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[ CAS No. 924-41-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 924-41-4
Chemical Structure| 924-41-4
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Quality Control of [ 924-41-4 ]

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Product Details of [ 924-41-4 ]

CAS No. :924-41-4 MDL No. :MFCD00008662
Formula : C6H10O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 98.14 Pubchem ID :-
Synonyms :

Safety of [ 924-41-4 ]

Signal Word:Danger Class:3
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235 UN#:1987
Hazard Statements:H225-H315-H319 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 924-41-4 ]

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

  • Downstream synthetic route of [ 924-41-4 ]

[ 924-41-4 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 106-95-6 ]
  • [ 107-02-8 ]
  • [ 924-41-4 ]
YieldReaction ConditionsOperation in experiment
94% With copper; tin(ll) chloride In water at 20℃; for 3h;
60% Stage #1: allyl bromide With magnesium In diethyl ether Inert atmosphere; Stage #2: acrolein In diethyl ether for 5h; Inert atmosphere; Reflux;
With zinc inactive vinylallylcarbinol;
(i) Mg, (ii) /BRN= 741856/; Multistep reaction;

Reference： [1]Tan, Xiang-Hui; Shen, Bo; Liu, Lei; Guo, Qing-Xiang [Tetrahedron Letters, 2002, vol. 43, # 51, p. 9373 - 9376]
[2]Dyson, Bryony S.; Burton, Jonathan W.; Sohn, Te-Ik; Kim, Byungsook; Bae, Hoon; Kim, Deukjoon [Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11781 - 11790]
[3]Levene; Haller [Journal of Biological Chemistry, 1929, vol. 83, p. 183]
[4]Dreyfuss,M.P. [Journal of Organic Chemistry, 1963, vol. 28, p. 3269 - 3272] Gibson,T.W.; Erman,W.F. [Journal of Organic Chemistry, 1972, vol. 37, # 8, p. 1148 - 1154]
  • 2
  • [ 107-02-8 ]
  • [ 1730-25-2 ]
  • [ 924-41-4 ]
YieldReaction ConditionsOperation in experiment
65% In diethyl ether
63% In diethyl ether for 1.75h; Heating;
inactive vinylallylcarbinol;
In diethyl ether at 0℃;

Reference： [1]Chattopadhyay, A.; Mamdapur, V. R. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 169]
[2]Barfield,M.; Brown,S.E.; Canada,E.D. [Journal of the American Chemical Society, 1980, vol. 102, p. 3355]
[3]Levene; Haller [Journal of Biological Chemistry, 1929, vol. 83, p. 183]
[4]Ou [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1939, vol. 208, p. 41][Annales de Chimie (Cachan, France), 1940, vol. <11>13, p. 220,223] Butz; Butz; Gaddis [Journal of Organic Chemistry, 1940, vol. 5, p. 171,180]
[5]Harayama, Hiroto; Abe, Atsuhiro; Sakado, Tomonori; Kimura, Masanari; Fugami, Keigo; Tanaka, Shuji; Tamaru, Yoshinao [Journal of Organic Chemistry, 1997, vol. 62, # 7, p. 2113 - 2122]
  • 3
  • [ 1069-23-4 ]
  • [ 924-41-4 ]
YieldReaction ConditionsOperation in experiment
With formamide at 100℃;
Reference： [1]Pascal,Y.-L.; Quetier,F. [Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 272, p. 490 - 493]
  • 4
  • [ 924-41-4 ]
  • [ 5164-64-7 ]
YieldReaction ConditionsOperation in experiment
(i) CrO3, H2SO4, (ii) (UV-irradiation); Multistep reaction;
Multi-step reaction with 2 steps 1: sodium dichromate dihydrate, conc. H2SO4 / diethyl ether / 2 h / 20 - 25 °C 2: 10 h / Irradiation
Multi-step reaction with 2 steps 1: Jones reagent / acetone / 1 h / 5 °C 2: 28 percent / pentane / 18 h / Irradiation
Multi-step reaction with 2 steps 1: CrO3, conc. H2SO4 / diethyl ether; H2O / 0.08 h 2: pentane / Irradiation
Multi-step reaction with 2 steps 1: aq. chromic acid / diethyl ether / 0.08 h / 15 °C 2: CuSO4*5H2O, 2,7-dimethyl-3,6-diazacyclohepta-1,6-dienyl perchlorate / diethyl ether / 27 h / Irradiation
Multi-step reaction with 2 steps 1: chromium trioxide, sulfuric acid / H2O; acetone; benzene / 0.25 h / 0 °C 2: pentane / 24 h / Irradiation
Multi-step reaction with 2 steps 1: pyridinium chlorochromate; silica gel / dichloromethane / Inert atmosphere 2: pentane / UV-irradiation; Inert atmosphere

Reference： [1]Gibson,T.W.; Erman,W.F. [Journal of Organic Chemistry, 1972, vol. 37, # 8, p. 1148 - 1154]
[2]Della, Ernest W.; Pigou, Paul E. [Australian Journal of Chemistry, 1983, vol. 36, # 11, p. 2261 - 2268]
[3]Barfield,M.; Brown,S.E.; Canada,E.D. [Journal of the American Chemical Society, 1980, vol. 102, p. 3355]
[4]Dauben, William G.; Cogen, Jeffrey M.; Ganzer, George A.; Behar, Victor [Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5817 - 5824]
[5]Della, Ernest W.; Elsey, Gordon M.; Skouroumounis, George [Australian Journal of Chemistry, 1990, vol. 43, # 7, p. 1231 - 1244]
[6]Newmann-Evans, Richard H.; Simon, Reyna J.; Carpenter, B. K. [Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 695 - 711]
[7]Troadec, Thibault; Wasano, Tatsuya; Lenk, Romaric; Baceiredo, Antoine; Saffon-Merceron, Nathalie; Hashizume, Daisuke; Saito, Yosuke; Nakata, Norio; Branchadell, Vicenç; Kato, Tsuyoshi [Angewandte Chemie - International Edition, 2017, vol. 56, # 24, p. 6891 - 6895][Angew. Chem., 2017, vol. 129, p. 6995 - 6999]
  • 5
  • [ 924-41-4 ]
  • [ 201230-82-2 ]
  • [ 134359-16-3 ]
YieldReaction ConditionsOperation in experiment
49% In 1,2-dimethoxyethane at 190℃; for 48h;
Reference： [1]El Ali, Bassam; Alper, Howard [Journal of Organic Chemistry, 1991, vol. 56, # 18, p. 5357 - 5360]
  • 6
  • [ 924-41-4 ]
  • [ 127492-03-9 ]
  • [ 136736-31-7 ]
YieldReaction ConditionsOperation in experiment
74% With mesitylenecarboxylic acid In dichloromethane at 100 - 120℃;
Reference： [1]Posner, Gary H.; Crouch, R. David; Kinter, Chris M.; Carry, Jean-Christophe [Journal of Organic Chemistry, 1991, vol. 56, # 25, p. 6981 - 6987]
  • 7
  • [ 924-41-4 ]
  • [ 61921-56-0 ]
  • (8R,9S,10R,13S,14S)-10,13-Dimethyl-17-(2-oxo-3-vinyl-hex-5-enyl)-1,2,6,7,8,9,10,11,12,13,14,15-dodecahydro-cyclopenta[a]phenanthren-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With ammonium hexafluorophosphate; triphenylphosphine at 100℃;
Reference： [1]Trost; Kulawiec; Hammes [Tetrahedron Letters, 1993, vol. 34, # 4, p. 587 - 590]
  • 8
  • [ 924-41-4 ]
  • [ 24058-61-5 ]
YieldReaction ConditionsOperation in experiment
68% With titanium(IV) isopropylate; tert.-butylhydroperoxide In dichloromethane; toluene
Reference： [1]Bonini, Carlo; Righi, Giuliana; Sotgiu, Giovanni [Journal of Organic Chemistry, 1991, vol. 56, # 21, p. 6206 - 6209]
  • 9
  • [ 924-41-4 ]
  • [ 6857-93-8 ]
YieldReaction ConditionsOperation in experiment
With chromic acid In diethyl ether at 15℃; for 0.0833333h;
With chromium(VI) oxide; sulfuric acid In water; acetone; benzene at 0℃; for 0.25h;
With chromium(VI) oxide; sulfuric acid In diethyl ether; water for 0.0833333h;
With jones reagent In acetone at 5℃; for 1h;
With sodium dichromate; sulfuric acid In diethyl ether at 20 - 25℃; for 2h;
With Dess-Martin periodane In dichloromethane at 20℃; for 3h;
With Dess-Martin periodane In dichloromethane at 20℃; for 3h;
With silica gel; pyridinium chlorochromate In dichloromethane Inert atmosphere;

Reference： [1]Della, Ernest W.; Elsey, Gordon M.; Skouroumounis, George [Australian Journal of Chemistry, 1990, vol. 43, # 7, p. 1231 - 1244]
[2]Newmann-Evans, Richard H.; Simon, Reyna J.; Carpenter, B. K. [Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 695 - 711]
[3]Dauben, William G.; Cogen, Jeffrey M.; Ganzer, George A.; Behar, Victor [Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5817 - 5824]
[4]Barfield,M.; Brown,S.E.; Canada,E.D. [Journal of the American Chemical Society, 1980, vol. 102, p. 3355]
[5]Della, Ernest W.; Pigou, Paul E. [Australian Journal of Chemistry, 1983, vol. 36, # 11, p. 2261 - 2268]
[6]Lorber, Katja; Schieberle, Peter; Buettner, Andrea [Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 5, p. 1025 - 1031]
[7]Lorber, Katja; Schieberle, Peter; Buettner, Andrea [Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 5, p. 1025 - 1031]
[8]Troadec, Thibault; Wasano, Tatsuya; Lenk, Romaric; Baceiredo, Antoine; Saffon-Merceron, Nathalie; Hashizume, Daisuke; Saito, Yosuke; Nakata, Norio; Branchadell, Vicenç; Kato, Tsuyoshi [Angewandte Chemie - International Edition, 2017, vol. 56, # 24, p. 6891 - 6895][Angew. Chem., 2017, vol. 129, p. 6995 - 6999]
  • 10
  • [ 924-41-4 ]
  • [ 122983-07-7 ]
YieldReaction ConditionsOperation in experiment
86% With chloro-trimethyl-silane; water; sodium iodide In acetonitrile at 20℃; for 1h;
74% With chloro-trimethyl-silane; water; sodium iodide In acetonitrile for 0.5h; Ambient temperature;
Reference： [1]Yen, Yao-Pin; Chen, Jay-Hung [Organic Preparations and Procedures International, 2006, vol. 38, # 5, p. 500 - 504]
[2]Kanai, Takaya; Irifune, Shinji; Ishii, Yasutaka; Ogawa, Masaya [Synthesis, 1989, # 4, p. 283 - 286]
  • 11
  • [ 924-41-4 ]
  • [ 78-39-7 ]
  • [ 90269-57-1 ]
YieldReaction ConditionsOperation in experiment
86% With propionic acid at 144℃; for 2h;
80% With propionic acid at 140℃; for 1.5h;
79% With propionic acid at 145℃; for 3h; Inert atmosphere;
With propionic acid at 139℃;

Reference： [1]Avedissian, Hovsep; Sinna, Santosh C.; Yazbak, Ahmad; Sinha, Anjana; Neogi, Partha; Sinha, Subhash C.; Keinan, Ehud [Journal of Organic Chemistry, 2000, vol. 65, # 19, p. 6035 - 6051]
[2]Chattopadhyay, A.; Mamdapur, V. R. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 169]
[3]Nguyen, Natalie N. M.; Leclere, Mathieu; Stogaitis, Nicole; Fallis, Alex G. [Organic Letters, 2010, vol. 12, # 8, p. 1684 - 1687]
[4]Nagai, Mitsuo; Lazor, Jerome; Wilcox, Craig S. [Journal of Organic Chemistry, 1990, vol. 55, # 11, p. 3440 - 3442]
  • 12
  • [ 924-41-4 ]
  • [ 124-63-0 ]
  • [ 120903-48-2 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine In dichloromethane at -10℃; for 1h;
With pyridine
With triethylamine In dichloromethane at 0℃; for 2h;
Reference： [1]Kasatkin, A. N.; Kulak, A. N.; Tolstikov, G. A.; Lomakina, S. I. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1988, vol. 37, p. 1939 - 1945][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1988, # 9, p. 2159 - 2166]
[2]Bloodworth; Curtis; Spencer; Tallant [Tetrahedron, 1993, vol. 49, # 13, p. 2729 - 2750]
[3]Zhao, Shu-Bin; Bilodeau, Eric; Lemieux, Valerie; Beauchemin, Andre M. [Organic Letters, 2012, vol. 14, # 19, p. 5082 - 5085,4] Zhao, Shu-Bin; Bilodeau, Eric; Lemieux, Valérie; Beauchemin, André M. [Organic Letters, 2012, vol. 14, # 19, p. 5082 - 5085]
  • 13
  • [ 107-05-1 ]
  • [ 107-02-8 ]
  • [ 924-41-4 ]
YieldReaction ConditionsOperation in experiment
88% With copper; tin(ll) chloride In water at 20℃; for 3h;
With magnesium at 0 deg C in THF; Yield given. Multistep reaction;
Reference： [1]Tan, Xiang-Hui; Shen, Bo; Liu, Lei; Guo, Qing-Xiang [Tetrahedron Letters, 2002, vol. 43, # 51, p. 9373 - 9376]
[2]Newmann-Evans, Richard H.; Simon, Reyna J.; Carpenter, B. K. [Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 695 - 711]
  • 14
  • [ 2622-05-1 ]
  • [ 107-02-8 ]
  • [ 924-41-4 ]
YieldReaction ConditionsOperation in experiment
58% In tetrahydrofuran at 0℃; for 1h;
Reference： [1]Dauben, William G.; Cogen, Jeffrey M.; Ganzer, George A.; Behar, Victor [Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5817 - 5824]
  • 15
  • [ 924-41-4 ]
  • [ 5704-66-5 ]
  • [ 126109-95-3 ]
YieldReaction ConditionsOperation in experiment
96% With pyridine In benzene for 0.25h;
Reference： [1]Newmann-Evans, Richard H.; Simon, Reyna J.; Carpenter, B. K. [Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 695 - 711]
  • 16
  • [ 924-41-4 ]
  • [ 78-39-7 ]
  • [ 211927-49-0 ]
YieldReaction ConditionsOperation in experiment
94% With propionic acid
Reference： [1]Fan; Flentke; Rich [Journal of the American Chemical Society, 1998, vol. 120, # 34, p. 8893 - 8894]
  • 17
  • [ 924-41-4 ]
  • [ 79-03-8 ]
  • [ 338799-34-1 ]
YieldReaction ConditionsOperation in experiment
95% With pyridine In dichloromethane at 0℃; for 1.5h;
Reference： [1]Dounay; Forsyth [Organic letters, 2001, vol. 3, # 7, p. 975 - 978] Dounay, Amy B; Florence, Gordon J; Saito, Akira; Forsyth, Craig J [Tetrahedron, 2002, vol. 58, # 10, p. 1865 - 1874]
  • 19
  • [ 924-41-4 ]
  • [ 13412-55-0 ]
  • (R)-1-((R)-3-Trityl-4,5-dihydro-isoxazol-5-yl)-but-3-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: 1,5-hexadiene-3-ol With ethylmagnesium bromide In tetrahydrofuran; benzene at 0℃; for 0.5h; Stage #2: triphenylmethylacetonitrile oxide In tetrahydrofuran; benzene at 0℃; for 3h;
Reference： [1]Kim, Hyoung Cheul; Woo, Seung Woo; Seo, Min Jung; Jeon, Dong Ju; No, Zaesung; Kim, Hyoung Rae [Synlett, 2002, # 10, p. 1691 - 1693]
  • 20
  • [ 924-41-4 ]
  • 2-tert-butyldimethylsilyloxy-2-phenylacetonitrile oxide [ No CAS ]
  • 1-{3-[(<i>tert</i>-butyl-dimethyl-silanyloxy)-phenyl-methyl]-4,5-dihydro-isoxazol-5-yl}-but-3-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: 1,5-hexadiene-3-ol With ethylmagnesium bromide In tetrahydrofuran; benzene at 0℃; for 0.5h; Stage #2: 2-tert-butyldimethylsilyloxy-2-phenylacetonitrile oxide In tetrahydrofuran; benzene at 0℃; for 3h;
Reference： [1]Kim, Hyoung Cheul; Woo, Seung Woo; Seo, Min Jung; Jeon, Dong Ju; No, Zaesung; Kim, Hyoung Rae [Synlett, 2002, # 10, p. 1691 - 1693]
  • 21
  • [ 924-41-4 ]
  • [ 558459-27-1 ]
YieldReaction ConditionsOperation in experiment
42% Stage #1: 1,5-hexadiene-3-ol With titanium(IV) isopropylate; (-)-dicyclohexyl D-tartrate; 4 A molecular sieve In dichloromethane at -20℃; for 0.5h; Stage #2: With tert.-butylhydroperoxide In dichloromethane at -20℃; for 19h;
40% With tert.-butylhydroperoxide; MS 4 Angstroem In dichloromethane
35% With titanium(IV) isopropylate; tert.-butylhydroperoxide; meso-diisopropyl tartrate In dichloromethane at -20℃; for 23h; optical yield given as %ee;
16.25 g With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-dicyclohexyl D-tartrate In dichloromethane at -20℃; for 40h;

Reference： [1]Crimmins, Michael T.; Powell, Mark T. [Journal of the American Chemical Society, 2003, vol. 125, # 25, p. 7592 - 7595]
[2]Fuerstner, Alois; Nagano, Takashi; Mueller, Christoph; Seidel, Guenter; Mueller, Oliver [Chemistry - A European Journal, 2007, vol. 13, # 5, p. 1452 - 1462]
[3]Location in patent: scheme or table Ohmiya, Hirohisa; Yoshida, Mika; Sawamura, Masaya [Synlett, 2010, # 14, p. 2136 - 2140]
[4]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 22
  • [ 924-41-4 ]
  • [ 623-47-2 ]
  • ethyl (E)-3-(1,5-hexadien-3-yl)oxy-2-propenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: propynoic acid ethyl ester With triethylamine In diethyl ether at 20℃; for 0.166667h; Stage #2: 1,5-hexadiene-3-ol In diethyl ether at 20℃; for 48h;
Reference： [1]Hart, David J.; Bennett, Chad E. [Organic Letters, 2003, vol. 5, # 9, p. 1499 - 1502]
  • 23
  • [ 924-41-4 ]
  • [ 784182-27-0 ]
  • [ 784182-28-1 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydride at 50℃; for 0.333333h;
Reference： [1]Maifeld, Sarah V.; Miller, Reagan L.; Lee, Daesung [Journal of the American Chemical Society, 2004, vol. 126, # 39, p. 12228 - 12229]
  • 24
  • [ 924-41-4 ]
  • [ 3019-71-4 ]
  • 1-vinyl-but-3-enyl carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 1,5-hexadiene-3-ol; Trichloroacetyl isocyanate In dichloromethane at 0℃; for 2h; Stage #2: With potassium carbonate In methanol for 4h;
Reference： [1]Donohoe, Timothy J.; Johnson, Peter D.; Pye, Richard J.; Keenan, Martine [Organic Letters, 2004, vol. 6, # 15, p. 2583 - 2585]
  • 25
  • [ 924-41-4 ]
  • [ 79-22-1 ]
  • [ 688318-01-6 ]
YieldReaction ConditionsOperation in experiment
52% With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
With pyridine In dichloromethane at 0℃;
With pyridine In dichloromethane at 20℃;
Reference： [1]Dai, Yijing; Wu, Fan; Zang, Zhenhua; You, Hengzhi; Gong, Hegui [Chemistry - A European Journal, 2012, vol. 18, # 3, p. 808 - 812]
[2]Ito, Hajime; Kawakami, Chika; Sawamura, Masaya [Journal of the American Chemical Society, 2005, vol. 127, # 46, p. 16034 - 16035]
[3]Ashfeld, Brandon L.; Miller, Kenneth A.; Smith, Anna J.; Tran, Kristy; Martin, Stephen F. [Journal of Organic Chemistry, 2007, vol. 72, # 24, p. 9018 - 9031]
  • 26
  • [ 924-41-4 ]
  • [ 98-88-4 ]
  • [ 369596-31-6 ]
YieldReaction ConditionsOperation in experiment
87% With dmap; triethylamine In dichloromethane at 20℃; for 6h;
Reference： [1]Krafft; Sugiura; Abboud [Journal of the American Chemical Society, 2001, vol. 123, # 37, p. 9174 - 9175]
  • 27
  • [ 924-41-4 ]
  • [ 936724-50-4 ]
  • [ 51769-28-9 ]
  • [ 119596-43-9 ]
YieldReaction ConditionsOperation in experiment
With tert.-butylhydroperoxide; (+)-dicyclohexyl tartrate In decane; dichloromethane at -20℃; for 19.5h;
Reference： [1]Hodgson, David M.; Ying, Kit Chung; Nuzzo, Irene; Freixas, Gloria; Kulikiewicz, Krystyna K.; Cleator, Ed; Paris, Jean-Marc [Journal of the American Chemical Society, 2007, vol. 129, # 14, p. 4456 - 4462]
  • 28
  • [ 924-41-4 ]
  • [ 106-96-7 ]
  • [ 182186-66-9 ]
YieldReaction ConditionsOperation in experiment
63% With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran; toluene at 20℃; for 12h;
Reference： [1]Virolleaud, Marie-Alice; Piva, Olivier [European Journal of Organic Chemistry, 2007, # 10, p. 1606 - 1612]
  • 29
  • [ 924-41-4 ]
  • hexa-1,5-dien-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With aminosulfonic acid In N,N-dimethyl-formamide at 50℃;
Reference： [1]Defieber, Christian; Ariger, Martin A.; Moriel, Patricia; Carreira, Erick M. [Angewandte Chemie - International Edition, 2007, vol. 46, # 17, p. 3139 - 3143]
  • 30
  • [ 924-41-4 ]
  • (+)-(2R,3S)-3-tert-butyldimethylsilyloxy-1,2-epoxy-5-hexene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (+)-dicyclohexyl tartrate; t-BuOOH / Ti(i-PrO)4 / CH2Cl2; decane / 19.5 h / -20 °C 2: 1.166 g / imidazole / CH2Cl2 / 5 h / 20 °C
Reference： [1]Hodgson, David M.; Ying, Kit Chung; Nuzzo, Irene; Freixas, Gloria; Kulikiewicz, Krystyna K.; Cleator, Ed; Paris, Jean-Marc [Journal of the American Chemical Society, 2007, vol. 129, # 14, p. 4456 - 4462]
  • 31
  • [ 924-41-4 ]
  • (+)-(2R,3S)-3-tert-butyldimethylsilanyloxybicyclo[3.1.0]hexan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (+)-dicyclohexyl tartrate; t-BuOOH / Ti(i-PrO)4 / CH2Cl2; decane / 19.5 h / -20 °C 2: 1.166 g / imidazole / CH2Cl2 / 5 h / 20 °C 3: 61 percent / lithium 2,2,6,6-tetramethylpiperidide / various solvent(s); hexane / 16 h / 20 °C
Reference： [1]Hodgson, David M.; Ying, Kit Chung; Nuzzo, Irene; Freixas, Gloria; Kulikiewicz, Krystyna K.; Cleator, Ed; Paris, Jean-Marc [Journal of the American Chemical Society, 2007, vol. 129, # 14, p. 4456 - 4462]
  • 32
  • [ 924-41-4 ]
  • [ 143120-38-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 20 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 92 percent / NaBH4 / tetrahydrofuran; H2O / 0 - 20 °C 9.1: 96 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 12 h / 40 °C 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C 15.1: NaN(SiMe3)2; HMPA / tetrahydrofuran; toluene / -65 °C 15.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C 16.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh3)4 / tetrahydrofuran / 0 - 20 °C 17.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 18.1: 74 percent / CCl4; 1-methyl-1-cyclohexene; benzyl triethylammonium chloride / trioctylphosphine / toluene / 2.5 h / 80 °C 19.1: 92 percent / DDQ; H2O / 1,2-dichloro-ethane / 1 h / 50 °C 20.1: 54 percent / CBr4; 1-methyl-1-cyclohexene; trioctyl phosphine / toluene / 1 h / 70 °C
Multi-step reaction with 20 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 95 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 40 °C 9.1: NaBH4 / tetrahydrofuran; H2O 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C 15.1: NaN(SiMe3)2; HMPA / tetrahydrofuran; toluene / -65 °C 15.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C 16.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh3)4 / tetrahydrofuran / 0 - 20 °C 17.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 18.1: 74 percent / CCl4; 1-methyl-1-cyclohexene; benzyl triethylammonium chloride / trioctylphosphine / toluene / 2.5 h / 80 °C 19.1: 92 percent / DDQ; H2O / 1,2-dichloro-ethane / 1 h / 50 °C 20.1: 54 percent / CBr4; 1-methyl-1-cyclohexene; trioctyl phosphine / toluene / 1 h / 70 °C
Reference： [1]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
[2]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 33
  • [ 924-41-4 ]
  • [ 333788-88-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 19 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 92 percent / NaBH4 / tetrahydrofuran; H2O / 0 - 20 °C 9.1: 96 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 12 h / 40 °C 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C 15.1: NaN(SiMe3)2; HMPA / tetrahydrofuran; toluene / -65 °C 15.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C 16.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh3)4 / tetrahydrofuran / 0 - 20 °C 17.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 18.1: 74 percent / CCl4; 1-methyl-1-cyclohexene; benzyl triethylammonium chloride / trioctylphosphine / toluene / 2.5 h / 80 °C 19.1: 92 percent / DDQ; H2O / 1,2-dichloro-ethane / 1 h / 50 °C
Multi-step reaction with 19 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 95 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 40 °C 9.1: NaBH4 / tetrahydrofuran; H2O 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C 15.1: NaN(SiMe3)2; HMPA / tetrahydrofuran; toluene / -65 °C 15.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C 16.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh3)4 / tetrahydrofuran / 0 - 20 °C 17.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 18.1: 74 percent / CCl4; 1-methyl-1-cyclohexene; benzyl triethylammonium chloride / trioctylphosphine / toluene / 2.5 h / 80 °C 19.1: 92 percent / DDQ; H2O / 1,2-dichloro-ethane / 1 h / 50 °C
Reference： [1]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
[2]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 34
  • [ 924-41-4 ]
  • [ 333788-76-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 18 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 92 percent / NaBH4 / tetrahydrofuran; H2O / 0 - 20 °C 9.1: 96 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 12 h / 40 °C 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C 15.1: NaN(SiMe3)2; HMPA / tetrahydrofuran; toluene / -65 °C 15.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C 16.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh3)4 / tetrahydrofuran / 0 - 20 °C 17.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 18.1: 74 percent / CCl4; 1-methyl-1-cyclohexene; benzyl triethylammonium chloride / trioctylphosphine / toluene / 2.5 h / 80 °C
Multi-step reaction with 18 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 95 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 40 °C 9.1: NaBH4 / tetrahydrofuran; H2O 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C 15.1: NaN(SiMe3)2; HMPA / tetrahydrofuran; toluene / -65 °C 15.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C 16.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh3)4 / tetrahydrofuran / 0 - 20 °C 17.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C 18.1: 74 percent / CCl4; 1-methyl-1-cyclohexene; benzyl triethylammonium chloride / trioctylphosphine / toluene / 2.5 h / 80 °C
Reference： [1]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
[2]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 35
  • [ 924-41-4 ]
  • [ 333788-75-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 17 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 92 percent / NaBH4 / tetrahydrofuran; H2O / 0 - 20 °C 9.1: 96 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 12 h / 40 °C 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C 15.1: NaN(SiMe3)2; HMPA / tetrahydrofuran; toluene / -65 °C 15.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C 16.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh3)4 / tetrahydrofuran / 0 - 20 °C 17.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C
Multi-step reaction with 17 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 95 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 40 °C 9.1: NaBH4 / tetrahydrofuran; H2O 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C 15.1: NaN(SiMe3)2; HMPA / tetrahydrofuran; toluene / -65 °C 15.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C 16.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh3)4 / tetrahydrofuran / 0 - 20 °C 17.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C
Reference： [1]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
[2]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 36
  • [ 924-41-4 ]
  • [ 600728-61-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 92 percent / NaBH4 / tetrahydrofuran; H2O / 0 - 20 °C 9.1: 96 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 12 h / 40 °C 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C
Multi-step reaction with 10 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 95 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 40 °C 9.1: NaBH4 / tetrahydrofuran; H2O 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C
Reference： [1]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
[2]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 37
  • [ 924-41-4 ]
  • [ 600728-59-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 92 percent / NaBH4 / tetrahydrofuran; H2O / 0 - 20 °C 9.1: 96 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 12 h / 40 °C
Multi-step reaction with 9 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 95 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 40 °C 9.1: NaBH4 / tetrahydrofuran; H2O
Reference： [1]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
[2]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 38
  • [ 924-41-4 ]
  • [ 600728-69-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 92 percent / NaBH4 / tetrahydrofuran; H2O / 0 - 20 °C 9.1: 96 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 12 h / 40 °C 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C
Multi-step reaction with 14 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 95 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 40 °C 9.1: NaBH4 / tetrahydrofuran; H2O 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C 14.1: 97 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 15 °C
Reference： [1]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
[2]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 39
  • [ 924-41-4 ]
  • (R)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 92 percent / NaBH4 / tetrahydrofuran; H2O / 0 - 20 °C 9.1: 96 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 12 h / 40 °C 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C
Multi-step reaction with 13 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 95 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 40 °C 9.1: NaBH4 / tetrahydrofuran; H2O 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C
Reference： [1]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
[2]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 40
  • [ 924-41-4 ]
  • [ 600728-63-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 92 percent / NaBH4 / tetrahydrofuran; H2O / 0 - 20 °C 9.1: 96 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 12 h / 40 °C 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C
Multi-step reaction with 13 steps 1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH2Cl2 / 40 h / -20 °C 2.1: PPTS / 0 - 20 °C 2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C 3.1: 94 percent / KH; Bu4NI / tetrahydrofuran / 3 h / 0 - 20 °C 4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C 5.1: NaH / tetrahydrofuran / 1 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C 6.1: pivaloyl chloride; Et3N / tetrahydrofuran / -78 - 0 °C 6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 7.1: NaN(SiMe3)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C 7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C 8.1: 95 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 40 °C 9.1: NaBH4 / tetrahydrofuran; H2O 10.1: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 5 °C 11.1: TiCl4; (-)-sparteine; N-methylpyrroldinone / CH2Cl2 / 0.33 h / 0 °C 11.2: 92 percent / CH2Cl2 / 1 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 13.1: 0.370 g / NaBH4 / tetrahydrofuran; H2O / 43 h / 20 °C
Reference： [1]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
[2]Crimmins, Michael T.; DeBaillie, Amy C. [Organic Letters, 2003, vol. 5, # 17, p. 3009 - 3011]
  • 41
  • [ 924-41-4 ]
  • [ 17159-75-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium dichromate dihydrate, conc. H2SO4 / diethyl ether / 2 h / 20 - 25 °C 2: 10 h / Irradiation 3: zinc iodide / 0.17 h 4: 77 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 5: NaNO2, 10percent acetic acid / other 1-substituted bicyclo<2.1.1>hexan-2-ones
Reference： [1]Della, Ernest W.; Pigou, Paul E. [Australian Journal of Chemistry, 1983, vol. 36, # 11, p. 2261 - 2268]
  • 42
  • [ 924-41-4 ]
  • [ 4101-68-2 ]
  • 3-(10-bromodecyloxy)-1,5-hexadiene [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% In tetrahydrofuran 1.1 1) 1) Synthesis of 3-(10-bromodecyloxy)-1,5-hexadiene [Compound (1)] STR13 10 g of 1,5-hexadien-3-ol was dissolved in 100 ml of tetrahydrofuran (THF), and the atmosphere was replaced with argon. 4.1 g of 60% sodium hydride was added little by little. After hydrogen gas had ceased to generate, a THF solution of 75 g of 1,10-dibromodecane was added, and reflux was carried out for 8 hours. The insoluble matter generated was filtered off, and the solvent was evaporated. The residue was purified by column chromatography, to obtain 11.3 g of the objective compound (1). (Yield: 35%).
Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - US5437816, 1995, A
  • 43
  • [ 924-41-4 ]
  • [ 107-02-8 ]
  • [ 1730-25-2 ]
  • [ 189440-77-5 ]
YieldReaction ConditionsOperation in experiment
With propionic acid In Trimethyl orthoacetate; tert-butyl methyl ether 1 Example 1 Example 1 78.0 g (about 0.71 mol) of 1,5-hexadien-3-ol, obtained by a Grignard reaction from allylmagnesium bromide and acrolein, were dissolved in 198.0 g (1.65 mol) of trimethyl orthoacetate and 3.0 g (0.04 mol) of propionic acid were then added. The reaction mixture was heated to 120° C. and the methanol formed during the reaction was distilled off over a 15 cm Widmer column. After 2 hours, the reaction mixture was held at 130° C. for a further 1 hour to complete the reaction and was then cooled to room temperature, diluted with 500 ml of tert-butyl methyl ether and the solution was washed twice with 100 ml of saturated sodium bicarbonate solution, dried with sodium sulphate and concentrated. Distillation of the resulting 128 g of crude product over a 20 cm Widmer column gave 51.6 g of olfactorily good methyl (E)-4,7-octadienoate of boiling point 76° C./17 mbar and with a purity of about 98%. Spectral data of the thus-prepared methyl (E)-4,7-octa-dienoate: NMR (200 MHz, CDCl3): 2.38 (m,4H); 2.73 (m,2H); 3.68 (s,3H); 4.97-5.07 (m,2H); 5.45 (m,2H); 5.70-5.90 (m,1H). Mass spectrum: 154 (M+, 1), 122(6), 95 (23), 94 (36), 81 (36), 80 (89), 79 (100), 74 (38), 71 (14), 67 (34), 59 (24), 53 (30), 43 (46), 41 (64), 39 (49).
Reference： [1]Current Patent Assignee: GIVAUDAN SA - US5837671, 1998, A
  • 44
  • [ 1445-45-0 ]
  • [ 924-41-4 ]
  • [ 189440-77-5 ]
YieldReaction ConditionsOperation in experiment
88% With propionic acid In 5,5-dimethyl-1,3-cyclohexadiene at 135℃; for 18h;
Reference： [1]Location in patent: experimental part Emmanuvel, Lourdusamy; Kamble, Dayanand A.; Sudalai, Arumugam [Tetrahedron Asymmetry, 2009, vol. 20, # 1, p. 84 - 88]
  • 45
  • [ 6044-68-4 ]
  • [ 924-41-4 ]
  • 5-vinyl-2-cyclopenten-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 1,5-hexadiene-3-ol With C20H17ClPdSe2; water; toluene-4-sulfonic acid; bis(pinacol)diborane In methanol; dimethyl sulfoxide at 50℃; for 16h; Stage #2: 3,3-dimethoxyprop-1-ene In methanol; dichloromethane; dimethyl sulfoxide for 6h; Stage #3: With Hoveyda-Grubbs catalyst second generation In dichloromethane for 4h; Inert atmosphere; Reflux;
Reference： [1]Location in patent: experimental part Selander, Nicklas; Szabo, Kalman J. [Advanced Synthesis and Catalysis, 2008, vol. 350, # 13, p. 2045 - 2051]
  • 46
  • [ 924-41-4 ]
  • [ 2100-17-6 ]
  • cis-2-allylcyclohex-3-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 1,5-hexadiene-3-ol; 4-pentenal With C20H17ClPdSe2; water; toluene-4-sulfonic acid; bis(pinacol)diborane In methanol; dimethyl sulfoxide at 50℃; for 20h; Stage #2: With Hoveyda-Grubbs catalyst second generation In methanol; dichloromethane; dimethyl sulfoxide for 2h; Inert atmosphere; Reflux;
Reference： [1]Location in patent: experimental part Selander, Nicklas; Szabo, Kalman J. [Advanced Synthesis and Catalysis, 2008, vol. 350, # 13, p. 2045 - 2051]
  • 47
  • [ 924-41-4 ]
  • [ 100-52-7 ]
  • (3E)-1-phenyl-3,6-heptadien-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With [Pd(CH3CN)(C6H3(CH2SCH3)2)](1+)*BF4(1-)=[Pd(CH3CN)(C6H3(CH2SCH3)2)]BF4; water; toluene-4-sulfonic acid; bis(pinacol)diborane In chloroform at 50℃; for 18h; regioselective reaction;
Reference： [1]Selander, Nicklas; Szabo, Kalman J. [Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5695 - 5698]
  • 48
  • [ 924-41-4 ]
  • [ 110046-51-0 ]
  • [ 1217816-09-5 ]
YieldReaction ConditionsOperation in experiment
99% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 6h; Inert atmosphere; Sealed vessel;
Reference： [1]Location in patent: experimental part Cros, Fanny; Pelotier, Beatrice; Piva, Olivier [Synthesis, 2010, # 2, p. 233 - 238]
  • 49
  • [ 799296-23-4 ]
  • [ 924-41-4 ]
  • C12H18O [ No CAS ]
  • [ 1202570-26-0 ]
YieldReaction ConditionsOperation in experiment
62% With bromopentacarbonylmanganese(I) In dichloromethane at 20℃; for 2h;
Reference： [1]Location in patent: experimental part Scott, Colleen N.; Wilcox, Craig S. [Journal of Organic Chemistry, 2010, vol. 75, # 1, p. 253 - 256]
  • 50
  • [ 625-38-7 ]
  • [ 924-41-4 ]
  • [ 1253384-28-9 ]
YieldReaction ConditionsOperation in experiment
92% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;
Reference： [1]Location in patent: experimental part Cros, Fanny; Pelotier, Beatrice; Piva, Olivier [European Journal of Organic Chemistry, 2010, # 26, p. 5063 - 5070]
  • 51
  • [ 924-41-4 ]
  • [ 6773-29-1 ]
  • dimethyl 2-(hexa-1,5-dien-3-yloxy)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With dirhodium tetraacetate In benzene at 60℃; for 2h;
Reference： [1]Chany, Anne-Caroline; Marx, Léo B.; Burton, Jonathan W. [Organic and Biomolecular Chemistry, 2015, vol. 13, # 35, p. 9190 - 9193]
  • 52
  • [ 924-41-4 ]
  • [ 7677-24-9 ]
  • C14H14N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole-2-yl)cyclopropane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; copper(II) bis(trifluoromethanesulfonate) In N,N-dimethyl acetamide; acetonitrile at 23℃; Irradiation; regioselective reaction;
Reference： [1]Zhang, Zuxiao; Ngo, Duong T.; Nagib, David A. [ACS Catalysis, 2021, vol. 11, # 6, p. 3473 - 3477]

Tags: 924-41-4 synthesis path| 924-41-4 SDS| 924-41-4 COA| 924-41-4 purity| 924-41-4 application| 924-41-4 NMR| 924-41-4 COA| 924-41-4 structure

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