[ CAS No. 2449-05-0 ] {[proInfo.proName]}

Name: 2449-05-0|Dibenzyl diazene-1,2-dicarboxylate|96%
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SKU: A160551
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Quality Control of [ 2449-05-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 2449-05-0 ]

CAS No. :	2449-05-0	MDL No. :	MFCD00016737
Formula :	C₁₆H₁₄N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	298.29	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 2449-05-0 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.12
Num. rotatable bonds :	8
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	78.52
TPSA :	77.32 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) :	-5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.29
Log Po/w (XLOGP3) :	3.94
Log Po/w (WLOGP) :	3.81
Log Po/w (MLOGP) :	3.37
Log Po/w (SILICOS-IT) :	3.29
Consensus Log Po/w :	3.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.05
Solubility :	0.0268 mg/ml ; 0.0000897 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.26
Solubility :	0.00163 mg/ml ; 0.00000545 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.19
Solubility :	0.00193 mg/ml ; 0.00000647 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.79

Safety of [ 2449-05-0 ]

Signal Word:	Danger	Class:	4.1
Precautionary Statements:	P210-P240-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P370+P378-P403+P233-P501	UN#:	1325
Hazard Statements:	H228-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2449-05-0 ]

* 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 [ 2449-05-0 ]
Downstream synthetic route of [ 2449-05-0 ]

[ 2449-05-0 ] Synthesis Path-Upstream 1~3

1
[ 5394-50-3 ]
[ 2449-05-0 ]

Reference： [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 9, p. 1970 - 1975
[2] Journal of the Chemical Society, 1952, p. 2089,2093
[3] Chemische Berichte, 1959, vol. 92, p. 1478
[4] Journal of the American Chemical Society, 2011, vol. 133, # 30, p. 11402 - 11405
[5] Chemistry Letters, 2018, vol. 47, # 2, p. 144 - 147

2
[ 501-53-1 ]
[ 2449-05-0 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 2089,2093
[2] Chemische Berichte, 1959, vol. 92, p. 1478
[3] Journal of the American Chemical Society, 2011, vol. 133, # 30, p. 11402 - 11405
[4] Chemistry Letters, 2018, vol. 47, # 2, p. 144 - 147

3
[ 2449-05-0 ]
[ 65632-62-4 ]

Reference： [1] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1209 - 1213
[2] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1209 - 1213
[3] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1209 - 1213
[4] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1209 - 1213
[5] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1209 - 1213

[ 2449-05-0 ] Synthesis Path-Downstream 1~37

1
[ 17277-59-7 ]
[ 2449-05-0 ]
[ 34804-21-2 ]

Reference： [1]Wilson,G.E.; Martin,J.H.E. [Journal of Organic Chemistry, 1972, vol. 37, # 15, p. 2510 - 2512]

2
[ 6651-36-1 ]
[ 2449-05-0 ]
dibenzyl N-(2-oxocyclohexyl)-N,N'-hydrazinedicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With silver trifluoromethanesulfonate In dichloromethane at 0℃; for 0.5h;
91%	Stage #1: 1-(Trimethylsilyloxy)cyclohexene; dibenzyl azodicarboxylate In dichloromethane at 0℃; for 0.5h; Stage #2: With hydrogen fluoride In tetrahydrofuran; dichloromethane at 20℃; for 1h;

Reference： [1]Kobayashi, Shu; Yamashita, Yasuhiro; Ishitani, Haruro [Chemistry Letters, 1999, # 4, p. 307 - 308]
[2]Yamashita; Ishitani; Kobayashi [Canadian Journal of Chemistry, 2000, vol. 78, # 6, p. 666 - 672]

3
[ 15933-07-0 ]
[ 2449-05-0 ]
C₂₂H₂₄N₂O₇ [ No CAS ]
C₂₂H₂₄N₂O₇ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 2420 - 2421

4
[ 774-05-0 ]
[ 2449-05-0 ]
dibenzyl 1-(1-(ethoxycarbonyl)-2-oxocycloheptyl)hydrazine-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With copper(II) bis(trifluoromethanesulfonate); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In dichloromethane

Reference： [1]Marigo, Mauro; Juhl, Karsten; Jorgensen, Karl Anker [Angewandte Chemie - International Edition, 2003, vol. 42, # 12, p. 1367 - 1369]

5
[ 2449-05-0 ]
[ 10488-87-6 ]
(+)-1-[(1S)-1-benzoyl-2-ethoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-dibenzyl ester [ No CAS ]
(-)-1-[(1R)-1-benzoyl-2-ethoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-dibenzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-3,3'-dibromo-1,1'-bi-2-naphthol; lithium hydroxide; In diethyl ether; at -23℃; for 24h;Inert atmosphere;	General procedure: To a suspension of (R)-3,3?-Br2-BINOL (3a, 22.2 mg, 0.05 mmol) and LiOH (12.0 mg, 0.5 mmol) in diethyl ether (1 mL) was added a diethyl ether solution of beta-keto ester 1 (0.25 M, 2 mL, 0.50 mmol) at 23 C under an argon atmosphere. The reaction mixture was cooled to the desired temperature, and then a solution of azodicarboxylate 2 in diethyl ether (0.525 M, 1 mL, 0.525 mmol) was added. The mixture was further stirred for 24 h at the same temperature. The reaction was quenched with aqueous saturated NH4Cl (5 mL), and the aqueous layer was extracted with ethyl acetate (3 × 10 mL). The combined organic layer was washed with brine (15 mL) and then dried over Na2SO4. Concentration and column chromatographic purification gave the corresponding adduct 4. The enantiomeric excess was determined by HPLC equipped with a chiral column.

Reference： [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 1367 - 1369
[2]Tetrahedron,2017,vol. 73,p. 5975 - 5982

6
[ 39207-65-3 ]
[ 2449-05-0 ]
N,N'-bis(benzyloxycarbonyl)-1-hydrazino-1-isobutyryl-cyclohexan-2-one [ No CAS ]
N,N'-bis(benzyloxycarbonyl)-1-hydrazino-1-isobutyryl-cyclohexan-2-one [ No CAS ]

Reference： [1]Synthesis,2005,p. 957 - 960

7
[ 10409-56-0 ]
[ 2449-05-0 ]
(R)-(+)-N,N'-bis(benzyloxycarbonyl)-1-hydrazino-1-methyl-2-oxo-2-phenylethylphosphonic acid diethyl ester [ No CAS ]
(S)-(-)-N,N'-bis(benzyloxycarbonyl)-1-hydrazino-1-methyl-2-oxo-2-phenylethylphosphonic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With zinc trifluoromethanesulfonate; (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In dichloromethane at 20℃; for 48h; Title compound not separated from byproducts;

Reference： [1]Bernardi, Luca; Zhuang, Wei; Jorgensen, Karl Anker [Journal of the American Chemical Society, 2005, vol. 127, # 16, p. 5772 - 5773]

8
[ 5044-52-0 ]
[ 2449-05-0 ]
[ 590-86-3 ]
(3R)-3-isopropyl-3,6-dihydropyridazine-1,2-dicarboxylic acid dibenzyl ester [ No CAS ]
(3S)-3-isopropyl-3,6-dihydropyridazine-1,2-dicarboxylic acid dibenzyl ester [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2678 - 2689

9
[ 2449-05-0 ]
[ 1119-16-0 ]
C₂₂H₂₆N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98 % ee	With acetic acid In dichloromethane at 20℃; for 1.25h; stereoselective reaction;

Reference： [1]Fan, Xinyuan; Sayalero, Sonia; Pericas, Miquel A. [Advanced synthesis and catalysis, 2012, vol. 354, # 16, p. 2971 - 2976,6] Fan, Xinyuan; Sayalero, Sonia; Pericas, Miquel A. [Advanced Synthesis and Catalysis, 2012, vol. 354, # 16, p. 2971 - 2976]

10
[ 2449-05-0 ]
[ 65632-62-4 ]

Reference： [1]Organic Process Research and Development,2013,vol. 17,p. 1209 - 1213
[2]Organic Process Research and Development,2013,vol. 17,p. 1209 - 1213
[3]Organic Process Research and Development,2013,vol. 17,p. 1209 - 1213
[4]Organic Process Research and Development,2013,vol. 17,p. 1209 - 1213
[5]Organic Process Research and Development,2013,vol. 17,p. 1209 - 1213

11
[ 2449-05-0 ]
[ 1540-29-0 ]
C₂₆H₃₂N₂O₇ [ No CAS ]

Reference： [1]ChemCatChem,2013,vol. 5,p. 3078 - 3085

12
[ 2449-05-0 ]
[ 611-10-9 ]
(S)-N,N'-bis(benzyloxycarbonyl)-1-hydrazino-2-oxocyclohexane-1-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 2-ethoxycarbonyl-1-cyclopentanone With C₄₅H₄₀N₄O₅ In tetrahydrofuran at -78℃; for 0.25h; Stage #2: dibenzyl azodicarboxylate In tetrahydrofuran for 5h; enantioselective reaction;
99%	With C₄₀H₂₈N₂O; zinc trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; enantioselective reaction;	General procedure for Zn-catalyzed enantioselective amination of 2. General procedure: (S)-1c (6.08 mg, 0.011 mmol) and Zn(OTf)2 (3.64 mg, 0.01 mmol) were placed in a flask under Ar atmosphere. Then, DCE (1 mL) was added and the resulting solution was stirred at room temperature for 30 min. To the reaction mixture, ethyl 2-oxocyclopentanecarboxylate (2a) (14.8 L,0.1 mmol) and diisopropyl azodicarboxylate (3a) (38.3 L, 0.2 mmol) was successively added. After stirring for 24 h at the same temperature, the reaction was directly purified by flash column chromatography (eluting with hexane) to afford the corresponding product 4a as a colorless oil in 94% yield and with 87% ee.
93 %Spectr.	With C₄₈H₄₆N₄O₄; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 0℃; for 16h; enantioselective reaction;

Reference： [1]Gao, Yongzhi; Liu, Bin; Zhou, Hai-Bing; Wang, Wei; Dong, Chune [RSC Advances, 2015, vol. 5, # 31, p. 24392 - 24398]
[2]Naganawa, Yuki; Komatsu, Hiroyuki; Nishiyama, Hisao [Chemistry Letters, 2015, vol. 44, # 12, p. 1652 - 1654]
[3]Torres, Maria; Maisse-Francois, Aline; Bellemin-Laponnaz, Stephane [ChemCatChem, 2013, vol. 5, # 10, p. 3078 - 3085]

13
[ 4744-08-5 ]
[ 2449-05-0 ]
dibenzyl (S)-1-(1-methyl-2-hydroxyethyl)hydrazine-1,2-dicarboxylate [ No CAS ]
dibenzyl (R)-1-(1-methyl-2-hydroxyethyl)hydrazine-1,2-dicarboxylate [ No CAS ]