[ CAS No. 67342-99-8 ] {[proInfo.proName]}

Name: 67342-99-8|Ethyl 3-oxododecanoate|95%
Brand: Ambeed
SKU: A155599
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Quality Control of [ 67342-99-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 67342-99-8 ]

CAS No. :	67342-99-8	MDL No. :	MFCD20127688
Formula :	C₁₄H₂₆O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GUIDAPPCHUNALD-UHFFFAOYSA-N
M.W :	242.35	Pubchem ID :	3017756
Synonyms :

Calculated chemistry of [ 67342-99-8 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	12
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	70.9
TPSA :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.66
Log Po/w (XLOGP3) :	4.41
Log Po/w (WLOGP) :	3.65
Log Po/w (MLOGP) :	2.7
Log Po/w (SILICOS-IT) :	4.12
Consensus Log Po/w :	3.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.33
Solubility :	0.114 mg/ml ; 0.000469 mol/l
Class :	Soluble
Log S (Ali) :	-5.04
Solubility :	0.00222 mg/ml ; 0.00000916 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.35
Solubility :	0.0109 mg/ml ; 0.000045 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	2.48

Safety of [ 67342-99-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 67342-99-8 ]

* 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.

Downstream synthetic route of [ 67342-99-8 ]

[ 67342-99-8 ] Synthesis Path-Downstream 1~88

1
[ 463-51-4 ]
[ 67342-99-8 ]
[ 13195-93-2 ]

Reference： [1]Chemical Abstracts,1947,p. 4169
[2]Patent: US2417381,1945,

2
[ 64-17-5 ]
[ 61058-75-1 ]
[ 67342-99-8 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1903,vol. 136,p. 753
Bulletin de la Societe Chimique de France,1903,vol. <3> 29,p. 668

3
[ 67342-99-8 ]
5-nonyl-1,2-dihydro-pyrazol-3-one [ No CAS ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1954,vol. 74,p. 1086,1088
Chem.Abstr.,1955,p. 11628

4
[ 67342-99-8 ]
[ 61058-75-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With water; sodium hydroxide; In ethanol; at 20℃; for 12h;	Compound 12-1 (647 mg, 2.67 mmol, 1 eq.) was dissolved in EtOH/H20 (10/10 mE), then added NaOH (139 mg, 3.47 mmol, 1.3 eq.). The reaction was stirred at 20 C. for 12 h. The reaction mixture was washed twice with ethyl acetate (10 mE). The aqueous layer was adjusted to acidic (pH 3-5) with iN HC1. A white solid was precipitated, filtered and dried in vacuo to obtain compound 13-1 (white solid, 410 mg, 72%). ?H NMR (300 MHz, DMSO) oe 12.53 (s, 1H), 3.43 (s, 2H), 2.39 (t, J=7.2 Hz, 2H), 1.23 (m, 14H), 0.85 (t, J=6.3 Hz, 3H).

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 1021 - 1031
[2]Patent: US2018/237399,2018,A1 .Location in patent: Paragraph 0130; 0132
[3]Journal of Medicinal Chemistry,1987,vol. 30,p. 1017 - 1023
[4]Istanbul Universitesi Fen Fakultesi Mecmuasi, Seri A: Matematik-Fizik-Kimya,1946,vol. 11,p. 26
Chem.Abstr.,1946,p. 5400
[5]Tetrahedron Letters,1996,vol. 37,p. 1883 - 1884
[6]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 579 - 583
[7]RSC Advances,2016,vol. 6,p. 73717 - 73730

5
[ 67342-99-8 ]
[ 100-63-0 ]
5-nonyl-2-phenyl-1,2-dihydro-pyrazol-3-one [ No CAS ]

Reference： [1]Istanbul Universitesi Fen Fakultesi Mecmuasi,1946,vol. <A> 11,p. 24,26

6
[ 67342-99-8 ]
[ 546-67-8 ]
[ 37409-57-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1972,vol. 8,p. 902 - 903
Khimiya Geterotsiklicheskikh Soedinenii,1972,vol. 8,p. 991 - 993

7
[ 15776-03-1 ]
[ 67342-99-8 ]

Reference： [1]Journal of the Chemical Society C: Organic,1966,p. 1743 - 1753

8
[ 290-87-9 ]
[ 67342-99-8 ]
[ 74631-99-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 359 - 368

9
[ 13200-60-7 ]
[ 67342-99-8 ]
[Methyl-(3-oxo-dodecanoyl)-amino]-acetic acid ethyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4197 - 4204

10
[ 56428-90-1 ]
[ 67342-99-8 ]
2-[Methyl-(3-oxo-dodecanoyl)-amino]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4197 - 4204

11
[ 334-48-5 ]
[ 37517-78-5 ]
[ 67342-99-8 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1017 - 1023
[2]Journal of Medicinal Chemistry,1993,vol. 36,p. 2943 - 2949

12
[ 67342-99-8 ]
[ 6436-90-4 ]
[Benzyl-(3-oxo-dodecanoyl)-amino]-acetic acid ethyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4197 - 4204

13
[ 67342-99-8 ]
[ 64892-53-1 ]
2-[Benzyl-(3-oxo-dodecanoyl)-amino]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4197 - 4204

14
[ 67342-99-8 ]
[ 112-12-9 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2943 - 2949

15
[ 67342-99-8 ]
[ 13283-92-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 2494 - 2502

16
[ 13195-93-2 ]
[ 67342-99-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1077 - 1079

17
2-Methyl-3-nonyl-5-oxo-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester [ No CAS ]
[ 67342-99-8 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 6339 - 6340
[2]Journal of Chemical Research, Miniprint,1991,p. 324 - 346

18
(Z)-3-Methylamino-dodec-2-enoic acid ethyl ester [ No CAS ]
[ 67342-99-8 ]

Reference： [1]Journal of Chemical Research, Miniprint,1991,p. 324 - 346

19
[ 67342-99-8 ]
[ 105-36-2 ]
[ 73642-74-7 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 3061 - 3064

20
[ 1071-46-1 ]
[ 112-13-0 ]
[ 67342-99-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 2494 - 2502
[2]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4197 - 4204

21
[ 112-13-0 ]
[ 67342-99-8 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 3061 - 3064
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 3543 - 3548
[3]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1077 - 1079
[4]Journal of the Chemical Society C: Organic,1966,p. 1743 - 1753
[5]Patent: EP2077109,2009,A1

22
[ 67342-99-8 ]
[ 62-53-3 ]
[ 55396-45-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1077 - 1079
[2]Chemistry and Biology,2012,vol. 19,p. 381 - 390

23
[ 50-00-0 ]
[ 67342-99-8 ]
[ 53676-48-5 ]
[ 41387-26-2 ]

Reference： [1]European Journal of Medicinal Chemistry,1977,vol. 12,p. 161 - 171

24
[ 112-12-9 ]
[ 541-41-3 ]
[ 67342-99-8 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 1883 - 1884

25
[ 24715-24-0 ]
[ 67342-99-8 ]
[ 201804-93-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 3543 - 3548

26
[ 24715-24-0 ]
[ 67342-99-8 ]
2-[2-Acetylamino-1-hydroxy-eth-(E)-ylidene]-3-oxo-dodecanoic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 3543 - 3548

27
[ 64-17-5 ]
[ 429675-23-0 ]
[ 67342-99-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 3543 - 3548

28
[ 37595-74-7 ]
[ 67342-99-8 ]
(Z)-3-Trifluoromethanesulfonyloxy-dodec-2-enoic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 8613 - 8616

30
2-caprinoyl-acetoacetic acid ethyl ester [ No CAS ]
[ 67342-99-8 ]

Reference： [1]Istanbul Universitesi Fen Fakultesi Mecmuasi, Seri A: Matematik-Fizik-Kimya,1946,vol. 11,p. 26
Chem.Abstr.,1946,p. 5400

31
[ 67342-99-8 ]
[ 112-76-5 ]
2-decanoyl-3-oxo-eicosanoic acid ethyl ester [ No CAS ]

Reference： [1]Phytochemistry,2000,vol. 54,p. 325 - 336

32
[ 67342-99-8 ]
[ 113738-28-6 ]
(Z)-3-(2,2-Diethoxy-ethylamino)-dodec-2-enoic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 2151 - 2154

33
[ 67342-99-8 ]
(S)-(1,1'-binaphthyl-2,2'-dioxy)chlorophosphine [ No CAS ]
C₃₄H₃₉O₅P [ No CAS ]
C₃₄H₃₉O₅P [ No CAS ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 1067 - 1076

34
[ 67342-99-8 ]
[ 893842-45-0 ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 1067 - 1076
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 5285 - 5296

35
[ 67342-99-8 ]
[ 893842-45-0 ]
(S)-ethyl 3-hydroxydodecanoate [ No CAS ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 1067 - 1076

36
[ 141-97-9 ]
1H-1,2,3-benzotriazol-1-yl(n-nonyl)methanone [ No CAS ]
[ 67342-99-8 ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 1617 - 1625

37
[ 75-77-4 ]
[ 67342-99-8 ]
[ 856704-67-1 ]

Reference： [1]Synthesis,2006,p. 2865 - 2872

38
[ 629-27-6 ]
[ 141-97-9 ]
[ 67342-99-8 ]

Reference： [1]Synthesis,2006,p. 2865 - 2872

39
[ 67342-99-8 ]
(2Z)-ethyl 2-[4-hydroxy-3-octyl-5-oxofuran-2(5H)-ylidene]acetate [ No CAS ]

Reference： [1]Synthesis,2006,p. 2865 - 2872

40
[ 67342-99-8 ]
[ 628315-88-8 ]

Reference： [1]Synthesis,2006,p. 2865 - 2872

41
[ 67342-99-8 ]
C₃₄H₃₉O₅P [ No CAS ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 1067 - 1076
[2]Synthetic Communications,2007,vol. 37,p. 1067 - 1076

42
[ 67342-99-8 ]
10,12-nonacosanedione [ No CAS ]

Reference： [1]Phytochemistry,2000,vol. 54,p. 325 - 336

43
[ 67342-99-8 ]
[ 217963-31-0 ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 8613 - 8616

44
[ 67342-99-8 ]
[ 76562-72-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 3543 - 3548
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 3543 - 3548

45
[ 67342-99-8 ]
[ 168982-69-2 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 1883 - 1884

46
[ 67342-99-8 ]
N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-dodecanamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2943 - 2949

47
[ 67342-99-8 ]
[ 107617-17-4 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1017 - 1023
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 579 - 583

48
[ 67342-99-8 ]
3-Decanoyl-4-hydroxy-1-methyl-1,5-dihydro-pyrrol-2-one [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4197 - 4204

49
[ 67342-99-8 ]
3-Decanoyl-4-hydroxy-1,5-dimethyl-1,5-dihydro-pyrrol-2-one [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4197 - 4204

50
[ 67342-99-8 ]
1-Benzyl-3-decanoyl-4-hydroxy-1,5-dihydro-pyrrol-2-one [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4197 - 4204

51
[ 67342-99-8 ]
1-Benzyl-3-decanoyl-4-hydroxy-5-methyl-1,5-dihydro-pyrrol-2-one [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 4197 - 4204

52
[ 570-08-1 ]
[ 67342-99-8 ]

Reference： [1]Journal of Chemical Research, Miniprint,1991,p. 324 - 346

53
[ 133827-52-8 ]
[ 67342-99-8 ]

Reference： [1]Journal of Chemical Research, Miniprint,1991,p. 324 - 346

54
[ 61975-86-8 ]
[ 67342-99-8 ]

Reference： [1]Journal of Chemical Research, Miniprint,1991,p. 324 - 346
[2]Tetrahedron Letters,1988,vol. 29,p. 6339 - 6340

55
[ 67342-99-8 ]
[ 68353-24-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1077 - 1079

56
[ 67342-99-8 ]
[ 80554-63-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1077 - 1079

57
[ 111-83-1 ]
[ 67342-99-8 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 6339 - 6340

58
potassium salt of ethyl 2,5-dihydro-2,3-dimethyl-5-oxoisoxazole-4-carboxylate [ No CAS ]
[ 67342-99-8 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 6339 - 6340

59
[ 67587-18-2 ]
[ 67342-99-8 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1903,vol. 136,p. 753
Bulletin de la Societe Chimique de France,1903,vol. <3> 29,p. 668

60
[ 955404-46-3 ]
[ 64-17-5 ]
[ 67342-99-8 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6537 - 6541

61
[ 67342-99-8 ]
[ 113738-28-6 ]
[ 1135793-34-8 ]

Reference： [1]Synthesis,2009,p. 227 - 242

62
[ 64-17-5 ]
[ 182359-65-5 ]
[ 67342-99-8 ]

Yield	Reaction Conditions	Operation in experiment
	for 2h;Reflux;	Reference Example 4: Production of 3,3-ethylene glycosyl dodecanoyl acid; (1) Production of ethyl 3-oxododecanoate; Meldrum's acid (7.20 g, 50 mmol) and triethyl amine (5.56 g, 55 mmol) were dissolved in dichloromethane (50 mL), and decanoic acid chloride (10.48 g, 55 mmol) was added to the resulting mixture dropwise while cooling with ice. The reaction mixture was stirred at room temperature for about 12 hours, and then concentrated under reduced pressure. The ethyl acetate layer thus obtained was washed with diluted hydrochloric acid and an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified using silica gel chromatography (developing solvent: n-hexane/ethyl acetate = 3/7) to obtain 5-decanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione. The resulting 5-decanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione was allowed to reflux in ethanol for 2 hours, and then concentrated under reduced pressure. The resulting residue was purified using silica gel chromatography (developing solvent: n-hexane/ethyl acetate = 3/7) to obtain the ethyl 3-oxododecanoate shown by the formula below. [Show Image] Quantity Yield: 11.85 g (48.9 mmol) Percent Yield: 98% 1H-NMR (CDCl3, 500 MHz) : 0.91 ppm (t, 3H), 1.30 ppm (m, 15H), 1.62 ppm (m, 2H), 2.55 ppm (m, 2H), 3.45 ppm (s, 2H), 4.20 ppm (q, 2H).
	for 2h;Heating / reflux;	7.20g (50mmol) of Meldrum's acid and 5.56g (55mmol) of triethylamine were dissolved in 50mL of dichloromethane. 10.48g (55mmol) of decanoyl chloride was dropped in this solution while cooling the solution with ice. The reaction liquid was stirred for 12 hours at room temperature, and was concentrated under reduced pressure. The resulting residue was subjected to extraction with ethyl acetate. The obtained ethyl acetate layer was washed with diluted hydrochloric acid and saturated saline, dried with magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=3/7) to obtain a Meldrum's acid derivative. The obtained Meldrum's acid derivative was circulated in ethanol for two hours, and was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=3/7). As a result, 3-oxododecanoyl acid ethyl ester denoted by the following formula was obtained. [Show Image] Quantity Yield: 11.85g (0.69mmol) Percent Yield: 99% 1H-NMR (CDCl3, 500MHz); 0.91ppm (t, 3H), 1.30ppm (m, 15H), 1.62ppm (m, 2H), 2.55ppm(m, 2H), 3.45ppm (s, 2H), 4.20ppm (q, 2H).

Reference： [1]Patent: EP2221293,2010,A1 .Location in patent: Page/Page column 11-12
[2]Patent: EP2077109,2009,A1 .Location in patent: Page/Page column 12

63
[ 67342-99-8 ]
[ 107-21-1 ]
[ 663883-62-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With toluene-4-sulfonic acid; In benzene; for 6h;Dean-Stark conditions; Reflux;	(2) Production of 3,3-ethylene glycosyl dodecanoyl acid Ethyl 3-oxododecanoate (6.05 g, 25 mmol) obtained in (1) above, ethylene glycol (7.75 g, 125 mmol), and p-toluenesulfonic acid monohydrate (0.48 g, 2.5 mmol) were dissolved in benzene (50 mL), and allowed to reflux using a reflux apparatus equipped with a Dean Stark device for 6 hours. After cooling, the thus-obtained organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified using silica gel chromatography (developing solvent: n-hexane/ethyl acetate = 5/5) to obtain the ethyl 3,3-ethylene glycosyl dodecanoate shown by the formula below. Quantity Yield: 6.99 g (24.5 mmol) Percent Yield: 98% 1H-NMR (CDCl3, 500 MHz): 0.91 ppm (t, 3H), 1.29 ppm (m, 15H), 1.33 ppm (m, 2H), 1.81 ppm (m, 2H), 2.67 ppm (s, 2H), 4.01 ppm (m, 4H), 4.19 ppm (q, 2H).
98%	toluene-4-sulfonic acid; In benzene; for 6h;Heating / reflux;	6.05g (25mmol) of the 3-oxododecanoyl acid ethyl ester obtained in the process (1), 7.75g (125mmol) of ethylene glycol, and 0.48g (2.5mmol) of p-toluene sulfonic acid monohydrate were dissolved in 50mL of benzene, and the solution was circulated for six hours by a circulation device incorporating the Dean and Stark device. After cooling, the reaction liquid was washed with saturated sodium bicarbonate water, dried with magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=5/5). As a result, 3,3-ethylene glycosyl dodecanoyl acid ethyl ester denoted by the following formula was obtained. [Show Image] Quantity Yield: 6.99g(24.5mmol) Percent Yield: 98% 1H-NMR (CDCl3, 500MHz); 0.91ppm (t, 3H), 1.29ppm (m, 15H), 1.33ppm (m, 2H), 1.81ppm (m, 2H), 2.67ppm (s, 2H), 4.01ppm (m, 4H), 4.19ppm (q, 2H).

Reference： [1]Patent: EP2221293,2010,A1 .Location in patent: Page/Page column 12
[2]Patent: EP2077109,2009,A1 .Location in patent: Page/Page column 12-13

64
[ 111-83-1 ]
[ 141-97-9 ]
[ 67342-99-8 ]

Yield	Reaction Conditions	Operation in experiment
34%		Compound 11(1 mE, 7.7 mmol, 1 eq.) was added in dry THF (20 mE), cooled to 00 C., then added NaH (203 mg, 8.5 mmol, 1.1 eq.), stirred for 5 minutes, added n-butyllithium (5.3 mE, 8.5 mmol, 1.6M, 1.1 eq.). Stirred for another 5 minutes, bromide (1.3 mE, 7.7 mmol, 1 eq.) was added and stirred at 00 C. for 12 h monitored by TEC. The reaction mixture turned into a yellow milky liquid. Afier full completion, the reaction was quenched with water (10 mE) and extracted three times with ethyl acetate (10 mE). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and purified by a flash chromatography on silica gel to give compound 12-1 (yellow oil, 647 mg, 34%). ?H NMR (300 MHz, CDC13) oe 4.19 (q, J=15 Hz, 2H), 3.42 (s, 2H), 2.53 (t, J=7.2 Hz, 2H), 1.28 (m, 14H), 0.87 (t, J=6.3 Hz, 3H). ?H NMR (300 MHz, DMSO) oe 12.53 (s, 1H), 3.43 (s, 2H), 2.39 (t, J=7.2 Hz, 2H), 1.23 (m, 14H), 0.85 (t, J=6.3 Hz, 3H).

Reference： [1]MedChemComm,2017,vol. 8,p. 1360 - 1365
[2]Patent: US2018/237399,2018,A1 .Location in patent: Paragraph 0130; 0131
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 5285 - 5296

65
[ 67342-99-8 ]
[ 62-53-3 ]
C₂₀H₃₁NO₂ [ No CAS ]

Reference： [1]Chemistry and Biology,2012,vol. 19,p. 381 - 390

66
[ 623-73-4 ]
[ 112-31-2 ]
[ 67342-99-8 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 960 - 964
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 1021 - 1031
[3]Green Chemistry,2014,vol. 16,p. 116 - 120

67
[ 67342-99-8 ]
Ac-Glu(tBu)-Thr(tBu)-Asp(tBu)-Lys-AMC [ No CAS ]
Ac-Glu-Thr-Asp-Lys(3-oxododecanoyl)-AMC [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 1021 - 1031

68
[ 67342-99-8 ]
[ 183613-15-2 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 960 - 964
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 1021 - 1031
[3]MedChemComm,2017,vol. 8,p. 1360 - 1365

69
[ 67342-99-8 ]
[ 1883-13-2 ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 1021 - 1031
[2]MedChemComm,2017,vol. 8,p. 1360 - 1365

70
[ 67342-99-8 ]
Ac-Glu-Thr-Asp-Lys((R/S)-3-hydroxydodecanoyl)-AMC [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 1021 - 1031

71
[ 112-29-8 ]
[ 141-97-9 ]
[ 67342-99-8 ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 579 - 583

72
[ 67342-99-8 ]
[ 75858-40-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 579 - 583

73
[ 67342-99-8 ]
6-nonylpyridine-2,4-diol [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 579 - 583

74
[ 112-12-9 ]
[ 105-58-8 ]
[ 67342-99-8 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 73717 - 73730

75
[ 67342-99-8 ]
D-3-Hydroxydodecansaeure [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 73717 - 73730

76
[ 67342-99-8 ]
N-(3-hydroxydodecanoyl-[3-²H])-L-homoserine lactone [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 73717 - 73730

77
[ 67342-99-8 ]
[ 596104-60-8 ]

Reference： [1]Patent: EP2077109,2009,A1

78
[ 67342-99-8 ]
C₃₇H₆₄N₆O₈ [ No CAS ]