water, to obtain a copper complex 1-4 and dried as blue powder 1.6g (Exemplified Compound 1).

Reference： [1]Patent: KR2015/43489,2015,A .Location in patent: Paragraph 0285-0287

84
[ 85920-63-4 ]
copper dichloride [ No CAS ]
C₁₆H₁₈CuO₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.9 g	With triethylamine; In N,N-dimethyl acetamide; at 20℃; for 0.5h;	The resulting compound A 1.86g (10mmol), was dissolved by adding N,N- dimethylacetamide 10mL, to give Compound A solution.Then adding anhydrous copper chloride 650mg (5mmol) N of 5mL, in the Compound A solution in N,N- dimethylacetamide, followed by addition of triethylamine 1.4mL (10mmol), and the mixture was stirred at room temperature for 30 minutes.After the resultant was added and the mixture vigorously stirred while 90mL of water, and allowed to stand for 30 minutes, resulting crystals were collected by filtration, washed over with water, the copper complex as a light blue powder and dried to obtain a 1.9g 1- 3 (Exemplified Compound 1)

Reference： [1]Patent: KR2015/43489,2015,A .Location in patent: Paragraph 0278; 0284

85
[ 85920-63-4 ]
[ 926-02-3 ]
C₁₁H₁₆O₅ [ No CAS ]

Reference： [1]Organic Syntheses,2000,vol. 77,p. 114 - 114

86
[ 110-87-2 ]
[ 85920-63-4 ]
C₁₀H₁₂O₅ [ No CAS ]

Reference： [1]Organic Syntheses,2000,vol. 77,p. 114 - 114

87
[ 85920-63-4 ]
[ 928-55-2 ]
C₁₀H₁₄O₅ [ No CAS ]

Reference： [1]Organic Syntheses,2000,vol. 77,p. 114 - 114

88
[ 111-34-2 ]
[ 85920-63-4 ]
6-butoxydihydro-3-(1-hydroxyethylidene)-2H-pyran-2,4(3H)-dione [ No CAS ]

Reference： [1]Organic Syntheses,2000,vol. 77,p. 114 - 114

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 85920-63-4 ]

Alkenes

[ 15568-85-1 ]

5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Similarity: 0.85

[ 3044-06-2 ]

Diethyl 2-(1-ethoxyethylidene)malonate

Similarity: 0.75

[ 1462-12-0 ]

Diethyl 2-ethylidenemalonate

Similarity: 0.68

[ 87-13-8 ]

Diethyl 2-(ethoxymethylene)malonate

Similarity: 0.64

[ 55750-84-0 ]

Crocin II

Similarity: 0.63

Aliphatic Cyclic Hydrocarbons

[ 13137-64-9 ]

4-((3S,5S,8R,9S,10R,13R,14S,17R)-5,14-Dihydroxy-3-(((2R,4S,5R,6R)-4-methoxy-6-methyl-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one

Similarity: 0.54

[ 6990-06-3 ]

(Z)-2-((3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyldodecahydro-1H-cyclopenta[a]phenanthren-17(2H,10H,14H)-ylidene)-6-methylhept-5-enoic acid

Similarity: 0.51

[ 14216-03-6 ]

(4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-(2S,3R,4S,5S,6R)-6-((((2R,3R,4R,5S,6R)-3,4-Dihydroxy-6-(hydroxymethyl)-5-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl 10-(((2S,3R,4S,5S)-4,5-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Similarity: 0.51

[ 3232-07-3 ]

Bicyclo[2.2.1]hept-5-en-2-yl methacrylate

Similarity: 0.50

[ 25662-28-6 ]

Methyl 1-cyclopentene-1-carboxylate

Similarity: 0.50

Esters

[ 15568-85-1 ]

5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Similarity: 0.85

[ 3044-06-2 ]

Diethyl 2-(1-ethoxyethylidene)malonate

Similarity: 0.75

[ 137571-73-4 ]

5,7-Dihydroxy-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Similarity: 0.75

[ 5394-63-8 ]

2,2,6-Trimethyl-4H-1,3-dioxin-4-one

Similarity: 0.73

[ 1462-12-0 ]

Diethyl 2-ethylidenemalonate

Similarity: 0.68

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
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. 85920-63-4 ] {[proInfo.proName]}

Quality Control of [ 85920-63-4 ]

Related Doc. of [ 85920-63-4 ]

Product Details of [ 85920-63-4 ]

Calculated chemistry of [ 85920-63-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 85920-63-4 ]

Application In Synthesis of [ 85920-63-4 ]

[ 85920-63-4 ] Synthesis Path-Upstream 1~4

[ 85920-63-4 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 85920-63-4 ]

Alkenes

Aliphatic Cyclic Hydrocarbons

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 85920-63-4 ]