161265-03-8|(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)| Ambeed

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Quality Control of [ 161265-03-8 ] Purity: 98% SDS Specification

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Product Citations Show More

Phosphine‐Ligated Cobalt (II) Acetylacetonate Complexes

Jayawardhena, JPI Dulmini ; Krause, Jeanette A ; Guan, Hairong ;

DOI: 10.1002/ejic.202500157 Eur. J. Inorg. Chem.,2025,e202500157.

Abstract: Cobalt(II) acetylacetonate complexes bearing a phosphine ligand can be key intermediates or precursors to cobalt-based catalysts; however, they have been rarely studied, especially from the molecular structure point of view. This work is focused on the understanding of how different phosphines react with Co(acac)₂ (acac = acetylacetonate). To do so, a variety of analytical tools including NMR and IR spectroscopy, X-ray crystallography, mass spectrometry, and elemental analysis have been used to study the reactions and characterize the isolated products. These results have shown that the monodentate ligand, HPPh₂, binds to Co(acac)₂ weakly and reversibly to produce Co₂(acac)₄(HPPh₂), whereas the bidentate ligand, 1,2-bis(diphenylphosphino)ethane (dppe), interacts with Co(acac)₂ more strongly to yield a one-dimensional coordination polymer of Co(acac)₂(dppe). 2-(Dicyclohexylphosphino)methyl-1Hpyrrole (^CyPN^H), which is a pyrrole-tethered phosphine, forms an unusual 5-coordinate cobalt complex, Co(acac)₂(^CyPN^H), in which the pyrrole moiety participates in a bifurcated hydrogen-bonding interaction with the [acac] – ligands. In contrast, another bidentate ligand, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos), fails to react with Co(acac)₂, presumably due to its wide bite angle and difficulty in bridging two metals.

Keywords: Cobalt ; Phosphines ; Acetylacetonate Complexes ; Paramagnetic NMR ; Clusters

Purchased from AmBeed: 1663-45-2 ; 161265-03-8 ; 14024-48-7

Synthetic Elaboration of β-Carbonyl Alkylboronic Esters

Hamilton, Mason D ;

Abstract: Organoboron compounds are some of the most synthetically versatile compounds in organic chemistry due to the many valuable transformations of the C-B bond. This synthetic versatility combined with the pharmacophoric nature of carboxylic acids has led to an increased interest in the one-pot difunctionalization of vinyl arenes using CO₂ and pinacol boranes. Recently, much progress has been made to improve the scope and versatility of boracarboxylation reactions to now include electron-deficient and α-methyl substituted vinyl arenes. However, the potential transformations of boracarboxylated products have remained unexplored. Here, methodologies to transform the β-aryl alkylboronic ester into new C-C, C-N, and C-X bonds will be described. Medically relevant 2,3-diarylpropionic acids can now be accessed via a two-step protocol consisting of boracarboxylation of a vinyl arene followed by a palladium(0)-catalyzed Suzuki cross-coupling. This methodology provides access to both the α- and β-regioisomers independently whereas traditional strategies to access these compounds afford only one regioisomer, and in most cases, a mixture of regioisomers. Interesting biaryl and heterocyclic products can be accessed and to demonstrate the synthetic utility of this protocol, a glucagon receptor antagonist was synthesized in 4 less steps than the previously reported method while maintaining similar yields. The transformative capability of boracarboxylated products is further demonstrated through a base-_x005f_x0002_and external oxidant-free copper(II)-catalyzed amination to generate β²-amino acid derivatives. While the β-carboxylic acid was intolerable to the conditions, protection via esterification or amidation allowed for successful amination of the alkylboronic ester to occur. Amination of two bora-NSAIDs, bora-ibuprofen and bora-naproxen, was successful and a number of cyclic and acyclic amines are suitable for the transformation. Preliminary mechanistic work suggests that this amination does not proceed through a free-radical intermediate but rather a two-electron pathway. Finally, a novel halogenation of boracarboxylated products is achieved to generate the corresponding β-aryl alkyl halides. This methodology is performed in a base, metal, and additive free manner that utilizes cheap and readily available sources of electrophilic halide. Both bromination and iodination are demonstrated and can be achieved on a variety of electron-rich and electron-poor boracarboxylated products and can subsequently undergo amination to provide an alternative route to β²-amino acid derivatives. Mechanistic experiments suggest that the β-carboxylic acid is required to achieve the activation of the C-B bond. Radical trapping experiments also indicate that this transformation may occur through the formation of an alkyl radical although this is unlikely.

Keywords: Boracarboxylation ; alkylboronic ester ; Suzuki cross-coupling ; oxidative amination ; 2,3-diarylpropionic acid ; β²-amino acid

Purchased from AmBeed: 161265-03-8 ; 73183-34-3 ; 128-37-0 ; 1122-58-3 ; 1416881-52-1

Product Details of [ 161265-03-8 ]

CAS No. :	161265-03-8
Formula :	C₃₉H₃₂OP₂
M.W :	578.62
SMILES Code :	CC1(C)C2=C(OC3=C1C=CC=C3P(C4=CC=CC=C4)C5=CC=CC=C5)C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C2
MDL No. :	MFCD00233866
InChI Key :	CXNIUSPIQKWYAI-UHFFFAOYSA-N
Pubchem ID :	636044

Safety of [ 161265-03-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 161265-03-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	42
Num. arom. heavy atoms	36
Fraction Csp3	0.08
Num. rotatable bonds	6
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	182.88
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	36.41 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	5.48
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	9.7
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	7.63
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	7.77
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	11.07
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	8.33

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-9.78
Solubility	0.0000000968 mg/ml ; 0.0000000002 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-10.38
Solubility	0.000000024 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-15.7
Solubility	0.0 mg/ml ; 1.98e-16 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-2.94 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	2.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.17

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	5.68

Application In Synthesis of [ 161265-03-8 ]

* 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.

Upstream synthesis route of [ 161265-03-8 ]
Downstream synthetic route of [ 161265-03-8 ]

[ 161265-03-8 ] Synthesis Path-Upstream 1~4

1
[ 21264-30-2 ]
[ 161265-03-8 ]
[ 205319-10-4 ]

References: [1] Organic Syntheses, 2016, vol. 93, p. 341 - 351.
[2] Organic Syntheses, 2016, vol. 93, p. 341 - 351.
[3] Journal of the American Chemical Society, 2015, vol. 137, # 39, p. 12490 - 12493.

2
[ 15617-18-2 ]
[ 161265-03-8 ]
[ 205319-10-4 ]

References: [1] European Journal of Inorganic Chemistry, 1998, # 2, p. 155 - 157.

3
[ 161265-03-8 ]
[ 205319-10-4 ]

References: [1] Journal of Organometallic Chemistry, 2012, vol. 696, # 26, p. 4293 - 4297.

4
[ 1435520-65-2 ]
[ 161265-03-8 ]
[ 1445085-97-1 ]

References: [1] Chemical Science, 2013, vol. 4, # 3, p. 916 - 920.

[ 161265-03-8 ] Synthesis Path-Downstream 1~14

1
[ 55186-89-5 ]
[ 589-87-7 ]
[ 161265-03-8 ]
[ 477740-02-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	With caesium carbonate;palladium diacetate; In 1,4-dioxane;	Part A. 1-Benzyl-4-(4-bromo-phenyl)-[1,4]diazepan-5-one: Commercially available <strong>[55186-89-5]1-benzyl-(1,4)-diazepan-5-one</strong> (14.7 mmol), p-bromoiodobenzene (1 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.15 eq), cesium carbonate (1.5 eq), and palladium acetate (0.1 eq) were placed in a round bottom flask and it was evacuated and flushed 3* with nitrogen. To this mixture was then added 200 mL of dioxane and the resulting solution was again evacuated and flushed 3* times with nitrogen gas. The mixture was allowed to stir at 75 C. overnight during which time the mixture turned from brown to bright yellow suspension. The mixture was cooled and diluted with dichloromethane and then was filtered through a pad of celite. The filtrate was removed under reduced pressure and the residue was purified by flash column chromatography eluding with 50% EtOAc/Hex to give compound 1 as an off-white solid (63%). Mass spectrum, ESI (M+H) 359.3, 361.3.

References: [1]Patent: US2002/183324,2002,A1 .

2
[ 33893-89-9 ]
tetrakis(acetonitrile)copper(I)tetrafluoroborate [ No CAS ]
[ 161265-03-8 ]
[Cu(9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene)(2-(tetrazol-5-yl)pyridine)]BF₄ [ No CAS ]

References: [1]Chemical Communications,2013,vol. 49,p. 6501 - 6503.

3
[ 33893-89-9 ]
[ 161265-03-8 ]
[ 1445903-73-0 ]

References: [1]Chemical Communications,2013,vol. 49,p. 6501 - 6503.

4
[ 52522-40-4 ]
[ 591-50-4 ]
[ 161265-03-8 ]
[(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)palladium(II)(phenyl)iodine] [ No CAS ]

References: [1]Chemistry - An Asian Journal,2015,vol. 10,p. 321 - 324.

5
tetrakis(acetonitrile)copper(I)tetrafluoroborate [ No CAS ]
[ 17217-57-1 ]
[ 161265-03-8 ]
C₅₁H₄₄CuN₂O₃P₂⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 5477 - 5481.
Angew. Chem.,2018,vol. 130,p. 5575 - 5579,5.

6
[ 52522-40-4 ]
[ 161265-03-8 ]
p-anisoyl iodide [ No CAS ]
(Xantphos)Pd(CO(C₆H₄OCH₃))(I) [ No CAS ]