[ CAS No. 6169-06-8 ] {[proInfo.proName]}

Name: 6169-06-8|(S)-Octan-2-ol|98%
Brand: Ambeed
SKU: A859468
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Quality Control of [ 6169-06-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6169-06-8 ]

Product Details of [ 6169-06-8 ]

CAS No. :	6169-06-8	MDL No. :	MFCD00064283
Formula :	C₈H₁₈O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	130.23	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 6169-06-8 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	5
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.73
TPSA :	20.23 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) :	-5.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.62
Log Po/w (XLOGP3) :	2.9
Log Po/w (WLOGP) :	2.34
Log Po/w (MLOGP) :	2.22
Log Po/w (SILICOS-IT) :	1.97
Consensus Log Po/w :	2.41

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.14
Solubility :	0.934 mg/ml ; 0.00717 mol/l
Class :	Soluble
Log S (Ali) :	-2.99
Solubility :	0.135 mg/ml ; 0.00103 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.12
Solubility :	0.999 mg/ml ; 0.00767 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 6169-06-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6169-06-8 ]

* 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 [ 6169-06-8 ]

[ 6169-06-8 ] Synthesis Path-Downstream 1~40

1
[ 4128-31-8 ]
[ 6169-06-8 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 13969 - 13972
[2]Journal of the American Chemical Society,1984,vol. 106,p. 2687 - 2692
[3]Organic Syntheses 6, 68 <New York 1926>,
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[5]Angewandte Chemie - International Edition,2002,vol. 41,p. 4052 - 4054
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[8]Organic Letters,2011,vol. 13,p. 4296 - 4299
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[10]ChemCatChem,2015,vol. 7,p. 4016 - 4020
[11]ChemBioChem,2016,p. 1349 - 1358
[12]Green Chemistry,2020,vol. 22,p. 2767 - 2777

2
[ 6169-06-8 ]
[ 1202-25-1 ]
4-dimethylamino-benzoic acid-(1-methyl-heptyl ester) [ No CAS ]

Reference： [1]Journal of the Chemical Society,1929,p. 2275,2280

3
[ 6169-06-8 ]
[ 98-59-9 ]
[ 34817-25-9 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 9533 - 9536
Angew. Chem.,2019,vol. 131,p. 9633 - 9636,4
[2]Organic Letters,2019,vol. 21,p. 9268 - 9271
[3]Chemistry - A European Journal,2009,vol. 15,p. 2071 - 2080
[4]Journal of the Chemical Society. Perkin transactions I,1996,p. 2567 - 2573
[5]Journal of Organic Chemistry,2009,vol. 74,p. 6042 - 6049
[6]Journal of Organic Chemistry,1991,vol. 56,p. 1623 - 1630
[7]Journal of Organic Chemistry,1962,vol. 27,p. 290 - 292
[8]Journal of Materials Chemistry C,2013,vol. 1,p. 7346 - 7356
[9]Journal of the American Chemical Society,2020

4
[ 6169-06-8 ]
[ 65-85-0 ]
[ 6938-51-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 20℃;Product distribution / selectivity;	After (S)-2-octanol (300 mg, 2.30 mmol), triphenylphosphine (728 mg, 2.76 mmol), benzoic acid (338 mg, 2.76 mmol), and THF (12 ml) were added to a 50 ml flask, a 40% azodicarboxylic acid diisopropyl ester-toluene solution (1.45 ml, 2.76 mmol) dissolved in THF (6 ml) was added dropwise thereto at 20C, and the reaction was allowed to proceed for two hours. Water (0.5 mL) was added, and concentration was carried out. Then, water (10 ml) was added to the solution, and extraction was carried out using diethyl ether (10 ml, * 2). Then, the organic layer was washed with water (10 ml) and saturated salt water (10 ml), and dehumidified with anhydrous magnesium sulfate. Subsequently, a crude product obtained by concentration was purified by column chromatography (silica gel, 10% ethyl acetate-hexane solution) to give (R)-2-benzoyloxyoctane as a colorless liquid substance (503 mg, yield: 93%/(S)-2-octanol). 1H NMR (600 MHz, CDCl3): delta 7.97 (d, J = 7.6 Hz, 2H), 7.47 (t, J = 7.6 Hz, 1H), 7.36 (t, J = 7.6 Hz, 2H), 5.08 (m, 1H), 1.66 (m, 1H), 1.53 (m, 1H), 1.35-1.18 (m, 11H), 0.80 (t, J = 6.9 Hz, 3H).

Reference： [1]Patent: EP2112136,2009,A1 .Location in patent: Page/Page column 15
[2]Tetrahedron Letters,1993,vol. 34,p. 1639 - 1642
[3]Tetrahedron,2009,vol. 65,p. 6109 - 6114
[4]Journal of Organic Chemistry,2001,vol. 66,p. 2178 - 2180
[5]Chemistry Letters,2007,vol. 36,p. 566 - 567
[6]Chemical Communications,2014,vol. 50,p. 7340 - 7343
[7]Tetrahedron Letters,2002,vol. 43,p. 2807 - 2810
[8]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 3427 - 3430

5
[ 1122-28-7 ]
[ 6169-06-8 ]
(R)-(-)-1-(2-Octyl)imidazole-4,5-dicarbonitrile [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1994,vol. 5,p. 181 - 184
[2]Journal of Organic Chemistry,1995,vol. 60,p. 2008 - 2015

6
[ 6169-06-8 ]
[ 5978-70-1 ]

Reference： [1]Synthesis,2013,vol. 45,p. 931 - 935
[2]Journal of Organic Chemistry,1981,vol. 46,p. 4321 - 4323
[3]Angewandte Chemie,1987,vol. 99,p. 800 - 802
[4]Angewandte Chemie,1987,vol. 99,p. 800 - 802
[5]Synthesis,1991,p. 465 - 469
[6]Chemistry - A European Journal,2008,vol. 14,p. 11480 - 11487
[7]Journal of Organic Chemistry,2010,vol. 75,p. 5740 - 5742

7
[ 27770-99-6 ]
[ 6169-06-8 ]
[ 5978-70-1 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 1360 - 1362

8
[ 6169-06-8 ]
[ 124-63-0 ]
[ 62820-85-3 ]

Reference： [1]Synthetic Communications,1983,vol. 13,p. 553 - 558
[2]Synthesis,2006,p. 2760 - 2766
[3]Phosphorus, Sulfur and Silicon and the Related Elements,1993,vol. 75,p. 51 - 54
[4]Journal of Organometallic Chemistry,1980,vol. 191,p. C1 - C2
[5]Journal of the American Chemical Society,2020

9
[ 111-13-7 ]
[ 6169-06-8 ]
[ 5978-70-1 ]

Reference： [1]Journal of the American Chemical Society,1986,vol. 108,p. 7402 - 7404
[2]Chemistry Letters,1982,p. 315 - 316
[3]Chemistry Letters,1985,p. 1609 - 1612
[4]Journal of the American Chemical Society,1986,vol. 108,p. 7404 - 7405
[5]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 1277 - 1280
[6]Journal of Organic Chemistry,1982,vol. 47,p. 2495 - 2496
[7]Journal of Organic Chemistry,1989,vol. 54,p. 159 - 165
[8]Chemistry Letters,1985,p. 1609 - 1612
[9]Journal of the American Chemical Society,1986,vol. 108,p. 7404 - 7405
[10]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 25 - 29
[11]Journal of the Chemical Society. Chemical communications,1992,p. 494 - 496
[12]Tetrahedron Asymmetry,1994,vol. 5,p. 165 - 168
[13]Tetrahedron Letters,1996,vol. 37,p. 3791 - 3794
[14]Chemistry Letters,1984,p. 2071 - 2074
[15]Tetrahedron Asymmetry,1995,vol. 6,p. 301 - 306
[16]Tetrahedron Letters,1999,vol. 40,p. 1327 - 1330
[17]Tetrahedron Asymmetry,1999,vol. 10,p. 3515 - 3520
[18]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 485 - 496
[19]Synthetic Communications,2000,vol. 30,p. 4329 - 4341
[20]Chemistry Letters,2000,p. 990 - 991
[21]Tetrahedron Asymmetry,2000,vol. 11,p. 3553 - 3560
[22]Tetrahedron Asymmetry,2000,vol. 11,p. 4329 - 4340
[23]Chemistry - A European Journal,2001,vol. 7,p. 2158 - 2166
[24]Angewandte Chemie - International Edition,2002,vol. 41,p. 3892 - 3894
[25]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 2695 - 2696
[26]Angewandte Chemie - International Edition,2004,vol. 43,p. 1014 - 1017
[27]Tetrahedron Asymmetry,2004,vol. 15,p. 2263 - 2271
[28]Tetrahedron Asymmetry,2005,vol. 16,p. 751 - 754
[29]Angewandte Chemie - International Edition,2004,vol. 43,p. 6731 - 6734
[30]European Journal of Organic Chemistry,2005,p. 5289 - 5295
[31]Journal of the American Chemical Society,2006,vol. 128,p. 1044 - 1045
[32]Tetrahedron Letters,2006,vol. 47,p. 3901 - 3903
[33]Chemistry - A European Journal,2001,vol. 7,p. 2158 - 2166
[34]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 3205 - 3211
[35]Tetrahedron Letters,2007,vol. 48,p. 9025 - 9029
[36]Tetrahedron Asymmetry,2008,vol. 19,p. 1954 - 1958
[37]Bulletin of the Chemical Society of Japan,2008,vol. 81,p. 274 - 277
[38]Organic Letters,2008,vol. 10,p. 2155 - 2158
[39]Advanced Synthesis and Catalysis,2008,vol. 350,p. 995 - 1000
[40]Synthesis,2008,p. 3874 - 3876
[41]Tetrahedron,2010,vol. 66,p. 6062 - 6069
[42]Journal of Molecular Catalysis B: Enzymatic,2010,vol. 65,p. 37 - 40
[43]Tetrahedron Letters,2011,vol. 52,p. 1485 - 1489
[44]Chemistry Letters,2009,vol. 38,p. 722 - 723
[45]Organic Letters,2012,vol. 14,p. 5134 - 5137,4
[46]Journal of Molecular Catalysis B: Enzymatic,2014,vol. 105,p. 66 - 73
[47]Journal of the American Chemical Society,2015,vol. 137,p. 2456 - 2459
[48]Angewandte Chemie - International Edition,2015,vol. 54,p. 9333 - 9337
Angew. Chem.,2015,vol. 127,p. 9465 - 9469,5
[49]Tetrahedron Asymmetry,2015,vol. 26,p. 1453 - 1458
[50]Advanced Synthesis and Catalysis,2016,vol. 358,p. 515 - 519
[51]European Journal of Organic Chemistry,2014,vol. 2014,p. 5532 - 5539
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[53]ChemCatChem,2017,vol. 9,p. 3125 - 3130
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[56]Molecular catalysis,2018,vol. 445,p. 187 - 194
[57]Bulletin of the Chemical Society of Japan,2018,vol. 91,p. 1325 - 1332
[58]Organic Process Research and Development,2019,vol. 23,p. 1841 - 1851
[59]Organometallics,2020,vol. 39,p. 247 - 257
[60]Organic process research and development,2020,vol. 24,p. 1068 - 1076

10
[ 6169-06-8 ]
[ 245743-64-0 ]
[ 211172-74-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 25℃; for 2h;

Reference： [1]Dinescu, Liviu; Maly, Kenneth E.; Lemieux, Robert P. [Journal of Materials Chemistry, 1999, vol. 9, # 8, p. 1679 - 1686]

11
[ 6169-06-8 ]
[ 114045-96-4 ]
[ 239803-48-6 ]

Reference： [1]Journal of Materials Chemistry,2001,vol. 11,p. 1590 - 1599

12
[ 6169-06-8 ]
[ 85232-02-6 ]
[ 104-15-4 ]
Toluene-4-sulfonic acid; compound with (R)-1-methyl-heptylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: (S)-2-Octanol; diethyl N-tert-butyloxycarbonylphosphoramidate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20 - 25℃; for 2h; Stage #2: toluene-4-sulfonic acid In ethanol for 12h; Heating;

Reference： [1]Klepacz; Zwierzak [Synthetic Communications, 2001, vol. 31, # 11, p. 1683 - 1689]

13
[ 6169-06-8 ]
[ 108-24-7 ]
[ 3540-05-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1846 - 1849
[2]Bioscience, Biotechnology and Biochemistry,2003,vol. 67,p. 203 - 206
[3]Bioscience, Biotechnology and Biochemistry,2002,vol. 66,p. 221 - 223
[4]Organic Letters,2011,vol. 13,p. 4296 - 4299
[5]Green Chemistry,2019,vol. 21,p. 2946 - 2951

14
[ 6169-06-8 ]
[ 114045-96-4 ]
4-Benzyloxy-2-fluoro-benzoic acid (S)-1-methyl-heptyl ester [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2002,vol. 381,p. 21 - 32

15
[ 6169-06-8 ]
[ 666829-99-8 ]
[ 666830-01-9 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 1161 - 1167

16
[ 136918-14-4 ]
[ 6169-06-8 ]
[ 61046-60-4 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5069 - 5072
[2]Synthesis,2009,p. 332 - 334
[3]Organic Letters,2006,vol. 8,p. 71 - 74

17
[ 100-02-7 ]
[ 6169-06-8 ]
[ 850903-50-3 ]

Reference： [1]New Journal of Chemistry,2015,vol. 39,p. 2011 - 2027
[2]Journal of Physical Chemistry B,2015,vol. 119,p. 4539 - 4551
[3]Macromolecules,2005,vol. 38,p. 2729 - 2738
[4]Journal of Materials Chemistry,2009,vol. 19,p. 4922 - 4930

18
[ 6169-06-8 ]
[ 62-23-7 ]
(1R)-1-methylheptyl 4-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine; In toluene; at 20℃;Product distribution / selectivity;	After (S)-2-octanol (300 mg, 2.30 mmol), triphenylphosphine (725 mg, 2.76 mmol), 4-nitrobenzoic acid (463 mg, 2.76 mmol), and toluene (12 ml) were added to a 50 ml flask, azodicarboxylic acid bis(2-methoxyethyl) ester (648 mg, 2.76 mmol) dissolved in toluene (6 ml) was added dropwise thereto at 20C, and the reaction was allowed to proceed for 3.5 hours. Water (10 mL) was added, and separation was carried out. Then, the aqueous layer was extracted using toluene (10 mL, * 1). The resulting organic layer was collectively washed with water (10 mL) and saturated salt water (10 ml), and dehumidified with anhydrous magnesium sulfate. Subsequently, a crude product obtained by concentration was purified by column chromatography (silica gel, 5% ethyl acetate-hexane solution) to give (R)-2-(4-nitrobenzoyloxy)octane as a pale yellow liquid substance (615 mg, yield: 96%/(S)-2-octanol). 1H NMR (600 MHz, CDCl3): delta 8.26 (d, J = 8.6 Hz, 2H), 8.18 (d, J = 8.6 Hz, 2H), 5.17 (m, 1H), 1.38-1.26 (m, 11H), 0.85 (t, J = 6.5 Hz, 3H).

Reference： [1]Patent: EP2112136,2009,A1 .Location in patent: Page/Page column 20-21
[2]Tetrahedron,2009,vol. 65,p. 6109 - 6114
[3]Journal of Organic Chemistry,2018,vol. 83,p. 4712 - 4729
[4]Angewandte Chemie - International Edition,2006,vol. 45,p. 1415 - 1420
[5]Chemical Science,2016,vol. 7,p. 5148 - 5159
[6]Chemical Communications,2014,vol. 50,p. 7340 - 7343

19
[ 6169-06-8 ]
[ 14180-11-1 ]
[ 271786-19-7 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 881 - 883

20
[ 5978-70-1 ]
[ 6169-06-8 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 6647 - 6658
[2]Tetrahedron Asymmetry,2002,vol. 13,p. 1435 - 1441
[3]Angewandte Chemie - International Edition,2008,vol. 47,p. 741 - 745
[4]Chemistry - A European Journal,2008,vol. 14,p. 11480 - 11487
[5]Organic Letters,2011,vol. 13,p. 4296 - 4299

21
[ 33758-34-8 ]
[ 6169-06-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 2: 1.) sec-BuLi, (-)-Spartein / 1.) Cyclohexan, Isopentan, Ether, -78 deg C, 2.) -78 deg C, 16h 3: 1.) Methansulfonsaeure, 2.) Ba(OH)2*8H₂O / 1.) MeOH, reflux, 16h, 2.) reflux, 4h

Reference： [1]Hoppe, Dieter; Hintze, Folker; Tebben, Petra [Angewandte Chemie, 1990, vol. 102, # 12, p. 1457 - 1459]

22
[ 6169-06-8 ]
[ 3004-93-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine; SOCl₂ / -10 °C 2: diethyl ether; lithium / 0 °C 3: diethyl ether

Reference： [1]Tarbell; Weiss [Journal of the American Chemical Society, 1939, vol. 61, p. 1204]

23
[ 6169-06-8 ]
[ 2446-83-5 ]
[ 603-35-0 ]
[ 245743-64-0 ]
[ 211172-74-6 ]

Yield	Reaction Conditions	Operation in experiment
158 mg (95%)	In dichloromethane	3 Methyl (R)-5-chloro-2-fluoro-4-(2-octyloxy)benzoate (S9) Methyl (R)-5-chloro-2-fluoro-4-(2-octyloxy)benzoate (S9) Under a N2 atmosphere, diisopropylazodicarboxylate (DIAD, 146 mg, 0.72 mmol) was added dropwise to a stirred solution of S8 (98 mg, 0.47 mmol), triphenyl phosphine (189 mg, 0.72 mmol) and (S)-2-octanol (95 mg, 0.72 mmol) in dry CH2 Cl2 (10 ml). After stirring at 25° C. for 2 h, the solvent was removed in vacuo, and the oily residue was purified by flash chromatography on silica gel (30% ethyl acetate/toluene) to give 158 mg (95%) of S9 as an oil.

Reference： [1]Current Patent Assignee: QUEEN'S UNIVERSITY AT KINGSTON - US5989451, 1999, A

24
petroleum [ No CAS ]
[ 6169-06-8 ]
[ 1486-51-7 ]
petrol [ No CAS ]
[ 111153-20-9 ]

Yield	Reaction Conditions	Operation in experiment
85.3%	With thionyl chloride; In pyridine; dichloromethane; toluene;	Step B(i) S(+)-1-Methylheptyl 4-benzyloxybenzoate 4-Benzyloxybenzoic acid (55 g) was converted to the acid chloride with thionyl chloride (120 ml) as described in example 1, and then reacted with S(+)-2-octanol (31.4 g) in pyridine (150 ml) and toluene (250 ml). The crude, yellow liquid product (80.7 g) was adsorbed on a mixture of alumina (240 g) and silica gel (240 g) from petroleum spirit (60-80) and eluted with a 1:1 mixture of petrol and dichloromethane. The product was obtained as a colourless oil (70.0 g, 85.3% yield).

Reference： [1]Patent: US5061399,1991,A

25
petroleum [ No CAS ]
[ 6169-06-8 ]
[ 114804-77-2 ]
[ 114804-78-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine; thionyl chloride; In toluene;	Step C(iv) S(+)-1-Methylheptyl 6-benzyloxy-2-naphthoate 6-Benzyloxy-2-naphthoic acid (34.7 g) was converted to the acid chloride with thionyl chloride (150 ml) and the crude product (37.0 g) was reacted with S(+)-2-octanol (16.2 g) in toluene (120 ml) and pyridine (65 ml). The crude product was chromatographed over alumina (150 g) and silica gel (150 g) in a 2:1 - mixture of petroleum spirit (60-80) and dichloromethane and eluted with dichloromethane. The naphthoate was obtained as a white solid (38.0 g, 76% theory) mpt 71-73, 99.6% pure by glc.
76%	With pyridine; thionyl chloride; In toluene;	Step C(iv) s(+)-1-methylheptyl 6-benzyloxy-2-naphthoate 6-Benzyloxy-2-naphthoic acid (34.7 g) was converted to the acid chloride with thionyl chloride (150 ml) and the crude product (37.0 g) was reacted with s(+)-2-octanol (16.2 g) in toluene (120 ml) and pyridine (65 ml). The crude product was chromatographed over alumina (150 g) and silica gel (150 g) in a 2: 1 - mixture of petroleum spirit (60-80) and dichloromethane and eluted with dichloromethane. The naphthoate was obtained as a white solid (38.0 g, 76% theory) mpt 71-73, 99.6% pure by glc.

Reference： [1]Patent: US5061399,1991,A
[2]Patent: EP302875,1991,B1

26
[ 6169-06-8 ]
[ 121219-03-2 ]
[ 144808-74-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate;	(R)-(-)-1-Bromo-3-fluoro-4-(1-methylheptyloxy)benzene (35) Quantities: <strong>[121219-03-2]4-bromo-3-fluorophenol</strong> (34) (7.33 g, 0.038 mol), (S)-(+)-octan-2-ol (5.00 g, 0.038 mol), DEAD (6.69 g, 0.038 mol), triphenylphosphine (10.07 g, 0.038 mol). The experimental procedure was as described for the preparation of compound 5. The product was purified by column chromatography (70% petrol/dichloromethane) to give a colourless oil. Yield: 10.62 g (92%).

Reference： [1]Patent: US6242636,2001,B1

27
[ 4128-31-8 ]
[ 42981-08-8 ]
[ 6169-06-8 ]
[ 256474-24-5 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 1730 - 1732

28
[ 4128-31-8 ]
[ 532-27-4 ]
[ 6169-06-8 ]
[ 5978-70-1 ]
[ 56751-12-3 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 1730 - 1732

29
[ 6169-06-8 ]
[ 3696-28-4 ]
[ 1200233-02-8 ]

Yield	Reaction Conditions	Operation in experiment
49%	With tributylphosphine In dichloromethane at 20℃; Inert atmosphere; enantioselective reaction;

Reference： [1]Location in patent: experimental part Hartung, Jens; Kempter, Irina; Gottwald, Thomas; Schwarz, Michaela; Kneuer, Rainer [Tetrahedron Asymmetry, 2009, vol. 20, # 18, p. 2097 - 2104]

30
[ 6169-06-8 ]
[ 69026-14-8 ]
[ 1225651-21-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

Reference： [1]Fergusson, Kenneth M.; Hird, Michael [Journal of Materials Chemistry, 2010, vol. 20, # 15, p. 3069 - 3078]

31
[ 4128-31-8 ]
[ 124-07-2 ]
[ 6169-06-8 ]
[ 117707-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	With Novozyme 435; In neat (no solvent); at 45℃; under 760.051 Torr; for 12h;Molecular sieve; Green chemistry; Enzymatic reaction;	General procedure: Racemic 2-pentanol or 2-octanol (36 mmol), fatty acid (54 mmol), and 4 A molecular sieves (6.0 g) were added to a conical flask with a stopper. The reaction was started by the addition of Novozyme 435 (0.18 g). Samples (15 muL) were withdrawn at regular intervals, diluted with n-hexane (0.5 mL) and analyzed as described above.

Reference： [1]Tetrahedron Asymmetry,2013,vol. 24,p. 249 - 253

32
[ 4128-31-8 ]
[ 334-48-5 ]
[ 6169-06-8 ]
Decanoic acid (R)-1-methyl-heptyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Novozyme 435; In neat (no solvent); at 45℃; under 760.051 Torr; for 12h;Molecular sieve; Green chemistry; Enzymatic reaction;	General procedure: Racemic 2-pentanol or 2-octanol (36 mmol), fatty acid (54 mmol), and 4 A molecular sieves (6.0 g) were added to a conical flask with a stopper. The reaction was started by the addition of Novozyme 435 (0.18 g). Samples (15 muL) were withdrawn at regular intervals, diluted with n-hexane (0.5 mL) and analyzed as described above.

Reference： [1]Tetrahedron Asymmetry,2013,vol. 24,p. 249 - 253

33
[ 4128-31-8 ]
[ 120-45-6 ]
[ 6169-06-8 ]
[ 5978-70-1 ]
[ 1517-69-7 ]
[ 116907-37-0 ]
[ 107832-32-6 ]
[ 120-45-6 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 2917 - 2923

34
[ 4128-31-8 ]
[ 35279-24-4 ]
[ 6169-06-8 ]
[ 5978-70-1 ]
[ 219119-81-0 ]
[ 138309-06-5 ]
(S)-1-(4-Methoxyphenyl)ethanol [ No CAS ]
[ 1517-70-0 ]
[ 116907-37-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 99 % ee 2: 8 % ee 3: 11 % ee 4: 77 % ee	With lipase B from Candida antarctica In toluene at 78℃; for 48h; Enzymatic reaction;

Reference： [1]Xia, Bo; Cheng, Guilin; Lin, Xianfu; Wu, Qi [European Journal of Organic Chemistry, 2014, vol. 2014, # 14, p. 2917 - 2923]

35
[ 84782-03-6 ]
[ 3319-15-1 ]
[ 6169-06-8 ]
[ 5978-70-1 ]
[ 138309-06-5 ]
(S)-1-(4-Methoxyphenyl)ethanol [ No CAS ]
[ 1517-70-0 ]
[ 116907-37-0 ]
[ 149403-13-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 99 % ee 2: 3 % ee 3: 7 % ee 4: 87 % ee	With lipase B from Candida antarctica In toluene at 78℃; for 48h; Enzymatic reaction;

Reference： [1]Xia, Bo; Cheng, Guilin; Lin, Xianfu; Wu, Qi [European Journal of Organic Chemistry, 2014, vol. 2014, # 14, p. 2917 - 2923]

36
[ 6169-06-8 ]
[ 67696-25-7 ]
[ 65-85-0 ]
[ CAS Unavailable ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 86%	In ethyl acetate at 70 - 78℃; for 18h;

Reference： [1]Tang, Xiaoping; Chapman, Charlotte; Whiting, Matthew; Denton, Ross [Chemical Communications, 2014, vol. 50, # 55, p. 7340 - 7343]

37
[ 4128-31-8 ]
2F₆P^(1-)*C₃₀H₅₂N₄O₃⁽²⁺⁾ [ No CAS ]
[ 6169-06-8 ]
C₂₃H₄₃N₂O₂⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With Candida antarctica lipase B; In acetone; at 35℃; for 3h;Resolution of racemate; Enzymatic reaction;	General procedure: The amount of CALB beads necessary to perform each enzymatickinetic resolution (20 mg) was first embedded in n-hexane(1 mL) for 1 hour, then filtered and washed three times with acetone(3 0.5 mL). After filtration, the beads were used withoutdrying to carry out the enzymatic reaction.The enzymatic reactions began with the addition of a stirredsolution of acylating agent (0.41 mmol) and racemic sec-alcohol(0.41 mmol) in 0.8 mL of distilled acetone to 20 mg of CALB (Novozym435). Reactions were carried out in 4 mL glass screw-capvials placed in an incubator at 35 C and 170 rpm, for the timerequired to reach 50% of conversion. The optimal reaction timefor each enzymatic kinetic resolution was previously determinedby GC analysis of several aliquots (100 lL) withdrawn from theenzymatic reaction at different time intervals. Both the aliquotsand the complete reactions were treated as follows: (i) the enzymewas filtered off and acetone was evaporated under reduced pressure;(ii) the unreacted (S)-enriched-alcohol was extracted withEt2O, passed through a pipette sized column with silica, and driedunder reduced pressure; (iii) the remainder of the enzymatic resolution,containing the attached (R)-enantiomer and the ionic acid,was resuspended in 1 mL of a 4 M solution of KOH in methanoland stirred for 30 min at 50 C; (iv) the (R)-enriched-alcohol wasextracted with Et2O, passed through a pipette size column with silica,and dried under reduced pressure.

Reference： [1]Tetrahedron Asymmetry,2014,vol. 25,p. 944 - 948

38
[ 6169-06-8 ]
[ 50670-76-3 ]
ethyl 4-(4-(R)-2-methylheptanoxyphenyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: ethyl 4-hydroxy-4-biphenyl carboxylate With triphenylphosphine In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: (S)-2-Octanol With diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 17h;

Reference： [1]Kishikawa, Keiki; Sugiyama, Takaaki; Watanabe, Tomohiro; Aoyagi, Shota; Kohri, Michinari; Taniguchi, Tatsuo; Takahashi, Masahiro; Kohmoto, Shigeo [Journal of Physical Chemistry B, 2014, vol. 118, # 34, p. 10319 - 10332]

39
[ 55589-47-4 ]
[ 6169-06-8 ]
[ 54010-75-2 ]
[ 1539-42-0 ]
[ 75-05-8 ]
C₂₉H₃₉N₅OZn⁽²⁺⁾ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 8045 - 8047

40
[ 6169-06-8 ]
[ 24821-22-5 ]
(R)-oct-2-yl 2,6-bis(trifluoromethyl)benzoate [ No CAS ]

Reference： [1]Green Chemistry,2021,vol. 23,p. 8859 - 8864

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6169-06-8 ] {[proInfo.proName]}

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[ 6169-06-8 ] Synthesis Path-Downstream 1~40

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Aliphatic Chain Hydrocarbons

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[ 6169-06-8 ]