[ CAS No. 1117-61-9 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 1117-61-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1117-61-9 ]

Product Details of [ 1117-61-9 ]

CAS No. :	1117-61-9	MDL No. :	MFCD00063215
Formula :	C₁₀H₂₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	156.27	Pubchem ID :	-
Synonyms :	(+)-β-Citronellol;D-Citronellol;AI3-00204;(+)-(R)-Citronellol;(+)-Citronellol;(R)-(+)-β-Citronellol

Safety of [ 1117-61-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1117-61-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1117-61-9 ]
Downstream synthetic route of [ 1117-61-9 ]

[ 1117-61-9 ] Synthesis Path-Upstream 1~1

1
[ 1209493-70-8 ]
[ 5431-44-7 ]
[ 1117-61-9 ]

Reference： [1] Chemistry and Biodiversity, 2012, vol. 9, # 4, p. 689 - 701

[ 1117-61-9 ] Synthesis Path-Downstream 1~17

1
[ 1117-61-9 ]
[ 18951-85-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With jones reagent at 20℃; for 2h;
72%	With dipyridinium dichromate In N,N-dimethyl-formamide for 16h;
	With potassium dichromate; sulfuric acid; water

With Geotrichum candidum JCM 01747 In various solvent(s) at 30℃; for 240h; Microbiological reaction;

Reference： [1]Yabuuchi, Tetsuya; Kusumi, Takenori [Journal of Organic Chemistry, 2000, vol. 65, # 2, p. 397 - 404]
[2]Comeau, Christian; Ries, Benjamin; Stadelmann, Thomas; Tremblay, Jacob; Poulet, Sylvain; Fröhlich, Ulrike; Côté, Jérôme; Boudreault, Pierre-Luc; Derbali, Rabeb Mouna; Sarret, Philippe; Grandbois, Michel; Leclair, Grégoire; Riniker, Sereina; Marsault, Éric [Journal of Medicinal Chemistry, 2021, vol. 64, # 9, p. 5365 - 5383]
[3]Tiemann; Schmidt [Chemische Berichte, 1897, vol. 30, p. 27][Chemische Berichte, 1896, vol. 29, p. 913]
[4]Oda, Shinobu; Sugai, Takeshi; Ohta, Hiromichi [Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 12, p. 2819 - 2823]

2
[ 18951-85-4 ]
[ 1117-61-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With lithium aluminium tetrahydride
97%	With lithium aluminium tetrahydride In diethyl ether at 0℃;
97%	With lithium aluminium tetrahydride In diethyl ether

92%	With lithium aluminium tetrahydride In diethyl ether for 3h; Ambient temperature;
90%	With lithium aluminium tetrahydride In diethyl ether for 5h; Ambient temperature;
87.3%	With lithium aluminium tetrahydride
87%	With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h;
83%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 3h; Inert atmosphere;
80%	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.25h;
	With lithium aluminium tetrahydride; diethyl ether
69.2 g	With lithium aluminium tetrahydride In diethyl ether for 5h; Ambient temperature;
	With lithium aluminium tetrahydride
	Multi-step reaction with 2 steps 1: NaOH 2: LiAlH₄
	With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h; Inert atmosphere;	(R)-tert-Butyl((3,7-dimethyloct-6-en-1-yl)oxy)diphenylsilane (7): To a stirred suspension of LiAlH4 (1.1 g, 30.00 mmol) in dry ether (15 mL) at 0 °C was added dropwise a solution of 5 (1.7g, 10.0 mmol)) in dry ether (10 mL) under N2 atmosphere. After stirring for 1 h at the same temperature, reaction mixture was diluted with ether, quenched with dropwise addition of saturated aqueous Na2SO4 solution (5 mL). The solid material was filtered and washed thoroughly with hot EtOAc for several times. The combined organic layers were dried over Na2SO4. Solvent was removed in vacuo to afford the crude alcohol 6, which without further purification treated with imidazole (2.04 g, 30.00 mmol) and TBDPS-Cl (2.87 mL, 11.00 mmol) in anhydrous CH2Cl2 (10 mL) at 0 °C. Reaction mixture was stirred at room temperature for 2 h. After completion of the reaction it was diluted with CH2Cl2 and washed with water, brine and dried over anhydrous Na2SO4. Removal of solvent in vacuum and purification by silica gel column chromatography (5% ethyl acetate in hexane) afforded the compound 7 (3.54 g, 90% yield, over two steps). Rf = 0.8 (10% EtOAc/hexane). [α]D25 = 0.4 (c = 0.9, CHCl3); 1H NMR (300 MHz, CDCl3): 7.69 (4H, d, J = 8.0 Hz), 7.45-7.32 (6H, m), 5.08 (1H, t, J = 7.0 Hz), 3.75-3.62 (2H, m), 2.02-1.90 (2H, m), 1.69 (3H, s), 1.60 (3H, s), 1.02 (9H, s), 0.82 (3H, d, J = 7.0 Hz); 13C NMR (75 MHz, CDCl3): 135.8, 134.0, 131.0, 129.8, 127.9, 124.9, 62.2, 39.9, 37.0, 31.1, 27.0, 25.7, 25.2, 19.9, 19.1, 19.0; ESIMS: m/z 395 [M + H]+, Anal. Cald. for C26H38OSi: C, 79.12; H, 9.70. Found: C, 79.15; H, 9.66.

Reference： [1]Naoshima, Yoshinobu; Hayashi, Daijiro; Ochi, Masato [Agricultural and Biological Chemistry, 1988, vol. 52, # 6, p. 1605 - 1606]
[2]White, James D.; Amedio, John C.; Gut, Samuel; Ohira, Susumu; Jayasinghe, Lalith R. [Journal of Organic Chemistry, 1992, vol. 57, # 8, p. 2270 - 2284]
[3]White, James D.; Jayasinghe, Lalith R. [Tetrahedron Letters, 1988, vol. 29, # 18, p. 2139 - 2142]
[4]Mori; Masuda; Suguro [Tetrahedron, 1981, vol. 37, # 7, p. 1329 - 1340]
[5]Thijs, L.; Stokkingreef, E. H. M.; Lemmens, J. M.; Zwanenburg, B. [Tetrahedron, 1985, vol. 41, # 14, p. 2949 - 2956]
[6]Suzuki, Takahisa; Ozaki, Jotaro; Sugawara, Ryozo [Agricultural and Biological Chemistry, 1983, vol. 47, # 4, p. 869 - 876]
[7]Raederstorff, Daniel; Shu, Arthur Y.L.; Thompson, Janice E.; Djerassi, Carl [Journal of Organic Chemistry, 1987, vol. 52, # 12, p. 2337 - 2346]
[8]Verma, Ajay; Jana, Sadhan; Prasad, Ch. Durga; Yadav, Abhimanyu; Kumar, Sangit [Chemical Communications, 2016, vol. 52, # 22, p. 4179 - 4182]
[9]Chen, Cheng Yu; Nagumo, Shinji; Akita, Hiroyuki [Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 11, p. 2153 - 2156]
[10]Plesek [Collection of Czechoslovak Chemical Communications, 1957, vol. 22, p. 644] Lukes et al. [Croatica Chemica Acta, 1957, vol. 29, p. 201,204]
[11]Mori, Kenji; Waku, Michiru [Tetrahedron, 1984, vol. 40, # 2, p. 305 - 309]
[12]Mori, K.; Kuwahara, S.; Levinson, H. Z.; Levinson, A. R. [Tetrahedron, 1982, vol. 38, # 15, p. 2291 - 2297]
[13]Kikukawa, Tadashi; Imaida, Motomasa; Tai, Akira [Chemistry Letters, 1982, p. 1799 - 1802]
[14]Kumar, Jayprakash Narayan; Das, Biswanath [Synlett, 2014, vol. 25, # 6, p. 863 - 865]

3
[ 106-25-2 ]
[ 1117-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	With {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I; hydrogen In methanol; water at 20℃; for 8h;
	With hydrogen In methanol at 18 - 20℃; Yield given;
92 % ee	With bis(norbornadiene)rhodium(l)tetrafluoroborate; (R_C,S_Fc,S_P)-1-[2-(1-N,N-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-dicyclohexylphosphinoferrocene; hydrogen In dichloromethane at 20℃; for 20h; Inert atmosphere; Autoclave; enantioselective reaction;

Reference： [1]Mashima, Kazushi; Kusano, Koh-hei; Ohta, Tetsuo; Noyori, Ryoji; Takaya, Hidemasa [Journal of the Chemical Society. Chemical communications, 1989, # 17, p. 1208 - 1210]
[2]Takaya, Hidemasa; Ohta, Tetsuo; Sayo, Noboru; Kumobayashi, Hidenori; Akutagawa, Susumu; et al. [Journal of the American Chemical Society, 1987, vol. 109, # 5, p. 1596 - 1597]
[3]Wang, Quanjun; Liu, Xueying; Liu, Xian; Li, Bin; Nie, Huifang; Zhang, Shengyong; Chen, Weiping [Chemical Communications, 2014, vol. 50, # 8, p. 978 - 980]

4
[ 106-24-1 ]
[ 7540-51-4 ]
[ 1117-61-9 ]
[ 1117-60-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In methanol; water at 20℃; for 8h; Yield given. Yields of byproduct given;

Reference： [1]Mashima, Kazushi; Kusano, Koh-hei; Sato, Naomasa; Matsumura, Yoh-ichi; Nozaki, Kyoko; et al. [Journal of Organic Chemistry, 1994, vol. 59, # 11, p. 3064 - 3076]

5
[ 106-24-1 ]
[ 7540-51-4 ]
[ 1117-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	With <<(-)-2,2'-bis(diphenylphosphino)-4,4',6,6'-tetramethyl-3,3'-bibenzo<b>thiophene>Ru(p-cumene)I>I; hydrogen In methanol at 25℃; for 88h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With ((S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine))Ru(O₂CCF₃)2; hydrogen In methanol at 20 - 25℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With hydrogen In benzene Ambient temperature; Yield given. Yields of byproduct given;

	With hydrogen In benzene for 8h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With Ru₂Cl₄-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)₂NEt₃; hydrogen In methanol at 19.9℃; Title compound not separated from byproducts;
	With <(-)-2,2'-bis(diphenylphosphino)-4,4',6,6'-tetramethyl-3,3'-bibenzo<b>thiophene>Ru(CH3COO)2; hydrogen In methanol at 25℃; for 85h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With ((S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine))Ru(O₂CCF₃)2; hydrogen In methanol at 20 - 25℃; for 1h; different catalysts; var. unsaturated substrates;
	With hydrogen In benzene Ambient temperature; enantioselectivity of hydrogenation of geraniol and nerol between var. conditions;
	With hydrogen In benzene for 8h; Ambient temperature; var. solvents;
	With Ru₂Cl₄-((S)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)₂NEt₃; hydrogen In methanol at 9.9℃; other allylic alcohol; also with α-keto ester and olefin; other catalysts; var. H2 pressure; enantioselective asymmetric hydrogenation;
	With hydrogen In methanol at 49.9℃; different time and agitation speed; other pressure and temperature;
	With Ru((R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)(MeCN)(1,3:5,6-η-C8H11)(BF4); hydrogen In methanol at 25℃; for 0.25h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
	With (+)-[4,4'-(PPh₂)2-2,2',5,5'-Me₄-3,3'-bithiophene]RuCl₂; hydrogen In methanol at 25℃; for 6.5h; Title compound not separated from byproducts.;
	With hydrogen In methanol at 20℃; for 20h; Title compound not separated from byproducts.;
	With hydrogen In methanol at 20℃; Title compound not separated from byproducts.;
	With 1,2-bis(2,5-diisopropylphospholano)benzene; potassium hydroxide at 100℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
	With (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; potassium hydroxide at 100℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

Reference： [1]Benincori, Tiziana; Brenna, Elisabetta; Sannicolo, Franco; Trimarco, Licia; Antognazza, Patrizia; et al. [Journal of Organic Chemistry, 1996, vol. 61, # 18, p. 6244 - 6251]
[2]Heiser; Broger; Crameri [Tetrahedron Asymmetry, 1991, vol. 2, # 1, p. 51 - 62]
[3]Inoue, Shin-ichi; Osada, Masato; Koyano, Kinko; Takaya, Hidemasa; Noyori, Ryoji [Chemistry Letters, 1985, p. 1007 - 1008]
[4]Ali; Allaoud; Karim; Roucoux; Mortreux [Tetrahedron Asymmetry, 1995, vol. 6, # 2, p. 369 - 370]
[5]Sun, Yongkui; LeBlond, Carl; Wang, Jian; Blackmond, Donna G.; Laquidara, Joseph; Sowa Jr., John R. [Journal of the American Chemical Society, 1995, vol. 117, # 50, p. 12647 - 12648]
[6]Benincori, Tiziana; Brenna, Elisabetta; Sannicolo, Franco; Trimarco, Licia; Antognazza, Patrizia; et al. [Journal of Organic Chemistry, 1996, vol. 61, # 18, p. 6244 - 6251]
[7]Heiser; Broger; Crameri [Tetrahedron Asymmetry, 1991, vol. 2, # 1, p. 51 - 62]
[8]Inoue, Shin-ichi; Osada, Masato; Koyano, Kinko; Takaya, Hidemasa; Noyori, Ryoji [Chemistry Letters, 1985, p. 1007 - 1008]
[9]Ali; Allaoud; Karim; Roucoux; Mortreux [Tetrahedron Asymmetry, 1995, vol. 6, # 2, p. 369 - 370]
[10]Sun; Landau; Wang; LeBlond; Blackmond [Journal of the American Chemical Society, 1996, vol. 118, # 6, p. 1348 - 1353]
[11]Sun, Yongkui; Wang, Jian; LeBlond, Carl; Reamer, Robert A.; Laquidara, Joseph; Sowa Jr., John R.; Blackmond, Donna G. [Journal of Organometallic Chemistry, 1997, vol. 548, # 1, p. 65 - 72]
[12]Daley, Christopher J.A.; Wiles, Jason A.; Bergens, Steven H. [Canadian Journal of Chemistry, 1998, vol. 76, # 10, p. 1447 - 1456]
[13]Benincori, Tiziana; Cesarotti, Edoardo; Piccolo, Oreste; Sannicolo, Franco [Journal of Organic Chemistry, 2000, vol. 65, # 7, p. 2043 - 2047]
[14]Denmark, Scott E.; Regens, Christopher S.; Kobayashi, Tetsuya [Journal of the American Chemical Society, 2007, vol. 129, # 10, p. 2774 - 2776]
[15]Cesarotti, Edoardo; Abbiati, Giorgio; Rossi, Elisabetta; Spalluto, Paola; Rimoldi, Isabella [Tetrahedron Asymmetry, 2008, vol. 19, # 14, p. 1654 - 1659]
[16]Location in patent: experimental part Wu, Ruoqiu; Beauchamps, Marie G.; Laquidara, Joseph M.; Sowa Jr., John R. [Angewandte Chemie - International Edition, 2012, vol. 51, # 9, p. 2106 - 2110]
[17]Location in patent: experimental part Wu, Ruoqiu; Beauchamps, Marie G.; Laquidara, Joseph M.; Sowa Jr., John R. [Angewandte Chemie - International Edition, 2012, vol. 51, # 9, p. 2106 - 2110]

6
[ 1117-61-9 ]
[ 69226-51-3 ]
3-((R)-5-Hydroxy-3-methyl-pentyl)-2,2-dimethyl-aziridine-1-sulfonic acid 2,2,2-trichloro-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With [bis(acetoxy)iodo]benzene; magnesium oxide In chlorobenzene at -10 - 23℃; for 8h;

Reference： [1]Guthikonda, Kiran; Wehn, Paul M.; Caliando, Brian J.; Du Bois [Tetrahedron, 2006, vol. 62, # 49, p. 11331 - 11342]

7
[ 1117-61-9 ]
[ 4144-54-1 ]
[ 104-15-4 ]
4-oxo-1-decanoic acid 3,7-dimethyl-oct-6-enyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In cyclohexane	4 4-Oxo-decanoic Acid 3,7-Dimethyl-oct-6-enyl Ester Example 4 4-Oxo-decanoic Acid 3,7-Dimethyl-oct-6-enyl Ester A solution of 20.0 g 4-oxo-1-decanoic acid (Synthesis, 1987, 408), 16.8 g citronellol extra and 0.5 g p-toluene-sulfonic acid in 150 ml of cyclohexane was refluxed in a flask equipped with a Dean-Stark trap for 3 hours. Then the reaction mixture was cooled, diluted with ether, washed with saturated NaHCO3 and water. The organic phase was dried, filtered and evaporated to dryness. The resulting oil was purified by chromatography to yield 31.7 g of a yellow oil. NMR (CDCl3): δ 5.04-5.19 (m, 1H), 4.11-4.17 (m, 2H), 2.68-2.79 (m, 2H), 2.53-2.60 (m, 2.41-2.48 (t, 2H), 2.03-1.91 (q, 2H), 1.75-1.44 (m, 6H), 1.43-1.08 (m, 12H), 0.92-0.84 (m, 6H) ppm.
	In cyclohexane	4 4-Oxo-decanoic Acid 3,7-Dimethyl-oct-6-enyl Ester Example 4 4-Oxo-decanoic Acid 3,7-Dimethyl-oct-6-enyl Ester A solution of 20.0 g 4-oxo-1-decanoic acid (Synthesis, 1987, 408), 16.8 g citronellol extra and 0.5 g p-toluene-sulfonic acid in 150 ml of cyclohexane was refluxed in a flask equipped with a Dean-Stark trap for 3 hours. Then the reaction mixture was cooled, diluted with ether, washed with saturated NaHCO3 and water. The organic phase was dried, filtered and evaporated to dryness. The resulting oil was purified by chromatography to yield 31.7 g of a yellow oil. NMR (CDCl3): d 5.04-5.19 (m, 1H), 4.11-4.17 (m, 2H), 2.68-2.79 (m, 2H), 2.53-2.60 (m, 2H), 2.41-2.48 (t, 2H), 2.03-1.91 (q, 2H), 1.75-1.44 (m, 6H), 1.43-1.08 (m, 12H), 0.92-0.84 (m, 6H) ppm.

Reference： [1]Current Patent Assignee: GIVAUDAN SA - US6437150, 2002, B1
[2]Current Patent Assignee: GIVAUDAN SA - US6479682, 2002, B1

8
[ 216369-04-9 ]
[ CAS Unavailable ]
[ 106-24-1 ]
[ 1117-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,2-dichloro-ethane	14 Synthesis of citronellol by the asymmetric hydrogenation of geraniol Example 14 Synthesis of citronellol by the asymmetric hydrogenation of geraniol 4.5 mg (0.01 mmol) of (-)-2-amino-2'-diphenylphosphino-1,1'-binaphthyl (the formula (1-1a)), 5.0 mg (0.01 mmol) of bis(1,5-cyclooctadiene)iridium tetrafluoroborate, 154 mg (1.0 mmol) of geraniol and 2 ml of ethylene chloride were charged into an autoclave and stirred at 30° C. for 20 hours in hydrogen atmosphere under a pressure of 4 atm. The solvent of the resultant reaction solution was evaporated under a reduced pressure. The residue was then measured by means of a gas chromotography to confirm the formation of citronelol with a chemical yield of 77 percent. The optical yield of citronellol was 96 percent confirmed by an optically active HPLC column chromatography.

Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US6323353, 2001, B1

9
[ 1117-61-9 ]
[ 609-23-4 ]
[ 124-63-0 ]
1-(2,4,6-triiodophenoxy)-3,7-dimethyl-6-octene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With potassium carbonate; triethylamine In <i>N</i>-methyl-acetamide; dichloromethane	20 1-(2,4,6-Triiodophenoxy)-3,7-dimethyl-6-octene STR23 EXAMPLE 20 1-(2,4,6-Triiodophenoxy)-3,7-dimethyl-6-octene STR23 To a stirred solution of citronellol (4.5 g, 28.8 mmol) and triethylamine (5.2 ml, 34.6 mmol, 1.2 eq) in dichloromethane (50 ml) cooled to 0° C. was added dropwise, a solution of methanesulfonyl chloride (2.46 ml, 28.8 mmol) in dichloromethane (50 ml). The solution was stirred for 1 hr. at 0° C. under nitrogen and then water was added. The dichloromethane layer was dried over magnesium sulfate after washing with saturated aqueous sodium chloride and then concentrated in vacuo to give an oil. 1 H-NMR (300 MHZ) spectrum of the oil indicated the desired methanesulfonate ester. The methanesulfonate ester was added to a stirred mixture of 2,4,6-triiodophenol (13.6 g, 28.8 mmol) and potassium carbonate (4.0 g, 28.8 mmol) in dimethylformamide (50 ml). The mixture was heated to 100° C. for 30 minutes and cooled to room temperature. The crude product was isolated by partitioning the reaction mixture between water and dichloromethane. The organic layer was concentrated under vacuum to give an oil. The oil was purified by flashing through basic alumina with hexanes to give the desired product in 15% yield as a light-sensitive oil. Title Compound: 1 H (300 MHz) and 13 C (75 MHz) NMR spectra were consistent with the desired structure. Calculated for C16 H21 I3 O: C, 31.50; H, 3.47; I, 62.41. Found: C, 31.71; H, 3.41; I, 62.30.
15%	With potassium carbonate; triethylamine In <i>N</i>-methyl-acetamide; dichloromethane	20 1-(2,4,6-Triiodophenoxy)-3,7-dimethyl-6-octene STR23 EXAMPLE 20 1-(2,4,6-Triiodophenoxy)-3,7-dimethyl-6-octene STR23 To a stirred solution of citronellol (4.5 g, 28.8 mmol) and triethylamine (5.2 ml, 34.6 mmol, 1.2 eq) in dichloromethane (50 ml) cooled to 0° C. was added dropwise, a solution of methanesulfonyl chloride (2.46 ml, 28.8 mmol) in dichloromethane (50 ml). The solution was stirred for 1hr at 0° C. under nitrogen and then water was added. The dichloromethane layer was dried over magnesium sulfate after washing with saturated aqueous sodium chloride and then concentrated in vacuo to give an oil. 1 H-NMR (300 MHZ) spectrum of the oil indicated the desired methanesulfonate ester. The methanesulfonate ester was added to a stirred mixture of 2,4,6-triiodophenol (13.6 g, 28.8 mmol) and potassium carbonate (4.0 g, 28.8 mmol) in dimethylformamide (50 ml). The mixture was heated to 100° C. for 30 minutes and cooled to room temperature. The crude product was isolated by partitioning the reaction mixture between water and dichloromethane. The organic layer was concentrated under vacuum to give an oil. The oil was purified by flashing through basic alumina with hexanes to give the desired product in 15% yield as a light-sensitive oil. Title Compound: 1 H (300 MHz) and 13 C (75 MHz) NMR spectra were consistent with the desired structure. Calculated for C16 H21 I3 O: C, 31.50; H, 3.47; I, 62.41. Found: C, 31.71; H, 3.41; I, 62.30.

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - US5326553, 1994, A
[2]Current Patent Assignee: GENERAL ELECTRIC CO - US5607660, 1997, A

10
[ 1117-61-9 ]
[ 10458-14-7 ]
[ 89-83-8 ]

Yield	Reaction Conditions	Operation in experiment
		1 EXAMPLE 1 EXAMPLE 1 Citronellol (156 g; 1 mole) and 7.8 g of a copper-chromium oxide catalyst (CuO:Cr2 O3 = 50:50 by weight; mainly as CuCr2 O4; less than 200 mesh, a product of Nikki Chemical Co., Ltd.) were charged into a pressure reactor, and reacted at 230° C under a hydrogen pressure of 2 kg/cm2.G. In about 4 hours, the evolution of hydrogen ended. The amount of hydrogen evolved was 24 liters. The catalyst was separated from the reaction product by filtration, and the residue was distilled under reduced pressure to afford 140 g of a fraction having a boiling point of 82° to 90° C/12 mmHg. This fraction was a mixture of menthone and iso-menthone in a ratio of 6:4 by weight. The theoretical yield was 90%. Also, 7.7 g of thymol boiling at 108° to 110° C/12 mmHg was obtained.

Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US4134919, 1979, A

11
[ 106-26-3 ]
[ 7540-51-4 ]
[ 1117-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	With glucose-6-phosphate dehydrogenase; D-glucose 6-phosphate; Saccharomyces pastorianus old yellow enzyme W₁₁₆F; NADP at 20℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
	With glucose-6-phosphate dehydrogenase; D-glucose 6-phosphate; Saccharomyces pastorianus old yellow enzyme wild type; NADP at 20℃; for 24h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
87 % ee	With C₅₈H₆₄FeN₂O₆P₂Rh⁽¹⁺⁾*BF₄^(1-); hydrogen at 15℃; for 18h; Autoclave; Overall yield = 93 %; enantioselective reaction;	32 Example 32 Preparation of chiral Citronellol 10mL in a reaction tube, was added phosphine ligand R-L14 (4.5mg, 0.005mmol) and bis (1,5 Cyclooctadiene) rhodium tetrafluoroborate [Rh (COD) 2] BF 4 (2.1mg, 0.005mmol), through the vacuum line system, with 3 times purged with nitrogen, was added freshly distilled degassed toluene (2mL), the solution was stirred for 1 hour at room temperature under reduced pressure. Removing the solvent to give a brown solid, after vacuum was 2 hours, the solvent was added 20mL of methanol, the solution was added Containing citral formula Z (7.6g, 50mmol, E / Z = 1/99, chiral rhodium complex [Rh (R-L14) (COD)] BF 4 The molar ratio of citral 1/10000) vial charged autoclave was purged with hydrogen six times after that beginning Starting hydrogen pressure of 30bar, 15 ° C the reaction was stirred for 18 hours. Cooling, carefully release the gas, high pressure open Kettle, remove the vials, solvent drained, NMR detection conversion rate, gas chromatography (column β-DEX 225) Detection enantiomer excess value ,, column chromatography to give the product. The yield was 93%, R- enantiomeric excess value of 87%.

Reference： [1]Location in patent: experimental part Padhi, Santosh Kumar; Bougioukou, Despina J.; Stewart, Jon D. [Journal of the American Chemical Society, 2009, vol. 131, p. 3271 - 3280]
[2]Location in patent: experimental part Padhi, Santosh Kumar; Bougioukou, Despina J.; Stewart, Jon D. [Journal of the American Chemical Society, 2009, vol. 131, p. 3271 - 3280]
[3]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN105254474, 2016, A Location in patent: Paragraph 0137-0138

12
[ 141-27-5 ]
[ 7540-51-4 ]
[ 1117-61-9 ]

Yield	Reaction Conditions	Operation in experiment
88 % ee	With C₅₆H₅₂O₄P₂Rh⁽¹⁺⁾*BF₄^(1-); hydrogen In methanol at 0℃; for 36h; Autoclave; Overall yield = 85 %; enantioselective reaction;	2 Preparation of chiral Citronellol 10mL in a reaction tube, was added phosphine ligand S-L1b (4.1mg, 0.005mmol) and bis (1,5 Cyclooctadiene) rhodium tetrafluoroborate [Rh (COD) 2] BF 4 (2.1mg, 0.005mmol), through the vacuum line system, with 3 times purged with nitrogen, was added freshly distilled degassed toluene (2mL), the solution was stirred for 1 hour at room temperature under reduced pressure. Removing the solvent to give a brown solid, after vacuum was 2 hours, the solvent was added 2mL of methanol, this catalyst solution Flask equipped with a formula E citral (76.1mg, 0.50mmol, E / Z = 99/1, the chiral rhodium complex [Rh (S-L1b) (COD)] BF 4 and the molar ratio of citral 1/100) of the vial, the autoclave was charged by 6 After times substituted with hydrogen, so that an initial hydrogen pressure of 10bar, 0 ° C The reaction was stirred for 36 hours. Cooling, carefully put The gas, the autoclave was opened, the vials removed, solvent drained, the conversion rate is detected NMR, gas chromatography (chromatography Column β-DEX 225) enantiomer detected excess value ,, column chromatography to give the product in a yield of 85%, R- Enantiomeric excess is 88%

Reference： [1]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN105254474, 2016, A Location in patent: Paragraph 0047-0049

13
[ 5392-40-5 ]
[ 26489-02-1 ]
[ 1117-61-9 ]
[ 106-25-2 ]
[ 106-24-1 ]

Yield	Reaction Conditions	Operation in experiment
	With cobalt boride; hydrogen In hexane at 149.84℃; for 1h; Autoclave;	2.3 Hydrogenation of citral Catalyzed test reactions were performed in high-pressure batch autoclaves (Parr, 300mL, stainless steel). To enhance comparability with experiments on other catalysts described in the literature, the catalysts were pre-treated at 423K and a H2 pressure of 1.5MPa in situ by stirring 250mg cobalt or nickel boride in 110ml n-hexane. After this procedure, the desired reaction temperatures (353, 393, 423K) and pressures (5MPa) were set, and citral (Merck, 10mL) in hexane (25mL, with tetradecan as internal standard) was added from a separate tank. Samples (50μl) were taken periodically after 0, 20, 30 or 40, 60, 90, 120, and 240min and analyzed offline by gas-chromatography for nerol, geraniol, citronellol, citronellal, and dimethyloctanol (Shimadzu GC 2010 Plus).

Reference： [1]Kalyon; Hofmann; Malter; Lucas; Claus; Albert [Journal of Catalysis, 2017, vol. 352, p. 436 - 441]

14
[ 5392-40-5 ]
[ 1117-61-9 ]
[ 106-25-2 ]
[ 106-24-1 ]

Yield	Reaction Conditions	Operation in experiment
	With cobalt boride; hydrogen In hexane at 149.84℃; for 1.5h; Autoclave;	2.3 Hydrogenation of citral Catalyzed test reactions were performed in high-pressure batch autoclaves (Parr, 300mL, stainless steel). To enhance comparability with experiments on other catalysts described in the literature, the catalysts were pre-treated at 423K and a H2 pressure of 1.5MPa in situ by stirring 250mg cobalt or nickel boride in 110ml n-hexane. After this procedure, the desired reaction temperatures (353, 393, 423K) and pressures (5MPa) were set, and citral (Merck, 10mL) in hexane (25mL, with tetradecan as internal standard) was added from a separate tank. Samples (50μl) were taken periodically after 0, 20, 30 or 40, 60, 90, 120, and 240min and analyzed offline by gas-chromatography for nerol, geraniol, citronellol, citronellal, and dimethyloctanol (Shimadzu GC 2010 Plus).
	With cobalt boride; hydrogen In hexane at 149.84℃; for 2h; Autoclave;	2.3 Hydrogenation of citral Catalyzed test reactions were performed in high-pressure batch autoclaves (Parr, 300mL, stainless steel). To enhance comparability with experiments on other catalysts described in the literature, the catalysts were pre-treated at 423K and a H2 pressure of 1.5MPa in situ by stirring 250mg cobalt or nickel boride in 110ml n-hexane. After this procedure, the desired reaction temperatures (353, 393, 423K) and pressures (5MPa) were set, and citral (Merck, 10mL) in hexane (25mL, with tetradecan as internal standard) was added from a separate tank. Samples (50μl) were taken periodically after 0, 20, 30 or 40, 60, 90, 120, and 240min and analyzed offline by gas-chromatography for nerol, geraniol, citronellol, citronellal, and dimethyloctanol (Shimadzu GC 2010 Plus).

Reference： [1]Kalyon; Hofmann; Malter; Lucas; Claus; Albert [Journal of Catalysis, 2017, vol. 352, p. 436 - 441]
[2]Kalyon; Hofmann; Malter; Lucas; Claus; Albert [Journal of Catalysis, 2017, vol. 352, p. 436 - 441]

15
[ 5392-40-5 ]
[ 1117-61-9 ]
[ 1117-60-8 ]

Yield	Reaction Conditions	Operation in experiment
	With cobalt boride; hydrogen In hexane at 149.84℃; for 4h; Autoclave;	2.3 Hydrogenation of citral Catalyzed test reactions were performed in high-pressure batch autoclaves (Parr, 300mL, stainless steel). To enhance comparability with experiments on other catalysts described in the literature, the catalysts were pre-treated at 423K and a H2 pressure of 1.5MPa in situ by stirring 250mg cobalt or nickel boride in 110ml n-hexane. After this procedure, the desired reaction temperatures (353, 393, 423K) and pressures (5MPa) were set, and citral (Merck, 10mL) in hexane (25mL, with tetradecan as internal standard) was added from a separate tank. Samples (50μl) were taken periodically after 0, 20, 30 or 40, 60, 90, 120, and 240min and analyzed offline by gas-chromatography for nerol, geraniol, citronellol, citronellal, and dimethyloctanol (Shimadzu GC 2010 Plus).

Reference： [1]Kalyon; Hofmann; Malter; Lucas; Claus; Albert [Journal of Catalysis, 2017, vol. 352, p. 436 - 441]

16
[ 111-17-1 ]
[ 1117-61-9 ]
[ 33069-62-4 ]
C₆₃H₇₇NO₁₇S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Add the appropriate amount of thiodipropionic acid to a 50 mL round bottom flask.It was dissolved in 3 mL of acetic anhydride and stirred at room temperature for 2 hours.The reaction was monitored by thin layer chromatography, after which 20 mL of toluene was added to the system three times.And vacuum distillation was carried out under reduced pressure.The obtained product was dissolved in 30 mL of dichloromethane.And add the right amount of citronellol and DMAP,Stir at room temperature for 1 hour.The reaction process was monitored by thin layer chromatography.Purification by silica gel column chromatography gave the intermediate.Finally, the intermediate product, EDCI, HOBt and DMAP were dissolved in 50 mL of anhydrous dichloromethane.Ice bath for 1 hour, then add the appropriate amount of paclitaxel, and stir for another 24 hours at room temperature.The reaction process was monitored by thin layer chromatography, and the desired product was obtained by preparative liquid chromatography. The above reaction was carried out under the protection of N2.

Reference： [1]Patent: CN109350748,2019,A .Location in patent: Paragraph 0061; 0062; 0063; 0064

17
[ 1117-61-9 ]
[ 766-08-5 ]
C₁₇H₂₈OSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With iron(II)β-diketiminate complex In benzene-d6 at 20℃; for 18h;

Reference： [1]Coles, Nathan T.; Gasperini, Danila; King, Andrew K.; Mahon, Mary F.; Webster, Ruth L. [ACS Catalysis, 2020, vol. 10, # 11, p. 6102 - 6112]

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[ CAS No. 1117-61-9 ] {[proInfo.proName]}

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[ 1117-61-9 ] Synthesis Path-Upstream 1~1

[ 1117-61-9 ] Synthesis Path-Downstream 1~17

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