Name: 462-18-0|Tridecan-7-one|98%
Brand: Ambeed
SKU: A938903
Price: 6.0 USD
Availability: InStock
Rating: 98 (35 reviews)

1
[ 1749-29-7 ]
[ 462-18-0 ]
7-[2]pyridylmethyl-tridecan-7-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether at -20℃;

Reference： [1]Tilford; Van Campen [Journal of the American Chemical Society, 1954, vol. 76, p. 2431,2435, 2438][Journal of the American Chemical Society, 1957, vol. 79, p. 6575]

2
[ 111-71-7 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	With chromium(III) oxide at 400 - 450℃;
	With methyllithium; calcium carbonate
	Multi-step reaction with 2 steps 1: 79 percent 2: 84 percent / chromic acid

Multi-step reaction with 2 steps 1: magnesium; iodine / diethyl ether / 25 °C / Inert atmosphere 2: sodium dichromate; sulfuric acid / water / 25 °C / Inert atmosphere

Reference： [1]Komarewsky; Coley [Journal of the American Chemical Society, 1941, vol. 63, p. 702,3270] Coley; Komarewsky [Journal of the American Chemical Society, 1946, vol. 68, p. 716]
[2]Fittig [Justus Liebigs Annalen der Chemie, 1861, vol. 117, p. 77]
[3]Schmitz; Sonnenschein; Gruendemann [Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 2, p. 261 - 272]
[4]Chen, Yi-Ru; Zhang, Yong-Yun; Yeh, Ming-Che; Luo, Ying-Ting; Ong, Chi Wi [ChemPlusChem, 2020, vol. 85, # 4, p. 613 - 618]

3
[ 111-70-6 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	With chromium(III) oxide at 400 - 450℃;

Reference： [1]Komarewsky; Coley [Journal of the American Chemical Society, 1941, vol. 63, p. 702,3270] Coley; Komarewsky [Journal of the American Chemical Society, 1946, vol. 68, p. 716]

4
[ 462-18-0 ]
[ 629-50-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; amalgamated zinc

Reference： [1]Vogel [Journal of the Chemical Society, 1946, p. 136][Journal of the Chemical Society, 1948, p. 613]

5
[ 462-18-0 ]
[ 927-45-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
90%	With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃; for 1h;	7.3 ATX-86: Step 3 To a solution of 44 g tridecane-7-one (1 eq) dissolved in MeOH/THF, 1.5 eq. sodium borohydride was added at 0° C. and the resulting solution was stirred at room temperature for 1 hour. Progress of the reaction was monitored by TLC (10% EtOAc in hexane; Rf: 0.5). Reaction mass was quenched with saturated NH4Cl solution (75 ml). Solvent was removed under reduced pressure and the resulting crude was portioned between EtOAc (150 ml) and water (100 ml). Organic layer was separated and the aqueous layer was washed with EtOAc (3×100 ml). Combined organic layers were concentrated under reduced pressure to get white solid. Quantity produced, 40 g; yield, 90%; confirmed by Mass.
90%	With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 1h;	7.3 ATX-0086: Step 3 To a solution of 44 g tridecane-7-one (1 eq) dissolved in MeOH/THF, 1.5 eq. sodium borohydride was added at 0° C. and the resulting solution was stirred at room temperature for 1 hour.Progress of the reaction was monitored by TLC (10% EtOAc in hexane; Rf: 0.5). Reaction mass was quenched with saturated NH4Cl solution (75 ml). Solvent was removed under reduced pressure and the resulting crude was portioned between EtOAc (150 ml) and water (100 ml). Organic layer was separated and the aqueous layer was washed with EtOAc (3×100 ml). Combined organic layers were concentrated under reduced pressure to get white solid. Quantity produced, 40 g; yield, 90%; confirmed by Mass.

88%	With sodium tetrahydroborate In water; isopropyl alcohol for 12h;
43%	With manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; phenylsilane; oxygen In 1,2-dichloro-ethane; isopropyl alcohol at 23℃;
	With kieselguhr; nickel at 120℃; Hydrogenation;
	With kieselguhr; nickel at 90 - 120℃; Hydrogenation;
	With acetic acid; platinum Hydrogenation;
	With sodium hydroxide; diethyl ether; sodium
	With hydrogen at 150℃;
	With lithium aluminium tetrahydride
	With lithium aluminium tetrahydride In diethyl ether

Reference： [1]Bräse, Stefan; Koch, Vanessa [European Journal of Organic Chemistry, 2021, vol. 2021, # 24, p. 3478 - 3483]
[2]Current Patent Assignee: ARCTURUS THERAPEUTICS LTD - US2018/169268, 2018, A1 Location in patent: Paragraph 0024; 0319-0321
[3]Current Patent Assignee: ARCTURUS THERAPEUTICS LTD - US2018/170866, 2018, A1 Location in patent: Paragraph 0361; 0362; 0363
[4]Nagarjuna; Kumar, Abhishek; Kokil, Akshay; Jadhav, Kedar G.; Yurt, Serkan; Kumar, Jayant; Venkataraman [Journal of Materials Chemistry, 2011, vol. 21, # 41, p. 16597 - 16602]
[5]Magnus, Philip; Fielding, Mark R [Tetrahedron Letters, 2001, vol. 42, # 38, p. 6633 - 6636]
[6]Komarewsky; Coley [Journal of the American Chemical Society, 1941, vol. 63, p. 701,3269]
[7]Dreger et al. [Industrial and Engineering Chemistry, 1944, vol. 36, p. 611] Current Patent Assignee: DUPONT DE NEMOURS INC - US2108133, 1936, A
[8]Gastambide [Bulletin de la Societe Chimique de France, 1954, p. 842,848][Annales de Chimie (Cachan, France), 1954, vol. <12>9, p. 263]
[9]Kipping [Journal of the Chemical Society, 1890, vol. 57, p. 537]
[10]Lenne,H.-U. et al. [Justus Liebigs Annalen der Chemie, 1970, vol. 732, p. 70 - 96]
[11]Korablev, L. I.; Pritzkow, W.; Schmidt, U.; Schmidt-Renner, W.; Voerckel, V.; Willecke, L. [Journal fur praktische Chemie (Leipzig 1954), 1984, vol. 326, # 3, p. 502 - 504]
[12]Teodorović, Aleksandar V.; Badjuk, Dalibor M.; Stevanović, Nenad; Pavlović, Radoslav Z. [Journal of Molecular Structure, 2013, vol. 1040, p. 19 - 24]

6
[ 68332-36-5 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	With chromium(III) oxide at 400 - 450℃;

Reference： [1]Komarewsky; Coley [Journal of the American Chemical Society, 1941, vol. 63, p. 702,3270] Coley; Komarewsky [Journal of the American Chemical Society, 1946, vol. 68, p. 716]

7
[ 462-18-0 ]
[ 68-11-1 ]
4,4-dihexyl-3,5-dithia-heptanedioic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water

Reference： [1]Ritter; Lover [Journal of the American Chemical Society, 1952, vol. 74, p. 5576]

8
[ 462-18-0 ]
[ 79-42-5 ]
4,4-dihexyl-2,6-dimethyl-3,5-dithia-heptanedioic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

Reference： [1]Ritter; Lover [Journal of the American Chemical Society, 1952, vol. 74, p. 5576]

9
[ 462-18-0 ]
[ 1674-56-2 ]
7-(2-hydroxy-propylamino)-tridecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; platinum Hydrogenation;

Reference： [1]Cope; Hancock [Journal of the American Chemical Society, 1944, vol. 66, p. 1448,1449, 1451]

10
[ 64-17-5 ]
[ 462-18-0 ]
[ 106-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	With nitrosylchloride In liquid sulphur dioxide

Reference： [1]Rogic,M.M. et al. [Journal of the American Chemical Society, 1975, vol. 97, p. 3848 - 3850]

11
[ 462-18-0 ]
[ 6033-61-0 ]

Yield	Reaction Conditions	Operation in experiment
	With nitrosylchloride In liquid sulphur dioxide

Reference： [1]Rogic,M.M. et al. [Journal of the American Chemical Society, 1975, vol. 97, p. 3848 - 3850]

12
[ 462-18-0 ]
[ 70593-70-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With [bis(acetoxy)iodo]benzene; iron(III) chloride hexahydrate In acetic acid at 20℃; for 18h; Inert atmosphere;
	With sulfuryl dichloride In tetrachloromethane

Reference： [1]Tang, Shi-Zhong; Zhao, Wenshuang; Chen, Tao; Liu, Yang; Zhang, Xiao-Ming; Zhang, Fu-Min [Advanced Synthesis and Catalysis, 2017, vol. 359, # 23, p. 4177 - 4183]
[2]Asinger,F. et al. [Monatshefte fur Chemie, 1979, vol. 110, p. 425 - 435]

13
[ 111-71-7 ]
[ 112-40-3 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; mercury at 60℃; Irradiation;
	With hydrogen; mercury at 40℃; Irradiation;

Reference： [1]Ferguson, Richard R.; Crabtree, Robert H. [Journal of Organic Chemistry, 1991, vol. 56, # 19, p. 5503 - 5510]
[2]Ferguson, Richard R.; Crabtree, Robert H. [Journal of Organic Chemistry, 1991, vol. 56, # 19, p. 5503 - 5510]

14
[ 6486-05-1 ]
[ 462-18-0 ]
[ 72335-32-1 ]

Yield	Reaction Conditions	Operation in experiment
66%	In tetrachloromethane at 20℃; for 24h;

Reference： [1]Clarembeau, M.; Cravador, A.; Dumont, W.; Hevesi, L; Krief, A.; et al. [Tetrahedron, 1985, vol. 41, # 21, p. 4793 - 4812]

15
[ 111-25-1 ]
[ 124-38-9 ]
[ 112-40-3 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 20 % Chromat. 2: 80 % Chromat.	With tetrabutylammomium bromide In various solvent(s) Ambient temperature; electrolysis, -1.6 V;

Reference： [1]Garnier, L.; Rollin, Y.; Perichon, J. [Journal of Organometallic Chemistry, 1989, vol. 367, p. 347 - 358]

16
[ 927-45-7 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-chloro-succinimide; N-(phenylthio)-N-(tert-butyl)amine; potassium carbonate In dichloromethane at 20℃; for 1h;
98%	With bromine; potassium carbonate; N-tert-butyl-2-nitrobenzenesulfenamide In dichloromethane at 20℃; for 0.833333h;
85%	With sodium dichromate; sulfuric acid In water at 25℃; Inert atmosphere;

84%

With chromic acid

Reference： [1]Matsuo, Jun-Ichi; Iida, Daisuke; Yamanaka, Hiroyuki; Mukaiyama, Teruaki [Tetrahedron, 2003, vol. 59, # 35, p. 6739 - 6750]
[2]Matsuo, Jun-Ichi; Kawana, Asahi; Yamanaka, Hiroyuki; Mukaiyama, Teruaki [Chemistry Letters, 2003, vol. 32, # 2, p. 182 - 183]
[3]Chen, Yi-Ru; Zhang, Yong-Yun; Yeh, Ming-Che; Luo, Ying-Ting; Ong, Chi Wi [ChemPlusChem, 2020, vol. 85, # 4, p. 613 - 618]
[4]Schmitz; Sonnenschein; Gruendemann [Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 2, p. 261 - 272]

17
[ 462-18-0 ]
[ 131-11-3 ]
[ 97920-50-8 ]

Yield	Reaction Conditions	Operation in experiment
22%	With sodium hydride In benzene for 15h; Heating;

Reference： [1]Murthy, A. R.; Wyrick, S. D.; Hall, I. H. [Journal of Medicinal Chemistry, 1985, vol. 28, # 11, p. 1591 - 1596]

18
[ 462-18-0 ]
[ 22513-16-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With ammonium acetate; sodium cyanotrihydridoborate In methanol at 20℃; for 90h;
97%	With ammonium acetate; sodium cyanotrihydridoborate In methanol at 20℃; for 48h;
95%	With sodium tetrahydridoborate; ammonium acetate In methanol at 30℃; for 24h;

95.37%	With ammonium acetate; sodium cyanotrihydridoborate In methanol at 20℃; for 60h; Inert atmosphere;	1.1 1. Synthesis of compound a Ar protection, add 7-tridecone (3967.6mg, 20mmol, 1eq), NH4OAc (15417.0mg, 200mmol, 10eq), NaBH3CN (1234.8mg, 10mmol, 1eq) to a 100mL double-necked flask, ventilate, add methanol (60mL), start the reaction at room temperature for 60h, take a sample, TLC (PE/EA=1/1, v/v), then put it into an iodine cylinder, there is product formation, TLC (PE), put in phenylhydrazine for color development, no raw materials, stop the reaction, transfer to the original bottom flask, add 4 mL of concentrated hydrochloric acid, spin dry methanol, add water, adjust the pH to 10 with 5% NaOH, extract 4 times with dichloromethane, spin dry the organic layer to obtain compound 3984.6 mg with a yield of 95.37 %.
92%	With ammonium acetate; sodium cyanotrihydridoborate In methanol at 20℃; for 56h;
90%	With ammonium acetate; sodium cyanotrihydridoborate In methanol at 20℃; for 48h;
90%	With ammonium acetate; sodium cyanotrihydridoborate In methanol at 20℃; for 56h;
82.3%	With ammonium acetate; sodium cyanotrihydridoborate In methanol at 20℃; for 56h;
81%	Stage #1: di-n-hexyl ketone With ammonium acetate; sodium tris(acetoxy)borohydride In methanol at 20℃; for 48h; Stage #2: With hydrogenchloride; methanol; lithium hydroxide monohydrate Stage #3: With potassium hydroxide; lithium hydroxide monohydrate	1 Preparation of 1 -hexylheptylamine 1[0076] In a 25O mL round bottom flask, 5.00 g (25.5 mmol) dihexylketone, 19.7 g (255 mmol) ammonium acetate, and 1.10 g (17.8 mmol) sodium cyanoborohydride (NaBH3CN) were dissolved in 75 mL absolute MeOH and stirred at room temperature for 48 hours, until no significant amount of the starting material could be detected by NMR. The mixture was quenched by adding concentrated hydrochloric acid (HCl) dropwise (~3 mL), then concentrated in vacuo. The resulting white solid was taken up in 500 mL water, basified to pH 10 with solid potassium hydroxide (KOH), and extracted with chloroform (CHCl3) twice (200 mL each). The CHCl3 fractions were combined and concentrated to give 4.12 g (81%) of 1 -hexylheptylamine 1 as a pale yellow oil. 1H NMR (D2O, 500 MHz): δ 0.73 (t, 6H), 1.15-1.23 (m, 16H), 1.55 (m, 4H), 3.13 (m, IH).
70%	With ammonia; hydrogen In methanol at 100℃; for 36h;
63%	Stage #1: di-n-hexyl ketone With ammonium acetate In methanol for 0.5h; Inert atmosphere; Stage #2: With sodium cyanotrihydridoborate In methanol at 20℃; for 48h;
	With ammonium acetate; sodium cyanotrihydridoborate In methanol at 20℃; for 60h;
	With ammonium acetate; sodium cyanotrihydridoborate
	Stage #1: di-n-hexyl ketone With ammonium acetate; sodium cyanotrihydridoborate In methanol at 30℃; for 12h; Stage #2: With hydrogenchloride In methanol; lithium hydroxide monohydrate
	With ammonium acetate; sodium cyanotrihydridoborate
	Multi-step reaction with 2 steps 1: hydroxylamine; sodium hydroxide / ethanol; lithium hydroxide monohydrate 2: lithium aluminium hydride / tetrahydrofuran

Reference： [1]Grimme, Stefan; Höger, Sigurd; Jester, Stefan-S.; Jochemich, Anna; Keller, Tristan J.; Krönert, Anna; Müller, Ute; Poluektov, Georgiy; Spicher, Sebastian [Angewandte Chemie - International Edition, 2021, vol. 60, # 52, p. 27264 - 27270][Angew. Chem., 2021, vol. 133, # 52, p. 27470 - 27476]
[2]Davis, Nathaniel J.L.K.; Macqueen, Rowan W.; Roberts, Derrick A.; Danos, Andrew; Dehn, Sabrina; Perrier, Sébastien; Schmidt, Timothy W. [Journal of Materials Chemistry C, 2016, vol. 4, # 35, p. 8270 - 8275]
[3]Myahkostupov, Mykhaylo; Castellano, Felix N. [Tetrahedron, 2015, vol. 71, # 51, p. 9519 - 9527]
[4]Current Patent Assignee: UNIV SUN YAT SEN - CN114369103, 2022, A Location in patent: Paragraph 0045-0049
[5]Che, Yanke; Datar, Aniket; Balakrishnan, Kaushik; Zang, Ling [Journal of the American Chemical Society, 2007, vol. 129, # 23, p. 7234 - 7235]
[6]Holman, Michael W.; Liu, Ruchuan; Adams, David M. [Journal of the American Chemical Society, 2003, vol. 125, # 41, p. 12649 - 12654]
[7]Huang, Yongwei; Hu, Jianchen; Kuang, Wenfeng; Wei, Zhixiang; Faul, Charl F. J. [Chemical Communications, 2011, vol. 47, # 19, p. 5554 - 5556]
[8]Cao, Pengpeng; Khorev, Oleg; Devaux, André; Sägesser, Lucie; Kunzmann, Andreas; Ecker, Achim; Häner, Robert; Brühwiler, Dominik; Calzaferri, Gion; Belser, Peter [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4046 - 4060]
[9]Current Patent Assignee: FLEXTERRA INC - WO2008/51552, 2008, A2 Location in patent: Page/Page column 26
[10]Schmitz; Sonnenschein; Gruendemann [Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 2, p. 261 - 272]
[11]Location in patent: experimental part Manning, Steven J.; Bogen, William; Kelly, Lisa A. [Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6007 - 6013]
[12]Myahkostupov, Mykhaylo; Prusakova, Valentina; Oblinsky, Daniel G.; Scholes, Gregory D.; Castellano, Felix N. [Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8634 - 8644]
[13]Ito, Syoji; Taga, Yuhei; Hiratsuka, Kengo; Takei, Satoshi; Kitagawa, Daichi; Kobatake, Seiya; Miyasaka, Hiroshi [Chemical Communications, 2015, vol. 51, # 72, p. 13756 - 13759]
[14]Sao, Soumik; Mukherjee, Ishita; De, Priyadarsi; Chaudhuri, Debangshu [Chemical Communications, 2017, vol. 53, # 28, p. 3994 - 3997]
[15]Eserci, Hande; Şenkuytu, Elif; Okutan, Elif [Journal of Molecular Structure, 2019, vol. 1182, p. 1 - 8]
[16]Chen, Huaqing; Wang, Ling; Sun, Hua; Liu, Qian; Tan, Xiao; Sang, Shenglong; Wu, Bo; Zhang, Cong; Chen, Fei; Hang, Xiao-Chun; Chen, Zhi-Kuan [New Journal of Chemistry, 2020, vol. 44, # 30, p. 13093 - 13099]

19
[ 462-18-0 ]
[ 1119-06-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis-trimethylsilanyl peroxide; tin(IV) chloride In dichloromethane at 25℃; for 5h;

Reference： [1]Matsubara; Takai; Nozaki [Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 7, p. 2029 - 2032]

20
[ 462-18-0 ]
[ 97584-62-8 ]

Yield	Reaction Conditions	Operation in experiment
16%	With hydrogen sulfide; zinc(II) chloride; trimethyl orthoformate In methanol at 5℃; for 1h;

Reference： [1]Metzner, Patrick; Rakotonirina, Rose [Tetrahedron, 1985, vol. 41, # 7, p. 1289 - 1298]

21
[ 462-18-0 ]
[ 100-97-0 ]
[ 103086-96-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With acetic acid In ethanol for 168h; Heating;
70.1%	With acetic acid In butan-1-ol Heating;
	With acetic acid In ethanol for 15h; Reflux;

Reference： [1]Levinger, Shlomo; Sharabi-Ronen, Yifat; Mainfeld, Alexander; Albeck, Amnon [Journal of Organic Chemistry, 2008, vol. 73, # 19, p. 7793 - 7796]
[2]Kuznetsov, A. I.; Basargin, E. B.; Moskovkin, A. S.; Ba, M. Kh.; Miroshnichenko, I. V.; et al. [Chemistry of Heterocyclic Compounds, 1985, vol. 21, # 12, p. 1382 - 1388][Khimiya Geterotsiklicheskikh Soedinenii, 1985, vol. 21, # 12, p. 1679 - 1685]
[3]Sharabi-Ronen, Yifat; Levinger, Shlomo; Lellouche, Miri Ben-Dahan; Albeck, Amnon [Medicinal Chemistry, 2014, vol. 10, # 1, p. 27 - 37]

22
[ 462-18-0 ]
[ 645-96-5 ]
[ 61539-71-7 ]

Yield	Reaction Conditions	Operation in experiment
16%	In tetrachloromethane at 20℃; for 4h;

Reference： [1]Clarembeau, M.; Cravador, A.; Dumont, W.; Hevesi, L; Krief, A.; et al. [Tetrahedron, 1985, vol. 41, # 21, p. 4793 - 4812]

23
[ 136843-73-7 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
50 % Chromat.	With triethyl borane; triphenylstannane In hexane; benzene at 25℃; for 12h;

Reference： [1]Nozaki, Kyoko; Oshima, Koichiro; Utimoto, Kiitiro [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 8, p. 2585 - 2587]

24
[ 13487-95-1 ]
[ 74010-58-5 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	In dichloromethane -70 deg C, then 20 deg C, 8 h;
79%	In dichloromethane added at -70 deg C, then 7-13 h at room temperature;

Reference： [1]Tolstikov, G. A.; Valitov, F. Kh.; Kuchin, A. V. [Journal of general chemistry of the USSR, 1981, vol. 51, # 7, p. 1434][Zhurnal Obshchei Khimii, 1981, vol. 51, # 7, p. 1682]
[2]Tolstikov, G. A.; Valitov, F. Kh.; Kuchin, A. V. [Journal of general chemistry of the USSR, 1982, vol. 52, # 6, p. 1170 - 1175][Zhurnal Obshchei Khimii, 1982, vol. 52, # 6, p. 1328 - 1334]

25
[ 462-18-0 ]
[ 62217-35-0 ]
[ 110166-40-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With n-butyllithium In tetrahydrofuran at -78℃;

Reference： [1]Ceruti, Maurizio; Degani, Iacopo; Fochi, Rita [Synthesis, 1987, # 1, p. 79 - 82]

26
[ 95110-71-7 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium phenylselenide In ethanol for 0.0833333h; Ambient temperature;
89%	With sodium phenylselenide In ethanol for 0.0833333h; Ambient temperature;

Reference： [1]Satoh, Tsuyoshi; Kaneko, Youhei; Kumagawa, Takumi; Izawa, Takao; Sakata, Kiichi; Yamakawa, Koji [Chemistry Letters, 1984, p. 1957 - 1960]
[2]Satoh, Tsuyoshi; Kaneko, Youhei; Izawa, Takao; Sakata, Kiichi; Yamakawa, Koji [Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 7, p. 1983 - 1990]

27
[ 462-18-0 ]
[ 96-24-2 ]
2,2-dihexyl-4-chloromethyl-1,3-dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With toluene-4-sulfonic acid In toluene Heating;

Reference： [1]Wilk, Kazimiera A.; Bieniecki, Albert; Burczyk, Bogdan; Sokolowski, Adam [Journal of the American Oil Chemists' Society, 1994, vol. 71, # 1, p. 81 - 85]

28
7-(phenyldimethylsilyl)-7-tridecanol [ No CAS ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With jones reagent In diethyl ether

Reference： [1]Rosario, Osvaldo; Sandoval, Sydia; Larson, Gerald L. [Synthetic Communications, 1980, vol. 10, # 11, p. 813 - 820]

29
[ 462-18-0 ]
[ 154-23-4 ]
catechin 7-tridecanone ketal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In tetrahydrofuran at 0℃; 10 min then 10 min;

Reference： [1]Laks, Peter E.; Pruner, Marcia S. [Phytochemistry, 1989, vol. 28, # 1, p. 87 - 92]

30
methoxyethoxymethyl ether of 4-hexyl-1-decen-4-ol [ No CAS ]
[ 462-18-0 ]
4-Chloro-2,2-dihexyl-tetrahydro-pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 15%	With titanium tetrachloride In dichloromethane at -78℃; for 0.5h;

Reference： [1]Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro [Tetrahedron Letters, 1994, vol. 35, # 43, p. 7977 - 7980]

31
methoxymethyl ether of (E)-4-hexyl-1-trimethylsilyl-1-decen-4-ol [ No CAS ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With titanium tetrachloride In dichloromethane at -78℃; for 0.5h;

Reference： [1]Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro [Tetrahedron Letters, 1994, vol. 35, # 43, p. 7977 - 7980]

32
Triethyl-{(E)-3-[1-hexyl-1-(2-methoxy-ethoxymethoxy)-heptyl]-dodec-1-enyl}-silane [ No CAS ]
[ 462-18-0 ]
2,2-Dihexyl-3-nonyl-3,6-dihydro-2H-pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With titanium tetrachloride In dichloromethane at -78℃; for 0.5h; Yields of byproduct given;

Reference： [1]Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro [Tetrahedron Letters, 1994, vol. 35, # 43, p. 7977 - 7980]

33
[ 160036-78-2 ]
[ 462-18-0 ]
6,6-dihexyl-5,6-dihydro-2H-pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 81% 2: 12%	With titanium tetrachloride In dichloromethane at -78℃; for 0.5h;

Reference： [1]Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro [Tetrahedron Letters, 1994, vol. 35, # 43, p. 7977 - 7980]

34
[ 160036-79-3 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tin(IV) chloride In dichloromethane at -78℃;
92%	With titanium tetrachloride In dichloromethane at -78℃; further Lewis acids;

Reference： [1]Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro [Tetrahedron Letters, 1994, vol. 35, # 43, p. 7977 - 7980]
[2]Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro [Tetrahedron Letters, 1994, vol. 35, # 43, p. 7977 - 7980]

35
[ 111-25-1 ]
[ 201230-82-2 ]
[ 112-40-3 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 30 % Chromat. 2: 60%	With 1-methyl-pyrrolidin-2-one; [2,2]bipyridinyl; tetrabutylammonium tetrafluoroborate; iron(II) chloride Ambient temperature; electrolysis;

Reference： [1]Ocafrain, Maitena; Devaud, Marguerite; Troupel, Michel; Perichon, Jacques [Journal of the Chemical Society. Chemical communications, 1995, # 22, p. 2331 - 2332]

36
[ 462-18-0 ]
[ 4009-98-7 ]
2-hexyl-1-methoxy-1-octene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 1 h; Multistep reaction;
	Stage #1: (methoxymethyl)triphenylphosphonium chloride With n-butyllithium In diethyl ether; hexane at 0 - 20℃; Stage #2: tridecan-7-one In diethyl ether; hexane at 0 - 20℃;

Reference： [1]Kato, Masaya; Komoda, Keiko; Namera, Akira; Sarai, Yusuke; Okada, Satoshi; Yamada, Akira; Yokoyama, Kouichi; Migita, Emiko; Minobe, Yasushi; Tani, Tadato [Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 11, p. 1767 - 1776]
[2]Location in patent: experimental part Cohen, Yael; Bodner, Efrat; Richman, Michal; Afri, Michal; Frimer, Aryeh A. [Chemistry and Physics of Lipids, 2008, vol. 155, # 2, p. 98 - 113]

37
[ 592-41-6 ]
[ 5396-91-8 ]
[ 462-18-0 ]
[ 56741-23-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 32% 2: 19%	With 3-methylpyridin-2-ylamine; Wilkinson's catalyst at 150℃; for 48h;

Reference： [1]Jun, Chul-Ho; Lee, Hyuk [Journal of the American Chemical Society, 1999, vol. 121, # 4, p. 880 - 881]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide

39
[ 638-45-9 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis;
32%	With iron pentacarbonyl In N,N,N,N,N,N-hexamethylphosphoric triamide; benzene at 80℃; for 3h;

Reference： [1]Dolhem; Ocafrain; Nedelec; Troupel [Tetrahedron, 1997, vol. 53, # 50, p. 17089 - 17096]
[2]Vasil'Eva; Mysova; Chakhovskaya; Terent'Ev [Russian Journal of Organic Chemistry, 2002, vol. 38, # 7, p. 1014 - 1017]

40
[ 18431-36-2 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium iodide In N,N-dimethyl-formamide at 80℃; for 20h;

Reference： [1]Ryu, Ilhyong; Ryang, Membo; Rhee, Ilsong; Omura, Haruo; Murai, Shinji; Sonoda, Noboru [Synthetic Communications, 1984, vol. 14, # 12, p. 1175 - 1180]

41
[ 592-41-6 ]
[ 329971-04-2 ]
[ 462-18-0 ]
(E)-Tetradec-12-en-7-one [ No CAS ]
[ 329971-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tricyclohexylphosphine In toluene at 150℃; for 6h;

Reference： [1]Jun; Lee; Lim [Journal of the American Chemical Society, 2001, vol. 123, # 4, p. 751 - 752]

42
[ 627-31-6 ]
dihexyl-methanediyl bis-hydroperoxide [ No CAS ]
[ 462-18-0 ]
3,3-dihexyl-[1,2,4,5]tetroxocane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With silver(l) oxide In ethyl acetate

Reference： [1]Kim; Nagai; Ono; Begum; Wataya; Hamada; Tsuchiya; Masuyama; Nojima; McCullough [Journal of Medicinal Chemistry, 2001, vol. 44, # 14, p. 2357 - 2361]

43
[ 462-18-0 ]
dihexyl-methanediyl bis-hydroperoxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With formic acid at 20℃; for 0.05h;

Reference： [1]Kim; Nagai; Ono; Begum; Wataya; Hamada; Tsuchiya; Masuyama; Nojima; McCullough [Journal of Medicinal Chemistry, 2001, vol. 44, # 14, p. 2357 - 2361]

44
[ 462-18-0 ]
[ 1068-57-1 ]
[ 419562-23-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium sulfate at 20℃; for 20h;

Reference： [1]Hashmi, A. Stephen K.; Grundl, Marc A.; Nass, Andreas Rivas; Naumann, Frank; Bats, Jan W.; Bolte, Michael [European Journal of Organic Chemistry, 2001, # 24, p. 4705 - 4732]

45
[ 592-41-6 ]
[ 42052-30-2 ]
[ 462-18-0 ]
pentadecane-2,9-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 11%	With 3-methylpyridin-2-ylamine; cyclohexylamine; benzoic acid In toluene at 130℃; for 1h;

Reference： [1]Jun, Chul-Ho; Moon, Choong Woon; Lim, Sung-Gon; Lee, Hyuk [Organic Letters, 2002, vol. 4, # 9, p. 1595 - 1597]

46
[ 592-41-6 ]
[ 6221-51-8 ]
[ 462-18-0 ]
octadecane-2,12-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-methylpyridin-2-ylamine; cyclohexylamine; benzoic acid In toluene at 130℃; for 1h;

Reference： [1]Jun, Chul-Ho; Moon, Choong Woon; Lim, Sung-Gon; Lee, Hyuk [Organic Letters, 2002, vol. 4, # 9, p. 1595 - 1597]

47
[ 592-41-6 ]
[ 10035-97-9 ]
[ 462-18-0 ]
hexadecane-2,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-methylpyridin-2-ylamine; cyclohexylamine; benzoic acid In toluene at 130℃; for 1h;

Reference： [1]Jun, Chul-Ho; Moon, Choong Woon; Lim, Sung-Gon; Lee, Hyuk [Organic Letters, 2002, vol. 4, # 9, p. 1595 - 1597]

48
[ 592-41-6 ]
[ 56345-02-9 ]
[ 462-18-0 ]
heneicosane-2,15-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-methylpyridin-2-ylamine; cyclohexylamine; benzoic acid In toluene at 130℃; for 1h;

Reference： [1]Jun, Chul-Ho; Moon, Choong Woon; Lim, Sung-Gon; Lee, Hyuk [Organic Letters, 2002, vol. 4, # 9, p. 1595 - 1597]

49
[ 592-41-6 ]
[ 24593-67-7 ]
[ 462-18-0 ]
heptadecane-2,11-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-methylpyridin-2-ylamine; cyclohexylamine; benzoic acid In toluene at 130℃; for 1h;

Reference： [1]Jun, Chul-Ho; Moon, Choong Woon; Lim, Sung-Gon; Lee, Hyuk [Organic Letters, 2002, vol. 4, # 9, p. 1595 - 1597]

50
[ 592-42-7 ]
[ 256379-28-9 ]
[ 462-18-0 ]
[ 56741-23-2 ]
[ 583-60-8 ]
[ 502-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,5-Hexadien; N-(3-methyl-2-pyridyl)-N-[(E)-3-phenyl-2-propenyl]amine With {(C₈H₁₄)2RhCl₂}2; tricyclohexylphosphine In toluene at 150℃; for 2h; Stage #2: With hydrogen Further byproducts given;

Reference： [1]Lee, Dae-Yon; Kim, In-Jung; Jun, Chul-Ho [Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 3031 - 3033]

51
[ 462-18-0 ]
[ 1535-65-5 ]
7-(benzenesulfonyl-difluoro-methyl)-tridecan-7-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.5h;

Reference： [1]Prakash, G.K.Surya; Hu, Jinbo; Wang, Ying; Olah, George A. [European Journal of Organic Chemistry, 2005, # 11, p. 2218 - 2223]

52
[ 462-18-0 ]
[ 4045-44-7 ]
[ 874964-07-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: 1,2,3,4,5-pentamethylcyclopentadiene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Stage #2: tridecan-7-one With dimethylaluminum chloride In tetrahydrofuran; hexane at -20℃; for 1h;

Reference： [1]Uemura, Minoru; Yorimitsu, Hideki; Oshima, Koichiro [Tetrahedron Letters, 2006, vol. 47, # 2, p. 163 - 166]

53
[ 874964-07-5 ]
[ 462-18-0 ]
[ 4045-44-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 98% 2: 100%	In toluene for 30h; Heating;

Reference： [1]Uemura, Minoru; Yagi, Kazunari; Iwasaki, Masayuki; Nomura, Kenichi; Yorimitsu, Hideki; Oshima, Koichiro [Tetrahedron, 2006, vol. 62, # 15, p. 3523 - 3535]

54
[ 462-18-0 ]
lithiumpentamethylcyclopentadiene [ No CAS ]
[ 874964-07-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dimethylaluminum chloride In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Uemura, Minoru; Yagi, Kazunari; Iwasaki, Masayuki; Nomura, Kenichi; Yorimitsu, Hideki; Oshima, Koichiro [Tetrahedron, 2006, vol. 62, # 15, p. 3523 - 3535]

55
7,7-bis-dodecylsulfanyl-tridecane [ No CAS ]
[ 109-87-5 ]
[ 31336-25-1 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 88% 2: 85%	With oxalic acid In nitromethane at 60℃; for 10h;

Reference： [1]Miyake, Hideyoshi; Nakao, Yuichi; Sasaki, Mitsuru [Tetrahedron Letters, 2006, vol. 47, # 35, p. 6247 - 6250]

56
[ 211691-09-7 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen

Reference： [1]Jun; Lee; Lim [Journal of the American Chemical Society, 2001, vol. 123, # 4, p. 751 - 752]

57
[ 462-18-0 ]
[ 154-23-4 ]
(6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-dihexyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 6524 - 6525

58
[ 462-18-0 ]
[ 120-80-9 ]
[ 7527-54-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	In benzene Reflux; Inert atmosphere;
68%	With toluene-4-sulfonic acid In toluene Heating;

Reference： [1]Chen, Yi-Ru; Zhang, Yong-Yun; Yeh, Ming-Che; Luo, Ying-Ting; Ong, Chi Wi [ChemPlusChem, 2020, vol. 85, # 4, p. 613 - 618]
[2]McKeown, Neil B.; Helliwell, Madeleine; Hassan, Bashir M.; Hayhurst, David; Li, Hong; Thompson, Neil; Teat, Simon J. [Chemistry - A European Journal, 2007, vol. 13, # 1, p. 228 - 234]

59
[ 592-41-6 ]
[ 256379-28-9 ]
[ 462-18-0 ]
[ 56741-23-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 91% 2: 3%	Stage #1: 1-hexene; N-(3-methyl-2-pyridyl)-N-[(E)-3-phenyl-2-propenyl]amine With tricyclohexylphosphine at 170℃; for 0.5h; Stage #2: With hydrogenchloride Further stages.;

Reference： [1]Jun, Chul-Ho; Lee, Hyuk; Park, Jae-Bum; Lee, Dae-Yon [Organic Letters, 1999, vol. 1, # 13, p. 2161 - 2164]

60
[ 462-18-0 ]
[ 110590-84-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 90 percent / NH₄OAc; NaBH₃CN / methanol / 48 h / 20 °C 2: imidazole / 5 h / 180 °C
	Multi-step reaction with 2 steps 1: ammonium acetate; sodium cyanotrihydridoborate / methanol / 56 h / 20 °C 2: 1H-imidazole / 3 h / 130 °C
	Multi-step reaction with 2 steps 1: ammonium acetate; sodium cyanotrihydridoborate / methanol / 60 h / 20 °C 2: 1H-imidazole / 4 h / 160 °C

	Multi-step reaction with 2 steps 1: ammonium acetate; sodium tetrahydridoborate / methanol / 24 h / 30 °C 2: 1H-imidazole / 4 h / 140 °C
	Multi-step reaction with 2 steps 1: ammonium acetate; sodium cyanotrihydridoborate / methanol / 56 h / 20 °C 2: 1H-imidazole; Zinc acetate / 4 h / 190 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sodium cyanotrihydridoborate; ammonium acetate / methanol / 48 h / 20 °C 2: 1H-imidazole / 5 h / 180 °C
	Multi-step reaction with 3 steps 1: hydroxylamine; sodium hydroxide / ethanol; lithium hydroxide monohydrate 2: lithium aluminium hydride / tetrahydrofuran 3: 1H-imidazole / 150 °C
	Multi-step reaction with 2 steps 1: ammonium acetate; sodium cyanotrihydridoborate / methanol / 90 h / 20 °C 2: 1H-imidazole / 5 h / 180 °C
	Multi-step reaction with 2 steps 1: ammonium acetate; sodium cyanotrihydridoborate / methanol / 60 h / 20 °C / Inert atmosphere 2: 1H-imidazole / 4 h / 180 °C / Inert atmosphere

Reference： [1]Holman, Michael W.; Liu, Ruchuan; Adams, David M. [Journal of the American Chemical Society, 2003, vol. 125, # 41, p. 12649 - 12654]
[2]Huang, Yongwei; Hu, Jianchen; Kuang, Wenfeng; Wei, Zhixiang; Faul, Charl F. J. [Chemical Communications, 2011, vol. 47, # 19, p. 5554 - 5556]
[3]Myahkostupov, Mykhaylo; Prusakova, Valentina; Oblinsky, Daniel G.; Scholes, Gregory D.; Castellano, Felix N. [Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8634 - 8644]
[4]Myahkostupov, Mykhaylo; Castellano, Felix N. [Tetrahedron, 2015, vol. 71, # 51, p. 9519 - 9527]
[5]Cao, Pengpeng; Khorev, Oleg; Devaux, André; Sägesser, Lucie; Kunzmann, Andreas; Ecker, Achim; Häner, Robert; Brühwiler, Dominik; Calzaferri, Gion; Belser, Peter [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4046 - 4060]
[6]Davis, Nathaniel J.L.K.; Macqueen, Rowan W.; Roberts, Derrick A.; Danos, Andrew; Dehn, Sabrina; Perrier, Sébastien; Schmidt, Timothy W. [Journal of Materials Chemistry C, 2016, vol. 4, # 35, p. 8270 - 8275]
[7]Chen, Huaqing; Wang, Ling; Sun, Hua; Liu, Qian; Tan, Xiao; Sang, Shenglong; Wu, Bo; Zhang, Cong; Chen, Fei; Hang, Xiao-Chun; Chen, Zhi-Kuan [New Journal of Chemistry, 2020, vol. 44, # 30, p. 13093 - 13099]
[8]Grimme, Stefan; Höger, Sigurd; Jester, Stefan-S.; Jochemich, Anna; Keller, Tristan J.; Krönert, Anna; Müller, Ute; Poluektov, Georgiy; Spicher, Sebastian [Angewandte Chemie - International Edition, 2021, vol. 60, # 52, p. 27264 - 27270][Angew. Chem., 2021, vol. 133, # 52, p. 27470 - 27476]
[9]Current Patent Assignee: UNIV SUN YAT SEN - CN114369103, 2022, A

61
[ 1502-06-3 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: o-iodoxybenzoic acid / toluene; dimethylsulfoxide / 65 °C 2: 2-amino-3-picoline; cyclohexylamine; benzoic acid / chlorotris(triphenylphosphine)rhodium / toluene / 1 h / 130 °C

Reference： [1]Jun, Chul-Ho; Moon, Choong Woon; Lim, Sung-Gon; Lee, Hyuk [Organic Letters, 2002, vol. 4, # 9, p. 1595 - 1597]

62
[ 502-72-7 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; toluene / 65 °C 2: 2-amino-3-picoline; cyclohexylamine; benzoic acid / chlorotris(triphenylphosphine)rhodium / toluene / 1 h / 130 °C

Reference： [1]Jun, Chul-Ho; Moon, Choong Woon; Lim, Sung-Gon; Lee, Hyuk [Organic Letters, 2002, vol. 4, # 9, p. 1595 - 1597]

63
[ 830-13-7 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: o-iodoxybenzoic acid / toluene; dimethylsulfoxide / 65 °C 2: 2-amino-3-picoline; cyclohexylamine; benzoic acid / chlorotris(triphenylphosphine)rhodium / toluene / 1 h / 130 °C

Reference： [1]Jun, Chul-Ho; Moon, Choong Woon; Lim, Sung-Gon; Lee, Hyuk [Organic Letters, 2002, vol. 4, # 9, p. 1595 - 1597]

64
[ 462-18-0 ]
[ 199989-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) potassium tert-butoxide / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 1 h 2: 99.1 g / HCl / tetrahydrofuran; dioxane 3: 17.4 g / borane-THF complex / tetrahydrofuran
	Multi-step reaction with 6 steps 1: 1.) potassium tert-butoxide / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 1 h 2: 99.1 g / HCl / tetrahydrofuran; dioxane 3: 4.85 g / NaBH₄ / methanol 4: 4.34 g / CBr₄, Ph₃P / tetrahydrofuran / 0.5 h / Ambient temperature 5: 490 mg / NaH / dimethylformamide / 24 h / Ambient temperature 6: 272 mg / H₂ / 10percent Pd/C / ethanol

Reference： [1]Kato, Masaya; Komoda, Keiko; Namera, Akira; Sarai, Yusuke; Okada, Satoshi; Yamada, Akira; Yokoyama, Kouichi; Migita, Emiko; Minobe, Yasushi; Tani, Tadato [Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 11, p. 1767 - 1776]
[2]Kato, Masaya; Komoda, Keiko; Namera, Akira; Sarai, Yusuke; Okada, Satoshi; Yamada, Akira; Yokoyama, Kouichi; Migita, Emiko; Minobe, Yasushi; Tani, Tadato [Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 11, p. 1767 - 1776]

65
[ 462-18-0 ]
Sodium; 4-{5-ethyl-4-[3-(2-hexyl-octylamino)-benzoyl]-1-methyl-1H-pyrrol-2-yl}-butyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) potassium tert-butoxide / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 1 h 2: 99.1 g / HCl / tetrahydrofuran; dioxane 3: 17.4 g / borane-THF complex / tetrahydrofuran 4: 95 percent / 1 N NaOH / ethanol
	Multi-step reaction with 7 steps 1: 1.) potassium tert-butoxide / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 1 h 2: 99.1 g / HCl / tetrahydrofuran; dioxane 3: 4.85 g / NaBH₄ / methanol 4: 4.34 g / CBr₄, Ph₃P / tetrahydrofuran / 0.5 h / Ambient temperature 5: 490 mg / NaH / dimethylformamide / 24 h / Ambient temperature 6: 272 mg / H₂ / 10percent Pd/C / ethanol 7: 95 percent / 1 N NaOH / ethanol

Reference： [1]Kato, Masaya; Komoda, Keiko; Namera, Akira; Sarai, Yusuke; Okada, Satoshi; Yamada, Akira; Yokoyama, Kouichi; Migita, Emiko; Minobe, Yasushi; Tani, Tadato [Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 11, p. 1767 - 1776]
[2]Kato, Masaya; Komoda, Keiko; Namera, Akira; Sarai, Yusuke; Okada, Satoshi; Yamada, Akira; Yokoyama, Kouichi; Migita, Emiko; Minobe, Yasushi; Tani, Tadato [Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 11, p. 1767 - 1776]

66
2-hexyl-1,2-epoxyoctane [ No CAS ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Me₃Ga 2: H₂ / Pd/BaSO₄ 3: i-Pr₂NEt 4: 12 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

Reference： [1]Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro [Tetrahedron Letters, 1994, vol. 35, # 43, p. 7977 - 7980]

67
7-(3-Trimethylsilanyl-prop-2-ynyl)-tridecan-7-ol [ No CAS ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂ / Pd/BaSO₄ 2: i-Pr₂NEt 3: 12 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

Reference： [1]Horiuchi, Yoshihiro; Taniguchi, Masahiko; Oshima, Koichiro; Utimoto, Kiitiro [Tetrahedron Letters, 1994, vol. 35, # 43, p. 7977 - 7980]

68
[ 462-18-0 ]
[ 80256-57-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Zn / benzene / 1.5 h / Heating 2: 1.) formic acide, 2.) H₂ / 2.) 5 percent Pd/C / 1.) 1 h, reflux ; 2.) methanol, rt

Reference： [1]Malthete, Jacques; Canceill, Josette; Gabard, Jacqueline; Jacques, Jean [Tetrahedron, 1981, vol. 37, # 16, p. 2823 - 2828]

69
[ 462-18-0 ]
[ 51655-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Zn / benzene / 1.5 h / Heating 2: 1.) formic acide, 2.) H₂ / 2.) 5 percent Pd/C / 1.) 1 h, reflux; 2.) methanol, rt 3: LiAlH₄ / diethyl ether / 2 h / Heating
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.83 h / 20 °C 1.2: 0 °C / Reflux 2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 20 °C
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C 1.2: 0 °C / Reflux 2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 20 °C

Reference： [1]Malthete, Jacques; Canceill, Josette; Gabard, Jacqueline; Jacques, Jean [Tetrahedron, 1981, vol. 37, # 16, p. 2823 - 2828]
[2]Current Patent Assignee: MODERNA THERAPEUTICS INC - WO2021/55835, 2021, A1
[3]Current Patent Assignee: MODERNA THERAPEUTICS INC - WO2021/55833, 2021, A1

70
[ 462-18-0 ]
[ 80256-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Zn / benzene / 1.5 h / Heating 2: 1.) formic acide, 2.) H₂ / 2.) 5 percent Pd/C / 1.) 1 h, reflux ; 2.) methanol, rt 3: thionyle chloride / 1 h / Heating

Reference： [1]Malthete, Jacques; Canceill, Josette; Gabard, Jacqueline; Jacques, Jean [Tetrahedron, 1981, vol. 37, # 16, p. 2823 - 2828]

71
[ 462-18-0 ]
[ 260055-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Zn / benzene / 1.5 h / Heating 2: 1.) formic acide, 2.) H₂ / 2.) 5 percent Pd/C / 1.) 1 h, reflux; 2.) methanol, rt
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.83 h / 20 °C 1.2: 0 °C / Reflux 2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C 1.2: 0 °C / Reflux 2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h

Reference： [1]Malthete, Jacques; Canceill, Josette; Gabard, Jacqueline; Jacques, Jean [Tetrahedron, 1981, vol. 37, # 16, p. 2823 - 2828]
[2]Current Patent Assignee: MODERNA THERAPEUTICS INC - WO2021/55835, 2021, A1
[3]Current Patent Assignee: MODERNA THERAPEUTICS INC - WO2021/55833, 2021, A1

72
[ 462-18-0 ]
(2,2-dihexyl-1,3-dioxolan-4-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In glycerol	P.2 Production Example 2 Production Example 2 A reactor equipped with a stirrer, reflux-condenser, thermometer and nitrogen gas inlet pipe was charged with 297 g of 7-tridecanone, 166 g of glycerol and a solvent amount of toluene, and after addition of p-toluenesulfonic acid as a catalyst, the dehydrative condensation reaction was carried out at the reflux temperature for 24 hours. The resulting crude product was washed with an aqueous solution of potassium carbonate and further with 3 portions of distilled water and finally purified by distillation under reduced pressure to provide 2,2-dihexyl-4-hydroxymethyl-1,3-dioxolane.

Reference： [1]Current Patent Assignee: DKS CO., LTD. - US6307069, 2001, B1

73
[ 462-18-0 ]
[ 26077-63-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium hydroxide; hydroxylamine hydrochloride In methanol at 60℃; for 24h;
	With hydroxylamine; sodium hydroxide In ethanol; water

Reference： [1]Soh, Nobuaki; Ariyoshi, Tomoyuki; Fukaminato, Tuyoshi; Nakajima, Hizuru; Nakano, Koji; Imato, Toshihiko [Organic and Biomolecular Chemistry, 2007, vol. 5, # 23, p. 3762 - 3768]
[2]Chen, Huaqing; Wang, Ling; Sun, Hua; Liu, Qian; Tan, Xiao; Sang, Shenglong; Wu, Bo; Zhang, Cong; Chen, Fei; Hang, Xiao-Chun; Chen, Zhi-Kuan [New Journal of Chemistry, 2020, vol. 44, # 30, p. 13093 - 13099]

74
[ 462-18-0 ]
[ 202650-88-2 ]
[ 1067649-95-9 ]

Yield	Reaction Conditions	Operation in experiment
27.5%	With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at 20℃; Ice cooling;

Reference： [1]Location in patent: experimental part Ma, Chao-Mei; Hattori, Masao; Daneshtalab, Mohsen; Wang, Lili [Journal of Medicinal Chemistry, 2008, vol. 51, # 19, p. 6188 - 6194]

75
[ 67-56-1 ]
[ 592-41-6 ]
[ 462-18-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With 2-Amino-4-methylpyridine; Wilkinson's catalyst; benzoic acid In toluene for 24h; Heating;

Reference： [1]Location in patent: body text Jo, Eun-Ae; Lee, Ji-Hyun; Jun, Chul-Ho [Chemical Communications, 2008, # 44, p. 5779 - 5781]

76
[ 3761-92-0 ]
[ 530-62-1 ]
[ 462-18-0 ]
[ 5340-59-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	In tetrahydrofuran at -80 - 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Bottalico, Daniela; Fiandanese, Vito; Marchese, Giuseppe; Punzi, Angela [Synthesis, 2009, # 14, p. 2316 - 2318]

77
[ 462-18-0 ]
[ 64472-35-1 ]
[ 1219687-74-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2'-iodo-2,5-dimethyl-biphenyl With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: tridecan-7-one In tetrahydrofuran at -78 - 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Laughlin, Brynna J.; Smith, Rhett C. [Macromolecules, 2010, vol. 43, # 8, p. 3744 - 3749]

78
[ 462-18-0 ]
[ 69272-50-0 ]
[ 1214719-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In diethyl ether at 50℃;
	With acetic acid In diethyl ether for 50h;

Reference： [1]Location in patent: experimental part Song, Suhee; Park, Sung Heum; Jin, Youngeup; Kim, Il; Lee, Kwanghee; Suh, Hongsuk [Polymer, 2010, vol. 51, # 23, p. 5385 - 5391]
[2]Location in patent: experimental part Song, Suhee; Park, Sung Heum; Jin, Youngeup; Park, Jina; Shim, Joo Young; Kim, Il; Lee, Heesoo; Lee, Kwanghee; Suh, Hongsuk [Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 20, p. 4567 - 4573]

79
[ 462-18-0 ]
[ 2231-57-4 ]
[ 18801-56-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With acetic acid In ethanol for 3h; Reflux;

Reference： [1]Location in patent: experimental part Tashtoush, Hasan I.; Abusahyon, Fatima; Shkoor, Mohanad; Al-Talib, Mahmoud [Journal of Sulfur Chemistry, 2011, vol. 32, # 5, p. 405 - 412]

80
[ 462-18-0 ]
(5-bromo-2,9-bis(1-hexylheptyl)anthra[2,1,9-def:6,5,10-d'e'f']diiso-quinoline-1,3,8,10(2H,9H)-tetrone) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ammonium acetate; sodium cyanotrihydridoborate / methanol / 60 h / 20 °C 2: 1H-imidazole / 4 h / 160 °C 3: bromine / dichloromethane / 96 h / 20 °C
	Multi-step reaction with 3 steps 1: ammonium acetate; sodium tetrahydridoborate / methanol / 24 h / 30 °C 2: 1H-imidazole / 4 h / 140 °C 3: bromine / 96 h / 20 °C
	Multi-step reaction with 4 steps 1: hydroxylamine; sodium hydroxide / ethanol; lithium hydroxide monohydrate 2: lithium aluminium hydride / tetrahydrofuran 3: 1H-imidazole / 150 °C 4: bromine / chloroform / 48 h / 30 °C

Multi-step reaction with 3 steps 1: ammonium acetate; sodium cyanotrihydridoborate / methanol / 60 h / 20 °C / Inert atmosphere 2: 1H-imidazole / 4 h / 180 °C / Inert atmosphere 3: bromine / dichloromethane / 48 h / 20 °C / Inert atmosphere

Reference： [1]Myahkostupov, Mykhaylo; Prusakova, Valentina; Oblinsky, Daniel G.; Scholes, Gregory D.; Castellano, Felix N. [Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8634 - 8644]
[2]Myahkostupov, Mykhaylo; Castellano, Felix N. [Tetrahedron, 2015, vol. 71, # 51, p. 9519 - 9527]
[3]Chen, Huaqing; Wang, Ling; Sun, Hua; Liu, Qian; Tan, Xiao; Sang, Shenglong; Wu, Bo; Zhang, Cong; Chen, Fei; Hang, Xiao-Chun; Chen, Zhi-Kuan [New Journal of Chemistry, 2020, vol. 44, # 30, p. 13093 - 13099]
[4]Current Patent Assignee: UNIV SUN YAT SEN - CN114369103, 2022, A

81
[ 462-18-0 ]
[ 611-99-4 ]
1,1-bis(4-hydroxyphenyl)-2-hexyloct-1-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With titanium tetrachloride; zinc In tetrahydrofuran at 0 - 90℃; for 2h; Inert atmosphere; Darkness;	1,1-Bis(4-hydroxyphenyl)-2-hexyloct-1-ene To a suspension of zinc powder (464 mg, 7.10 mmol) in THF (3 mL) at -10 °C was added titanium(IV) chloride (d 1.726, 0.350 mL, 3.18 mmol). The reaction mixture was diluted with THF (1 mL) and then refluxed at 90 °C (bath temperature) for 2 h and then a mixture of 4,4’-dihydroxybenzophenone (360 mg, 1.68 mmol) and 7-tridecanone (104 mg, 0.524mmol) in THF (8 mL) was added to the mixture at 0 °C. After the reaction mixture had been refluxed at 90 °C (bath temperature) for 2 h in the dark, 10% aqueous potassium carbonate was added to the mixture at 0 °C in the light. The mixture was filtered through a short pad of Celite with ethyl acetate, and the filtrate was extracted with ethyl acetate. The organic layer was washed with brine, and dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; hexane/ethylacetate = 2/1) to afford 1,1-bis(4-hydroxyphenyl)-2-hexyloct-1-ene (177 mg, 89%) as a white solid

Reference： [1]Hasegawa, Makoto; Yasuda, Yukari; Tanaka, Makoto; Nakata, Kenya; Umeda, Eri; Wang, Yanwen; Watanabe, Chihiro; Uetake, Shoko; Kunoh, Tatsuki; Shionyu, Masafumi; Sasaki, Ryuzo; Shiina, Isamu; Mizukami, Tamio [European Journal of Medicinal Chemistry, 2014, vol. 71, p. 290 - 305]

82
[ 462-18-0 ]
[ 5927-18-4 ]
methyl 3-hexylnon-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8 g	Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil for 2h; Cooling with ice; Stage #2: tridecan-7-one In tetrahydrofuran; mineral oil for 97h; Cooling with ice; Reflux;	113.113a Intermediate 113a: methyl 3-hexylnon-2-enoate Intermediate 113a: methyl 3-hexylnon-2-enoate To a suspension of sodium hydride (60% in paraffin oil, 14.16g, 335 mmol) in THF (500 ml_), cooled in an ice-water bath, was slowly added trimethyl phosphonoacetate (50.74g, 278.8 mmol). After 2h, tridecan-7-one (6.5g, 32.8 mmol) was slowly added, and the reaction was warmed to ambient temperature. After 1 h, the reaction was heated to reflux. After 4 days, the reaction was cooled, and 1 N HCI (aq) was added to quench the reaction. The reaction was extracted with ethyl acetate (3 x 200 ml_). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified on silica gel, using ethyl acetate / hexanes as eluent to provide 8.0g of the desired product. TLC (silica gel, 10% ethyl acetate in hexanes): Rf = 0.72.
8.0 g	Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil for 2h; Cooling with ice; Stage #2: tridecan-7-one In tetrahydrofuran; paraffin oil for 100h; Cooling with ice; Reflux;	23 Intermediate 23a: methyl 3-hexylnon-2-enoate To a suspension of sodium hydride (60% in paraffin oil, 14.16g, 335 mmol) in THF (500 mL), cooled in an ice-water bath, was slowly added trimethyl phosphonoacetate (50.74g, 278.8 mmol). After 2h, tridecan-7-one (6.5g, 32.8 mmol) was slowly added, and the reaction was warmed to ambient temperature. After 1 h, the reaction was heated to reflux. After 4 days, the reaction was cooled, and 1 N HCI (aq) was added to quench the reaction. The reaction was extracted with ethyl acetate (3 x 200 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified on silica gel, using ethyl acetate / hexanes as eluent to provide 8.0g of the desired product. TLC (silica gel, 10% ethyl acetate in hexanes): Rf = 0.72.
8 g	Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil for 2h; Cooling with ice; Stage #2: tridecan-7-one In tetrahydrofuran; paraffin oil at 20℃; for 97h; Reflux;	26.26a Intermediate 26a: methyl 3-hexylnon-2-enoate Intermediate 26a: methyl 3-hexylnon-2-enoate To a suspension of sodium hydride (60% in parafin oil, 14.16g, 335 mmol) in THF (500 mL), cooled in an ice-water bath, was slowly added trimethyl phosphonoacetate (50.74g, 278.8 mmol) to control gas evolution. After the addition was finished, the reaction was stirred for 2h then tridecan-7-one (6.5g, 32.8 mmol) was slowly added, and the reaction was warmed to ambient temperature. After 1 h additional, the reaction was heated to reflux. After 4d, the reaction was cooled, and 1 N HCI (aq) was added to quench the reaction. The reaction was extracted with ethyl acetate (3 x 200 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified on silica gel, using ethyl acetate / hexanes as eluent to provide 8.0g of the desired product. TLC (silica gel, 10% ethyl acetate in hexanes): Rf = 0.72.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2014/136086, 2014, A1 Location in patent: Page/Page column 172
[2]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2015/95340, 2015, A1 Location in patent: Page/Page column 92
[3]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2015/95346, 2015, A1 Location in patent: Page/Page column 118

83
[ 462-18-0 ]
(1,1-dihexylhexa-1,5-dien-3-yl)(phenyl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: n-butyllithium / tetrahydrofuran / 48 h / 0 - 20 °C 2: sodium hydroxide / water; dichloromethane / 24 h / 25 °C 3: titanium(IV) isopropylate; ethylmagnesium bromide / tetrahydrofuran / 4 h / 25 °C 4: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 23.5 h / 25 - 55 °C 5: dirhodium tetraacetate / tetrahydrofuran / 36 h / 50 °C / Schlenk technique; Inert atmosphere

Reference： [1]Zhang, Hang; Wang, Bo; Yi, Heng; Zhang, Yan; Wang, Jianbo [Organic Letters, 2015, vol. 17, # 13, p. 3322 - 3325]

84
[ 462-18-0 ]
3,3-dihexylcycloprop-1-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: n-butyllithium / tetrahydrofuran / 48 h / 0 - 20 °C 2: sodium hydroxide / lithium hydroxide monohydrate; dichloromethane / 24 h / 25 °C 3: titanium isopropoxide; ethynylmagnesium bromide / tetrahydrofuran / 4 h / 25 °C 4: potassium-t-butoxide / dimethyl sulfoxide / 23.5 h / 25 - 55 °C
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / 0 - 20 °C 1.2: 24 h / 0 - 20 °C 2.1: sodium hydroxide; N-hexadecyl-N,N,N-trimethylammonium bromide / lithium hydroxide monohydrate; dichloromethane / 25 °C 3.1: titanium isopropoxide; ethynylmagnesium bromide / diethyl ether; tetrahydrofuran / 3 h / 0 - 20 °C 4.1: potassium-t-butoxide / dimethyl sulfoxide / 55 °C

Reference： [1]Zhang, Hang; Wang, Bo; Yi, Heng; Zhang, Yan; Wang, Jianbo [Organic Letters, 2015, vol. 17, # 13, p. 3322 - 3325]
[2]Fors, Brett P.; Hsu, Jesse H.; Keresztes, Ivan; Lambert, Tristan H.; Quach, Phong K. [Angewandte Chemie - International Edition, 2022, vol. 61, # 24][Angew. Chem., 2022, vol. 134, # 24]

85
[ 462-18-0 ]
(6-hexyldodeca-1,2,5-trien-4-yl)(phenyl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: n-butyllithium / tetrahydrofuran / 48 h / 0 - 20 °C 2: sodium hydroxide / water; dichloromethane / 24 h / 25 °C 3: titanium(IV) isopropylate; ethylmagnesium bromide / tetrahydrofuran / 4 h / 25 °C 4: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 23.5 h / 25 - 55 °C 5: dirhodium tetraacetate / tetrahydrofuran / 36 h / 50 °C / Schlenk technique; Inert atmosphere

Reference： [1]Zhang, Hang; Wang, Bo; Yi, Heng; Zhang, Yan; Wang, Jianbo [Organic Letters, 2015, vol. 17, # 13, p. 3322 - 3325]

86
[ 462-18-0 ]
[ 1393672-10-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 48 h / 0 - 20 °C 2: sodium hydroxide / lithium hydroxide monohydrate; dichloromethane / 24 h / 25 °C
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / 0 - 20 °C 1.2: 24 h / 0 - 20 °C 2.1: sodium hydroxide; N-hexadecyl-N,N,N-trimethylammonium bromide / lithium hydroxide monohydrate; dichloromethane / 25 °C

Reference： [1]Zhang, Hang; Wang, Bo; Yi, Heng; Zhang, Yan; Wang, Jianbo [Organic Letters, 2015, vol. 17, # 13, p. 3322 - 3325]
[2]Fors, Brett P.; Hsu, Jesse H.; Keresztes, Ivan; Lambert, Tristan H.; Quach, Phong K. [Angewandte Chemie - International Edition, 2022, vol. 61, # 24][Angew. Chem., 2022, vol. 134, # 24]

87
[ 462-18-0 ]
[ 1393672-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / 48 h / 0 - 20 °C 2: sodium hydroxide / lithium hydroxide monohydrate; dichloromethane / 24 h / 25 °C 3: titanium isopropoxide; ethynylmagnesium bromide / tetrahydrofuran / 4 h / 25 °C
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / 0 - 20 °C 1.2: 24 h / 0 - 20 °C 2.1: sodium hydroxide; N-hexadecyl-N,N,N-trimethylammonium bromide / lithium hydroxide monohydrate; dichloromethane / 25 °C 3.1: titanium isopropoxide; ethynylmagnesium bromide / diethyl ether; tetrahydrofuran / 3 h / 0 - 20 °C

Reference： [1]Zhang, Hang; Wang, Bo; Yi, Heng; Zhang, Yan; Wang, Jianbo [Organic Letters, 2015, vol. 17, # 13, p. 3322 - 3325]
[2]Fors, Brett P.; Hsu, Jesse H.; Keresztes, Ivan; Lambert, Tristan H.; Quach, Phong K. [Angewandte Chemie - International Edition, 2022, vol. 61, # 24][Angew. Chem., 2022, vol. 134, # 24]

88
[ 462-18-0 ]
[ 1779-49-3 ]
[ 19780-80-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: triphenylmethylphosphonium bromide With potassium-t-butoxide In tetrahydrofuran at 0℃; for 0.75h; Stage #2: di-n-hexyl ketone In tetrahydrofuran at 0 - 23℃; for 16h;
71%	Stage #1: triphenylmethylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 3h; Stage #2: di-n-hexyl ketone In tetrahydrofuran; hexane at 0 - 20℃; for 24h;
	With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 48h;

	With potassium-t-butoxide In tetrahydrofuran at 0 - 20℃; for 16h;
	Stage #1: triphenylmethylphosphonium bromide With potassium-t-butoxide In tetrahydrofuran at 0℃; for 0.75h; Stage #2: di-n-hexyl ketone In tetrahydrofuran at 0 - 20℃;

Reference： [1]Qin, Ling; Sharique, Mohammed; Tambar, Uttam K. [Journal of the American Chemical Society, 2019, vol. 141, # 43, p. 17305 - 17313]
[2]Fors, Brett P.; Hsu, Jesse H.; Keresztes, Ivan; Lambert, Tristan H.; Quach, Phong K. [Angewandte Chemie - International Edition, 2022, vol. 61, # 24][Angew. Chem., 2022, vol. 134, # 24]
[3]Zhang, Hang; Wang, Bo; Yi, Heng; Zhang, Yan; Wang, Jianbo [Organic Letters, 2015, vol. 17, # 13, p. 3322 - 3325]
[4]Zhang, Zi-Yu; Liu, Zhi-Yun; Guo, Rui-Ting; Zhao, Yu-Quan; Li, Xiang; Wang, Xiao-Chen [Angewandte Chemie - International Edition, 2017, vol. 56, # 14, p. 4028 - 4032][Angew. Chem., 2017, vol. 129, # 14, p. 4086 - 4090,5]
[5]Wang, Di; Xue, Xiao-Song; Houk, Kendall N.; Shi, Zhuangzhi [Angewandte Chemie - International Edition, 2018, vol. 57, # 51, p. 16861 - 16865][Angew. Chem., 2018, vol. 130, # 51, p. 17103 - 17107,5]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	462-18-0	MDL No. :	MFCD00009543
Formula :	C₁₃H₂₆O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ULIAPOFMBCCSPE-UHFFFAOYSA-N
M.W :	198.34	Pubchem ID :	10015
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
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P264	Wash hands thoroughly after handling.
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P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
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P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
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.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H251	Self-heating; may catch fire
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
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
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. 462-18-0 ] {[proInfo.proName]}

Quality Control of [ 462-18-0 ]

Related Doc. of [ 462-18-0 ]

Product Details of [ 462-18-0 ]

Safety of [ 462-18-0 ]

Application In Synthesis of [ 462-18-0 ]

[ 462-18-0 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry