[ CAS No. 1530-39-8 ] {[proInfo.proName]}

Name: 1530-39-8|(4-Chlorobenzyl)triphenylphosphonium chloride|97%
Brand: Ambeed
SKU: A494980
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2D 3D

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Quality Control of [ 1530-39-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1530-39-8 ]

Product Details of [ 1530-39-8 ]

CAS No. :	1530-39-8	MDL No. :	MFCD00041533
Formula :	C₂₅H₂₁Cl₂P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RAHOAHBOOHXRDY-UHFFFAOYSA-M
M.W :	423.31	Pubchem ID :	2733546
Synonyms :

Calculated chemistry of [ 1530-39-8 ]

Physicochemical Properties

Num. heavy atoms :	28
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.04
Num. rotatable bonds :	5
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	126.36
TPSA :	13.59 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.62
Log Po/w (XLOGP3) :	7.55
Log Po/w (WLOGP) :	2.69
Log Po/w (MLOGP) :	7.16
Log Po/w (SILICOS-IT) :	6.79
Consensus Log Po/w :	4.71

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-7.53
Solubility :	0.0000126 mg/ml ; 0.0000000298 mol/l
Class :	Poorly soluble
Log S (Ali) :	-7.67
Solubility :	0.00000902 mg/ml ; 0.0000000213 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-11.01
Solubility :	0.0000000041 mg/ml ; 0.0 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.35

Safety of [ 1530-39-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1530-39-8 ]

* 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 [ 1530-39-8 ]

[ 1530-39-8 ] Synthesis Path-Downstream 1~88

1
[ 13466-40-5 ]
[ 1530-39-8 ]
[ 36288-11-6 ]

Reference： [1]Canadian Journal of Chemistry,1972,vol. 50,p. 528 - 533

2
[ 66-77-3 ]
[ 1530-39-8 ]
1-[(Z)-2-(4-Chloro-phenyl)-vinyl]-naphthalene [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1972,vol. 50,p. 528 - 533

3
[ 2746-25-0 ]
[ 1530-39-8 ]
[ 15107-36-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1967,vol. 704,p. 109 - 141

4
[ 1530-39-8 ]
[ 104-83-6 ]
[ 15107-35-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1967,vol. 704,p. 109 - 141

5
[ 104-83-6 ]
[ 603-35-0 ]
[ 1530-39-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	In toluene; for 6h;Reflux;	General procedure: Triphenylphosphine (5 mmol) was added to a solution of 4-substituted-benzyl halide (5 mmol) in toluene (50 mL). The mixture was heated to reflux for 6 h and then cooled to room temperature. The precipitate was collected, recrystallized from ethanol to give the products.
	In benzene;Reflux;	General procedure: A mixture of 1.67 g (10.70 mmol) of 1-(chloromethyl)-4-methoxybenzene, 3.35 g (12.8 mmol) of triphenylphosphine, and 11 mL of ethyl acetate was stirred and refluxed for 24 hours and the salt, (4-methoxybenzyl)triphenylphosphonium chloride, was gradually formed and then collected and dried by suction filtration after cooling down.

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300
[2]European Journal of Medicinal Chemistry,2011,vol. 46,p. 2908 - 2916
[3]Canadian Journal of Chemistry,2005,vol. 83,p. 1543 - 1553
[4]Organic Process Research and Development,2008,vol. 12,p. 156 - 162
[5]Justus Liebigs Annalen der Chemie,1967,vol. 704,p. 109 - 141
[6]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 679 - 683
[7]Journal of Organic Chemistry,1993,vol. 58,p. 5643 - 5649
[8]Journal of Chemical Research, Miniprint,1986,p. 3514 - 3530
[9]Helvetica Chimica Acta,1994,vol. 77,p. 1921 - 1939
[10]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 671 - 673
[11]Journal of the Chinese Chemical Society,1998,vol. 45,p. 517 - 523
[12]Journal of the Chinese Chemical Society,1998,vol. 45,p. 517 - 523
[13]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017
[14]Tetrahedron Letters,2013,vol. 54,p. 1991 - 1993
[15]Organic Letters,2019,vol. 21,p. 5438 - 5442

6
[ 98-01-1 ]
[ 1530-39-8 ]
[ 52792-15-1 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1981,vol. 46,p. 515 - 519

7
[ 23145-19-9 ]
[ 1530-39-8 ]
[ 139201-62-0 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1299 - 1318

8
[ 3034-50-2 ]
[ 1530-39-8 ]
[ 75840-89-0 ]
[ 75840-90-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 679 - 683

9
[ 7044-91-9 ]
[ 1530-39-8 ]
[ 136384-81-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 861 - 867

10
[ 13949-93-4 ]
[ 1530-39-8 ]
ethyl cis,trans-2-(2-p-chlorophenyl-cis,trans-ethenyl)cyclopropane carboxylate [ No CAS ]

Reference： [1]Phytochemistry,1988,vol. 27,p. 3751 - 3756

11
[ 104-87-0 ]
[ 1530-39-8 ]
[ 3041-83-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

12
[ 104-88-1 ]
[ 1530-39-8 ]
[ 2510-74-9 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

13
[ 55876-91-0 ]
[ 1530-39-8 ]
[ 138815-50-6 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 804 - 807

14
[ 1530-39-8 ]
[ 89560-00-9 ]
methyl 9-(4-chlorophenyl)-7,7-dimethyl-5(Z),8(Z)-nonadienoate [ No CAS ]
methyl 9-(4-chlorophenyl)-7,7-dimethyl-5(Z),8(E)-nonadienoate [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,1988,vol. 77,p. 149 - 152

15
[ 1530-39-8 ]
C₂₅H₂₁ClP⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 5643 - 5649

16
[ 1530-39-8 ]
[ 100-52-7 ]
[ 1657-50-7 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

17
[ 1530-39-8 ]
[ 90-02-8 ]
[ 42224-49-7 ]
[ 42224-51-1 ]

Reference： [1]Journal of Chemical Research, Miniprint,1986,p. 3514 - 3530
[2]Journal of Chemical Research, Miniprint,1986,p. 3514 - 3530

18
[ 603-35-0 ]
[ 873-76-7 ]
[ 1530-39-8 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 5643 - 5649

19
[ 832-62-2 ]
[ 1530-39-8 ]
[ 55168-64-4 ]
1-<(E)-2-(4-chlorophenyl)ethenyl>-4,6,8-trimethylazulene [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1994,vol. 77,p. 1921 - 1939

20
[ 39561-82-5 ]
[ 1530-39-8 ]
(E)-2,3-bis(4-chlorophenyl)prop-2-en-1-yl acetate [ No CAS ]
(Z)-2,3-bis(4-chlorophenyl)prop-2-en-1-yl acetate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1877 - 1880

21
[ 1530-39-8 ]
[ 107496-65-1 ]
(E)-3-(4-chlorophenyl)-2-(2,4-dichlorophenyl)prop-2-en-1-yl acetate [ No CAS ]
(Z)-3-(4-chlorophenyl)-2-(2,4-dichlorophenyl)prop-2-en-1-yl acetate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1877 - 1880

22
[ 1530-39-8 ]
[ 874-60-2 ]
(α-4-chlorophenyl-α-4-methylbenzoylmethylene)triphenylphosphorane [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1995,vol. 101,p. 281 - 286

23
[ 1530-39-8 ]
[ 122-01-0 ]
[ 52792-17-3 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1995,vol. 101,p. 281 - 286

24
[ 79-37-8 ]
[ 1530-39-8 ]
1,4-Bis-(4-chloro-phenyl)-1,4-bis-(triphenyl-λ⁵-phosphanylidene)-butane-2,3-dione [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 485 - 489

25
[ 1530-39-8 ]
C₁₈H₁₄O₂ [ No CAS ]
C₃₂H₂₄Cl₂ [ No CAS ]
C₃₂H₂₄Cl₂ [ No CAS ]

Reference： [1]Chemical Communications,1996,p. 655 - 656

26
[ 1530-39-8 ]
[ 13750-81-7 ]
2-[(Z)-2-(4-Chloro-phenyl)-vinyl]-1-methyl-1H-imidazole [ No CAS ]
[ 181486-44-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 671 - 673

27
[ 17071-97-5 ]
[ 1530-39-8 ]
[ 186707-20-0 ]
[ 186707-18-6 ]

Reference： [1]Heterocycles,1997,vol. 44,p. 187 - 196

28
[ 4746-97-8 ]
[ 1530-39-8 ]
[ 221533-40-0 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

Yield	Reaction Conditions	Operation in experiment
		(a) [(4-Chlorophenyl)methyl]triphenylphosphonium chloride A stirred solution of 158 g, (0.6 mole) of triphenylphosphine in 800 ml of xylene is treated with 97 g of 4-chlorobenzyl chloride. The resulting solution is heated (product begins to crystallize at this point) and refluxed for six hours. After standing overnight at room temperature, the solid is filtered, washed with xylene and then with ethyl acetate, and dried in a desiccator to yield 161 g of colorless solid [(4-chlorophenyl)methyl]triphenylphosphonium chloride; m.p. 283-285.
		(a) [(4-Chlorophenyl)methyl]triphenylphosphonium chloride Triphenylphosphine (158 g., 0.60 mole) and 97 g. of 4-chlorobenzyl chloride are reacted in 800 ml. of boiling xylene according to the procedure of Example 25 (a) to yield 161 g. of colorless solid [(4-chlorophenyl)methyl]triphenylphosphonium chloride; m.p. 283-285.

31
[ 1530-39-8 ]
[ 253778-43-7 ]
dimethyl 8-(tert-butyl)-6-[(E)-2-(4-chlorophenyl)ethenyl]-1,10-dimethylheptalene-4,5-dicarboxylate [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1999,vol. 82,p. 1690 - 1706

32
[ 437-81-0 ]
[ 1530-39-8 ]
2-[(E)-2-(4-Chloro-phenyl)-vinyl]-1,3-difluoro-benzene [ No CAS ]

Reference： [1]Journal of Molecular Structure,2001,vol. 563-564,p. 513 - 516

33
[ 459-57-4 ]
[ 1530-39-8 ]
[ 39769-26-1 ]

Reference： [1]Journal of Molecular Structure,2001,vol. 563-564,p. 513 - 516

34
[ 1530-39-8 ]
[ 38897-99-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 0℃; for 0.5h;	Step 1 : 4-bromo-2-[2-(4-chlorophenyl)vinyl]thiophene; To a solution of <strong>[1530-39-8](4-chlorobenzyl)triphenylphosphonium chloride</strong> (17.3g) in DMF (200 mL) at 0 0C, was added NaH (60 % in oil, 2g). The mixture was stirred at 0 C for 30 minutes, after which a solution of 4-bromothiophene-2-carbaldehyde (8 g) in DMF (20 mL) was added. The mixture was stirred at 0 0C for 30 minutes, then warmed up to room temperature and stirred 1 hr. The reaction mixture was quenched by the addition of 1 N HCl and Et20. The aqueous layer was extracted with Et2O, the combined organic layers were washed with brine, dried over Na2SO4 and filtered. The volatiles were removed under reduced pressure and the residue was purified by flash chromatography on silica (100 % hexanes) to afford 4-bromo-2-[2-(4- chlorophenyl)vinyl]thiophene (10 g) as a mixture of isomers.

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598
[2]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598
[3]Synlett,2010,p. 2257 - 2262
[4]Patent: WO2007/134434,2007,A1 .Location in patent: Page/Page column 64

35
[ 1530-39-8 ]
[ 506437-20-3 ]
C₂₆H₂₂ClN₃O₂S [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 5551 - 5554

36
[ 1530-39-8 ]
[ 57948-15-9 ]
5-[2Z-(4-chlorophenyl)ethenyl]benzo[1,2,5]oxadiazole 1-oxide [ No CAS ]
5-[2E-(4-chlorophenyl)ethenyl]benzo[1,2,5]oxadiazole 1-oxide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6336 - 6346

37
[ 329-98-6 ]
[ 1530-39-8 ]
[ 878801-19-5 ]

Reference： [1]Canadian Journal of Chemistry,2005,vol. 83,p. 1543 - 1553

38
[ 1530-39-8 ]
[ 681443-29-8 ]
1,1,2,2,3,3,4,4,4-nonafluoro-butane-1-sulfonic acid (2-[(4-chloro-phenyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-azo}-phenyl)-amide [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 7845 - 7848

39
[ 1530-39-8 ]
[ 41482-18-2 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 5551 - 5554

40
[ 1530-39-8 ]
[ 630413-80-8 ]

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598

41
[ 1530-39-8 ]
[ 630413-82-0 ]

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598

42
[ 1530-39-8 ]
[ 652968-68-8 ]

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598

43
[ 1530-39-8 ]
(E)-4'-chloro-6-methyl-3-styrylchromone [ No CAS ]

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598

44
[ 1530-39-8 ]
(Z)-4'-chloro-5-methoxy-3-styrylchromone [ No CAS ]

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598

45
[ 1530-39-8 ]
(E)-4'-chloro-5-methoxy-3-styrylchromone [ No CAS ]

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598

46
[ 1530-39-8 ]
[ 35883-77-3 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

47
[ 1530-39-8 ]
[ 83631-88-3 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

48
[ 1530-39-8 ]
(6R,6S)-2,4-diamino-6-benzyl-5,6,7,8-tetrahydroquinazoline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

49
[ 873-76-7 ]
[-(CH₂)2-NH-(CH₂)3-N-]-CO₂-CH₂-Wang resin [ No CAS ]
[ 1530-39-8 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

50
[ 1530-39-8 ]
[ 62102-59-4 ]

Reference： [1]Heterocycles,1997,vol. 44,p. 187 - 196
[2]Heterocycles,1997,vol. 44,p. 187 - 196
[3]Heterocycles,1997,vol. 44,p. 187 - 196

51
[ 1530-39-8 ]
[ 186707-20-0 ]

Reference： [1]Heterocycles,1997,vol. 44,p. 187 - 196

52
[ 1530-39-8 ]
2-[2-(4-Chloro-phenyl)-ethyl]-1-methyl-1H-imidazole [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 671 - 673

53
[ 1530-39-8 ]
[ 51118-06-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 485 - 489

54
[ 1530-39-8 ]
[ 22711-23-5 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1995,vol. 101,p. 281 - 286

55
[ 1530-39-8 ]
[ 86508-29-4 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1995,vol. 101,p. 281 - 286

56
[ 873-76-7 ]
[ 1530-39-8 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 5643 - 5649

57
[ 74-11-3 ]
[ 1530-39-8 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 5643 - 5649
[2]Journal of Organic Chemistry,1993,vol. 58,p. 5643 - 5649

58
[ 1530-39-8 ]
[ 61692-96-4 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

59
[ 1530-39-8 ]
ethyl trans-2,3-bis(4-chlorophenyl)cyclopropanecarboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

60
[ 1530-39-8 ]
[ 143959-19-7 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

61
[ 1530-39-8 ]
[ 143959-17-5 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

62
[ 1530-39-8 ]
[ 143959-20-0 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

63
[ 1530-39-8 ]
[ 32096-16-5 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

64
[ 1530-39-8 ]
[ 143958-91-2 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

65
[ 1530-39-8 ]
[ 143959-15-3 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

66
[ 1530-39-8 ]
[ 143958-90-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

67
[ 1530-39-8 ]
ethyl trans-2-(4-chlorophenyl)-3-phenylcyclopropanecarboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

68
[ 1530-39-8 ]
(2S,3S)-2-(4-Chloro-phenyl)-3-p-tolyl-cyclopropanecarboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

69
[ 1530-39-8 ]
[ 143958-97-8 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

70
[ 1530-39-8 ]
[ 143958-99-0 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

71
[ 1530-39-8 ]
[ 144124-64-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

72
[ 1530-39-8 ]
[ 143959-06-2 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

73
[ 1530-39-8 ]
[ 143959-08-4 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

74
[ 1530-39-8 ]
[ 143959-04-0 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

75
[ 1530-39-8 ]
[ 143959-14-2 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6294 - 6300

76
[ 1530-39-8 ]
[ 139201-63-1 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1299 - 1318

77
[ 1530-39-8 ]
[ 138853-86-8 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1299 - 1318

78
[ 1530-39-8 ]
[ 138853-90-4 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1299 - 1318

79
[ 1530-39-8 ]
[ 138815-49-3 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 804 - 807

80
[ 1530-39-8 ]
[ 78443-37-5 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1981,vol. 46,p. 515 - 519

81
[ 1530-39-8 ]
[ 5216-35-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1967,vol. 704,p. 109 - 141

82
[ 1530-39-8 ]
[ 15107-41-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1967,vol. 704,p. 109 - 141

83
[ 1530-39-8 ]
[ 635-93-8 ]
4-Chloro-2-((4-chlorophenyl)ethen-2-yl]phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.4%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); water; for 5h;Heating / reflux;	5-Chlorosalicylaldehyde(313mg, 2mmol) and 4-chlorobenzyltriphenylphosphonium chloride(847mg, 2mmol) were dissolved in N,N-dimethylformamide(20mL). Potassium carbonate(1.382g, 10mmol) dissolved in water(10mL) was added, and the mixture was refluxed for 5 hours. After cooling, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel(n-hexane:ethyl acetate=3:1) to give the title compound(44.6mg, 8.4%) as a light gray solid.1H-NMR(CDCl3): delta 5.04(1H, s), 6.74(1H, d, J=9.0Hz), 7.05(1H, d, J=16.5Hz), 7.10(1H, dd, J=8.4, 2.4Hz), 7.26(1H, d, J=16.5Hz), 7.33(2H, d, J=8.4Hz), 7.45(2H, d, J=8.4Hz), 7.49(1H, d, J=2.4Hz).
8.4%	With potassium carbonate; In water; N,N-dimethyl-formamide; for 5h;Heating / reflux;	5-Chlorosalicylaldehyde(313mg, 2mmol) and 4-chlorobenzyltriphenylphosphonium chloride(847mg, 2mmol) were dissolved in N,N-dimethylfomamide(20mL). Potassium carbonate(1.382g, 10mmol) dissolved in water(10mL) was added, and the mixture was refluxed for 5 hours. After cooling, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel(n-hexane:ethyl acetate=3:1) to give the title compound(44.6mg, 8.4%) as a light gray solid.1H-NMR(CDCl3): delta 5.04(1H, s), 6.74(1H, d, J=9.0Hz), 7.05(1H, d, J=16.5Hz), 7.10(1H, dd, J=8.4, 2.4Hz), 7.26(1H, d, J=16.5Hz), 7.33(2H, d, J=8.4Hz), 7.45(2H, d, J=8.4Hz), 7.49(1H, d, J=2.4Hz).
8.4%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); water; for 5h;Heating / reflux;	5-Chlorosalicylaldehyde(313mg, 2mmol) and 4-chlorobenzyltriphenylphosphonium chloride(847mg, 2mmol) were dissolved in N,N-dimethylformamide(20mL). Potassium carbonate(1.382g, 10mmol) dissolved in water(10mL) was added, and the mixture was refluxed for 5 hours. After cooling, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel(n-hexane:ethyl acetate=3:1) to give the title compound(44.6mg, 8.4%) as a light gray solid.1H-NMR(CDCl3): delta 5.04(1H, s), 6.74(1H, d, J=9.0Hz), 7.05(1H, d, J=16.5Hz), 7.10(1H, dd, J=8.4, 2.4Hz), 7.26(1H, d, J=16.5Hz), 7.33(2H, d, J=8.4Hz), 7.45(2H, d, J=8.4Hz), 7.49(1H, d, J=2.4Hz).

Reference： [1]Patent: EP1510207,2005,A1 .Location in patent: Page/Page column 115
[2]Patent: EP1512396,2005,A1 .Location in patent: Page/Page column 114
[3]Patent: EP1514544,2005,A1 .Location in patent: Page/Page column 119-120

84
[ 253685-11-9 ]
[ 1530-39-8 ]
[ 349561-96-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In water; toluene;	Example 27 Z-[4-(4-Chloro-benzylidene)-2-(3-methoxy-phenyl)-cyclohex-2-enylmethyl]-dimethyl-amine; hydrochloride (41) and E-[4-(4-chloro-benzylidene)-2-(3-methoxy-phenyl)-cyclohex-2-enylmethyl]-dimethyl-amine; hydrochloride (46) 21.6 g potassium tert-butylate and 65 g 4-chlorobenzyltriphenylphosphonium chloride were suspended in 800 ml analytical grade toluene under a nitrogen atmosphere at room temperature and the suspension was then stirred at 70 C. for one hour. 11.5 g 4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enone in 100 ml analytical grade toluene were added at this temperature and the mixture was stirred at 70 C. for 3 days. The mixture was quenched with 500 ml water. The phases were separated and the aqueous phase was washed 3 times with 200 ml ethyl acetate each time. The combined organic phases were dried over magnesium sulfate and then freed from the solvent in vacuo. The solid which had precipitated out was filtered off and washed with diiso-ether. The combined organic phases were freed from the solvent in vacuo. The residue was purified by column chromatography on silica gel with ethyl acetate/methanol=9/1. 5.2 g E-[4-(4-chloro-benzylidene)-2-(3-methoxy-phenyl)-cyclohex-2-enylmethyl]-dimethyl-amine base were obtained as the first product fraction.

Reference： [1]Patent: US2003/69288,2003,A1

85
[ 179061-37-1 ]
[ 1530-39-8 ]
5-(4-chlorostilbene-4'-sulfonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol;	a) Synthesis of 5-(4-chlorostilbene-4'-sulfonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine To a solution of 0.800 g (2.746 mmol) of 4-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-ylsulfonyl)benzaldehyde and 1.16 g (2.75 mmol) of 4-chlorobenzyltriphenylphosphonium chloride in 30 ml of methanol, 0.53 g (2.75 mmol) of 28% sodium methoxide in methanol was added dropwise at room temperature, followed by overnight stirring at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was subjected to silica gel column chromatography (hexane/ethyl acetate=3/1) to remove triphenylphosphine oxide, followed by crystallization from diethyl ether-hexane to yield the (E)-isomer. White solid Yield 0.303 g (28%) 1 H-NMR (CDCl3, 200 MHz) delta: 2.746(2H,br t,J=5.7 Hz), 3.499(2H,t,J=5.7 Hz), 4.145(1H,s), 6.193(1H,d,J=2.2 Hz), 7.060(1H,d,J=16.4 Hz), 7.176(1H,d,J=16.6 Hz), 7.352(2H,d,J=8.8 Hz), 7.466(2H,d,J=8.8 Hz), 7.609(2H,d,J=8.8 Hz), 7.798(2H,d,J=8.6 Hz) IR (nujol): 1344, 1321, 1165, 1140, 1088, 1005, 966, 945, 833, 756, 733 cm-1

Reference： [1]Patent: US5998433,1999,A

86
1-formyl-4-(N,N-diphenylamino)naphthalene [ No CAS ]
[ 865-47-4 ]
[ 1530-39-8 ]
[ 98660-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	In water; N,N-dimethyl-formamide;	SYNTHESIS EXAMPLE 21 42.3 g (0.1 mol) of 4-chlorobenzyltriphenylphosphonium chloride and 32.3 g (0.1 mol) of 4-N,N-diphenylaminonaphthaldehyde were dissolved in 100 ml of N,N-dimethylformamide. To this mixture, 16.8 g (0.15 mol) of potassium-tert-butoxide was added with the temperature of the reaction mixture maintained in the range of from 25 C. to 35 C. After the addition of the potassium-tert-butoxide, the reaction mixture was stirred at room temperature for 5 hours and was then diluted with 300 ml of water. Powder separated from the reaction mixture was filtered, washed with water and dried, whereby light yellow powder was obtained. The yield was 39.3 g (91%) and the melting point of the product was 126.0~127.5 C. Upon recrystallization of the powder from a mixed solvent of toluene and n-hexane in the presence of a small amount of iodine, 1-N,N-diphenylamino-4-(4-chlorostyryl) naphthalene precipitated as light yellow needle-like crystal. The yield was 34.8 g (80.7%). The melting point of the product was 127.0~128.5 C. The results of the elemental analysis of the thus obtained 1-N,N-diphenylamino-4-(4-chlorostyryl) naphthalene were as follows: The above calculation was based on the formula for 1-N,N-diphenylamino-4-(4-chlorostyryl) naphthalene of C30 H22 NC1.

Reference： [1]Patent: US5072043,1991,A

87
[ 7723-14-0 ]
[ 429-41-4 ]
[ 1530-39-8 ]
6-(1-p-chlorophenylbuten-4-yl)-5-hydroxy-3-methyl-2-p-methoxybenzyl-2,3-dihydrobenzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; hexane; ethyl acetate;	Step C To ethanol (5 ml) was added Na (4.6 mg, 0.2 mmoles) at room temperature. The mixture was stirred until the sodium was completely dissolved. To this cooled at 0 C. solution was added p-chlorobenzyl triphenylphosphonium chloride, (84.4 mg, 0.2 mmole) and this solution was stirred for 30 minutes. To this phosphorane solution was added E57 (50 mg, 0.11 mmoles). The reaction mixture was stirred at 0 C. for 1.30 hours. This solution was acidified with HCl 1N and concentrated in vacuo. The residue was chromatographed on silica gel using 10% ethyl acetate in hexane to yield 30 mg, 61% of 5-tert-butyldimethylsilyoxy derivative that was treated with tetrabutyl ammonium fluoride (53 mL, 0.05 mmole) and stirred for 1 hour at 0 C. The reaction mixture was then concentrated in vacuo. The residue was chromatographed on silica gel and eluted with 10% ethyle acetate in hexane to yield 6-(1-p-chlorophenylbuten-4 -yl)-5-hydroxy-3-methyl-2-p-methoxybenzyl-2,3-dihydrobenzofuran, E58. 1 H NMR delta: 1.15 (d, J=6 Hz, 3H), 1.28 (d, J=6 Hz, 3H), 2.3-3.3 (m, 7H), 3.8 (s, 3H), 4.1 (m, 1H), 4.35 (s, 1H, hydroxy), 6.3 (s, 1H, olefinic), 6.5 (s, 2H), 6.85 (d, 7.5 Hz, 2H), 7.28 (m, 6H, p-chlorophenyl).

Reference： [1]Patent: US5091533,1992,A

88
ethyl acetate n-hexane [ No CAS ]
[ 1070-89-9 ]
[ 1530-39-8 ]
[ 89560-00-9 ]
[ 102092-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	c. Methyl 9-(4-chlorophenyl)-7,7-dimethyl-5(Z),8-nonadienoate Formula (I): R1 =CH3; R2 =CH3; R3 =4--Cl; X=--CH=CH--; Y=--CO2 CH3. In a dry three-neck flask equipped with an addition funnel and a mechanical stirrer under an atmosphere of N2 was placed 120 ml of THF and 9.5 g (0.0224 mole) of 4-chlorobenzyltriphenylphosphonium chloride (Alfa) and 4.1 g (0.0224 mole) of N-sodiumhexamethyldisilazane (from Petrarch Systems Inc.). The mixture as allowed to stir at room temperature for 0.5 hours, then a solution of 3.8 g (0.019 mole) of methyl 7,7-dimethyl-8 oxo-5(Z)octenoate, the product of Example 8b, in 20 ml of THF was added dropwise. The reaction mixture was stirred at room temperature for 12 hours and then at 70 C. for 4 hours. The resulting mixture was allowed to cool to room temperature and then was poured into an ice-water mixture. The aqueous solution was acidified with 1N HCl and extracted with ether three times. The organic solution was washed with H2 O, 5% NaHCO3 solution, NaCl solution and dried over Na2 SO4. The residue, after removal of solvent, was purified through a silica gel column using hexane-ethyl acetate as an eluant to give the title compound, an oil.

Reference： [1]Patent: US4564476,1986,A

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