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Chemistry
Organic Building Blocks
Ketones
1,5-Dichloropentane-2,4-dione
Chemistry
Organic Building Blocks
Ketones

[ CAS No. 40630-12-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 40630-12-4
Chemical Structure| 40630-12-4
Structure of 40630-12-4 * Storage: {[proInfo.prStorage]}
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For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 40630-12-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 40630-12-4 ]

SDS Specification
Alternatived Products of [ 40630-12-4 ]

Product Details of [ 40630-12-4 ]

CAS No. :40630-12-4 MDL No. :MFCD07357286
Formula : C5H6Cl2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :UUZMIZMSMICNNC-UHFFFAOYSA-N
M.W : 169.01 Pubchem ID :13074746
Synonyms :

Calculated chemistry of [ 40630-12-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.6
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.14
TPSA : 34.14 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) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.45
Log Po/w (XLOGP3) : 1.04
Log Po/w (WLOGP) : 0.99
Log Po/w (MLOGP) : 0.71
Log Po/w (SILICOS-IT) : 1.95
Consensus Log Po/w : 1.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.28
Solubility : 8.89 mg/ml ; 0.0526 mol/l
Class : Very soluble
Log S (Ali) : -1.35
Solubility : 7.6 mg/ml ; 0.0449 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.22
Solubility : 1.03 mg/ml ; 0.00607 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 40630-12-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 UN#:1760
Hazard Statements:H315-H318-H335 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 40630-12-4 ]

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

  • Downstream synthetic route of [ 40630-12-4 ]

[ 40630-12-4 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 40630-12-4 ]
  • [ 84987-94-0 ]
YieldReaction ConditionsOperation in experiment
88% With hydroxylamine sulfate In acetic acid 1.) room temp., 30 min, 2.) reflux, 4 h;
Reference： [1]Mashraqui, Sabir H.; Keehn, Philip M. [Journal of Organic Chemistry, 1983, vol. 48, # 8, p. 1341 - 1344]
  • 2
  • [ 40630-12-4 ]
  • [ 136030-29-0 ]
YieldReaction ConditionsOperation in experiment
75% In methanol Inert atmosphere; Autoclave;
42% With dichloro-R-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ruthenium; hydrogen In methanol Inert atmosphere;
With hydrogen In methanol at 102℃;
With Ru2Cl4{(R)-binap}2(C2H5)3N; hydrogen In methanol at 65 - 70℃; Inert atmosphere; Schlenk technique; Glovebox; enantioselective reaction;

Reference： [1]Walleser, Patrick; Brueckner, Reinhard [European Journal of Organic Chemistry, 2014, vol. 2014, # 15, p. 3210 - 3224]
[2]Singh, Gurpreet; Meyer, Angelica; Aube, Jeffrey [Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 452 - 458]
[3]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[4]Rychnovsky, Scott D.; Griesgraber, George; Powers, Jay P. [Organic Syntheses, 2000, vol. 77, p. 1 - 1]
  • 3
  • [ 40630-12-4 ]
  • [ 136030-28-9 ]
YieldReaction ConditionsOperation in experiment
68% With [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen In methanol at 20 - 110℃; for 0.416667h; Inert atmosphere; Autoclave;
64% With hydrogen In methanol at 102℃; for 1h;
40% With dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); hydrogen In methanol Inert atmosphere;
7.66 g With Ru2Cl4{2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}2*N(C2H5)3; hydrogen In methanol at 65 - 70℃; Inert atmosphere; Schlenk technique; Glovebox; enantioselective reaction;

Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
[2]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[3]Singh, Gurpreet; Meyer, Angelica; Aube, Jeffrey [Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 452 - 458]
[4]Rychnovsky, Scott D.; Griesgraber, George; Powers, Jay P. [Organic Syntheses, 2000, vol. 77, p. 1 - 1]
  • 4
  • [ 123-54-6 ]
  • [ 40630-12-4 ]
YieldReaction ConditionsOperation in experiment
43% With aluminum (III) chloride; nitrobenzene; chloroacetyl chloride In 1,2-dichloro-ethane at 0 - 60℃; for 4.5h; Inert atmosphere;
Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / nitrobenzene; 1,2-dichloro-ethane / 3 h / 70 °C / Inert atmosphere; Cooling with ice 1.2: 3 h / Inert atmosphere 2.1: sulfuric acid / diethyl ether / 0.01 h
Reference： [1]Ekanayake, Arunika I.; Sobze, Lena; Kelich, Payam; Youk, Jihea; Bennett, Nicholas J.; Mukherjee, Raja; Bhardwaj, Atul; Wuest, Frank; Vukovic, Lela; Derda, Ratmir [Journal of the American Chemical Society, 2021, vol. 143, # 14, p. 5497 - 5507]
[2]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[3]Rychnovsky, Scott D.; Griesgraber, George; Powers, Jay P. [Organic Syntheses, 2000, vol. 77, p. 1 - 1]
  • 5
  • [ 40630-12-4 ]
  • [ 103729-39-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 84 percent / BF3*OEt2 / tetrahydrofuran; diethyl ether / 0.67 h / -78 °C
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: BF3*OEt2 / diethyl ether / 0.42 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[2]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 6
  • [ 40630-12-4 ]
  • [ 86117-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 62 percent / BF3*OEt2 / diethyl ether / 0.42 h / -78 °C 4: 86 percent / PPh3, DEAD / tetrahydrofuran / 5 h 5: 70 percent / BF3*OEt2 / tetrahydrofuran / 1.5 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 7
  • [ 40630-12-4 ]
  • [ 130481-49-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 1) BF3*OEt2, 2) DMAP / 1) THF, Et2O, 1,10-phenanthroline indicator, -78 deg C, 30 min, 2) CH2Cl2, 19 h
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 8
  • [ 40630-12-4 ]
  • [ 131563-81-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature
Multi-step reaction with 2 steps 1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: hydrogen; Ru2Cl4{2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}2*N(C2H5)3 / methanol / 65 - 70 °C / 64645.2 Torr / Inert atmosphere; Schlenk technique; Glovebox 2: potassium hydroxide / diethyl ether / 3 h / 0 - 25 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[2]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
[3]Rychnovsky, Scott D.; Griesgraber, George; Powers, Jay P. [Organic Syntheses, 2000, vol. 77, p. 1 - 1]
  • 9
  • [ 40630-12-4 ]
  • [ 109905-51-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / 2((R)-BINAP)>2-Et3N / methanol / 102 °C / 64643.5 Torr 2: KOH / diethyl ether / Ambient temperature
Multi-step reaction with 2 steps 1: methanol / Inert atmosphere; Autoclave 2: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[2]Walleser, Patrick; Brueckner, Reinhard [European Journal of Organic Chemistry, 2014, vol. 2014, # 15, p. 3210 - 3224]
  • 10
  • [ 40630-12-4 ]
  • [ 135943-86-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 4 percent / BF3*OEt2 / tetrahydrofuran; diethyl ether / 0.67 h / -78 °C / 1,10-phenanthroline indicator
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 11
  • [ 40630-12-4 ]
  • [ 129212-21-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 80 percent / tetrahydrofuran / 3 h / -78 deg C to 5 deg C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 12
  • [ 40630-12-4 ]
  • [ 135943-82-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 95 percent / Li2NiBr4 / tetrahydrofuran / 5 h / 25 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 13
  • [ 40630-12-4 ]
  • [ 135943-92-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 76 percent / BF3*OEt2 / tetrahydrofuran / 0.17 h / -78 °C 4: 84 percent / tetrahydrofuran / 1) -78 deg C to 0 deg C, 3 h, 2) 0 deg C, 1 h
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 14
  • [ 40630-12-4 ]
  • [ 135943-89-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 76 percent / BF3*OEt2 / tetrahydrofuran / 0.17 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 15
  • [ 40630-12-4 ]
  • [ 135943-85-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 18 percent / BF3*OEt2 / tetrahydrofuran / 0.42 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 16
  • [ 40630-12-4 ]
  • [ 136030-30-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: BF3*OEt2 / tetrahydrofuran / 0.17 h / -78 °C
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 85 percent / BF3*OEt2 / tetrahydrofuran / 0.42 h / -78 °C
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 84 percent / tetrahydrofuran / 3 h / -78 deg C to 0 deg C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[2]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[3]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 17
  • [ 40630-12-4 ]
  • [ 878049-30-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: BF3*OEt2 / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / 1,10-phenanthroline indicator
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 18
  • [ 40630-12-4 ]
  • [ 130275-04-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 95 percent / Li2NiBr4 / tetrahydrofuran / 5 h / 25 °C 4: 83 percent / CSA / acetone / 13 h
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 19
  • [ 40630-12-4 ]
  • [ 135943-90-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 79 percent / BF3*OEt2 / tetrahydrofuran / 0.33 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 20
  • [ 40630-12-4 ]
  • [ 135972-36-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 1) BF3*OEt2, 2) DMAP / 1) THF, Et2O, 1,10-phenanthroline indicator, -78 deg C, 30 min, 2) CH2Cl2, 19 h 4: 1) butyllithium, 2) BF3*OEt2 / 1a) Et2O, 0 deg C, 5 min, b) 0 deg C to room temperature, 1 h, 2) -78 deg C, 40 min
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 21
  • [ 40630-12-4 ]
  • [ 135943-93-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 79 percent / BF3*OEt2 / tetrahydrofuran / 0.33 h / -78 °C 4: 81 percent / tetrahydrofuran / 3 h / -78 deg C to 0 deg C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 22
  • [ 40630-12-4 ]
  • [ 135943-81-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 62 percent / BF3*OEt2 / diethyl ether / 0.42 h / -78 °C 4: 86 percent / PPh3, DEAD / tetrahydrofuran / 5 h 5: 70 percent / BF3*OEt2 / tetrahydrofuran / 1.5 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 23
  • [ 40630-12-4 ]
  • [ 135943-91-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 76 percent / BF3*OEt2 / tetrahydrofuran / 0.17 h / -78 °C 4: 80 percent / BF3*OEt2 / tetrahydrofuran / 0.33 h / -78 °C
Multi-step reaction with 4 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 79 percent / BF3*OEt2 / tetrahydrofuran / 0.33 h / -78 °C 4: 63 percent / BF3*OEt2 / tetrahydrofuran / 0.83 h / -78 °C
Multi-step reaction with 4 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 79 percent / BF3*OEt2 / tetrahydrofuran / 0.33 h / -78 °C 4: 85 percent / tetrahydrofuran / 3 h / -78 deg C to 0 deg C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[2]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[3]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 24
  • [ 40630-12-4 ]
  • [ 135943-94-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: H2 / 2((R)-BINAP)>2-Et3N / methanol / 102 °C / 64643.5 Torr 2: KOH / diethyl ether / Ambient temperature 3: 61 percent / BF3*OEt2 / diethyl ether / 0.42 h / -78 °C 4: 80 percent / BF3*OEt2 / tetrahydrofuran / 0.5 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 25
  • [ 40630-12-4 ]
  • [ 135943-88-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 76 percent / KCN/18-crown-6 complex / 3 h / Heating
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 26
  • [ 40630-12-4 ]
  • [ 135943-80-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 62 percent / BF3*OEt2 / diethyl ether / 0.42 h / -78 °C 4: 86 percent / PPh3, DEAD / tetrahydrofuran / 5 h
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 27
  • [ 40630-12-4 ]
  • [ 135943-95-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: H2 / 2((R)-BINAP)>2-Et3N / methanol / 102 °C / 64643.5 Torr 2: KOH / diethyl ether / Ambient temperature 3: 61 percent / BF3*OEt2 / diethyl ether / 0.42 h / -78 °C 4: 89 percent / KCN/18-crown-6 complex / 3 h / Heating
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 28
  • [ 40630-12-4 ]
  • [ 135943-86-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 88 percent / BF3*OEt2 / tetrahydrofuran; diethyl ether / 0.67 h / -78 °C / 1,10-phenanthroline indicator
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: BF3*OEt2 / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / 1,10-phenanthroline indicator
Multi-step reaction with 3 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[2]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
[3]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 29
  • [ 40630-12-4 ]
  • [ 135943-87-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 1) butyllithium, 2) BF3*OEt2 / 1a) Et2O, 0 deg C, 5 min, b) 0 deg C to room temperature, 1 h, 2) -78 deg C, 40 min
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 30
  • [ 40630-12-4 ]
  • [ 135943-79-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 62 percent / BF3*OEt2 / diethyl ether / 0.42 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 31
  • [ 40630-12-4 ]
  • [ 135943-79-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: H2 / 2((R)-BINAP)>2-Et3N / methanol / 102 °C / 64643.5 Torr 2: KOH / diethyl ether / Ambient temperature 3: 61 percent / BF3*OEt2 / diethyl ether / 0.42 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 32
  • [ 40630-12-4 ]
  • [ 135943-83-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / H2 / 2((S)-BINAP)>2-Et3N / methanol / 1 h / 102 °C / 64643.5 Torr 2: 89 percent / KOH / diethyl ether / 3 h / Ambient temperature 3: 94 percent / BF3*OEt2 / tetrahydrofuran / 0.42 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 33
  • [ 40630-12-4 ]
  • [ 103729-38-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: H2 / 2((R)-BINAP)>2-Et3N / methanol / 102 °C / 64643.5 Torr 2: KOH / diethyl ether / Ambient temperature 3: BF3*OEt2 / diethyl ether / 0.42 h / -78 °C
Reference： [1]Rychnovsky, Scott D.; Griesgraber, George; Zeller, Sam; Skalitzky, Donald J. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5161 - 5169]
  • 34
  • [ 40630-12-4 ]
  • [ 84987-97-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 88 percent / NH2OH*H2SO4 / acetic acid / 1.) room temp., 30 min, 2.) reflux, 4 h 2: KOH / ethanol; benzene / 4 h / Heating 3: 7 percent / benzene; various solvent(s) / 36 h / Irradiation
Reference： [1]Mashraqui, Sabir H.; Keehn, Philip M. [Journal of Organic Chemistry, 1983, vol. 48, # 8, p. 1341 - 1344]
  • 35
  • [ 40630-12-4 ]
  • [ 84987-98-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / NH2OH*H2SO4 / acetic acid / 1.) room temp., 30 min, 2.) reflux, 4 h 2: 48.7 percent / KOH / benzene; ethanol / 4 h / Heating
Reference： [1]Mashraqui, Sabir H.; Keehn, Philip M. [Journal of Organic Chemistry, 1983, vol. 48, # 8, p. 1341 - 1344]
  • 36
  • [ 40630-12-4 ]
  • [ 84987-95-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / NH2OH*H2SO4 / acetic acid / 1.) room temp., 30 min, 2.) reflux, 4 h 2: KOH / ethanol; benzene / 4 h / Heating
Reference： [1]Mashraqui, Sabir H.; Keehn, Philip M. [Journal of Organic Chemistry, 1983, vol. 48, # 8, p. 1341 - 1344]
  • 37
  • [ 40630-12-4 ]
  • [ 84987-96-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / NH2OH*H2SO4 / acetic acid / 1.) room temp., 30 min, 2.) reflux, 4 h 2: KOH / ethanol; benzene / 4 h / Heating
Reference： [1]Mashraqui, Sabir H.; Keehn, Philip M. [Journal of Organic Chemistry, 1983, vol. 48, # 8, p. 1341 - 1344]
  • 38
  • [ 40630-12-4 ]
  • C26H26N2O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / NH2OH*H2SO4 / acetic acid / 1.) room temp., 30 min, 2.) reflux, 4 h 2: KOH / ethanol; benzene / 4 h / Heating
Reference： [1]Mashraqui, Sabir H.; Keehn, Philip M. [Journal of Organic Chemistry, 1983, vol. 48, # 8, p. 1341 - 1344]
  • 39
  • [ 40630-12-4 ]
  • (2R)-2-[(2R)-6-oxo-3,6-dihydro-2H-2-pyranyl]methyl-6-[(E)-2-phenyl-1-ethenyl]-3,4-dihydro-2H-4-pyranone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / N,N-dimethyl-formamide; water 6.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / diethyl ether / 0.5 h / -78 - 20 °C / Inert atmosphere 6.2: 2.17 h / -78 °C / Inert atmosphere 7.1: 2-iodoxybenzoic acid / acetone / 4 h / 20 - 50 °C 8.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 9.1: tributylphosphine / toluene / 0.08 h / 20 °C / Inert atmosphere 9.2: 1.67 h / 0 - 60 °C / Inert atmosphere 10.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 20 - 100 °C / Inert atmosphere
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 40
  • [ 40630-12-4 ]
  • [ 1426140-07-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / N,N-dimethyl-formamide; water 6.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / diethyl ether / 0.5 h / -78 - 20 °C / Inert atmosphere 6.2: 2.17 h / -78 °C / Inert atmosphere 7.1: 2-iodoxybenzoic acid / acetone / 4 h / 20 - 50 °C 8.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 41
  • [ 40630-12-4 ]
  • (R)-1-{(R)-4-oxo-6-[(E)-styryl]-3,4-dihydro-2H-pyran-2-yl}pent-4-en-2-yl cinnamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / N,N-dimethyl-formamide; water 6.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / diethyl ether / 0.5 h / -78 - 20 °C / Inert atmosphere 6.2: 2.17 h / -78 °C / Inert atmosphere 7.1: 2-iodoxybenzoic acid / acetone / 4 h / 20 - 50 °C 8.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 9.1: tributylphosphine / toluene / 0.08 h / 20 °C / Inert atmosphere 9.2: 1.67 h / 0 - 60 °C / Inert atmosphere
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 42
  • [ 40630-12-4 ]
  • (S)-1-{(R)-4-oxo-6-[(E)-styryl]-3,4-dihydro-2H-pyran-2-yl}pent-4-en-2-yl cinnamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / N,N-dimethyl-formamide; water 6.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / diethyl ether / 0.5 h / -78 - 20 °C / Inert atmosphere 6.2: 2.17 h / -78 °C / Inert atmosphere 7.1: 2-iodoxybenzoic acid / acetone / 4 h / 20 - 50 °C 8.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 9.1: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 43
  • [ 40630-12-4 ]
  • [ 1426140-00-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / N,N-dimethyl-formamide; water 6.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / diethyl ether / 0.5 h / -78 - 20 °C / Inert atmosphere 6.2: 2.17 h / -78 °C / Inert atmosphere 7.1: 2-iodoxybenzoic acid / acetone / 4 h / 20 - 50 °C 8.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 9.1: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere 10.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 20 - 100 °C / Inert atmosphere
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 44
  • [ 40630-12-4 ]
  • [ 1426140-04-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / N,N-dimethyl-formamide; water
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 45
  • [ 40630-12-4 ]
  • [ 1182723-06-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 46
  • [ 40630-12-4 ]
  • [ 1426140-03-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / N,N-dimethyl-formamide; water
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 47
  • [ 40630-12-4 ]
  • [ 1426140-05-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / N,N-dimethyl-formamide; water 6.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / diethyl ether / 0.5 h / -78 - 20 °C / Inert atmosphere 6.2: 2.17 h / -78 °C / Inert atmosphere
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 48
  • [ 40630-12-4 ]
  • [ 1426140-06-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: [Me2NH2]-[RuCl(S-BINAP)]2(μ-Cl)3+; hydrogen / methanol / 0.42 h / 20 - 110 °C / 96009.6 Torr / Inert atmosphere; Autoclave 2.1: potassium hydroxide / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran / 2.5 h / -78 - -10 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / N,N-dimethyl-formamide; water 6.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / diethyl ether / 0.5 h / -78 - 20 °C / Inert atmosphere 6.2: 2.17 h / -78 °C / Inert atmosphere 7.1: 2-iodoxybenzoic acid / acetone / 4 h / 20 - 50 °C
Reference： [1]Walleser, Patrick; Brückner, Reinhard [Organic Letters, 2013, vol. 15, # 6, p. 1294 - 1297]
  • 49
  • [ 40630-12-4 ]
  • [ 60410-17-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); hydrogen / methanol / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / -40 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / acetonitrile / 1 h / 20 °C / Inert atmosphere 3.2: 3 h / 20 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 1 h / 50 °C / Inert atmosphere
Reference： [1]Singh, Gurpreet; Meyer, Angelica; Aube, Jeffrey [Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 452 - 458]
  • 50
  • [ 40630-12-4 ]
  • [ 58814-41-8 ]
  • C31H32N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With sodium hydrogencarbonate In ethanol; water Reflux; A.22 Ligand synthesis variant A: General procedure: Heating vigorous stirring 100 mmol of 1-amino isoquinoline derivatives at reflux, a mixture of 150 mmol carbonyl component, 130 mmol sodium bicarbonate, 80 ml of ethanol and 15 ml of water until the 1- amino isoquinoline generated reaction (about 3-8 hours of aldehydes, ketones, about 30-100 hours). The solvent is then removed in vacuo, the residue was dissolved in 500 ml of methylene chloride, and the mixture was cleaned three times with 200 ml of water. The organic phase has to be free of water and the solvent was removed under vacuum, so that the silicone residue chromatographed (eluent: ethyl acetate / heptane mixture). With spherical fractionating tube distillation or sublimation, resulting in the manipulation of the vacuum pump oil / solids release low-boiling components.
Reference： [1]Current Patent Assignee: MERCK KGAA - TWI520958, 2016, B Location in patent: Page/Page column 85; 86; 134
  • 51
  • [ 40630-12-4 ]
  • H-SWCDYRC-NH<SUB>2</SUB> [ No CAS ]
  • C44H58N12O13S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tris-(2-carboxyethyl)-phosphine hydrochloride In water; acetonitrile at 20℃; for 0.5h;
for 0.5h;
Reference： [1]Ekanayake, Arunika I.; Sobze, Lena; Kelich, Payam; Youk, Jihea; Bennett, Nicholas J.; Mukherjee, Raja; Bhardwaj, Atul; Wuest, Frank; Vukovic, Lela; Derda, Ratmir [Journal of the American Chemical Society, 2021, vol. 143, # 14, p. 5497 - 5507]
[2]Current Patent Assignee: UNIVERSITY OF ALBERTA - WO2020/107118, 2020, A1 Location in patent: Paragraph 0024; 0059

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