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[ CAS No. 137536-94-8 ] {[proInfo.proName]}

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Chemical Structure| 137536-94-8
Chemical Structure| 137536-94-8
Structure of 137536-94-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 137536-94-8 ]

CAS No. :137536-94-8 MDL No. :MFCD00192091
Formula : C47H38O4 Boiling Point : -
Linear Structure Formula :- InChI Key :WTZVNZRNIOJACO-NDOUMJCMSA-N
M.W : 666.80 Pubchem ID :10974386
Synonyms :

Safety of [ 137536-94-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 137536-94-8 ]

* 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 [ 137536-94-8 ]

[ 137536-94-8 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 644-97-3 ]
  • [ 137536-94-8 ]
  • (1R,7R)-9,9-dimethyl-2,2,6,6-tetra(1-naphthyl)-4-phenyl-3,5,8,10-tetraoxa-4-phosphabicyclo[5.3.0]decane [ No CAS ]
  • 2
  • [ 137536-94-8 ]
  • (3aR,8aR)-6-Chloro-2,2-dimethyl-4,4,8,8-tetra-naphthalen-1-yl-tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine [ No CAS ]
  • 3
  • [ 90-11-9 ]
  • [ 59779-75-8 ]
  • [ 137536-94-8 ]
YieldReaction ConditionsOperation in experiment
91.8% (2) Under nitrogen protection, add 1200 g of tetrahydrofuran, add 520 g of 1-bromonaphthalene, cool the ice bath to approximately 0 C, and add 850 mL isopropylmagnesium bromide in the form of 3mol/L reagent to control the temperature. T = 6 C, stirring 0.5h after the drop: (R, R)-O, O-isopropylidene diethyl tartrate 123g, 1h after the completion of the increase to 65-70 C temperature reaction 2-4h. The reaction was completed by TLC and 5 L of a saturated aqueous solution of ammonium chloride was slowly added dropwise over 5 hours to terminate the reaction. The mixture was separated by standing, and the aqueous phase was extracted twice with 2 L of ethyl acetate. The organic phases were combined, washed with 3 L of water twice, washed with 2 L of saturated brine, and concentrated to give 357 g of a yellow-brown oil. The target product was obtained by adding 1800 g of a mixed solvent (by volume, ethyl acetate:benzene = 20:1) to obtain the target product: (4R,5R)-2,2-dimethyl-fluorene, anthraquinone, quinoline, quinoa'-tetramine (1-naphthyl)-1,3-dioxane-4,5-dimethanol, namely: (4R,5R)-1-Nph-TADDOL. White crystals, 277 g, yield 91.8%, HPLC: 99.6%, ee value: 99.5%
  • 4
  • [ 137536-94-8 ]
  • [(1S,2R)-2-((3aR,8aR)-2,2-Dimethyl-4,4,8,8-tetra-naphthalen-1-yl-tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-yloxy)-1-methyl-2-phenyl-ethyl]-dimethyl-amine [ No CAS ]
  • 5
  • [ 546-68-9 ]
  • [ 137536-94-8 ]
  • {(CH3)2CO2(CH)2(C(C10H7)2)2O2}Ti(OCH(CH3)2)2 [ No CAS ]
  • 6
  • [ 762-99-2 ]
  • [ 75-09-2 ]
  • [ 75-05-8 ]
  • [ 137536-94-8 ]
  • bis(acetonitrile)dichloro[(4R,5R)-2,2-dimethyl-α,α,α',α'-tetra(naphthalen-1-yl)-1,3-dioxolane-4,5-dimethanolato(2-)-κO,κO']titanium-dichloromethane [ No CAS ]
  • 7
  • [ 762-99-2 ]
  • [ 75-05-8 ]
  • [ 137536-94-8 ]
  • (acetonitrile)dichloro[(4R,5R)-2,2-dimethyl-α,α,α',α'-tetra(naphthalen-1-yl)-1,3-dioxolane-4,5-dimethanolato(2-)-κO,κO']titanium [ No CAS ]
  • 8
  • [ 97-93-8 ]
  • [ 137536-94-8 ]
  • C49H41AlO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hexane; n-heptane; at 20℃; for 2h;Inert atmosphere;Product distribution / selectivity; Example 2 Preparation of Aluminum Catalyst and Synthesis of d-isopulegolIn a nitrogen atmosphere, 1.20 g (1.80 mmol) of (R,R)-2,2-dimethyl-α,α,α',α'-(1-naphthyl)-1,3-dioxolane-4,5-dimethanol (hereinafter sometimes referred to as (R,R)-1-naphthyl TADDOL or (R,R)-1-NAPHTADDOL) were placed in a 100 ml-reaction flask. After purged with nitrogen, heptane (24 ml), 1.9 ml of a triethylaluminum.hexane solution (1.9 mmol, 1.0 mol/L) were sequentially added and stirred at room temperature for two hours to obtain a solid substance. The solid substance was filtrated under a nitrogen atmosphere, washed with a heptane solution, dried and thereafter analyzed by NMR. As a result, a peak of the aluminum complex was confirmed other than that of the ligand. An NMR chart of the ligand and complex is shown in FIG. 5 and an enlarged view of a low magnetic field side thereof is shown in FIG. 6.
  • 9
  • [ 137536-94-8 ]
  • Al(3+)*C18H13O(1-)*C47H36O4(2-) [ No CAS ]
  • 10
  • [ 37031-29-1 ]
  • [ 90-11-9 ]
  • [ 137536-94-8 ]
YieldReaction ConditionsOperation in experiment
17% Into a 300-mL three-necked-flask, 1.6 g (64 mmol) of magnesium was put, and the air in the flask was replaced with nitrogen. Into this flask, 15 mL of tetrahydrofuran and several drops of dibromoethane were added, and the mixture was stirred at room temperature. To this mixture, a solution containing 11 mL (75 mmol) of 1-bromonaphthalene in 30 mL of tetrahydrofuran was dropped from a dropping funnel with stirring the mixture. Then, the mixture was further stirred at 80 C. for 1 hour under a nitrogen stream. After a predetermined period, a solution containing 2.7 mL (15 mmol) of (-)-2,3-O-isopropylidene-L-tartaric acid dimethyl ester in 10 mL of tetrahydrofuran was dropped to the mixture from a dropping funnel with stirring the mixture. Then, the mixture was further stirred at 80 C. for 1 hour under a nitrogen stream. After a predetermined period, methanol, water, and a dilute hydrochloric acid were added in this order to the mixture, and an aqueous layer was subjected to extraction with ethyl acetate. The extracted solution and the organic layer were combined, washed with water, a saturated aqueous solution of sodium hydrogen carbonate, and saturated saline, and dried with magnesium sulfate. [0246] This mixture was separated by gravity filtration, and the obtained filtrate was concentrated to give a red oily substance. The oily substance was purified by HPLC (developing solvent: chloroform). The resulting fraction was concentrated to give a light-yellow solid. The obtained solid was washed with methanol and suction filtered to give 1.2 g of the target white solid of R-DOL-αNp in a yield of 17%. The scheme of the above reaction is shown in (E4-1).This compound was identified as the target R-DOL-αNp by NMR. [0248] 1H NMR data of the obtained substance, R-DOL-αNp, are as follows. 1H NMR (TCE, 300 MHz): δ (ppm)=0.52 (s, 2H), 1.35 (s, 6H), 3.41 (s, 2H), 6.89-8.08 (m, 28H). [0249] FIGS. 12A and 12B and FIG. 13 show the 1H NMR charts. Note that FIG. 12B is an enlarged chart showing a range of from 0 ppm to 5 ppm of FIG. 12A, and FIG. 13 is an enlarged chart showing a range of from 5 ppm to 10 ppm of FIG. 12A. The measurement results show that R-DOL-αNp, which was the target substance, was obtained.
  • 11
  • [ 814-68-6 ]
  • [ 137536-94-8 ]
  • ((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(di(naphthalen-1-yl)methylene)diacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% General procedure: A solution of 1 (2.0g, 3.89mmol) in dry Et2O (45mL) under argon, was cooled to -50C and then a solution of n-BuLi in Et2O (5.2mL, 9.34mmol, 1.8M) was added slowly with a syringe. The mixture was kept at -50C for 1h and the acryloyl chloride (0.97mL, 12mmol) was added slowly. The mixture was allowed to warm to room temperature and then stirred overnight. The reaction was quenched by the addition of aqueous saturated sodium bicarbonate solution (60mL). The organic layer was separated and the aqueous layer was extracted with Et2O (3×30mL). The combined organic extracts were washed once with water (20mL) and brine (20mL), and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The white solid obtained was structurally characterized as the desired product 6 (2.34g, 3.76mmol, 97%) without the need for further purification.
  • 12
  • [ 920-46-7 ]
  • [ 137536-94-8 ]
  • ((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(di(naphthalen-1-yl)methylene)bis(2-methylacrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% General procedure: A solution of 1 (2.0g, 3.89mmol) in dry Et2O (45mL) under argon, was cooled to -50C and then a solution of n-BuLi in Et2O (5.2mL, 9.34mmol, 1.8M) was added slowly with a syringe. The mixture was kept at -50C for 1h and the acryloyl chloride (0.97mL, 12mmol) was added slowly. The mixture was allowed to warm to room temperature and then stirred overnight. The reaction was quenched by the addition of aqueous saturated sodium bicarbonate solution (60mL). The organic layer was separated and the aqueous layer was extracted with Et2O (3×30mL). The combined organic extracts were washed once with water (20mL) and brine (20mL), and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The white solid obtained was structurally characterized as the desired product 6 (2.34g, 3.76mmol, 97%) without the need for further purification.
  • 13
  • (3aR,12aR)-2,2,7,9-tetramethyl-4,4,12,12-tetra(naphthalen-1-yl)-7-((tributylstannyl)methyl)hexahydro-6H-[1,3]dioxolo[4,5-c][1,6]dioxacycloundecine-6,10(7H)-dione [ No CAS ]
  • (+)-2,4-dimethyl-2-[(tributylstannyl)methyl]pentane-1,5-diol [ No CAS ]
  • [ 137536-94-8 ]
  • 14
  • (3aR,12aR)-2,2,7,9-tetramethyl-4,4,12,12-tetra(naphthalen-1-yl)-7-((triphenylstannyl)methyl)hexahydro-6H-[1,3]dioxolo[4,5-c][1,6]dioxacycloundecine-6,10(7H)-dione [ No CAS ]
  • C26H32O2Sn [ No CAS ]
  • [ 137536-94-8 ]
  • 15
  • C65H70O6Sn [ No CAS ]
  • C18H40O2Sn [ No CAS ]
  • [ 137536-94-8 ]
  • 16
  • C71H58O6Sn [ No CAS ]
  • C24H28O2Sn [ No CAS ]
  • [ 137536-94-8 ]
  • 17
  • [ 137536-94-8 ]
  • (3aR,8aR)-2,2-dimethyl-4,4,8,8-tetra(naphthalen-1-yl)tetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 6-oxide [ No CAS ]
  • 18
  • [ 59779-75-8 ]
  • [ 703-55-9 ]
  • [ 137536-94-8 ]
YieldReaction ConditionsOperation in experiment
88% General procedure: A flame dried round bottom flask was charged with dimethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (1 equiv.) and LaCl3(LiCl)2 (2 equiv.) prepared as a 0.236 M stock solution in THF by the method of Knochel25 A separate flame dried round bottom flask was charged with 12 (0.1 equiv), Mg (6.3 equiv), aryl bromide (6.0 equiv.) and THF (2 M) and allowed to reflux until no solid Mg remained, approximately 30-60 min. The freshly prepared Grignard reagent was transferred by syringe to the first flask and allowed to stir at room temperature overnight under nitrogen. The reaction was quenched by addition of saturated NH4Cl (aq.), extracted with EtOAc (3x), washed with brine, dried over Na2SO4 and concentrated in vacuo to give a crude solid, which was purified by chromatography on silica gel.
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[ 137536-94-8 ]

Chemical Structure| 171086-52-5

A1006006[ 171086-52-5 ]

((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(di(naphthalen-1-yl)methanol)

Reason: Optical isomers