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[ CAS No. 7635-54-3 ] {[proInfo.proName]}

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Chemical Structure| 7635-54-3
Chemical Structure| 7635-54-3
Structure of 7635-54-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7635-54-3 ]

CAS No. :7635-54-3 MDL No. :MFCD00134483
Formula : C11H19ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KIUPCUCGVCGPPA-AEJSXWLSSA-N
M.W : 218.72 Pubchem ID :2733329
Synonyms :

Safety of [ 7635-54-3 ]

Signal Word:Danger Class:6.1,8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3277
Hazard Statements:H314-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7635-54-3 ]

* 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 [ 7635-54-3 ]

[ 7635-54-3 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 135-16-0 ]
  • [ 7635-54-3 ]
  • (S)-2-(4-[2-Amino-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyl)-4-oxo-3,4,5,6,7,8-hexahydro-pteridin-6-ylmethyl]-amino}-benzoylamino)-pentanedioic acid [ No CAS ]
  • 2
  • [ 620-08-6 ]
  • [ 7635-54-3 ]
  • 1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-4-methoxy-pyridinium; chloride [ No CAS ]
  • 4
  • [ 22191-05-5 ]
  • [ 7635-54-3 ]
  • (R)-2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-hexanedioic acid dimethyl ester [ No CAS ]
  • (S)-2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-hexanedioic acid dimethyl ester [ No CAS ]
  • 5
  • [ 7635-54-3 ]
  • [ 151-50-8 ]
  • [ 104461-84-9 ]
  • 6
  • [ 7635-54-3 ]
  • [ 78037-99-7 ]
  • (6E,8Z,11Z,14Z)-(S)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-icosa-6,8,11,14-tetraenoic acid methyl ester [ No CAS ]
  • 7
  • [ 7635-54-3 ]
  • [ 112266-45-2 ]
  • 1-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-4-methoxy-3-trimethylsilanyl-pyridinium; chloride [ No CAS ]
  • 8
  • [ 7635-54-3 ]
  • [ 126378-42-5 ]
  • [ 135365-65-0 ]
  • 9
  • [ 7635-54-3 ]
  • [ 100-47-0 ]
  • N-(r-1,t-2,c-5-2-Isopropyl-5-methylcyclohexyl)benzamide [ No CAS ]
  • N-<1-Methyl-1-(4-methylcyclohexyl)ethyl>benzamide [ No CAS ]
  • 11
  • [ 102555-71-5 ]
  • [ 7635-54-3 ]
  • Thiocarbonic acid O-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester S-[2'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonylsulfanyl)-[1,1']binaphthalenyl-2-yl] ester [ No CAS ]
  • Thiocarbonic acid O-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester S-[2'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonylsulfanyl)-[1,1']binaphthalenyl-2-yl] ester [ No CAS ]
  • 12
  • [ 7635-54-3 ]
  • [ 602-09-5 ]
  • Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 2'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-[1,1']binaphthalenyl-2-yl ester [ No CAS ]
  • Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 2'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-[1,1']binaphthalenyl-2-yl ester [ No CAS ]
  • 13
  • [ 7635-54-3 ]
  • [ 156286-12-3 ]
  • C71H19NO2 [ No CAS ]
  • 14
  • [ 7635-54-3 ]
  • [ 57182-15-7 ]
  • (3R,4S)-4-(2,6-Dimethyl-phenylamino)-2,2,5,5-tetramethyl-hexan-3-ol [ No CAS ]
  • 2-(2,6-Dimethyl-phenylamino)-3,3-dimethyl-butyric acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester [ No CAS ]
  • 15
  • [ 7635-54-3 ]
  • (3aR,4R,5R,5aS,8aR,8bR)-5-Benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-ol [ No CAS ]
  • [ 207131-20-2 ]
  • Carbonic acid (3aS,4R,5S,5aS,8aR,8bS)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester [ No CAS ]
  • 16
  • [ 7635-54-3 ]
  • [ 230309-18-9 ]
  • 3-methoxycarbonyl-4-phenylpiperidine-1-carboxylic acid menthyl ester [ No CAS ]
  • 17
  • [ 5724-81-2 ]
  • [ 7635-54-3 ]
  • 2,3-Dihydro-pyrrole-1-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester [ No CAS ]
  • 18
  • [ 32315-10-9 ]
  • [ 15356-60-2 ]
  • [ 7635-54-3 ]
YieldReaction ConditionsOperation in experiment
99% With pyridine; In dichloromethane; at -5 - 25℃; for 13h; General procedure: In a jacketed reactor equipped with a mechanical stirrer, a thermometer, a constant pressure dropping funnel and an exhaust gas absorber,Add 7L dichloromethane, the first reaction phase, temperature -5 C,780 g (5 mol) of L-menthol and 1187 g (4 mol) of triphosgene were added in portions and sufficiently stirred to dissolve them.-5 CDrop under the drop1215 g (12mo 1) triethylamine in methylene chloride (1.8 L) was added dropwise over 1 to 2 h,Insulation reaction 3h after the natural temperature rise to the second reaction stage, temperature control 25 C, stirring about 10h.After completion of the reaction, the reaction mixture was separated by filtration under filtration, and the mother liquor was washed successively with 3 L of water, 3 L of dilute hydrochloric acid (5%), 0.5 L of sodium carbonate (5%) and 0.5 L of saturated brine ,After drying over anhydrous sodium sulfate, the solvent was removed by steaming and distilled under reduced pressure to collect 108 to 109 C / 1 ImmHg fraction,1063 g of a colorless liquid was obtained in a yield of 97.2%.
  • 19
  • [ 7635-54-3 ]
  • [ 121-44-8 ]
  • [ 250716-74-6 ]
  • N,N-diethyl (-)-(1R)-menthyl carbamate [ No CAS ]
  • Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 8'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-2,2'-dimethyl-[1,1']binaphthalenyl-8-yl ester [ No CAS ]
  • 20
  • [ 7635-54-3 ]
  • [ 762203-98-5 ]
  • ((1S,2S)-2-Methyl-1-morpholin-4-ylmethyl-butyl)-carbamic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester [ No CAS ]
  • 21
  • [ 7635-54-3 ]
  • [ 100-46-9 ]
  • [ 683247-05-4 ]
  • 22
  • [ 7635-54-3 ]
  • [ 914288-77-0 ]
  • Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 7'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-[8,8']biquinolinyl-7-yl ester [ No CAS ]
  • 23
  • [ 119-65-3 ]
  • [ 7677-24-9 ]
  • [ 7635-54-3 ]
  • [ 946834-57-7 ]
  • 24
  • [ 958879-25-9 ]
  • [ 7635-54-3 ]
  • (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl 1,1-dimethyl-3,4-dihydrospiro[carbazole-2,2'-[1,3]dioxolane]-9(1H)-carboxylate [ No CAS ]
  • 25
  • [ 7635-54-3 ]
  • 2,2'-dimethyl-8,8'-dihydroxy-1,1'-binaphthyl [ No CAS ]
  • 26
  • [ 7635-54-3 ]
  • 2,2'-dimethyl-8,8'-dihydroxy-1,1'-binaphthyl [ No CAS ]
  • 27
  • [ 7635-54-3 ]
  • [ 104461-75-8 ]
  • 28
  • [ 7635-54-3 ]
  • [ 126378-46-9 ]
  • 29
  • [ 7635-54-3 ]
  • [ 126378-46-9 ]
  • 30
  • [ 7635-54-3 ]
  • [ 126378-48-1 ]
  • 31
  • [ 7635-54-3 ]
  • [ 126378-48-1 ]
  • 32
  • [ 7635-54-3 ]
  • 1-(4-bromo-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline; hydrochloride [ No CAS ]
  • [ 1005456-39-2 ]
  • 33
  • [ 862573-15-7 ]
  • [ 7635-54-3 ]
  • [ 1151683-16-7 ]
YieldReaction ConditionsOperation in experiment
49.1% With dmap; In dichloromethane; for 16h;Heating / reflux; [00166] Example 2[00167] (i?)-l-((2-(l-(Benzo[^l[l,3]dioxol-6-yl)cyclopropanecarboxamido)thiazol- 5-yl)(2-chlorophenyl)methyl)pyrrolidin-3-yl (liS^i?^^-l-isopropyl-S-methylcyclohexyl carbonate[00168] l-(Benzo[rf][l,3]dioxol-5-yl)-N-(5-((2-chlorophenyl)((i?)-3- hydroxypyi?olidin-l-yl)methyl)thiazol-2-yl)cyclopropanecarboxamide (3.00 g, 6.02 mmol) was suspended in 200 mL of anhydrous dichloromethane containing ??iV-dimethylpyridin-4- amine (2.20 g, 18.0 mmol). (lL,2i?,55)-2-Isopropyl-5-metriylcyclohexyl chloroformate (1.91 mL, 9.00 mmol) was slowly added to the suspension and the resulting mixture was heated to reflux for 16 hours. The resulting pale yellow solution was allowed to cool to room temperature, diluted with 20 mL of methanol, and then evaporated to dryness. The crude reaction mixture was separated on 330 g of silica gel utilizing a gradient of 0-5% methanol in dicholoromethane to yield the pure product as a pale yellow solid (2.0087 g, 2.9529 mmol, 49.1%). ESI-MS m/z calc. 679.3, found; 680.5 (M+l)+; Retention time 3.88 minutes.
  • 34
  • [ 3230-65-7 ]
  • [ 7635-54-3 ]
  • C20H28NO2(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; at 20℃; for 24h; General procedure for preparing diastereomeric products4 and 5: A Schlenk under a nitrogen atmosphere was charged with 3,4- dihydroisoquinoline (1.0 mmol). (-)-Menthyl chloroformate (1.0 mmol) and toluene (2 ml_) were subsequently added. The reaction mixture was stirred at room temperature over a period of 24 hours. Naphthol or a naphthol derivative <n="33"/>(1.0 mmol) was then added and the resulting mixture was stirred for another 24 hours. After being transferred to a round bottom flask comprising chloroform, the solvent was removed and the resulting diastereomers were separated by flash column chromatography on silica gel (hexane/dichloromethane = 2:1 , 1 :1 ).
  • 35
  • [ 7635-54-3 ]
  • [ 99553-79-4 ]
  • [ 1017848-52-0 ]
  • 36
  • [ 7635-54-3 ]
  • [ 217446-35-0 ]
  • [ 1017848-54-2 ]
  • 37
  • [ 1046789-84-7 ]
  • [ 7635-54-3 ]
  • [ 1046789-85-8 ]
  • 38
  • [ 263768-77-0 ]
  • [ 7635-54-3 ]
  • t-butyl[(1S)-menthyloxycarbonyl]methylphosphine-borane [ No CAS ]
  • 39
  • [ 162053-46-5 ]
  • [ 7635-54-3 ]
  • tert-butyl(dimenthyloxycarbonyl)phosphine borane [ No CAS ]
  • 40
  • [ 61-90-5 ]
  • [ 7635-54-3 ]
  • [ 1047650-51-0 ]
  • 41
  • [ 273-53-0 ]
  • [ 7635-54-3 ]
  • [ 1158181-10-2 ]
  • 42
  • [ 1202032-95-8 ]
  • [ 7635-54-3 ]
  • C22H33O5P [ No CAS ]
  • [ 1202032-97-0 ]
  • 43
  • [ 1022153-60-1 ]
  • [ 7635-54-3 ]
  • (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl 2-{3,3-difluoro-2-hydroxy-2-[5-(1H-pyrazol-1-yl)pyridin-2-yl]propyl}-4-[1-(trifluoromethyl)cyclo-propyl]methyl}-1H-imidazole-1-carboxylate [ No CAS ]
  • (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl 2-{3,3-difluoro-2-hydroxy-2-[5-(1H-pyrazol-1-yl)pyridin-2-yl]propyl}-4-[1-(trifluoromethyl)cyclo-propyl]methyl}-1H-imidazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 20℃; for 1h; Step A: (+)-Menthyl chloroformate (20 muL, 0.09 mmol) was added to a solution of racemic 1,1-difluoro-2-[5-(1H-pyrazol-1-yl)pyridin-2-yl]-3-(4-[1-(trifluoromethyl)cyclopropyl]methyl}-1H-imidazol-2-yl)propan-2-ol in pyridine (1 mL). After stirring at ambient temperature for 1 h, the reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic phase was concentrated in vacuo. Purification by HPLC (Gilson; Chiralcel AS column; 2.5% ethanol/hexane) to afford two diastereomers of (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl2-{3,3-difluoro-2-hydroxy-2-[5-(1H-pyrazol-1-yl)pyridin-2-yl]propyl}-4-[1-(trifluoromethyl)cyclo-propyl]methyl}-1H-imidazole-1-carboxylate as a white solid.
  • 44
  • [ 2706-56-1 ]
  • [ 7635-54-3 ]
  • [ 1248568-98-0 ]
  • 45
  • [ 245554-93-2 ]
  • [ 7635-54-3 ]
  • [ 1261061-27-1 ]
  • 46
  • [ 952060-29-6 ]
  • [ 7635-54-3 ]
  • [ 1261061-28-2 ]
  • 47
  • [ 7635-54-3 ]
  • [ 466-99-9 ]
  • [ 1261158-62-6 ]
YieldReaction ConditionsOperation in experiment
With acid acceptor; Compounds comprising Formula (II) (i.e., having a carbonate linkage) were prepared by reacting hydromorphone with a chloroformate having the formula RCOCl, wherein R is an alkoxy group, in the presence of an acid acceptor to afford the compound; Example 11Synthesis of 3{(1'S)-(+)-menthyloxycarboxyl}-4,5alpha-epoxy-17-methylmorphinan-6-onePhysical form: white solidSample: Gross Wt. 17.998 g; Tare 15.337 g; Net Wt. 2.661 g Exact Mass: 467.27Molecular Weight: 467.6Mass Spec Analysis (m/z): 467.27 (100.0%), 468.27 (30.9%), 469.27 (5.6%)Elemental Analysis: C, 71.92; H, 7.98; N, 3.00; O, 17.11
  • 48
  • [ 1202032-95-8 ]
  • [ 7635-54-3 ]
  • [ 1202032-97-0 ]
YieldReaction ConditionsOperation in experiment
42% With triethylamine; In dichloromethane; at 0 - 25℃; for 2.58333h; To a mixture of racemic 3 (3.1 g, 13.7 mmol) and triethylamine (2.77 g, 27.4 mmol, 2 equiv) in methylene chloride (40 mL) was added (+)-menthylchloroformate (3.6 g, 16.4 mmol, 1.2 equiv) at 0C over 5 min. The mixture was allowed to warm to 25C over 0.5 h and stirred at 25C for 2 h, then quenched by addition of water (100 mL). The methylene chloride layer was washed with brine, dried over Na2S04, and purified by column chromatography (eluent: hexane/EtOAc to EtOAc, monitored at -290 nm) to give a mixture of (+)-menthyl carbonate diastereomers (5.6 g, 13.7 mmol, 100%). The mixture was further treated with benzene (15 mL) and heated to reflux to form a clean solution. Crystallization by cooling down to 25C and filtration provided optically pure diastereomer in 42% yield (>99% de). 1HNMR (400 MHz, CDC13): S= 7.46 (t, / = 8.2 Hz, 1H), 7.01 (m, 1H), 6.79 (m, 1H), 4.57 (m, 2H), 4.42 (dd, / = 13.9, 10.7 Hz, 1H), 2.20 (m, 1H), 1.98 (m, 1H), 1.69 (m, 2H), 1.49 (m, 2H), 1.23 (dd, / = 16.4, 1.9 Hz, 9H), 1.95-1.21 (m, 2H), 0.90 (td, / = 8.9, 1.9 Hz, 6H), 0.86 (m, 1H), 0.78 (d, / = 6.9 Hz, 3H); 13PNMR (162 MHz, CDC13): delta= 62.78; 13CNMR (100 MHz, CDC13): 5 = 166.0 (d, 7 = 16 Hz), 152.2 (d, / = 23 Hz), 135.9, 114.5 (d, J = 5 Hz), 111.0 (d, / = 5 Hz), 106.8 (d, / = 88 Hz), 80.1, 66.1 (d, / = 60 Hz), 46.8, 40.3, 34.0, 33.7 (d, / = 73 Hz), 31.4, 25.9, 24.2, 23.1, 21.9, 20.7, 16.0; ESI-MS: m/z 409 [M +H]+. Note: Chiral HPLC conditions for separation of diastereomers: Chiralcel OD-H, n- heptane/isopropanol 95/5, 25C.
  • 49
  • C18H22O6 [ No CAS ]
  • [ 7635-54-3 ]
  • C40H58O10 [ No CAS ]
  • 50
  • [ 7635-54-3 ]
  • [ 475273-53-1 ]
  • Carbonic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 3'-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-9H,9'H-[4,4']bicarbazolyl-3-yl ester [ No CAS ]
  • 51
  • [ 7635-54-3 ]
  • [ 1380401-11-5 ]
  • 52
  • [ 7635-54-3 ]
  • C18H31NO5 [ No CAS ]
  • 53
  • [ 7635-54-3 ]
  • [ 56-40-6 ]
  • [ 1380401-10-4 ]
  • 54
  • tert-butyl 2-bromo-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-11-carboxylate [ No CAS ]
  • [ 7635-54-3 ]
  • [ 1416007-23-2 ]
YieldReaction ConditionsOperation in experiment
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; water; at 20℃; for 4h;Inert atmosphere; General procedure: To a suspension of powdered NaOH (45.4 g, 1.13 mol) and water (40 mL) in CH2Cl2 (1.5 L) at room temperature was added compound 2 (95.0 g, 251.9 mmol), followed by (-)-(1R,2S,5R)-menthyl chloroformate (77.2 g, 352.8 mmol) and n-Bu4NHSO4 (3.4 g, 10.0 mmol). The mixture was stirred vigorously for 4 h, quenched with aqueous saturated NH4Cl solution (750 mL) and extracted with CH2Cl2 (2 x 400 mL). The combined extracts were dried (Na2SO4), filtered and the solvent evaporated to give an oil, which was purified by column chromatography (SiO2, hexane/ethyl acetate, 95:5) to afford a mixture of diastereomers 7, which was dissolved directly in hexane (2.5 L) at room temperature. The solution was then stored at -5 C for 72 h. The resulting precipitate was filtered, washed with chilled hexane (200 mL) and dried to give 69.0 g of a pinkish solid. The solid was crushed to a fine powder, suspended in hexane (1.4 L) and heated at 60 C for 40 min with vigorous stirring. The resulting slurry was cooled to room temperature and stored at -5 C for 72 h. The solid was filtered, washed with chilled hexane (250 mL) and dried to give pure diastereomer 7a (61.0 g, 87%) as a light-pink solid.
  • 55
  • [ 1429043-82-2 ]
  • [ 7635-54-3 ]
  • (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl-1-benzyl-3'-chloro-2-oxo-2,3a,4,5-tetrahydro-1H,1'H-spiro[cyclopenta[b]pyrrole-3,4'-pyridine]-1'-carboxylate [ No CAS ]
  • 56
  • [ 1429043-74-2 ]
  • [ 7635-54-3 ]
  • (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-benzyl-4-methyl-1-oxo-2,8-diazaspiro[4.5]deca-3,6,9-triene-8-carboxylate [ No CAS ]
  • 57
  • [ 1429043-75-3 ]
  • [ 7635-54-3 ]
  • (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-benzyl-4-isopropyl-1-oxo-2,8-diazaspiro[4.5]deca-3,6,9-triene-8-carboxylate [ No CAS ]
  • 58
  • [ 1429043-77-5 ]
  • [ 7635-54-3 ]
  • C27H34N2O3 [ No CAS ]
  • (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 2-benzyl-3-methylidene-1-oxo-2,8-diazaspiro[4.5]deca-6,9-diene-8-carboxylate [ No CAS ]
  • 59
  • [ 1429043-78-6 ]
  • [ 7635-54-3 ]
  • C29H36N2O3 [ No CAS ]
  • (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-benzyl-2-oxo-3,5,6,6a-tetrahydro-1’H,2H-spiro[cyclopenta[b]pyrrole-1,4’-pyridine]-1’-carboxylate [ No CAS ]
  • 60
  • [ 7635-54-3 ]
  • [ 672-66-2 ]
  • [ 1462469-96-0 ]
YieldReaction ConditionsOperation in experiment
71% In toluene; at 20℃; for 0.5h; General procedure: Phosphine was added to a solution of the chloroformate in toluene. This mixture was stirred at room temperature for 30 min. The resulting precipitate was collected by filtration and washed with toluene and dried to yield the alkoxycarbonyl phosphonium salt
  • 61
  • [ 5950-36-7 ]
  • [ 7635-54-3 ]
  • 1-(-)-menthyloxycarbonyl-aziridine-2-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With N-ethyl-N,N-diisopropylamine; In acetone; at 0 - 20℃; General procedure: 1.0 equiv of aziridine-2-carboxylic acid ester was mixed withacetone (2 mL of acetone for 1 mmol of ester) and 2.5 equiv ofdiisopropylethylamine. The reaction mixturewas cooled to 0 C and1.0 equiv of alkyl chloroformate was added. The reaction mixturewas stirred at room temperature 3e5 h. Precipitate was filtered offand solvent was evaporated in vacuo, resulting oil was purified bycolumn chromatography on silica gel (200 mL for 1 g of mixture)with PEeEtOAc 4:1 as an eluent.
  • 62
  • [ 7635-54-3 ]
  • [ 5950-34-5 ]
  • 1-(-)-menthyloxycarbonyl-aziridine-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With N-ethyl-N,N-diisopropylamine; In acetone; at 0 - 20℃; General procedure: 1.0 equiv of aziridine-2-carboxylic acid ester was mixed withacetone (2 mL of acetone for 1 mmol of ester) and 2.5 equiv ofdiisopropylethylamine. The reaction mixturewas cooled to 0 C and1.0 equiv of alkyl chloroformate was added. The reaction mixturewas stirred at room temperature 3e5 h. Precipitate was filtered offand solvent was evaporated in vacuo, resulting oil was purified bycolumn chromatography on silica gel (200 mL for 1 g of mixture)with PEeEtOAc 4:1 as an eluent.
  • 63
  • [ 7635-54-3 ]
  • [ 5950-39-0 ]
  • 2-isopropyl 2-(-)-menthyl aziridine-2,2-dicarboxylate [ No CAS ]
  • 64
  • [ 7635-54-3 ]
  • [ 5950-39-0 ]
  • 1-(-)-menthyloxycarbonyl-aziridine-2-carboxylic acid isopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With N-ethyl-N,N-diisopropylamine; In acetone; at 0 - 20℃; General procedure: 1.0 equiv of aziridine-2-carboxylic acid ester was mixed withacetone (2 mL of acetone for 1 mmol of ester) and 2.5 equiv ofdiisopropylethylamine. The reaction mixturewas cooled to 0 C and1.0 equiv of alkyl chloroformate was added. The reaction mixturewas stirred at room temperature 3e5 h. Precipitate was filtered offand solvent was evaporated in vacuo, resulting oil was purified bycolumn chromatography on silica gel (200 mL for 1 g of mixture)with PEeEtOAc 4:1 as an eluent.
  • 65
  • [ 7635-54-3 ]
  • [ 82912-42-3 ]
  • 1-(-)-menthyloxycarbonyl-aziridine-2-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With N-ethyl-N,N-diisopropylamine; In acetone; at 0 - 20℃; General procedure: 1.0 equiv of aziridine-2-carboxylic acid ester was mixed withacetone (2 mL of acetone for 1 mmol of ester) and 2.5 equiv ofdiisopropylethylamine. The reaction mixturewas cooled to 0 C and1.0 equiv of alkyl chloroformate was added. The reaction mixturewas stirred at room temperature 3e5 h. Precipitate was filtered offand solvent was evaporated in vacuo, resulting oil was purified bycolumn chromatography on silica gel (200 mL for 1 g of mixture)with PEeEtOAc 4:1 as an eluent.
  • 66
  • [ 7635-54-3 ]
  • 2-tert-butyl 2-(-)-menthyl aziridine-2,2-dicarboxylate [ No CAS ]
  • 67
  • [ 7635-54-3 ]
  • [ 1477517-29-5 ]
  • C23H36O4P [ No CAS ]
  • C23H36O4P [ No CAS ]
  • 68
  • [ 61-54-1 ]
  • [ 7635-54-3 ]
  • [ 945910-39-4 ]
  • 69
  • [ 7635-54-3 ]
  • bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) (3aR,3'aR,8aR,8'aR)-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-[3a,3'a-bipyrrolo[2,3-b]indole]-1,1'-dicarboxylate [ No CAS ]
  • bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) (3aS,3′aS,-8aS,8′aS)-2,2′,3,3′,8,8a,8′,8′a-octahydro-1H,1′H-[3a,3′-abipyrrolo[2,3-b]indole]-1,1′-dicarboxylate [ No CAS ]
  • 70
  • [ 7635-54-3 ]
  • bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) (3aR,3′aR,8aR,8′aR)-8,8′-dimethyl-2,2′,3,3′,8,8a,8′,8′a-octahydro-1H,1′H-[3a,3′a-bipyrrolo[2,3-b]indole]-1,1′-dicarboxylate [ No CAS ]
  • 71
  • [ 7635-54-3 ]
  • C11H21NO2 [ No CAS ]
  • 72
  • [ 7635-54-3 ]
  • 8-[([(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl]oxy}carbonyl)amino]quinoline-1-oxide [ No CAS ]
  • 73
  • [ 7635-54-3 ]
  • menthyl N-chlorocarbamate [ No CAS ]
  • 74
  • [ 7635-54-3 ]
  • C16H16O2 [ No CAS ]
  • 5,6,7,8-tetrahydrodibenzo[a,c][8]annulene-1,12-diol [ No CAS ]
  • 5,6,7,8-tetrahydrodibenzo[a,c][8]annulene-1,12-diol [ No CAS ]
  • 75
  • [ 7635-54-3 ]
  • ethyl 2-(2-[ethyl(phenyl)amino]phenyl)acetate [ No CAS ]
  • 1-ethyl-3-(L-menthyl) 2-(2-[ethyl(phenyl)amino]phenyl)propanedioate [ No CAS ]
  • 76
  • [ 7635-54-3 ]
  • [ 1202032-97-0 ]
  • 77
  • [ 7635-54-3 ]
  • C12H17O4P [ No CAS ]
  • C23H35O6P [ No CAS ]
  • 78
  • [ 7635-54-3 ]
  • C12H17O4P [ No CAS ]
  • C23H35O6P [ No CAS ]
  • 79
  • [ 7635-54-3 ]
  • (3aR,4R,5R,5aS,8aR,8bR)-5-Benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-ol [ No CAS ]
  • C30H44O8 [ No CAS ]
  • 80
  • [ 7635-54-3 ]
  • [ 602-09-5 ]
  • C31H32O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With triethylamine; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere; Example 2 BINOL-Menthyl Carbonate Coupling To a flame-dried 50 mL 3-neck flask was added 0.35 mmol of (R)-menthyl chloroformate. The flask was evacuated and backfilled with N2 three times, and submerged in an ice bath. 5 mL of a 0.07 M solution of racemic BINOL (0.35 mmol) in anhydrous dichloromethane (DCM) was cooled to 0 C. in an ice bath, and added via syringe to the flask under positive N2 pressure. 0.121 mL of TEA was then added to the reaction flask. The mixture was stirred under N2 and allowed to return to room temperature over 3 hours. The reaction was quenched with 5 mL of 1M HCl, stirred for 15 minutes, and extracted three times with DCM. The organic layer was then washed with brine, and dried over Na2SO4. Liquid was removed under vacuum to yield a pale waxy solid.
  • 81
  • [ 1202032-95-8 ]
  • [ 7635-54-3 ]
  • [ 1202032-97-0 ]
  • (S)-3-phenyl-3-oxido-2H-benzo[d][1,3]oxaphosphol-4-yl ((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) carbonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 5 - 60℃; To the suspension of 5 (40.00 g, 176.83 mmol) in CH3CN (120 mL) was added i-Pr2NEt (29.71 g, 229.88 mmol, 1.30 eq), followed by (+)-menthyl chloroformate (41.00 g, 187.44 mmol, 1.06 eq). The mixture was heated to 60 C. in ?0.5 h and held for ?1 h. The slurry was cooled to ?5 C. in 1 h and held for 2 h. The solid was filtered, rinsed with chilled MeCN (80 mL), and dried at ?40 C. under vacuum to give white solid product 6 (34.92 g, 48%). Chiral HPLC conditions for separation of the four possible diastereomers: Chiralcel IA-3, 4.6*150 mm, 3 mum, n-heptane/isopropanol =90/10, isocratic, 40 C., 1.2 mL/min; The ratio of the 2 diastereomers was determined as follows: 4.2 min (7, 0.1%), 5.8 min (6, 99.2%). (R)-3-(tert-Butyl)-3-oxido-2H-benzo[d][1,3]oxaphosphol-4-yl ((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) carbonate (6) via epimerization of (7). The filtrate from previous experiment was concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and extracted with 0.5 N HCl (100 mL). The organic layer was extracted with water (2*50 mL), dried over MgSO4, filtered and concentrated to give brownish oil (?40 g, ?97.93 mmol). The oil was dissolved in CH2Cl2 (200 mL) and cooled to ?0 C. Oxalyl chloride (18.64 g, 146.89 mmol, 1.50 eq) was added in ?15 min. The mixture was stirred at rt for 20 h. Solvents were removed under vacuum. MeCN (50 mL) and water (5 mL) were added. The mixture was stirred at 60 C. for 2 h, and the resulting suspension was cooled to ?3 C. in an ice-water bath for 1 h. The solid was filtered, rinsed with chilled MeCN (10 mL) and dried to give 6 as white solid (11.86 g, 17% based on 5) with 99.2% chiral purity. Another round of epimerization from the filtrate provided additional amount of 6 (8.25 g, 11%) with chiral purity of 99.5%.
  • 82
  • [ 7635-54-3 ]
  • [ 602-09-5 ]
  • C31H32O4 [ No CAS ]
  • C31H32O4 [ No CAS ]
  • 83
  • [ 7635-54-3 ]
  • [ 60261-46-3 ]
  • (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (S)-2-((diphenylphosphanyl) methyl)pyrrolidine-1-carboxylate [ No CAS ]
  • 84
  • [ 7635-54-3 ]
  • [ 428514-91-4 ]
  • (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (R)-2-((diphenylphosphanyl) methyl)pyrrolidine-1-carboxylate [ No CAS ]
  • 85
  • 1-(4-fluorobenzyl)indolin-5-amine [ No CAS ]
  • [ 7635-54-3 ]
  • (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (1-(4-fluorobenzyl)indolin-5-yl)carbamate [ No CAS ]
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