Home Cart 0 Sign in  
X

[ CAS No. 7780-06-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 7780-06-5
Chemical Structure| 7780-06-5
Chemical Structure| 7780-06-5
Structure of 7780-06-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 7780-06-5 ]

Related Doc. of [ 7780-06-5 ]

Alternatived Products of [ 7780-06-5 ]

Product Details of [ 7780-06-5 ]

CAS No. :7780-06-5 MDL No. :MFCD00048292
Formula : C12H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RGACABDFLVLVCT-CMDGGOBGSA-N
M.W : 190.24 Pubchem ID :5273464
Synonyms :

Calculated chemistry of [ 7780-06-5 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.05
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.8
Log Po/w (XLOGP3) : 3.42
Log Po/w (WLOGP) : 2.54
Log Po/w (MLOGP) : 2.77
Log Po/w (SILICOS-IT) : 2.77
Consensus Log Po/w : 2.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.113 mg/ml ; 0.000593 mol/l
Class : Soluble
Log S (Ali) : -3.65
Solubility : 0.0424 mg/ml ; 0.000223 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.19 mg/ml ; 0.000998 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.16

Safety of [ 7780-06-5 ]

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

Application In Synthesis of [ 7780-06-5 ]

* 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 [ 7780-06-5 ]

[ 7780-06-5 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 16537-09-0 ]
  • [ 7780-06-5 ]
  • 2,3-Diphenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester [ No CAS ]
  • 2,3-Diphenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In acetonitrile Ambient temperature;
  • 2
  • [ 201230-82-2 ]
  • [ 101349-79-5 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
  • [ 111160-44-2 ]
YieldReaction ConditionsOperation in experiment
1: 8 % Chromat. 2: 60 % Chromat. With bis-triphenylphosphine-palladium(II) chloride; triethylamine for 94h; Ambient temperature;
  • 3
  • trimethylsilyl cinnamate [ No CAS ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
In chloroform Heating; Yield given;
  • 4
  • [ 7780-06-5 ]
  • [ 103-79-7 ]
  • [ 93129-66-9 ]
  • [ 93129-64-7 ]
YieldReaction ConditionsOperation in experiment
1: 15% 2: 40% With sodium hydroxide In dimethyl sulfoxide for 24h; Ambient temperature;
  • 5
  • [ 103-36-6 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
87% With indium; iodine for 26h; Heating;
  • 6
  • [ 7780-06-5 ]
  • [ 7585-39-9 ]
  • C168H154O49 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.6% With sodium hypochlorite In acetone Ambient temperature;
  • 7
  • [ 7780-06-5 ]
  • [ 780-25-6 ]
  • 3,4-Diphenyl-4-[1-phenyl-meth-(E)-ylidene]-amino}-butyric acid isopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water; acetonitrile at 0℃; for 1h;
YieldReaction ConditionsOperation in experiment
9%
PhHgCl, entspr. Saeurechlorid, LiPdCl3, Isopropanol;
Zimtsaeurechlorid, iPrOH;
Zimtsaeure, i-C3H7-Br, basischer Anionenaustauscher;

  • 9
  • [ 7780-06-5 ]
  • [ 79-15-2 ]
  • [ 195624-97-6 ]
YieldReaction ConditionsOperation in experiment
81% With potassium dioxotetrahydroxoosmate(VI); (DHQ)2-PHAL
  • 10
  • [ 621-82-9 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
93% With silicium tetrachloride for 7h; Heating;
91% With dichlorosulfoxide; anhydrous sodium carbonate for 2h; Heating;
79% With nano-silica melamine trisulfonic acid for 2h; Reflux; General procedure for the esterification of benzoicacid and methanol General procedure: In a typical experiment, benzoic acid (5 mmol, 0.610 g),methanol (5 mL) and NSMTSA (0.4 g) were stirred underreflux conditions for 2 h. Upon completion of the reaction,monitored by TLC (n-hexane/EtOAc, 4:1, V/V), the reactionvessel was cooled to room temperature. Then, the reactionmixture was stirred with NaHCO3(aq) (20%) to eliminatethe unreacted acid. The product was extracted by CH2Cl2(3 × 50 mL) and washed with brine (2 × 50 mL). The solventwas dried by anhydrous CaCl2and evaporated by vacuorotary.The desired methyl benzoate was obtained in 94%yield, exclusively (Table 3, entry 1).
65.4% With sulfuric acid for 4h; Heating;
With sulfuric acid at 70℃;
With sulfuric acid Reflux;
With hydrogenchloride In lithium hydroxide monohydrate for 8h; Reflux;

  • 11
  • [ 102-92-1 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
86% With samarium In acetonitrile at 70℃; for 0.05h;
With triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;
  • 12
  • [ 7780-06-5 ]
  • [ 124605-42-1 ]
  • 13
  • [ 7780-06-5 ]
  • [ 150949-07-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: HCl / 20 h / Heating
  • 14
  • [ 7780-06-5 ]
  • [ 157240-36-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: HCl / 20 h / Heating
  • 15
  • [ 7780-06-5 ]
  • [ 158830-39-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: HCl / 20 h / Heating 5: 325 mg / Et3N / CH2Cl2 / 0 - 20 °C
  • 16
  • [ 7780-06-5 ]
  • (2S,3S)-3-Amino-2-azido-3-phenyl-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating 4: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 5: aq. HCl / dioxane / 12 h / 90 °C
Multi-step reaction with 4 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide 4: aq. HCl / dioxane / 12 h / 90 °C
Multi-step reaction with 6 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 5: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 6: aq. HCl / dioxane / 12 h / 90 °C
  • 17
  • [ 7780-06-5 ]
  • (2S,3S)-3-Amino-2-azido-3-phenyl-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating 4: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 5: aq. HCl / dioxane / 12 h / 90 °C 6: HCl / 2.5 h / Heating
Multi-step reaction with 5 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide 4: aq. HCl / dioxane / 12 h / 90 °C 5: HCl / 2.5 h / Heating
Multi-step reaction with 7 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 5: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 6: aq. HCl / dioxane / 12 h / 90 °C 7: HCl / 2.5 h / Heating
  • 18
  • [ 7780-06-5 ]
  • [ 274681-82-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 62 percent / KHCO3 / acetone; H2O / 20 h / 70 °C
Multi-step reaction with 3 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide
  • 19
  • [ 7780-06-5 ]
  • [ 274681-83-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating
Multi-step reaction with 4 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C
  • 20
  • [ 7780-06-5 ]
  • [ 274681-84-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating 4: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C
Multi-step reaction with 3 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide
Multi-step reaction with 5 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 5: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C
  • 21
  • [ 7780-06-5 ]
  • [ 274681-94-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating 4: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 5: aq. HCl / dioxane / 12 h / 90 °C 6: HCl / 2.5 h / Heating 7: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C 8: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr
Multi-step reaction with 7 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide 4: aq. HCl / dioxane / 12 h / 90 °C 5: HCl / 2.5 h / Heating 6: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C 7: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr
Multi-step reaction with 9 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 5: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 6: aq. HCl / dioxane / 12 h / 90 °C 7: HCl / 2.5 h / Heating 8: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C 9: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr
Multi-step reaction with 5 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: HCl / 20 h / Heating 3: 406 mg / Et3N / CH2Cl2 / 0 - 20 °C 4: 90 percent / PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 2 h / 0 - 20 °C 5: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr

  • 22
  • [ 7780-06-5 ]
  • [ 274681-92-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating 4: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 5: aq. HCl / dioxane / 12 h / 90 °C 6: HCl / 2.5 h / Heating 7: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 6 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide 4: aq. HCl / dioxane / 12 h / 90 °C 5: HCl / 2.5 h / Heating 6: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 8 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 5: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 6: aq. HCl / dioxane / 12 h / 90 °C 7: HCl / 2.5 h / Heating 8: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 4 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: HCl / 20 h / Heating 3: 406 mg / Et3N / CH2Cl2 / 0 - 20 °C 4: 90 percent / PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 2 h / 0 - 20 °C

  • 23
  • [ 7780-06-5 ]
  • [ 274681-81-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C
  • 24
  • [ 7780-06-5 ]
  • [ 274681-91-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating 4: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 5: aq. HCl / dioxane / 12 h / 90 °C 6: HCl / 2.5 h / Heating 7: 120 mg / Et3N / CH2Cl2 / 2 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide 4: aq. HCl / dioxane / 12 h / 90 °C 5: HCl / 2.5 h / Heating 6: 120 mg / Et3N / CH2Cl2 / 2 h / 0 - 20 °C
Multi-step reaction with 8 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 5: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 6: aq. HCl / dioxane / 12 h / 90 °C 7: HCl / 2.5 h / Heating 8: 120 mg / Et3N / CH2Cl2 / 2 h / 0 - 20 °C
  • 25
  • [ 7780-06-5 ]
  • methyl (2S,3S)-2-amino-3-(benzoylamino)-3-phenylpropionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating 4: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 5: aq. HCl / dioxane / 12 h / 90 °C 6: HCl / 2.5 h / Heating 7: 120 mg / Et3N / CH2Cl2 / 2 h / 0 - 20 °C 8: 96 percent / H2 / Pd/C / ethyl acetate / 30 h / 20 °C / 760 Torr
Multi-step reaction with 7 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide 4: aq. HCl / dioxane / 12 h / 90 °C 5: HCl / 2.5 h / Heating 6: 120 mg / Et3N / CH2Cl2 / 2 h / 0 - 20 °C 7: 96 percent / H2 / Pd/C / ethyl acetate / 30 h / 20 °C / 760 Torr
Multi-step reaction with 9 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 5: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 6: aq. HCl / dioxane / 12 h / 90 °C 7: HCl / 2.5 h / Heating 8: 120 mg / Et3N / CH2Cl2 / 2 h / 0 - 20 °C 9: 96 percent / H2 / Pd/C / ethyl acetate / 30 h / 20 °C / 760 Torr
  • 26
  • [ 7780-06-5 ]
  • methyl (2S,3S)-2,3-diamino-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating 4: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 5: aq. HCl / dioxane / 12 h / 90 °C 6: HCl / 2.5 h / Heating 7: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C 8: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 9: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C
Multi-step reaction with 8 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide 4: aq. HCl / dioxane / 12 h / 90 °C 5: HCl / 2.5 h / Heating 6: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C 7: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 8: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C
Multi-step reaction with 10 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 5: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 6: aq. HCl / dioxane / 12 h / 90 °C 7: HCl / 2.5 h / Heating 8: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C 9: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 10: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C
Multi-step reaction with 6 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: HCl / 20 h / Heating 3: 406 mg / Et3N / CH2Cl2 / 0 - 20 °C 4: 90 percent / PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 2 h / 0 - 20 °C 5: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 6: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C

  • 27
  • [ 7780-06-5 ]
  • (2R,3S)-2,3-Diamino-3-phenyl-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: HCl / 20 h / Heating 5: 325 mg / Et3N / CH2Cl2 / 0 - 20 °C 6: 91 percent / PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 7: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 8: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C
  • 28
  • [ 7780-06-5 ]
  • methyl (4S,5S)-4-methoxycarbonyl-5-phenyl-2-imidazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 76 percent / DBU / CHCl3 / 1 h / Heating 4: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 5: aq. HCl / dioxane / 12 h / 90 °C 6: HCl / 2.5 h / Heating 7: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C 8: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 9: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 10: 72 mg / Et3N / tetrahydrofuran / 2.5 h / 0 - 20 °C
Multi-step reaction with 9 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: NaN3 / dimethylformamide 4: aq. HCl / dioxane / 12 h / 90 °C 5: HCl / 2.5 h / Heating 6: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C 7: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 8: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 9: 72 mg / Et3N / tetrahydrofuran / 2.5 h / 0 - 20 °C
Multi-step reaction with 11 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 5: 90 percent / trimethylsilyl azide / methanol / 60 h / 70 - 80 °C 6: aq. HCl / dioxane / 12 h / 90 °C 7: HCl / 2.5 h / Heating 8: 129 mg / Et3N / CH2Cl2 / 0 - 20 °C 9: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 10: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 11: 72 mg / Et3N / tetrahydrofuran / 2.5 h / 0 - 20 °C
Multi-step reaction with 7 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: HCl / 20 h / Heating 3: 406 mg / Et3N / CH2Cl2 / 0 - 20 °C 4: 90 percent / PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 2 h / 0 - 20 °C 5: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 6: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 7: 72 mg / Et3N / tetrahydrofuran / 2.5 h / 0 - 20 °C

  • 29
  • [ 7780-06-5 ]
  • (4R,5S)-4-(methoxycarbonyl)-5-phenyl-2-imidazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: HCl / 20 h / Heating 5: 325 mg / Et3N / CH2Cl2 / 0 - 20 °C 6: 91 percent / PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 7: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr 8: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C 9: 65 mg / Et3N / CH2Cl2 / 2 h / 0 - 20 °C
  • 30
  • [ 7780-06-5 ]
  • [ 342411-01-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C
  • 31
  • [ 7780-06-5 ]
  • [ 342411-13-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: HCl / 20 h / Heating 5: 325 mg / Et3N / CH2Cl2 / 0 - 20 °C 6: 91 percent / PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 7: 97 percent / H2 / Pd/C / ethyl acetate / 20 °C / 760 Torr
  • 32
  • [ 7780-06-5 ]
  • [ 342411-11-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 81 percent / K2OsO2(OH)4; (DHQ)2-PHAL 2: 93 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C 3: 91 percent / NaN3 / acetone; H2O / 20 h / 70 °C 4: HCl / 20 h / Heating 5: 325 mg / Et3N / CH2Cl2 / 0 - 20 °C 6: 91 percent / PPh3; HN3; diethyl azodicarboxylate / tetrahydrofuran; CH2Cl2 / 0 - 20 °C
  • 33
  • [ 7780-06-5 ]
  • 4-amino-3,4-diphenyl-butyric acid isopropyl ester; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 64 percent / NaOH; benzyltriethylammonium chloride / acetonitrile; H2O / 1 h / 0 °C 2: 91 percent / HCl; H2O / diethyl ether / 10 h / 20 °C
  • 34
  • [ 103-26-4 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (CH3)3SiI, I2 / CHCl3 / 6 h / 25 °C 2: CHCl3 / Heating
  • 35
  • [ 2579-22-8 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
63% With dmap In toluene at 60℃; for 12h;
  • 36
  • [ 104-54-1 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
89% With manganese(IV) oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1,2,4-triazolium iodide In toluene at 23℃; Inert atmosphere;
  • 37
  • [ 7780-06-5 ]
  • [ 191171-55-8 ]
  • [ 4888-33-9 ]
YieldReaction ConditionsOperation in experiment
32% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide In 1,4-dioxane; water for 2h; Reflux; Inert atmosphere;
  • 38
  • [ 7780-06-5 ]
  • [ 1215023-97-4 ]
  • rel-(2R,3S)-isopropyl 3-phenyloxirane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodosylbenzene; C72H82MnN2O6P In benzene at 20℃; Inert atmosphere; enantioselective reaction;
  • 39
  • [ 621-84-1 ]
  • [ 7780-06-5 ]
  • C20H23NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: O-benzyl carbamate With sodium hydroxide In propan-1-ol; water at 20℃; Stage #2: isopropyl cinnamate With potassium osmate(VI) dihydrate; tert-butylhypochlorite; C47H49N5O6 In propan-1-ol; water at 20℃; for 5h; optical yield given as %ee; enantioselective reaction;
  • 40
  • [ 7780-06-5 ]
  • C12H16O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With osmium(VIII) oxide; C48H54N4O6; water; potassium carbonate; O-(methylsulfonyl)hydroxylamine; potassium hexacyanoferrate(III) In <i>tert</i>-butyl alcohol at 0℃; optical yield given as %ee; enantioselective reaction;
  • 41
  • [ 621-82-9 ]
  • [ 75-26-3 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine at 60℃; for 1h; Inert atmosphere; Ionic liquid;
  • 42
  • [ 100-42-5 ]
  • [ 201230-82-2 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
  • [ 24812-09-7 ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-3-(3-sulfopropyl)-1H-imidazol-3-ium 4-methylbenzenesulfonate; palladium diacetate; triphenylphosphine at 69.84℃; for 1.66667h; Autoclave;
  • 43
  • [ 7780-06-5 ]
  • isopropyl thionocinnamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetraphosphorus decasulfide In 1,4-dioxane Reflux; 5.4. Synthesis of the thionocinnamates 54-61 General procedure: The thionocinnamates 54refPreviewPlaceHolder1-61 were prepared by the sulfonation of their corresponding oxygenated cinnamates 13 and 47-53, refPreviewPlaceHolder[10] and refPreviewPlaceHolder[34] which in turn were prepared from the corresponding commercially available cinnamic acids and alcohols using P2S5 with little modification (refPreviewPlaceHolderScheme 5) to the literature reported procedure refPreviewPlaceHolder[35]. All the eight cinnamates (13 and 47-53) were freshly recrystallized prior to their use, and the solvent dioxane was freshly dried and distilled. A mixture of the oxygenated cinnamate 13/47-53 (100 mg) and P2S5 (1.5 equivalent) was refluxed in anhydrous dioxane (10 mL), the progress of the reaction was monitored by TLC. After completion of the reaction, the crude reaction mixture was poured into ice-cold water and extracted with ethyl acetate (3 × 30 mL). The combined organic layer was dried over sodium sulfate and evaporated in vacuo, and the residual oil was chromatographed on a silica gel column using petroleum ether. All the novel thionocinnamate 54-61 were fully and unambiguously identified on the basis of their spectral (IR, 1H NMR, 13C NMR spectra and HRMS) analysis.
  • 44
  • [ 56766-77-9 ]
  • [ 100-52-7 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
78.2% With piperidine In toluene for 30h;
  • 45
  • [ 14371-10-9 ]
  • 1-(2-(4-chlorophenyl)-2-oxoethyl)tetrahydro-1H-thiophen-1-ium bromide [ No CAS ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
  • [ 1376346-61-0 ]
  • [ 1376346-62-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(2-(4-chlorophenyl)-2-oxoethyl)tetrahydro-1H-thiophen-1-ium bromide With 1,4-diaza-bicyclo[2.2.2]octane; (5aS,10bR)-5a,10b-dihydro-2-(2',4',6'-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone In toluene at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: (E)-3-phenylpropenal; isopropyl alcohol In toluene at 20℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 46
  • [ 14371-10-9 ]
  • [ 19158-69-1 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
  • [ 1376346-63-2 ]
  • [ 1376346-66-5 ]
  • (1S,2R,3R)-isopropyl 2-(4-bromobenzoyl)-3-phenylcyclopropanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(2-(4-bromophenyl)-2-oxoethyl)tetrahydro-1H-thiophen-1-ium bromide With 1,4-diaza-bicyclo[2.2.2]octane; (5aS,10bR)-5a,10b-dihydro-2-(2',4',6'-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone In toluene at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: (E)-3-phenylpropenal; isopropyl alcohol In toluene at 20℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 47
  • [ 7780-06-5 ]
  • isopropyl (2S,3R)-3-phenyloxirane-2-carboxylate [ No CAS ]
  • [ 1006877-74-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: isopropyl cinnamate With C28H34F6MnN6O6S2; acetic acid In acetonitrile for 0.0833333h; Inert atmosphere; Stage #2: With dihydrogen peroxide In acetonitrile at -20 - 20℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
Stage #1: isopropyl cinnamate With C28H34F6MnN6O6S2; acetic acid In acetonitrile at 20℃; for 0.0333333h; Inert atmosphere; Stage #2: With dihydrogen peroxide In acetonitrile at -20℃; for 1h; Inert atmosphere; Overall yield = 79 %; Optical yield = 71 %ee; enantioselective reaction;
  • 48
  • [ 593-71-5 ]
  • [ 7780-06-5 ]
  • [ 1447768-37-7 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: Chloroiodomethane; isopropyl cinnamate With methyllithium lithium bromide In tetrahydrofuran; diethyl ether at -78℃; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; diethyl ether; water at -78℃; chemoselective reaction;
  • 49
  • [ 593-71-5 ]
  • [ 7780-06-5 ]
  • [ 1447768-37-7 ]
  • [ 88981-42-4 ]
YieldReaction ConditionsOperation in experiment
1: 11% 2: 33% Stage #1: Chloroiodomethane; isopropyl cinnamate With methyllithium lithium bromide In tetrahydrofuran; diethyl ether at -115℃; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; diethyl ether; water at -78℃; chemoselective reaction;
  • 50
  • [ 104-54-1 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
  • [ 104-55-2 ]
YieldReaction ConditionsOperation in experiment
1: 9.2% 2: 86% With oxygen; potassium hydroxide In chloroform; water at 35℃; for 5h;
  • 51
  • [ 104-55-2 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
98% With dihydrogen peroxide at 20℃; for 20h; 2.1. Oxidative reactions General procedure: FeNP (0.01mmol, 10mol%) was added to a solution of aldehyde (1mmol) in 2mL of ethanol or methanol. Then 2mmol of 33% H2O2 was slowly added under constant stirring and the reaction was further left at room temperature for 20h. The reaction progress was monitored by thin layer chromatography (TLC). After filtration of the supported iron catalyst, the solvent was removed under vacuum and the residue was purified by column chromatography using the solvent system hexane/ethyl acetate at a ratio 9:1. The purified fractions were then subjected to Nuclear Magnetic Resonance (NMR) to determine the structures of the compounds.
89% With (phthalocyaninato)iron(II); 2,6-di-tert-butylphenol; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen; 1,4-dimethyl-1,2,4-triazolium iodide In acetonitrile at 20℃; for 3h; Green chemistry;
12% With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; C14H18N3(1+)*C2F6NO4S2(1-); potassium <i>tert</i>-butylate In tetrahydrofuran at 40℃; chemoselective reaction;
  • 52
  • [ 7780-06-5 ]
  • [ 622-37-7 ]
  • isopropyl 1,5-diphenyl-1H-1,2,3-triazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With 1,8-diazabicyclo[5.4.0]undec-7-ene In chloroform at 80℃; for 48h;
54% With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; caesium carbonate In acetonitrile at 80℃; for 72h; regioselective reaction;
  • 53
  • [ 7780-06-5 ]
  • [ 65017-34-7 ]
YieldReaction ConditionsOperation in experiment
93% With dihydrogen peroxide; acetic acid In acetonitrile for 1h; enantioselective reaction;
  • 54
  • [ 109-99-9 ]
  • [ 7780-06-5 ]
  • [ 104-15-4 ]
  • isopropyl 2-bromo-3-phenyl-3-(4-(p-tosyloxy)butoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With N-Bromosuccinimide; zinc(II) chloride for 52h; Inert atmosphere; diastereoselective reaction;
  • 55
  • [ 7780-06-5 ]
  • [ 504-02-9 ]
  • (4R)-isopropyl 2-hydroxy-5-oxo-4-phenyl-3,4,5,6,7,8-hexahydro-2H-chromene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With C45H48O3; diethylzinc In tetrahydrofuran; hexane at 10℃; for 30h; Molecular sieve; Inert atmosphere; enantioselective reaction; 4.2. Representative procedure for the dinuclear zinc-Pro-Phenol complex catalyzed tandem Michael addition/acetalization reactions General procedure: Diethylzinc (1 M in hexane, 13 mL, 13 mmol, 10 mol %) was added via microsyringe to a stirred solution of chiral ligand L1 (6 mmol,5 mol %) in freshly distilled anhydrous THF (0.3 mL) under a nitrogen atmosphere, and the mixture was stirred at room temperature for 30 min to generate the zinc catalyst. The resulting solution was cooled to 10 °C, and was quickly added into a stirred solution of β,γ-unsaturated α-ketoester 1 (0.125 mmol), cyclic 1,3-diketone 2(0.125 mmol), and 10 mg 4 Å MS in freshly distilled anhydrous THF(1.0 mL) at 10 °C under a nitrogen atmosphere. The reaction mixture was stirred at 10 °C, and was monitored by TLC analysis. After total consumption of reactants, the reaction was quenched using saturated aqueous solution of NH4Cl, and was extracted with ethylacetate for three times. The combined organic layer was washed with saturated aqueous solution of Na2CO3 and brine, and driedover anhydrous Na2SO4, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gelusing a mixture of petroleum ether and ethyl acetate as eluent. Absolute configurations of the tandem reaction products were assigned by correlation to literature data and considering the similarity in the stereochemical reaction pathway.
  • 56
  • [ 7780-06-5 ]
  • [ 10365-98-7 ]
  • isopropyl (R)-3-(3-methoxyphenyl)-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-N-(tert-butyl)-7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxamide In water; toluene at 100℃; for 16h; Inert atmosphere; enantioselective reaction;
  • 57
  • [ 300-57-2 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
91% With water; oxygen; palladium diacetate In N,N-dimethyl acetamide at 100℃; for 24h; Schlenk technique; chemoselective reaction;
  • 58
  • [ 7780-06-5 ]
  • [ 766-77-8 ]
  • isopropyl 2-[dimethyl(phenyl)silyl]-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tris(pentafluorophenyl)borate In chloroform at 20℃; for 0.5h; Sealed tube; Inert atmosphere; chemoselective reaction;
  • 59
  • [ 7780-06-5 ]
  • [ 31197-66-7 ]
YieldReaction ConditionsOperation in experiment
65% With [bis(acetoxy)iodo]benzene; sulfuric acid In 2,2,2-trifluoroethanol Reflux;
  • 60
  • [ 75-89-8 ]
  • [ 7780-06-5 ]
  • isopropyl 2-phenyl-3,3-bis(2,2,2-trifluoroethoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With [bis(acetoxy)iodo]benzene; sulfuric acid In 2,2,2-trifluoroethanol for 7h; Reflux;
  • 61
  • [ 7780-06-5 ]
  • C12H14F2O2 [ No CAS ]
  • C12H14F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With pyridinium polyhydrogenfluoride; C40H35IO8; 3-chloro-benzenecarboperoxoic acid In dichloromethane at -40℃; enantioselective reaction;
  • 62
  • [ 621-82-9 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione; triphenylphosphine / dichloromethane / 1.5 h / 20 °C 2: dichloromethane / 0.25 h / 20 °C
  • 63
  • [ 10500-28-4 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 20℃; for 0.25h; General procedure for esterification of carboxylic acids promoted by TBCA/triphenylphosphine General procedure: To a stirred solution of TBCA (0.37 mmol) andtriphenylphosphine (1 mmol) in CH2Cl2 (6 cm3) was addedthe carboxylic acid (1 mmol) at room temperature. Theprogress of the reaction was monitored by GC-MS (time1 inTable 1) and, then, alcohol (1 mmol) was added. After time2(Table 1), cyanuric acid was filtered off and the liquid wasevaporated on a rotatory evaporator under reduced pressure.The producs were purified by column chromatography (silicagel 70-230 mesh) using diethyl ether/pentane as eluent.
  • 64
  • [ 109-99-9 ]
  • [ 7780-06-5 ]
  • [ 35193-63-6 ]
  • C36H34BrO7P [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.4% With N-Bromosuccinimide; at 25℃; for 36h;Inert atmosphere; The substrate is used cinnamic acid isopropyl ester (33.8muL, 0.2mmol) and (S) -1,1'- binaphthyl-2,2'-diyl hydrogen phosphate (73.1mg, 0.21mmol, 1.01Equiv.) , was added N- bromosuccinimide, 25 36h reaction, other experimental methods and conditions as in Example 1, to obtain a colorless oily liquid 87.2mg, yield 63.4percent.Two non enantiomers by high performance liquid chromatography The chalcone (41.6mg, 0.2mmol) and (R / S) -1,1'- binaphthyl-2,2'-diyl hydrogen phosphate (73.1mg, 0.21mmol, 1.01Equiv.) Was dissolved in 2mL<strong>[109-99-9]THF</strong> ; and at room temperature, under argon atmosphere, was slowly every 2hWas added N- bromosuccinimide (0.1mmol, 0.5Equiv.) For a total of 4 times was added, N- bromosuccinimide was added, reaction was continued for 24h, the solvent was removed under reduced pressure, the residue by column chromatography gel (ethyl acetate: n-hexane; (1: 10, V / V, 100mL), (1: 5, V / V100mL), (1: 3, V / V, 200mL)), to give a colorless oily liquid121.7mg, yield 86percent.The product form two diastereomers by high performance liquid.
  • 65
  • [ 7780-06-5 ]
  • [ 73183-34-3 ]
  • (R)-isopropyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-phenylpropanoate [ No CAS ]
  • [ 1198356-04-5 ]
YieldReaction ConditionsOperation in experiment
87 % ee Stage #1: bis(pinacol)diborane With copper(I) oxide; C35H31F2N2(1+)*Cl(1-); caesium carbonate In toluene at 25℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: isopropyl cinnamate In methanol; toluene at 25℃; for 0.5h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 66
  • [ 108-21-4 ]
  • [ 100-52-7 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
80.2 %Chromat. With aluminum (III) chloride; 1-butyl-3-methyl-3H-imidazol-1-ium fluoride; N,O-bis-(trimethylsilyl)-acetamide; 1-butyl-3-methylimidazolium chloride In dichloromethane for 4h; Inert atmosphere;
  • 67
  • N,N-di(pyridin-2-yl)cinnamamide [ No CAS ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
71% With copper(II) bis(trifluoromethanesulfonate) at 20℃; Glovebox; Inert atmosphere; Solvolysis; General Procedure: Catalytic solvolysis of amide 6 General procedure: A flame-dried 5 mL round-bottomed flask equipped with a magnetic stirring bar and a septum cap was charged withamide 6 (0.20 mmol) and Zn(OTf)2 (0.01 mmol, 5 mol% or 0.004 mmol, 2 mol%) (Cu(OTf)2 was used for the synthesis of7ac and 7c) in a glove box under Ar atmosphere. After adding anhydrous MeOH (2.0 mL) (2.0 mL of EtOH was used forthe synthesis of 7ab. 10 mL of i-PrOH was used for the synthesis of 7ac) at room temperature, the resulting clear solutionwas stirred for designated period of reaction time at the same temperature. The reaction mixture was concentrated underreduced pressure and the resulting residue was purified by flash column chromatography (for 7ab, 7b-d, and 7f-h;CHCl3/MeOH, 100:0 -39:1) (for 7a, 7ac, and 7e; hexane/EtOAc, 100:0 -19:1)to give esters 7.
  • 68
  • [ 102-92-1 ]
  • [ 7780-06-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere 2: copper(II) bis(trifluoromethanesulfonate) / 20 °C / Glovebox; Inert atmosphere; Solvolysis
  • 69
  • [ 7780-06-5 ]
  • C10H11ClN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide / isopropyl alcohol / 60 - 65 °C / Inert atmosphere 1.2: 84 h / 65 °C / Inert atmosphere 2.1: tetraethylammonium chloride; triethylamine; trichlorophosphate / 1,2-dichloro-ethane / 24 h / -35 - 35 °C / Inert atmosphere
  • 70
  • [ 7780-06-5 ]
  • [ 1092533-03-3 ]
  • 3-bromo-1-methyl-5-phenyl-1H-pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hydroxide / isopropyl alcohol / 60 - 65 °C / Inert atmosphere 1.2: 84 h / 65 °C / Inert atmosphere 2.1: tetraethylammonium bromide; triethylamine / dichloromethane / 20 - 35 °C / Inert atmosphere 2.2: 2 h / 0 - 30 °C / Inert atmosphere 2.3: 0.5 h / 20 - 25 °C / Inert atmosphere 3.1: potassium bromide; potassium phosphate; sodium hypochlorite / water; dichloromethane / 6 h / 0 - 5 °C / Inert atmosphere
  • 71
  • [ 7780-06-5 ]
  • 3-bromo-1-methyl-5-phenyl-4,5-dihydro-1H-pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide / isopropyl alcohol / 60 - 65 °C / Inert atmosphere 1.2: 84 h / 65 °C / Inert atmosphere 2.1: tetraethylammonium bromide; triethylamine / dichloromethane / 20 - 35 °C / Inert atmosphere 2.2: 2 h / 0 - 30 °C / Inert atmosphere 2.3: 0.5 h / 20 - 25 °C / Inert atmosphere
  • 72
  • [ 7780-06-5 ]
  • 3-chloro-1-methyl-5-phenyl-1H-pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hydroxide / isopropyl alcohol / 60 - 65 °C / Inert atmosphere 1.2: 84 h / 65 °C / Inert atmosphere 2.1: tetraethylammonium chloride; triethylamine; trichlorophosphate / 1,2-dichloro-ethane / 24 h / -35 - 35 °C / Inert atmosphere 3.1: manganese(IV) oxide / acetonitrile / 17 h / 60 °C / Inert atmosphere
  • 73
  • [ 7780-06-5 ]
  • [ 60-34-4 ]
  • [ 14776-37-5 ]
  • [ 54945-12-9 ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: methylhydrazine With potassium hydroxide In isopropyl alcohol at 60 - 65℃; Inert atmosphere; Stage #2: isopropyl cinnamate In isopropyl alcohol at 65℃; for 84h; Inert atmosphere;
  • 74
  • [ 7780-06-5 ]
  • [ 327969-13-1 ]
YieldReaction ConditionsOperation in experiment
96% With water; potassium carbonate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; potassium hexacyanoferrate(III) In <i>tert</i>-butyl alcohol for 6h; enantioselective reaction;
  • 75
  • [ 7780-06-5 ]
  • [ 1211417-77-4 ]
  • (1,3-dimethyl-1H-imidazol-3-ium-2-yl)(1-isopropoxy-1-oxo-3-phenylpropan-2-yl)dihydroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With 1,3-dicyano-2,4,5,6-tetrakis(N,N-diphenylamino)-benzene In acetonitrile at 30℃; for 8h; Irradiation; Inert atmosphere; regioselective reaction;
52 %Spectr. With iodine In chloroform at 25℃; for 20h; Inert atmosphere;
  • 76
  • [ 7780-06-5 ]
  • (R)-isopropyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-phenylpropanoate [ No CAS ]
  • [ 1198356-04-5 ]
YieldReaction ConditionsOperation in experiment
73 % ee With ((R)-5-mesityl-2-phenyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-2-ylidene) copper chloride; potassium <i>tert</i>-butylate; bis(pinacol)diborane In tetrahydrofuran; methanol at -40℃; for 3h; Molecular sieve; enantioselective reaction;
  • 77
  • [ 7780-06-5 ]
  • (9H-fluoren-9-yl)methyl chlorocarbamate [ No CAS ]
  • isopropyl (2S,3R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-hydroxy-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium osmate(VI) dihydrate; 1,4-bis(9-O-dihydroquinidine)phthalazine; sodium hydroxide In water; acetonitrile at 0℃; for 3h;
  • 78
  • [ 7780-06-5 ]
  • (9H-fluoren-9-yl)methyl chlorocarbamate [ No CAS ]
  • isopropyl (2R,3S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-hydroxy-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium osmate(VI) dihydrate; hydroquinidein 1,4-phthalazinediyl diether; sodium hydroxide In water; acetonitrile at 0℃; for 3h;
  • 79
  • [ 7780-06-5 ]
  • [ 17431-39-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water; hydrogen iodide / toluene / 8 h / 110 °C 2: trichlorophosphate / 2 h / 120 °C
  • 80
  • [ 7780-06-5 ]
  • [ 501-52-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water; hydrogen iodide / toluene / 8 h / 110 °C 2: hydrogen iodide / water; o-xylene / 8 h / 145 °C
Multi-step reaction with 3 steps 1: water; hydrogen iodide / toluene / 8 h / 110 °C 2: trichlorophosphate / 2 h / 120 °C 3: water; hydrogen iodide / toluene / 8 h / 110 °C
  • 81
  • [ 7780-06-5 ]
  • [ 22767-95-9 ]
  • [ 621-82-9 ]
  • [ 501-52-0 ]
YieldReaction ConditionsOperation in experiment
1: 18 %Spectr. 2: 26 %Spectr. 3: 11 %Spectr. With water; hydrogen iodide In toluene at 110℃; for 8h; General Procedure of the Reduction. 1,2-Diphenylpropan-1-one (3a) General procedure: In a test tube with a screw cap, 1a(0.212 g, 1.02mmol), 57 wt% aq. HI (0.561 g, 2.57mmol), andchlorobenzene (5.0 mL) was added. The mixture was heatedat 110 °C for 8 h. To the reaction mixture was added saturatedNa2S2O3 solution (30 mL), and was extracted CHCl3 (20mL 3). The combined organic layer was dried with Na2SO4.After filtration and evaporation, residue (0.262 g) was obtained.14.1 mg of the residue was combined with p-chlorobenzaldehyde(12.3 mg) as an internal standard. The mixture was thenmeasured with 1H NMR to determine the yield via the integrationof a methine peak of 3a (4.69 ppm) and formyl peak of p-chlorobenzaldehyde(9.98 ppm) (integration ratio = 61.5:100,98% yield). Furthermore, the reaction mixture including pchlorobenzaldehydewas subjected to column chromatographyon SiO2 (n-hexane:EtOAc = 10:1) and recycling preparativeHPLC (n-hexane:EtOAc = 10:1) to give 3a (0.1326 g, 0.631mmol, 62%) as a white solid.
  • 82
  • [ 7780-06-5 ]
  • [ 22767-95-9 ]
YieldReaction ConditionsOperation in experiment
90% With 2-(Aminomethyl)pyridine; bromopentacarbonylmanganese(I); potassium <i>tert</i>-butylate; hydrogen In 1,4-dioxane at 120℃; for 12h; Autoclave; chemoselective reaction; 4.3. Representative procedure for the catalytic hydrogenation reactions General procedure: A 4 ml glass vial was sequentially charged with solid [Mn(CO)5Br](0.015 0.030 mmol), the substrate (0.5 mmol), 2-picolylamine(0.015 0.030 mmol), and a magnetic stirring bar. The reaction componentswere then dissolved in THF (2 ml) or 1,4-dioxane (2 ml)whereupon the resulting yellow solution was then gently stirred(200 rpm) for a period of 5 min. Whilst stirring, the glass vial was sealed with the septum cap. Hereafter, solid t-BuOK (0.015 0.030 mmol) was added to the reaction mixture upon which the reaction vessel was again sealed with a septum cap which was then penetrated with a needle.Notably, the base addition was carried out without stirring. After that,the glass vial was placed in a drilled aluminum liner which was promptly transferred into the 300 ml autoclave. Once tightly sealed, the latter was purged five times with H2 (20 bar per cycle) before being pressurized to the desired value. The autoclave was then placed on a pre-heated stirring plate and heated up to the required reaction temperature. On completion of the hydrogenation reaction, the autoclave was allowed to reach room temperature. Afterwards, the remaining gas was slowlyreleased upon which the reaction mixture was degassed through brieflystirring on air. Finally, n-dodecane (12 mg) or n-hexadecane (20 mg)were added and an aliquot of 30 μl was taken from the solution, mixedwith acetone (1 ml) whereupon the resulting solution was analyzed byGC.
  • 83
  • [ 7780-06-5 ]
  • [ 5720-07-0 ]
  • [ 1413859-37-6 ]
  • C19H22O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86 % ee With C44H40Cl2O4Rh2; potassium hydroxide In 1,4-dioxane; water at 50℃; for 16h; Schlenk technique; Inert atmosphere; Overall yield = 97 percent; Overall yield = 57.9 mg; enantioselective reaction;
  • 84
  • [ 201230-82-2 ]
  • [ 536-74-3 ]
  • [ 67-63-0 ]
  • [ 7780-06-5 ]
  • [ 24812-09-7 ]
YieldReaction ConditionsOperation in experiment
47 %Spectr. With bis(acetonitrile)palladium(II) chloride; methanesulfonic acid; N1,N3-bis(2-(diphenylphosphanyl)-4-fluorophenyl)isophthalamide at 120℃; for 20h; Molecular sieve; Autoclave;
Same Skeleton Products
Historical Records