[ CAS No. 124-25-4 ] {[proInfo.proName]}

Name: 124-25-4|Tetradecanal|97%
Brand: Ambeed
SKU: A285058
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2D 3D

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Quality Control of [ 124-25-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 124-25-4 ]

SDS Specification

Alternatived Products of [ 124-25-4 ]

Product Details of [ 124-25-4 ]

CAS No. :	124-25-4	MDL No. :	MFCD00007019
Formula :	C₁₄H₂₈O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UHUFTBALEZWWIH-UHFFFAOYSA-N
M.W :	212.37	Pubchem ID :	31291
Synonyms :

Calculated chemistry of [ 124-25-4 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.93
Num. rotatable bonds :	12
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	69.61
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.63
Log Po/w (XLOGP3) :	5.97
Log Po/w (WLOGP) :	4.89
Log Po/w (MLOGP) :	3.8
Log Po/w (SILICOS-IT) :	5.08
Consensus Log Po/w :	4.67

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.13
Solubility :	0.0159 mg/ml ; 0.0000749 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.1
Solubility :	0.000167 mg/ml ; 0.000000786 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-5.08
Solubility :	0.00177 mg/ml ; 0.00000832 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	2.04

Safety of [ 124-25-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 124-25-4 ]

* 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 [ 124-25-4 ]

[ 124-25-4 ] Synthesis Path-Downstream 1~31

1
[ 112-72-1 ]
[ 124-25-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at 5 - 15℃; for 0.05h;	8.1 8.1 Tetradecanal A solution of oxalylchloride (8.0 mL, 88.0 mmol, 2.2 eq.) in abs. dichloromethane (200 mL) was treated with DMSO (13.6 mL, 192 mmol, 4.8 eq.) at -60 °C. After 3 min the reaction mixture was warmed to approx. 15 °C. Then a solution of tetradecan-1 -ol (8.56 g, 40.0 mmol) in dry dichloromethane (40 mL) and after further 3 min triethylamine (28 mL, 200 mmol, 5.0 eq.) were added. Then the reaction mixture was slowly warmed to 5 °C and quenched by addition of water (200 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (3 χ 100 mL). The combined organic phases were washed with brine (1 χ 200 mL) and dried over MgS04. The solvent was removed under reduced pressure and the product was isolated as a white solid, which was used in the next reaction without purification. Yield: 10.4 g (100%), purity: 98% (GC). 41 M.p.: 24 °C 1H-NMR (CDCIs, 300 MHz) δ [ppm]: 0.88 (t, 3JH,H = 6.7 Hz, 3 H, 14-CH3), 1 .20-1 .40 (m, 20 H, 4-CH2 to 13-CH2), 1 .63 (m, 2 H, 3-CH2), 2.43 (m, 2 H, 2-CH2), 9.76 (t, 3JH,H = 1 .8 Hz, 1 H, 1 - CHO). 13C-NMR (CDCI3, 75 MHz) δ [ppm]: 14.0 (q, C-14), 22.0 (t, C-3), 22.6 (t, C-13), 29.2, 29.4, 29.5, 29.6, 29.7 (t, C-4 to C-1 1 ), 31.9 (t, C-12), 43.8 (t, C-2), 202.8 (d, C-1 ). Ref.: Synthesis according to G. S. Nikolova, Dissertation, Universitat Mijnster, 2005. Spectroscopic data agree with those given in the literature.
100%	Stage #1: 1-Tetradecanol With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -60 - 15℃; for 0.1h; Stage #2: With triethylamine In dichloromethane; dimethyl sulfoxide at 5℃;	8.1 8.1 Tetradecanal 8.1 Tetradecanal10353] A solution of oxalylchloride (8.0 mE, 88.0 mmol,2.2 eq.) in abs. dichloromethane (200 mE) was treated with DMSO (13.6 mE, 192 mmol, 4.8 eq.) at -60° C. Afier 3 mm the reaction mixture was warmed to approx. 15° C. Then a solution of tetradecan-i -ol (8.56 g, 40.0 mmol) in dry dichloromethane (40 mE) and afier thrther 3 mm triethylamine (28 mE, 200 mmol, 5.0 eq.) were added. Then the reaction mixture was slowly warmed to 5° C. and quenched by addition of water (200 mE). The phases were separated and the aqueous phase was extracted with dichloromethane (3x100 mE). The combined organic phases were washed with brine (1 x200 mE) and dried over Mg504. The solvent was removed under reduced pressure and the product was isolated as a white solid, which was used in the next reaction without purification. Yield: 10.4 g (100%), purity: 98% (GC).j0354] M.p.: 24° C.j0355] ‘R-NMR (CDC13, 300 MHz) ö [ppm]: 0.88 (t, 3Hii=6.7 Hz, 3R, 14-CR3), 1.20-1.40 (m, 20R, 4-CR2 to 13-CR2), 1.63 (m, 2R, 3-CR2), 2.43 (m, 2R, 2-CR2), 9.76 (t,3JH,1r4.8 Hz, 1R, 1-CRO).j0356] ‘3C-NMR (CDC13, 75 MHz) ö [ppm]: 14.0 (q, C-14), 22.0 (t, C-3), 22.6 (t, C-13), 29.2,29.4,29.5,29.6,29.7 (t, C-4 to C-li), 31.9 (t, C-12), 43.8 (t, C-2), 202.8 (d, C-i). j0357] Ref.: Synthesis according toG. 5, Nikolova, Dissertation, Universitt Münster, 2005.j0358] Spectroscopic data agree with those given in the literature.
100%	With Dess-Martin periodane In dichloromethane at 20℃; for 3h;	Tetradecanal 17 DMP (5.94 g, 14.0 mmol, 1.5 eq) was added to a solution of tetradecanol 16 (2.00 g, 9.3 mmol) in DCM (30 mL) and the mixture was stirred for 3 h at RT. A mixture of sat. aq. NaHCO3:Na2S2O3(1N) (1:1) (120 mL) was added and the mixture was extracted with Et2O (90 mLx2). The combined organic layers were washed with water (30 mL), brine (90 mL), dried over MgSO4, filtered and concentrated in vacuo to afford the aldehyde 17 as a white solid without any further purification (1.97 g, quantitative).

98%	With Dess-Martin periodane In dichloromethane at 20℃; for 0.75h;
96%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate at 70℃; for 1h;	4.5. Oxidation of 1-tetradecanol to 1-tetradecanal (9) with IBX To 1-tetradecanol (2.7 g, 12.6 mmol, 1 equiv) in EtOAc wasadded IBX (10.6 g, 3 equiv) at rt and the reaction mixture wasrefluxed at 70 C until the starting material was consumed asshown by TLC (1 h). After completion of the reaction, the mixturewas filtered and concentrated under reduced pressure to give aldehyde9, which was characterized by NMR; 1H NMR (300 MHz,CDCl3): d = 0.86 (t, 3H, J = 7.3 Hz), 1.25 (s, 20H), 1.26 (m, 2H),2.35 (m, 2H), 9.75 (t, 1H, J = 2.4 Hz); 13C NMR (75.49 MHz, CDCl3)d 14.5, 22.5, 23.1, 25.1, 29.4, 29.6, 29.7, 30.0, 32.3, 34.3, 44.3,203.0. Yield: 2.57 g (96%).
94%	With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane for 0.25h; cooling;
92%	With pyridinium chlorochromate In dichloromethane
92%	Stage #1: 1-Tetradecanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.75h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -78 - -50℃; Inert atmosphere;
91%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at 0℃; for 1.5h;	1.1.1 Step 1.1: 1-Tetradecanal To a solution of 1-tetradecanol (110.0 g; 0.513 mol) and trichloroisocyanuric acid (178.1 g; 0.77 mol) in methylene chloride (1500 ml) at -30° C. was added (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl (TEMPO) (800 mg; 0.051 mol). The reaction mixture was stirred for 1.5 h at 0° C. and filtered on celite. The organic phase collected was then washed with a saturated solution of Na2CO3 (800 ml) followed by HCl 1N (800 mL). It was then dried over MgSO4, filtered and concentrated under vacuum to give rise to the title compound as white solid (99.6 g; 91%).
91%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -30 - 0℃; for 1.5h;	1.1.1 Step 1.1: 1-Tetradecanal [00202] To a solution of 1-tetradecanol (110.0 g ; 0,5 13 mol) and trichioroisocyanuric acid (178.1 g ; 0,77 mol) in methylene chloride (1500 ml) at -30°C was added (2,2,6,6- Tetramethylpiperidin-1-yl)oxyl (TEMPO) (800 mg ; 0.05 1 mol). The reaction mixture wasstirred for 1.5 h at 0°C and filtered on celite. The organic phase collected was then washed with a saturated solution of Na2CO3 (800 ml) followed by HC1 iN (800 mL). It was then dried over Mg504, filtered and concentrated under vacuum to give rise to the title compound, 1- tetradecanal, as white solid (99.6 g ; 91%).
90%	With pyridinium chlorochromate In dichloromethane
88%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 24h;
88%	With 1-methyl-1H-imidazole; copper (I) iodide; C₂₀H₂₅N₄O₂ In acetonitrile at 25℃; for 8h;
87%	With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 2h;
85%	With nitroacetic acid ethyl ester; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran room temperature for 2 h, refluxed for 2h;
85%	With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;
85%	With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - -40℃;
85%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione
85%	With pyridine; chromium(VI) oxide; mesoporous silica In dichloromethane for 1.5h; Inert atmosphere;
78%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 3h;
76%	With pyridinium chlorochromate
75%	With dimethyl selenoxide In benzene for 6h; Heating;
72%	With tetrabutylammonium bromide; dihydrogen peroxide In dichloromethane at 20℃; for 24h;
70%	With pyridinium dichromate In dichloromethane for 20h;	Synthesis of tetradecanal To asuspension of PDC (2 eq., 5.26 g, 14 mmol) in CH2Cl2 (15 ml) was added 1.5 g detetradecanol (7 mmol, 1 eq.). The mixture was stirred for 20 h, thenfiltered over diatomaceous earth and washed with pentane. Afterevaporation of solvents, tetradecanal (colorless oil, 1.04g, 70 %)was purified by column chromatography on silical gel (CH2Cl2 100 %).
67%	With 1-iodylbenzene; bromine; NaNO₂ In water monomer at 55℃; for 2h;
30%	With barium permanganate In benzene for 6h; Heating;
	With N-Methylmorpholine N-oxide In acetonitrile at 25℃;
	With chromic acid; acetic acid
	With nickel at 250℃;
	With pyridine-SO₃ complex; triethylamine In dimethyl sulfoxide for 0.5h; Ambient temperature;
	With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃;
	With Celite; pyridinium chlorochromate In dichloromethane at 20℃; for 4h;
1.7 g	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 1.5h;
	With pyridinium chlorochromate
	With pyridinium chlorochromate In dichloromethane
	With pyridine-SO₃ complex; triethylamine In dichloromethane; dimethyl sulfoxide at 0 - 20℃; for 2h;
	With pyridinium chlorochromate In dichloromethane for 2h;
	Multi-step reaction with 2 steps 1: selenium dioxide 2: 177 °C / Irradiation_.mit UV-Licht
	With piridinium dichromate In trifluorormethanesulfonic acid
	With pyridinium chlorochromate Inert atmosphere;
	With Dess-Martin periodane In dichloromethane at 0℃; for 0.75h;	5.1.1. General procedure for the synthesis of aldehydes 12a,b. Example: tetradecanal (12a)^[67]^and77 Y.-H. Chang, B.-J. Uang, C.-M. Wu and T.-H. Yu, Synthesis 1990 (1990), p. 1033. Full Text via CrossRef \| View Record in Scopus \| Cited By in Scopus (5)^[77] General procedure: To a solution of commercial tetradecan-1-ol (0.72 g, 3.37 mmol) in DCM (20 mL) at 0 °C Dess-Martin periodinane (DMP) (1.53 g, 3.60 mmol) was added. After completion (45 min, TLC monitoring), the reaction crude was directly purified by column chromatography (silica gel, CHCl3/n-hexane, 3:1) to afford the required aldehyde as a waxy white solid (187 mg, 98% yield). 1H NMR (CDCl3): δ 0.88 (t, 3H, CH3), 1.26-1.29 (m, 20H, 10 × CH2), 1.60-1.65 (m, 2H, CH2), 2.40-2.50 (m, 2H, CH2), 9.77 (t, 1H, H-1); MS (EI, 70 eV) m/z (%): 212.
	With pyridinium chlorochromate
1.28 g	With Dess-Martin periodane In dichloromethane at 0℃;
	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In tetrahydrofuran at 20℃; for 18h;	General procedure for A General procedure: To (diacetoxyiodo)benzene (80.5 mg, 0.25mmol) and 2,2,6,6-tetramethylpiperidine 1-oxyl (3.9 mg, 25μmol) was added alcohol 1a-g (1.1 equiv, 0.275 mmol) in THF (1.0 mL). The mixture was stirred atroom temperature for 18 h. Benzoyl peroxide (66.6 mg, 0.275 mmol) and a solution of α,α -diphenyl-2-pyrrolidinemethanol trimethylsilyl ether (10 mol % or 20 mol %) in THF (1.0 mL) were added. The mixture was stirred for 5h at room temperature, NaBH4 (37.9 mg, 1 mmol) was added and the mixturewas stirred overnight. A saturated solution of NaHCO3 was added and the mixture extracted twice with dichloromethane. Organic phases were combined, dried over MgSO4 and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel using pentane/EtOAc(85/15) as eluent provided the expected compound 4a-g.
	With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 1h;	6 Example 6. Preparation of Compounds 24, 46, 48 and 50 by Swern oxidation DMSO (14 mmol) was added drop vise to a stirred solution of oxalyl chloride (5 mmol) in DCM (20 mL) at -78 °C, after added the mixture was stirred at -78 °C for 20 min, then alkanol (4 mmol) was added dropvise and stirred at -78 °C for 1 h, Et3N (1 mL) was added and the temperature was slowly elevated to rt., then water was added, the separated DCM layer was washed with brine, concentrated under vacuum, the residue was purified by flash column chromatography to give a colorless oil.
95 %Chromat.	With hydrogenchloride; NaBrO₃; N-(1-oxo-2,2,6,6-tetramethylpiperidin-4-yl)-benzoylamide In dichloromethane; water monomer at 20℃; for 4h;
	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutylammonium bromide In dichloromethane at 20℃; for 1.5h;	Oxidation Procedure General procedure: Alcohol (1 mmol) was added to amixture of BAIB (1.1 mmol) and bromide anions (0.2 mmol) inEtOAc (1.5 mL), and the mixture was stirred at room temperaturefor 24 h. The solvent was removed under reduced pressureand the crude product was checked by 1H NMR spectroscopy. Incase of p-nitrobenzyl alcohol, anisole, and p-chlorobenzylalcohol oxidations, the residue was purified by chromatography[PE to separate iodobenzene and PE-EtOAc (10:1) to separatethe corresponding aldehyde].
93 %Chromat.	With iron (ΙΙΙ) nitrate nonahydrate; 9-azabicyclo<3.3.1>nonane-N-oxyl In acetonitrile at 20℃; for 8h;
72%Chromat.	With Ni nanoparticle immobilized-sulfonated imidazolium-based ionic liquid-functionalized magnetic silica nanoparticles; air In water monomer for 1h; Heating;
99 %Chromat.	With 5H₃N5H⁽¹⁺⁾IMo₆O₂₄^(5-); oxygen; anhydrous Sodium acetate In water monomer; acetonitrile at 70℃; for 12h; Green chemistry;
16.1 g	With Dess-Martin periodane In dichloromethane at 20℃; for 3h; Schlenk technique; Inert atmosphere;

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[42]Location in patent: experimental part Milite, Ciro; Castellano, Sabrina; Benedetti, Rosaria; Tosco, Alessandra; Ciliberti, Carmen; Vicidomini, Caterina; Boully, Ludovic; Franci, Gianluigi; Altucci, Lucia; Mai, Antonello; Sbardella, Gianluca [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 12, p. 3690 - 3701]
[43]Location in patent: experimental part Dittrich, Birger; Harrowfield, Jack M.; Koutsantonis, George A.; Nealon, Gareth L.; Skelton, Brian W. [Dalton Transactions, 2010, vol. 39, # 14, p. 3433 - 3448]
[44]Zhang, Hua; Xiao, Xue; Conte, Melissa M.; Khalil, Zeinab; Capon, Robert J. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 48, p. 9671 - 9676]
[45]Hermange, Philippe; Portalier, François; Thomassigny, Christine; Greck, Christine [Tetrahedron Letters, 2013, vol. 54, # 9, p. 1052 - 1055]
[46]Current Patent Assignee: VIRGINIA COMMONWEALTH UNIVERSITY - WO2013/119774, 2013, A1 Location in patent: Page/Page column 28
[47]Shen, Jiaxuan; Sun, Jiangkai; Qin, Shuangshuang; Chu, Changhu; Liu, Renhua [Chinese Journal of Chemistry, 2014, vol. 32, # 5, p. 405 - 409]
[48]Salvo, Anna Maria Pia; Campisciano, Vincenzo; Beejapur, Hazi Ahmad; Giacalone, Francesco; Gruttadauria, Michelangelo [Synlett, 2015, vol. 26, # 9, p. 1179 - 1184]
[49]Wang, Lianyue; Shang, SenSen; Li, Guosong; Ren, Lanhui; Lv, Ying; Gao, Shuang [Journal of Organic Chemistry, 2016, vol. 81, # 5, p. 2189 - 2193]
[50]Hosseinzadeh-Khanmiri, Rahim; Kamel, Yaser; Keshvari, Zahra; Mobaraki, Ahmad; Shahverdizadeh, Gholam Hossein; Vessally, Esmail; Babazadeh, Mirzaagha [Applied Organometallic Chemistry, 2018, vol. 32, # 9]
[51]Zhang, Mengqi; Zhai, Yongyan; Ru, Shi; Zang, Dejin; Han, Sheng; Yu, Han; Wei, Yongge [Chemical Communications, 2018, vol. 54, # 72, p. 10164 - 10167]
[52]Lauberteaux, Jimmy; Crévisy, Christophe; Baslé, Olivier; De Figueiredo, Renata Marcia; Mauduit, Marc; Campagne, Jean-Marc [Organic Letters, 2019, vol. 21, # 6, p. 1872 - 1876]
[53]Grosse, Michel; Günther, Kerstin; Jordan, Paul M.; Roman, Dávid; Werz, Oliver; Beemelmanns, Christine [ChemBioChem, 2022, vol. 23, # 9]

2
[ 112-64-1 ]
[ 629-50-5 ]
[ 124-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pumice stone; platinum at 220 - 230℃; Hydrogenation;

Reference： [1]Escourrou [Bulletin de la Societe Chimique de France, 1939, vol. <5>6, p. 1180]

3
[ 124-25-4 ]
[ 23778-52-1 ]
[ 41293-73-6 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1973,vol. 46,p. 623 - 626

4
[ 67-56-1 ]
[ 124-25-4 ]
[ 124-10-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-iodo-succinimide; potassium carbonate for 3.5h; Ambient temperature;

Reference： [1]McDonald, Chriss; Holcomb, Harald; Kennedy, Kenneth; Kirkpatrick, Elijah; Leathers, Todd; Vanemon, Penny [Journal of Organic Chemistry, 1989, vol. 54, # 5, p. 1213 - 1215]

5
[ 124-25-4 ]
[ 86120-40-3 ]
[ 86120-41-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With lithium diisopropyl amide In tetrahydrofuran at -40℃;
60%	With n-butyllithium; hexane; diisopropylamine In tetrahydrofuran 1) -40 deg C, 2 h, 2) r.t., 12 h;

Reference： [1]Garigipati, Ravi S.; Weinreb, Steven M. [Journal of the American Chemical Society, 1983, vol. 105, # 13, p. 4499 - 4501]
[2]Garigipati,R.S.; Freyer,A.J.; Whittle,R.R. [Journal of the American Chemical Society, 1984, vol. 106, p. 7861]

6
[ 124-25-4 ]
[ 60-92-4 ]
(4aR,6R,7R,7aS)-2-Oxo-6-[6-tetradec-(Z)-ylideneamino-purin-9-yl]-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 2212 - 2219

7
[ 124-25-4 ]
[ 1668-08-2 ]
(3S,4S,5S)-3,4-Dihydroxy-5-((S)-2-tridecyl-[1,3]dioxolan-4-yl)-dihydro-furan-2-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 1787 - 1790

8
[ 124-25-4 ]
[ 40018-25-5 ]
[ 120135-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfur; triethylamine In N,N-dimethyl-formamide at 50 - 60℃; for 4h;

Reference： [1]Kawakami; Kitani; Yuasa; Abe; Moriwaki; Kagoshima; Terasawa; Tahara [European Journal of Medicinal Chemistry, 1996, vol. 31, # 9, p. 683 - 692]

9
[ 124-25-4 ]
[ 1779-58-4 ]
[ 2825-81-2 ]
[ 2825-80-1 ]

Reference： [1]Helvetica Chimica Acta,2003,vol. 86,p. 310 - 323

10
[ 13138-33-5 ]
[ 124-25-4 ]
(3-tetradecylamino-propyl)-phosphonic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3495 - 3499

11
[ 124-25-4 ]
[ 24850-33-7 ]
(4R)-heptadec-1-en-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: myristylaldehyde With bis[(R)-binaphthoxy](isopropoxy)titanium} oxide In dichloromethane at 20℃; for 0.5h; Molecular sieve; Stage #2: allyltributylstanane at -78 - -20℃; for 72h; Molecular sieve; Reflux; enantioselective reaction;	(R)-heptadec-1-en-4-ol (16): To the stirred solution of oven-dried 4-Å molecular sieves (5g) in CH2Cl2 (15 mL) under N2 atmosphere, wasadded (S)-BINOL (108 mg, 0.38 mmol),Ti(OiPr)4 (0.11 mL, 0.38 mmol) in CH2Cl2.The reaction mixture was heated at reflux for a period of 1h, and then allowedto cool to room temperature. Tetradecanal (0.8 g, 3.77 mmol) in CH2Cl2(5 mL), was added to the reaction mixture. After the mixture stirred for30min at room temperature, cooled to -78 °C, allyltributyltin (1.4 mL, 4.53 mmol) wasslowly added. The reaction mixture as stirred for an additional 10min at -78 °C,then kept in a -20 °C. After 72h, the reaction mixture was filtered through apad of celite in to a 100 mL flask that contained a stirring saturated aqueousNaHCO3 solution (10 mL) and the resulting mixture was stirred for 1h,then the layers were separated. The aqueous layer was extracted with CH2Cl2(2 × 10 mL). The combined organic layers were washed with brine (10 mL), driedwith Na2SO4, filtered, and concentrated under reducedpressure to give the crude product. The crude residue was purified by columnchromatography (hexane/EtOAc:9:1 ) to give alcoholic compound 16 as semi solid in yield (843 mg, 88%); [α]25D : +8 (c1.2, CHCl3). 1H NMR (500 MHz, CDCl3): δ 5.87-5.79 (m, 1H), 5.16-5.11 (m, 2H), 3,67-3.62 (m, 1H), 2.33-2.27 (m, 2H), 2.17-2.11 (m, 1H), 1.71 (br.s, 1H), 1.49-1.41 (m, 2H),1.34-1.22 (m, 22H), 0.88 (t, J = 6.8Hz, 3H). 13C NMR (75 MHz, CDCl3): δ 134.8117.7, 70.6, 41.8, 36.7, 31.8, 29.6, 29.3, 25.6, 22.6, 14.0. (ESI-MS): m/z 277[M+Na]. IR (neat) nmax: 3361, 2924, 2853, 1643, 1463, 1042, 994, 912.
86%	In dichloromethane at -15 - 0℃; for 24h;
82%	Stage #1: myristylaldehyde With bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide at 20℃; for 2h; Stage #2: allyltributylstanane at 0℃; for 12h; optical yield given as %ee; enantioselective reaction;

Reference： [1]Raju, Atla; Yugendar Reddy; Sabitha, Gowravaram [Tetrahedron Letters, 2015, vol. 56, # 40, p. 5474 - 5476]
[2]Chandrasekhar; Rambabu; Shyamsunder [Tetrahedron Letters, 2007, vol. 48, # 27, p. 4683 - 4685]
[3]Location in patent: scheme or table Das, Biswanath; Krishnaiah, Martha; Sudhakar, Chithaluri [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2303 - 2305]

12
[ 124-25-4 ]
[ 17361-44-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: MgSO₄ / CH₂Cl₂ / 0 - 20 °C 2: NaBH₄ / CH₂Cl₂; methanol / 4 h / 20 °C
	Multi-step reaction with 2 steps 1: MgSO₄ / CH₂Cl₂ / 3 h / 0 - 20 °C 2: NaBH₄ / CH₂Cl₂; methanol / 4 h / 0 - 20 °C

Reference： [1]Singh, Rajkumar Sunil; Mukherjee, Koushik; Banerjee, Rajkumar; Chaudhuri, Arabinda; Hait, Samik Kumar; Moulik, Satya Priya; Ramadas, Yerramsetti; Vijayalakshmi, Amash; Rao, Nalam Madhusudhana [Chemistry - A European Journal, 2002, vol. 8, # 4, p. 900 - 909]
[2]Banerjee; Mahidhar; Chaudhuri; Gopal; Rao [Journal of Medicinal Chemistry, 2001, vol. 44, # 24, p. 4176 - 4185]

13
[ 124-25-4 ]
[ 16611-84-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 50 percent / lithium bis(trimethylsilyl)amide / -78 °C 2: H₂ / 5percent platinum on carbon 3: H₂O; dimethylsulfoxide / Heating; alkaline hydrolysis 4: boron tribromide

Reference： [1]Kubo, Isao; Kim, Mujo; Komatsu, Sakae; Yamagiwa, Yoshiro; Ohashi, Kinji; et al. [Chemistry Letters, 1987, p. 1101 - 1104]

14
[ 638-58-4 ]
[ 124-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride 2: tin (II)-chloride; hydrogen chloride; diethyl ether / und beim Verseifen des Reaktionsprodukts mit warmem Wasser

Reference： [1]Stephen [Journal of the Chemical Society, 1925, vol. 127, p. 1876]

15
[ 124-25-4 ]
[ 1185-53-1 ]
[ 18360-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: myristylaldehyde; tris hydrochloride In methanol; water for 0.5h; Stage #2: With sodium tetrahydroborate In methanol; water	2 Two g of 2-amino-2-(hydroxymethyl)propane-l,3-diol hydrochloride were dissolved in 50 ml H2O and 50 ml methanol in a round bottom flask. To the magnetically-stirred solution, 4 ml of tetra decyl aldehyde (tetradecanal) were added. The mixture was stirred for 30 min, after which 1.8 g of NaBH4 was added in several portions during 3 hours. The mixture was left to stir overnight, the solution was transferred to a separatory funnel, 50 ml of H2O and 100 ml dichloromethane were added and the solvent mixture was shaken. The lower phase was collected, the aqueous-methanol phase was extracted twice with 50 ml 3:1 dichloromethane:methanol, the 3 lower phases were combined and shaken with 75 ml H2O. The organic phase was dried with MgSθ4, filtered and evaporated to dryness. The residue was crystallized from ethanol:H2O. Yield: 1.1 g.

Reference： [1]Current Patent Assignee: HADASSAH MEDICAL ORGANIZATION; Yissum Research & Development (in: Hebrew University); HEBREW UNIVERSITY OF JERUSALEM - WO2009/60457, 2009, A1 Location in patent: Page/Page column 41-42

16
[ 124-25-4 ]
[ 17114-97-5 ]
[ 1162684-86-7 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 4156 - 4164
[2]European Journal of Organic Chemistry,2012,p. 345 - 352

17
[ 124-25-4 ]
[ 17114-97-5 ]
[ 1357395-63-1 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 345 - 352

18
[ 2648-71-7 ]
[ 124-25-4 ]
[ 1352303-08-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: 3-bromo-3-methyl-2-butanone With N,N-dimethyl-ethanamine; (chlorobis((2S,3R)-3,6,6-trimethylbicyclo[3.1.1]heptan-2-yl)borane) In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: myristylaldehyde In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere; Stage #3: With dihydrogen peroxide In tetrahydrofuran; methanol at -78 - 20℃; for 3h; Inert atmosphere;
56%	Stage #1: 3-bromo-3-methyl-2-butanone With N,N-dimethyl-ethanamine; (-)-diisopinocamphenylborane chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: myristylaldehyde In tetrahydrofuran at -78 - 20℃; for 3h; Stage #3: With dihydrogen peroxide In tetrahydrofuran; methanol at -78 - 20℃;	8 Preparation of 2-bromo-5-hydroxy-2-methyloctadecan-3-one (16) (-)-DIP-Cl (chlorobis((2S,3R)-3,6,6-trimethylbicyclo[3.1.1]heptan-2-yl)borane) (55% wt in THF, 21 mL, 33 mmol) and dimethylethylamine (9.8 mL, 91 mmol) was dissolved in dry THF (100 mL) and cooled to 0° C. 3-Bromo-3-methylbutan-2-one (5.0 g, 30 mmol) was added dropwise and let stir at 0° C. for 30 min. The solution became cloudy and slightly pink. It was cooled the reaction to -78° C. and tetradecanal (7.1 g, 33 mmol) was added. The solution was stirred at -78° C. for 3 hrs; warmed to ambient temperature; cooled back to -78° C.; 50 mL of MeOH and 20 mL of 30% H2O2 was added slowly (exothermic); and let stir for 3 hrs more warming to ambient temperature. Water was added, and the product was extracted with ether (3×500 mL). The combined organics were washed with brine, dried over magnesium sulfate, and concentrated to give a colorless viscous oil. The product was purified via automated flash chromatography (silica, 0-25% EtOAc:Hex) to give a waxy solid. 6.38 g (56%). Subsequent mosher ester analysis showed a racemic mixture of products. Rf=0.3 (20% EtOAc:Hex); mp: 30° C.; 1H NMR [600 MHz, CDCl3] δ 4.06 (br s, 1H), 3.04 (dd, 1H, J=2.4, 17.4 Hz), 2.91 (br s, 1H), 2.87 (dd, 1H, J=9.0, 17.4 Hz), 1.86 (d, 6H, J=9.6 Hz), 1.57-1.53 (m, 1H), 1.47-1.43 (m, 2H), 1.40-1.24 (m, 21H), 0.88 (t, 3H, J=7.0 Hz); 13C NMR [100 MHz, CDCl3] δ 206.9, 68.49, 68.46, 63.8, 43.1, 36.7, 32.1, 29.9, 29.79, 29.76, 29.6, 29.5, 29.4, 25.7, 22.9, 14.3 ppm; HRMS (ESI) m/z 377.20548 (Theo. for C19H37BrO2+H: 377.20497); IR (ATR) 2921, 2852, 1710, 1627, 1459, 1370, 1109, 1077, 997, 721 cm-1.

Reference： [1]Meyer, Esmeralda V. S.; Holt, Jason J.; Girard, Kathryn R.; Ballie, Mark T.; Bushnev, Anatoliy S.; Lapp, Stacey; Menaldino, David S.; Arrendale, Richard F.; Reddy, G. Prabhakar; Evers, Taylor J.; Howard, Randy B.; Culver, Deborah G.; Liotta, Dennis C.; Galinski, Mary R.; Natchus, Michael G. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 1, p. 43 - 47]
[2]Current Patent Assignee: EMORY UNIVERSITY - US2014/309275, 2014, A1 Location in patent: Paragraph 0197

19
[ 124-25-4 ]
[ 911040-42-1 ]
(R)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-hydroxyhexadecan-1-one [ No CAS ]
1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-hydroxyhexadecan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone With titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: myristylaldehyde In dichloromethane at -78℃; for 0.75h; Inert atmosphere; diastereoselective reaction;	(R)-1-[(R)-4-Benzyl-2-thioxothiazolidin-3-yl]-3-hydroxyhexadecan-1-one (13) TiCl4 (2.62 mL, 23.9 mmol) and DIPEA (4.16 mL, 23.9 mmol)were successively added to a stirred solution of (R)-12 (6.0 g, 23.9mmol) in CH2Cl2 (60 mL) at -78 °C under an N2 atm, and the resultingmixture stirred for 1 h. A solution of 1-tetradecanal (6) (7.6 g,35.85 mmol) in CH2Cl2 (30 mL) was added via a cannula at -78 °C.The mixture was stirred for 45 min and then the reaction wasquenched with half sat. aq NH4Cl solution. The organic layer wasseparated and the aq layer was extracted with CH2Cl2 (3 × 50 mL).The combined organic layers were washed with H2O (3 × 15 mL)and brine (3 × 5 mL), dried over anhydrous Na2SO4, filtered, andconcentrated in vacuo. Purification of the residue by column chromatography(hexane-EtOAc, 20:1 to 10:1) gave the desired majoraldol adduct.Yield: 6.693 g, 14.45 mmol (72%); yellow oil; [α]D25 -126.84 (c1.0, CHCl3).IR (KBr): 3155, 2925, 1695, 745, 700 cm-1.1H NMR (300 MHz, CDCl3): δ = 7.41-7.24 (m, 5 H), 5.44-5.36 (m,1 H), 4.20-4.09 (m, 1 H), 3.68 (dd, J = 16.0, 2.0 Hz, 1 H), 3.45-3.37(dd, J = 12.0, 8.0 Hz, 1 H), 3.29-3.01 (m, 3 H), 2.91 (d, J = 12.0 Hz,1 H), 2.71 (br s, 1 H), 1.65-1.22 (m, 24 H), 0.89 (t, J = 7.0 Hz, 3 H).13C NMR (75 MHz, CDCl3): δ = 202.2, 173.0, 136.1, 129.4, 128.6,127.2, 68.8, 67.7, 45.4, 36.4, 35.8, 31.8, 31.6, 29.9, 29.7, 25.2, 22.2,14.6.ESI-MS: m/z = 464 [M + H]+.HRMS (ESI): m/z [M + Na]+ calcd for C26H41O2NNaS2: 486.24709;found: 486.24729.

Reference： [1]Maram, Lingaiah; Das, Biswanath [Synthesis, 2014, vol. 46, # 9, p. 1205 - 1210]

20
[ 591-12-8 ]
[ 124-25-4 ]
C₁₉H₃₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-methyl-2-furanone; myristylaldehyde With di-n-butylboryl trifluoromethanesulfonate; triethylamine In dichloromethane at -78 - 20℃; for 20h; Inert atmosphere; Stage #2: With dihydrogen peroxide In methanol at 20℃; for 2h;	Preparation of akolactone A (3) and α-alkylidenebutenolide (7) To a stirred solution of angelica lactone 4 (200 mg, 2.04 mmol, 1.0 equiv) and Hünig base (1.4 mL, 8.16 mmol, 4.0 equiv) in dry CH2Cl2 (12 mL) under argon at -78 °C was dropwise added n-Bu2BOTf (1.0 M in CH2Cl2, 4.3 mL, 4.29 mmol, 2.1 equiv). The resulted solution was stirred for 30 min before dropwise addition of a solution of myristyl aldehyde 5(650 mg, 3.06 mmol, 1.5 equiv) in dry CH2Cl2 (2 mL). The reaction was stirred from -78 °C to rt for 20 h, quenched by addition to pH 7 phosphate buffer. The mixture was extracted twice with ether (30 mL) and the combined ether extracts were washed with brine and concentrated in vacuo. The crude oil was then dissolved in methanol (6 mL) at 0 °C and 30 % hydrogen peroxide (2 mL) was added. After the mixture was stirred at room temperature for 2h, water (15 mL) was added. The milky mixture was concentrated in vacuo to remove most of the methanol. The residue was extracted twice with ether (30 mL) and the combined ether solution was washed with 5 % aqueous sodium bicarbonate, sodium bisulfite and brine, dried over MgS04, and concentrated in vacuo to afford the crude alcohol which was directly used inthe next step. Al2O3 (645 mg, 6.33 mmol, 3.1 equiv) and pyridine (14 mL) was added and thereaction was refluxed overnight (21 h). After completion, the reaction was filtered on celite to remove alumina and the solvent was removed under vaccum. The residue was purified by flash chromatography on silica gel (hexane / EtOAc, 90 : 10) to yield 2 isomers 7 as a colorless oil (167 mg, 28 %) and 3 as a yellow oil (225 mg, 38 %).
	Stage #1: 5-methyl-2-furanone With N-ethyl-N,N-diisopropylamine; di-n-butylboron trifluoromethanesulphonate In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: myristylaldehyde In dichloromethane at -78 - 20℃; for 20h; regioselective reaction;	Preparation of akolactone A (3) and α-alkylidenebutenolide (7) To a stirred solution of angelica lactone 4 (200 mg, 2.04 mmol, 1.0 equiv) and Hünig base (1.4 mL, 8.16 mmol, 4.0 equiv) in dry CH2Cl2 (12 mL) under argon at -78 °C was dropwise added n-Bu2BOTf (1.0 M in CH2Cl2, 4.3 mL, 4.29 mmol, 2.1 equiv). The resulted solution was stirred for 30 min before dropwise addition of a solution of myristyl aldehyde 5(650 mg, 3.06 mmol, 1.5 equiv) in dry CH2Cl2 (2 mL). The reaction was stirred from -78 °Cto rt for 20 h, quenched by addition to pH 7 phosphate buffer. The mixture was extracted twice with ether (30 mL) and the combined ether extracts were washed with brine and concentrated in vacuo. The crude oil was then dissolved in methanol (6 mL) at 0 °C and 30 % hydrogen peroxide (2 mL) was added. After the mixture was stirred at room temperature for 2h, water (15 mL) was added. The milky mixture was concentrated in vacuo to remove most of the methanol. The residue was extracted twice with ether (30 mL) and the combined ethersolution was washed with 5 % aqueous sodium bicarbonate, sodium bisulfite and brine, driedover MgS04, and concentrated in vacuo to afford the crude alcohol which was directly used in the next step.

Reference： [1]Boukouvalas, John; Jean, Marc-Alexandre [Tetrahedron Letters, 2014, vol. 55, # 30, p. 4248 - 4250]
[2]Boukouvalas, John; Jean, Marc-Alexandre [Tetrahedron Letters, 2014, vol. 55, # 30, p. A4248 - A4250]

21
[ 112-72-1 ]
[ 124-25-4 ]
[ 3234-85-3 ]
[ 544-63-8 ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen In n-heptane at 100℃; for 6h; Green chemistry;	2.4. Catalytic oxidation tests General procedure: Tests were conducted under atmospheric pressure at 80-120°C in a four-necked round bottom flask equipped with reflux condenser, oxygen feed, thermometer and a septum cap. In a typical test, catalyst was added (in a substrate/metal ratio(A/M) = 100-500 mol/mol) to 20 mL of 1-tetradecanol solution (0.1 M) in n-heptane or n-decane, with no base addition. The suspension was stirred and heated to the selected reaction temperature (TR). Once reached it, run time started when oxygen was bubbled through it with a flow rate of 30 mL/min, under near atmospheric pressure (P = 100 kPa), and the test was run for 6 h. Reaction monitoring was done by analyzing small aliquots of the reaction mixture taken at various intervals. Aliquots were syringe filtered (pore 0.45 m), and were analyzed by GC in a Varian 450 GC, usinga capillary DB wax column (15 m × 0.548 mm), He as the carrier gas and a FID detector. In all measurements the carbon balance was within 100 ± 3%. For comparative purposes, some similar tests were conducted under the same conditions using 1-octanol instead of 1-tetradecanol.
	With oxygen In decane at 120℃; for 6h;	Catalytic oxidation tests Tests were conducted under atmospheric pressure at 80-120 C in a four-necked round bottom flask equipped with reflux condenser,oxygen feed, thermometer and a septum cap. In a typical test, catalyst was added in a substrate/metal molar ratio (A/M) = 50-200 to 20 mL of 1-tetradecanol solution (0.1 M) in n-decane. No base was added. The suspension was stirred and heated to the selected reaction temperature (TR). Once reached it, run timestarted when oxygen was bubbled through it with a flow rate of30 mL/min, under near atmospheric pressure (P = 100 kPa), and thetest was run for 6 h. Reaction monitoring was done by analyzing small aliquots of the reaction mixture taken at various intervals. Aliquots were syringe filtered (pore 0.45 m), and analyzed by gas chromatography in a Varian 450 GC, using a capillary DBwax column (15 m×0.548 mm), He as the carrier gas and a flame

Reference： [1]Corberán, Vicente Cortés; Gómez-Avilés, Almudena; Martínez-González, Susana; Ivanova, Svetlana; Domínguez, María I.; González-Pérez, María Elena [Catalysis Today, 2014, vol. 238, p. 49 - 53]
[2]Martínez-González; Ivanova, Svetlana; Domínguez, María I.; Cortés Corberán [Catalysis Today, 2016, vol. 278, p. 113 - 119]

22
[ 112-72-1 ]
[ 124-25-4 ]
[ 3234-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen In n-heptane at 80℃; for 6h; Green chemistry;	2.4. Catalytic oxidation tests General procedure: Tests were conducted under atmospheric pressure at 80-120°C in a four-necked round bottom flask equipped with reflux condenser, oxygen feed, thermometer and a septum cap. In a typical test, catalyst was added (in a substrate/metal ratio(A/M) = 100-500 mol/mol) to 20 mL of 1-tetradecanol solution (0.1 M) in n-heptane or n-decane, with no base addition. The suspension was stirred and heated to the selected reaction temperature (TR). Once reached it, run time started when oxygen was bubbled through it with a flow rate of 30 mL/min, under near atmospheric pressure (P = 100 kPa), and the test was run for 6 h. Reaction monitoring was done by analyzing small aliquots of the reaction mixture taken at various intervals. Aliquots were syringe filtered (pore 0.45 m), and were analyzed by GC in a Varian 450 GC, usinga capillary DB wax column (15 m × 0.548 mm), He as the carrier gas and a FID detector. In all measurements the carbon balance was within 100 ± 3%. For comparative purposes, some similar tests were conducted under the same conditions using 1-octanol instead of 1-tetradecanol.

23
[ 124-25-4 ]
[ 1779-49-3 ]
[ 13360-61-7 ]

Yield	Reaction Conditions	Operation in experiment
74%		Methyltriphenylphosphonium bromide (2.43 g, 6.80 mmol, 2.0 eq) was suspended in anhydrous THF (10 mL) and n-Buli (4.25 mL, 6.8 mmol, 2.0 eq) was added at 0 C. The reaction was then stirred for 10 min at 0 C. Tetradecanal 17 (0.72 g, 3.4 mmol) dissolved in anhydrous THF (10 mL) was added to the ylide at 0 C and the reaction mixture was stirred overnight at RT. Et2O(100 mL) was then added and the mixture was washed with water (2x 130 mL) and brine (60mL). Water layers were extracted with Et2O (50 mL) and the combined organics were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (100% PE) to yield 8 (530 mg, 74%) as a colorless oil.

Reference： [1]Chemical Communications,2015,vol. 51,p. 6161 - 6163

24
[ 626-29-9 ]
[ 124-25-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With P(p-CH₃OC₆H₄)3; methylphenylsilane; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 60℃; for 20h; Schlenk technique; Inert atmosphere;	6 General procedure: To a 10mL Schlenk flask with a magnetic stir bar, a carboxylic anhydride (1, 0.50mmol), Pd(dba)2 (0.025mmol) and P(p-OMeC6H4)3 (0.050mmol) were added. The flask was evacuated and backfilled with argon three times. Then, toluene (1.0mL) was added to the flask and the resultant solution was stirred at room temperature for 10min. After H2SiMePh (0.55mmol) was added to the flask, the reaction mixture was stirred at 40-120°C for 20h under an argon atmosphere. The reaction mixture was cooled to room temperature, the yield of aldehyde (2) was determined by GC analysis or the product was isolated with silica gel column chromatography. The yields of 2a, 2g, 2h, and 2j were determined by GC analysis based on the internal standard technique. 1H and 13C NMR spectra of isolated 2b, 2c, 2d, 2e, 2f, and 2i were good agreement with reported data.5.2.6 Tetradecanal (2i) White solid (90 mg, 82%), 1H NMR (400 MHz, CDCl3): δ 9.76 (t, J=1.4 Hz, 1H), 2.42 (td, J=7.6, 2.0 Hz, 2H), 1.66-1.59 (m, 2H), 1.34-1.23 (m, 20H), 0.88 (t, J=6.8 Hz, 3H).

Reference： [1]Fujihara, Tetsuaki; Hosomi, Takuro; Cong, Cong; Hosoki, Tomoya; Terao, Jun; Tsuji, Yasushi [Tetrahedron, 2015, vol. 71, # 26-27, p. 4570 - 4574]

25
[ 2437-56-1 ]
[ 201230-82-2 ]
[ 124-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; rhodium(I) dicarbonyl acetylacetonate In 1,2-dimethoxyethane at 80℃; for 18h; Autoclave;	Synthesis of aminonitriles 3a-e and amino acids 4a-e: General procedure: Following the typical procedure described above, Rh(acac)(CO)2 (2.6 mg, 0.01 mmol), xantphos (28.9 mg, 0.05 mmol) were placed in the autoclave. Then a solution of olefin (5 mmol) in DME (8 mL) was added via cannula, the autoclave was pressurized with 20 bar of CO/H2 equimolar mixture and the reaction was conducted for 18 h, upon stirring, at 80°C. After this period, the reactor was cooled to room temperature, an aqueous solution (2 mL) of NH4Cl (5.5 mmol) and NaCN (5.5 mmol) was added via inlet cannula and the reaction was kept at 50°C for 20 h. After work-up and purification, the resulting α-aminonitrile (4.1 mmol) was suspended in a concentrated HCl solution and stirred for 6 h at 40°C. The product was dissolved in methanol. After adjustment of the pH to the isoelectric point, using NH4OH (aq), the solvent was evaporated and the amino acid was obtained.

Reference： [1]Almeida, Ana R.; Carrilho, Rui M.B.; Peixoto, Andreia F.; Abreu, Artur R.; Silva, Artur; Pereira, Mariette M. [Tetrahedron, 2017, vol. 73, # 17, p. 2389 - 2395]

26
[ 627-82-7 ]
[ 124-25-4 ]
C₃₄H₆₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.28%	With p-octylbenzenesulfonic acid In water at 80℃; for 18h; Inert atmosphere; Green chemistry;	8 Example 8 In a three-necked round-bottomed flask equipped with an electric stirrer, a water separator, a condenser and a nitrogen inlet tube, 4.99 g of diglycerin was charged, followed by n-tetradecyl:Diglycerol = 1: 1.5 was added 4.25g n-tetradecyl, according to n-tetradecyl:Octyl benzene sulfonic acid = 1: 0.02 octylsulfonic acid 0.11g catalyst was added, according to n-tetradecanal: water = 1: 12 was added 4.32g of water under nitrogen atmosphere, heated to 80 ° C with stirring, the reaction after 18 hours Cool to room temperature,The resulting reaction solution was extracted with ethyl acetate,Washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, concentrated in vacuo to give diglycerol diacetal product 4.78g, yield 86.28%.

Reference： [1]Current Patent Assignee: TAIYUAN UNIVERSITY OF TECHNOLOGY - CN104628711, 2017, B Location in patent: Paragraph 0060; 0061

27
[ 627-82-7 ]
[ 124-25-4 ]
C₂₀H₄₀O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.4%	With aluminum (III) chloride at 200℃; for 3h; Inert atmosphere;	7 Example 7: In a three-necked round-bottomed flask equipped with an electromagnetic heater, a condenser tube, and a nitrogen inlet tube, diglycerin (8.30 g) was added, and then n-tetradecanal (3.53 g) was added by n-tetradecanal:diglycerin=1:3. According to n-tetradecanal: aluminum chloride = 1:0.006, 0.021 g of aluminum chloride catalyst was added, heated to 200° C. under stirring in a nitrogen atmosphere, cooled to room temperature after 3 hours of reaction, and the resulting reaction solution was washed with water and ethyl acetate. The extract was washed with saturated sodium carbonate solution to remove the catalyst, dried over anhydrous sodium sulfate, concentrated in vacuo, and chromatographed on a column of petroleum ether and ethanol (27:1) to obtain diglycerol monoterequataldehyde with a yield of 76.4%.

Reference： [1]Current Patent Assignee: TAIYUAN UNIVERSITY OF TECHNOLOGY - CN106946840, 2017, A Location in patent: Paragraph 0047; 0048; 0049

28
[ 45842-10-2 ]
[ 112-72-1 ]
[ 124-25-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1-Tetradecanol With tetrabutylammomium bromide; sodium hydrogencarbonate; potassium carbonate In dichloromethane; water at 20℃; Stage #2: With N-chloro-succinimide In dichloromethane; water at 20℃; for 1h;	1 Synthesis of Compound [1] A solution of 100 mL of pure water in which sodium hydrogen carbonate (4.2 g, 50 mmol) and potassium carbonate (0.69 g, 5.0 mmol) were dissolved was added to a solution of 1-tetradecanol (10.7 g, 50 mmol), tetrabutylammonium bromide (TBAB) (0.81 g, 2.5 mmol), and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) (0.39 g, 2.5 mmol) in 100 mL of dichloromethane and the resultant mixture was stirred at room temperature. To this solution, N-chlorosuccinimide (NCS) (8.0 g, 60 mmol) was added and the resultant mixture was stirred at room temperature for 1 hour. After stirring, an organic phase was separated and the organic phase was washed three times with 100 mL of pure water. After washing, the organic phase was separated and sodium sulfate was added to dry the organic phase. Thereafter, sodium sulfate was removed by filtration and the filtrate was concentrated. The residue was purified by column chromatography (silica gel, hexane:ethyl acetate=100:0 to 95:5 (v/v)) to give the target product 1-tetradecanal (Compound [1]): Yield 77% (8.2 g), 1H NMR (400 MHz, CDCl3): δ 9.77 (1H, t, J=1.8 Hz), 2.42 (2H, dt, J=1.8, 7.3 Hz), 1.63 (2H, quintet, J=7.3 Hz), 1.38-1.17 (20H, m), 0.88 (3H, t, J=6.9 Hz).

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION; KYUSHU UNIVERSITY; INSTITUTE OF SYSTEMS - US2018/208618, 2018, A1 Location in patent: Paragraph 0197; 0198; 0199

29
[ 124-25-4 ]
[ 97-30-3 ]
C₂₁H₄₀O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With toluene-4-sulfonic acid; orthoformic acid triethyl ester In hexane; N,N-dimethyl-formamide at 40℃; for 5h;	1 Synthesis of Compound [6] p-Toluenesulfonic acid monohydrate (55 mg, 0.29 mmol) and triethyl orthoformate (1.7 mE, 10 mmol) were added to a suspension solution of methyl a-D-glucopyranoside (1.9 g, 10 mmol) in DMF (5 mE) at room temperature. To the resultant suspension solution, a solution of 1-tetradecanal (Compound [1]) (2.1 g, 10 mmol) in DMF (2.5 mE) and hexane (12 mE) was added at room temperature. The flask containing a reaction solution was connected to a rotary evaporatot The bath temperature of the rotary evaporator was set at 40° C. and the flask was rotated for 5 hours while the pressure of the inside of the system was being reduced to 50 hPa. After 5 hours, the resultant mixture was allowed to cool to room temperature. A saturated aqueous sodium hydrogen carbonate solution was added to the mixture and the obtained precipitate was filtered and washed with water. The residue was purified by column chromatography (silica gel, hexane:ethyl acetate=60:40 to 40:60 (v/v)) to give the target product (Compound [6]):Yield 31% (1.2 g), ‘H NMR (400 MHz, CDC13): 04.78 (1H, d, J=4.1 Hz), 4.54 (1H, t, J=5.0 Hz), 4.12 (1H, dd, J=5.0, 10.1 Hz), 3.85 (1H, t, J=9.2 Hz), 3.68-3.54 (2H, m), 3.50 (1H, t, J=10.3 Hz), 3.43 (3H, s), 3.25 (1H, t, J=9.4 Hz), 2.84 (1H, s), 2.38 (1H, d, J=9.6 Hz), 1.73-1.57 (2H, m), 1.44-1.34 (2H, m), 1.33-1.20 (20H, m), 0.88 (3H, t, J=6.9 Hz).

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION; KYUSHU UNIVERSITY; INSTITUTE OF SYSTEMS - US2018/208618, 2018, A1 Location in patent: Paragraph 0204; 0209; 0210

30
[ 124-25-4 ]
[ 188447-91-8 ]
(S,E)-4-methyl-N-tetradecylidenebenzenesulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With titanium(IV) tetraethanolate In dichloromethane at 55℃; for 6h; Inert atmosphere;	4.2.1. Synthesis of (S,E)-4-methyl-Ntetradecylidenebenzenesulfinamide (12) To a solution of compound 10 (10.0 g, 64.4 mmol) and 11 (17.8 g,83.7 mmol) in anhydrous DCM (500 mL) was added a solution ofTi(OEt)4 (79.0 g, 346 mmol) in anhydrous DCM (100 mL) under Ar.The reaction mixture was heated to 55 C and refluxed for 6 hbefore it was quenched with ice (500 g). The mixture was filteredand the filtrate was extracted with DCM (3 800 mL). The combinedorganic phases were dried over Na2SO4, filtered andconcentrated under reduced pressure to obtain crude product. Thecrude product was purified by silica gel chromatography (1.2%e2.5% EtOAc in petroleum ether) to obtain 12 (17.3 g, 77%) as a pinkoil.

Reference： [1]Sun, Yuanjun; Zhou, Ruifei; Xu, Honglei; Wang, Dehong; Su, Xiuwen; Wang, Chao; Ding, Yahui; Wang, Liang; Chen, Yue [Tetrahedron, 2019, vol. 75, # 12, p. 1808 - 1818]

31
[ 124-25-4 ]
[ 15398-96-6 ]
S-(trifluoromethyl) tetradecanethioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 80℃; for 16h; Irradiation;

Reference： [1]Guo, Rui-Li; Jia, Qiong; Wang, Meng-Yue; Wang, Yong-Qiang; Zhang, Xing-Long; Zhu, Xue-Qing [Organic and Biomolecular Chemistry, 2020, vol. 18, # 30, p. 5918 - 5926]

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Code	Phrase
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[ 124-25-4 ] Synthesis Path-Downstream 1~31

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