[ CAS No. 4707-71-5 ] {[proInfo.proName]}

Name: 4707-71-5|9-Phenanthrenecarboxaldehyde|97%
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Quality Control of [ 4707-71-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4707-71-5 ]

Product Details of [ 4707-71-5 ]

CAS No. :	4707-71-5	MDL No. :	MFCD00001175
Formula :	C₁₅H₁₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QECIGCMPORCORE-UHFFFAOYSA-N
M.W :	206.24	Pubchem ID :	78437
Synonyms :

Calculated chemistry of [ 4707-71-5 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	14
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.84
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.14
Log Po/w (XLOGP3) :	3.7
Log Po/w (WLOGP) :	3.81
Log Po/w (MLOGP) :	3.36
Log Po/w (SILICOS-IT) :	4.21
Consensus Log Po/w :	3.44

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.03
Solubility :	0.0192 mg/ml ; 0.0000931 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.75
Solubility :	0.0367 mg/ml ; 0.000178 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.7
Solubility :	0.000409 mg/ml ; 0.00000198 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 4707-71-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P301+P312	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4707-71-5 ]

* 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 [ 4707-71-5 ]
Downstream synthetic route of [ 4707-71-5 ]

[ 4707-71-5 ] Synthesis Path-Upstream 1~28

1
[ 573-17-1 ]
[ 68-12-2 ]
[ 4707-71-5 ]

Reference： [1] Tetrahedron, 1997, vol. 53, # 43, p. 14599 - 14614
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 44, p. 14593 - 14596[3] Angew. Chem., 2018, vol. 130, # 44, p. 14801 - 14805,5
[4] Bulletin of the Chemical Society of Japan, 1971, vol. 44, p. 2237 - 2248

2
[ 4707-72-6 ]
[ 4707-71-5 ]

Reference： [1] Tetrahedron, 1984, vol. 40, # 23, p. 5001 - 5004
[2] Synthetic Communications, 1984, vol. 14, # 9, p. 875 - 882

3
[ 51873-96-2 ]
[ 4707-71-5 ]

Reference： [1] Synthetic Communications, 1989, vol. 19, # 19, p. 3385 - 3396
[2] Synthetic Communications, 1989, vol. 19, # 20, p. 3469 - 3476

4
[ 106884-01-9 ]
[ 4707-71-5 ]

Reference： [1] Tetrahedron, 1990, vol. 46, # 19, p. 6869 - 6878
[2] Synthetic Communications, 1989, vol. 19, # 19, p. 3385 - 3396

5
[ 883-20-5 ]
[ 4707-71-5 ]

Reference： [1] Journal of Organic Chemistry, 1983, vol. 48, # 5, p. 749 - 751

6
[ 4885-02-3 ]
[ 85-01-8 ]
[ 4707-71-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 11, p. 3611 - 3622
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 19 - 24

7
[ 132556-01-5 ]
[ 4707-71-5 ]

Reference： [1] Tetrahedron, 1990, vol. 46, # 19, p. 6869 - 6878

8
[ 16331-54-7 ]
[ 4707-71-5 ]

Reference： [1] Journal of the American Chemical Society, 1933, vol. 55, p. 2995,2996

9
[ 85-01-8 ]
[ 68-12-2 ]
[ 4707-71-5 ]

Reference： [1] Synlett, 2000, # 8, p. 1115 - 1118
[2] Journal of the Indian Chemical Society, 2008, vol. 85, # 9, p. 959 - 961
[3] Synthetic Communications, 1999, vol. 29, # 4, p. 677 - 683

10
[ 64024-87-9 ]
[ 4707-71-5 ]

Reference： [1] Journal of Organic Chemistry, 1978, vol. 43, # 3, p. 381 - 387

11
[ 16231-67-7 ]
[ 4707-71-5 ]

Reference： [1] Journal of Organic Chemistry, 1978, vol. 43, # 3, p. 381 - 387

12
[ 63626-12-0 ]
[ 4707-71-5 ]

Reference： [1] Journal of Organic Chemistry, 1978, vol. 43, # 3, p. 381 - 387

13
[ 71112-64-6 ]
[ 122-51-0 ]
[ 4707-71-5 ]

Reference： [1] Journal of the Chemical Society, 1938, p. 193,195
[2] Journal of the American Chemical Society, 1938, vol. 60, p. 1331,1333
[3] Journal of the American Chemical Society, 1935, vol. 57, p. 766,769
[4] Organic Syntheses, 1955, vol. Coll. Vol. III, p. 701

14
[ 82491-33-6 ]
[ 883-20-5 ]
[ 4707-72-6 ]
[ 119521-93-6 ]
[ 4707-71-5 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2579 - 2584
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2579 - 2584
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2579 - 2584

15
[ 837-45-6 ]
[ 4707-71-5 ]

Reference： [1] Journal of the American Chemical Society, 1933, vol. 55, p. 2995,2996

16
[ 2591-86-8 ]
[ 71112-64-6 ]
[ 4707-71-5 ]

Reference： [1] Angewandte Chemie, 1981, vol. 93, # 10, p. 925 - 926

17
[ 64024-90-4 ]
[ 4707-71-5 ]

Reference： [1] Journal of Organic Chemistry, 1978, vol. 43, # 3, p. 381 - 387

18
[ 71112-64-6 ]
[ 109-94-4 ]
[ 401619-17-8 ]
[ 4707-71-5 ]

Reference： [1] Journal of the American Chemical Society, 1945, vol. 67, p. 1951,1954

19
[ 85-01-8 ]
[ 4707-71-5 ]

Reference： [1] Journal of the Chemical Society, 1936, p. 339,342

20
[ 408528-16-5 ]
[ 4707-71-5 ]

Reference： [1] Journal of the Chemical Society, 1933, p. 37,39

21
[ 2510-55-6 ]
[ 4707-71-5 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1957, vol. 607, p. 24,30

22
[ 85-01-8 ]
[ 761-65-9 ]
[ 4707-71-5 ]

Reference： [1] Synthetic Communications, 1999, vol. 29, # 4, p. 677 - 683

23
[ 85-01-8 ]
[ 109-94-4 ]
[ 4707-71-5 ]

Reference： [1] Synthetic Communications, 1999, vol. 29, # 4, p. 677 - 683

24
[ 573-17-1 ]
[ 100-10-7 ]
[ 4707-71-5 ]

Reference： [1] Journal of Organic Chemistry, 1960, vol. 25, # 10, p. 1691 - 1693

25
[ 38399-78-9 ]
[ 68-12-2 ]
[ 4707-71-5 ]

Reference： [1] Chemistry and Industry (London, United Kingdom), 1957, p. 1596

26
[ 7647-01-0 ]
[ 7446-70-0 ]
[ 74-90-8 ]
[ 85-01-8 ]
[ 108-90-7 ]
[ 4707-71-5 ]

Reference： [1] Journal of the Chemical Society, 1936, p. 339,342

27
[ 219-92-1 ]
[ 546-67-8 ]
[ 71-43-2 ]
[ 4707-71-5 ]

Reference： [1] Journal of the Chemical Society, 1947, p. 746,749

28
[ 546-67-8 ]
[ 71-43-2 ]
[ 4707-71-5 ]

Reference： [1] Journal of the Chemical Society, 1947, p. 746,749

[ 4707-71-5 ] Synthesis Path-Downstream 1~73

1
[ 5343-35-1 ]
[ 4707-71-5 ]
1-([9]phenanthrylmethyl-amino)-pentan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol anschliessendes Hydrieren an Platin;

Reference： [1]May [Journal of Organic Chemistry, 1946, vol. 11, p. 353,354,357]

2
[ 4707-71-5 ]
[ 4707-72-6 ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 6718 - 6722
[2]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 156 - 168
[3]European Journal of Medicinal Chemistry,2020,vol. 202
[4]Tetrahedron,2001,vol. 57,p. 2871 - 2884
[5]Inorganic Chemistry,2017,vol. 56,p. 13715 - 13731
[6]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 2595 - 2602
[7]Organic Letters,2007,vol. 9,p. 5429 - 5432
[8]European Journal of Organic Chemistry,2011,p. 942 - 950
[9]Synthetic Communications,1992,vol. 22,p. 497 - 507
[10]Journal of the American Chemical Society,1933,vol. 55,p. 2995,2996
[11]Journal of Organic Chemistry,1966,vol. 31,p. 95 - 99
[12]Synthetic Communications,1992,vol. 22,p. 497 - 507
[13]Macromolecules,2013,vol. 46,p. 1939 - 1947
[14]Chemical Communications,2015,vol. 51,p. 7610 - 7613
[15]Photochemical and Photobiological Sciences,2017,vol. 16,p. 925 - 934

3
[ 2921-14-4 ]
[ 4707-71-5 ]
[ 1157-06-8 ]

Reference： [1]Journal of medicinal chemistry,1964,vol. 7,p. 824 - 826

4
[ 4707-71-5 ]
[ 31603-73-3 ]

Yield	Reaction Conditions	Operation in experiment
20%	With hydrazine hydrate; In N,N-dimethyl acetamide; at 90℃; for 5h;Inert atmosphere;	General procedure: All compounds were prepared using the same procedure. 2 mmol of aldehyde was dissolved in 2 mL of DMA and 1 mmol of diamine in 2 mL DMA was added. In the case of Am-2, Az-3 and Am-3 0,1 mL TFA was added as catalyst. The reaction mixture was stirred and heated at 90 C under argon atmosphere for 5 h or for 24 h for Am-2, Az-3 and Am-3. The product was filtered, washed several times with methanol and dried at 60 C in vacuum.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2017,vol. 175,p. 168 - 176
[2]Journal of Organic Chemistry,1971,vol. 36,p. 3539 - 3541

5
[ 573-17-1 ]
[ 68-12-2 ]
[ 4707-71-5 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 14599 - 14614
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 14593 - 14596
Angew. Chem.,2018,vol. 130,p. 14801 - 14805,5
[3]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 2237 - 2248

6
[ 109-97-7 ]
[ 4707-71-5 ]
[ 126651-43-2 ]

Yield	Reaction Conditions	Operation in experiment
20%	In 1-Propyl acetate; for 1h;Reflux; Inert atmosphere;	H2TPHEP (2) was synthesized by the Adler-Longo method [40].A mixture of 9-phenanthrenecarboxaldehyde (618 mg, 3 mmol)and pyrrole (204 mg, 3 mmol) in propyl acid (30 ml) was refluxedfor 1 h under a slow stream of nitrogen, the CH3OH (100 mL) wasadded into the reaction solution after it had been cooled to roomtemperature. The precipitate was filtered and washed with CH3OH,then subjected to chromatography on a silica gel column withCHCl3 and petroleum ether (7:3) as eluent. After removing thesolvent in vacuo, the residue was re-chromatographed undersimilar conditions followed by recrystallization from CHCl3/CH3OHto give the target compound H2TPHEP (2) (152 mg, 20%). The MS and 1H NMR spectra of porphyrin 2 were shown in Fig. S2 andFig. S3. H NMR (300 Hz, 25 C, TMS): delta = 8.98 (8H, beta-pyrrole), 8.60(4H, phenanthrene), 8.58 (4H, phenanthrene), 8.05 (4H, phenanthrene),7.89 (4H, phenanthrene), 7.62 (4H, phenanthrene), 7.24(8H, phenanthrene), -2.06 (s, 2H, NH); MS (MALDI-TOF): m/z = 1019.1 [calcd. for C76H46N4 (M+4)+ 1019.2].

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 2441 - 2447
[2]Dyes and Pigments,2017,vol. 142,p. 116 - 120
[3]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1161 - 1166

7
[ 2026-42-8 ]
[ 4707-71-5 ]
[ 80819-43-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1457 - 1459

8
[ 4707-71-5 ]
[ 74-89-5 ]
[ 76532-36-0 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 140 - 145

9
[ 4707-71-5 ]
[ 109-77-3 ]
[ 72731-15-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With aluminum oxide; In dichloromethane; at 20℃; for 24h;	General procedure: Into a solution of malononitrile (8.00 mmol) in methylene chloride(20 mL), aluminum trioxide (800 mg) and the appropriate aldehyde(4.00 mmol) were added. The reaction mixture was stirred at roomtemperature for 24 h. After this time, the crude product was purifiedusing column chromatography (SiO2, CH2Cl2). All compounds wereprepared according to the method described in our previous paper [24].

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 12778 - 12782
Angew. Chem.,2016,vol. 128,p. 12970 - 12974,5
[2]Dyes and Pigments,2020,vol. 180
[3]Journal of Physical Chemistry,1991,vol. 95,p. 5737 - 5742
[4]Chemical Science,2014,vol. 5,p. 677 - 684
[5]Dalton Transactions,2018,vol. 47,p. 9742 - 9754
[6]Catalysis Communications,2020,vol. 142

10
[ 4707-71-5 ]
[ 484-17-3 ]
[ 837-45-6 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 4464 - 4466

11
[ 4707-71-5 ]
[ 127410-76-8 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 5334 - 5337
[2]Tetrahedron Letters,1989,vol. 30,p. 6095 - 6096

12
[ 4707-71-5 ]
[ 100-46-9 ]
benzyl(9-phenanthrylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In ethanol;Reflux;	General procedure: Ph2SnCl2 was commercially available and was used without furtherpurification. The synthesis of benzyl(9-anthrylmethyl)amine,benzyl(9-phenanthrylmethyl)amine and benzyl(1-pyrenylmethyl)amine were carried out by condensation of 9-anthracenecarboxaldehyde,9-phenanthrenecarboxaldehyde and 1-pyrenecarboxaldehydewith benzylamine by heating under reflux in ethanolfollowed by Schiff bases reduction with NaBH4. The secondary amines 1-naphthylmethyl(1-pyrenylmethyl)amine and di(1-pyrenylmethyl)amine were carried out by condensation ofpyrenecarboxaldehyde, with 1-naphthylmethylamine and1-pyrenylmethylamine by heating under reflux in ethanol followedby Schiff bases reduction with NaBH4 [15]. The sodium dithiocarbamatesalts were prepared by treating of the secondary amineswith carbon disulfide and sodium hydroxide in methanol [16].The subsequent addition of diphenyltin dichloride leading to thecorresponding chlorodiphenyltin(IV) dithiocarbamate complexes[14]. The NMR studies were carried out with Varian Inova 400instruments. Chemical shifts (dH and dSn) are given in ppm. Standardreferences were used: TMS (dH = 0) and SnMe4 (d 119Sn = 0).The electronic absorption spectra were recorded at 25 C on aHewlet-Packard 8452A diode array spectrophotometer.

Reference： [1]Journal of Chemical Research - Part S,1996,p. 506 - 507
[2]Polyhedron,2016,vol. 111,p. 132 - 142

13
[ 4707-71-5 ]
[ 837-45-6 ]

Reference： [1]Journal of Physical Chemistry A,1998,vol. 102,p. 8679 - 8689
[2]Acta Crystallographica, Section C: Crystal Structure Communications,1997,vol. C53,p. 1265 - 1267

14
[ 4707-71-5 ]
(2R,3R)-2,3-Di-phenanthren-9-yl-oxirane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 4560 - 4564

15
[ 4707-71-5 ]
[ 95-54-5 ]
2-(phenanthren-9-yl)-1H-benzo[d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With bismuth (III) nitrate pentahydrate; In water; at 80℃; for 0.5h;Microwave irradiation; Green chemistry;	General procedure: The substrate (o-phenylenediamine, 1.0 mmol), aldehyde(1.1 mmol) and bismuth nitrate pentahydrate (24 mg, 5 mol%) were mixed together with water (1mL) in a microwave vial fitted with a magnetic stir bar.The mixture was irradiated in an automated microwave(CEM Corporation, Discover model) and the progressof the reaction was monitored by TLC. After completionof the reaction (Table 4) ethyl acetate (10 mL) wasadded to the reaction mixture and the organic layer waswashed with saturated sodium bicarbonate solution,brine and water successively. It was dried over anhydroussodium sulfate and the solvent was removed underreduced pressure. The crude mass was purifiedthrough a small silica gel column using ethyl acetate/hexanes as eluent.

Reference： [1]ACS Combinatorial Science,2016,vol. 18,p. 644 - 650
[2]Current Medicinal Chemistry,2017,vol. 24,p. 4714 - 4725
[3]Bollettino Chimico Farmaceutico,2004,vol. 143,p. 110 - 115
[4]Patent: US2018/334459,2018,A1 .Location in patent: Paragraph 0081

16
[ 4707-71-5 ]
[ 134-81-6 ]
[ 13730-66-0 ]

Reference： [1]Green Chemistry,2010,vol. 12,p. 1018 - 1022
[2]Bollettino Chimico Farmaceutico,2004,vol. 143,p. 110 - 115

17
[ 104-92-7 ]
[ 4707-71-5 ]
[ 796874-03-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5269 - 5276
[2]European Journal of Medicinal Chemistry,2007,vol. 42,p. 410 - 419

18
[ 1078-28-0 ]
[ 141-43-5 ]
[ 4707-71-5 ]
1-(2-Amino-ethyl)-6-methoxy-2-((E)-2-phenanthren-9-yl-vinyl)-quinolinium [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 6331 - 6335

19
[ 4229-44-1 ]
[ 4707-71-5 ]
(Z)-C-(9-phenanthryl)-N-methyl nitrone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 709 - 715

20
[ 29601-98-7 ]
[ 4707-71-5 ]
(Z)-C-(9-phenanthryl)-N-benzyl nitrone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 709 - 715

21
[ 4707-71-5 ]
[ 88284-48-4 ]
[ 221557-49-9 ]
{2-[bis(2-methoxyethyl)amino]phenyl}(phenanthren-9-yl)methanol [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 3367 - 3370

22
[ 90965-06-3 ]
[ 4707-71-5 ]
[ 32870-98-7 ]

Reference： [1]Synlett,2007,p. 3037 - 3041

23
[ 837-45-6 ]
[ 4707-71-5 ]

Reference： [1]Journal of the American Chemical Society,1933,vol. 55,p. 2995,2996

24
[ 110-89-4 ]
[ 13121-99-8 ]
[ 4707-71-5 ]
2-(4-Pyridyl)-3-(9-phenanthryl)-2-propenenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	In ethanol	9 2-(4-Pyridyl)-3-(9-phenanthryl)-2-propenenitrile Example 9 2-(4-Pyridyl)-3-(9-phenanthryl)-2-propenenitrile To a solution of 0.5 g (2.43 mmol) phenanthrene-9-carboxaldehyde in 40 ml absolute ethanol was added 0.375 g (2.43 mmol) 4-pyridylacetonitrile. HCl and 0.5 ml piperidine, and the reaction mixture was stirred and heated to reflux for 2 hours, at which time a yellow precipitate had formed. The reaction mixture was heated to reflux for an additional 2 hours, cooled to room temperature, and the solvent was partially evaporated. The mixture was partitioned between CH2 Cl2 and H2 O, washed with 5% NaHCO3, dried over anhydrous Na2 SO4, filtered, concentrated to give a yellow solid which was then flash chromatographed on silica gel. The material was loaded onto the column with CH2 Cl2 and eluted with EtOAc:hexane (1:1) to give 0.328 g (44% yield) of product as an amorphous yellow solid, m.p. 206°-208°.

Reference： [1]Current Patent Assignee: Yissum Research & Development (in: Hebrew University); HEBREW UNIVERSITY OF JERUSALEM - US5196446, 1993, A

25
[ 2142-63-4 ]
[ 4707-71-5 ]
[ 890148-76-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; In acetic acid; at 100℃; for 5h;	9-Phenanthrenecarboxyaldehyde (4.29 g), 3'-bromoacetophenone (8.28 g), ammonium acetate (20.5 g), and acetic acid (52 ml) were stirred in air at 100C for 5 hr, and the supernatant was removed. Methanol was added thereto for washing the remaining viscous liquid. After the removing of the washings, the viscous liquid was purified by silica-gel column chromatography and suspension washing with methanol and then dried by heating under reduced pressure to obtain a target compound 9 (3.00 g).

Reference： [1]Patent: EP1820801,2007,A1 .Location in patent: Page/Page column 81; 82

26
[ 1558-17-4 ]
[ 4707-71-5 ]
[ 1154425-59-8 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 3711 - 3717

27
[ 636562-72-6 ]
[ 4707-71-5 ]
C₇₆H₆₀N₁₁O₂P₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In methanol; at 50℃; for 6h;	General procedure: The phosphorus hydrazones 1a-8c were synthesized by the following literature methods.[8], [9] and [15] Quantitative amount of phosphorus hydrazide in MeOH (15 mL) was added dropwise to the solution of corresponding fluorophore-containing carboxaldehyde in hot MeOH (30 mL). The reaction mixture was stirred at 50 C for 6 h. The yellow precipitate obtained was filtered, washed with hot methanol (2×5 mL) and recrystallized from a 1:1 mixture of CH2Cl2/n-hexane at 0 C.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6917 - 6926

28
[ 56634-22-1 ]
[ 4707-71-5 ]
C₄₈H₃₉N₆OP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In methanol; at 50℃; for 6h;	General procedure: The phosphorus hydrazones 1a-8c were synthesized by the following literature methods.[8], [9] and [15] Quantitative amount of phosphorus hydrazide in MeOH (15 mL) was added dropwise to the solution of corresponding fluorophore-containing carboxaldehyde in hot MeOH (30 mL). The reaction mixture was stirred at 50 C for 6 h. The yellow precipitate obtained was filtered, washed with hot methanol (2×5 mL) and recrystallized from a 1:1 mixture of CH2Cl2/n-hexane at 0 C.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6917 - 6926

29
[ 56634-23-2 ]
[ 4707-71-5 ]
C₄₈H₃₉N₆PS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In methanol; at 50℃; for 6h;	General procedure: The phosphorus hydrazones 1a-8c were synthesized by the following literature methods.[8], [9] and [15] Quantitative amount of phosphorus hydrazide in MeOH (15 mL) was added dropwise to the solution of corresponding fluorophore-containing carboxaldehyde in hot MeOH (30 mL). The reaction mixture was stirred at 50 C for 6 h. The yellow precipitate obtained was filtered, washed with hot methanol (2×5 mL) and recrystallized from a 1:1 mixture of CH2Cl2/n-hexane at 0 C.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6917 - 6926

30
[ 70629-50-4 ]
[ 4707-71-5 ]
C₂₈H₂₃N₂OP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In methanol; at 50℃; for 6h;	General procedure: The phosphorus hydrazones 1a-8c were synthesized by the following literature methods.[8], [9] and [15] Quantitative amount of phosphorus hydrazide in MeOH (15 mL) was added dropwise to the solution of corresponding fluorophore-containing carboxaldehyde in hot MeOH (30 mL). The reaction mixture was stirred at 50 C for 6 h. The yellow precipitate obtained was filtered, washed with hot methanol (2×5 mL) and recrystallized from a 1:1 mixture of CH2Cl2/n-hexane at 0 C.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6917 - 6926

31
[ 54529-67-8 ]
[ 4707-71-5 ]
C₃₈H₃₁N₄OP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In methanol; at 50℃; for 6h;	General procedure: The phosphorus hydrazones 1a-8c were synthesized by the following literature methods.[8], [9] and [15] Quantitative amount of phosphorus hydrazide in MeOH (15 mL) was added dropwise to the solution of corresponding fluorophore-containing carboxaldehyde in hot MeOH (30 mL). The reaction mixture was stirred at 50 C for 6 h. The yellow precipitate obtained was filtered, washed with hot methanol (2×5 mL) and recrystallized from a 1:1 mixture of CH2Cl2/n-hexane at 0 C.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6917 - 6926

32
[ 4707-71-5 ]
hexa(N₁-methylhydrazino)cyclo(triphosphazene) [ No CAS ]
C₉₆H₇₈N₁₅P₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In methanol; at 50℃; for 6h;	General procedure: The phosphorus hydrazones 1a-8c were synthesized by the following literature methods.[8], [9] and [15] Quantitative amount of phosphorus hydrazide in MeOH (15 mL) was added dropwise to the solution of corresponding fluorophore-containing carboxaldehyde in hot MeOH (30 mL). The reaction mixture was stirred at 50 C for 6 h. The yellow precipitate obtained was filtered, washed with hot methanol (2×5 mL) and recrystallized from a 1:1 mixture of CH2Cl2/n-hexane at 0 C.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6917 - 6926

33
[ 4707-71-5 ]
1,1,3,3-bis[spiro-2',2''-dioxy-1',1''-biphenyl]-5,5-bis(1-methylhydrazido)-1,3,5,2,4,6-cyclotriphosphazene [ No CAS ]
C₅₆H₄₂N₇O₄P₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In methanol; at 50℃; for 6h;	General procedure: The phosphorus hydrazones 1a-8c were synthesized by the following literature methods.[8], [9] and [15] Quantitative amount of phosphorus hydrazide in MeOH (15 mL) was added dropwise to the solution of corresponding fluorophore-containing carboxaldehyde in hot MeOH (30 mL). The reaction mixture was stirred at 50 C for 6 h. The yellow precipitate obtained was filtered, washed with hot methanol (2×5 mL) and recrystallized from a 1:1 mixture of CH2Cl2/n-hexane at 0 C.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6917 - 6926

34
[ 4707-71-5 ]
[ 85-01-8 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 4253 - 4255
[2]European Journal of Organic Chemistry,2017,vol. 2017,p. 4168 - 4174

35
[ 162662-27-3 ]
[ 4707-71-5 ]
(R)-(4-(methoxymethoxy)phenyl)(phenanthren-9-yl)methanol [ No CAS ]
(S)-(4-(methoxymethoxy)phenyl)(phenanthren-9-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(methoxymethoxy)phenylboronic acid With diethylzinc In toluene at 60℃; for 12h; Inert atmosphere; Stage #2: With (S)-α,α-diphenyl-1-(triphenylmethyl)-2-aziridinemethanol In toluene at 20℃; for 0.25h; Inert atmosphere; Stage #3: Phenanthrene-9-carboxaldehyde In toluene at 20℃; for 12h; Inert atmosphere; optical yield given as %ee;

Reference： [1]Taylor, Buck L. H.; Harris, Michael R.; Jarvo, Elizabeth R. [Angewandte Chemie - International Edition, 2012, vol. 51, # 31, p. 7790 - 7793]

36
[ 504-29-0 ]
[ 14542-93-9 ]
[ 4707-71-5 ]
[ 1401520-48-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogenchloride; In 1,4-dioxane; acetonitrile; at 110℃; for 0.333333h;Microwave irradiation;	General procedure: To the solution of 2-aminopyridine (24 mg, 0.25 mmol) in anhydrous acetonitrile, were added benzaldehyde (28 muL, 0.28 mmol), a catalytic amount of 4 N HCl/dioxane (10 muL) and tert-butyl isonitrile (27 muL, 0.24 mmol). The reaction mixture was then heated under microwave conditions (400 W, 110 C, 20 min). After the reaction mixture was cooled to room temperature, solvent was removed and the residue was purified using column chromatography to obtain the compound 1a as white solid (44 mg, 69%).

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5850 - 5863

37
[ 88-12-0 ]
[ 4707-71-5 ]
[ 62-53-3 ]
cis-4-(2-oxopyrrolin-1-yl)tetrahydroquinoline [ No CAS ]