[ CAS No. 112-37-8 ] {[proInfo.proName]}

Name: 112-37-8|Undecanoic acid|98%
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Quality Control of [ 112-37-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 112-37-8 ]

Product Details of [ 112-37-8 ]

CAS No. :	112-37-8	MDL No. :	MFCD00002730
Formula :	C₁₁H₂₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZDPHROOEEOARMN-UHFFFAOYSA-N
M.W :	186.29	Pubchem ID :	8180
Synonyms :	Undecanoate;Hendecanoic acid;NSC 7885;C11:0 Fatty acid;Undecylic acid	Chemical Name :	Undecanoic acid

Calculated chemistry of [ 112-37-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.91
Num. rotatable bonds :	9
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.76
TPSA :	37.3 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) :	-4.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.74
Log Po/w (XLOGP3) :	4.42
Log Po/w (WLOGP) :	3.6
Log Po/w (MLOGP) :	2.87
Log Po/w (SILICOS-IT) :	3.06
Consensus Log Po/w :	3.34

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.19
Solubility :	0.122 mg/ml ; 0.000652 mol/l
Class :	Soluble
Log S (Ali) :	-4.92
Solubility :	0.00223 mg/ml ; 0.000012 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.29
Solubility :	0.0966 mg/ml ; 0.000519 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	1.77

Safety of [ 112-37-8 ]

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 [ 112-37-8 ]

* 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 [ 112-37-8 ]
Downstream synthetic route of [ 112-37-8 ]

[ 112-37-8 ] Synthesis Path-Upstream 1~2

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

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

[ 112-37-8 ] Synthesis Path-Downstream 1~88

1
[ 64-17-5 ]
[ 112-37-8 ]
[ 627-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 20℃; for 12h;	General procedure: Prior to Gas Chromatography-Mass Spectrometry (GC-MS) analysis, active fractions andcommercial decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, and tetradecanoic acid(purity > 98%; Sigma-Aldrich, St. Louis, MI, USA) were methylated and ethylated. Samples (30 mg)were diluted with 10 mL acidified methanol or ethanol (1% sulfuric acid) and stirred for 12 h at roomtemperature. The product of the reaction was suspended in an aqueous solution of 20% Na2CO3(20 mL) and extracted with CHCl3 (3, 20 mL, each one) and the solvent was eliminated under vacuumuntil dry. These derivatives were stored at 4 C until use in assays [60].

Reference： [1]Arkiv foer Kemi,1945,vol. 20 A,p. 11
[2]Annales de Chimie (Cachan, France),1944,vol. <11> 19,p. 487,502
[3]Molecules,2019,vol. 24

2
[ 1002-69-3 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; Petroleum ether at -10℃; und anschliessenden Einleiten von CO₂;

Reference： [1]Morton; Davidson; Best [Journal of the American Chemical Society, 1942, vol. 64, p. 2239]

3
[ 593-08-8 ]
[ 112-37-8 ]

Reference： [1]Chemische Berichte,1879,vol. 12,p. 1669

4
[ 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

5
[ 112-37-8 ]
[ 780722-26-1 ]
[ 2244-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 210 - 215℃;

Reference： [1]Dangjan; Oganisjan [Chemical Abstracts, 1946, p. 3399]

6
[ 112-37-8 ]
[ 1562-00-1 ]
Undecanoic acid 2-sulfo-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene

Reference： [1]Hikota,T. et al. [Bulletin of the Chemical Society of Japan, 1970, vol. 43, p. 3913 - 3916]

7
[ 112-37-8 ]
[ 505-56-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1979,vol. 17B,p. 396

8
[ 186581-53-3 ]
[ 112-37-8 ]
[ 1731-86-8 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; at 0 - 20℃;	General procedure: Compound 1b (0.8 mg) was dissolved in 10% H2SO4 and acetone (2.0 mL each). KMnO4 (50 mg) was then added to the solution and stirred overnight at room temperature [16,20]. The reaction was then quenched with aqueous Na2S2O3 (5%). After removal of acetone, the reaction mixture was extracted with Et2O. The Et2O layer was dried over Na2SO4 and concentrated to yield the residue, which was methylated using CH2N2 in Et2O at 0 C [20]. The reaction mixture was kept in ice for 30 min before being allowed to stand at room temperature overnight. This procedure resulted in compound 1c (0.4 mg), which was identified as methyl nonanoate by GC-MS.

Reference： [1]Phytochemistry,1980,vol. 19,p. 75 - 78
[2]Molecules,2013,vol. 18,p. 11241 - 11249

9
[ 67-56-1 ]
[ 112-37-8 ]
[ 1731-86-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 20℃; for 12h;	General procedure: Prior to Gas Chromatography-Mass Spectrometry (GC-MS) analysis, active fractions andcommercial decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, and tetradecanoic acid(purity > 98%; Sigma-Aldrich, St. Louis, MI, USA) were methylated and ethylated. Samples (30 mg)were diluted with 10 mL acidified methanol or ethanol (1% sulfuric acid) and stirred for 12 h at roomtemperature. The product of the reaction was suspended in an aqueous solution of 20% Na2CO3(20 mL) and extracted with CHCl3 (3, 20 mL, each one) and the solvent was eliminated under vacuumuntil dry. These derivatives were stored at 4 C until use in assays [60].

Reference： [1]Synthetic Communications,1986,vol. 16,p. 1423 - 1430
[2]Synthetic Communications,2010,vol. 40,p. 1670 - 1676
[3]Chemistry and biodiversity,2016,vol. 13,p. 1202 - 1220
[4]Journal of Molecular Structure,2013,vol. 1040,p. 19 - 24
[5]CrystEngComm,2019,vol. 21,p. 41 - 52
[6]Molecules,2019,vol. 24

10
[ 6066-82-6 ]
[ 112-37-8 ]
[ 104943-24-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 5381 - 5390
[2]Journal of the American Chemical Society,1990,vol. 112,p. 2498 - 2506
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 3117 - 3121
[4]Journal of the American Chemical Society,2009,vol. 131,p. 44 - 45

11
[ 112-42-5 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
22%	With oxygen; acetic acid;N-hydroxyphthalimide; at 100℃; under 760.051 Torr; for 4h;	EXAMPLE 23 In 3 mL of acetic acid was dissolved 375 mg of 1-undecanol to give a solution, and the solution was combined with 150 mg of the catalyst B10 obtained from Example 22 and 32 mg of N-hydroxyphthalimide, followed by stirring at 100C in an oxygen atmosphere at normal atmospheric pressure for 4 hours. The reaction mixture was analyzed through gas chromatography to find that undecanoic acid was produced in a yield of 22% with a conversion from 1-undecanol of 44%.

Reference： [1]Organic Letters,2005,vol. 7,p. 2933 - 2936
[2]Journal of Organic Chemistry,1990,vol. 55,p. 462 - 466
[3]Russian Journal of Organic Chemistry,2007,vol. 43,p. 773 - 774
[4]Bulletin of the Chemical Society of Japan,2009,vol. 82,p. 1000 - 1002
[5]Patent: EP2248792,2010,A1 .Location in patent: Page/Page column 19
[6]Catalysis science and technology,2014,vol. 4,p. 2564 - 2573
[7]ChemPlusChem,2016,vol. 81,p. 1160 - 1165

12
[ 112-41-4 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With [Me(n-Oct)3N]3{PO4[WO(O2)2]4}; dihydrogen peroxide; In water; 1,2-dichloro-ethane; at 95℃; for 5h;Reflux; Green chemistry;Catalytic behavior;	General procedure: alpha-Alkenes were oxidized in a thermostat glass reactor (volume180 ml), equipped with reflux condenser and magnetic stirrer (n =500 min-1). Temperature 60-95 C was maintained with water thermostat with an accuracy of ±0.1 C. For reaction mixture preparation weighted catalyst sample was put into reactor, then, substrate was added and mixed with catalyst. After that 30% aqueous hydrogen peroxide was introduced, and heating was started. Catalysts II and III well dissolved in the substrate. Catalyst I was preliminarily dissolved in a small amount of 1,2-dichloroethane (1-2 ml). Reaction mixture was sampled in definite time intervals. For the purpose stirring was stopped. After organic and aqueous phases complete separation into layers (no longer than 20-30 s) sample from organic phase was taken. Carboxylic acid yield was determined using chromatography analysis via absolute calibration.

Reference： [1]Journal of the Chemical Society. Chemical communications,1990,p. 1467 - 1468
[2]Catalysis Communications,2017,vol. 88,p. 45 - 49
[3]Synthetic Communications,2003,vol. 33,p. 2945 - 2951
[4]Tetrahedron Letters,1989,vol. 30,p. 5781 - 5784
[5]Catalysis Communications,2012,vol. 17,p. 18 - 22
[6]Applied Organometallic Chemistry,2018,vol. 32
[7]Inorganic Chemistry,2018,vol. 57,p. 899 - 902

13
[ 15790-94-0 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen at 30℃; variation of reaction time and catalysts, selectivity, also with sodium salt;
	In methanol	15.A A. A. Decyl carboxylic acid Argon is bubbled through a solution of 1-decenylcarboxylic acid (1.6 g) in CH3 OH (20 ml) for 5 minutes. 10% Palladium on carbon is added and the mix is shaken on a Parr apparatus for 4 hours under H2. The mixture is filtered through Celite and evaporated to give the desired title saturated acid.
	In methanol	15.A A. A. Decyl carboxylic acid Argon is bubbled through a solution of 1-decenylcarboxylic acid (1.6 g) in CH3OH (20 ml) for 5 minutes. 10% Palladium on carbon is added and the mix is shaken on a Parr apparatus for 4 hours under H2. The mixture is filtered through Celite and evaporated to give the desired title saturated acid.

Reference： [1]Toshima, Naoki; Takahashi,Tadahito [Chemistry Letters, 1988, p. 573 - 576]
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US4604407, 1986, A
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - EP200377, 1991, B1

15
[ 112-37-8 ]
[ 37517-78-5 ]
[ 74631-91-7 ]

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

16
[ 2834-05-1 ]
[ 18120-63-3 ]
[ 112-37-8 ]
[ 112-38-9 ]
[ 505-56-6 ]
[ 94865-70-0 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 1948 - 1951

17
[ 627-90-7 ]
[ 64-17-5 ]
[ 112-37-8 ]

Reference： [1]Journal of the American Chemical Society,1991,vol. 113,p. 7697 - 7705

18
[ 109752-07-0 ]
[ 13831-30-6 ]
[ 112-37-8 ]
[ 109752-09-2 ]

Reference： [1]Synthesis,1987,p. 377 - 379

19
[ 112-37-8 ]
[ 77-78-1 ]
[ 1731-86-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 2481 - 2484

20
11,13-Dihydroxy-tetracosanoic acid methyl ester [ No CAS ]
[ 143-07-7 ]
[ 111-20-6 ]
[ 112-37-8 ]
[ 1852-04-6 ]

Reference： [1]Phytochemistry,1980,vol. 19,p. 75 - 78

21
[ 112-41-4 ]
[ 1119-87-5 ]
[ 112-44-7 ]
[ 112-37-8 ]
2,4-di-n-decyl-1,3-dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 32% 2: 6.4% 3: 5.2% 4: 2%	With ruthenium tetroxide In water; acetone at -70℃; for 0.166667h; Further byproducts given;

Reference： [1]Albarella, Laura; Piccialli, Vincenzo; Sica, Donato; Smaldone, Dina [Journal of Chemical Research, Miniprint, 1996, # 9, p. 2442 - 2456]

22
[ 593-08-8 ]
chromic acid [ No CAS ]
[ 112-37-8 ]
[ 64-19-7 ]

Reference： [1]Chemische Berichte,1879,vol. 12,p. 1669

23
[ 112-37-8 ]
[ 82410-32-0 ]
undecanoic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-undecanoyloxy-propyl ester [ No CAS ]

Reference： [1]Magnetic Resonance in Chemistry,2000,vol. 38,p. 696 - 700

24
[ 112-37-8 ]
[ 108-00-9 ]
N-[2-(dimethylamino)ethyl]undecanoic acid amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 8663 - 8667

25
[ 496-16-2 ]
[ 112-37-8 ]
1-(2,3-dihydrobenzofuran-5-yl)-undecan-1-one [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 405 - 408

26
[ 112-37-8 ]
[ 2244-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: oxalyl chloride / toluene / 0.5 h / 20 °C 2: aq. NaN₃ / acetone / 0.33 h / 0 °C 3: 69 percent / Li; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 2 h / 20 °C
	Multi-step reaction with 2 steps 1.1: Et₃N / acetonitrile / 0.5 h / 20 °C 1.2: 78 percent / O-benzotriazolyl-N,N,N',N'-tetramethyluronium BF₄ / acetonitrile / 1 h / 20 °C 2.1: 81 percent / Li; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 3 h / -78 °C
	Multi-step reaction with 2 steps 1.1: Et₃N / acetonitrile / 0.5 h / 20 °C 1.2: 67 percent / O-benzotriazolyl-N,N,N',N'-tetramethyluronium BF₄ / acetonitrile / 1 h / 20 °C 2.1: 62 percent / Li; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 3 h / -78 °C

	Multi-step reaction with 2 steps 1.1: Et₃N / acetonitrile / 0.5 h / 20 °C 1.2: 85 percent / O-benzotriazolyl-N,N,N',N'-tetramethyluronium BF₄ / acetonitrile / 1 h / 20 °C 2.1: 82 percent / Li; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 2 h / 20 °C
	Multi-step reaction with 2 steps 1.1: Et₃N / acetonitrile / 0.5 h / 20 °C 1.2: 80 percent / O-benzotriazolyl-N,N,N',N'-tetramethyluronium BF₄ / acetonitrile / 1 h / 20 °C 2.1: 70 percent / Li; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 3 h / -78 °C
	With Diethy phosphocyanidate; ammonia In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 4h;
	With Pseudoalteromonas tunicata TamA catalytic adenylation domain; ammonia; ATP; magnesium chloride In dimethyl sulfoxide Enzymatic reaction;

Reference： [1]Yus, Miguel; Radivoy, Gabriel; Alonso, Francisco [Synthesis, 2001, # 6, p. 914 - 918]
[2]Yus, Miguel; Radivoy, Gabriel; Alonso, Francisco [Synthesis, 2001, # 6, p. 914 - 918]
[3]Yus, Miguel; Radivoy, Gabriel; Alonso, Francisco [Synthesis, 2001, # 6, p. 914 - 918]
[4]Yus, Miguel; Radivoy, Gabriel; Alonso, Francisco [Synthesis, 2001, # 6, p. 914 - 918]
[5]Yus, Miguel; Radivoy, Gabriel; Alonso, Francisco [Synthesis, 2001, # 6, p. 914 - 918]
[6]Georgiades, Savvas N.; Clardy, Jon [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 10, p. 3117 - 3121]
[7]Marchetti, Piera M.; Richardson, Shona M.; Kariem, Noor M.; Campopiano, Dominic J. [MedChemComm, 2019, vol. 10, # 7, p. 1192 - 1196]

27
[ 112-37-8 ]
[ 19790-86-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2019
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1348 - 1358
[3]Tetrahedron,1999,vol. 55,p. 3657 - 3664

28
[ 112-37-8 ]
[ 629-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sulfuric acid 2: sodium ethylate / 115 - 120 °C / 15 - 20 Torr / und Zersetzen des 11-Oxo-heneicosan-carbonsaeure-⁽¹⁰⁾-aethylesters mit alkoh.KOH 3: amalgamated zinc; concentrated HCl

Reference： [1]Strating; Backer [Recueil des Travaux Chimiques des Pays-Bas, 1936, vol. 55, p. 903,914]

29
[ 112-37-8 ]
[ 26040-76-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With thionyl chloride; bromine; In methanol;	(I) Methyl 2-bromoundecanoate <strong>[112-37-8]Undecanoic acid</strong> (100 g, 0.54 mol) was added to thionyl chloride (108 ml, 1.48 mol) and this mixture was refluxed for 2 hours. Then, bromine (29 ml, 0.57 mol) was added dropwise over 1.5 hours under reflux. Reflux was continued for 5 additional hours. The resulting mixture was cooled to room temperature, methanol (250 ml, 6.1 mol) was added dropwise over 30 minutes, and this reaction mixture was left standing overnight After addition of aqueous NaC1, the product mixture was extracted twice with ether. The extract was washed with aqueous NaHCO3, aqueous Na2 SO3, and aqueous NaCl, and then dried. The solvent was removed in vacuo, giving crude methyl 2-bromoundecanoate (145 g, 97% yield). IR (neat) [cm-1 ]; 2920, 2850, 1736, 1432, 1144

Reference： [1]Patent: US4992455,1991,A

30
aqueous NaCl [ No CAS ]
[ 112-37-8 ]
[ 26040-76-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With thionyl chloride; bromine; In methanol;	(I) Methyl 2-bromoundecanoate <strong>[112-37-8]Undecanoic acid</strong> (100 g, 0.54 mol) was added to thionyl chloride (108 ml, 1.48 mol) and this mixture was refluxed for 2 hours. Then, bromine (29 ml, 0.57 mol) was added dropwise over 1.5 hours under reflux. Reflux was continued for 5 additional hours. The resulting mixture was cooled to room temperature, methanol (250 ml, 6.1 mol) was added dropwise over 30 minutes, and this reaction mixture was left standing overnight. After addition of aqueous NaCl, the reaction mixture was extracted twice with ether. The extract was washed with aqueous NaHCO3, aqueous Na2 SO3, and aqueous NaCl, and then dried. The solvent was removed in vacuo, giving crude methyl 2-bromoundecanoate (145 g, 97% yield). IR (neat) [cm-1 ]; 2920, 2850, 1736, 1432, 1144

Reference： [1]Patent: US5021435,1991,A

31
[ 112-37-8 ]
[ 60282-87-3 ]
[ 407-25-0 ]
17α-ethynyl-18-methyl-17β-undecanoyloxy-4,15-estradien-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In benzene;	EXAMPLE 8 17alpha-Ethynyl-18-methyl-17beta-undecanoyloxy-4,15-estradien-3-one From a solution of 4.0 g. of undecylic acid in 300 ml. of benzene, 50 ml. is distilled off. After cooling to room temperature, the mixture is combined with 4.5 ml. of trifluoroacetic acid anhydride. After 30 minutes, 4.0 g. of 17alpha-ethynyl-17beta-hydroxy-18-methyl-4,15-estradien-3-one is added thereto. The mixture is agitated for 2.5 hours, and the solution is worked up as described in Example 7. The crude product is chromatographed on silica gel with 18-25% ethyl acetate-hexane, thus obtaining 2.6 g. of 17alpha-ethynyl-18-methyl-17beta-undecanoyloxy-4,15-estradien-3-one as an oil.

Reference： [1]Patent: US4081537,1978,A

32
[ 112-37-8 ]
[ 153-98-0 ]
[ 1002100-48-2 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 6554 - 6569

33
[ 112-37-8 ]
[ 71941-72-5 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 6177 - 6179

34
[ 112-37-8 ]
[ 102522-47-4 ]
[ 1279697-31-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: undecylenic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Stage #2: 6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-amine With dmap In dichloromethane for 2h;

Reference： [1]Unciti-Broceta, Asier; Moggio, Loredana; Dhaliwal, Kevin; Pidgeon, Laura; Finlayson, Keith; Haslett, Chris; Bradley, Mark [Journal of Materials Chemistry, 2011, vol. 21, # 7, p. 2154 - 2158]

35
[ 1120-21-4 ]
[ 112-42-5 ]
[ 1653-30-1 ]
[ 765-04-8 ]
[ 112-44-7 ]
[ 112-37-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6727 - 6733

36
[ 1120-21-4 ]
[ 112-42-5 ]
[ 1653-30-1 ]
[ 112-44-7 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With CYP₁₅₃A Polaromonas sp. at 30℃; for 4h; Enzymatic reaction; regioselective reaction;

Reference： [1]Location in patent: scheme or table Scheps, Daniel; Honda Malca, Sumire; Hoffmann, Helen; Nestl, Bettina M.; Hauer, Bernhard [Organic and Biomolecular Chemistry, 2011, vol. 9, # 19, p. 6727 - 6733]

37
[ 1119-87-5 ]
[ 112-37-8 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5788 - 5791
[2]Synlett,2012,vol. 23,p. 2059 - 2062

38
C₆₁H₁₀₇NO₁₉ [ No CAS ]
[ 111-14-8 ]
[ 124-07-2 ]
[ 929-10-2 ]
[ 334-48-5 ]
[ 112-37-8 ]
[ 2724-56-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₆₁H₁₀₇NO₁₉ With hydrogenchloride; methanol at 80℃; for 12h; Sealed tube; Stage #2: With potassium permanganate; sodium periodate; potassium carbonate In <i>tert</i>-butyl alcohol at 37℃; for 18h; Stage #3: With sulfuric acid In <i>tert</i>-butyl alcohol	4.8.5. Microscale oxidation of fraction B Compound 4 (100 μg) dissolved in 500 μL of 1 M HCl in 95% MeOH was incubated for 12 h at 80 °C in a sealed tube. The reaction mixture was dried under N2 flow and the resulting material was partitioned between CHCl3 (2 mL) and 20% MeOH (2 mL). Both layers were dried by N2 flow to deliver fraction A (from the 20% MeOH layer) and fraction B (from the CHCl3 layer). This process was also scaled to 1 mg of 4. Fraction B obtained from the methanolysis of 400 μg of 4 was dissolved in t-BuOH (150 μL) and treated by the sequential addition of 40 mM K2CO3 (25 μL), 25 mM KMnO4 (100 μL) and 100 mM NaIO4 (100 μL). The mixture was warmed to 37 °C in a sealed vial. After 18 h, the mixture was acidified with 5 M H2SO4 and decolorized by the addition of a saturated solution of Na2SO3. The mixture was diluted with 1 mL of H2O and extracted with Et2O (3 × 3 mL). The combined extracts were dried with Na2SO4. The resulting solution was treated with 2 M TMSCHN2 in Et2O (250 μL) for 1 h at rt at which point it was concentrated to ∼200 μL by rotary evaporation. The resulting solution was evaluated by GC/MS. The results were as follows: methyl-heptanoate with tR = 2.5 min and M+ at m/z 144, methyl-6-methylheptanoate, tR = 3.6 min, M+ at m/z 158, methyl-octanoate, tR = 4.4 min with M+ at m/z 158, methyl-decanoate, tR = 6.8 min with M+ at m/z 186, methyl-undecanoate, tR = 7.3 min with M+ at m/z 200, methyl-10-methylundecanoate, tR = 8.1 min with M+ at m/z 214 and methyl-dodecanoate with tR = 8.9 min, M+ at m/z 214. Relative abundances were determined by peak integration and were compared to a quantitative 1:1:1:1 mixture containing methyl-heptanoate, methyl-undecanoate, methyl-6-octanoate and methyl-dodecanoate. These results are summarized in Figure 8.

Reference： [1]Location in patent: experimental part La Clair, James J.; Rodriguez, Abimael D. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 22, p. 6645 - 6653]

39
[ 112-37-8 ]
[ 1232884-73-9 ]
[ 1232885-00-5 ]

Yield	Reaction Conditions	Operation in experiment
63%		To a solution of undecanoic acid (133 mg, 0.71 mmol) in DMF (1 mL) were added PyBOP (407 mg, 0.78 mmol), DIPEA (619 muL, 3.55 mmol) and the reaction mixture was stirred for 30 min. Compound 5 was then added (275 mg, 0.64 mmol) and the reaction mixture was stirred for 13 h at room temperature. After standard work-up, the crude product was purified by flash column chromatography (hexane/ethyl acetate 90:10) to get the desired product. Yield 63%.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 2405 - 2415

40
[ 112-63-0 ]
[ 143-07-7 ]
[ 38199-50-7 ]
[ 25152-84-5 ]
[ 111-11-5 ]
[ 334-49-6 ]
[ 112-37-8 ]
[ 15790-93-9 ]
[ 1931-63-1 ]
[ 65114-83-2 ]
[ 66-25-1 ]

Yield	Reaction Conditions	Operation in experiment
	In glycerol; at 180℃; for 15h;	General procedure: An aliquot of 2 +/- 0.01 g of MO or ML were weighed directly into standard glass tubes (200 mm x 12 mm i.d.). The tubes were introduced into a Rancimat vessel containing 8 g of glycerol to facilitate heat transfer, and in turn inserted in the heating block of a Rancimat device previously heated at 180 +/- 1 C. The reaction vessels were left open during heating and bubbling of air was not applied. After 15 h-heating, samples were taken out, shaken, and kept at -20 C until analyses.

Reference： [1]Chemistry and Physics of Lipids,2012,vol. 165,p. 338 - 347

41
[ 112-37-8 ]
[ 35903-52-7 ]
[ 1399361-47-7 ]

Yield	Reaction Conditions	Operation in experiment
36%	With dicyclohexyl-carbodiimide;dmap; In dichloromethane; at 20℃;	Example 12(Compound 216)[0139] 0.28g (1.0 mmol) of fumagillol, 0.19g (1.0 mmol) of undecanoic acid acid, and 0.01 lg (0.1 mmol) of DMAP are dissolved in 5mL of dry CH2CL2. DCC (0.21g, 1.0 mmol) dissolved in 5mL of dry CH2CL2 is added drop wise over 5 minutes with stirring at room temperature. After addition is complete the mixture is allowed to stir overnight and then diluted with 50mL of CH2CL2 , washed with 50mL of water followed by 50 mL of brine, dried over Na2S04 and condensed in vacuo. Purification by biotage flash chromatography (Si02, EtOAc/Hexanes gradient) affords 160 mg (36%) of the title compound.

Reference： [1]Patent: WO2012/122264,2012,A1 .Location in patent: Page/Page column 55

42
[ 112-37-8 ]
[ 1362243-98-8 ]
[ 1426303-67-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 20℃; for 0.5h;	General procedure: To a mixture of amine 6 (1 mmol) and carboxylic acids 7a-n (1.1 mmol) in methanol (10 mL) was added 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) (1.1 mmol). The reaction mixture was stirred at room temperature for 30 min. The solvent was removed under reduced pressure, and then the residue was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography to give N-[3-(1-methoxy-2-naphthyl)-2,2-dimethylpropyl]amide (8a-n). All spectroscopic data of compounds 8a-n are shown in the Supplementary data.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 60,p. 271 - 284

43
[ 112-37-8 ]
[ 171522-35-3 ]
[ 1207286-27-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;	General procedure: To a solution of carboxylic acid (1.3 mmol) and 4-dimethylaminopyridine (DMAP) (0.3 mmol) in dry dichloromethane (10 mL) was added naphthoquinone alcohol 17 (1 mmol) in dry dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 5 min when a solution of 1,3-dicyclohexylcarbodiimide (DCC) (1.3 mmol) in dry dichloromethane (15 mL) was added. Stirring was continued overnight at room temperature. The precipitate of dicyclohexylurea was filtered off and the filtrate washed with saturated ammonium chloride solution then water. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica gel) to give the target product, naphthoquinone aliphatic esters.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 60,p. 271 - 284

44
[ 112-37-8 ]
[ 546-67-8 ]
[ 71-43-2 ]
[ 124-18-5 ]
[ 1534-32-3 ]
[ 60826-18-8 ]
[ 7433-78-5 ]
[ 7433-56-9 ]
[ 872-05-9 ]
[ 19150-21-1 ]
[ 112-17-4 ]
[ 60826-16-6 ]
[ 19398-88-0 ]
[ 19398-89-1 ]
[ 19398-86-8 ]
[ 20348-51-0 ]
[ 20063-97-2 ]
[ 104-72-3 ]
(+/-)-decan-4-yl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 81℃;	2.2. Oxidative lead(IV)acetate decarboxyla tion of alkanoic acids General procedure: The thermal LTA decarboxylation in benzene was performed as described previously [21]. Mixture of 10 mmol of LTA and 10 mmol of alkanoic acids (nonanoic,undecanoic or tetradecanoic acid) was dissolved in 60 cm 3 of benzene. Before starting the oxidative decompo sition slow stream of purified Ar was introduce d into stirred mixture of acid and LTA in benzene for 30 min at room temperature and in the absence of light.The oxygen-free mixture resulting from the above described procedure [21] was stirred and heated under reflux (withoutlight protection) until completion (i.e. until disappearance of tetravalent lead which was monitored by potassium iodide/strach paper tracks)and then worked up. After completion of the LTA oxidation,the mixture was cooled,treated with 50 cm 3 of diethyl ether and filteredoff.The filtrate was washed with water, diluted HCl (1:1),aqueous Na2CO3 (5%) and water. After drying (CaSO4), the solvents were removed under reduced pressure and the products in the residue were analyzed by analytical gas chromatograp hy and separated by preparative gas chromatography. The results of all runs are given in Tables 1, 3 and 4.

Reference： [1]Teodorović, Aleksandar V.; Badjuk, Dalibor M.; Stevanović, Nenad; Pavlović, Radoslav Z. [Journal of Molecular Structure, 2013, vol. 1040, p. 19 - 24]

45
[ 1427084-94-3 ]
[ 112-37-8 ]
[ 627-90-7 ]

Reference： [1]Patent: US2013/66089,2013,A1

46
[ 1427084-95-4 ]
[ 112-37-8 ]
[ 627-90-7 ]

Reference： [1]Patent: US2013/66089,2013,A1

47
[ 539-88-8 ]
[ 112-37-8 ]
[ 627-90-7 ]

Reference： [1]Patent: US2013/66089,2013,A1

48
[ 1427084-96-5 ]
[ 112-37-8 ]
[ 627-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; In ethanol; water; at 230℃; under 25066.7 Torr;	To prepare the hydrodeoxygenation catalyst, incipient wetness was used to impregnate silica-alumina (SiAl; Siralox 80/300) support with platinum (Pt). To 4 g of support, a solution of 5.20 g of water and 0.0801 g of tetraamine platinum (II) nitrate (Aldrich) was added dropwise under constant stirring. The resulting mixture was heated at 130 C. for about 12 hours in an oven. The dried sample was calcined under dry air flowing at a rate of about 50 mL/min by raising the temperature from room temperature, about 25 C. as used herein, to 450 C. at 175 C./hour and holding for 3 hours. After calcination, 1.5 g of 1% Pt on SiAl was loaded on a one-quarter inch stainless steel tube flow reactor and heated from room temperature to 450 C. over 8 hours under 25 mL/min (GHSV of ?500 hr-1) of flowing hydrogen gas at atmospheric pressure. [0042] Ethyl 4-hydroxy-6-(5-methyltetrahydrofuran-2-yl)hexanoate (5 g) was dissolved in 45 g of water and 30 g of ethanol. At a liquid flow rate of 0.02 mL/min (LHSV?0.4 hr-1), a temperature of 230 C., and pressure of 470 psig of hydrogen, a spontaneously separating organic phase containing ethyl undecanoate was collected. From 32 g of feed into the system, 1.34 g of organic phase was collected. GCMS analysis of the organic phase and comparison with NIST standards revealed the organic composition contained the following components (GCMS area %): decane (0.07%), undecane (0.53%), undecanol (0.78%), decane ethyl ester (0.67%), undecanoic acid/undecanoic ethyl ester (60.1%, mostly ethyl ester), and some unidentified peaks (37.85%).

Reference： [1]Patent: US2013/66089,2013,A1 .Location in patent: Paragraph 0041

49
[ 620-02-0 ]
[ 112-37-8 ]
[ 627-90-7 ]

Reference： [1]Patent: US2013/66089,2013,A1

50
[ 63375-50-8 ]
[ 112-37-8 ]
[ 1257852-19-9 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 20h;	<strong>[112-37-8]Undecanoic acid</strong> (2,2-bis-hydroxymethyl-3-undecanolylamino-propyl)-amide (2). Compound 2 was synthesized according to Scheme 1 above. 2,2-Bis-aminomethyl-propane-1,3-diol (1)2 (0.51 g, 3.8 mmol), undecanoic acid (1.42 g, 7.6 mmol), 1-hydroxybenzotriazole monohydrate (HOBt) (1.2 g, 9.1 mmol) was dissolved in anhydrous DMF (30 mL). Diol 1 can be prepared according to literature procedures (Virta et al., J. Org. Chem. 69, 2008-2016 (2004)). 1-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (1.7 g, 0.91 mmol) was added in small portions at 0 C. and the resulting solution left stirring at room temperature for 20 hours. The solution was taken up with EtOAc (100 mL) and was washed successively with a 1 M aqueous NaHCO3 solution (100 mL), a 0.1 M aqueous HCl solution (100 mL) and brine (2×100 mL). Then the organic layer was dried with anhydrous Na2SO4 and the solvent was removed by rotary evaporation. The reaction mixture was precipitated with ether (100 mL) and the resulting solid was collected and dried in vacuo to afford amide-containing diol 2 as a white solid (1.63 g, 91%). This product was used for next reaction without further purification. (0092) Diol 2: 1H NMR (300 MHz, CDCl3): delta 6.97 (t, J=6.8 Hz, 2H), 4.65 (t, J=6.6 Hz, 2H), 3.27 (d, J=7.0 Hz, 4H), 3.01 (d, J=7.0 Hz, 4H), 2.25 (t, J=7.4 Hz, 2H), 1.64 (quin, 4H), 1.30-1.23 (m, 28H), 1.38-1.21 (m, 6H), 0.88 (t, J=7.0 Hz, 6H); 13C NMR (75 MHz, CDCl3): delta 176.1, 61.0, 46.6, 38.3, 36.9, 32.1, 29.8, 29.7, 29.5, 26.2, 22.9, 14.3; HRMS (ESI): calcd. for C27H54N2O4 [M]+471.4157, found 471.4154

Reference： [1]Patent: US8530631,2013,B2 .Location in patent: Page/Page column 21

51
[ 112-37-8 ]
[ 477-47-4 ]
[ 1453805-81-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 72h;	Example 5 (5R.5aR.8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9- hexahvdrofuror3',4':6,71naphthor2,3-diri,31dioxol-5-yl undecanoate PPP (41 mg, 0.1 mmol), DMAP (6 mg, 0.05 mmol) and the undecanoic (23 mg, 0.09 mmol) acid were weighed in a vial. Dry dichloromethane (1.5 mL) was added and EDC- HCI (23 mg, 0.12 mmol) was added at room temperature. The reaction mixture was stirred for three days. More dichloromethane was added and the solution was washed with 0.1 M HCI (aq), saturated NaHC03 and brine. The crude product (55 mg) was purified by flash chromatography using 2-4% methanol in dichloromethane to give the title compound in 77% yield (45 mg) and 96% purity according to LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mL/min), MS ESI+ m/z 397, rt 3.107.

Reference： [1]Patent: WO2013/132262,2013,A1 .Location in patent: Page/Page column 20

52
C₂₂H₄₅NO₃ [ No CAS ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate; sulfuric acid; In acetone; at 20℃;	General procedure: Compound 1b (0.8 mg) was dissolved in 10% H2SO4 and acetone (2.0 mL each). KMnO4 (50 mg) was then added to the solution and stirred overnight at room temperature [16,20]. The reaction was then quenched with aqueous Na2S2O3 (5%). After removal of acetone, the reaction mixture was extracted with Et2O. The Et2O layer was dried over Na2SO4 and concentrated to yield the residue, which was methylated using CH2N2 in Et2O at 0 C [20]. The reaction mixture was kept in ice for 30 min before being allowed to stand at room temperature overnight. This procedure resulted in compound 1c (0.4 mg), which was identified as methyl nonanoate by GC-MS.

Reference： [1]Molecules,2013,vol. 18,p. 11241 - 11249

53
[ 112-37-8 ]
[ 2065-37-4 ]
[ 1504583-91-8 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9530 - 9541

54
[ 112-37-8 ]
[ 1376134-24-5 ]
C₂₉H₃₅NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; acetonitrile; at 90℃; for 0.583333h;	General procedure: 150 muL standard fatty acid mixtures, 200 muL BCETS and 100 muL DMF were added orderly to a 2 mL vial containing 15 mg K2CO3. The vial was sealed and allowed to react in a water bath at 90 C for 35 min. 100muL supernatant obtained above was removed to dry under a stream of nitrogen gas in a 2 mL vial and then 15 mg K2CO3, 200 muL BCETS and 100 muL DMF were added orderly into the vial. The vial was sealed and allowed to react in a water bath at 90 C for 35 min. After the reaction was completed, the mixture was cooled to room temperature. The derivatization solution was syringe filtered using a 0.22 mm nylon filter and injected directly into the chromatograph column. The injected volume was 10 muL. The derivatization procedure of fatty acids with BCETS was shown in Fig. 2.

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 103 - 109
[2]Asian Journal of Chemistry,2015,vol. 27

55
[ 706-14-9 ]
[ 37810-94-9 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With samarium diiodide; water In tetrahydrofuran at 20℃; for 3h; Schlenk technique; Inert atmosphere; Overall yield = 6 %Spectr.;

Reference： [1]Szostak, Michal; Spain, Malcolm; Procter, David J. [Journal of the American Chemical Society, 2014, vol. 136, # 23, p. 8459 - 8466]

56
[ 112-37-8 ]
29-deacetylsendanin [ No CAS ]
C₄₁H₅₈O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20℃;	General procedure: A mixture of 1 (0.17 mmol), fatty acids RCO2H (0.2mmol), N,N'-diisopropylcarbodiimide (DIC, 0.31 mmol), and 4-dimethylaminopyridine (DMAP, 0.04 mmol) in CH2Cl2(10 mL) was stirred at room temperature. The completion of reaction was checked by TLC analysis. After 3.5-24 h, water(10 mL) was added to the mixture, which was extracted with CH2Cl2 (30 mL 3). Then the combined organic phase was washed by brine (30 mL), dried over anhydrous Na2SO4, concentrated, and purified by PTLC to give the products 3a-r in 14-88% yields.

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2013,vol. 16,p. 394 - 399

57
[ 15243-33-1 ]
[ 112-37-8 ]
[ 603-35-0 ]
Ru2(CO)4(μ2-η2-O2CC11H23)2(triphenylphosphine)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%		General procedure: A solution of Ru3(CO)12 and three equivalents of the appropriate fluorinated fatty acids indry tetrahydrofuran (20 mL) was heated at 110 C in a pressure Schlenk tube for 15 h.Then, addition of three equivalents of the axial ligand [(L =NC5H5); (L= PTA); (L= PPh3)]under stirring at room temperature for 2 h afforded the final products. After evaporation ofthe tetrahydrofuran, the complexes were isolated from the residue by precipitation fromdichloromethane/pentane. In order to improve the purity, the crude products were subjectedto chromatography on silica gel using a dichloromethane/pentane mixture as eluent (for 1band 2b a dichloromethane/ethanol mixture was used), and the solid obtained was driedunder vacuum.

Reference： [1]Journal of Coordination Chemistry,2013,vol. 66,p. 1753 - 1762

58
[ 112-37-8 ]
[ 100-46-9 ]
[ 544431-24-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 2,4,6-tris(2,2,2-trifluoroethoxy)-1,3,5-triazine; In acetonitrile; at 60℃; for 4h;Inert atmosphere;	General procedure: Stirrer a solution ofcarboxylic acids (5 mmol), amines (5 mmol) and TriTFET (5 mol %) in 15 ml acetonitrileat 60 0C. The reaction mixture was stirred until the reaction wascomplete, as monitored by TLC. The residue was dissolved with EtOAc (30ml) andwashed with saturated NaHCO3, water and brine. The organic layer wasdried over MgSO4. Filtered and concentrated under reduced pressureand got corresponding product in good yield.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 1960 - 1963

59
[ 112-37-8 ]
[ 26687-82-1 ]
arctigenin undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20℃; for 6h;	Into 10 mL of chloroform were dissolved 75 mg (0.2 mmol) of <strong>[26687-82-1]arctigenin</strong> and 37.3 mg (0.2 mmol) of undecanoic acid. Thereto were added 76.68 mg (0.4 mmol) of the water-soluble carbodiimide and 48 mg (0.4 mmol) of DMAP. In chloroform, the reactive components were caused to react with each other at room temperature for 6 hours. Water was added to the reaction liquid, and this system was stirred. The resultant organic layer was then washed with 1 N HCl, and a saturated solution of NaHCO3 in water. The chloroform layer was distilled off under a reduced pressure to yield <strong>[26687-82-1]arctigenin</strong> undecanoate.

Reference： [1]Patent: US2015/93345,2015,A1 .Location in patent: Paragraph 0118

60
[ 112-37-8 ]
C7β-Hydroxyobacunone [ No CAS ]
C₃₇H₅₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;	General procedure: A mixture of the corresponding carboxylic acids R3CO2H(0.18 mmol), compound 3 (0.13 mmol), N,N?-dicyclohexylcarbodiimide(DCC, 0.16 mmol), and 4-dimethylaminopyridine (DMAP, 0.026 mmol) in dry CH2Cl2(10 mL) was stirred at room temperature. When the reaction was completeaccording to TLC analysis, the mixture was diluted with CH2Cl2(30 mL). Then the mixture was sequentially washed by water (15 mL), aq. HCl(0.1 mol/L, 15 mL), 5% aq. Na2CO3 (15 mL) and brine (15 mL).Finally, the organic phase was dried over anhydrous Na2SO4,concentrated in vacuo, and purified by PTLC to give the pure target products, C7beta-acyloxybacunone(5a-e?), in 40-97% yields.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 25 - 29

61
[ 112-37-8 ]
[ 120-20-7 ]
N-(3,4-dimethoxy-β-phenylethyl)dodecanamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3968 - 3971

62
[ 112-37-8 ]
[ 590-17-0 ]
2-cyanomethylundecanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%		THF (30 mL) was added to a stirred solution of n-butyl lithium (2.5 M in hexane, 9.4 mL, 23.5 mmol) at -78C. To this solution was added diethylamine (0.5 mL, 4.8 mmol) over 2 minutes. The solution was warmed to 0C for 15 minutes then recooled to -78C. A solution of undecanoic acid (2.0 g, 10.7 mmol) in THF 20ml) was added over 20 minutes. The resulting mixture was warmed to 0C for 30 minutes to give a solution. The solution was recooled to -78C and then to this stirred mixture was added a solution of bromoacetonitrile (0.75 mL, 10.7 mmol) in THF (10 mL) over 25 minutes. The mixture was stirred at -78C for 30 minutes then warmed to ambient temperature and left to stir for 21 h. After this time, the mixture was quenched with the slow addition of water (250 mL) to give a mixture with pH 14. The mixture was extracted with diethyl ether (2 x 150 mL), adding some brine to minimize emulsions. These extracts were discarded. The aqueous phase from the extraction was acidified to pH 1 with cone hydrochloric acid (approx. 1 .5 mL) and extracted with ethyl acetate (2 x 150 mL). The emulsion formed during the extraction was clarified by filtration through Celite. The organic extracts were dried (MgSC ) and evaporated in vacuo to a brown oil. The oil was purified by column chromatography over silica gel eluting with a gradient of acetone/toluene to give the title product as an off -white solid (0.36 g, 1 .6 mmol, 15%), m/z 226 (MH+). C13H23NO2 exact mass 225.17.

Reference： [1]Patent: WO2015/135976,2015,A1 .Location in patent: Page/Page column 78

63
6-O-undecanoyl-α,β-trehalose [ No CAS ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
95%		A solution of compound 1 (10 mg) in 95% EtOH (2 mL) and 5% NaOH (2 mL) was refluxed for3 h. After cooling, the mixture was diluted to 10 mL, acidified to pH 5 with dilute HCl andextracted with CHCl3. Concentration of the CHCl3 extract yielded undecanoic acid (2.60 mg,95%), which was identical with the authentic sample. The aqueous solution was concentrated todryness and acetylated with Ac2O/pyridine/DMAP to produce a,b-D-trehalose octaacetate,which was also identical with the authentic sample (TLC, IR, [a ]D and NMR).3.5.1. Undecanoic acidWhite solid; Rf 0.52; petroleum ether-ethyl acetate, 10:1. IR (KBr) vmax (cm21): 2922, 2853,2673, 1710, 1464, 1411, 1377, 1364, 1286, 1240, 1221, 936, 720, 624, 480; 13C NMR (CDCl3,75MHz): 14.0, 22.7, 24.2, 29.1, 29.2, 29.3, 29.4, 29.7, 31.0, 34.0, 179.2

Reference： [1]Natural Product Research,2014,vol. 28,p. 1613 - 1618

64
[ 1002-69-3 ]
[ 124-38-9 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
55%	With nickel(II) bromide dimethoxyethane; manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; tetrabutylammomium bromide In N,N-dimethyl-formamide at 60℃; Schlenk technique;

Reference： [1]Börjesson, Marino; Moragas, Toni; Martin, Ruben [Journal of the American Chemical Society, 2016, vol. 138, # 24, p. 7504 - 7507]

65
[ 544-76-3 ]
[ 143-07-7 ]
[ 124-07-2 ]
[ 112-05-0 ]
[ 334-48-5 ]
[ 112-37-8 ]
[ 638-53-9 ]
[ 544-63-8 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 6649 - 6656

66
[ 112-37-8 ]
[ 129453-61-8 ]
C₄₃H₆₇F₅O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27.7%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 48h;	1) Reaction Treatment (0048) 3 g (4.95 mmol) fulvestrant was added into a 250 mL round-bottom flask and dissolved with 160 mL methylene chloride while stirring. Then 0.0822 g (0.66 mmol) DMAP, 0.96 g (5.05 mmol) undecanoic acid and 1.02 g (4.98 mmol) DCC was added sequentially into said flask. After reacting under stirring at room temperature (e.g., 20±5) for 48 h, the reaction was stopped. (0049) 2) Post Process (0050) The reaction system was first frozen to precipitate as much reaction by-product DCU as possible. After being filtered to remove solid DCU, the filtrate was washed with saturated sodium bicarbonate solution, then washed with water to neutral and evaporated by rotary evaporator to remove methylene chloride, to give colorless and clear colloidal liquid, which was dissolved in a small amount of ethyl acetate and then froze in a refrigerator (e.g., the freezing temperature may be -15±3 C.) until no white solid DCU precipitated out. The filtrate was concentrated to remove ethyl acetate, recrystallized from mixed solvent of n-hexane-ethyl acetate, and then filtered to remove white solid precipitated out (unreacted raw material fulvestrant). The mother liquor was spin-dried to give colorless oily matter. Said oily matter was further purified by silica-gel column chromatography (the eluent was n-hexane-ethyl acetate (1:1, volume ratio)) and was then evaporated by rotary evaporator to give 1.0611 g colorless oily matter, which was Compound I (purity 99.104% as determined by HPLC according to the same determination method in Example 1), and the molar yield was 27.7%. (0051) IR (cm-1): 3385, 2926, 2855, 1756, 1494, 1463, 1199, 1152, 1059, 1017, 985, 721. (0052) 1HNMR (500 MHz, CDCl3, ppm): delta 7.28 (s, 1H), 6.83 (d, 1H), 6.77 (d, 1H), 3.73 (t, 1H, J=8 Hz), 2.88-1.17 (t, 57H), 0.89 (s, 3H), 0.77 (s, 3H). (0053) 13CNMR (125 MHz, CDCl3, ppm): delta 172.64, 148.52, 137.13, 126.91, 122.37, 120.10, 118.64, 81.93, 52.75, 51.03, 46.47, 43.33, 41.67, 38.23, 36.89, 34.50, 34.45, 33.85, 31.89, 29.67, 29.50, 29.63, 29.55, 29.49, 29.46, 29.34, 29.30, 29.26, 29.16, 29.12, 28.80, 28.23, 27.11, 25.70, 25.01, 24.88, 22.66, 14.62, 14.50, 11.50.

Reference： [1]Patent: US2016/60288,2016,A1 .Location in patent: Paragraph 0047-0053

67
[ 112-37-8 ]
[ 1415695-51-0 ]
(S)-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)undecanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 3h;Inert atmosphere;	General procedure: Compound 11 (283 mg, 0.6 mmol) and the appropriate acid(1.2 mmol) were dissolved under N2 in dry CH2Cl2 (60 mL) andtreated with N,N'-dicyclohexylcarbodiimide (743 mg, 3.6 mmol)and 4-(N,N-dimethylamino)pyridine (147 mg, 1.2 mmol). The mixture was stirred for 3 h at room temperature and then filteredthrough Celite. The filtratewas evaporated under reduced pressure,and the residue was subjected to column chromatography on silicagel (EtOAc-acetone, 8:1) to afford the desired compound 1-10. Thephysical and spectral data are indicated in the SupplementaryInformation.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 126,p. 526 - 535

68
[ 112-37-8 ]
[ 92-88-6 ]
4-n-undecanoyloxy-4'-hydroxy-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%		General procedure: To a stirred solution of 1.86 g (10 mmol) of 4,4-dihydroxybiphenyl (biphenol) in 10 ml THF, 50 mg (0.4 mmol) of DMAP and 10 mmol of carboxylic acid were added. After the mixture was stirred for 5 min, 1.26 g (10 mmol) of DIC was added into the mixture, and then, the final reaction mixture was stirred under nitrogen purge for 3 h at room temperature through Steglich esterification. Insoluble solids, primarily precipitated urea, were then filtered off, and the filtrate was concentrated by a rotary evaporator until complete solvent removal. The residue was dissolved in a small amount of CHCl3 and purified by a silicagel column, using CHCl3 as an eluent to remove residual reactants and side reaction compounds.

Reference： [1]Molecular Crystals and Liquid Crystals,2016,vol. 633,p. 123 - 128

69
[ 112-37-8 ]
[ 616-38-6 ]
[ 1731-86-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; at 160℃; for 5h;Autoclave; Green chemistry;	General procedure: Into a stainless steel pressure microreactor of capacity 17 mL was charged 5 wt % of zeolite NaY-Bf, 100 mmol of carboxylic acid, and 300-400 mmol of dimethyl carbonate, the reactor was hermetically closed, and the reaction mixture was heated at 180-200C for 5 h. On completion of the reaction the reactor was cooled to room temperature, opened, the reaction mixture was filtered through a bed of Al2O3. Unreacted dimethyl carbonate was distilled off, the residue was distilled at atmospheric pressure or in a vacuum, or it was crystallized from ethanol.

Reference： [1]Russian Journal of Organic Chemistry,2017,vol. 53,p. 163 - 168
Zh. Org. Khim.,2017,vol. 53,p. 177 - 181,5

70
[ 3913-02-8 ]
[ 112-37-8 ]
2-butyloctylundecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		21 Preparation of 2-butyloctyl undecanoate Example 21 Preparation of 2-butyloctyl undecanoate 2-butyloctanol (16 g, 0.0890 mol, MW: 186.3), undecanoic acid (10 g 0.0537 mol, MW: 186.3) and titanium (VI) isopropoxide (0.763 g, 0.00267 mol, MW: 284.22) were mixed 75 ml toluene in three necked round bottom flask along with a dean-stark apparatus. Then solution was reflux for overnight (18 h). In 18 hours, ˜1.5 ml water was collected in the trap. Toluene was removed by simple distillation at 50° C. and excess of 2-butyloctanol was distilled with air bath oven at 200° C. under high vacuum and filter through celite. The isolated product was characterized by 1HNMR. Yields: 18.5 g (97%),

Reference： [1]Current Patent Assignee: EXXON MOBIL CORP - US2017/183595, 2017, A1

71
[ 104-67-6 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium 10% on activated carbon; W(OTf)6; hydrogen; at 135℃; under 760.051 Torr; for 12h;	General procedure: Specific methods are as follows: propiolactone was added (0.36g, 5mmol), palladium on carbon (10%, 26.5mg, 0.025mmol, 0.5mol%) in the reactor and W (OTf)6(107.8mg, 0.1mmol, 2mol%). A hydrogen balloon connected to the top of the reactor, and the reactor was purged with hydrogen gas atmosphere. Hydrogen atmosphere at normal pressure, the reaction was stirred at 135 deg.] C after 12h, detected by gas, gamma- valerolactone complete conversion of starting material, and only n-valeric acid. The method carried out as follows completion of the hydrogenation reaction of the ring-opening reaction system separation, to obtain the desired product n-valeric acid: The reaction was completed reaction mixture was dissolved with methylene chloride, filtered to remove the palladium on carbon catalyst and W (OTf)699% yield measured propionic acid, purity of the product was 99%. NMR data for the product using the embodiment of the present invention is the NMR identified the product as follows:he specific reaction procedure and the operation method were the same as in Example 27, the yield was 90%, and the purity of the product was 99%. On the product The NMR data were used in the manner described in the present invention. The NMR data of the product were as follows:

Reference： [1]Organic Letters,2019,vol. 21,p. 7099 - 7103
[2]Patent: CN106831389,2017,A .Location in patent: Paragraph 0113; 0141-0143
[3]ACS Catalysis,2017,vol. 7,p. 7520 - 7528

72
[ 112-37-8 ]
[ 15790-94-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: undecylenic acid With Zn(2,2,6,6-tetramethylpiperidine)_2*2LiCl; zinc(II) chloride In tetrahydrofuran at -40℃; for 1.5h; Inert atmosphere; Sealed tube; Stage #2: With bis(η3-allyl-μ-chloropalladium(II)); Allyl acetate In tetrahydrofuran at -40 - 60℃; for 12h; Inert atmosphere; Sealed tube; diastereoselective reaction;

Reference： [1]Zhao, Yizhou; Chen, Yifeng; Newhouse, Timothy R. [Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13122 - 13125][Angew. Chem., 2017, vol. 129, # 42, p. 13302 - 13305,4]

73
[ 638-53-9 ]
[ 112-37-8 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 13122 - 13125
Angew. Chem.,2017,vol. 129,p. 13302 - 13305,4

74
[ 112-37-8 ]
[ 74-89-5 ]
[ 204777-78-6 ]
Fmoc-L-lysine(pg)-OH [ No CAS ]
C₃₀H₆₁N₇O₄ [ No CAS ]

Reference： [1]Nature Communications,2018,vol. 9

75
[ 112-37-8 ]
[ 204777-78-6 ]
Fmoc-L-lysine(pg)-OH [ No CAS ]
C₂₉H₅₉N₇O₄ [ No CAS ]

Reference： [1]Nature Communications,2018,vol. 9

76
[ 112-37-8 ]
[ 39994-75-7 ]
methyl undecanoyl-L-threoninate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		General procedure: A mixture of 10.25 mmol of L-threonine methyl ester hydrochloride (1) and Et3N (2 mL) was dissolved in ice-cold anhydrous dichloromethane (40 mL) and kept in ice for 20 min with stirring. This was followed by the addition of acid (12.3 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC.HCl, 12.3 mmol) and hydroxy benzotriazole (HOBt, 15.38 mmol) successively at 0 C. The mixture was left at room temperature for 12 h under magnetic stirring. The reaction was monitored using micro TLC (hexane: ethyl acetate, 1:1, v/v). At the end of the reaction, the reaction mixture was dissolved in chloroform (75 mL) and then it was washed by 5% NaHCO3 solution, saturated NaCl solution successively. The chloroform layer was dried with anhydrous Na2SO4 and the filtrate was dried under vacuum. The crude mixture was purified by silica-gel chromatography by using hexane, ethyl acetate solvent mixture to get the title compound with 78-84% yield.

Reference： [1]Medicinal Chemistry Research,2018,vol. 27,p. 285 - 307

77
[ 112-37-8 ]
[ 99755-59-6 ]
rotigotine undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.5%		Weigh the purified undecanoic acid(2.95 g, 15.83 mmol, 1.0 eq) was placed in a 250 mL eggplant-shaped flask containing approximately 100 mL of anhydrous dichloromethane, and subjected to an oil bath at 30 C.EDC·HCl (3.64 g, 18.99 mmol, 1.2 eq), DMAP (0.77 g, 6.30 mmol, 0.4 eq) and SOCl2 (1723mu) were added.L, 23.73 mmol, 1.5 eq), after stirring, add 2 drops of DMF catalysis, continue stirring for 2 h, and reflux at 50 C for 2 h. 40 C rotary steaming, waitingAfter the near spin, a small amount of toluene was added, and the mixture was again dried, and the operation was repeated once to obtain an acid chloride product. Add a small amount of dichloromethane to it.After re-dissolving the alkane, pre-dissolved rotigotine (5.00 g, 15.85 mmol, 1.0 eq) was added and TEA (6.6 mL,47.45 mmol, 3.0 eq), EtOAc (EtOAc) m. Reaction stopThen, add 100 mL of 0.1 M Na2HCO3 solution, stir for 10 min, separate the organic layer, repeat the operation twice (2 × 100 mL),The machine layer was washed three times with saturated NaCl solution, and the water was removed by anhydrous Na2SO4. The filtrate was filtered with suction, and the solvent was removed by evaporation at 40 C.The methylene chloride was redissolved, washed with water, dehydrated, and then evaporated to give a brown oily solid, which was dried at 50 C (yield 78.5%, purity 96.6%).

Reference： [1]Patent: CN108341798,2018,A .Location in patent: Paragraph 0067

78
[ 112-37-8 ]
[ 83766-88-5 ]
[ 95935-43-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With boron trifluoride diethyl etherate; In toluene; at 20℃; for 0.5h;	Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

Reference： [1]Tetrahedron,2018,vol. 74,p. 3748 - 3754

79
[ 112-37-8 ]
α-D-glucosamine-(1''-11')-tunicamyl uracil dihydrochloride [ No CAS ]
di-N-undecanoyl-tunicamycin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		<strong>[112-37-8]Undecanoic acid</strong> (5 mg, 0.027 mmol, 2.5 equiv) and DIC (4.2 muIota_, 0.027 mmol, 2.5 equiv) were added to DMF (0.25 mL) with the addition of TEA (2 uL) and DMAP (2.7 mg, 0.022 mmol, 2 equiv.) and stirred at room temperature for one hour. Then, a-D- glucosamine-(l"-l l')-tunicamyl uracil dihydrochloride Compound D (7 mg, 0.011 mmol) was dissolved in DMF (0.25 mL) with the addition of TEA (4.1 muEpsilon), and added to the undecanoic acid reaction mixture. TEA was added to final of 4 equivalents. The reaction mixture was stirred at room temperature and reaction progress was checked by TLC (1/3/6, H20//PrOH/EtOAc) and HPLC. The reaction was stopped after 68 hours. The product was purified by HPLC, eluted at 18 min. The lyophilised product was washed with DCM and MilliQ water and resulted in 3 mg of the final product, 30% yield. Rf = 0.4 (1/3/6, H20//PrOH/EtOAc); [a]D20 = +30.9 ±0.4 (c 0.25, MeOH); Mp N/A; NMR (500 MHz, MeOD) delta ppm 7.91 (d, J= 8.1 Hz, 1H, H-6), 5.92 (d, J= 6.0 Hz, 1H, H-l '), 5.75 (d, J= 8.1 Hz, 1H, H-5), 4.93 (d, J= 3.4 Hz, 1H, Eta-Gamma), 4.60 (d, J = 8.5 Hz, 1H, H-l l '), 4.23 - 4.15 (m, 2H, H-2', H-3'), 4.05 - 3.98 (m, 2H, H-5', H-5"), 3.95 (m, 1H, H-10'), 3.90 (dd, J= 10.6, 3.4 Hz, 1H, H-2"), 3.86 - 3.80 (m, 2H, H-4', H- 6"), 3.76 (appt br dd, J= 10.7, 1.8 Hz, 1H, H-7'), 3.71 - 3.61 (m, 4H, H-8', H-9', H-3", H-6"), 3.34 (m, 1H, H-4"), 2.37 - 2.14 (m, 4H, 2xCH2fatty acyl), 2.13 - 2.05 (m, 1H, H- 6'), 1.68 - 1.56 (m, 4H, 2xCH2fatty acyl), 1.57 - 1.49 (m, 1H, H-6'), 1.30 (appt br s, 32H, CH2fatty acyl), 0.90 (t, J= 6.9 Hz, 6H, C%fatty acyl); 13C NMR (126 MHz, MeOD) delta ppm 177.17, 176.57, (2C, -N-C=Ofatty acyl), 166.22 (C-4), 152.67 (C-2), 142.76 (C-6), 103.06 (C-5), 101.34 (C-l l '), 100.02 (C-1"), 89.78 (C-1 '), 89.62 (C-4'), 75.53(C-2'), 74.37(C- 5"), 73.07, 73.05(2C, C-8', C-9'), 72.59 (C-4"), 72.49 (C-7'), 72.10 (C-3"), 70.90 (C- 3'), 68.33 (C-5'), 63.27(C-6"), 54.76(C- 2"), 54.46(C-10'), 37.82, 37.20(2C, -CO H2- fatty acyi^ 35 94(C-6'), 33.13, 30.82, 30.79, 30.77, 30.68, 30.64, 30.63, 30.54, 27.05, 26.83, 23.79 Q IC, - H2-fatty acyl), 14.48 (2C, - H3fatty acyl); IR (neat) v: 3297 (O-H), 2956 (C-H), 2921(C-H), 2852 (C-H), 1738 (C=0), 1719 (C=0), 1680 (C=C), 1645 (C=0), 1550 (N-H), 1468 (CH2), 1366 (CH3), 1229 (C-O-C), 1217 (C-OH), 1260 (C- O), 1092 (C-N), 1017 (=C-H); LRMS m/z (ESI"): 947 [(M+FA-H)", 100%]; HRMS m/z (ESI+): calc. C43H73N4Oi6 (M-H)" = 901.5027, found 901.5015. (H-4" signal in the NMR spectrum observed to be partially overlapped by the MeOD solvent peak. Not all aliphatic signals in carbon spectrum were resolved. Characterisation was assisted by COSY and HSQC.)

Reference： [1]Patent: WO2018/224822,2018,A1 .Location in patent: Page/Page column 41-42

80
[ 112-41-4 ]
[ 2855-19-8 ]
[ 1119-87-5 ]
[ 112-44-7 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphoric acid; cetylpyridinium chloride; dihydrogen peroxide; ortho-tungstic acid In water at 70℃;
	With N-hexadecylpyridinium chloride monohydrate; phosphoric acid; dihydrogen peroxide; ortho-tungstic acid at 70℃;

Reference： [1]Pyszny, Dariusz; Piotrowski, Tomasz; Orlińska, Beata [Organic Process Research and Development, 2019]
[2]Pyszny, Dariusz; Piotrowski, Tomasz; Orlińska, Beata [Organic Process Research and Development, 2019, vol. 23, # 3, p. 309 - 319]

81
[ 71310-21-9 ]
[ 112-37-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With di-tert-butyl peroxide; triethyl phosphite; In diethyl ether;	Use 0.75 mmol of substrate according to the general procedure.DTBP (1.2 equiv.),P(OEt)3 (2.0 equiv.),Reaction solvent diethyl ether (6 ml).After the reaction,Evaporate the solvent under reduced pressure.Crude product through chromatography column (petroleum ether / ethyl acetate = 1:5)Separating the crude product,The yield of nuclear magnetic analysis was 94%.

Reference： [1]Patent: CN110128252,2019,A .Location in patent: Paragraph 0026

82
[ 112-37-8 ]
[ 3669-80-5 ]
[ 35005-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,3,4,5,6-pentahydroxy-hexanal; cytochrome b5; glucose dehydrogenase from Bacillus megaterium; human cytochrome P₄₅₀ monooxygenase; rat cytochrome P₄₅₀ reductase; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; NADPH; superoxide dismutase; catalase from bovine liver In aq. phosphate buffer; dimethyl sulfoxide at 30℃; Enzymatic reaction;	2.4 Fatty acid and fatty alcohol conversion by CYP4B1 General procedure: Conversions of fatty acids 1-8 and fatty alcohols 9-12 were carried out in 50mM potassium phosphate buffer, pH 7.5 and a total reaction volume of 100μL. Reaction mixtures contained 0.25μM CYP4B1, 0.5μM CPR, 0.25μM cytochrome b5, 100 U mL-1 superoxide dismutase, 1000 UmL-1 catalase, 25 U mL-1 GDH, 20mM glucose, 25μgmL-1 DLPC, 200μM substrate (from a 10mM stock solution dissolved in DMSO) and 200μM NADPH. Samples were incubated at 30°C for 90min; this reaction time was chosen as an almost complete substrate conversion (as achieved for C12 4 after 120min) was not desirable, so as to allow comparison of the conversion values for the individual substrates and also between the two CYP4B1 isoforms.

Reference： [1]Thesseling, Florian A.; Hutter, Michael C.; Wiek, Constanze; Kowalski, John P.; Rettie, Allan E.; Girhard, Marco [Archives of Biochemistry and Biophysics, 2020, vol. 679]

83
[ 112-37-8 ]
[ 3669-80-5 ]
[ 35005-53-9 ]
[ 19790-86-4 ]
4-hydroxyundecanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,3,4,5,6-pentahydroxy-hexanal; cytochrome b5; glucose dehydrogenase from Bacillus megaterium; rabbit cytochrome P₄₅₀ monooxygenase; rat cytochrome P₄₅₀ reductase; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; NADPH; superoxide dismutase; catalase from bovine liver In aq. phosphate buffer; dimethyl sulfoxide at 30℃; Enzymatic reaction;	2.4 Fatty acid and fatty alcohol conversion by CYP4B1 General procedure: Conversions of fatty acids 1-8 and fatty alcohols 9-12 were carried out in 50mM potassium phosphate buffer, pH 7.5 and a total reaction volume of 100μL. Reaction mixtures contained 0.25μM CYP4B1, 0.5μM CPR, 0.25μM cytochrome b5, 100 U mL-1 superoxide dismutase, 1000 UmL-1 catalase, 25 U mL-1 GDH, 20mM glucose, 25μgmL-1 DLPC, 200μM substrate (from a 10mM stock solution dissolved in DMSO) and 200μM NADPH. Samples were incubated at 30°C for 90min; this reaction time was chosen as an almost complete substrate conversion (as achieved for C12 4 after 120min) was not desirable, so as to allow comparison of the conversion values for the individual substrates and also between the two CYP4B1 isoforms.

Reference： [1]Thesseling, Florian A.; Hutter, Michael C.; Wiek, Constanze; Kowalski, John P.; Rettie, Allan E.; Girhard, Marco [Archives of Biochemistry and Biophysics, 2020, vol. 679]

84
[ 112-37-8 ]
[ 71989-26-9 ]
[ 204777-78-6 ]
C₅₅H₉₅N₇O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Rink amide AM resin (loading 0.94 mmol/g, 300 mg) was treated with 20% piperidine in DMF (6.0 ml) andshaken at room temperature for 30 minutes to remove the Fmoc protecting group. The resin was drained and washedwith DMF (x3), MeOH (x3), and DCM (x3).Loading of Rink Amide AM Resin with Fmoc-L-Lys(Boc)-OH:Fmoc-L-Lys(Boc)-OH (703 mg) was dissolved in DMF (3.0 ml, 0.5 M). A solution of HBTU in DMF (3.0 ml, 0.5M) was added followed by DIPEA (523 ml). The solution was stood at room temperature for 10 minutes then added tothe resin which had been washed previously three times with DMF. The resin was then shaken at room temperature for1 hour, drained and washed with DMF (x3), MeOH (x3) and DCM (x3).Fmoc Deprotection:The resin was treated with 20% piperidine in DMF (6.0 ml) and shaken at room temperature for 30 minutes.The resin was drained and washed with DMF (x3), MeOH (x3), and DCM (x3).Peptide Coupling with Fmoc-L-Lys(ivDde)-OH:[0178] A solution of Fmoc-L-Lys(ivDde)-OH (423 mg) in DMF (4..5ml, 0.167 M) was prepared. To this, a solution ofHBTU in DMF (1.5 ml, 0.5 M) was added followed by DIPEA (261 ml). The solution was stood at room temperature for10 minutes then added to the resin which had been washed previously three times with DMF. The resin was then shakenat room temperature for 2 hours, drained and washed with DMF (x3), MeOH (x3) and DCM (x3). This step was repeated.The Fmoc deprotection and coupling with Fmoc-L-Lys(ivDde)-OH steps were repeated, followed by anotherFmoc deprotection.Coupling with Undecanoic Acid:[0180] A solution of undecanoic acid (279 mg) in DMF (3.0 ml) was mixed with a solution of HBTU in DMF (3.0 ml,0.5 M) and DIPEA (523 ml). The solution was stood at room temperature for 10 minutes then added to the resin previouslywashed three times with DMF. The resin was shaken at room temperature for 1 hour, drained and washed with DMF(x3), MeOH (x3) and DCM (x3). The resin was dried in vacuo. 5 mg of resin was cleaved to check the extent of thereaction. The resin was dissolved in 1.0 ml acetonitrile, filtered through a 0.45mm syringe filter and analysed by LCMS.LCMS analysis: RT 9.088 min, 80% by ELSD, (M+H)+ 982.5, (M+2+)2+ 491.9, (M+3H)3+ 328.3.Cleavage of Rink Amide AM Resin and Boc Deprotection; A solution of 20% TFA, 5% triethylsilane in DCM (6.0 ml) was prepared and added to the resin (300 mg) for30 minutes. The resin was removed by filtration and washed with DCM (x3) and acetonitrile (x3). The solvent wasremoved in vacuo. The resin was dissolved in 1:1 ACN/H2O and freeze-dried.

Reference： [1]Patent: EP3105244,2020,B1 .Location in patent: Paragraph 0174-0181

85
[ 4286-55-9 ]
[ 112-37-8 ]
6-bromohexyl undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 5h;Inert atmosphere;	A mixture of undecanoic acid (5 g, 1.0 equiv), 6-bromohexan-l-ol (1.0 equiv), EDCI (1.0 equiv), DMAP (0.16 equiv) and DIPEA (3.0 equiv) in DCM (0.2 M) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 20 C for 5 h under inert atmosphere. ETpon completion, the reaction mixture was concentrated under reduced pressure to remove DCM. The residue was diluted with H2O and extracted 3x with EtOAc. The combined organic layers were dried over Na2S04, filtered, and concentrated. Purification by column (EtOAc/hexanes) afforded product as a colorless oil (2.3 g, 25%). NMR (400 MHz, CDCh) d 4.00 (t, J = 6.6 Hz, 2H), 3.34 (t, J = 6.8 Hz, 2H), 2.22 (t, J = 7.6 Hz, 2H), 1.84 - 1.74 (m, 2H), 1.63 - 1.50 (m, 4H), 1.45 - 1.36 (m, 2H), 1.36 - 1.28 (m, 2H), 1.20 (d, J = 9.9 Hz, 15H), 0.86 - 0.78 (m, 3H).

Reference： [1]Patent: WO2020/72605,2020,A1 .Location in patent: Page/Page column 85

86
[ 112-37-8 ]
[ 2009-97-4 ]
[ 98-88-4 ]
ethyl 8-benzamido-2-(2-(dodecanoyloxy)ethyl)-3-methyl-1-oxo-1,2-dihydroisoquinoline-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) triflimide; In tetrahydrofuran; at 80℃; for 12h;Inert atmosphere;	General procedure: A sealed reaction tube was charged with phenyloxazole (0.20 mmol), diazo compounds (0.40mmol), [RhCp*Cl2]2 (2.5 mol%), AgNTf2 (10 mol%), acid(2 equiv) in 1,4-dioxane (or THF) 2.0 mL. The mixture was stirred at 60 C (or 80C ) for 20 h (or 12 h) under N2 atmosphere. After that, the solvent was removed under vacuum and the residue was purified by silicagel chromatography using ethylacetate/petroleum ether to afford product 3 and 4.

Reference： [1]Chinese Chemical Letters,2020

87
[ 112-37-8 ]
[ 7307-55-3 ]
[ 2244-06-6 ]
[ 16165-33-6 ]
[ 544689-62-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 70% 2: 7% 3: 13% 4: 6%	Stage #1: undecylenic acid With cyclopentyl methyl ether; ammonia at 200℃; Sealed tube; Green chemistry; Stage #2: With cyclopentyl methyl ether; ammonia; hydrogen at 200℃; for 6.5h; Cooling with ice; Green chemistry;

Reference： [1]Coeck, Robin; De Vos, Dirk E. [Green Chemistry, 2020, vol. 22, # 15, p. 5105 - 5114]

88
5-fluoro-1-methyl-2-undecyl-1H-benzo[d]imidazole [ No CAS ]
[ 112-37-8 ]
[ 1365271-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1,1,3,3,3-hexamethyldisilazane potassium In tetrahydrofuran; toluene at 50℃;	2.2. C-C cleavage of alkyl benzimidazoles General procedure: Protocol A: To a 10 mL round-bottom flask charged with benzimidazole 1 (0.2 mmol)in toluene (1 mL) was added KHMDS (1 M solution in THF, 5 equiv.), the mixture washeated to 50 oC and then reacted for 4-6 hours. After the completion of reaction, water(5 mL) was added to quench the reaction. Extracting the mixture with DCM (10 mL ×3). The combined organic phase was dried with anhydrous Na2SO4 and the solvent wasremoved under vacuum to get the crude products benzimidazoles 2. The aqueous phasewas further acidified to pH 3, extracted again with DCM (10 mL × 3). The combinedorganic phase was dried with anhydrous Na2SO4 and the solvent was removed undervacuum to get the crude products carboxylic acids 3. The purification was performed by flash column chromatography on silica gel to get the products 2 and 3 respectively.

Reference： [1]Fu, Xuegang; Guo, Dongyang; Yan, Yuting; Marselo, Timotius; Zhang, Mingyu; Zhang, Zhenghan; Li, Siying; Huang, Jianhui [Synthesis, 2022]

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P320
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P353	Rinse skin with water/shower.
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P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
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Physical hazards
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H271	May cause fire or explosion; strong oxidizer
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Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
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H317	May cause an allergic skin reaction
H318	Causes serious eye damage
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H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 112-37-8 ] {[proInfo.proName]}

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[ 112-37-8 ] Synthesis Path-Upstream 1~2

[ 112-37-8 ] Synthesis Path-Downstream 1~88

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