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[ CAS No. 18486-69-6 ] {[proInfo.proName]}

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Chemical Structure| 18486-69-6
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Product Details of [ 18486-69-6 ]

CAS No. :18486-69-6 MDL No. :MFCD00074768
Formula : C10H14O Boiling Point : -
Linear Structure Formula :- InChI Key :KMRMUZKLFIEVAO-IUCAKERBSA-N
M.W : 150.22 Pubchem ID :1201529
Synonyms :
(−)-Myrtenal;(1R)-(−)-Myrtenal;(−)-(1R,5S)-Myrtenal
Chemical Name :(1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Calculated chemistry of [ 18486-69-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.7
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.42
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 2.98
Log Po/w (WLOGP) : 2.18
Log Po/w (MLOGP) : 2.2
Log Po/w (SILICOS-IT) : 2.45
Consensus Log Po/w : 2.38

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.58
Solubility : 0.393 mg/ml ; 0.00261 mol/l
Class : Soluble
Log S (Ali) : -3.0
Solubility : 0.15 mg/ml ; 0.000995 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.8
Solubility : 2.37 mg/ml ; 0.0158 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.16

Safety of [ 18486-69-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335-H227 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18486-69-6 ]

* 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 [ 18486-69-6 ]

[ 18486-69-6 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 19894-97-4 ]
  • [ 18486-69-6 ]
YieldReaction ConditionsOperation in experiment
98% With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 12h; chemoselective reaction;
85% Stage #1: (1R)-Myrtenol With C6H13N2O(1+)*C6H12N2O*C24H20B(1-) In acetonitrile at 20℃; for 0.166667h; Stage #2: With tetrapropylammonium perruthennate In acetonitrile at 20℃; for 16h;
74% Stage #1: (1R)-Myrtenol With C24H20B(1-)*C5H12NO2(1+)*C5H11NO2 In acetonitrile at 20℃; for 0.166667h; Stage #2: With tetrapropylammonium perruthennate In acetonitrile at 20℃;
33% With oxone; C18H17IN2O7PolS(1-)*Na(1+); tetra(n-butyl)ammonium hydrogensulfate; sodium sulfate In acetonitrile at 70℃; for 18h; Sealed tube; Inert atmosphere; Green chemistry;
With chromium(VI) oxide
With 1-bromo-butane; N-chloro-succinimide; magnesium; <i>tert</i>-butyl alcohol 1.) THF, 10 min, 2.) THF, RT, 25 min; Yield given. Multistep reaction;
99 % Turnov. With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid In dichloromethane at 20℃; for 0.25h;
With styrene; aluminum oxide; copper In toluene at 89.84℃; for 30h;
25 %Chromat. With tert.-butylhydroperoxide; manganese(IV) oxide In decane; toluene; acetonitrile at 20℃; for 24h; General procedure for the oxidations of alcohols General procedure: The alcohol (1.2mmol) of interest was dissolved in a mixture of acetonitrile (3ml) and toluene (1ml) for the experiments with TBHP/decane (or in 4ml of acetonitrile for the experiments with TBHP/H2O) and the desired amount of MnO2 (see Tables) was added to the solution. Then tert-butyl hydroperoxide (TBHP, as a 5.3M solution in decane, 453μL, 2.4mmol) was added to the reaction mixture, which was set at the desired reaction temperature with magnetic stirring in air. Aliquots (0.2ml) were withdrawn at different time intervals, diluted with 1ml of diethyl ether and filtered through a Pasteur pipette filled up with silica to eliminate the residual MnO2. The silica was washed with 2ml of diethyl ether. The resulting organic phase was analyzed by gas chromatography using diethyleneglycol dibutyl ether as an external standard.

  • 2
  • [ 108-86-1 ]
  • [ 18486-69-6 ]
  • (1R)-10-epi-phenylmyrtenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: bromobenzene With magnesium In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: myrtenal In tetrahydrofuran for 3h; Reflux; Inert atmosphere;
(i) Mg, Et2O, (ii) /BRN= 2961587/; Multistep reaction;
  • 3
  • [ 18486-69-6 ]
  • [ 19894-97-4 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde With (dppe)2Fe(H)2*(C7H8)2; Na-tetrakis(ethoxy)borate In toluene at 100℃; for 1h; visible light irradiation; Inert atmosphere; Stage #2: With water monomer; sodium hydroxide In methanol; toluene at 20℃; for 16h;
95% With methanol; sodium tetrahydridoborate at 0℃; for 1h; Inert atmosphere;
89% With sodium tetrahydridoborate; askanite-bentonite clay In dichloromethane at 20℃; for 1h;
81% With indium(III) isopropoxide; isopropanol at 20℃; for 0.5h; Inert atmosphere;
58% With methanol; sodium tetrahydridoborate at 20℃; for 3h;
With potassium borohydrate
73 % Chromat. With Diplogelasinospora grovesii IMI 171018 cells at 28℃; for 72h;
Multi-step reaction with 2 steps 1: 92 percent / NaOH / tetrahydrofuran; H2O / 20 h / 20 °C 2: Na / liquid ammonia; diethyl ether
Multi-step reaction with 2 steps 1: [CpFe(IMes)(CO2)]I / 3 h / 30 °C / Inert atmosphere; Neat (no solvent); visible light irradiation 2: sodium hydroxide / methanol; water monomer / 1 h / 20 °C
With sodium tetrahydridoborate In ethanol
With sodium tetrahydridoborate In methanol at 0 - 20℃; 3.1.3. Synthesis of compounds 16, 17, (+)-19, (-)-19, 22 General procedure: Bromides 16, 17, (+)- and (-)-19, 22 were synthesized from the corresponding monoterpene or methoxyphenyl aldehydes (14, 15, (+)- and (-)-18) via reduction to alcohols with NaBH4,34 followed by the reaction with PBr3.36 NaBH4 (10.3 mmol) was added to cooled (0-5 °C) solution of 10.3 mmol of appropriate aldehyde in methanol (20 ml) and the reaction mixture was stirred for 3 h at rt. Then 5% aqueous HCl was added to reach pH 4-5. The solvent was distilled off and the product was extracted by ether, dried with Na2SO4. The solvent was evaporated; resulting alcohols were used in the synthesis without purification (yields of alcohols-34-73%).
With methanol; sodium tetrahydridoborate
49.7 g With sodium tetrahydridoborate; ethanol 3.8 Step 8: Reduction of aldehyde 20 to allylic alcohol 21 (Fig. 22) (lR)-(-)-Myrtenal (compound 20) was reduced to (lR)-(-)-Myrtenol (21) with NaBFU. The reaction was carried out starting from 47.6 g of (IR)-(-)- Myrtenal with NaBFU (1.1 eq) in EtOH (20 vol) following a trial reaction. The desired product was isolated in 49.7 g yield. The JH NMR spectrum for compound 21 is shown in Fig. 27.

Reference: [1]Castro, Luis C. Misal; Bezier, David; Sortais, Jean-Baptiste; Darcel, Christophe [Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1279 - 1284]
[2]Bé, Ariana Gray; Bellcross, Aleia; Geiger, Franz M.; Thomson, Regan J. [Journal of the American Chemical Society, 2021, vol. 143, # 40, p. 16653 - 16662]
[3]Il'ina, Irina V.; Volcho, Konstantin P.; Korchagina, Dina V.; Barkhash, Vladimir A.; Salakhutdinov, Nariman F. [Helvetica Chimica Acta, 2007, vol. 90, # 2, p. 353 - 368]
[4]Lee, Jaeyoung; Ryu, Taekyu; Park, Sangjune; Lee, Phil Ho [Journal of Organic Chemistry, 2012, vol. 77, # 10, p. 4821 - 4825]
[5]Ayine-tora, Daniel M.; Chand, Raina; Chepanova, Arina A.; Ilina, Ekaterina S.; Kaledin, Vasily I.; Khomenko, Tatyana M.; Korchagina, Dina V.; Lavrik, Olga I.; Leung, Ivanhoe K. H.; Nikolin, Valeriy P.; Patel, Jinal; Popova, Nelly A.; Reynisson, Jóhannes; Salakhutdinov, Nariman F.; Volcho, Konstantin P.; Zakharenko, Alexandra L.; Zakharova, Olga D. [International Journal of Molecular Sciences, 2020, vol. 21, # 1]
[6]Julia,S. et al. [Bulletin de la Societe Chimique de France, 1962, p. 1947 - 1952]
[7]Carballeira, Jose D.; Alvarez, Emilio; Campillo, Mercedes; Pardo, Leonardo; Sinisterra, Jose V. [Tetrahedron Asymmetry, 2004, vol. 15, # 6, p. 951 - 962]
[8]Martinez-Ramos, Federico; Vargas-Diaz, Maria Elena; Chacon-Garcia, Luis; Tamariz, Joaquin; Joseph-Nathan, Pedro; Zepeda [Tetrahedron Asymmetry, 2001, vol. 12, # 22, p. 3095 - 3103]
[9]Bezier, David; Jiang, Fan; Roisnel, Thierry; Sortais, Jean-Baptiste; Darcel, Christophe [European Journal of Inorganic Chemistry, 2012, # 9, p. 1333 - 1337]
[10]Banina; Sudarikov; Krymskaya; Frolova; Kuchin [Chemistry of Natural Compounds, 2015, vol. 51, # 2, p. 261 - 265][Khim. Prir. Soedin., 2015, vol. 2, p. 231 - 234,4]
[11]Khomenko, Tatyana; Zakharenko, Alexandra; Odarchenko, Tatyana; Arabshahi, Homayon John; Sannikova, Victoriya; Zakharova, Olga; Korchagina, Dina; Reynisson, Jóhannes; Volcho, Konstantin; Salakhutdinov, Nariman; Lavrik, Olga [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5573 - 5581]
[12]Dyrkheeva, Nadezhda S.; Filimonov, Aleksandr S.; Luzina, Olga A.; Zakharenko, Alexandra L.; Ilina, Ekaterina S.; Malakhova, Anastasia A.; Medvedev, Sergey P.; Reynisson, Jóhannes; Volcho, Konstantin P.; Zakian, Suren M.; Salakhutdinov, Nariman F.; Lavrik, Olga I. [Biomolecules, 2021, vol. 11, # 7]
[13]Current Patent Assignee: TETRA BIO-PHARMA INC - WO2022/61461, 2022, A1 Location in patent: Paragraph 00254; 00257-00258
  • 4
  • [ 18486-69-6 ]
  • [ 1779-49-3 ]
  • [ 30293-06-2 ]
YieldReaction ConditionsOperation in experiment
95% With potassium-t-butoxide In tetrahydrofuran at 23℃; for 14h; Inert atmosphere;
95% Stage #1: triphenylmethylphosphonium bromide With potassium-t-butoxide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde In tetrahydrofuran at 20℃; for 14h;
86% Stage #1: triphenylmethylphosphonium bromide With potassium-t-butoxide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde In tetrahydrofuran at 20℃; for 24h;
61% Stage #1: triphenylmethylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -50 - -10℃; for 0.75h; Stage #2: (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde In tetrahydrofuran; hexane at -50 - 20℃;
With phenyllithium 1.) ether, THF, RT, 4 h, 2.) ether, THF, 3 h; Yield given. Multistep reaction;
Stage #1: triphenylmethylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Stage #2: (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde In tetrahydrofuran; hexan-1-ol at 20℃;

  • 5
  • [ 18486-69-6 ]
  • 2,6-bis(pyridinioacetyl)pyridine diiodide [ No CAS ]
  • (-)-2,6-bis(4′,5′-pinene-2′-pyridyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With anhydrous ammonium acetate In formamide at 80℃; for 12h;
63% With anhydrous ammonium acetate; glacial acetic acid Heating;
50% With ammonium acetate In nitromethane at 79.84℃; for 3h; Synthesis of Compound 7. Compound 6 (5.00 g, 8.73 mmol), R-myrtenal (3.04g, 20mmol) and ammonium acetate (27.8 ml, 2.00 ml) were dissolved in nitromethane (20mL). The mixture was stirred at 353 K for 3 h. After cooling to room temperature, themixture was extracted with CH2Cl2/H2O and dried with MgSO4 and filtered. Thesolvent was removed under reduced pressure. The residue was purified by columnchromatography (CH2Cl2 as the eluent). The product was obtained as a brown solid(1.84 g, 50%). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.39 (s, 2H), 8.36 (d, J = 8.0 Hz,2H), 8.23 (s, 2H), 7.91 (t, J = 8.0 Hz, 1H), 3.13 (s, 4H), 2.89 (t, J = 5.2 Hz, 2H), 2.76-2.70 (m, 2H), 2.37-2.32 (m, 2H), 1.44 (s, 6H), 1.26 (d, J = 9.6 Hz, 2H), 0.69 (s, 6H).13C NMR (100 MHz, CDCl3) δ (ppm): 156.1, 154.9, 145.8, 145.6, 143.3, 138.0, 120.8,120.7, 44.8, 40.4, 39.6, 33.3, 32.1, 26.3, 21.7. ESI-MS m/z: [M + H]+, 422.28.
  • 6
  • [ 18486-69-6 ]
  • [ 92834-76-9 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: myrtenal With N,N-Dimethylhydrazine In toluene at 20℃; for 2h; Stage #2: With magnesium monoperoxyphthalate hexahydrate In methanol; toluene at 0℃; for 0.25h;
90% With PhNHCO2NH2*TsOH In toluene for 0.5h; Heating;
Multi-step reaction with 2 steps 1: NH2OH*HCl; NaHCO3 / ethanol; H2O / 20 h / Heating 2: 67.9 g / Ac2O; NaOAc / 120 h / 100 °C
Multi-step reaction with 2 steps 1: 92 percent / ethanol / 1 h / 20 °C 2: 95 percent / TsOH*H2O / toluene / 0.5 h / Heating
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium carbonate / water / 20 h / 60 °C 2: copper diacetate / acetonitrile / 16 h / Reflux

  • 7
  • [ 18486-69-6 ]
  • 1-{3-[(E)-Hydroxyimino]-2-oxo-butyl}-pyridinium; bromide [ No CAS ]
  • 1-((1R,9R)-10,10-Dimethyl-4-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-trien-5-yl)-ethanone oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With ammonium acetate In formamide at 20℃; for 168h;
With ammonium acetate In N,N-dimethyl-formamide at 80℃;
  • 8
  • [ 18486-69-6 ]
  • [ 74-86-2 ]
  • [ 639839-79-5 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: acetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: myrtenal In tetrahydrofuran at -78℃; for 1h;
Stage #1: acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: myrtenal In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;
  • 9
  • [ 18486-69-6 ]
  • [ 84488-18-6 ]
  • [ 608517-53-9 ]
YieldReaction ConditionsOperation in experiment
82% With ammonium acetate In ethanol at 85℃; for 24h;
43% With ammonium acetate In nitromethane at 79.84℃; for 3h; Synthesis of Compound 10. Compound 9 (1.00 g, 2.47 mmol), R-myrtenal (750 mg,5 mmol) and ammonium acetate (0.50 mL, 6.95 mmol) were dissolved in nitromethane(20 mL). The mixture was stirred at 353 K for 3 h. After cooling to room temperature,the mixture was extracted with CH2Cl2/H2O and dried with MgSO4. The solvent wasremoved under reduced pressure. The residue was purified by column chromatography(CH2Cl2 as the eluent). The product was a brown solid (350 mg, 43%). 1H NMR (400MHz, CDCl3) δ (ppm): 8.30 (d, J = 7.6 Hz, 1H), 8.16 (s, 2H), 7.61 (t, J = 8.0 Hz, 1H),7.42 (d, J = 8.0 Hz, 1H), 3.02 (d, J = 2.8 Hz, 2H), 2.84 (t, J = 5.6 Hz, 1H), 2.69-2.66(m, 1H), 2.30-2.28 (m, 1H), 1.39 (s, 3H), 1.19 (d, J = 6.0 Hz, 1H), 0.62 (s, 3H). 13CNMR (100 MHz, CDCl3) δ (ppm): 158.1, 152.9, 145.8, 143.9, 143.6, 141.6, 139.4,127.6, 121.0, 119.7, 44.7, 33.1, 32.0, 26.2, 21.6. ESI-MS m/z: [M + H]+, 328.95.
29% With ammonium acetate In formamide at 20 - 100℃;
  • 10
  • [ 18486-69-6 ]
  • [ 1066-54-2 ]
  • [ 590420-39-6 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: myrtenal In tetrahydrofuran at -78℃; for 2h;
95% Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: myrtenal In tetrahydrofuran Further stages.;
  • 11
  • [ 18486-69-6 ]
  • [ 188447-91-8 ]
  • (S)-(+)-N-(myrtenalidene)-p-toluenesulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With ytterbium(III) triflate In tetrahydrofuran at 20℃; for 12h;
  • 12
  • [ 505-66-8 ]
  • [ 18486-69-6 ]
  • N,N'-bis(2-myrtanyl)homopiperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With polymer-bound trimethylammonium cyanoborohydride In acetic acid; 1,2-dichloro-ethane at 20℃;
  • 13
  • [ 5651-91-2 ]
  • [ 18486-69-6 ]
  • [ 883555-84-8 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 1,2-bis(prop-2-ynyloxy)benzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: myrtenal In tetrahydrofuran; hexane at 20℃; for 3h; Further stages.;
  • 14
  • [ 26627-36-1 ]
  • [ 18486-69-6 ]
  • [ 883555-85-9 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: m-bis(propargyloxy)benzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: myrtenal In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.;
  • 15
  • [ 34596-36-6 ]
  • [ 18486-69-6 ]
  • [ 883555-96-2 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 1,4-bis(prop-2-yn-1-yloxy)benzene With N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: myrtenal In tetrahydrofuran at 20℃; for 2h; Further stages.;
  • 16
  • [ 63104-44-9 ]
  • [ 18486-69-6 ]
  • C31H40O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: dimethyl 2,2-di(prop-2-ynyl)malonate With N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: myrtenal In tetrahydrofuran at 20℃; for 1h; Further stages.;
  • 17
  • [ 2468-61-3 ]
  • [ 18486-69-6 ]
  • C39H42O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 9,9-di(prop-2-ynyl)-9H-fluorene With N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: myrtenal In tetrahydrofuran at 20℃; for 3h; Further stages.;
  • 18
  • [ 70254-44-3 ]
  • [ 18486-69-6 ]
  • C19H19NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With ethylenediamine diacetic acid In dichloromethane at 20℃; for 10h;
  • 19
  • [ 18486-69-6 ]
  • [ 20051-66-5 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: myrtenal With tetrafluoroboric acid-diethyl ether complex In tetrahydrofuran at 0 - 20℃; for 27h; Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 1.5h; Further stages.;
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol 2: dihydrogen peroxide; borane / diethyl ether / 0 °C / Alkaline conditions
  • 20
  • [ 18486-69-6 ]
  • [ 105498-90-6 ]
YieldReaction ConditionsOperation in experiment
95% With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; sodium hydroxide In water at 80℃; for 12h; chemoselective reaction;
90% With sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 10 - 20℃; Synthesis of (-)-myrtenic acid 23c A solution of NaClO2 (8.0 g, 70 mmol) in H2O (70 mL) was added slowly for 2 h to astirred mixture of (-)-myrtenal (7.7 g, 51 mmol) in CH3CN (50 mL), KH2PO4 (1.8 g) in water(20 mL), H2O2 (37%, 5 mL, 52 mmol) and polyethylene glycol (PEG-400, 3.0 g) at 10 C withice-water cooling. The reaction was stirred overnight at room temperature. Then, Na2SO3(0.5 g) was added. The resulting mixture was acidified with 10% aqueous HCl to pH 3 andextracted several times with diethyl ether. The separated organic phase was washed withsaturated sodium bisulfite and water, respectively, and then dried over anhydrous sodiumsulfate. Evaporation of the solvent gave (-)-myrtenic acid as a yellow solid (7.67 g, 90%).
80% With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 10℃; for 7h;
80% With potassium dihydrogenphosphate; sodium chlorate; dihydrogen peroxide In acetonitrile
Multi-step reaction with 3 steps 1: NH2OH*HCl; NaHCO3 / ethanol; H2O / 20 h / Heating 2: 67.9 g / Ac2O; NaOAc / 120 h / 100 °C 3: 99 percent / aq. NaOH; aq. H2O2 / 96 h / Heating
With sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide In <i>tert</i>-butyl alcohol

  • 21
  • [ 18486-69-6 ]
  • [ 128301-02-0 ]
YieldReaction ConditionsOperation in experiment
97% With o-phenylenebis(diphenylphosphine); copper diacetate; poly(methylhydrosiloxane) In toluene; <i>tert</i>-butyl alcohol at 20℃; for 3h;
  • 22
  • [ 1036733-28-4 ]
  • [ 18486-69-6 ]
  • [ 1036733-60-4 ]
YieldReaction ConditionsOperation in experiment
78% With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 12h; 10.I A solution of scaffold 1{1-4} (13.0-14.0 mg, 1.0 equiv) in MeOH (1.5 mL) was placed in a reaction vial. To this solution was added aldehyde (5.0 equiv) in MeOH (0.5 mL), followed by the addition of NaBH3CN (5.0 equiv). The pH of the reaction was adjusted to 6 by adding HOAc. The reaction mixture was stirred at room temperature overnight (12 h), then quenched with saturated NaHCO3 solution (5.0 mL), and extracted with EtOAc (3×10 mL). The organic layers were combined and washed with brine, then dried over Na2SO4. The solvent was removed in vacuo and the crude residue was purified by flash chromatography on silica gel to give the desired product 10a-10e (Table 4). Representative examples are given as below.(8S)-2-((6,6-Dimethylbicyclo[3.1.1]hept-2-en-3-yl)methyl)-8-methyl-6-phenyl-2,3,4,7,8,10-hexahydro-1H-pyrano[4,3-c][1,6]naphthyridine (10b): Compound 10b was prepared according to Procedure I, as described above, beginning with 1{1} (14.0 mg, 0.050 mmol), (1R)-(-)-myrtenal (38 μl, 0.250 mmol, 5.0 equiv) and NaBH3CN (16.0 mg, 0.250 mmol, 5.0 equiv). Purification by flash chromatography on silica gel gave 10b as a sticky yellow oil (hexanes:EtOAc, 1:1, Rf 0.67; 16.1 mg, 78% yield): [α]25D +68.0 (c 0.44, CHCl3); 1H NMR (400 MHz, CDCl3) δ 7.45-7.32 (overlap, 5H), 5.45 (br s, 1H), 4.75 (d, JAB=16.5 Hz, 1H), 4.61 (d, JAB=16.5 Hz, 1H), 3.57 (br m, 1H), 3.39 (d, JAB=15.8 Hz, 1H), 3.33 (d, JAB=15.8 Hz, 1H), 3.12-2.97 (overlap, 4H), 2.83 (ddd, J=11.3, 5.6, 5.6 Hz, 1H), 2.71 (ddd, J=11.3, 5.8, 5.8 Hz, 1H), 2.63 (dd, JAB=15.8, JAX=10.6 Hz, 1H), 2.49 (br d, JAB=15.8 Hz, 1H), 2.38 (ddd, J=8.4, 5.5, 5.5 Hz, 1H), 2.34-2.20 (overlap, 3H), 2.09 (br s, 1H), 1.26 (d, J=6.0 Hz, 3H), 1.25 (s, 3H), 1.12 (d, J=8.4 Hz, 1H), 0.84 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 156.3, 151.8, 145.6, 140.6, 140.2, 129.1 (2C), 128.5 (2C), 128.1, 124.6, 124.4, 120.7, 70.7, 65.5, 64.2, 51.8, 50.5, 44.5, 41.2, 38.2, 34.5, 32.6, 32.2, 31.6, 26.4, 21.6, 21.3; HRLCMS (ESI) m/z 415.2780 ([M+1]+, 100%) calcd for C28H35N2O 415.2749.
  • 23
  • [ 91-21-4 ]
  • [ 18486-69-6 ]
  • [ 1313884-64-8 ]
YieldReaction ConditionsOperation in experiment
43% Stage #1: 1,2,3,4-tetrahydroisoquinoline; myrtenal With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 48h; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane 4.5. Procedure D: General procedure for reductive amination of myrtenal General procedure: The amine (3.3 mmol) and myrtenal (19, 0.5 g, 3.3 mmol) were mixed with dry DCE (10 mL). If the amine is a salt, TEA (460 μL, 3.3 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (1.06 g, 5.00 mmol) was added and the mixture was stirred at rt for 48 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography.
  • 24
  • [ 712-76-5 ]
  • [ 18486-69-6 ]
  • [ 1313885-06-1 ]
YieldReaction ConditionsOperation in experiment
26% Stage #1: N-(4-phenyl)benzylamine; myrtenal With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 48h; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane for 0.166667h; 4.5. Procedure D: General procedure for reductive amination of myrtenal General procedure: The amine (3.3 mmol) and myrtenal (19, 0.5 g, 3.3 mmol) were mixed with dry DCE (10 mL). If the amine is a salt, TEA (460 μL, 3.3 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (1.06 g, 5.00 mmol) was added and the mixture was stirred at rt for 48 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography.
  • 25
  • [ 564-94-3 ]
  • [ 26177-44-6 ]
  • [ 1313885-03-8 ]
YieldReaction ConditionsOperation in experiment
22% General procedure: The amine (3.3 mmol) and myrtenal (19, 0.5 g, 3.3 mmol) were mixed with dry DCE (10 mL). If the amine is a salt, TEA (460 muL, 3.3 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (1.06 g, 5.00 mmol) was added and the mixture was stirred at rt for 48 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography.
  • 26
  • [ 564-94-3 ]
  • [ 59528-27-7 ]
  • [ 1313884-98-8 ]
YieldReaction ConditionsOperation in experiment
69% General procedure: The aldehyde (1 mmol) and <strong>[59528-27-7]4-iodobenzylamine hydrochloride</strong> (0.270 g, 1 mmol) were mixed with dry DCE (25 mL). If indicated, TEA (139 muL, 1 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (0.318 g, 1.5 mmol) was added and the mixture was stirred at rt for 24-36 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. If required, the crude product was purified by column chromatography.
  • 27
  • [ 18486-69-6 ]
  • [ 104-86-9 ]
  • [ 1313885-02-7 ]
YieldReaction ConditionsOperation in experiment
29% Stage #1: myrtenal; 4-chlorobenzylamine With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 48h; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane for 0.166667h; 4.5. Procedure D: General procedure for reductive amination of myrtenal General procedure: The amine (3.3 mmol) and myrtenal (19, 0.5 g, 3.3 mmol) were mixed with dry DCE (10 mL). If the amine is a salt, TEA (460 μL, 3.3 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (1.06 g, 5.00 mmol) was added and the mixture was stirred at rt for 48 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography.
  • 28
  • [ 18486-69-6 ]
  • [ 156-41-2 ]
  • [ 1313885-05-0 ]
YieldReaction ConditionsOperation in experiment
27% Stage #1: myrtenal; 4-chlorophenylethylamine With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 48h; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane for 0.166667h; 4.5. Procedure D: General procedure for reductive amination of myrtenal General procedure: The amine (3.3 mmol) and myrtenal (19, 0.5 g, 3.3 mmol) were mixed with dry DCE (10 mL). If the amine is a salt, TEA (460 μL, 3.3 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (1.06 g, 5.00 mmol) was added and the mixture was stirred at rt for 48 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography.
  • 29
  • [ 18486-69-6 ]
  • [ 102-49-8 ]
  • [ 1313885-04-9 ]
YieldReaction ConditionsOperation in experiment
24% Stage #1: myrtenal; 3,4-dichlorobenzyl amine With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 48h; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane for 0.166667h; 4.5. Procedure D: General procedure for reductive amination of myrtenal General procedure: The amine (3.3 mmol) and myrtenal (19, 0.5 g, 3.3 mmol) were mixed with dry DCE (10 mL). If the amine is a salt, TEA (460 μL, 3.3 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (1.06 g, 5.00 mmol) was added and the mixture was stirred at rt for 48 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography.
  • 30
  • [ 564-94-3 ]
  • [ 3718-88-5 ]
  • [ 1313884-99-9 ]
YieldReaction ConditionsOperation in experiment
20% General procedure: The amine (3.3 mmol) and myrtenal (19, 0.5 g, 3.3 mmol) were mixed with dry DCE (10 mL). If the amine is a salt, TEA (460 muL, 3.3 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (1.06 g, 5.00 mmol) was added and the mixture was stirred at rt for 48 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography.
  • 31
  • [ 18486-69-6 ]
  • [ 140-75-0 ]
  • [ 1313885-01-6 ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: myrtenal; para-fluorobenzylamine With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 48h; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane for 0.166667h; 4.5. Procedure D: General procedure for reductive amination of myrtenal General procedure: The amine (3.3 mmol) and myrtenal (19, 0.5 g, 3.3 mmol) were mixed with dry DCE (10 mL). If the amine is a salt, TEA (460 μL, 3.3 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (1.06 g, 5.00 mmol) was added and the mixture was stirred at rt for 48 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography.
  • 32
  • [ 18486-69-6 ]
  • [ 100-46-9 ]
  • [ 1313885-00-5 ]
YieldReaction ConditionsOperation in experiment
39% Stage #1: myrtenal; benzylamine With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 48h; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane for 0.166667h; 4.5. Procedure D: General procedure for reductive amination of myrtenal General procedure: The amine (3.3 mmol) and myrtenal (19, 0.5 g, 3.3 mmol) were mixed with dry DCE (10 mL). If the amine is a salt, TEA (460 μL, 3.3 mmol) was added to liberate the parent amine. Next, Na(AcO)3BH (1.06 g, 5.00 mmol) was added and the mixture was stirred at rt for 48 h. Aq NaOH-soln (2 M) was added and the mixture was stirred vigorously for 10 min, after which DCM was added. The organic layer was separated and the aq layer was back-extracted with DCM (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography.
Multi-step reaction with 2 steps 1: methanol 2: sodium tetrahydroborate / methanol
  • 33
  • [ 18486-69-6 ]
  • [ 100-51-6 ]
  • [ 762-72-1 ]
  • (1R,5S)-2-(1-(benzyloxy)but-3-enyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With 50 wt% silicomolybdic acid/SiO2 In acetonitrile at 20℃; for 1h; 4.3. Allylation of carbonyl compounds General procedure: To a solution of benzaldehyde 1 (100 mg, 0.942 mmol) in acetonitrile (2 mL) was added 50 wt % SMA/SiO2 (68 mg, 0.018 mmol). Then benzyl alcohol (195 μL, 1.88 mmol) and allyltrimethylsilane (0.449 mL, 2.82 mmol) were added dropwise at ambient temperature. The reactants were stirred for a further 5 min. After the completion of reaction (TLC), brine (10 mL) was added and the reaction mixture was extracted with ether (2×10 mL). The combined ether layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the crude product by column chromatography afforded pure homoallylic benzyl ether 1a as a colorless oil (222 mg, 99%).
  • 34
  • [ 558-37-2 ]
  • [ 18486-69-6 ]
  • [ 1326316-67-9 ]
YieldReaction ConditionsOperation in experiment
91% With 3-methylpyridin-2-ylamine; Wilkinson's catalyst; 4-trifluoromethylbenzoic acid In toluene at 150℃; for 1h;
  • 35
  • [ 109-67-1 ]
  • [ 18486-69-6 ]
  • [ 1326316-68-0 ]
YieldReaction ConditionsOperation in experiment
86% With 3-methylpyridin-2-ylamine; Wilkinson's catalyst; 4-trifluoromethylbenzoic acid In toluene at 150℃; for 1h;
  • 36
  • [ 111-66-0 ]
  • [ 18486-69-6 ]
  • [ 1326316-69-1 ]
YieldReaction ConditionsOperation in experiment
82% With 3-methylpyridin-2-ylamine; Wilkinson's catalyst; 4-trifluoromethylbenzoic acid In toluene at 150℃; for 1h;
  • 37
  • [ 558-13-4 ]
  • [ 18486-69-6 ]
  • C11H14Br2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: myrtenal In dichloromethane at 0 - 23℃; for 2h; Inert atmosphere;
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.25h; Stage #2: myrtenal In dichloromethane at 0℃; for 0.55h;
  • 38
  • [ 50-00-0 ]
  • [ 19902-08-0 ]
  • [ 34413-88-2 ]
  • [ 18486-69-6 ]
  • trans-pinocarveol [ No CAS ]
  • [ 30293-06-2 ]
  • [ 35836-73-8 ]
  • [ 19894-97-4 ]
YieldReaction ConditionsOperation in experiment
With sulfated zinc ferrite In toluene at 95℃; for 12h; In a typical Prins condensation reaction, β-pinene (5 mmol), paraformaldehyde (15 mmol) in toluene (4 ml) with 0.14 g pre-activated SZF catalyst was refluxed at 95 °C in the RB flask with continuous stirring. The aliquots of reaction mixture were collected periodically, cooled and centrifuged to separate the catalyst. The reaction products were analyzed by gas chromatograph (Varian GC-450), equipped with Factor-4 capillary column (30 m long and 0.32 mm internal diameter) and flame ionization detector. The oven temperature was increased from 80 °C to 220 °C at the rate of 10 °C/min. High purity nitrogen gas was used (30 ml/h flow rate) as a carrier gas for the analysis.
  • 39
  • [ 18486-69-6 ]
  • [ 24470-78-8 ]
  • [ 1421320-34-4 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: isopropyltriphenylphosphonium iodide With sodium amide In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Stage #2: myrtenal In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
82% Stage #1: isopropyltriphenylphosphonium iodide With sodium amide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: myrtenal In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
With sodium amide In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
  • 40
  • [ 18486-69-6 ]
  • [ 62-53-3 ]
  • N-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% In methanol for 2h; N-(((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)aniline (imine (1)) was synthesized from (-)-myrtenaland aniline. (-)-Myrtenal (0.15 g, 0.1 mmol) was added to a solu-tion of aniline (0.093 g, 0.1 mmol) in methanol (3 ml). The mixturewas stirred for 2 h, and then the solvent was distilled off, givingimine (1) (0.216 g (95%)).1H NMR and13C NMR spectra of imine(1) were in good agreement with the ones described earlier [16].
94% In methanol
In methanol 2.1.2. General Procedure for (30)-(51) General procedure: Amines (15)-(29) were added into a solution (5 ml) of the corresponding monoterpene aldehydes (11)-(14) in methanol in equimolar amounts. The reaction mixture was stirred until the reaction was complete. Then six fold excess of sodium borohydride was added. After the end of gas evaluation methanol was distilled off, brine was added, and the amines (30)-(51) were extracted with diethyl ether. The organic layer was dried under sodium sulfate and evaporated. Amines (36)-(47), (51) were purified by silica gel column chromatography. Amines (39)-(41), (44), (45) were additionally treated with diethyl ether saturated by hydrochloric acid. The solid was washed three times with hexane and then 5 wt% NaOH solution was added. The amines were extracted by hexane and organic layer was dried under sodium sulfate and then evaporated to give (39)-(41), (44), (45). All amines (30)-(51) were obtained as oils.
  • 41
  • [ 18486-69-6 ]
  • [ 665-66-7 ]
  • C20H29N [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In methanol at 20℃; for 1.5h; N-(3,7-dimethylocta-2,6-dien-1-yl)adamantan-1-amine (11a,b). General procedure General procedure: Triethylamine (0.200 g, 1.96 mmol), and citral (6) (0.200 g, 1.30 mmol) were added to a solution of 1-adamantylamine hydrochloride (1) (0.200 g, 1.07 mmol) in methanol (3 mL). The mixture was stirred for 5 h, then the solvent was distilled off and the residue was suspended in hexane (15 mL). The suspension was filtered, precipitation was discarded and hexane was evaporated from the filtrate. The residue was dissolved in methanol (3 mL), and then sodium borohydride powder (0.205 g, 5.39 mmol) was added to the solution. The resulting suspension was stirred at room temperature for 12 h, then methanol was distilled off and the residue was suspended in brine (20 mL). The solution was treated with ethyl acetate (3×15 mL), combined organic solutions were driedover Na2SO4, then drying agent was filtered off and the solvent was distilled off. This gave a mixture of compounds 11a,b (0.192 g (63%)).
With triethylamine In methanol
  • 42
  • [ 18486-69-6 ]
  • [ 10523-68-9 ]
  • N-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methylene}adamantan-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine In methanol for 0.333333h; Reflux; N-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methylene}adamantan-2-amine (15) Compound 15 was synthesized according to the described procedure [13]. Triethylamine (0.175 g, 1.73 mmol)and (-)-myrtenal (7) (0.296 g, 1.97 mmol) were added to the solution of 2-adamantylamine hydrochloride (5) (0.300 g, 1.60 mmol) in methanol (2 mL). The reaction mixture was heated under reflux for 20 minutes, and then cooled to room temperature. The precipitation formed was filtered, washed with cold methanol and dried on air. This gave compound 15 (0.323 g (71%)).
With triethylamine In methanol
  • 43
  • [ 123-75-1 ]
  • [ 18486-69-6 ]
  • [ 1542139-53-6 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: myrtenal With trimethylsilyl cyanide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 50℃; for 5h; Inert atmosphere; Stage #2: pyrrolidine In tetrahydrofuran at -20℃; for 12h; Inert atmosphere;
  • 44
  • [ 18486-69-6 ]
  • [ 5802-60-8 ]
  • (E)-1,1-dibenzyl-2-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hep-2-en-2-yl)methylene)hydrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere; Sealed tube;
  • 45
  • [ 1785-61-1 ]
  • [ 18486-69-6 ]
  • C30H34O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With lithium hexamethyldisilazane In tetrahydrofuran at -50 - 20℃; for 5h;
  • 46
  • [ 935-14-8 ]
  • [ 18486-69-6 ]
  • C30H34O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With lithium hexamethyldisilazane In tetrahydrofuran at -50 - 20℃; for 3h;
  • 47
  • [ 18486-69-6 ]
  • [ 95091-91-1 ]
  • C17H17NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: myrtenal; N-methoxy-N-methylpyridine-3-carboxamide With carbon tetrabromide; triethylamine; triphenylphosphine Stage #2: N-methoxy-N-methylpyridine-3-carboxamide With lithium diisopropyl amide
  • 48
  • [ 18486-69-6 ]
  • 1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one oxime [ No CAS ]
  • 2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-5,7-dimethyl-1,3-diazaadamantan-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% In methanol at 20℃; for 2h; Synthesis of diazaadamantanes (Va-e). General procedure: A mixture of aldehyde (VIa)-(VId) (0.360.4 mmole) and equimolar amount of 1,5dimethylbispidine-9-one (IV) dissolved in metanol (2 ml) was stirred at room temperature until full conversion. The solvent was removed under reduced pressure. The residue was purified by chromatography on 3 g silica gel column (1 × 18 cm). 2[(1S,5R)6,6Dimethylbicyclo[3.1.1]hept2en2yl]5,7dimethyl1,3diazaadamantan6one (Va).The time of the reaction is 2 h. Yield 54%. = -22(c 0.4). Mass spectrum: m/z 300.2196 [M+]. Calcd.M 300.2196 (C19H28N2O). 1H NMR spectrum: 0.79(s, 3H) and 0.89 (s, 3H) (C11H3 and C12H3), 0.88 (s,3H, C21H3), 1.14 (d, 1H, 2J 8.0, H19anti), 1.28 (s,3H, C20H3), 2.09-2.14 (m, 1H, H16), 2.30 (dddd,1H, 2J 18.0, J15,14 = J15,16 = J15,2 = 3.0, H15), 2.37(dddd, 1H, 2J 18.0, J15',14 = J15',16 = J15',2 = 3.0, H15'),2.42-2.47 (m, 2H, H18, H19sin), 2.68-2.75 (m, 2H,NCH2), 3.08-3.16 (m, 2H, NCH2), 3.26-3.33 (m,3H, NCH2), 3.45 (dd, 1H, 2J 13.2, 4J 3.3, NCH2), 4.35(m,1H, all J ≤ 3.5, H2), 5.72 (m, 1H, all J ≤ 3.5, H14).13C NMR spectrum: 79.33 (d, C2), 59.95, 60.51,67.60, 67.40 (t, C4, C8, C9, C10), 45.61, 45.89 (s, C5, C7), 212.31 (s, C6), 15.82, 16.31 (q, C11, C12),144.28 (s, C13), 120.97 (d, C14), 31.38 (t, C15), 40.86(d, C16), 37.60 (s, C17), 41.58 (d, C18), 31.83(t, C19), 26.14 (q, C20), 21.02 (q, C21).
  • 49
  • N-[2-oxo-2-(6-terpyridinyl)ethyl]pyridinium iodide [ No CAS ]
  • [ 18486-69-6 ]
  • 4,5-[(1R,5R)(pineno)]-2,2’:6’,2”:6”,2”’-quaterpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With ammonium acetate In formamide at 80℃; Typical synthesis General procedure: Pyridinium salt 5 (240 mg, 0.5 mmol) and ammonium acetate (150 mg, 2 mmol) were suspended in formamide (2 mL). After the addition of the enone in excess (3 equiv) and heating at 80 °C, solubilisation was observed, then a precipitate appeared soon. Heating was maintained overnight. After cooling down, the precipitate was filtered off, rinsed with distilled water and dried under vacuum.
  • 50
  • [ 18486-69-6 ]
  • [ 108-98-5 ]
  • (1S,2R,3S,5R)-6,6-dimethyl-2-formyl-3-(phenylsulfanyl)bicyclo[3.1.1]heptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With pyridine In neat (no solvent) at 0℃; for 72h; Inert atmosphere; diastereoselective reaction; 1 4.2 General procedure for the Michael addition reactions General procedure: To a solution of (1R)-(-)-myrtenal 1 (0.90g, 6.0mmol) and dry pyridine (1mL, 2.0equiv), the appropriate thiophenol (2.5equiv) was added under an argon atmosphere. The reaction mixture was stirred at 0°C for 3 days, then diluted with CH2Cl2 (15mL) and quenched with 1N HCl (10mL). The organic phase was washed with 10% NaOH, water, brine, dried over Na2SO4, and the solvent was evaporated. The crude product was chromatographed on a silica gel using CH2Cl2/n-hexane (2:1 v/v), yielding a light yellow oil (-)-2. 4.2.1 (1S,2R,3S,5R)-6,6-Dimethyl-2-formyl-3-(phenylsulfanyl)bicyclo[3.1.1]heptane (2a) Yield 88%, Rf=0.38 (CH2Cl2/n-hexane, 2:1), [α]D20=-32.4 (1.02, CH2Cl2). 1H NMR (300MHz, CDCl3): δ=0.70 (s, 3H), 1.22 (s, 3H), 1.47 (d, J=10.1Hz, 1H), 1.98 (sept, J=2.8Hz, 1H), 2.06 (dt, J=14.4, 3.8Hz, 1H), 2.41-2.46 (m, 1H), 2.48-2.53 (m, 1H), 2.54-2.61 (m, 1H), 2.87 (dd, J=5.1, 3.0Hz, 1H), 4.25 (ddd, J=9.6, 5.0, 4.1Hz, 1H), 7.24-7.32 (m, 3H), 7.45-7.48 (m, 2H), 9.53 (s, 1H). 13C NMR (75MHz, CDCl3): δ=23.2, 26.5, 29.6, 34.1, 34.9, 38.6, 41.2, 42.4, 61.0, 127.5, 129.1 (2C), 132.4 (2C), 135.1, 202.4. IR (film): 2922, 1725, 1584, 1480, 1438, 748, 692cm-1. HRMS (ESI): calcd for [C16H20OS+H]+: 261.1308; found 261.1326.
  • 51
  • [ 18486-69-6 ]
  • [ 106-45-6 ]
  • (1S,2R,3S,5R)-6,6-dimethyl-2-formyl-3-((4-methyl)phenylsulfanyl)bicyclo[3.1.1]heptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With pyridine In neat (no solvent) at 0℃; for 72h; Inert atmosphere; diastereoselective reaction; 2 4.2 General procedure for the Michael addition reactions General procedure: To a solution of (1R)-(-)-myrtenal 1 (0.90g, 6.0mmol) and dry pyridine (1mL, 2.0equiv), the appropriate thiophenol (2.5equiv) was added under an argon atmosphere. The reaction mixture was stirred at 0°C for 3 days, then diluted with CH2Cl2 (15mL) and quenched with 1N HCl (10mL). The organic phase was washed with 10% NaOH, water, brine, dried over Na2SO4, and the solvent was evaporated. The crude product was chromatographed on a silica gel using CH2Cl2/n-hexane (2:1 v/v), yielding a light yellow oil (-)-2.
  • 52
  • [ 18486-69-6 ]
  • [ 2396-68-1 ]
  • (1S,2R,3S,5R)-6,6-dimethyl-2-formyl-3-((4-tert-butyl)phenylsulfanyl)bicyclo[3.1.1]heptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With pyridine In neat (no solvent) at 0℃; for 72h; Inert atmosphere; diastereoselective reaction; 3 4.2 General procedure for the Michael addition reactions General procedure: To a solution of (1R)-(-)-myrtenal 1 (0.90g, 6.0mmol) and dry pyridine (1mL, 2.0equiv), the appropriate thiophenol (2.5equiv) was added under an argon atmosphere. The reaction mixture was stirred at 0°C for 3 days, then diluted with CH2Cl2 (15mL) and quenched with 1N HCl (10mL). The organic phase was washed with 10% NaOH, water, brine, dried over Na2SO4, and the solvent was evaporated. The crude product was chromatographed on a silica gel using CH2Cl2/n-hexane (2:1 v/v), yielding a light yellow oil (-)-2.
  • 53
  • [ 18486-69-6 ]
  • [ 106-40-1 ]
  • 4-bromo-N-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: myrtenal; 4-bromo-aniline In methanol for 3h; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 12h; 4-bromo-N-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)aniline was synthesized from (-)-myrtenal and4-bromoaniline. (-)-Myrtenal (0.155 g, 1.03 mmol) was added toa solution of p-bromoaniline (0.175 g, 1.02 mmol) in methanol(3 ml). The mixture was stirred for 3 h, then sodium borohy-dride powder (0.236 g, 6.24 mmol) was added to the solution.The resulting suspension was stirred at room temperaturefor 12 h, then methanol was distilled off and the residue wassuspended in brine (15 ml). The solution was treated withethyl acetate (3 × 15 ml), combined organic solutions weredried over Na2SO4, then drying agent was filtered off andthe solvent was distilled off, giving 4-bromo-N-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)aniline (0.310 g(98%)).
Multi-step reaction with 2 steps 1: methanol 2: sodium tetrahydroborate / methanol
  • 54
  • [ 18486-69-6 ]
  • [ 125658-08-4 ]
  • N-[{(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-y}methyl]-5,7-dimethyl-1,3-diazaadamantan-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: myrtenal; 5,6-Dimethyl-6-amino-1,3-diazaadamantane In methanol at 20℃; for 3h; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 1.5h; 3.3. Reaction of Amine 14 with Aldehydes 8a-d: GeneralProcedure General procedure: A solution of amine 14 in methanol (4 mL) was addedunder stirring to the corresponding aldehyde. After 3 hours NaBH4 was added to reaction mixture and stirred for an additional 1.5 hours, then the reaction mixture was treated with8 ml of saturated NaCl solution and allowed to stand for 30 minutes. The product was extracted with ether (6x10 ml).Isolation of amines 15a-d from the reaction mixture wasaccomplished by precipitation from solution in ether in theform of hydrochloric salts by adding to a solution of ethylacetatesaturated with hydrogen chloride. The precipitatewas filtered off, washed with ether and treated with saturatedsodium bicarbonate solution. The product was extractedfrom the aqueous solution with ether.
79% Stage #1: myrtenal; 5,6-Dimethyl-6-amino-1,3-diazaadamantane In methanol for 4h; Stage #2: With sodium tetrahydroborate In methanol for 1.5h; Synthesis of compounds 8a, c-e: general procedure General procedure: Secondaryamines 8a, - was synthesized by the procedure 4. To a solution of amine 14 (0.1 mmol) in 4 mL of MeOH was addedequimolar amount of aldehydes 12a, - and mixture was stirred for 4 h. NaBH4 (0.6mmol) was added to a mixture and solution was stirred 1.5 h more. The solventwas distilled off and 8 ml of saturated solution of NaCl was added to a residue.The product was extracted with ether Et2O (6x10 ml). Isolationof amines 8a, - from the reaction mixture was accomplished byprecipitation from solution in ether in the form of hydrochloric salts byadding to a solution of ethyl acetate saturated with hydrogen chloride. Theprecipitate was filtered off, washed with ether and treated with saturatedsodium bicarbonate solution. The product was extracted from the aqueoussolution with ether. Organic phase was dried under Na2SO4.The desiccant was filtered off and the solvent was distilled off on a rotaryevaporator. 1H and 13 NMR spectra of synthesized
  • 55
  • [ 18486-69-6 ]
  • 1,5-dimethyl-9-oxo-3,7-diazabicyclo-<3.3.1>nonane dihydrochloride [ No CAS ]
  • 2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-5,7-dimethyl-1,3-diazaadamantan-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine In methanol Synthesis ofcompounds 7a-g: general procedure General procedure: Compounds7a-g was synthesized by theprocedure[i]. A mixture of hydrochloride 11 (0.1 mmol), equimolar amount ofaldehydes 12a-g and 2.5 equivalentsof triethylamine was dissolved in a 2-ml portion of methanol. After completionof the reaction (control with gas chromatography), the solvent was distilledoff, and the residue was separated on a SiO2 column.
  • 56
  • [ 18486-69-6 ]
  • [ 100-58-3 ]
  • (1R)-10-epi-phenylmyrtenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In tetrahydrofuran at -78℃; for 5h; Inert atmosphere; 4.10 (1R)-10-epi-Phenylmyrtenol To a cooled solution (-78°C) of 7.43g (49.5mmol) of (1R)-myrtenal in 50mL of anhydrous THF, 1.5equiv of PhMgBr were added and the resulting mixture was stirred at the same temperature for 5h under an N2 atmosphere. The crude reaction mixture was poured into ice-water and extracted (3×100mL) with ether, washed with brine, dried with anhydrous Na2SO4, filtered, and evaporated to dryness. The residue was purified by column chromatography (hexanes-EtOAc 98:2) giving 11.8g (98%) of 10-epi-phenylmyrtenol as colorless syrup. (Rf 0.37, hexanes-AcOEt 9:1). 1H NMR (CDCl3): δ 7.26 (5H, m, H-Ar), 5.56 (1H, m, H-3), 5.05 (1H, bs, H-10), 2.29 (3H, m, H-4, H-7eq), 2.18 (1H, s, -OH), 2.05 (2H, m, H-1, H-5), 1.17 (3H, s, Me-9), 1.07 (1H, d, J=8.5Hz, H-7ax), 0.71 (3H, s, Me-8). 13C NMR (CDCl3): δ 149.7 (C-ipso), 141.9 (C-2), 128.3 (C-ortho), 126.9 (C-para), 126.6 (C-meta), 119.0 (C-3), 76.7 (C-10), 42.5 (C-1), 40.9 (C-5), 37.9 (C-6), 32.1 (C-4), 31.5 (C-7), 26.2 (C-9), 21.5 (C-8). IR (CHCl3): 3392, 3028, 2989, 2915, 2831, 1636, 1450, 1365, 1267, 1079, 1047, 1017, 753, 700cm-1. MS m/z (rel. int.): 228 (M+, 3), 228 (30), 211 (100), 210 (58), 195 (12), 184 (12), 168 (15), 167 (32), 155 (11), 141 (11), 107 (12), 105 (20), 91 (16), 79 (19). HRFABMS calcd for C16H20O 228.1514. Found 228.1521.
  • 57
  • [ 18486-69-6 ]
  • 1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonane hydrochloride [ No CAS ]
  • 2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-5,7-dimethyl-1,3-diazaadamantane [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With triethylamine In methanol for 7h; 2-(6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)-5,7-dimethyl-1,3-diazaadamantane (17). 1,5-Dimethylbispidinehydrochloride 21 (500 mg, 2.20 mol) was treated with (-)-myrtenal (13a, 340 mg, 2.27 mmol) in MeOH (6 mL) and Et3N(450 mg) and stored for 7 h. The solvent was distilled off. The mixture was separated by column chromatography in twobatches over SiO2 (11.65 g) to afford the product (82 mg, 13%), 58923-24.16 (c 0.50, MeOH). 1 NMR spectrum(500 MHz, CDCl3, , ppm, J/Hz): 0.56, 0.65 (3 each, s, 3-11, 12), 0.82 (3, s, 3-21), 1.09 (1, d, J = 8.0, -19), 1.23(3H, m, CH3-20), 1.42 (2, br.s, -6), 2.05 (1, ddddd, J = 5.6, 5.6, 3.0, 3.0, 1.3, -16), 2.24 (1, dm, J = 17.9, other J 3.0,-15), 2.32 (1, dm, J = 17.9, other J 3.0, -15), 2.34-2.40 (2, m, -18, 19), 4N-CH2: 2.45-2.50 (2, m), 2.88 (1, dd,J = 12.8, 3.1), 2.91 (2, dd, J = 13.2, 3.1), 2.98 (2, br.d, J 13.0), 3.08 (1, br.d, J = 13.2); 4.21-4.24 (1, m, -2),5.64-5.68 (1H, m, H-14). 13C NMR spectrum (125 MHz, CDCl3, , ppm): 79.37 (CH, -2), 56.36, 56.99, 64.57, 64.68 (4CH2,C-4, 8, 9, 10), 26.14, 26.23 (2C, C-5, 7), 49.57 (CH2, -6), 23.86, 24.41 (2CH3,C-11, 12), 144.39 (C, -13), 120.44 (CH,-14), 31.35 (CH2, -15), 40.73 (CH, -16), 37.51 (C, -17), 41.54 (CH, -18), 31.77 (CH2, -19), 26.06 (CH3, -20),20.92 (CH, -21). Found m/z 286.2409 (M)+, calcd for C19H30N2, 286.2409.
  • 58
  • [ 18486-69-6 ]
  • C11H20N2O*2ClH [ No CAS ]
  • 2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-5,7-diethyl-1,3-diazaadamantan-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine In methanol for 3h; 2-(6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)-5,7-diethyl-1,3-diazaadamantan-6-one (14a). Bispidinone 11(73 mg, 0.27 mmol) was treated with (-)-myrtenal (13a, 43 mg, 0.28 mmol) in MeOH (4 mL) and Et3N (60 mg), stored for3 h, and evaporated. The products were separated by column chromatography. Yield of 14a, 65 mg (73%), 58925 -20.92(c 1.00, MeOH). 1 NMR spectrum (500 MHz, CDCl3, , ppm, J/Hz): 0.79, 0.86 (3 each, t, J = 7.6, 3-12, 14), 0.87 (3H,s, CH3-23), 1.13 (1, d, J = 8.0, -21), 1.28 (3, s, 3-22), 1.30, 1.40 (2H each, q, J= 7.6, -11, 13), 2.11 (1, ddddd,J = 5.6, 5.6, 2.8, 2.8, 1.4, -18), 2.29 (1, dm, J = 18.0, other J 3.0, -17a), 2.37 (1, dm, J = 18.0, other J 3.0, -17b),2.41-2.48 (2, m, -20, 21), 4N-CH2: 2.66-2.74 (2, m), 3.08-3.16 (2, m), 3.28-3.34 (3, m), 3.48 (1, dd, J = 13.1,3.3); 4.34 (1, m, all J 3.5, -2), 5.71-5.74 (1, m, -16). 13C NMR spectrum (125 MHz, CDCl3, , ppm): 79.79 (CH2,C-2), 57.61, 58.15, 65.13, 65.31 (4CH2, C-4, 8, 9, 10), 47.89, 48.21 (2C, C-5, 7), 211.99 (C, C-6), 23.39, 23.80 (2CH2, C-11,13), 7.20, 7.43 (2CH3, C-12, 14), 144.38 (C, C-15), 120.93 (CH, C-16), 31.37 (CH2, C-17), 40.85 (CH, C-18), 37.57 (C,C-19), 41.53 (CH, C-20), 31.86 (CH2, C-21), 26.13 (CH3, C-22), 21.09 (CH3, C-23). Found m/z 328.2511 (M)+, calcd forC21H32N2O, 328.2515.
  • 59
  • [ 18486-69-6 ]
  • 1,5-dipropyl-3,7-diazabicyclo[3.3.1]nonan-9-one dihydrochloride [ No CAS ]
  • 2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-5,7-dipropyl-1,3-diazaadamantan-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With triethylamine In methanol for 3h; 2-(6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)-5,7-dipropyl-1,3-diazaadamantan-6-one (15a). Compound 12(85 mg, 0.29 mmol) was treated with (-)-myrtenal (13a, 40 mg, 0.27 mmol) in MeOH (5 mL) and Et3N (70 mg), stored for3 h, and evaporated. The mixture was separated by column chromatography. Yield of 15a, 56 mg (58%), 58925 -19.43(c 0.99, MeOH). 1 NMR spectrum (500 MHz, CDCl3, , ppm, J/Hz): 0.87, 0.91 (3 each, t, J = 6.8, 3-13, 16), 0.88 (3H,s, CH3-25), 1.14 (1, d, J = 8.2, -23), 1.18-1.34 (8, m, -11, 12, 14, 15), 1.29 (3, s, C3-24), 2.12 (1, ddddd, J = 5.8,5.8, 3.0, 3.0, 1.3, -20), 2.30 (1, dddd, J = 18.0, 3.0, 3.0, 3.0, -19), 2.38 (1, dddd, J = 18.0, 3.0, 3.0, 3.0, -19a),2.42-2.47 (2, m, -22, 23), 4N-CH2: 2.67-2.74 (2, m), 3.09-3.17 (2, m), 3.30-3.35 (3, m), 3.50 (1, dd, J = 13.0,3.2); 4.33-4.36 (1, m, H-2), 5.70-5.74 (1, m, H-18). 13C NMR spectrum (125 MHz, CDCl3, , ppm): 79.83 (CH, C-2),113558.04, 58.60, 65.57, 65.76 (4CH2, C-4, 8, 9, 10), 48.14, 48.45 (2C,C-5, 7), 212.13 (C, C-6), 33.18, 33.62 (2CH2, C-11, 14),16.02, 16.28 (2CH2, C-12, 15), 14.87, 14.92 (2CH3, C-13, 16), 144.44 (C, C-17), 120.90 (CH, C-18), 31.39 (CH2, C-19),40.88 (CH, C-20), 37.60 (C, C-21), 41.57 (CH2, C-22), 31.89 (CH3, C-23), 26.15 (CH3, C-24), 21.11 (CH3, C-25). Foundm/z 356.2834 (M)+, calcd for C23H36N2O, 356.2828.
  • 60
  • [ 18486-69-6 ]
  • [ 108-00-9 ]
  • C14H24N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With sodium sulfate In benzene at 20℃; for 5h; Schlenk technique; Synthesis of the Schiff base ligand (2) A solution of 0.1 g (0.9 mmol) of (1R,5S)-(-)-myrtenal (1) and 0.1 g(0.9 mmol) of N,N-dimethylethylenediamine in 5 mL of anhydrousbenzene was stirred for 5 h at room temperature in the presence of 1 gof anhydrous sodium sulfate. The mixture was filtered, the precipitatewas washed with benzene, and the solvent was removed from the filtrateunder reduced pressure to isolate 0.2 g (98%) of imine 2. Yellowoil, [α]D24 -9.4 (c 0.2, CHCl3). FT-IR: ν(C]N) 1633 cm-1. 1H NMR(300 MHz, CDCl3, δ, ppm): 0.85 (s, 3H, CH3-9), 1.19 (d, 1H, Hα-7,J=8.6 Hz), 1.31 (s, 3H, CH3-8), 2.15 (m, 1H, H-5), 2.25 (s, 6H, CH3-13,14), 2.47 (m, 3H, Hα-4, Hβ-4, Hβ-7), 2.55 (m, 2H, H-12), 2.99 (m,1H, H-1), 3.56 (m, 2H, H-11), 6.05 (m, 1H, H-3), 7.92 (s, 1H, H-10). 13CNMR (75 MHz, CDCl3, δ, ppm): 20.89 (C(9)), 25.91 (C(8)), 31.33(C(7)), 32.34 (C(4)), 37.59 (C(6)), 40.06 (C(1)), 40.95 (C(5)), 45.86(C(13,14)), 59.68 (C(11)), 60.28 (C(12)), 134.23 (C(3)), 148.26 (C(2)),162.87 (C(10)).
In toluene for 72h; Reflux; Synthesis of (L). A 100 mL round-bottomed flask was charged with (1R)-myrtenal (3.000 g, 20.00 mmol) and N1,N1-dimethylenthylene-1,2-diamine (1.760 g 20.00 mmol) and toluene as solvent. The mixture was refluxed for 3 days. A crude imine as a waxy solid was obtained after remove of solvent. Methanol (100 mL) solution of the diimine (4.400 g)was treated with NaBH4 (1.133 g, 30.00 mmol) at 0 C. Solvent was removed and the crude product was treated water and CH2Cl2. Separated organic phase was dried over MgSO4 and removing solvent afforded brown sticky oil as the product (3.83 g, 86% yield).
  • 61
  • [ 18486-69-6 ]
  • [ 1137-94-6 ]
  • (6R,8R)-7,7-dimethyl-3-phenyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 1-(2-phenyl-2-oxoethyl)pyridinium iodide With ammonium acetate In formamide at 50℃; for 0.5h; Stage #2: myrtenal In formamide at 100℃; for 12h;
With ammonium acetate In formamide
With ammonium acetate; formamide
  • 62
  • [ 18486-69-6 ]
  • C20H28 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: myrtenal With zinc-copper couple; titanium tetrachloride In 1,2-dimethoxyethane for 13h; Sonication; Inert atmosphere; Stage #2: In 1,2-dimethoxyethane for 48h; Reflux; 4.2.4 Triene 14 The procedure was adapted from previous conditions reported by McMurry and co-workers (J.Org. Chem. 1978, 43, 3255.) A flame-dried 1L three-necked flask equipped with a large stir bar and reflux condenser was charged with freshly prepared Zn-Cu couple (44g, 0.67mol, 40 equiv). The system was evacuated and backfilled with argon three times. DME (600mL) was added, followed by the dropwise addition of freshly distilled TiCl4 (24mL, 200mmol, 10 equiv) to the rapidly stirring slurry. After 1h of sonication, the mixture was heated to reflux for 5h, cooled to room temperature, and a solution of myrtenal (3.0g, 20mmol, 1 equiv) in 50mL of degassed DME was added slowly over 12h via syringe pump. After 1h of additional sonication, the reaction mixture was heated at reflux for 48h, cooled to room temperature, and filtered through a pad of Florisil eluting with diethyl ether. This filtration was repeated to give a clear solution that was concentrated in vacuo and purified by flash column chromatography (200:1 hexanes:Et3N) to afford 14 (1.41g, 53% yield) as a colorless oil: [α]20D=+31.70° (c 0.010g/mL, CHCl3); 1H NMR (500MHz, CDCl3) δ 6.14 (s, 2H), 5.53 (m, 2H), 2.62 (ddd, J=5.7, 5.7, 1.6Hz, 2H), 2.42 (ddd, J=8.8, 5.7, 5.7Hz, 2H), 2.39 (ddd, J=19.2, 3.0, 3.0Hz, 2H), 2.32 (ddd, J=19.2, 2.7, 2.7Hz, 2H), 2.12 (m, 2H), 1.33 (s, 6H), 1.13 (d, J=8.8Hz, 2H), 0.81 (s, 6H); 13C NMR (150MHz, CDCl3) δ 146.9, 126.4, 123.7, 41.3, 41.2, 37.9, 32.2, 31.6, 26.6, 21.0; IR (thin film, cm-1) 2931, 2360, 1705, 1650, 1628, 1369, 1331; HRMS (EI) calcd. for [C20H28]: m/z 268.2191, found 268.2191.
  • 63
  • [ 564-94-3 ]
  • [ 15430-52-1 ]
  • (6R,8R)-4,7,7-trimethyl-5,6,7,8-tetrahydro-6,8-methyleneisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In chlorobenzene; at 100℃; for 12h;Inert atmosphere; Sealed tube; Green chemistry; Add magnetic particles, a small amount of magnesium sulfate to the sealing tube, replace argon, and add 2mL of chlorobenzene in sequence under argon protection conditions.Lintao aldehyde (150 mg, 1 mmol), <strong>[15430-52-1]propargylamine hydrochloride</strong> (10 mg, 1. lmmol) and DBU (320 mg, 2.1 mmol) will be sealedAt 100 C. After reacting for 12 h, the solvent was separated and purified by silica gel column chromatography to give a white solid.The yield was 82%.The specific reaction equation is:
  • 64
  • [ 18486-69-6 ]
  • [ 50329-23-2 ]
  • (6R,8R)-4-ethyl-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methyleneisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In chlorobenzene at 100℃; for 12h; Inert atmosphere; Sealed tube; Green chemistry; 8 Example 8 Preparation of (6R,8R)-4-Ethyl-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methylenequinoline Add magnetic particles, a small amount of magnesium sulfate to the sealing tube, replace argon, and add 2mL of chlorobenzene in sequence under argon protection conditions.After the camphor aldehyde (150mg, 1mmol), 2-butynylamine hydrochloride (117mg, 1 · lmmol) and DBU (320mg, 2. lmmol)Tube at 100 ° C. After reacting for 12 h, the solvent was separated and purified by silica gel column chromatography to give a white solid.The yield was 72%.The specific reaction equation is:
72% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In chlorobenzene at 100℃; for 12h; Inert atmosphere; Sealed tube;
  • 65
  • [ 18486-69-6 ]
  • 4-benzyloxybutynylamine hydrochloride [ No CAS ]
  • (6R,8R)-4-(2-(benzyloxy)ethyl)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methyleneisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In chlorobenzene at 100℃; for 12h; Inert atmosphere; Sealed tube; Green chemistry; 13 Example 13 Preparation of (6R,8R)-4-(2-(benzyloxy)ethyl)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methyleneisoquinoline Add magnetic particles, a small amount of magnesium sulfate to the sealing tube, replace argon, and add 2mL of chlorobenzene in sequence under argon protection conditions.The citronellal aldehyde (150 mg, 1 mmol), 4-hydroxybutynylamine hydrochloride (233 mg, 1 · 1 mmol) and DBU (320 mg, 2.1 mmol) were then sealed at 100 °C. After reacting for 12 h, the solvent was separated and purified by silica gel column chromatography to give a white solid.The yield was 95%.The specific reaction equation is:
95% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In chlorobenzene at 100℃; for 12h; Inert atmosphere; Sealed tube;
  • 66
  • [ 18486-69-6 ]
  • 4-benzoyloxy-2-butynylamine hydrochloride [ No CAS ]
  • (6R,8R)-7,7-dimethyl-4-vinyl-5,6,7,8-tetrahydro-6,8-methyleneisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In chlorobenzene at 100℃; for 12h; Inert atmosphere; Sealed tube; Green chemistry; 10 Example 10 Preparation of (6R,8R)-7,7-dimethyl-4-vinyl-5,6,7,8-tetrahydro-6,8-methylenequinoline Add magnetic particles, a small amount of magnesium sulfate to the sealing tube, replace argon, and add 2mL of chlorobenzene in sequence under argon protection conditions.Toon aldehyde (150 mg, 1 mmol), 4-benzoyloxy-2-butynylamine hydrochloride (248 mg, 1. lmmol) and DBU (320 mg,After 2.1mm0l), the tube will be sealed at 100 °C. After reacting for 12 h, the solvent was separated and purified by silica gel column chromatography to give a white solid.The yield was 81%.The specific reaction equation is:
  • 67
  • [ 18486-69-6 ]
  • [ 100-36-7 ]
  • N1,N1-diethyl-N2-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylene)ethane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In methanol for 96h; Reflux; 2.3.3 Synthesis of LC N,N-Diethylethylene-diamine (2.32g, 20.0mmol) was refluxed with 1equiv. of (1R)-(-)-myrtenal (3.00g, 20.0mmol) in MeOH (50mL) for 4days. MeOH was eliminated by evaporation and the resultant product was washed with H2O (2×15mL) and CH2Cl2 (2×40mL). The organic phase was dried over MgSO4 and concentrated to get final imine product as yellow oil (4.28g, 86%). Further reduction of imine moiety was carried out as follows; N1,N1-diethyl-N2-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl) methylene)ethane-1,2-diamine (4.28g, 17.22mmol) was treated with 1.5equiv. of NaBH4 (0.98g, 25.84mmol) in MeOH (40mL) for 12h at room temperature. The MeOH was evaporated and the resultant residue was washed with H2O (2×10mL) and CH2Cl2 (2×40mL). The organic phase was dried over MgSO4 and concentrated to get LC as yellow oil (2.94g, 68%). Anal. Calc. for C16H30N2 (%): C, 76.74; H, 12.07; N, 11.19. Found: C, 76.65; H, 12.04; N, 11.22. 1H NMR (500MHz, CDCl3): δ 5.34 (s, 1H, Myr-H), 3.10 (s, 2H, NHCH2Myr), 2.60-2.55 (m, 3H, NCH2, Myr-H), 2.53-2.44 (m, 6H, NCH2), 2.37-2.33 (m, 1H, Myr-H), 2.22 (q, J=20.75Hz, 2H, Myr-H), 2.07-2.04 (m, 2H, Myr-H), 1.25 (s, 3H, Myr-CH3), 0.98 (t, J=7.02Hz, 6H, NCH2CH3), 0.82 (s, 3H, Myr-CH3). 13C NMR (125MHz, CDCl3): δ 146.71, 117.36, 54.85, 52.62, 47.15 (3C, NCH2CH3, NCH2CH2N), 44.38, 40.99, 38.03, 31.62, 31.21, 26.25 (1C, Myr-CH3), 21.06 (1C, Myr-CH3), 11.87 (2C, NCH2CH3). IR (oily liquid neat; cm-1): 2967 (w), 2912 (w), 2804 (w), 1447 (w), 1380 (m), 1365 (m), 1293 (m), 11265 (m), 1201 (m), 1130 (m), 1066 (m), 957 (m), 880 (m), 777 (m), 733 (m), 682 (s).
  • 68
  • [ 18486-69-6 ]
  • [ 57-13-6 ]
  • [ 123-54-6 ]
  • 5-acetyl-4-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]-hept-2-en-2-yl]-6-methyl-3,4-dihydropyrimidin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With zinc(II) chloride at 80 - 90℃; for 4h; stereoselective reaction; Compounds 1a-1c (general procedure) A mixture of 1.0 mmol of aldehyde 2a-2c, 0.150 g (1.5 mmol) of acetylacetone, 0.090 g (1.5 mmol) of urea, and 0.014 g (0.10 mmol) of ZnCl2 was heated for 4 h at 80-90°C. The mixture was cooled and treated with 3 mL of propan-2-ol, and the precipitate was filtered off and washed with water (3 mL) and propan-2-ol (3 mL). 5-Acetyl-4-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]-hept-2-en-2-yl]-6-methyl-3,4-dihydropyrimidin-2(1H)-one (1a). Yield 45%, light yellow powder, mp 240-241°C (decomp.), [α]D22 = +55.4° (c = 0.1,CHCl3). IR spectrum, ν, cm-1: 3444 (NH), 1713, 1689(C=O), 1614 (C=N), 1229 (C-N). 1H NMR spectrum (DMSO-d6), δ, ppm: 0.77 s (3H, 17-Me), 0.95 d (1H,16-H, J = 8.4 Hz), 1.24 s (3H, 18-H), 1.98-2.09 m(1H, 15-H), 2.14 s (3H, 9-H), 2.18 s (3H, 7-H), 2.10-2.30 m (3H, 12-H, 13-H, 16-H), 2.34 d.t (1H, 12-H,J = 8.3, 5.6 Hz), 4.58 d (1H, 4-H, J = 2.5 Hz), 5.26 s(1H, 11-H), 7.41 s (1H, N3H), 8.96 s (1H, N1H).13C NMR spectrum (DMSO-d6), δC, ppm: 19.12 (C7),21.61 (C17), 26.61 (C18), 30.01 (C9), 31.09 (C12), 31.68(C16), 38.05 (C14), 40.57 (C15), 42.35 (C13), 54.85 (C4),107.33 (C5), 117.41 (C11), 148.31 (C10), 148.50 (C6),152.94 (C2), 195.04 (C8). Found, %: C 69.50;H 8.48; N 10.12. C16H22N2O2. Calculated, %: C 70.04;H 8.08; N 10.21.
  • 69
  • [ 18486-69-6 ]
  • [ 57-13-6 ]
  • [ 123-54-6 ]
  • C16H22N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With zinc(II) chloride at 80 - 90℃; for 4h; Compounds 1a-1c (general procedure) General procedure: A mixture of 1.0 mmol of aldehyde 2a-2c, 0.150 g (1.5 mmol) of acetylacetone, 0.090 g (1.5 mmol) of urea, and 0.014 g (0.10 mmol) of ZnCl2 was heated for 4 h at 80-90°C. The mixture was cooled and treated with 3 mL of propan-2-ol, and the precipitate was filtered off and washed with water (3 mL) and propan-2-ol (3 mL).
  • 70
  • [ 1816-92-8 ]
  • [ 18486-69-6 ]
  • C13H17N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide In tetrahydrofuran at -78 - -10℃; for 4h; 15.i i) Synthesis of methyl 5,5-dimethyl-4,5,6, 7-tetrahydro-1H-4,6-methanoindole-2-carboxylate (1118) [00227] A solution of 2 M LDA in THF (3.45 mL, 6.9 mmol) was cooled to -78 °C and was added 1 R-(-)-myrtenal (1.0 mL, 6.6 mmol). Methyl azidoacetate (2.6 mL, 26.3 mmol) was added drop-wise over several minutes and the reaction mixture was warmed to -10 °C and stirred for 4 h. The reaction mixture was then quenched with water and diluted with Et20. The organic phase was separated and the aqueous phase was re-extracted with ΕΣΟ (x2). The organic fractions were combined, dried over MgSC>4, filtered and concentrated in vacuo. The crude mixture was then dissolved in CH2CI2 (4.6 mL), treated with 5 % Zn (0.105 g, 0.33 mmol) and was stirred at room temperature for 15 h. The resulting mixture was filtered through decalite and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc in cyclohexane, 0-10 %) to obtain the desired compound.
  • 71
  • [ 18486-69-6 ]
  • [ 2450-71-7 ]
  • (6R,8R)-4,7,7-trimethyl-5,6,7,8-tetrahydro-6,8-methyleneisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In chlorobenzene at 100℃; for 12h; Inert atmosphere; Sealed tube;
82% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In chlorobenzene at 100℃;
81% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 15h; Inert atmosphere; Molecular sieve;
81% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20 - 80℃; for 15h; 3 (6R,8R)-4,7,7-trimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline (4b) (1R)-(-)-Myrtenal (1r, 90 mg, 0.60 mmol), propargylamine (2a, 49.5 mg, 0.90 mmol) and NaHCO3 (101 mg, 1.20 mmol) in DMF (3 mL) were stirred for 3 h at room temperature followed by 12 h at 80° C. After column chromatography (EtOAc/hexanes 5:95 to 30:70), 91 mg (81%) of a brown liquid was obtained. Rf=0.2 (EtOAc/hexanes 30:70); [α]D25-34.7 (c 1.12, CHCl3); 1H NMR (400 MHz, CDCl3): δ 8.22 (s, 1H), 7.99 (s, 1H), 2.88-2.72 (m, 3H), 2.66 (dt, J=9.7, 5.8 Hz, 1H), 2.34 (dq, J=8.7, 2.8 Hz, 1H), 2.20 (s, 3H), 1.40 (s, 3H), 1.18 (d, J=9.5 Hz, 1H), 0.60 (s, 3H); 13C{1H}NMR (100 MHz, CDCl3): δ 148.5, 143.8, 142.4, 141.5, 131.0, 44.4, 39.9, 38.7, 31.6, 31.3, 25.8, 21.2, 15.2; FTIR (neat): 2921, 1588, 1472, 1424, 1289, 1221, 1132, 955, 844, 792, 735 cm-1; MS (ESI): m/z 188 (M+H)+; HRMS (ESI): m/z calcd for C13H18N (M+H)+: 188.1434. found: 188.1437.

  • 72
  • [ 18486-69-6 ]
  • [ 110514-04-0 ]
  • (-)-2-(4'-pyridyl)-4,5-pinene-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With ammonium acetate at 80℃; for 12h; Inert atmosphere; 1.1.b; 2.1.b; 3.1.b b. Synthesis of monodentate nitrogen-containing chiral organic ligand L: Weigh 3.5 g of 4-(pyridinylacetyl)pyridine iodide intermediate prepared in step a and 2 g of ammonium acetate (NH4Ac) in a three-necked flask.Add 35~45mLofFormamide(CH3CONH2).Add 1.8 grams of myrtenal with constant stirring(-)-myrtenal(Manufactured by BEHRINGER).Heat to 80 ° C and react under nitrogen for 12 hours. The above product was filtered to give a white solid which was washed with water, recrystallized from ethanol and then dried. The yield was 85% (calculated as the intermediate).
With ammonium acetate at 75℃; for 12.5h; Inert atmosphere; 1.b; 2.b; 3.b b) Synthesis of chiral monodentate N-containing organic ligand L: (-)-2-(4'-pyridyl)-4,5-Pinene-pyridine: Weigh 4.2 g of 4-(pyridineacetyl)pyridine iodide intermediate prepared in step a and 2.5 g of ammonium acetate (NH4Ac) in a three-necked flask, then 45 mL of formamide (CH3CONH2) was added, 2.8 g of (-)-myrtenal under constant stirring was added thereto, heated to 75 ° C, and reacted for 12.5 hours under nitrogen. The above product was filtered to give a milky white solid, which was washed with water, recrystallized from ethanol, and then dried to give a chiral monodentate N-containing organic ligand L: (-)-2-(4'-pyridyl)-4,5-Pinene-pyridin.
  • 73
  • [ 74966-63-5 ]
  • [ 18486-69-6 ]
  • (2R,4S,4aR,8aR)-2-{(1R,5S)-6,6-dimethylbicyclo-[3.1.1]hept-2-ene-2-yl}-10-iminotetrahysro-8a,4-(epoxymethano)chromene-3,3,4(2H,4aH)-tricarbonitryle [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In ethanol at 20℃; General procedure of preparation of compounds1a-f General procedure: 2 mmol of corresponding aldehyde was added 2 mmol (452 mg) 1-(2-oxocyclohexyl)ethane-1,1,2,2-tetracarbonytrile in 10 mL ethanol. The obtained mixture was stirred at room temperature until complete dissolution (monitored by TLC). The solution was kept at room temperature under air during 10-15 h for the most complete crystallization of the reaction product.The crystalline substance was filtered off, washed with10 mL of an ethanol-hexane mixture (3 : 1), and cooled down to 0-5°.
  • 74
  • [ 1448527-67-0 ]
  • [ 18486-69-6 ]
  • (6R,8R)-3-(3,5-bis(trifluoromethyl)phenyl)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: 1-{2-[3’,5’-bis(trifluoromethyl)phenyl]-2-oxoethyl}pyridinium iodide With ammonium acetate In formamide at 50℃; for 0.5h; Stage #2: myrtenal In formamide at 100℃; for 12h;
With ammonium acetate; formamide
  • 75
  • [ 18486-69-6 ]
  • [ 105688-33-3 ]
  • (6R,8R)-3-(4-chlorophenyl)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% Stage #1: 1-[2-(4-chloro-phenyl)-2-oxo-ethyl]-pyridinium iodide With ammonium acetate In formamide at 50℃; for 0.5h; Stage #2: myrtenal In formamide at 100℃; for 12h;
With ammonium acetate; formamide
  • 76
  • [ 18486-69-6 ]
  • [ 582-70-7 ]
  • (6R,8R)-3-(4-fluorophenyl)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 1-(4-fluoro-phenacyl)-pyridinium; iodide With ammonium acetate In formamide at 50℃; for 0.5h; Stage #2: myrtenal In formamide at 100℃; for 12h;
  • 77
  • [ 18486-69-6 ]
  • [ 7596-36-3 ]
  • (6R,8R)-3-(4-methoxyphenyl)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 1-(2-(4-methoxyphenyl)-2-oxoethyl)pyridin-1-ium iodide With ammonium acetate In formamide at 50℃; for 0.5h; Stage #2: myrtenal In formamide at 100℃; for 12h;
With ammonium acetate; formamide
  • 78
  • [ 18486-69-6 ]
  • [ 6277-72-1 ]
  • (6R,8R)-7,7-dimethyl-3-(naphthalen-2-yl)-5,6,7,8-tetrahydro-6,8-methanoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: 1-{2-(naphthalen-2-yl)-2-oxoethyl}pyridinium iodide With ammonium acetate In formamide at 50℃; for 0.5h; Stage #2: myrtenal In formamide at 100℃; for 12h;
With ammonium acetate; formamide
  • 79
  • [ 18486-69-6 ]
  • [ 53676-94-1 ]
  • [ 821774-79-2 ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: 1-(2-furan-2-yl-2-oxo-ethyl)-pyridinium iodide With ammonium acetate In formamide at 50℃; for 0.5h; Stage #2: myrtenal In formamide at 100℃; for 12h;
With ammonium acetate; formamide
  • 80
  • [ 18486-69-6 ]
  • [ 7465-65-8 ]
  • (6R,8R)-7,7-dimethyl-3-(thiophen-2-yl)-5,6,7,8-tetrahydro-6,8-methanoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: 1-[2-oxo-2-(thiophen-2-yl)ethyl]pyridinium iodide With ammonium acetate In formamide at 50℃; for 0.5h; Stage #2: myrtenal In formamide at 100℃; for 12h;
With ammonium acetate; formamide
  • 81
  • [ 18486-69-6 ]
  • C11H16NO(1+)*I(1-) [ No CAS ]
  • (6R,8R)-3-(tert-butyl)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% Stage #1: C11H16NO(1+)*I(1-) With ammonium acetate In formamide at 50℃; for 0.5h; Stage #2: myrtenal In formamide at 100℃; for 12h;
With ammonium acetate; formamide
  • 82
  • [ 1392510-59-6 ]
  • [ 18486-69-6 ]
  • C28H26O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In methanol; water at 20 - 25℃; for 1.5h; General procedure: A solution of 13 (1 mmol, 342 mg) in MeOH (24 mL) was treatedwith the appropriate aldehyde (1.1mmol) and aqueous KOH(1 mL, 50%). The solution was stirred at room temperature (20-25°C) for 1.5 h, cooled, diluted with H2O (up to ~ 50-60 mL),acidified with HCl to pH 3-4, and extracted with CH2Cl2 (3-10mL). The extracts were dried over calcined MgSO4 and the solventwas removed. The residue was chromatographed over a silicagel column eluted with CH2Cl2. NMR data of the newly synthesizedcompounds are given in Tables 2 and 3. Physicochemicaland additional spectral data are provided as Supporting Information.
  • 83
  • C18H14O7 [ No CAS ]
  • [ 18486-69-6 ]
  • C28H26O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In methanol; water at 20 - 25℃; for 1.5h; General procedure: A solution of 13 (1 mmol, 342 mg) in MeOH (24 mL) was treatedwith the appropriate aldehyde (1.1mmol) and aqueous KOH(1 mL, 50%). The solution was stirred at room temperature (20-25°C) for 1.5 h, cooled, diluted with H2O (up to ~ 50-60 mL),acidified with HCl to pH 3-4, and extracted with CH2Cl2 (3-10mL). The extracts were dried over calcined MgSO4 and the solventwas removed. The residue was chromatographed over a silicagel column eluted with CH2Cl2. NMR data of the newly synthesizedcompounds are given in Tables 2 and 3. Physicochemicaland additional spectral data are provided as Supporting Information.
  • 84
  • [ 18486-69-6 ]
  • (1R)-myrtenal-α-d1 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With d(4)-methanol; 4-(diphenylphosphino)-1,3-bis(2,6-diisopropylphenyl)-1H-1,2,3-triazoliumhexafluorophosphate; potassium <i>tert</i>-butylate at 90℃; for 12h; Glovebox; Inert atmosphere; 4.3 General Procedure for Deuteration of Substrates General procedure: In a glovebox, a reaction tube was charged with 1,2,3-triazolium salt A6H (7.2 mg, 0.01mmol), t-BuOK (6.7 mg, 0.06 mmol) and aldehyde or imine (0.2 mmol). The tube was sealedunder a N2 atmosphere, and anhydrous CD3OD (1 mL) was added. The solution was stirred at90 oC for 12h. The reaction mixture was concentrated in vacuo. When necessary, furtherpurification was performed by silica gel column chromatography: PE/AcOEt →30/1 to 200/1,unless otherwise stated.
67% With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; water-d2; potassium acetate In dichloromethane at 60℃; for 12h; 3 [00158] (1R)-Myrtenal (0.25 mmol), 5l (20 mol%) and KOAc (0.25 mmol, 1 equiv) was dissolved in a mixture of D2O (1 mL) and DCM (0.25 mL) in a reaction vessel (5 mL). Then the reaction mixture was vigorously stirred at 60 °C for 12 hours.10q was obtained as a colorless oil in 67% yield with 97% D-incorporation.1H NMR (400 MHz, CDCl3) d 9.41 (s, 0.03H), 6.72-6.67 (m, 1H), 2.84 (t, J = 5.6 Hz, 1H), 2.65-2.43 (m, 3H), 2.19-2.14 (m, 1H), 1.31 (s, 3H), 1.03 (d, J = 9.2 Hz, 1H), 0.72 (s, 3H); 13C NMR (100 MHz, CDCl3) d 190.9 (t, J = 26.3 Hz), 151.5 (t, J = 3.6 Hz), 147.7 (s), 40.7 (s), 38.0 (s), 37.6 (s), 33.0 (s), 31.1 (s), 25.7 (s), 20.9 (s); HRMS (EI): m/z caled for C10H13DO [(M)+]: 151.1107, found: 151.1109.
  • 85
  • [ 18486-69-6 ]
  • C19H16BrN3O2(2+)*2I(1-) [ No CAS ]
  • (6R,6'R,8R,8'R)-3,3'-(4-bromopyridine-2,6-diyl)bis(7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline) [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With ammonium acetate; formamide at 20 - 80℃; for 12.5h; Inert atmosphere; 2 Synthesis of compound 7 Under the protection of an inert gas, in a 50mL Shrek bottle that has been cooled by high temperature baking,Compound 6 (1.64 g, 2.52 mmol) and ammonium acetate (0.85 g, 5.38 mmol) were added in this order,Formamide (15 mL, 94.4 mmol) and (1R)-(-)-myrtenal (770 μL, 5.10 mmol).The mixture was stirred at room temperature for 30 min. After being stirred uniformly, it was stirred at 80 ° C. for 12 h.After the reaction was completed, it was cooled to room temperature, suction filtered, and the solid was washed with ice water and dried.The obtained solid was passed through a leaching column (neutral alumina, eluent: ethyl acetate).It was concentrated under reduced pressure, dried and weighed to obtain 818 mg of a brownish yellow powdery solid with a yield of 65%.
  • 86
  • [ 18486-69-6 ]
  • [(difluoromethyl)selanyl]methyl}benzene [ No CAS ]
  • Se-(difluoromethyl) (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboselenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 50℃; for 24h; Inert atmosphere;
72% With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 50℃; for 24h; Sealed tube; Inert atmosphere; 9 Operation steps: add 0.75 mmol in a 10 mL single-neck flask Myrtenal 1h, 0.5 mmol benzyl difluoromethyl selenium compound 2a and 1.0 mmol AIBN, the rubber stopper is sealed and vacuumed, the air in the bottle is replaced with an argon balloon, and the bottle is filled with argon gas. Then, under an argon atmosphere, 1,2-dichloroethane (2.5 mL) was added to the flask via a syringe, and reacted at 50°C for 24 hours. After the reaction, the solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by a fast silica gel column to obtain the corresponding difluoromethyl selenoester compound for 3 h with a yield of 72%.
  • 87
  • [ 18486-69-6 ]
  • [ 593-56-6 ]
  • 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde O-methyl oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
376 mg With sulfuric acid In ethanol at 35℃; Inert atmosphere; General procedure: The substituted cinnamaldehyde (5 mmol) and methoxyamine hydrochloride (7.5 mmol) were dissolved in ethanol (25 ml) and a drop of concentrated sulfuric acid was added. The mixture is reacted at 35 °C for 2-12 hours. After the reaction is over, the solvent was removed by evaporation under reduced pressure. Add water (40 ml) to the residue and extracted with ether (3*20 ml). The organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine and dried over anhydrous Na2SO4. Purification by column chromatography on silica gel (eluting with 20:1 petroleum ether:ethyl acetate) afforded mixed α,β-unsaturated oxime ether in Z/E configuration.
  • 88
  • potassium cyanide [ No CAS ]
  • [ 18486-69-6 ]
  • 2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-hydroxyacetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With carbon dioxide In ethanol at 20℃; for 18h; Sealed tube;
  • 89
  • tetrafluoroboric acid [ No CAS ]
  • [ 32293-33-7 ]
  • [ 18486-69-6 ]
  • 1-[((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylidene]-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazolium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% Stage #1: tetrafluoroboric acid; 3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole In dichloromethane; water at 20℃; Stage #2: myrtenal In dichloromethane; water at 20℃; Synthesis of alkylidene salts of pyrazolines 1a-d, 7a-c,8a-d (General method). General procedure: 50% Aqueous HBF4 (0.25 ml/mmol)was added dropwise to a vigorously stirred solution of3-arylpyrazoline in CH2Cl2 (10 ml). An equimolar amountof aldehyde or ketone was added in portions with stirring tothe resulting salt solution. Stirring was continued for 2-6 h.The precipitated crystals were filtered off, washed withH2O to pH 7, then with Et2O. If no salt precipitationoccurred, the organic layer was separated, washed withH2O to pH 7, and concentrated to dryness. Upon additionof a small amount of EtOH, the salt crystallized.
  • 90
  • tetrafluoroboric acid [ No CAS ]
  • [ 18486-69-6 ]
  • [ 62502-60-7 ]
  • 3-(4-chlorophenyl)-1-[((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylidene]-4,5-dihydro-1H-pyrazolium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% Stage #1: tetrafluoroboric acid; 3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazole In dichloromethane; water at 20℃; Stage #2: myrtenal In dichloromethane; water at 20℃; Synthesis of alkylidene salts of pyrazolines 1a-d, 7a-c,8a-d (General method). General procedure: 50% Aqueous HBF4 (0.25 ml/mmol)was added dropwise to a vigorously stirred solution of3-arylpyrazoline in CH2Cl2 (10 ml). An equimolar amountof aldehyde or ketone was added in portions with stirring tothe resulting salt solution. Stirring was continued for 2-6 h.The precipitated crystals were filtered off, washed withH2O to pH 7, then with Et2O. If no salt precipitationoccurred, the organic layer was separated, washed withH2O to pH 7, and concentrated to dryness. Upon additionof a small amount of EtOH, the salt crystallized.
  • 91
  • [ 1911-30-4 ]
  • tetrafluoroboric acid [ No CAS ]
  • [ 18486-69-6 ]
  • 1-[((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylidene]-3-phenyl-4,5-dihydro-1H-pyrazolium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% Stage #1: 3-methyl-4,5-dihydro-1H-pyrazole; tetrafluoroboric acid In dichloromethane; water at 20℃; Stage #2: myrtenal In dichloromethane; water at 20℃; Synthesis of alkylidene salts of pyrazolines 1a-d, 7a-c,8a-d (General method). General procedure: 50% Aqueous HBF4 (0.25 ml/mmol)was added dropwise to a vigorously stirred solution of3-arylpyrazoline in CH2Cl2 (10 ml). An equimolar amountof aldehyde or ketone was added in portions with stirring tothe resulting salt solution. Stirring was continued for 2-6 h.The precipitated crystals were filtered off, washed withH2O to pH 7, then with Et2O. If no salt precipitationoccurred, the organic layer was separated, washed withH2O to pH 7, and concentrated to dryness. Upon additionof a small amount of EtOH, the salt crystallized.
  • 92
  • [ 18486-69-6 ]
  • [ 73210-14-7 ]
  • tert-butyl [(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbonyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With benzoic acid at 30℃; for 3h; Inert atmosphere; Irradiation;
53% With benzoic acid In ethyl acetate at 30℃; for 12h; Irradiation; Green chemistry;
  • 93
  • [ 941-55-9 ]
  • [ 6746-94-7 ]
  • [ 18486-69-6 ]
  • (-)-(E)-2-cyclopropyl-3-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl)-N-tosylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; tetraethylammonium iodide; lithium tert-butoxide In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 94
  • [ 123-00-2 ]
  • [ 18486-69-6 ]
  • [ 68-11-1 ]
  • 2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-3-(3-morpholinopropyl)thiazolidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 4-(3-Aminopropyl)morpholine; myrtenal In tetrahydrofuran for 0.5h; Cooling with ice; Stage #2: mercaptoacetic acid In tetrahydrofuran for 0.25h; Cooling with ice; Stage #3: With dicyclohexyl-carbodiimide In tetrahydrofuran for 3h; General procedure for preparation of compounds11-20 General procedure: Amine 9 (27.7 mmol) placed in round-bottom flask, dissolved in 200 ml of THF, and placed in an ice bath, followed by addition of 41.4 mmol of aldehyde. After stirring for 30 min,61.9 mmol of thioglycolic (mercaptopropionic) acid is added and the mixture is kept for an additional 15 min followed by addition 24.9 mmol of dicyclohexylcarbodiimide. After stirringfor 3 h white precipitate is filtered off. The filtrate is concentrated,dissolved in methylene chloride, and washed with a saturated solution of sodium hydrogencarbonate. The organic phase is separated and dried over sodium sulfate. Then methylene chloride is distilled off, and the product is purified by column chromatography on silica gel. The eluent is methylene chloride with a methanol gradient of up to 3% by vol.
  • 95
  • [ 67-56-1 ]
  • [ 18486-69-6 ]
  • [ 59598-42-4 ]
YieldReaction ConditionsOperation in experiment
82% With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; C23H19Cl3N3(1+)*Cl(1-); benzoic acid In tetrahydrofuran at 20℃; for 28h;
  • 96
  • C13H13NO2 [ No CAS ]
  • [ 18486-69-6 ]
  • 3-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylamino)-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: C13H13NO2; myrtenal With 2-iodoxybenzoic acid; acetic acid In methanol at 20℃; for 2.5h; Stage #2: With sodium cyanoborohydride In methanol at 20℃; for 1.5h; 3.1.9. Synthesis of 7-aminocoumarines 25-27 General procedure: Amine 25 was obtained by the interaction of compound 23 and ()-nopinal andsubsequent reduction with NaBH3CN, in accordance with [42].Compound 25 (0.097 g,1.0 mmol), ()-nopinal (0.112 g 1.2 mmol) (synthesized by theoxidation of ()-nopol with IBX according to the procedure [43]) and acetic acid (100 L)were dissolved in methanol (5 mL) and stirred at room temperature for 2.5 h. NaBH3CN(0.110 g, 2.0 mmol) was added, and the reaction mixture was stirred at room temperaturefor 1.5 h. Methanol was evaporated and the reaction mixture was extracted with CH2Cl2.The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, andevaporated. The residue was crystallized from ethanol to give 0.115 g of 25 (64%).Similarly, compound 27 was synthesized from amine 24 and ()-myrtenal (yield-57%).7-N-acetylaminocoumarin 26 was synthesized from 7-aminocoumarin 23, in accordancewith [38].A mixture of 7-aminocoumarin 23 (0.200 g, 1.1 mmol) and DMAP (20 mg) was dissolvedin 1 mL CH2Cl2. Acetic anhydride (0.2 mL, 2.1 mmol) was added, and the mixturewas stirred at room temperature for 24 h. On completion of the reaction, 10 mL of ice-coldwater was added. The precipitate was filtered, washed with water, and dried. The resultingsolid was crystallized from ethanol to give 0.176 g of 26 (71%). NMR spectrum 26 coincidedwith the corresponding spectrum published in the literature [38].
  • 97
  • [ 7785-70-8 ]
  • [ 18486-69-6 ]
YieldReaction ConditionsOperation in experiment
54% With tert.-butylhydroperoxide; selenium(IV) oxide 3.1.3. Synthesis of Bromides 11a-c,g General procedure: (+)-Myrtenal was synthesized according to the procedure presented in [41] by theoxidation of (+)--pinene using a t-BuOOH/SeO2 system with a 57% yield.(+)-Myrtenol was synthesized from the corresponding aldehyde via reduction toalcohols with NaBH4, as described above. NaBH4 (10.3 mmol) was added to a cooled(0-5 C) solution of 10.3 mmol of the appropriate aldehyde in methanol (20 mL), and thereaction mixture was stirred for 3 h at room temperature. Then, 5% aqueous HCl wasadded to obtain a pH of 4-5. The solvent was distilled, and the product was extractedusing ether and dried with Na2SO4. The solvent was evaporated; the resulting alcohol(54% yield) was used in the synthesis without purification.(3-Methoxyphenyl)methanol was synthesized from 3-methoxybenzaldehyde via areaction with NaBH4, as described above (yield: 34%).Bromide 11a was synthesized from geraniol via the reaction with PBr3 [30].PBr3 (8.9 mmol) was added to cooled (0-5 C) solution of geraniol (26.7 mmol) indry ether (30 mL), and the reaction mixture was stirred for 2 h at r.t. Saturated aqueousNaHCO3 was added, and the product was extracted with ether. The extracts were washedwith brine, dried with Na2SO4, and evaporated.Additional bromides 11b,c,gwere synthesized as described above. Compounds 11a-c,g(with yields of 91%, 55%, 60% and 65%, respectively) were sufficiently pure and used forthe next step without purification.
  • 98
  • [ 18486-69-6 ]
  • [ 6712-78-3 ]
YieldReaction ConditionsOperation in experiment
54% With sodium tetrahydroborate In methanol at 0 - 20℃; for 3h; 3.1.3. Synthesis of Bromides 11a-c,g General procedure: (+)-Myrtenal was synthesized according to the procedure presented in [41] by theoxidation of (+)--pinene using a t-BuOOH/SeO2 system with a 57% yield.(+)-Myrtenol was synthesized from the corresponding aldehyde via reduction toalcohols with NaBH4, as described above. NaBH4 (10.3 mmol) was added to a cooled(0-5 C) solution of 10.3 mmol of the appropriate aldehyde in methanol (20 mL), and thereaction mixture was stirred for 3 h at room temperature. Then, 5% aqueous HCl wasadded to obtain a pH of 4-5. The solvent was distilled, and the product was extractedusing ether and dried with Na2SO4. The solvent was evaporated; the resulting alcohol(54% yield) was used in the synthesis without purification.(3-Methoxyphenyl)methanol was synthesized from 3-methoxybenzaldehyde via areaction with NaBH4, as described above (yield: 34%).Bromide 11a was synthesized from geraniol via the reaction with PBr3 [30].PBr3 (8.9 mmol) was added to cooled (0-5 C) solution of geraniol (26.7 mmol) indry ether (30 mL), and the reaction mixture was stirred for 2 h at r.t. Saturated aqueousNaHCO3 was added, and the product was extracted with ether. The extracts were washedwith brine, dried with Na2SO4, and evaporated.Additional bromides 11b,c,gwere synthesized as described above. Compounds 11a-c,g(with yields of 91%, 55%, 60% and 65%, respectively) were sufficiently pure and used forthe next step without purification.
  • 99
  • [ 18486-69-6 ]
  • C11H11IS [ No CAS ]
  • C21H24OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% Stage #1: C11H11IS With n-butyllithium; (trimethylsilyl)methylmagnesium chloride In diethyl ether; pentane at -78℃; for 0.00138889h; Stage #2: myrtenal at -78 - -20℃; for 0.5h;
  • 100
  • [ 18486-69-6 ]
  • C11H11IS [ No CAS ]
  • C21H24OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% Stage #1: C11H11IS With n-butyllithium; (trimethylsilyl)methylmagnesium chloride In diethyl ether; pentane at -78℃; for 0.00138889h; Stage #2: myrtenal at -78 - -20℃; for 0.5h;
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