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Chemistry
Organometallic Reagents
Organoboron
(E)-2-(2-(Cyclohex-1-en-1-yl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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[ CAS No. 245432-97-7 ] {[proInfo.proName]}

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Chemical Structure| 245432-97-7
Chemical Structure| 245432-97-7
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Product Details of [ 245432-97-7 ]

CAS No. :245432-97-7 MDL No. :MFCD08705304
Formula : C14H23BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KSZSVSZZECWICY-ZHACJKMWSA-N
M.W : 234.14 Pubchem ID :11310851
Synonyms :

Safety of [ 245432-97-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 245432-97-7 ]

* 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 [ 245432-97-7 ]

[ 245432-97-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 931-49-7 ]
  • [ 25015-63-8 ]
  • [ 245432-97-7 ]
YieldReaction ConditionsOperation in experiment
97% With C28H40CuNO In acetonitrile at 20℃; for 2h; Schlenk technique; Inert atmosphere; A General Protocol General procedure: To a flame dried Schlenk was added Et2CAACCuOPh (2.5 mol %) and a magnetic stir bar under an Ar atmosphere. 0.097 mL freshly distilled MeCN was added to fully dissolve catalyst and yield a 2.3 ± 0.1 M solution depending on the nature of the alkyne. Alkyne (0.56 mmol, 1 eq.) was added followed immediately by pinacolborane (0.57 mmol, 1.025 eq). The resulting solution is stirred at room temperature for 2 hours. After this time, the volatiles were evaporated under vacuum. 10 mL pentane was added to residue. This solution was passed through a pad of silica (5 cm diameter x 5 cm high) to remove insoluble components. Elution with 2 x 10 mL of pentane, followed by evaporation under vacuum yielding pure products 2a-m.
96% With tris[N,N-bis(trimethylsilyl)amide]yttrium In toluene at 100℃; for 24h; Inert atmosphere; 6 Preparation of (E)-2-(2-(cyclohex-1-en-1-yl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane , The structural formula is as follows: Under the protection of nitrogen, add the raw material cyclohexenyl phenyl acetylene (0.5 mmol),Catalyst Y[N(SiMe3)2]3(1mol%), HBpin(1.2mmol), toluene (2mL), reacted at 100 for 24h, the product separation yield is 96%
91% With lithium hexamethyldisilazane In toluene at 100℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;
91% With 8C4H8O*10Br(1-)*5Co(2+)*2C14H10N8; sodium triethylborohydride In tetrahydrofuran; tert-butyl methyl ether at 45℃; for 10h; Inert atmosphere; Schlenk technique; regioselective reaction;
87% With bis(cyclohexanyl)borane at 20℃; for 2h;
87% With [FeH(tBuPNP)] In hexane at 20℃; for 16h; Inert atmosphere; Glovebox; Schlenk technique; chemoselective reaction;
86% With bis(cyclopentadienyl)zirconium(IV) chloride hydride; triethylamine at 60℃;
86% With bis(cyclopentadienyl)zirconium(IV) chloride hydride; triethylamine at 60℃; for 12h; Inert atmosphere; Neat (no solvent);
84% With bis(cyclopentadienyl)zirconium(IV) chloride hydride at 0 - 20℃; for 48.5h; Inert atmosphere;
84% With bis(cyclopentadienyl)zirconium(IV) chloride hydride at 0 - 20℃; for 64h; Inert atmosphere;
83% With Zinc di(trifluoromethanesulphonate); sodium triethylborohydride In tetrahydrofuran; toluene at 80℃; for 10h; Schlenk technique; Inert atmosphere; regioselective reaction;
82% With Di-n-butylmagnesium In n-heptane; toluene at 80℃; for 18h; Inert atmosphere; regioselective reaction;
80% With diisobutylaluminium hydride In hexane; toluene at 110℃; for 2h; Inert atmosphere; chemoselective reaction;
80% With sodium triethylborohydride; scandium trifluoromethanesulphonate In tetrahydrofuran; toluene at 100℃; for 24h; Microwave irradiation; Inert atmosphere; regioselective reaction;
80% With lithium hexamethyldisilazane In toluene at 100℃; for 24h; Inert atmosphere; 10 Preparation method: Under the protection of nitrogen, add the raw material cyclohexenyl acetylene (0.5mmol), pinacol borane (0.6mmol), catalyst LHMDS (7mol%) and organic solvent toluene (0.5mL) into the reaction vessel and mix with stirring. After mixing uniformly, react at 100°C for 24h, filter and purify to obtain the product; the product separation yield is 80%.
79% In neat (no solvent) at 215℃; for 0.416667h; Microwave irradiation; stereoselective reaction;
75% With C39H22BF10OP In dichloromethane-d2 at 20℃; The reaction was carried out according to the general procedure above by using 1 - cyclohexenyl)acetylene (53 mg, 0.5 mmol) and HBpin (64 mg, 0.5 mmol). The resulting reaction mixture was monitored by 1H NMR and 11 B NMR spectroscopy. After 36 hours, the yield of product is about 75%. 1H NMR (400 MHz, CD2CI2, 25<€): δ 6.87 (d, JHH = 18.0 Hz, CH), 5.87 (t, J = 3.6 Hz, CHCH2), 5.27 (d, JHH = 18.0 Hz, CHB), 2.08-2.03 (m, 4H), 1.53-1.49 (m, 4H), 1.15 (s, 12H). 11B NMR (160 MHz, CD2CI2, 25°C): 30.2 (br) ppm.
75% In neat (no solvent) at 110℃; for 12h; Inert atmosphere;
71% With C42H56AlN5 In neat (no solvent) at 60℃; for 12h; Sealed tube; chemoselective reaction;
70% With silver(I) acetate In toluene at 120℃; for 24h; Inert atmosphere; Sealed tube;
68% With tris(pentafluorophenyl)borate In toluene at 60℃; for 2h; Inert atmosphere; chemoselective reaction;
63% With silver(I) acetate In toluene at 120℃; for 18h; Schlenk technique; Inert atmosphere; stereoselective reaction;
59% With 9-bora-[3.3.1]-bicyclononane dimer In tetrahydrofuran at 20℃; for 2h;
50% With p-N,N-dimethylaminobenzoic acid In octane at 100℃; for 12h; Inert atmosphere;
50% Stage #1: 4,4,5,5-tetramethyl-1,3,2-dioxaborolane With 1,3-bis-(diphenylphosphino)propane; cobalt(II) 2,4-pentanedionate In acetonitrile at 20℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: 1-ethenylcyclohexene In acetonitrile at 20℃; for 16h; Inert atmosphere; Schlenk technique; chemoselective reaction;
68 %Spectr. With 2Fe(1+)*9CO In toluene at 100℃; for 24h; Inert atmosphere;
With bis(pentafluorophenyl)borane In dichloromethane at 20℃; for 5h; Glovebox; Inert atmosphere; Sealed tube;
97 %Spectr. With lithium 2,6-di-tert-butylphenolate In neat (no solvent) at 100℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction;

Reference： [1]Romero, Erik A.; Jazzar, Rodolphe; Bertrand, Guy [Journal of Organometallic Chemistry, 2017, vol. 829, p. 11 - 13]
[2]Current Patent Assignee: WENZHOU UNIV NEW MATERIAL AND INDUSTRY TECHNOLOGY - CN112778344, 2021, A Location in patent: Paragraph 0045-0049
[3]Liu, Jichao; Wu, Caiyan; Hu, Tinghui; Yang, Wei; Xie, Yaoyao; Shi, Yinyin; Liu, Qianrui; Shao, Yinlin; Zhang, Fangjun [Journal of Organic Chemistry, 2022, vol. 87, # 5, p. 3442 - 3452]
[4]Jia, Jun-Song; Wu, Tai-Xue; Fu, Yi-Jia; Hu, Zhi-Rong; Tang, Hai-Tao; Pan, Ying-Ming; Huang, Fu-Ping [Advanced Synthesis and Catalysis, 2022, vol. 364, # 11, p. 1873 - 1878]
[5]Shirakawa, Kazuya; Arase, Akira; Hoshi, Masayuki [Synthesis, 2004, # 11, p. 1814 - 1820]
[6]Nakajima, Kazunari; Kato, Takeru; Nishibayashi, Yoshiaki [Organic Letters, 2017, vol. 19, # 16, p. 4323 - 4326]
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[13]Bismuto, Alessandro; Thomas, Stephen P.; Cowley, Michael J. [Angewandte Chemie - International Edition, 2016, vol. 55, # 49, p. 15356 - 15359][Angew. Chem., 2016, vol. 128, p. 15582 - 15585,4]
[14]Mandal, Souvik; Verma, Piyush Kumar; Geetharani [Chemical Communications, 2018, vol. 54, # 97, p. 13690 - 13693]
[15]Current Patent Assignee: WENZHOU UNIV NEW MATERIAL AND INDUSTRY TECHNOLOGY - CN113563372, 2021, A Location in patent: Paragraph 0012; 0068-0072
[16]Altarejos, Julia; Sucunza, David; Vaquero, Juan J.; Carreras, Javier [European Journal of Organic Chemistry, 2020, vol. 2020, # 20, p. 3024 - 3029]
[17]Current Patent Assignee: Oxford University Innovation (in: Oxford University); UNIVERSITY OF OXFORD - WO2016/198892, 2016, A1 Location in patent: Paragraph 00137; 00143
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  • 2
  • [ 931-49-7 ]
  • [ 73183-34-3 ]
  • [ 245432-97-7 ]
YieldReaction ConditionsOperation in experiment
93% With methanol; copper (I) tert-butoxide; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; regioselective reaction;
88% With water In toluene at 80℃; for 10h; Schlenk technique; Sealed tube; regioselective reaction;
81% With tetrabutylammonium tetrafluoroborate In methanol at 20℃; Electrochemical reaction;
81% With tetrabutylammonium tetrafluoroborate In methanol
80% With [Cu(phen)(xantphosTEPD)]PF6; potassium carbonate In water; acetonitrile at 20℃; for 7h; Sealed tube; Inert atmosphere; Irradiation; diastereoselective reaction;
71% With (1-(2-(2,3-diisopropyl-1-methylguanidino)ethyl)-3-mesityl-1,3-dihydro-2H-imidazol-2-ylidene)copper(I) chloride In tetrahydrofuran; water at 20℃; for 1h; stereoselective reaction;
63% With 1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene silver chloride; potassium <i>tert</i>-butylate In tetrahydrofuran; methanol at 50℃; for 8h; Schlenk technique; Inert atmosphere; regioselective reaction;
32% With sodium methylate; copper In ethanol at 20℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Sasaki, Yusuke; Horita, Yuko; Zhong, Chongmin; Sawamura, Masaya; Ito, Hajime [Angewandte Chemie - International Edition, 2011, vol. 50, # 12, p. 2778 - 2782]
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[5]Zhong, Mingbing; Gagné, Yohann; Hope, Taylor O.; Pannecoucke, Xavier; Frenette, Mathieu; Jubault, Philippe; Poisson, Thomas [Angewandte Chemie - International Edition, 2021, vol. 60, # 26, p. 14498 - 14503][Angew. Chem., 2021, vol. 133, # 26, p. 14619 - 14624]
[6]Tai, Chia-Cheng; Yu, Ming-Shiuan; Chen, Yi-Lin; Chuang, Wen-Hang; Lin, Ting-Hua; Yap, Glenn P. A.; Ong, Tiow-Gan [Chemical Communications, 2014, vol. 50, # 33, p. 4344 - 4346]
[7]Yoshida, Hiroto; Kageyuki, Ikuo; Takaki, Ken [Organic Letters, 2014, vol. 16, # 13, p. 3512 - 3515]
[8]Li, Jian-Jun; Wang, Cheng-Gang; Yu, Jin-Feng; Wang, Peng; Wang, Peng; Yu, Jin-Quan [Organic Letters, 2020, vol. 22, # 12, p. 4692 - 4696]

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