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8-Nonynoicacid
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[ CAS No. 30964-01-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
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Product Details of [ 30964-01-3 ]

CAS No. :30964-01-3 MDL No. :MFCD00671368
Formula : C9H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NLRIJHGYFNZMGB-UHFFFAOYSA-N
M.W : 154.21 Pubchem ID :35698
Synonyms :

Safety of [ 30964-01-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 30964-01-3 ]

* 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 [ 30964-01-3 ]

[ 30964-01-3 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 67-56-1 ]
  • [ 30964-01-3 ]
  • [ 7003-48-7 ]
YieldReaction ConditionsOperation in experiment
100% With toluene-4-sulfonic acid for 3h; Heating;
88% With 4 A molecular sieve; sulfuric acid for 18h; Heating;
86.2% With sulfuric acid for 4h; Heating;
With toluene-4-sulfonic acid
2.50 g With thionyl chloride
With sulfuric acid

Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
[2]Newton, Roger F.; Pauson, Peter L.; Taylor, Ronald G. [Journal of Chemical Research, Miniprint, 1980, # 9, p. 3501 - 3522]
[3]Ranganathan, S.; Maniktala, Vibha; Kumar, Raaj; Singh, G. P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 12, p. 1197 - 1207]
[4]Wotiz; Hudak [Journal of Organic Chemistry, 1954, vol. 19, p. 1580,1587]
[5]Trost; Pinkerton [Organic letters, 2000, vol. 2, # 11, p. 1601 - 1603]
[6]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
[7]Location in patent: body text Bekish, Andrei V. [Tetrahedron Letters, 2012, vol. 53, # 24, p. 3082 - 3085]
  • 2
  • [ 7003-48-7 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In ethanol for 0.5h; Heating; Yield given;
With potassium hydroxide for 0.5h; Heating;
Reference： [1]Wotiz; Buco [Journal of Organic Chemistry, 1955, vol. 20, p. 210,213]
[2]Nakatani, Munehiro; Yamachika, Takashi; Tanoue, Takao; Hase, Tsunao [Phytochemistry, 1985, vol. 24, # 1, p. 39 - 42]
[3]Nakatani; Fukunaga; Haraguchi; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539]
  • 3
  • [ 30964-01-3 ]
  • [ 90675-38-0 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride
With thionyl chloride In benzene for 2h; Heating;
With oxalyl dichloride In dichloromethane
Reference： [1]Bergel'son,L.D. et al. [Journal of general chemistry of the USSR, 1962, vol. 32, p. 57 - 62][Zhurnal Obshchei Khimii, 1962, vol. 32, # 1, p. 58 - 64]
[2]Ranganathan, Darshan; Haridas; Vaish, Narendra K.; Madhusudanan; Roy, Raja; Balasubramanian; Srinivas [Journal of the Indian Chemical Society, 1998, vol. 75, # 10-12, p. 598 - 600]
[3]Wang, Guijun; Cheuk, Sherwin; Williams, Kristopher; Sharma, Vibha; Dakessian, Lousi; Thorton, Zeus [Carbohydrate Research, 2006, vol. 341, # 6, p. 705 - 716]
  • 4
  • [ 908094-01-9 ]
  • [ 30964-01-3 ]
  • [ 7003-48-7 ]
YieldReaction ConditionsOperation in experiment
86% In diethyl ether for 0.0833333h; Cooling with ice;
In diethyl ether
Reference： [1]Kobayashi, Yuichi; Morita, Masao; Ogawa, Narihito; Kondo, Daiki; Tojo, Toshifumi [Organic and Biomolecular Chemistry, 2016, vol. 14, # 45, p. 10667 - 10673]
[2]Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice; Bardy, Andre; Comet, Michel; Vidal, Michel [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55]
  • 5
  • [ 64-17-5 ]
  • [ 30964-01-3 ]
  • [ 108545-40-0 ]
YieldReaction ConditionsOperation in experiment
74% With sulfuric acid Heating;
Reference： [1]Nakatani; Fukunaga; Haraguchi; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539]
  • 7
  • [ 30515-28-7 ]
  • [ 1216963-74-4 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
41% In dimethyl sulfoxide for 2h; Ambient temperature;
In dimethyl sulfoxide 1) 0 deg C, 1 h, 2) up to room temp.; Yield given;
In dimethyl sulfoxide
In dimethyl sulfoxide at 20℃;

Reference： [1]Singh, Alok; Schnur, Joel M. [Synthetic Communications, 1986, vol. 16, # 7, p. 847 - 852]
[2]Newton, Roger F.; Pauson, Peter L.; Taylor, Ronald G. [Journal of Chemical Research, Miniprint, 1980, # 9, p. 3501 - 3522]
[3]Rousseau, Gérard; Strzalko, Tekla; Roux, Marie-Claude [Tetrahedron Letters, 2004, vol. 45, # 23, p. 4503 - 4505]
[4]Kaspersen, Mads Holmgaard; Jenkins, Laura; Dunlop, Julia; Milligan, Graeme; Ulven, Trond [MedChemComm, 2017, vol. 8, # 6, p. 1360 - 1365]
  • 8
  • [ 30964-01-3 ]
  • [ 39178-65-9 ]
  • [ 36168-17-9 ]
YieldReaction ConditionsOperation in experiment
86% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In diethylamine for 3h; Ambient temperature;
Reference： [1]Haviv; Ratajczyk; DeNet; Martin; Dyer; Carter [Journal of Medicinal Chemistry, 1987, vol. 30, # 2, p. 254 - 263]
  • 9
  • [ 30964-01-3 ]
  • C3(13)C2H11Br [ No CAS ]
  • C12(13)C2H24O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide
Reference： [1]Menger, F. M.; Dulany, M. A.; Carnahan, D. W.; Lee, L. H. [Journal of the American Chemical Society, 1987, vol. 109, # 22, p. 6899 - 6900]
  • 10
  • [ 30964-01-3 ]
  • [ 10160-28-8 ]
YieldReaction ConditionsOperation in experiment
81% With lithium aluminium tetrahydride In diethyl ether for 1h; Heating;
Multi-step reaction with 2 steps 1: diethyl ether 2: LiAlH4 / diethyl ether / 2 h / 0 °C
Multi-step reaction with 2 steps 1: 86.2 percent / conc.H2SO4 / 4 h / Heating 2: 96 percent / LAH / diethyl ether / 2 h / Ambient temperature
Reference： [1]Zakharkin, L. I.; Petrushkina, E. A. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 1, p. 37 - 41][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 1, p. 42 - 48]
[2]Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice; Bardy, Andre; Comet, Michel; Vidal, Michel [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55]
[3]Ranganathan, S.; Maniktala, Vibha; Kumar, Raaj; Singh, G. P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 12, p. 1197 - 1207]
  • 11
  • [ 20731-23-1 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; bromine 1) CCl4, r.t., 2) 135-145 deg C, 4 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 2: aq. KOH / 0.5 h / Heating
Multi-step reaction with 2 steps 2: 30percent KOH / ethanol / 0.5 h / Heating
Reference： [1]Ranganathan, S.; Maniktala, Vibha; Kumar, Raaj; Singh, G. P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 12, p. 1197 - 1207]
[2]Nakatani; Fukunaga; Haraguchi; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539]
[3]Nakatani, Munehiro; Yamachika, Takashi; Tanoue, Takao; Hase, Tsunao [Phytochemistry, 1985, vol. 24, # 1, p. 39 - 42]
  • 12
  • [ 30964-01-3 ]
  • [ 67-63-0 ]
  • 8-nonynoic acid isopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With sulfuric acid Heating;
Reference： [1]Nakatani; Fukunaga; Haraguchi; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539]
  • 13
  • [ 821-57-8 ]
  • [ 70277-75-7 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
73% In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 1) 20 deg C, 12 h, 2) 40 deg C, 5 h;
Reference： [1]Zakharkin, L. I.; Petrushkina, E. A. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 1, p. 37 - 41][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 1, p. 42 - 48]
  • 14
  • [ 30964-01-3 ]
  • [ 41206-19-3 ]
  • [ 33128-26-6 ]
YieldReaction ConditionsOperation in experiment
66% With sodium hydroxide; copper(l) iodide; hydroxylamine hydrochloride In methanol for 0.75h;
With sodium hydroxide; hydroxylamine hydrochloride; triethylamine; copper(l) chloride In methanol
Reference： [1]Jie, Marcel S. F. Lie Ken; Cheung, Y. K. [Journal of Chemical Research, Miniprint, 1993, # 10, p. 2745 - 2778]
[2]Jie, Marcel S. F. Lie Ken; Chau, Sherman H. [Journal of Chemical Research, Miniprint, 1995, # 11, p. 2642 - 2657]
  • 15
  • [ 617-86-7 ]
  • [ 30964-01-3 ]
  • (E)-9-Triethylsilanyl-non-8-enoic acid [ No CAS ]
  • 8-(triethylsilyl)-8-nonenoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane for 1h; Title compound not separated from byproducts.;
Reference： [1]Trost; Ball [Journal of the American Chemical Society, 2001, vol. 123, # 50, p. 12726 - 12727]
  • 16
  • non-8-ynoic acid 3-methyl-but-2-enyl ester [ No CAS ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
95% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃;
Reference： [1]Nishizawa, Mugio; Yamamoto, Hirofumi; Seo, Ken; Imagawa, Hiroshi; Sugihara, Takumichi [Organic Letters, 2002, vol. 4, # 11, p. 1947 - 1949]
  • 17
  • [ 30964-01-3 ]
  • 9-iodo-8-nonenoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: non-8-ynoic acid With indium(III) chloride; triethyl borane; diisobutylaluminium hydride In tetrahydrofuran; hexane at -78℃; Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; Further stages.;
Reference： [1]Takami, Kazuaki; Yorimitsu, Hideki; Oshima, Koichiro [Organic Letters, 2002, vol. 4, # 17, p. 2993 - 2995]
  • 18
  • [ 30964-01-3 ]
  • (Z)-9-iodo-8-nonenoic acid [ No CAS ]
  • 9-iodo-8-nonenoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: non-8-ynoic acid With triethyl borane; dichloroindium hydride In tetrahydrofuran; hexane at -78℃; for 2.5h; Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; Title compound not separated from byproducts;
Reference： [1]Takami, Kazuaki; Mikami, Satoshi; Yorimitsu, Hideki; Shinokubo, Hiroshi; Oshima, Koichiro [Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6627 - 6631]
  • 19
  • [ 617-86-7 ]
  • [ 30964-01-3 ]
  • 8-(triethylsilyl)-8-nonenoic acid [ No CAS ]
  • (E)-9-triethylsilylnon-8-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In dichloromethane at 0 - 20℃;
1: 72% 2: 3% With [(norbornadiene)rhodium(I)chloride]2; bis(diphenylphosphino)propane; sodium dodecyl-sulfate In water at 20℃; for 3h;
Reference： [1]Trost, Barry M.; Ball, Zachary T. [Journal of the American Chemical Society, 2005, vol. 127, # 50, p. 17644 - 17655]
[2]Sato, Akinori; Kinoshita, Hidenori; Shinokubo, Hiroshi; Oshima, Koichiro [Organic Letters, 2004, vol. 6, # 13, p. 2217 - 2220]
  • 20
  • [ 30964-01-3 ]
  • [ 1119-51-3 ]
  • [ 718598-72-2 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide
Reference： [1]Rousseau, Gérard; Strzalko, Tekla; Roux, Marie-Claude [Tetrahedron Letters, 2004, vol. 45, # 23, p. 4503 - 4505]
  • 21
  • [ 912275-84-4 ]
  • [ 30964-01-3 ]
  • 3,4,5-tris-dodecyloxy-<i>N</i>-(2-non-8-ynoylamino-ethyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃;
Reference： [1]Fujita, Norifumi; Sakamoto, Yoshimine; Shirakawa, Michihiro; Ojima, Masayoshi; Fujii, Akihiko; Ozaki, Masanori; Shinkai, Seiji [Journal of the American Chemical Society, 2007, vol. 129, # 14, p. 4134 - 4135]
  • 22
  • [ 10160-28-8 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
71% With chromium(VI) oxide; sulfuric acid In water; acetone at 0℃; for 0.333333h;
With chromium(VI) oxide; sulfuric acid In water; acetone at 25℃;
With Jones reagent In acetone at 0 - 20℃; for 8h;
Reference： [1]Kobayashi, Yuichi; Morita, Masao; Ogawa, Narihito; Kondo, Daiki; Tojo, Toshifumi [Organic and Biomolecular Chemistry, 2016, vol. 14, # 45, p. 10667 - 10673]
[2]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
[3]Theeramunkong; Galli; Grolla; Caldarelli; Travelli; Massarotti; Troiani; Alisi; Orsomando; Genazzani; Tron [MedChemComm, 2015, vol. 6, # 10, p. 1891 - 1897]
[4]Brooks, Jacob T.; Claridge, Shelley A.; Davis, Tyson C.; Hayes, Tyler R.; Shi, Anni; Singh, Anamika; Villarreal, Terry A. [Angewandte Chemie - International Edition, 2021, vol. 60, # 48, p. 25436 - 25444][Angew. Chem., 2021, vol. 133, # 48, p. 25640 - 25648]
  • 23
  • [ 5921-73-3 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethylenediamine; sodium hydride / 60 °C 2: chromium(VI) oxide; sulfuric acid / acetone; water / 25 °C
Reference： [1]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
[2]Theeramunkong; Galli; Grolla; Caldarelli; Travelli; Massarotti; Troiani; Alisi; Orsomando; Genazzani; Tron [MedChemComm, 2015, vol. 6, # 10, p. 1891 - 1897]
  • 24
  • [ 30964-01-3 ]
  • methyl octadecen-10,12,14,16-tetraen-8-ynoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2.50 g / SOCl2 2: 87 percent / diethylamine; CuI / [Pd(PPh3)2Cl2] / tetrahydrofuran / 3 h / 20 °C
Reference： [1]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
  • 25
  • [ 30964-01-3 ]
  • methyl 15-phenylpentadeca-10,12,14-trien-8-ynoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2.50 g / SOCl2 2: 80 percent / diethylamine; CuI / [Pd(PPh3)2Cl2] / tetrahydrofuran / 3 h / 20 °C
Reference： [1]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
  • 26
  • [ 30964-01-3 ]
  • C19H28O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2.50 g / SOCl2 2: 87 percent / diethylamine; CuI / [Pd(PPh3)2Cl2] / tetrahydrofuran / 3 h / 20 °C 3: zinc; Cu(OAc)2*H2O; AgNO3 / aq. methanol / 24 h / 20 °C
Reference： [1]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
  • 27
  • [ 30964-01-3 ]
  • methyl 15-phenylpentadeca-8,10,12,14-tetraenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2.50 g / SOCl2 2: 80 percent / diethylamine; CuI / [Pd(PPh3)2Cl2] / tetrahydrofuran / 3 h / 20 °C 3: zinc; Cu(OAc)2*H2O; AgNO3 / aq. methanol / 24 h / 20 °C
Reference： [1]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
  • 28
  • [ 30964-01-3 ]
  • methyl 15-phenylpentadeca-8,10,12,14-tetraenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2.50 g / SOCl2 2: 80 percent / diethylamine; CuI / [Pd(PPh3)2Cl2] / tetrahydrofuran / 3 h / 20 °C 3: zinc; Cu(OAc)2*H2O; AgNO3 / aq. methanol / 24 h / 20 °C
Reference： [1]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
  • 29
  • [ 30964-01-3 ]
  • [ 944394-95-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 2.50 g / SOCl2 2: 87 percent / diethylamine; CuI / [Pd(PPh3)2Cl2] / tetrahydrofuran / 3 h / 20 °C 3: zinc; Cu(OAc)2*H2O; AgNO3 / aq. methanol / 24 h / 20 °C 4: 78 mg / iodine / hexane / 0.25 h / Heating
Reference： [1]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
  • 30
  • [ 30964-01-3 ]
  • all-(E)-octadeca-8,10,12,14,16-pentaenoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 2.50 g / SOCl2 2: 87 percent / diethylamine; CuI / [Pd(PPh3)2Cl2] / tetrahydrofuran / 3 h / 20 °C 3: zinc; Cu(OAc)2*H2O; AgNO3 / aq. methanol / 24 h / 20 °C 4: 78 mg / iodine / hexane / 0.25 h / Heating 5: 95 percent / KOH / ethanol / 4 h / 20 °C
Reference： [1]Quesada, Ernesto; Delgado, Javier; Hornillos, Valentin; Acuna, A. Ulises; Amat-Guerri, Francisco [European Journal of Organic Chemistry, 2007, # 14, p. 2285 - 2295]
  • 31
  • [ 30964-01-3 ]
  • [ 30689-78-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 62 percent / 1) LiNH2 / 1) liq. NH3 - THF, -40 deg C, 2) THF - HMPT, 40 deg C, 3 h 3: 90 percent / H2 / 5percent Pd/BaSO4 - quinoline / methanol / Ambient temperature
Reference： [1]Zakharkin, L. I.; Petrushkina, E. A. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 1, p. 37 - 41][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 1, p. 42 - 48]
  • 32
  • [ 30964-01-3 ]
  • [ 56941-92-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 62 percent / 1) LiNH2 / 1) liq. NH3 - THF, -40 deg C, 2) THF - HMPT, 40 deg C, 3 h 3: 85 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 50 h / 140 °C
Reference： [1]Zakharkin, L. I.; Petrushkina, E. A. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 1, p. 37 - 41][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 1, p. 42 - 48]
  • 33
  • [ 30964-01-3 ]
  • [ 64566-18-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 62 percent / 1) LiNH2 / 1) liq. NH3 - THF, -40 deg C, 2) THF - HMPT, 40 deg C, 3 h
Reference： [1]Zakharkin, L. I.; Petrushkina, E. A. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 1, p. 37 - 41][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 1, p. 42 - 48]
  • 34
  • [ 30964-01-3 ]
  • methyl 4,6-O-benzylidene-2-O-(8-nonynoyl)-α-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (COCl)2 / CH2Cl2 2: 38.4 percent / pyridine / CH2Cl2 / 24 h / 20 °C
Reference： [1]Wang, Guijun; Cheuk, Sherwin; Williams, Kristopher; Sharma, Vibha; Dakessian, Lousi; Thorton, Zeus [Carbohydrate Research, 2006, vol. 341, # 6, p. 705 - 716]
  • 35
  • [ 30964-01-3 ]
  • methyl 4,6-O-benzylidene-3-O-(8-nonynoyl)-α-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (COCl)2 / CH2Cl2 2: 15.2 percent / pyridine / CH2Cl2 / 24 h / 20 °C
Reference： [1]Wang, Guijun; Cheuk, Sherwin; Williams, Kristopher; Sharma, Vibha; Dakessian, Lousi; Thorton, Zeus [Carbohydrate Research, 2006, vol. 341, # 6, p. 705 - 716]
  • 36
  • [ 30964-01-3 ]
  • methyl 4,6-O-benzylidene-2,3-di-O-(8-nonynoyl)-α-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (COCl)2 / CH2Cl2 2: 9.6 percent / pyridine / CH2Cl2 / 24 h / 20 °C
Reference： [1]Wang, Guijun; Cheuk, Sherwin; Williams, Kristopher; Sharma, Vibha; Dakessian, Lousi; Thorton, Zeus [Carbohydrate Research, 2006, vol. 341, # 6, p. 705 - 716]
  • 37
  • [ 30964-01-3 ]
  • 14-iodo-oxacyclopentadec-9-yn-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide 2: 7 percent / (biscollidine)iodine(I) hexafluorophosphate / CH2Cl2 / 20 °C
Reference： [1]Rousseau, Gérard; Strzalko, Tekla; Roux, Marie-Claude [Tetrahedron Letters, 2004, vol. 45, # 23, p. 4503 - 4505]
  • 38
  • [ 30964-01-3 ]
  • 14-iodomethyl-oxacyclotetradec-9-yn-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide 2: 14 percent / (biscollidine)iodine(I) hexafluorophosphate / CH2Cl2 / 20 °C
Reference： [1]Rousseau, Gérard; Strzalko, Tekla; Roux, Marie-Claude [Tetrahedron Letters, 2004, vol. 45, # 23, p. 4503 - 4505]
  • 39
  • [ 30964-01-3 ]
  • 12-oxo-octadec-8-enoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C 3: 15 mg / CrCl2; NiCl2 / dimethylformamide / 20 °C
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
  • 40
  • [ 30964-01-3 ]
  • [ 101650-78-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / pyridinium dichromate / CH2Cl2 / 1 h / 0 °C 5: 83 percent / H2 / Pd/C / methanol / 20 °C / 760.05 Torr
Multi-step reaction with 5 steps 2: 70 percent / LiBr; SnBr4; CpRu(CH3CN)3PF6 / acetone / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / PDC / CH2Cl2 / 0 °C 5: 83 percent / H2 / Pd/C / methanol / 20 °C
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
[2]Trost; Pinkerton [Organic letters, 2000, vol. 2, # 11, p. 1601 - 1603]
  • 41
  • [ 30964-01-3 ]
  • [ 37678-05-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / pyridinium dichromate / CH2Cl2 / 1 h / 0 °C
Multi-step reaction with 4 steps 2: 70 percent / LiBr; SnBr4; CpRu(CH3CN)3PF6 / acetone / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / PDC / CH2Cl2 / 0 °C
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
[2]Trost; Pinkerton [Organic letters, 2000, vol. 2, # 11, p. 1601 - 1603]
  • 42
  • [ 30964-01-3 ]
  • [ 128948-49-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / pyridinium dichromate / CH2Cl2 / 1 h / 0 °C 5: 83 percent / H2 / Pd/C / methanol / 20 °C / 760.05 Torr 6: 100 percent / LiOH*H2O / dioxane; H2O / 1 h / 60 °C 7: 93 percent / sodium borohydride; NaOH / methanol / 1 h / 0 °C
Multi-step reaction with 7 steps 2: 70 percent / LiBr; SnBr4; CpRu(CH3CN)3PF6 / acetone / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / PDC / CH2Cl2 / 0 °C 5: 83 percent / H2 / Pd/C / methanol / 20 °C 6: aq. LiOH / dioxane / 60 °C 7: NaBH4 / methanol / 0 °C
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
[2]Trost; Pinkerton [Organic letters, 2000, vol. 2, # 11, p. 1601 - 1603]
  • 43
  • [ 30964-01-3 ]
  • [ 56695-64-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / pyridinium dichromate / CH2Cl2 / 1 h / 0 °C 5: 83 percent / H2 / Pd/C / methanol / 20 °C / 760.05 Torr 6: 100 percent / LiOH*H2O / dioxane; H2O / 1 h / 60 °C
Multi-step reaction with 6 steps 2: 70 percent / LiBr; SnBr4; CpRu(CH3CN)3PF6 / acetone / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / PDC / CH2Cl2 / 0 °C 5: 83 percent / H2 / Pd/C / methanol / 20 °C 6: aq. LiOH / dioxane / 60 °C
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
[2]Trost; Pinkerton [Organic letters, 2000, vol. 2, # 11, p. 1601 - 1603]
  • 44
  • [ 30964-01-3 ]
  • [ 277759-61-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C
Multi-step reaction with 3 steps 2: 70 percent / LiBr; SnBr4; CpRu(CH3CN)3PF6 / acetone / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
[2]Trost; Pinkerton [Organic letters, 2000, vol. 2, # 11, p. 1601 - 1603]
  • 45
  • [ 30964-01-3 ]
  • 8-bromo-12-oxo-octadec-8-enoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
  • 46
  • [ 30964-01-3 ]
  • 7-(5-hexyl-cyclopent-1-enyl)-heptanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / pyridinium dichromate / CH2Cl2 / 1 h / 0 °C 5: Zn; AcOH / 20 °C
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
  • 47
  • [ 30964-01-3 ]
  • 7-(2-hexyl-cyclopent)-heptanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2.1: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C 3.1: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4.1: 81 percent / pyridinium dichromate / CH2Cl2 / 1 h / 0 °C 5.1: zinc; acetic acid / 2 h / 20 °C 5.2: 21 mg / H2 / Pd/C / methanol / 20 °C / 750.08 Torr
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
  • 48
  • [ 30964-01-3 ]
  • 7-(2-hexyl-cyclopent-1-enyl)-heptanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 100 percent / toluene sulfonic acid hydrate / 3 h / Heating 2: 70 percent / [CpRu(CH3CN)3]PF6; stannic bromide; lithium bromide / acetone / 2 h / 60 °C 3: 71 percent / CrCl2; NiCl2 / dimethylformamide / 20 °C 4: 81 percent / pyridinium dichromate / CH2Cl2 / 1 h / 0 °C 5: Zn; AcOH / 20 °C
Reference： [1]Trost; Pinkerton [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7714 - 7722]
  • 49
  • [ 30964-01-3 ]
  • (E)-8-Bromo-12-oxo-octadec-8-enoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: LiBr; SnBr4; CpRu(CH3CN)3PF6 / acetone / 60 °C
Reference： [1]Trost; Pinkerton [Organic letters, 2000, vol. 2, # 11, p. 1601 - 1603]
  • 50
  • [ 30964-01-3 ]
  • [ 277759-62-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: 70 percent / LiBr; SnBr4; CpRu(CH3CN)3PF6 / acetone / 60 °C
Reference： [1]Trost; Pinkerton [Organic letters, 2000, vol. 2, # 11, p. 1601 - 1603]
  • 51
  • [ 3937-56-2 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1.) 48 percent HBr, concd. H2SO4; 2.) KMnO4 / 1.) 3 h, reflux; 2.) 20percent H2SO4, 15-20 deg C 3: 1.) aq. NaOH / 1.) 50 deg C 4: 79 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 5: 85 percent / aq. H2O2 / tetrahydrofuran / 24 h 7: aq. KOH / 0.5 h / Heating
Multi-step reaction with 6 steps 2: 1.) 20percent NaOH / 1.) water, 50 deg C 3: 73 percent / tri-n-butylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 4: 85 percent / 30percent H2O2 / tetrahydrofuran / 15 h 6: 30percent KOH / ethanol / 0.5 h / Heating
Multi-step reaction with 5 steps 2: 79 percent / NaBH4 / ethanol / 13 h / Ambient temperature 3: 85 percent / 30percent H2O2 / tetrahydrofuran / 15 h 5: 30percent KOH / ethanol / 0.5 h / Heating
Reference： [1]Nakatani; Fukunaga; Haraguchi; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539]
[2]Nakatani, Munehiro; Yamachika, Takashi; Tanoue, Takao; Hase, Tsunao [Phytochemistry, 1985, vol. 24, # 1, p. 39 - 42]
[3]Nakatani, Munehiro; Yamachika, Takashi; Tanoue, Takao; Hase, Tsunao [Phytochemistry, 1985, vol. 24, # 1, p. 39 - 42]
  • 52
  • [ 41059-02-3 ]
  • [ 30964-01-3 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 3535 - 3539
  • 53
  • [ 34957-73-8 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 79 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 2: 85 percent / aq. H2O2 / tetrahydrofuran / 24 h 4: aq. KOH / 0.5 h / Heating
Multi-step reaction with 4 steps 1: 73 percent / tri-n-butylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 2: 85 percent / 30percent H2O2 / tetrahydrofuran / 15 h 4: 30percent KOH / ethanol / 0.5 h / Heating
Reference： [1]Nakatani; Fukunaga; Haraguchi; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539]
[2]Nakatani, Munehiro; Yamachika, Takashi; Tanoue, Takao; Hase, Tsunao [Phytochemistry, 1985, vol. 24, # 1, p. 39 - 42]
  • 54
  • [ 67878-15-3 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) aq. NaOH / 1.) 50 deg C 2: 79 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 3: 85 percent / aq. H2O2 / tetrahydrofuran / 24 h 5: aq. KOH / 0.5 h / Heating
Multi-step reaction with 5 steps 1: 1.) 20percent NaOH / 1.) water, 50 deg C 2: 73 percent / tri-n-butylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 3: 85 percent / 30percent H2O2 / tetrahydrofuran / 15 h 5: 30percent KOH / ethanol / 0.5 h / Heating
Multi-step reaction with 4 steps 1: 79 percent / NaBH4 / ethanol / 13 h / Ambient temperature 2: 85 percent / 30percent H2O2 / tetrahydrofuran / 15 h 4: 30percent KOH / ethanol / 0.5 h / Heating
Reference： [1]Nakatani; Fukunaga; Haraguchi; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539]
[2]Nakatani, Munehiro; Yamachika, Takashi; Tanoue, Takao; Hase, Tsunao [Phytochemistry, 1985, vol. 24, # 1, p. 39 - 42]
[3]Nakatani, Munehiro; Yamachika, Takashi; Tanoue, Takao; Hase, Tsunao [Phytochemistry, 1985, vol. 24, # 1, p. 39 - 42]
  • 55
  • [ 95259-34-0 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 85 percent / aq. H2O2 / tetrahydrofuran / 24 h 3: aq. KOH / 0.5 h / Heating
Multi-step reaction with 3 steps 1: 85 percent / 30percent H2O2 / tetrahydrofuran / 15 h 3: 30percent KOH / ethanol / 0.5 h / Heating
Reference： [1]Nakatani; Fukunaga; Haraguchi; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539]
[2]Nakatani, Munehiro; Yamachika, Takashi; Tanoue, Takao; Hase, Tsunao [Phytochemistry, 1985, vol. 24, # 1, p. 39 - 42]
  • 56
  • [ 30964-01-3 ]
  • (8Z,10E)-12-hydroxyheptadeca-8,10-dienoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 86 percent / CuI, tetrakis(triphenylphosphine)palladium / diethylamine / 3 h / Ambient temperature 2: 35 percent / nickel boride, H2
Reference： [1]Haviv; Ratajczyk; DeNet; Martin; Dyer; Carter [Journal of Medicinal Chemistry, 1987, vol. 30, # 2, p. 254 - 263]
  • 57
  • [ 30964-01-3 ]
  • [ 13099-34-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: diethyl ether 2: LiAlH4 / diethyl ether / 2 h / 0 °C 3: 54 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; NH3 / 20 h 4: H2 / PtO2 / diethyl ether
Reference： [1]Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice; Bardy, Andre; Comet, Michel; Vidal, Michel [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55]
  • 58
  • [ 30964-01-3 ]
  • [ 60451-92-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: diethyl ether 2: LiAlH4 / diethyl ether / 2 h / 0 °C 3: 54 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; NH3 / 20 h 4: H2 / PtO2 / diethyl ether 5: pyridine / 0 °C 6: NaI / acetone / 2 h / Heating
Reference： [1]Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice; Bardy, Andre; Comet, Michel; Vidal, Michel [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55]
  • 59
  • [ 30964-01-3 ]
  • [ 62643-46-3 ]
Reference： [1]Bulletin de la Societe Chimique de France,1984,vol. 2,p. 49 - 55
  • 60
  • [ 30964-01-3 ]
  • [ 86244-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: diethyl ether 2: LiAlH4 / diethyl ether / 2 h / 0 °C 3: 64 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; NH3 / 20 h 4: H2 / PtO2 / diethyl ether 5: pyridine / 0 °C 6: NaI / acetone / 2 h / Heating
Reference： [1]Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice; Bardy, Andre; Comet, Michel; Vidal, Michel [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55]
  • 61
  • [ 30964-01-3 ]
  • [ 76298-42-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: diethyl ether 2: LiAlH4 / diethyl ether / 2 h / 0 °C 3: 54 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; NH3 / 20 h 4: H2 / PtO2 / diethyl ether 5: pyridine / 0 °C
Reference： [1]Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice; Bardy, Andre; Comet, Michel; Vidal, Michel [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55]
  • 62
  • [ 30964-01-3 ]
  • [ 344742-94-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: diethyl ether 2: LiAlH4 / diethyl ether / 2 h / 0 °C 3: 64 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; NH3 / 20 h 4: H2 / PtO2 / diethyl ether 5: pyridine / 0 °C
Reference： [1]Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice; Bardy, Andre; Comet, Michel; Vidal, Michel [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55]
  • 63
  • [ 30964-01-3 ]
  • [ 28079-04-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 86.2 percent / conc.H2SO4 / 4 h / Heating 2: 96 percent / LAH / diethyl ether / 2 h / Ambient temperature 3: 90.6 percent / PPTS / CH2Cl2 / 4 h / Ambient temperature 4: 1) n-BuLi, 2) HMPT / 1) THF, hexane, 10 deg C, 2) <25 deg C, 0.5 h 5: 83 percent / AcOH 6: 97 percent / H2, quinoline / 5percent Pd/BaSO4 / methanol
Reference： [1]Ranganathan, S.; Maniktala, Vibha; Kumar, Raaj; Singh, G. P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 12, p. 1197 - 1207]
  • 64
  • [ 30964-01-3 ]
  • [ 6638-79-5 ]
  • [ 744208-94-4 ]
YieldReaction ConditionsOperation in experiment
94% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 15h; 1.2-1 8-Nonynoic acid (50 g, 0.32mol) was added dropwise to a solution (500 ml) of N,O-dimethylhydroxylamine hydrochloride (63.3 g, 0.65mol), water-soluble carbodiimide hydrochloride (WSC·HCl) (124 g, 0.65mol), 1-hydroxybenzotriazole (HOBt) (99.3 g, 0.65mol) and N,N-diisopropylethylamine (DIPEA) (220 ml, 1.3mol) in dichloromethane at 0°C and the mixture was stirred at room temperature for 15 hours. The reaction solution was washed with a saturated aqueous ammonium chloride solution (400 ml), a saturated aqueous sodium hydrogencarbonate solution (400 ml) and a saturated aqueous NaCl solution (300 ml). After the organic layer was dehydrated and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue thus obtained was purified by column chromatography (Wako gel C-300, 500 g, Wako Purechemical) to obtain compound β (60 g, 94%) as a colorless oil from the hexane/ethyl acetate (20:1) eluting portion.Physicochemical Properties of Compound β Molecular weight 197ESI (LC/MS positive mode) 198 (M+H+)1H-NMR (in deutero chloroform) chemcial shift value δ: 1.30-1.70 (8H, m), 1.94 (1H, t, J=2.5 Hz), 2.19 (2H, dt, J=2.5, 7 Hz), 2.42 (2H, t, J=7.5 Hz), 3.18 (3H, s), 3.68 (3H, s)
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG; Chugai Pharmaceutical (in: Roche) - EP1593378, 2005, A1 Location in patent: Page/Page column 41-42
[2]Kawasaki, Ken-Ichi; Masubuchi, Miyako; Hayase, Tadakatsu; Komiyama, Susumu; Watanabe, Fumio; Fukuda, Hiroshi; Murata, Takeshi; Matsubara, Yasuaki; Koyama, Kouhei; Shindoh, Hidetoshi; Sakamoto, Hiroshi; Okamato, Kohichi; Ohta, Atsunori; Katsume, Asao; Aoki, Masahiro; Aoki, Yuko; Shimma, Nobuo; Sudoh, Masayuki; Tsukuda, Takuo [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 336 - 339]
  • 65
  • [ 30964-01-3 ]
  • [ 13488-15-8 ]
  • [ 925-90-6 ]
  • [ 19960-54-4 ]
YieldReaction ConditionsOperation in experiment
48% With hydrogenchloride In tetrahydrofuran; petroleum; acetone 2 EXAMPLE 2 To a solution of non-8-ynoic acid (3.3 g, 21 mmol) in tetrahydrofuran (10 ml) was added a 1.03 M solution (42 ml) of ethylmagnesium bromide in tetrahydrofuran during 5 minutes. The resulting mixture was stirred at 30° for 45 minutes, after which cuprous chloride (75 mg, 0.4 mmol) was added and stirring continued for 5 minutes. A solution of 1-bromodeca-2,5-diyne (Struyk et al., loc.cit.; 2.9 g, 14 mmol) in tetrahydrofuran (10 ml) was then added during 3 minutes, and the stirred mixture heated to 60° for 19 hours: at the end of the first 3 hours cuprous chloride (30 mg) was added. After heating was completed the mixture was cooled and ether (100 ml) and N hydrochloric acid were added. The mixture was thoroughly shaken, the ether layer which formed on standing was separated off and the aqueous layer extracted with ether: the combined ether layers were washed with saturated ammonium chloride solution, then with water, dried with anhydrous sodium sulphate and evaporated. The residue (5.5 g) was dissolved in a small quantity of light petroleum and chromatographed on a silica gel column (length 30 cm, diameter 2.2 cm) using as eluant mixtures of light petroleum and ether commencing with a proportion by volume of 80:20 and proceeding with increasing proportions of ether, with a final proportion of 20:80, and fractions of elude were collected. The eluted fractions found to contain acid were combined and evaporated: the residue was crystallized from a mixture of light petroleum and acetone (85:15 by volume) to give nonadeca-8,11,14-triynoic acid (1.9 g, 48%), m.p. 48.5°-49.5°; infrared absorption peaks at 1692 (--COOH) and 1310 cm-1 (--CH2 C C). The acid was converted by reaction with an ether solution of diazomethane to its methyl ester, which was submitted to GLC and shown to be of 99.7% purity; mass spectrum: parent peak at m/e=300.
Reference： [1]Current Patent Assignee: UNILEVER (PLC & NV) - US4163108, 1979, A
  • 66
  • [ 33821-94-2 ]
  • [ 30964-01-3 ]
  • C17H28O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: non-8-ynoic acid With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - 0℃; Inert atmosphere; Stage #2: 3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - 23℃; for 15h; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane Inert atmosphere;
Reference： [1]Falck; Kodela, Ravinder; Manne, Rajkumar; Atcha, Krishnam Raju; Puli, Narender; Dubasi, Narsimhaswamy; Manthati, Vijay L.; Capdevila, Jorge H.; Yi, Xiu-Yu; Goldman, Daniel H.; Morisseau, Christophe; Hammock, Bruce D.; Campbell, William B. [Journal of Medicinal Chemistry, 2009, vol. 52, # 16, p. 5069 - 5075]
  • 67
  • [ 37935-47-0 ]
  • [ 30964-01-3 ]
  • C19H32O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: non-8-ynoic acid With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - 0℃; Inert atmosphere; Stage #2: 2-(5-bromopentyloxy)tetrahydropyran In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - 23℃; for 15h; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane Inert atmosphere;
Reference： [1]Falck; Kodela, Ravinder; Manne, Rajkumar; Atcha, Krishnam Raju; Puli, Narender; Dubasi, Narsimhaswamy; Manthati, Vijay L.; Capdevila, Jorge H.; Yi, Xiu-Yu; Goldman, Daniel H.; Morisseau, Christophe; Hammock, Bruce D.; Campbell, William B. [Journal of Medicinal Chemistry, 2009, vol. 52, # 16, p. 5069 - 5075]
  • 68
  • [ 31608-22-7 ]
  • [ 30964-01-3 ]
  • [ 1184844-91-4 ]
Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5069 - 5075
  • 69
  • [ 30964-01-3 ]
  • C36H66N2O8 [ No CAS ]
  • C54H90N2O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.59 g With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane
Reference： [1]Location in patent: experimental part Nagasawa, Jun'Ichi; Yoshida, Masaru; Tamaoki, Nobuyuki [European Journal of Organic Chemistry, 2011, # 12, p. 2247 - 2255]
  • 70
  • [ 17643-36-6 ]
  • [ 30964-01-3 ]
  • [ 1642-49-5 ]
YieldReaction ConditionsOperation in experiment
With Jones reagent In acetone at 0℃; for 0.5h;
Reference： [1]Location in patent: scheme or table Bekish, Andrei V. [Tetrahedron Letters, 2012, vol. 53, # 24, p. 3082 - 3085]
  • 71
  • [ 30964-01-3 ]
  • [ 130-95-0 ]
  • [ 1383809-67-3 ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h;
Reference： [1]Location in patent: scheme or table Kuriakose, Jerrin; Hrycyna, Christine A.; Chmielewski, Jean [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4410 - 4412]
  • 72
  • [ 3731-52-0 ]
  • [ 30964-01-3 ]
  • N-(pyridin-3-ylmethyl)non-8-ynamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃;
Reference： [1]Theeramunkong; Galli; Grolla; Caldarelli; Travelli; Massarotti; Troiani; Alisi; Orsomando; Genazzani; Tron [MedChemComm, 2015, vol. 6, # 10, p. 1891 - 1897]
  • 73
  • [ 3731-53-1 ]
  • [ 30964-01-3 ]
  • N-(pyridin-4-ylmethyl)non-8-ynamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃;
Reference： [1]Theeramunkong; Galli; Grolla; Caldarelli; Travelli; Massarotti; Troiani; Alisi; Orsomando; Genazzani; Tron [MedChemComm, 2015, vol. 6, # 10, p. 1891 - 1897]
  • 74
  • [ 13258-63-4 ]
  • [ 30964-01-3 ]
  • N-(2-pyridin-4-ylethyl)non-8-ynamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃;
Reference： [1]Theeramunkong; Galli; Grolla; Caldarelli; Travelli; Massarotti; Troiani; Alisi; Orsomando; Genazzani; Tron [MedChemComm, 2015, vol. 6, # 10, p. 1891 - 1897]
  • 75
  • [ 20173-24-4 ]
  • [ 30964-01-3 ]
  • N-(2-pyridin-3-ylethyl)non-8-ynamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃;
Reference： [1]Theeramunkong; Galli; Grolla; Caldarelli; Travelli; Massarotti; Troiani; Alisi; Orsomando; Genazzani; Tron [MedChemComm, 2015, vol. 6, # 10, p. 1891 - 1897]
  • 76
  • [ 504-24-5 ]
  • [ 30964-01-3 ]
  • N-pyridin-4-ylnon-8-ynamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃;
Reference： [1]Theeramunkong; Galli; Grolla; Caldarelli; Travelli; Massarotti; Troiani; Alisi; Orsomando; Genazzani; Tron [MedChemComm, 2015, vol. 6, # 10, p. 1891 - 1897]
  • 77
  • [ 462-08-8 ]
  • [ 30964-01-3 ]
  • N-pyridin-3-ylnon-8-ynamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃;
Reference： [1]Theeramunkong; Galli; Grolla; Caldarelli; Travelli; Massarotti; Troiani; Alisi; Orsomando; Genazzani; Tron [MedChemComm, 2015, vol. 6, # 10, p. 1891 - 1897]
  • 78
  • [ 30964-01-3 ]
  • trans-6-hydroxy-2-((trimethylsilyl)ethynyl)cyclohex-2-en-1-yl acetate [ No CAS ]
  • trans-2-acetoxy-3-((trimethylsilyl)ethynyl)cyclohex-3-en-1-yl non-8-ynoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 23℃; for 15h; Inert atmosphere;
Reference： [1]Trost, Barry M.; Masters, James T.; Le Vaillant, Franck; Lumb, Jean-Philip [Journal of Organic Chemistry, 2016, vol. 81, # 20, p. 10023 - 10028]
  • 79
  • [ 31333-13-8 ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium; Trimethylenediamine; potassium <i>tert</i>-butylate / tetrahydrofuran; hexane / 3 h / 0 - 20 °C 2: chromium(VI) oxide; sulfuric acid / water; acetone / 0.33 h / 0 °C
Reference： [1]Kobayashi, Yuichi; Morita, Masao; Ogawa, Narihito; Kondo, Daiki; Tojo, Toshifumi [Organic and Biomolecular Chemistry, 2016, vol. 14, # 45, p. 10667 - 10673]
  • 80
  • [ 30964-01-3 ]
  • methyl (S,8E,10E)-12-hydroxyheptadeca-8,10-dienoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: diethyl ether / 0.08 h / Cooling with ice 2.1: tetrahydrofuran; diethyl ether / 1 h / 0 °C 3.1: sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; diethyl ether; water / 20 °C / Inert atmosphere 3.2: phosphate buffer / pH 5
Reference： [1]Kobayashi, Yuichi; Morita, Masao; Ogawa, Narihito; Kondo, Daiki; Tojo, Toshifumi [Organic and Biomolecular Chemistry, 2016, vol. 14, # 45, p. 10667 - 10673]
  • 81
  • [ 30964-01-3 ]
  • (S,8E,10E)-12-hydroxyheptadeca-8,10-dienoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: diethyl ether / 0.08 h / Cooling with ice 2.1: tetrahydrofuran; diethyl ether / 1 h / 0 °C 3.1: sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; diethyl ether; water / 20 °C / Inert atmosphere 3.2: phosphate buffer / pH 5 4.1: lithium hydroxide / tetrahydrofuran; water / 12 h / 20 °C 4.2: McIlvaine buffer / pH 5
Reference： [1]Kobayashi, Yuichi; Morita, Masao; Ogawa, Narihito; Kondo, Daiki; Tojo, Toshifumi [Organic and Biomolecular Chemistry, 2016, vol. 14, # 45, p. 10667 - 10673]
  • 82
  • [ 30964-01-3 ]
  • 8-isocyanatooctyne [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diphenyl phosphoryl azide; triethylamine In acetonitrile at 50℃; for 2h; Inert atmosphere;
Reference： [1]Opie, Christopher R.; Kumagai, Naoya; Shibasaki, Masakatsu [Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3349 - 3353][Angew. Chem., 2017, vol. 129, p. 3397 - 3401]
  • 83
  • [ 30964-01-3 ]
  • [ 15992-83-3 ]
  • N-(1,8-naphthyridin-2-yl)non-8-ynamide [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 3349 - 3353
    Angew. Chem.,2017,vol. 129,p. 3397 - 3401,5
  • 84
  • [ 30515-28-7 ]
  • lithium acetylide ethylenediamine complex [ No CAS ]
  • [ 30964-01-3 ]
YieldReaction ConditionsOperation in experiment
82% In dimethyl sulfoxide at 0 - 20℃; for 3h; Inert atmosphere;
Reference： [1]Opie, Christopher R.; Kumagai, Naoya; Shibasaki, Masakatsu [Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3349 - 3353][Angew. Chem., 2017, vol. 129, p. 3397 - 3401]
  • 85
  • [ 30964-01-3 ]
  • [ 123-38-6 ]
  • 10-hydroxy-8-dodecynoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
82 mg Stage #1: non-8-ynoic acid With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.166667h; Stage #2: propionaldehyde In tetrahydrofuran; hexane at 20℃;
Reference： [1]Kaspersen, Mads Holmgaard; Jenkins, Laura; Dunlop, Julia; Milligan, Graeme; Ulven, Trond [MedChemComm, 2017, vol. 8, # 6, p. 1360 - 1365]
  • 86
  • [ 30964-01-3 ]
  • [ 25542-64-7 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: non-8-ynoic acid With methanol In 1,2-dichloro-ethane at 20℃; for 3.5h; Inert atmosphere; Stage #2: With silica gel Inert atmosphere; General Procedure for Preparation of 5. General procedure: To a suspension of Au(DPB)Cl (4.0×10-3 mmol) in 1,2-dichloroethane was added AgSbF6 (4.0×10-3mmol) at room temperature. After stirring for 30 min, to a solution of Au(DPB)SbF6 in1,2-dichloroethane and MeOH (0.50 mmol) was added alkyne 4 at room temperature. The solventwas evaporated off. The residue was chromatographed with hexane-AcOEt to afford hydratedproduct. The results are shown in Table 2.
Reference： [1]Matsumoto, Chiaki; Yamada, Masayuki; Dong, Xun; Mukai, Chisato; Inagaki, Fuyuhiko [Chemistry Letters, 2018, vol. 47, # 10, p. 1321 - 1323]
  • 87
  • [ 630-18-2 ]
  • [ 30964-01-3 ]
  • 6-chloro-3-formyl-1H-indole-2-carboxylic acid ethyl ester [ No CAS ]
  • [ 100-46-9 ]
  • C33H37ClF3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 2,2,2-trifluoroethanol at 120℃; for 1.5h; Microwave irradiation; 6.1.1. General procedure for preparing compounds 3-15 General procedure: To a G10 microwave tube containing aldehyde (0.2 mmol, 1equiv.) in trifluoroethanol (2 mL), amine (0.2 mmol, 1 equiv.) wasadded, followed by addition of acid (0.2 mmol, 1 equiv.) and isocyanide(0.2 mmol, 1 equiv.). The reaction was stirred at 120 °Cunder the microwave irradiation for 90 min. TLC was used tomonitor the reaction. When the reaction is done, the solvent wasevaporated, and the residue was submitted to a silica gel flashcolumn (Hexane/EtOAc: 3/1e2/1), giving the desired product 3a-15a with the yields of 26%e51%.
Reference： [1]Wang, Bo; Liu, Jin; Tandon, Ira; Wu, Suzhen; Teng, Peng; Liao, Jianhua; Tang, Weiping [European Journal of Medicinal Chemistry, 2021, vol. 219]
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