[ CAS No. 17746-05-3 ] {[proInfo.proName]}

Name: 17746-05-3|Undecanoylchloride|98%
Brand: Ambeed
SKU: A729736
Rating: 95 (32 reviews)

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Quality Control of [ 17746-05-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 17746-05-3 ]

CAS No. :	17746-05-3	MDL No. :	MFCD00000739
Formula :	C₁₁H₂₁ClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JUKPJGZUFHCZQI-UHFFFAOYSA-N
M.W :	204.74	Pubchem ID :	87287
Synonyms :		Chemical Name :	Undecanoylchloride

Calculated chemistry of [ 17746-05-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.91
Num. rotatable bonds :	9
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.99
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.3
Log Po/w (XLOGP3) :	5.4
Log Po/w (WLOGP) :	4.28
Log Po/w (MLOGP) :	3.27
Log Po/w (SILICOS-IT) :	4.18
Consensus Log Po/w :	4.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.92
Solubility :	0.0248 mg/ml ; 0.000121 mol/l
Class :	Soluble
Log S (Ali) :	-5.51
Solubility :	0.000628 mg/ml ; 0.00000307 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.48
Solubility :	0.00676 mg/ml ; 0.000033 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	2.3

Safety of [ 17746-05-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 17746-05-3 ]

* 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 [ 17746-05-3 ]
Downstream synthetic route of [ 17746-05-3 ]

[ 17746-05-3 ] Synthesis Path-Upstream 1~4

1
[ 112-37-8 ]
[ 17746-05-3 ]

Reference： [1] Canadian Journal of Chemistry, 2008, vol. 86, # 1, p. 7 - 19
[2] Journal of Organic Chemistry, 2010, vol. 75, # 14, p. 4769 - 4777
[3] Journal of the Chemical Society, 1936, p. 284
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 23, p. 7671 - 7680
[5] Bulletin de la Societe Chimique de France, 1939, vol. <5>6, p. 507
[6] Annales Pharmaceutiques Francaises, 1958, vol. 16, p. 757,760, 762
[7] Journal of the Institute of Petroleum, 1952, vol. 38, p. 415,421
[8] Revue Roumaine de Chimie, 2001, vol. 46, # 8, p. 899 - 903
[9] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1987, vol. 23, # 7, p. 751 - 754[10] Khimiya Geterotsiklicheskikh Soedinenii, 1987, # 7, p. 915 - 918
[11] European Journal of Medicinal Chemistry, 1991, vol. 26, # 9, p. 953 - 960
[12] Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 161, p. 1 - 24
[13] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2608 - 2612
[14] Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 902 - 915
[15] Synthesis, 2001, # 6, p. 914 - 918
[16] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1849 - 1856
[17] Journal of Medicinal Chemistry, 2006, vol. 49, # 13, p. 3872 - 3887
[18] Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 25, p. 9357 - 9365
[19] Chemical Communications, 2005, # 25, p. 3198 - 3200
[20] Journal of Lipid Research, 2010, vol. 51, # 1, p. 42 - 52
[21] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 6, p. 3342 - 3349
[22] Chemistry and Physics of Lipids, 2011, vol. 164, # 2, p. 118 - 124
[23] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2357 - 2361
[24] Crystal Growth and Design, 2014, vol. 14, # 10, p. 4944 - 4954
[25] Journal of Lipid Research, 2015, vol. 56, # 10, p. 2029 - 2039
[26] Journal of Chemical Sciences, 2015, vol. 127, # 9, p. 1627 - 1635
[27] Chemistry and Physics of Lipids, 2016, vol. 201, p. 1 - 10
[28] Patent: CN106167506, 2016, A, . Location in patent: Paragraph 0087
[29] Acta Chimica Slovenica, 2017, vol. 64, # 3, p. 603 - 612

2
[ 2834-05-1 ]
[ 17746-05-3 ]

Reference： [1] Patent: EP331745, 1989, A1,

3
[ 79-37-8 ]
[ 112-37-8 ]
[ 17746-05-3 ]

Reference： [1] Patent: US5521192, 1996, A,

4
[ 17746-05-3 ]
[ 58-22-0 ]
[ 5949-44-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine In N,N-dimethyl-formamide at 0 - 20℃; for 1 h; Inert atmosphere	First, under nitrogen, 5g of testosterone and 25ml of N,N-dimethylformamide (DMF, solvent), as well as 5ml pyridine (pyridine, base) are well-mixed, and then, at 0-10 deg.C was added 4.6ml undecanoyl chloride, and react at room temperature for 1 hour. After completion of the reaction, 5ml of water was added and stirred for 1 hour and the precipitated product was filtered, and then rinsed under aqueous acetone and the product dried in vacuo at room temperature after to obtain 7.6g of testosterone undecyl acid, yield 96percent, HPLC: 98.26percent. And then the, re-crystallization step is undecyl Testosterone 120g 480ml of acetone was added and stirred until the whole solution, followed by addition of 180ml of water and stirred for 0.5 hours, filtered and washed with an aqueous solution of acetone and run through again after crystallization resulting undecyl acid testosterone S crystalline (Form S),

Reference： [1] Patent: CN105732754, 2016, A, . Location in patent: Paragraph 0024; 0025; 0026; 0027; 0028

[ 17746-05-3 ] Synthesis Path-Downstream 1~30

1
[ 112-37-8 ]
[ 17746-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	With caprolactam; thionyl chloride; In ethanol; at -5℃;	18.6 g (0.1 mol) of undecanoic acid was accurately weighed into a 250 mL three-necked flask,To the three-necked flask was added 50 mL of absolute ethanol and 2 g of the catalyst caprolactam,Then, 23.8 g (0.2 mol) of thaw chloride was distilled off,Dropping the speed of 1 drop / s,The acid chlorination reaction was carried out at -5 C ice bath,The reaction was monitored by thin layer chromatography (TLC)After the reaction of the starting material undecanoic acid is complete, the excess amount of thionyl chloride and anhydrous ethanol are distilled off in vacuo,To give 1-chloroundecanoic acid;
	With thionyl chloride; In tetrachloromethane; for 2h;Reflux;	General procedure: For the preparation of chlorides higher than 10 Catoms the corresponding acid was refluxed for 2 h withthionyl chloride in CCl4.38 The solvent and the excess ofthionyl chloride were removed with the aid of the waterpump vacuum.
	With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere;	General procedure: A solution of oxalyl chloride in dry DCM (12 eq, 11.3 mL, 2M, 22.6 mmol) was added dropwise to a solution of the respective carboxylic acid (4 eq, 7.52 mmol) in dry DCM(20 mL) at 0C (ice bath) under nitrogen. The resulting mixture was stirred and allowed to reach room temperature over two hours. DCM was removed under vacuum and the acid chloride was dissolved in dry DMF (2mL) and cannulated into a solution of 3 (1.0eq, 0.5 g, 1.88 mmol) and dry pyridine (6.6 eq, 1 mL, 0.981 g, 12.40 mmol) in DMF(5 mL). The mixture was heated to 90C in an oil bath under a nitrogen atmosphere for two hours. After cooling the purple precipitate was filtered, washed with DMF(10 mL) and toluene (2 mL) and recrystallized from toluene.

Reference： [1]Canadian Journal of Chemistry,2008,vol. 86,p. 7 - 19
[2]Journal of Organic Chemistry,2010,vol. 75,p. 4769 - 4777
[3]Journal of the Chemical Society,1936,p. 284
[4]Bulletin de la Societe Chimique de France,1939,vol. <5>6,p. 507
[5]Annales Pharmaceutiques Francaises,1958,vol. 16,p. 757,760, 762
[6]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 751 - 754
Khimiya Geterotsiklicheskikh Soedinenii,1987,p. 915 - 918
[7]European Journal of Medicinal Chemistry,1991,vol. 26,p. 953 - 960
[8]Molecular Crystals and Liquid Crystals (1969-1991),1988,vol. 161,p. 1 - 24
[9]Journal of Organic Chemistry,1994,vol. 59,p. 2608 - 2612
[10]Helvetica Chimica Acta,1998,vol. 81,p. 902 - 915
[11]Synthesis,2001,p. 914 - 918
[12]Journal of Medicinal Chemistry,2005,vol. 48,p. 1849 - 1856
[13]Journal of Medicinal Chemistry,2006,vol. 49,p. 3872 - 3887
[14]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 9357 - 9365
[15]Chemical Communications,2005,p. 3198 - 3200
[16]Journal of Lipid Research,2010,vol. 51,p. 42 - 52
[17]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 3342 - 3349
[18]Chemistry and Physics of Lipids,2011,vol. 164,p. 118 - 124
[19]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2357 - 2361
[20]Crystal Growth and Design,2014,vol. 14,p. 4944 - 4954
[21]Journal of Lipid Research,2015,vol. 56,p. 2029 - 2039
[22]Journal of Chemical Sciences,2015,vol. 127,p. 1627 - 1635
[23]Chemistry and Physics of Lipids,2016,vol. 201,p. 1 - 10
[24]Patent: CN106167506,2016,A .Location in patent: Paragraph 0087
[25]Acta Chimica Slovenica,2017,vol. 64,p. 603 - 612
[26]Molecular Crystals and Liquid Crystals,2018,vol. 665,p. 82 - 90
[27]Organic Letters,2019,vol. 21,p. 7099 - 7103

2
[ 17746-05-3 ]
[ 71-43-2 ]
[ 4433-30-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	for 2h; Heating;
	With aluminium trichloride
	With aluminum (III) chloride

Reference： [1]Gray, George W.; Lacey, David; Scrowston, Richard M.; Shenouda, Ibrahim G.; Toyne, Kenneth J. [Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 164, p. 101 - 116]
[2]Breusch; Oguzer [Chemische Berichte, 1954, vol. 87, p. 1225,1227, 1228]
[3]Location in patent: scheme or table Zygadlo; Dardas; Nowicka; Hofmann; Galewski [Molecular Crystals and Liquid Crystals, 2009, vol. 509, # 1, p. 283 - 291]

3
[ 1653-30-1 ]
[ 17746-05-3 ]
[ 55194-01-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Schlenk,W. [Justus Liebigs Annalen der Chemie, 1973, p. 1179 - 1194]

4
[ 2807-30-9 ]
[ 17746-05-3 ]
[ 20207-42-5 ]

Reference： [1]Riemschneider,R. et al. [Monatshefte fur Chemie, 1968, vol. 99, p. 652 - 657]

5
[ 4062-60-6 ]
[ 17746-05-3 ]
[ 61797-56-6 ]

Reference： [1]Patent: DE2515146,1976,
Chem.Abstr.,1977,vol. 86
[2]Patent: DE2551483,1977,
Chem.Abstr.,1977,vol. 87

6
[ 17746-05-3 ]
[ 825-41-2 ]
[ 5540-94-3 ]

Reference： [1]Journal of Medicinal Chemistry,1966,vol. 9,p. 428 - 430

7
[ 17746-05-3 ]
[ 10212-25-6 ]
(3aS)-3c-undecanoyloxy-2t-undecanoyloxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1976,vol. 19,p. 663 - 667

8
[ 17746-05-3 ]
[ 3102-70-3 ]
[ 107976-27-2 ]

Reference： [1]Canadian Journal of Chemistry,1988,vol. 66,p. 1867 - 1871

9
[ 17746-05-3 ]
[ 4316-73-8 ]
[ 36461-64-0 ]

Reference： [1]Journal of the Indian Chemical Society,1982,vol. 59,p. 856 - 859

10
[ 17746-05-3 ]
[ 461-05-2 ]
[ 142759-00-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1991,vol. 26,p. 953 - 960

11
[ 17746-05-3 ]
[ 24155-42-8 ]
Undecanoic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 701 - 706

12
[ 17746-05-3 ]
[ 70-30-4 ]
[ 19809-92-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Quintana,R.P. et al. [Canadian Journal of Chemistry, 1968, vol. 46, p. 2835 - 2842]

13
[ 17746-05-3 ]
[ 26081-03-8 ]
(S)-3-undecanoylamino-caprolactam [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium carbonate; In dichloromethane; water; at 20℃; for 2.0h;	Example 2: (S)-3-undecanoylamino-caprolactam : ()-3-amino-caprolactam hydrochloride (2 mmol) and Na2CO3 (6 mmol) in water (25 ml) were added to a solution of undecanoyl chloride (2 mmol) in dichloromethane (25 ml) at ambient temperature and the reaction mixture was stirred for 2 hours. The organic layer was then separated and the aqueous phase was extracted with additional dichloromethane (2 x 25 ml). The combined organic layers were dried over Na2CO3 and reduced in vacuo. The residue was purified by recrystallisation from EtOAc to give the title compound (397 mg, 67%). Melting point: 91-92 C. [alpha]D25 (c = 1, CHCl3) = +30. 2. IR: vmax (crn~l) : 3342,3313 (NH), 1676,1638 (CO), 1519 (NH); 3342,3292 (NH), 1671,1639 (CO), 1513 (NH). 'H NMR (6H, 500 MHz, d6-DMSO) : 7.76 (1H, t, J6, CH2NH), 7.68 (1H, d, J7, CHNH), 4. 38 (1H, dd, J 10, 7, CHNH), 3.15 (1H, ddd, J 15. 5,11, 5, CHHNH), 3.04 (1H, dt, J 13,6, CHHNH), 2.19-2. 06 (2H, m, CH2CONH), 1.85 (1H, dt, J 10.5, 3, C-5 H), 1.77-1. 68 (2H, m, C-4 H, C-6 H), 1.60 (1H, qt, J 12,3. 5, C-5 H), 1.46 (2H, br qn J 6. 5, CH2CH2CONH), 1.35 (1H, qd, J 12. 5,3, C-4 H), 1.31-1. 13 (15H, m, (CH2)7 + C-6 H) and 0.85 (3H, t, J7. 0, CH3). 13C NMR (8c, 125 MHz, d6-DMSO) : 174.4 (CO-ring), 171.3 (CO-chain), 51.3 (NHCHCO), 40.7 (NCH2), 35.2, 31.4, 31.3, 29.1, 29.0 (x2), 28.9, 28. 8,28. 7, 27.8, 25.4, 22.2 (CH2) and 14.0 (CH3). m/z (Cl7H32N202Na) : 319.23540 (calculated: 319.2361).

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 867 - 874
[2]Patent: WO2005/53702,2005,A2 .Location in patent: Page/Page column 17

14
[ 17746-05-3 ]
[ 2244-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. NaN₃ / acetone / 0.33 h / 0 °C 2: 69 percent / Li; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Yus, Miguel; Radivoy, Gabriel; Alonso, Francisco [Synthesis, 2001, # 6, p. 914 - 918]

15
[ 17746-05-3 ]
[ 112-44-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / benzene / 0.5 h 2: 97 percent / 1,4-cyclohexadiene / benzene / 110 h / Irradiation
90%Chromat.	Stage #1: undecanoyl chloride With morpholine; diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With lithium diisobutylmethoxy aluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.166667h;	Partial reduction of acid chlorides to corresponding aldehydes General procedure: The following experimental procedure for the partial reduction of benzoyl chloride to benzaldehyde is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.11 mL, 1.25 mmol) and THF (10 mL). After cooling to 0 °C, DIBALH (1.2 mL, 1.0 M in hexane, 1.2 mmol) was added dropwise and the mixture was stirred for 3 h at the same temperature. Benzoyl chloride (0.116 mL, 1.0 mmol) was added slowly to the reaction mixture, which was stirred for 10 min. Then, LDBMA (3.3 mL, 0.46 M in hexane-THF, 1.5 mmol) was added and the mixture was stirred for 10 min again. The reaction was stopped by aqueous 1 N HCl (10 mL) and extracted with diethyl ether (2 × 10 mL). The combined organic layers were dried over MgSO4. GC analysis showed a 99% yield of benzaldehyde. All products in Table 2 were confirmed through comparison with GC data of authentic sample.

Reference： [1]Penn, John H.; Liu, Fang [Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2608 - 2612]
[2]Park, Jae Kyo; Shin, Won Kyu; An, Duk Keun [Tetrahedron Letters, 2013, vol. 54, # 24, p. 3199 - 3203]

16
[ 75-34-3 ]
[ 17746-05-3 ]
[ 103-45-7 ]
[ 162358-85-2 ]

Yield	Reaction Conditions	Operation in experiment
	In nitrogen	290.1 (1) (1) 2-(4-Dodecanoylphenyl)ethyl Acetate Aluminum chloride (48.2 g) was added to dichloroethane (400ml) in a stream of nitrogen and the mixture was stirred at room temperature. Then, phenethyl acetate (39.6 g) and undecanoyl chloride (52.7 g) were dropwise added thereto under ice-cooling and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20) to give the subject compound (34.5 g) as pale yellow crystals. melting point=32°-33° C. IR(neat)max: 2921, 2852, 1738, 1686, 1240 cm-1;

Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION; MITSUI DM SUGAR HOLDINGS CO LTD - US5604229, 1997, A

17
[ 2834-05-1 ]
10-bromo undecanyl ferrocenyl ketone [ No CAS ]
[ 17746-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In dichloromethane	P.1.1 Preparation Example 1 (1) 11-undecanic acid chloride prepared from 50.0 g of 11-bromoundecanic acid and 90.0 g of thionyl chloride, 37.6 g of anhydrous aluminum chloride, and 35.0 g of ferrocene were reacted at 5°C for 3 hours in a methylene chloride solvent. After the completion of the reaction, the reaction mixture was treated with diluted hydrochloric acid and then purified with a silica gel column to obtain 56.9 g of 10-bromo undecanyl ferrocenyl ketone represented by the following formula:

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP331745, 1989, A1

18
[ 17746-05-3 ]
[ 1134-47-0 ]
[ 1073838-92-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7983 - 7991

19
[ 17746-05-3 ]
[ 548-61-8 ]
[ 1174046-22-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In dichloromethane

Reference： [1]Location in patent: experimental part Houjou, Hirohiko; Koga, Tatsuya; Akiizumi, Midori; Yoshikawa, Isao; Araki, Koji [Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 6, p. 730 - 736]

20
[ 142340-15-6 ]
[ 17746-05-3 ]
[ 1240507-75-8 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2010,vol. 48,p. 3693 - 3701

21
[ 17746-05-3 ]
[ 392662-65-6 ]
[ 1313597-94-2 ]

Yield	Reaction Conditions	Operation in experiment
94%		According to Scheme 5, to a mixture of compound g (12.43 g, 0.0417 mol) and AlCl3 (12.78 g, 0.0959 mol) in CH2Cl2 (70 mL) at 0 C., n-Undecanoyl chloride (10.25 g, 0.0500 mol) was added dropwise under a nitrogen stream. This was stirred at 0 C. for about 12 hours until only small amount of starting materials could be detected by GC/MS. The mixture was then poured into HCl (200 mL, 6M) and the organic was extracted with hexanes/CH2Cl2 (1:1) (2×200 mL). The combined organic solution was washed with brine (2×100 mL) and water (100 mL). After drying over anhydrous MgSO4, the solvent was evaporated. A low melting point solid of compound 15 was collected and was recrystallized from EtOH to yield a purified product (18.32 g, 94%). GC-MS 465 [M+].

Reference： [1]Patent: US2012/22116,2012,A1 .Location in patent: Page/Page column 54

22
[ 17746-05-3 ]
[ 150-86-7 ]
phytyl dodecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With pyridine; dmap at 30 - 35℃; for 14h;

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]

23
[ 17746-05-3 ]
[ 6645-46-1 ]
undecanoyl carnitine [ No CAS ]

Reference： [1]Journal of Lipid Research,2015,vol. 56,p. 2029 - 2039

24
[ 17746-05-3 ]
[ 105047-45-8 ]
(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-undecanamidohexanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 20h;	Preparation of (S)-2- ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6- undecanamidohexanoic acid To a round-bottom flask charged with (S)-2-((((9H-fluoren-9- yl)methoxy)carbonyl)amino)-6-aminohexanoic acid (2.5 g, 6.79 mmol), undecanoyl chloride (1.647 ml, 7.46 mmol), and dichloromethane (27 ml) was added N-ethyl-Nisopropylpropan-2-amine (3.56 ml, 20.36 mmol). The initial suspensionimmediately turns yellow and then clear. After 10 minutes a solid begins to precipitate. The reaction was stirred for 20 hours at room temperature. The reaction mixture was diluted with 20 ml dichloromethane and poured into saturated ammonium chloride solution. The layers were separated and the aqueous was washed with a 20% methanol/chloroform solution. The combined organics werewashed with brine, dried over magnesium sulfate, filtered, and concentrated to give a sticky yellow solid. The resulting residue was subjected to silica gel chromatography (0-5% methanol/dichloromethane gradient) to afford (S)-2-((((9H- fluoren-9-yl)methoxy)carbonyl)amino)-6-undecanamidohexanoic acid (2.81 g, 5.24 mmol, 77 % yield) as a yellow foam. ‘H NMR (400MHz, CHLOROFORM-d) ö7.80 - 7.71 (m, 2H), 7.63 - 7.52 (m, 2H), 7.39 (t, J=7.0 Hz, 2H), 7.34 - 7.27 (m, 2H),4.49 - 4.29 (m, 2H), 4.27 - 4.14 (m, 1H), 3.24 (br. s., 1H), 2.35 (t, J=7.5 Hz, 1H),2.29-2.06 (m, 2H), 1.89 (br. s., 1H), 1.86 - 1.72 (m, 1H), 1.72- 1.63 (m, 1H), 1.62 -1.46 (m, 4H), 1.39 - 1.14 (m, 18H), 0.92 - 0.86 (m, 3H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2016/77518, 2016, A1 Location in patent: Page/Page column 143

25
[ 17746-05-3 ]
[ 58-22-0 ]
[ 5949-44-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere;	1 Example 1 First, under nitrogen, 5g of testosterone and 25ml of N,N-dimethylformamide (DMF, solvent), as well as 5ml pyridine (pyridine, base) are well-mixed, and then, at 0-10 deg.C was added 4.6ml undecanoyl chloride, and react at room temperature for 1 hour. After completion of the reaction, 5ml of water was added and stirred for 1 hour and the precipitated product was filtered, and then rinsed under aqueous acetone and the product dried in vacuo at room temperature after to obtain 7.6g of testosterone undecyl acid, yield 96%, HPLC: 98.26%. And then the, re-crystallization step is undecyl Testosterone 120g 480ml of acetone was added and stirred until the whole solution, followed by addition of 180ml of water and stirred for 0.5 hours, filtered and washed with an aqueous solution of acetone and run through again after crystallization resulting undecyl acid testosterone S crystalline (Form S),
13.5 g	With dmap; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 40℃;	3 Example 3 Preparation of Testosterone Undecanoate Under argon protection, put 10g of 17β-hydroxyandrost-4-en-3-one intoTo 200ml of dichloroethane, add 120ml of diisopropylethylamine, 10g of 4-dimethylaminopyridine, blow nitrogen to replace the air in the reaction flask, turn on the stirring,152.6ml of undecanoyl chloride was added, and the reaction was completed at 40°C. Add 1ml water to quench,Layered, washed with water, concentrated, filtered, and dried to obtain 13.5 g of testosterone undecanoate with a yield of 135%, The purity is 99.2%.

Reference： [1]Current Patent Assignee: EVERLIGHT CHEMICAL INDUSTRIAL CORPORATION - CN105732754, 2016, A Location in patent: Paragraph 0024; 0025; 0026; 0027; 0028
[2]Current Patent Assignee: ZHEJIANG SHENZHOU PHARMACEUTICAL - CN111848713, 2020, A Location in patent: Paragraph 0024-0025

26
[ 17746-05-3 ]
[ 5981-09-9 ]
C₅₁H₇₈N₄O₃ [ No CAS ]

Reference： [1]Crystal Growth and Design,2018,vol. 18,p. 6284 - 6292

27
[ 65079-19-8 ]
[ 17746-05-3 ]
C₂₁H₃₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
154 mg	With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;	7 Example 7. Preparation of Compound D7 Weigh 6-amino-2-methylquinoline (158 mg, 1 mmol),Dissolved in 15 ml of acetonitrile, followed by N,N-diisopropylethylamine DIPEA (157 mg, 1.2 mmol) and undecyl chloride (246 mg, 1.2 mmol).After mixing, stir at room temperature overnight.After the reaction was completed, the solvent acetonitrile was removed under reduced pressure, and an appropriate amount of water (10 ml) was added.The aqueous layer was extracted with ethyl acetate (20 ml*3).The ethyl acetate layer was washed twice with brine; after the ethyl acetate layer was concentrated,Column chromatography was carried out using a mixed solvent of petroleum ether: ethyl acetate = 10:1 to afford product 154 mg.

Reference： [1]Current Patent Assignee: CHENGDU MILITARY GENERAL HOSPITAL PLA - CN109020886, 2018, A Location in patent: Paragraph 0061; 0062; 0063

28
[ 17746-05-3 ]
[ 1404-90-6 ]
N₃-undecanoylvancomycin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40 mg	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 2h;Cooling with ice; Inert atmosphere;	Step 1: commercially available <strong>[1404-90-6]vancomycin</strong> (100 mg) and DIPEA (30 muL) were dissolved in 3 mL of DMF. After the solution became clear, 15 muL of undecanoyl chloride was added in three portions under ice-water bath, and the reaction was stirred for 2h under argon. The reaction mixture was added with diethyl ether (50 mL) to generate precipitates, which was filtered to give a crude. The crude was purified by reverse-phase C18 HPLC and lyophilized to give Van-h (40 mg) as a white solid. HPLC: C18 column (5 mum, 4.6 x 250 mm), UV detection at 214 nm, elution conditions: a gradient of 2-90% acetonitrile containing 0.1% v/v TFA over 30 min. HRMS (ESI+) calculated for C77H95Cl2N9O25 [M+2H]2+ 1615.5816, found 808.7978. 1H NMR (600 MHz, DMSO-d6) delta 8.63 (s, 1H), 8.46 (d, J = 5.7 Hz, 1H), 7.80 (d, J = 2.0 Hz, 1H), 7.46 (dd, J = 8.4, 1.8 Hz, 1H), 7.43 (dd, J = 8.1, 1.9 Hz, 1H), 7.34 (d, J = 8.3 Hz, 1H), 7.22 (s, 1H), 7.17 - 7.15 (m, 1H), 7.00 (d, J = 8.3 Hz, 1H), 6.76 (dd, J = 8.5, 2.1 Hz, 1H), 6.70 (dd, J = 8.5, 3.2 Hz, 2H), 6.39 (d, J = 2.3 Hz, 1H), 6.22 (d, J = 2.3 Hz, 1H), 5.69 (d, J = 8.3 Hz, 1H), 5.48 (d, J = 2.1 Hz, 1H), 5.26 - 5.17 (m, 4H), 5.13 (d, J = 4.7 Hz, 1H), 5.08 (s, 1H), 4.77 (dd, J = 9.8, 4.5 Hz, 1H), 4.66 (d, J = 6.7 Hz, 1H), 4.45 (d, J = 5.7 Hz, 2H), 4.41 (d, J = 5.7 Hz, 1H), 4.18 (s, 1H), 3.64 (d, J = 10.8 Hz, 1H), 3.56 - 3.48 (m, 3H), 3.25 (d, J = 5.5 Hz, 2H), 3.13 (s, 1H), 2.82 (s, 3H), 2.41 - 2.30 (m, 3H), 2.10 (d, J = 12.7 Hz, 2H), 1.88 (d, J = 11.0 Hz, 1H), 1.71 (d, J = 13.1 Hz, 1H), 1.57 (d, J = 7.7 Hz, 3H), 1.50 - 1.42 (m, 2H), 1.36 (d, J = 7.3 Hz, 2H), 1.34 - 1.13 (m, 17H), 1.05 (d, J = 6.4 Hz, 3H), 0.85 (dd, J = 6.7, 2.4 Hz, 3H), 0.81 (t, J = 7.1 Hz, 3H), 0.77 (d, J = 6.6 Hz, 3H).

Reference： [1]Patent: EP3450450,2019,A1 .Location in patent: Paragraph 0135; 0136

29
[ 17746-05-3 ]
[ 226410-00-0 ]
methyl 3-chloro-5-undecanoyl-1H-pyrrole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With zinc(II) chloride; In 1,2-dichloro-ethane; at 0 - 20℃; for 18h;	To a solution of undecanoyl chloride (Intermediate 4a, 512 mg, 2.5 mmol) in DCE (4 mL) was added zinc(ll) chloride (342 mg, 2.5 mmol) and the mixture was cooled to 0 C. Then a solution of methyl 3-chloro-1 H-pyrrole-2-carboxylate (200 mg, 1.25 mmol) in DCE (4 mL) was added and the mixture was stirred at room temperature for 18 h. Ice and DCM were added to the reaction mixture and phases were separated. The organic phase was washed with aqueous saturated sodium hydrogen carbonate solution and brine, dried over magnesium sulfate, filtered and solvent evaporated. Purification of the residue by flash chromatography (hexanes/EtOAc) gave the title compound (100 mg, 24%) as a yellow solid. MS (m/z): 328/330 [M+1]+. 1 H-NMR 5 (400 MHz, CDCb): 0.88 (t, J=7 Hz, 3H), 1.18-1.38 (14H), 1.70 (p, J=7 Hz, 2H), 2.75 (t, J=7 Hz, 2H), 3.93 (s, 3H), 6.80 (d, J=3 Hz, 1 H), 9.80 (br s, 1 H).

Reference： [1]Patent: WO2019/115405,2019,A1 .Location in patent: Page/Page column 61; 62

30
[ 104-67-6 ]
[ 17746-05-3 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 7099 - 7103

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[ CAS No. 17746-05-3 ] {[proInfo.proName]}

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[ 17746-05-3 ] Synthesis Path-Upstream 1~4

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