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[ CAS No. 129-64-6 ] {[proInfo.proName]}

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Chemical Structure| 129-64-6
Chemical Structure| 129-64-6
Structure of 129-64-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 129-64-6 ]

CAS No. :129-64-6 MDL No. :MFCD00151106
Formula : C9H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :164.16 Pubchem ID :-
Synonyms :
Carbic Anhydride

Calculated chemistry of [ 129-64-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.56
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.05
TPSA : 43.37 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) : -6.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 0.66
Log Po/w (WLOGP) : 0.51
Log Po/w (MLOGP) : 1.61
Log Po/w (SILICOS-IT) : 0.97
Consensus Log Po/w : 1.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.27
Solubility : 8.74 mg/ml ; 0.0533 mol/l
Class : Very soluble
Log S (Ali) : -1.15
Solubility : 11.7 mg/ml ; 0.0713 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.49
Solubility : 53.2 mg/ml ; 0.324 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.71

Safety of [ 129-64-6 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P261-P272-P280-P284-P302+P352-P304+P340-P305+P351+P338+P310-P333+P313-P342+P311-P501 UN#:N/A
Hazard Statements:H317-H318-H334 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 129-64-6 ]

* 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.

  • Upstream synthesis route of [ 129-64-6 ]
  • Downstream synthetic route of [ 129-64-6 ]

[ 129-64-6 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 129-64-6 ]
  • [ 2746-19-2 ]
YieldReaction ConditionsOperation in experiment
80.1% at 200℃; for 0.133333 h; Microwave irradiation A method for preparing high-purity cis-5-norbornene-exo-2,3-dicarboxylic acid anhydride by microwave reaction is disclosed. The method comprises the following steps: using cis-5-norbornene-endo-2,3-dicarboxylic anhydride as raw material, Specific steps are as follows:(1) In a 1 L reaction flask, 200 g of cis-5-norbornene-endo-2,3-dicarboxylic anhydride and 600 mL of toluene were stirred and placed in a microwave autoclave. The temperature was raised to 200 ° C, 100-200GHz microwave for 8 minutes;(2) The reaction was completed, the reactor of step (1) was cooled to 110 ° C, stirred in an oil bath for 30 minutes to crystallize, cooled to room temperature, filtered and dried to give the product cis-5-norbornene- Dicarboxylic anhydride 160.2 g; Yield: 80.1percent; Purity: 98.2percent; Oxide impurity content: 0.06percent.
40% at 180℃; for 6 h; Nadic anhydride (ACROS, 225 g, 1.4 mol, pure endo isomer) was put into the 500 ml 2-neck round bottom flask, and refluxed while the temperature was increased to 180° C. Next, while it was agitated at 300 rpm, it was reacted for 6 hours, the reactants were cooled and recrystallized with benzene. The product that was rearranged by 80percent exo isomers were obtained by carrying out the recrystallization twice (yield: 40percent). [0082] The NMR analysis results of the pure endo isomer compound are described below. [0083] 1H-NMR (300 MHz, CDCl3): δ6.31 (2H), 3.50 (2H,) 3.59 (2H), δ1.57 to 1.80 (2H) [0084] In addition, the results of the NMR analysis that was carried out in order to confirm that the 80percent exo isomer nadic anhydride compound that was manufactured through thermal rearrangement was formed are described below. [0085] 1H-NMR (300 MHz, CDCl3): δ6.30 to 6.34 (2H), 3.44 (2H) 3.01 (2H), δ1.68 (1H), 61.42 (1H)
32.8% at 185℃; The synthetic procedure is a modification of the previously published method [16]. cis-5-norbornene-endo-2,3-dicarboxylic anhydride (250 g, 1.52 mol) was heated to 185 °C for 4-5 h. After cooling to room temperature, the endo/exo mixture was further purified by recrystallization in ethyl acetate four times to obtain pure cis-5-norbornene exo-2,3-dicarboxylic anhydride. Yield: 82 g (32.8percent), purity: >98percent exo isomer, mp: 141-143 °C, lit. 143 °C[16] . 1H NMR (CDCl3): δ = 6.34 (s, 2H), 3.45 (s, 2H), 3.02 (s, 2H), 1.67 (d, 1H), 1.44 (d, 1H). 13C NMR (CDCl3): δ = 172.3, 138.6, 49.4, 47.5, 44.7.
14% at 210℃; for 2 h; Inert atmosphere Example 2; Synthesis of Monomer 2: (1) Conversion of the endo to the exo isomer was adapted from previous literature procedures. (Canonne, et al., J Org Chem 1982, 47, 3953) 100 g (0.60 mol) of 5-Norbornene-2,3-dicarboxylic anhydride (endo) was placed in a 250 mL round bottom flask and heated at 210° C. under nitrogen for 2 hours. The flask was cooled to 120° C. after which toluene (100 mL) was added. This solution was allowed to cool to room temperature. The resulting mixture was filtered and the residue was recrystallized 4 times from toluene to give white crystals of 5-norbornene-2,3-dicarboxylic anhydride (exo), (14 g, 0.14 mol, 14percent yield, mp=143° C.). 1H NMR (300 MHz, CDCl3) δ 1.44 (d, J=1.2 Hz, 1H), 1.66 (d, J=1.2 Hz, 1H), 3.01 (s, 2H), 3.47 (s, 2H), 6.34 (d, J=10.2 Hz, 2H). 13C NMR (300 MHz, CDCl3) δ 171.61, 137.95, 48.77, 46.87, 44.11.

Reference: [1] Organic Letters, 2016, vol. 18, # 8, p. 1808 - 1811
[2] Chemistry Letters, 1991, # 7, p. 1173 - 1176
[3] Chemistry Letters, 1991, # 7, p. 1173 - 1176
[4] Patent: CN104130228, 2016, B, . Location in patent: Paragraph 0038-0040
[5] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3953 - 3959
[6] Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 175 - 184
[7] Patent: US2014/213815, 2014, A1, . Location in patent: Paragraph 0081-0085
[8] Polymer, 2011, vol. 52, # 19, p. 4377 - 4386,10
[9] Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1553 - 1556[10] Angew. Chem., 2016, vol. 128, # 4, p. 1579 - 1582,4
[11] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 17, p. 4565 - 4573
[12] Journal of the American Chemical Society, 2008, vol. 130, # 21, p. 6731 - 6733
[13] Patent: US8329927, 2012, B2, . Location in patent: Page/Page column 28-29
[14] Journal of the American Chemical Society, 1951, vol. 73, p. 4889,4891
[15] Liebigs Annalen der Chemie, 1987, p. 607 - 616
[16] Journal of Mass Spectrometry, 1996, vol. 31, # 9, p. 1028 - 1032
[17] Russian Journal of Organic Chemistry, 2009, vol. 45, # 2, p. 234 - 241
[18] Organic Process Research and Development, 2009, vol. 13, # 5, p. 1022 - 1025
[19] Organic Letters, 2010, vol. 12, # 13, p. 2904 - 2907
[20] Patent: US2011/301362, 2011, A1, . Location in patent: Page/Page column 6
[21] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 18, p. 3914 - 3921
  • 2
  • [ 129-64-6 ]
  • [ 129-64-6 ]
  • [ 2746-19-2 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide In water at 70℃; for 0.166667 h; To 5.0 g of stereoisomerized methyl-5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 48percent) and 5.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 48percent) were added 18.5 g of water and 16.5 g of a 30 wtpercent aqueous solution of sodium hydroxide (1.1 equivalents relative to 5-norbornene-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 7.4 g (exo stereoisomeric ratio for the general formula (1) type = 87percent).
83% With sodium hydroxide In water at 70℃; for 0.166667 h; (Example 1) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 26percent) were added 33.6 g of water and 16.3 g of a 30 wtpercent aqueous solution of sodium hydroxide (1.0 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 1.4 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 1.17 g (exo stereoisomeric ratio for the general formula (1) type = 88percent).; (Example 2) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 75percent) were added 11.1 g of water and 16.3 g of a 30 wtpercent aqueous solution of sodium hydroxide (1.0 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 4.0 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 10.33 g (exo stereoisomeric ratio for the general formula (1) type = 84percent).; (Example 3) With the exception of using 33.7 g of water, preparation was conducted in the same manner as the example 2. The obtained solid was 7.21 g (exo stereoisomeric ratio for the general formula (1) type = 92percent).; (Example 4) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 48percent) were added 33.6 g of water and 16.3 g of a 30 wtpercent aqueous solution of sodium hydroxide (1.0 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 1.9 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 4.48 g (exo stereoisomeric ratio for the general formula (1) type = 88percent).; (Example 5) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 75percent) were added 39.3 g of water and 8.2 g of a 30 wtpercent aqueous solution of sodium hydroxide (0.5 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 2.0 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 6.62 g (exo stereoisomeric ratio for the general formula (1) type = 86percent).; (Example 6) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 75percent) were added 27.9 g of water and 24.5 g of a 30 wtpercent aqueous solution of sodium hydroxide (1.5 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 6.0 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 9.90 g (exo stereoisomeric ratio for the general formula (1) type = 91percent).; (Example 7) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 75percent) were added 16.8 g of water and 8.2 g of a 30 wtpercent aqueous solution of sodium hydroxide (0.5 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 2.0 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 9.42 g (exo stereoisomeric ratio for the general formula (1) type = 79percent).; (Example 8) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 48percent) were added 42.4 g of water and 4.1 g of a 30 wtpercent aqueous solution of sodium hydroxide (0.25 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 0.5 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 2.81 g (exo stereoisomeric ratio for the general formula (1) type = 89percent).; (Example 9) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 75percent) were added 21.0 g of water and 2.1 g of a 30 wtpercent aqueous solution of sodium hydroxide (0.13 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 0.5 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 5.82 g (exo stereoisomeric ratio for the general formula (1) type = 96percent).; (Example 10) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (endo stereoisomeric ratio for the general formula (1) type = 78percent) were added 13.6 g of water and 16.4 g of a 30 wtpercent aqueous solution of sodium hydroxide (1.0 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 1.3 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration. The endo stereoisomeric ratio for the 5-norbornene-2,3-dicarboxylic acid contained within the resulting filtrate was 95percent. Furthermore, the filtration residue was 4.21 g (exo stereoisomeric ratio for the general formula (1) type = 46percent).; (Example 11) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (endo stereoisomeric ratio for the general formula (1) type = 25percent) were added 13.6 g of water and 16.3 g of a 30 wtpercent aqueous solution of sodium hydroxide (1.0 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 4.0 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration. The endo stereoisomeric ratio for the 5-norbornene-2,3-dicarboxylic acid contained within the resulting filtrate was 87percent. Furthermore, the filtration residue was 11.15 g (exo stereoisomeric ratio for the general formula (1) type = 89percent).; (Example 12) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (endo stereoisomeric ratio for the general formula (1) type = 78percent) were added 1.1 g of water and 16.3 g of a 30 wtpercent aqueous solution of sodium hydroxide (1.0 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride mixture, 1.3 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration. The endo stereoisomeric ratio for the 5-norbornene-2,3-dicarboxylic acid contained within the resulting filtrate was 96percent. Furthermore, the filtration residue was 12.11 g (exo stereoisomeric ratio for the general formula (1) type = 26percent).
50% With sodium hydroxide In water at 70℃; for 0.166667 h; (Example 26) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 48percent) were added 48.9 g of water and 1.6 g of a 30 wtpercent aqueous solution of sodium hydroxide (0.1 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride, 0.19 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 4.47 g (exo stereoisomeric ratio for the general formula (1) type = 50percent).; (Example 27) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 48percent) were added 3.3 g of water and 87 g of a 45 wtpercent aqueous solution of sodium hydroxide (8.1 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride, 15.6 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 15.0 g (exo stereoisomeric ratio for the general formula (1) type = 51 percent).; (Example 28) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 48percent) was added 8.6 g of a 30 wtpercent aqueous solution of sodium hydroxide (0.5 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride, 1.0 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 11.8 g (exo stereoisomeric ratio for the general formula (1) type = 52percent).; (Example 29) To 10.0 g of 5-norbornene-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (1) type = 48percent) were added 3.8 g of water and 66 g of a 30 wtpercent aqueous solution of sodium hydroxide (4.1 equivalents relative to the 5-norbornene-2,3-dicarboxylic anhydride, 7.9 equivalents relative to 5-norbornene-endo-2,3-dicarboxylic anhydride), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 14.8 g (exo stereoisomeric ratio for the general formula (1) type = 55percent).
Reference: [1] Patent: EP1669342, 2006, A1, . Location in patent: Page/Page column 21
[2] Patent: EP1669342, 2006, A1, . Location in patent: Page/Page column 16-18
[3] Patent: EP1669342, 2006, A1, . Location in patent: Page/Page column 20
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YieldReaction ConditionsOperation in experiment
68% Reflux Example 1Synthesis of monomers Exo-norbornene dicarboxylic anhydride (1)acetona />;[ /- f*0 Pure Exo O Eπdo and Exo mixture A[00047] A mixture of exo-/endo-isomers of norbornene dicarboxlic anhydride was prepared according to the literature. The pure exo isomer was obtained by recrystallization of the mixture from acetone.[00048] The mixture of endo/exo isomers, containing 80percent exo,(27.33g) and a stirrer bar were placed in a round bottom flask (250ml) fitted with a reflux condenser. Acetone (40 ml) was added and the mixture was refluxed until the solid was completely dissolved. The mixture was then left to re-crystallize. The crystals were then filtered and dried in a vacuum oven at room temperature. The final product was obtained as white crystals in a 68percent yield (lS.Olg, 1 lOmmol). The structure was confirmed by NMR and FT-IR.
Reference: [1] Patent: WO2010/101882, 2010, A1, . Location in patent: Page/Page column 15
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  • [ 108-31-6 ]
  • [ 542-92-7 ]
  • [ 129-64-6 ]
  • [ 2746-19-2 ]
Reference: [1] Chemical Communications, 1996, # 20, p. 2315 - 2316
[2] Tetrahedron, 1999, vol. 55, # 28, p. 8547 - 8554
[3] Tetrahedron, 1999, vol. 55, # 28, p. 8547 - 8554
[4] Catalysis Letters, 2018, vol. 148, # 5, p. 1366 - 1374
  • 5
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  • [ 77-73-6 ]
  • [ 129-64-6 ]
  • [ 2746-19-2 ]
Reference: [1] Green Chemistry, 2009, vol. 11, # 1, p. 91 - 95
[2] Green Chemistry, 2009, vol. 11, # 1, p. 91 - 95
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  • [ 17812-27-0 ]
  • [ 14166-28-0 ]
YieldReaction ConditionsOperation in experiment
76% With sodium hydroxide In water at 70℃; for 0.166667 h; (Example 16) To 10.0 g of norbornane-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (2) type = 50percent) were added 33.8 g of water and 16.0 g of a 30 wtpercent aqueous solution of sodium hydroxide (1.0 equivalents relative to the norbornane-2,3-dicarboxylic anhydride mixture), and the mixture was stirred at 70°C for 10 minutes. The solid was then separated by filtration and dried. The obtained solid was 4.62 g (exo stereoisomeric ratio for the general formula (2) type = 88percent).; (Example 17) With the exception of adding 48.9 g of water, preparation was conducted in the same manner as the example 16. The obtained solid was 2.42 g (exo stereoisomeric ratio for the general formula (2) type = 91 percent).; (Example 18) With the exceptions of using 41.6 g of water and 12.0 g of the 30 wtpercent aqueous solution of sodium hydroxide (0.75 equivalents relative to the norbornane-2,3-dicarboxylic anhydride mixture), preparation was conducted in the same manner as the example 16. The obtained solid was 1.84 g (exo stereoisomeric ratio for the general formula (2) type = 88percent).; (Example 19) With the exceptions of using 38.8 g of water and 16.0 g of the 30 wtpercent aqueous solution of sodium hydroxide (1.0 equivalents relative to the norbornane-2,3-dicarboxylic anhydride mixture), preparation was conducted in the same manner as the example 16. The obtained solid was 4.01 g (exo stereoisomeric ratio for the general formula (2) type = 88percent).; (Example 20) With the exceptions of using 33.2 g of water and 24.1 g of the 30 wtpercent aqueous solution of sodium hydroxide (1.5 equivalents relative to the norbornane-2,3-dicarboxylic anhydride mixture), preparation was conducted in the same manner as the example 16. The obtained solid was 6.91 g (exo stereoisomeric ratio for the general formula (2) type = 83percent). Furthermore, the filtrate exhibited an endo stereoisomeric ratio for the general formula (2) type = 83percent.; (Example 21) With the exceptions of using 27.6 g of water and 32.2 g of the 30 wtpercent aqueous solution of sodium hydroxide (2.0 equivalents relative to the norbornane-2,3-dicarboxylic anhydride mixture), preparation was conducted in the same manner as the example 16. The obtained solid was 9.24 g (exo stereoisomeric ratio for the general formula (2) type = 76percent). Furthermore, the filtrate exhibited an endo stereoisomeric ratio for the general formula (2) type = 90percent.; (Example 22) With the exceptions of using 21.6 g of water and 12.0 g of the 30 wtpercent aqueous solution of sodium hydroxide (0.75 equivalents relative to the norbornane-2,3-dicarboxylic anhydride mixture), preparation was conducted in the same manner as the example 16. The obtained solid was 5.39 g (exo stereoisomeric ratio for the general formula (2) type = 85percent). Furthermore, the filtrate exhibited an endo stereoisomeric ratio for the general formula (2) type = 76percent.; (Example 23) With the exceptions of using 18.8 g of water and 16.1 g of the 30 wtpercent aqueous solution of sodium hydroxide (1.0 equivalents relative to the norbornane-2,3-dicarboxylic anhydride mixture), preparation was conducted in the same manner as the example 16. The obtained solid was 7.61 g (exo stereoisomeric ratio for the general formula (2) type = 81 percent). Furthermore, the filtrate exhibited an endo stereoisomeric ratio for the general formula (2) type = 83percent.
Reference: [1] Patent: EP1669342, 2006, A1, . Location in patent: Page/Page column 19
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  • [ 17812-27-0 ]
  • [ 14166-28-0 ]
YieldReaction ConditionsOperation in experiment
50% With hydrogen In tetrahydrofuran 5-norbornene-endo-2,3-dicarboxylic anhydride and 5-norbornene-exo-2,3-dicarboxylic anhydride were mixed together, tetrahydrofuran was added to the resulting mixture, and a hydrogenation was conducted under a hydrogen atmosphere using 5percent palladium-carbon as a catalyst. The hydrogenation rate was 100percent. Following completion of the hydrogenation reaction, the product was filtered and dried. The resulting powdered mixture of norbornane-endo-2,3-dicarboxylic anhydride and norbornane-exo-2,3-dicarboxylic anhydride (exo stereoisomeric ratio for the general formula (2) type = 50percent) was used as the test material
Reference: [1] Patent: EP1669342, 2006, A1, . Location in patent: Page/Page column 18-19
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Reference: [1] Patent: US2011/301362, 2011, A1,
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  • [ 14805-29-9 ]
Reference: [1] Patent: WO2015/56205, 2015, A1,
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  • [ 367514-88-3 ]
Reference: [1] Patent: WO2015/56205, 2015, A1,
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