[ CAS No. 144970-30-9 ] {[proInfo.proName]}

Name: 144970-30-9|1,3,5,7-Tetrakis(4-iodophenyl)adamantane|97%
Brand: Ambeed
SKU: A579769
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Quality Control of [ 144970-30-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 144970-30-9 ]

Product Details of [ 144970-30-9 ]

CAS No. :	144970-30-9	MDL No. :	MFCD30187648
Formula :	C₃₄H₂₈I₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HTGPRXPCTBXRBH-UHFFFAOYSA-N
M.W :	944.20	Pubchem ID :	12963667
Synonyms :

Calculated chemistry of [ 144970-30-9 ]

Physicochemical Properties

Num. heavy atoms :	38
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.29
Num. rotatable bonds :	4
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	192.19
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	5.88
Log Po/w (XLOGP3) :	12.43
Log Po/w (WLOGP) :	10.54
Log Po/w (MLOGP) :	10.3
Log Po/w (SILICOS-IT) :	12.56
Consensus Log Po/w :	10.34

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	3.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	-13.73
Solubility :	0.0 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (Ali) :	-12.45
Solubility :	0.0000000003 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-15.63
Solubility :	0.0 mg/ml ; 2.36e-16 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	5.58

Safety of [ 144970-30-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 144970-30-9 ]

* 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 [ 144970-30-9 ]

[ 144970-30-9 ] Synthesis Path-Downstream 1~75

1
[ 144970-30-9 ]
[ 1066-54-2 ]
1,3,5,7-tetrakis(4-trimethylsilyl-ethynylphenyl)adamantane [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 9805 - 9808
[2]Chemical Communications,1999,p. 173 - 174
[3]Tetrahedron,2015,vol. 71,p. 9519 - 9527
[4]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743
[5]Chemistry - A European Journal,2013,vol. 19,p. 11590 - 11597

2
[ 908094-01-9 ]
[ 124-38-9 ]
[ 144970-30-9 ]
[ 1066-54-2 ]
[ 312329-45-6 ]
C₄₈H₅₂O₄Si₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 7419 - 7421

3
[ 100-42-5 ]
[ 144970-30-9 ]
tetra(4-styryl-phenyl)adanantane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 5695 - 5709

4
[ 183051-50-5 ]
[ 144970-30-9 ]
tetrakis(4-tert-butylstyrylstilbenyl)adamantane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 5695 - 5709

5
[ 64-17-5 ]
[ 124-38-9 ]
[ 144970-30-9 ]
[ 1066-54-2 ]
[ 312329-43-4 ]
C₅₀H₅₆O₄Si₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 7419 - 7421

6
[ 124-38-9 ]
[ 144970-30-9 ]
[ 1066-54-2 ]
[ 312329-39-8 ]
C₄₆H₄₈O₄Si₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 7419 - 7421

7
[ 144970-30-9 ]
[ 1066-54-2 ]
[ 312329-37-6 ]
1,5-bis-(4-iodo-phenyl)-3,7-bis-(4-trimethylsilanylethynyl-phenyl)-adamantane [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 7419 - 7421

8
[ 16004-75-4 ]
[ 144970-30-9 ]

Yield	Reaction Conditions	Operation in experiment
33.9%	With <bis(trifluoroacetoxy)iodo>benzene; iodine; In chloroform; at 20℃; for 24h;Inert atmosphere;	Under a nitrogen atmosphere, 15.6 g (35.4 mmol) of the compound M-3, 30.4 g (70.4 mmol) of bis (trifluoroacetoxy) iodobenzene were added to a chloroform suspension (389 mL) of iodine 17.9 g (70.8 mmol) 8 mmol), and the mixture was stirred at room temperature for 6 hours, 15.2 g (35.4 mmol) of bis (trifluoroacetoxy) iodobenzene was added, and the mixture was stirred at room temperature for 18 hours.After stirring, filtration, the filtrate was washed with 5% sodium bisulfite aqueous solution, distilled water and saturated brine, concentrated under reduced pressure, purified by column (silica gel · hexane: chloroform) and washed at 40 C. for 3 days , And dried under reduced pressure at 60 C. for 2 days to obtain 11.3 g (12.0 mmol) of Compound M-4 as a white solid.Yield 33.9%.Based on the following data, it was identified as a target compound.1H-NMR (400MHz, dimethyl sulfoxide -d6): δ (ppm) 2.0 (12H), 7.3 (8H), 7.6 (8H)
16%		To a solution of 1,3,5,7-tetraphenyladamantane (21; 2.0 g, 4.5 mmol) in anhyd CHCl3 (50 mL) was added I2 (2.36 g, 9.0 mmol). The reaction mixture was stirred at RT for 1 h under N2. Then bis(trifluoroacetoxy) iodobenzene (3.9 g, 9.0 mmol) was added and the mixture was stirred for 24 h at RT under N2. The mixture was filtered to remove the solid and the filter cake was washed with CHCl3 (100 mL). The combined filtrates were washed with aq 5% NaHSO3 (100 mL), followed by H2O (100 mL) and brine (100 mL). The organic layer was dried (anhyd Na2SO4) and concentrated. The residue was purified by column chromatography (PE/CH2Cl2 5:1); yield: 697 mg (16%); white solid. 1H NMR (300 MHz, CDCl3): = 7.67-7.64 (d, J = 8.4 Hz, 8 H), 7.19-7.16 (d, J = 8.7 Hz, 8 H), 2.05 (s, 12 H). 13C NMR (125 MHz, CDCl3): = 148.5, 137.6, 127.2, 91.8, 46.7, 39.1.22

Reference： [1]Synthesis,2007,p. 3323 - 3328
[2]Chemistry - A European Journal,2013,vol. 19,p. 11590 - 11597
[3]CrystEngComm,2021,vol. 23,p. 8169 - 8182
[4]Crystal Growth and Design,2012,vol. 12,p. 3792 - 3798
[5]Journal of Materials Chemistry A,2016,vol. 4,p. 8190 - 8197
[6]Journal of Organic Chemistry,2014,vol. 79,p. 8313 - 8323
[7]Organic letters,2002,vol. 4,p. 3631 - 3634
[8]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743
[9]Tetrahedron,2015,vol. 71,p. 9519 - 9527
[10]Patent: JP5830967,2015,B2 .Location in patent: Paragraph 0123; 0125
[11]Synthesis,2022,vol. 54,p. 1643 - 1651
[12]CrystEngComm,2013,vol. 15,p. 1235 - 1243
[13]Chemical Communications,2015,vol. 51,p. 9805 - 9808
[14]New Journal of Chemistry,2018,vol. 42,p. 12802 - 12810

9
[ 144970-30-9 ]
[ 476182-61-3 ]
tetrakis-{4-(4-[(5-[1,2,5]dithiazepanyl)phenyl]ethynyl)phenyl}adamantane [ No CAS ]

Reference： [1]Organic letters,2002,vol. 4,p. 3631 - 3634

10
[ 144970-30-9 ]
[ 1066-54-2 ]
[ 312329-37-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3655 - 3664
[2]Journal of the American Chemical Society,2002,vol. 124,p. 7801 - 7811

11
[ 100-43-6 ]
[ 144970-30-9 ]
1,3,5,7-tetrakis(4-((E)-2-(pyridin-4-yl)vinyl)phenyl)adamantane [ No CAS ]

Reference： [1]Journal of Molecular Structure,2003,vol. 656,p. 27 - 35

12
[ 3034-86-4 ]
[ 144970-30-9 ]
[ 562823-77-2 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 4862 - 4869

13
[ 544-92-3 ]
[ 144970-30-9 ]
[ 167013-23-2 ]

Reference： [1]Organic Preparations and Procedures International,2004,vol. 36,p. 353 - 359

14
[ 908094-01-9 ]
[ 124-38-9 ]
[ 144970-30-9 ]
1-phenyl-3,4,7-tris(4-carbomethoxyphenyl)adamantane [ No CAS ]
[ 777063-01-1 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 4895 - 4899

15
[ 64-19-7 ]
[ 144970-30-9 ]
1,3,5,7-tetrakis-(4-(diacetoxyiodo)phenyl)adamantane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 100%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 12h;	To a stirred solution of 1,3,5,7-tetrakis(4-iodophenyl)-adamantane 2 (1.42 g, 1.5 mmol) in dichloromethane (150 mL)-acetic acid (150 mL) was added mCPBA (ca. 69% purity,3.12 g, 18 mmol) at room temperature. The mixture was stirred for 12 h under the same reaction conditions during which the cloudy solution became clear. The resultant mixture was filtered, and dichloromethane was removed using a rotary evaporator. Hexane was added to the residue to precipitate the 1,3,5,7-tetrakis[4-(diacetoxyiodo)phenyl] adamantane 1a. After filtration, the almost pure product was obtained in nearly quantitative yield.
Ca. 100%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 12h;	To a stirred solution of <strong>[144970-30-9]1,3,5,7-<strong>[144970-30-9]tetrakis(4-iodophenyl)adamantane</strong></strong> 2 (1.42 g, 1.5 mmol) in CH2Cl2 (150 mL)-acetic acid (150 mL) was added mCPBA (ca. 69% purity, 3.12 g, 18 mmol) at room temperature. The mixture was stirred for 12 h under the same reaction conditions during which the cloudy solution became clear. The resultant mixture was filtered, and CH2Cl2 was removed using a rotary evaporator. Hexane was added to the residue to precipitate the 1,3,5,7-tetrakis[4-(diacetoxyiodo)phenyl]adamantane 1a. After filtration, the almost pure product was obtained in nearly quantitative yield.

Reference： [1]Chemical and Pharmaceutical Bulletin,2015,vol. 63,p. 819 - 824
[2]Heterocycles,2018,vol. 97,p. 632 - 645
[3]Angewandte Chemie - International Edition,2004,vol. 43,p. 3595 - 3598
[4]Journal of Organic Chemistry,2007,vol. 72,p. 109 - 116
[5]Chemical and Pharmaceutical Bulletin,2006,vol. 54,p. 1608 - 1610
[6]Green Chemistry,2012,vol. 14,p. 1493 - 1501
[7]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 710 - 713

16
1,3,5,7-tetrakis[4-{hydroxy(tosyloxy)iodo}phenyl]adamantane [ No CAS ]
[ 103-81-1 ]
[ 14613-34-4 ]
[ 144970-30-9 ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 3595 - 3598

17
1,3,5,7-tetrakis[4-{hydroxy(tosyloxy)iodo}phenyl]adamantane [ No CAS ]
[ 93-55-0 ]
[ 87456-64-2 ]
[ 144970-30-9 ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 3595 - 3598

18
[ 768-90-1 ]
[ 2712-78-9 ]
[ 144970-30-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3655 - 3664
[2]Angewandte Chemie - International Edition,2004,vol. 43,p. 3595 - 3598

19
6-ethynyl-2,2'-bis-methoxymethoxy-[1,1']binaphthalenyl [ No CAS ]
[ 144970-30-9 ]
C₁₃₈H₁₁₂O₁₆ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 6362 - 6366

20
1,3,5,7-tetrakis-[4-(bis(trifluoroacetoxy)iodo)phenyl]adamantane [ No CAS ]
[ 144970-30-9 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 109 - 116

Yield	Reaction Conditions	Operation in experiment
		[1]-(2) Synthesis of 1,3,5,7-tetrakis(4-iodophenyl)adamantane (Compound 2) Put into a mortar were 120.0 g (0.045 mole) of the compound synthesised in [1]-(1) described above and 23.0 g (0.090 mole) of iodine, and they were sufficiently crushed and blended with a pestle. The resulting pink powder was put into an Erlenmeyer flask of 500 ml, and 200 ml of chloroform was added thereto, followed by stirring the solution at room temperature under nitrogen flow. Added thereto was 39.0 g (0.090 mole) of [bis(trifluoroacetoxy)iodo]benzene, and the solution was stirred for 4 hours. The reaction solution was filtered, and the resulting solid matter was suspended in 300 ml of chloroform and stirred for one hour under refluxing. The solution was filtered while it was hot to remove the insoluble raw materials. The whole filtrates were put together and washed twice with a 5% sodium thiosulfate solution and twice with refined water.

22
[ 762-04-9 ]
[ 144970-30-9 ]
tetrakis-1,3,5,7-(4-diethylphosphonatophenyl)adamantane [ No CAS ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 3507 - 3514

23
[ 10602-06-9 ]
[ 144970-30-9 ]
1-(4-iodophenyl)-3,5,7-tris[4-(3-carbomethoxyphenylethynyl)phenyl]adamantane [ No CAS ]
C₅₄H₄₂I₂O₄ [ No CAS ]
C₇₄H₅₆O₈ [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 7550 - 7559

24
[ 144970-30-9 ]
[ 862420-30-2 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 4895 - 4899

25
[ 144970-30-9 ]
C₄₉H₃₈O₆ [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 4895 - 4899

26
[ 144970-30-9 ]
1,3,5,7-tetrakis(4-(chlorocarbonyl)phenyl)adamantane [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2004,vol. 36,p. 353 - 359
[2]Journal of Materials Chemistry A,2016,vol. 4,p. 8190 - 8197

27
[ 144970-30-9 ]
[ 154694-31-2 ]

Reference： [1]Organic Preparations and Procedures International,2004,vol. 36,p. 353 - 359
[2]Journal of Materials Chemistry A,2016,vol. 4,p. 8190 - 8197

28
[ 144970-30-9 ]
C₄₆H₅₂N₄O₄ [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2004,vol. 36,p. 353 - 359

29
[ 144970-30-9 ]
C₅₄H₆₈N₄O₄ [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2004,vol. 36,p. 353 - 359

30
[ 768-90-1 ]
[ 144970-30-9 ]

Reference： [1]Organic letters,2002,vol. 4,p. 3631 - 3634
[2]Chemistry - A European Journal,2013,vol. 19,p. 11590 - 11597
[3]Chemical Communications,2015,vol. 51,p. 9805 - 9808
[4]Journal of Organic Chemistry,2014,vol. 79,p. 8313 - 8323
[5]Tetrahedron,2015,vol. 71,p. 9519 - 9527
[6]Journal of Materials Chemistry A,2016,vol. 4,p. 8190 - 8197

31
[ 71-43-2 ]
1,x-dichloro-octane [ No CAS ]
[ 144970-30-9 ]

Reference： [1]Organic letters,2002,vol. 4,p. 3631 - 3634

32
[ 144970-30-9 ]
[ 144970-32-1 ]

Reference： [1]Chemical Communications,1999,p. 173 - 174

33
[ 591-50-4 ]
[ 16004-75-4 ]
[ 144970-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; In chloroform;	EXAMPLE 13 1,3,5,7-Tetra(p-Iodophenyl)adamantane A 100-mL round-bottom flask was charged with 1,3,5,7-tetraphenyladamantane (1.00 g, 2.3 mmol), iodine (2.33 g, 9.2 mmol), bis-trifluoroacetoxy) iodobenzene (4.5 g, 10 mmol) and chloroform (20 mL). The mixture was stirred at room temperature for 25 minutes and then transferred to a separatory funnel and washed four times with distilled water. The organic layer was evaporated, and the remaining solid was washed with diethylether to get rid of the purple color. The solid was recrystallized from chloroform and carbon tetrachloride (3:1) to give 1,3,5,7-tetra(p-iodophenyl)adamantane (1.5 g, 1.6 mmol, 69%). 1 H NMR (CDCl3, 360 MHz): d 2.05 (12H), 7.17, 7.19, 7.65, 7.67 (AA'BB', 16H). 13 C NMR 148.40, 137.52, 127.11, 91.726 (aromatic), 46.67, 39.04 (aliphatic), FABMS m/z (M+944).

Reference： [1]Patent: US5347063,1994,A

34
[ 124-38-9 ]
[ 144970-30-9 ]
[ 1066-54-2 ]
C₄₀H₃₆O₂ [ No CAS ]
[ 1038588-46-3 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 4020 - 4025

35
[ 144970-30-9 ]
[ 620624-92-2 ]
[ 1003002-62-7 ]

Reference： [1]Synthesis,2007,p. 3323 - 3328

36
[ 144970-30-9 ]
[ 1000190-37-3 ]
[ 1000190-40-8 ]
[ 951240-73-6 ]
[ 1000190-42-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 3586 - 3588

37
[ 144970-30-9 ]
[ 951240-73-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 3586 - 3588

38
[ 557-21-1 ]
[ 144970-30-9 ]
[ 1066-54-2 ]
[ 1169516-57-7 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 2088 - 2095

39
[ 1105506-55-5 ]
[ 144970-30-9 ]
1,3,5,7-tetrakis[4-(4-{4-[4-bis(4-methoxyphenyl)hydroxymethyl]phenyl}phenyl-ethynyl)-phenyl]adammantane [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 4593 - 4608

40
[ 6165-69-1 ]
[ 144970-30-9 ]
[ 1287732-89-1 ]