Home Cart 0 Sign in  
X

[ CAS No. 2719-27-9 ] {[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+
3d Animation Molecule Structure of 2719-27-9
Chemical Structure| 2719-27-9
Chemical Structure| 2719-27-9
Structure of 2719-27-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 2719-27-9 ]

Related Doc. of [ 2719-27-9 ]

Alternatived Products of [ 2719-27-9 ]

Product Details of [ 2719-27-9 ]

CAS No. :2719-27-9 MDL No. :MFCD00001456
Formula : C7H11ClO Boiling Point : -
Linear Structure Formula :- InChI Key :RVOJTCZRIKWHDX-UHFFFAOYSA-N
M.W : 146.61 Pubchem ID :75938
Synonyms :

Calculated chemistry of [ 2719-27-9 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.65
TPSA : 17.07 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) : -5.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 2.94
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 1.68
Log Po/w (SILICOS-IT) : 2.46
Consensus Log Po/w : 2.29

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.428 mg/ml ; 0.00292 mol/l
Class : Soluble
Log S (Ali) : -2.96
Solubility : 0.161 mg/ml ; 0.0011 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.86
Solubility : 2.03 mg/ml ; 0.0138 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 2719-27-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H227-H314-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2719-27-9 ]

* 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 [ 2719-27-9 ]
  • Downstream synthetic route of [ 2719-27-9 ]

[ 2719-27-9 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 81128-26-9 ]
  • [ 2719-27-9 ]
  • [ 6662-72-2 ]
  • [ 81128-30-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 6, p. 2003 - 2010
  • 2
  • [ 98-89-5 ]
  • [ 2719-27-9 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride In dodecane; benzene at 20℃; for 1 h; Heating / reflux 20.0 g (cyclohexanecarboxylic acid: 6.95 g, 0.054 mol) of the cyclohexanecarboxylic acid solution and 1.0 g of n-dodecane as an internal standard material were added to a reactor equipped with a condenser and a Dean-Stark water separator. After adding 90 ml of benzene, about 25 ml of benzene was distilled off in the nitrogen atmosphere to make the anhydrous solution. The temperature of the reactant solution was lowered to the atmospheric temperature and 6.0 ml (9.8 g, 0.082 mol) of thionyl chloride was added for one hour of reflux. [0046] After the reaction, part of the reactant solution was collected and reacted with methanol including a small amount of triethylamine in order to identify the product, cyclohexanecarbonyl chloride. The yield of methyl cyclohexane carboxylate was analyzed by GC. As a result, cyclohexanecarbonyl chloride was produced with a conversion rate of more than 99percent and a selectivity of more than 99percent.
99% With thionyl chloride In dodecane; hexane; benzene at 20℃; for 1 h; Heating / reflux 25 ml (cyclohexanecarboxylic acid: 6.0 g, 0.047 mol) of the cyclohexanecarboxylic acid solution and 1.0 g of n-dodecane as an internal standard material were added to a reactor equipped with a condenser and a Dean-Stark water separator. After adding 30 ml of benzene and 60 ml of n-hexane, about 25 ml of n-hexane was distilled off in the nitrogen atmosphere to make the internal solution anhydrous. The temperature of the reactant solution was lowered to the atmospheric temperature and 3.4 ml (5.55 g, 0.047 mol) of thionyl chloride was added for one hour of reflux. After the reaction, part of the reactant solution was collected and reacted with methanol in order to identify the product, cyclohexanecarbonyl chloride, the selectivity of which was determined as 99percent.
99% With phosphorus trichloride In dodecane; benzene at 20℃; for 1 h; Heating / reflux The procedures were performed in the same manner as described in the step (ii) of Example 1, excepting that phosphorous trichloride was used instead of thionyl chloride as a chlorinating compound to prepare cyclohexanecarbonyl chloride. [0054] More specifically, 20.0 g (cyclohexanecarboxylic acid: 6.95 g, 0.054 mol) of the cyclohexanecarboxylic acid solution and 1.0 g of n-dodecane as an internal standard material were added to a reactor equipped with a condenser and a Dean-Stark water separator. After adding 90 ml of benzene, about 25 ml of benzene was distilled off in the nitrogen atmosphere to make the internal solution anhydrous. The temperature of the reactant solution was lowered to the atmospheric temperature and 2.4 ml (3.77 g, 0.027 mol) of phosphorous trichloride was added for one hour of reflux. [0055] After the reaction, part of the reactant solution was collected and reacted with methanol including a small amount of triethylamine in order to identify the product, cyclohexanecarbonyl chloride. The yield of methyl cyclohexane carboxylate was analyzed by GC. As a result, cyclohexanecarbonyl chloride was produced with a conversion rate of more than 99percent and a selectivity of more than 99percent.
92% for 3 h; Reflux In step (2), cyclohexanecarboxylic acid 20g, catalytic amount of pyridine added to the reaction flask, was slowly added dropwise thionyl chloride, Pill control time 30min, stirring was continued refluxed for 3 hours, distilling off the excess titanium thionyl chloride, the residue was distilled under reduced pressure 85 / 3999Pa fraction, 20.8 g of the product weight, 92percent yield.

Reference: [1] Patent: US2004/73068, 2004, A1, . Location in patent: Page 3
[2] Patent: US2004/73068, 2004, A1, . Location in patent: Page 4
[3] Patent: US2004/73068, 2004, A1, . Location in patent: Page 3
[4] Canadian Journal of Chemistry, 1996, vol. 74, # 12, p. 2401 - 2412
[5] Organic Syntheses, 1983, vol. 61, p. 134 - 134
[6] Patent: CN107417608, 2017, A, . Location in patent: Paragraph 0031; 0033; 0036; 0037
[7] Synthesis, 1983, # 4, p. 306 - 308
[8] Organic and Biomolecular Chemistry, 2007, vol. 5, # 24, p. 3993 - 4000
[9] Chemische Berichte, 1897, vol. 30, p. 1941
[10] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1911, vol. 153, p. 773
[11] Angewandte Chemie, 1960, vol. 72, # 22, p. 836 - 845
[12] Journal of Organic Chemistry, 1971, vol. 36, # 22, p. 3429 - 3437
[13] Archiv der Pharmazie, 1972, vol. 305, # 4, p. 309 - 314
[14] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1968, # 5, p. 1061 - 1063[15] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1968, # 5, p. 1117 - 1120
[16] Journal of Organic Chemistry, 1982, vol. 47, # 26, p. 5093 - 5096
[17] Tetrahedron, 1988, vol. 44, # 12, p. 3501 - 3512
[18] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 6, p. 2426 - 2436
[19] Journal of the American Chemical Society, 1987, vol. 109, p. 7488
[20] Heterocycles, 1987, vol. 25, p. 449 - 462
[21] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1986, vol. 41, # 8, p. 1011 - 1014
[22] Synthetic Communications, 1993, vol. 23, # 12, p. 1775 - 1781
[23] Australian Journal of Chemistry, 1986, vol. 39, # 2, p. 249 - 257
[24] Tetrahedron, 1991, vol. 47, # 34, p. 7091 - 7108
[25] Recueil: Journal of the Royal Netherlands Chemical Society, 1981, vol. 100, # 1, p. 21 - 24
[26] Canadian Journal of Chemistry, 1994, vol. 72, # 1, p. 142 - 145
[27] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2608 - 2612
[28] Gazzetta Chimica Italiana, 1988, vol. 118, # 12, p. 819 - 820
[29] Journal of Chemical Research, Miniprint, 1983, # 3, p. 664 - 677
[30] Australian Journal of Chemistry, 1996, vol. 49, # 12, p. 1287 - 1291
[31] Journal of Organic Chemistry, 1998, vol. 63, # 7, p. 2062 - 2063
[32] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 6, p. 1479 - 1487
[33] Synthesis, 2001, # 6, p. 914 - 918
[34] Archiv der Pharmazie, 2001, vol. 334, # 2, p. 45 - 52
[35] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 265 - 286
[36] Tetrahedron Asymmetry, 2002, vol. 13, # 6, p. 579 - 585
[37] Farmaco, 2002, vol. 57, # 9, p. 771 - 775
[38] Journal of Organic Chemistry, 2001, vol. 66, # 3, p. 697 - 706
[39] European Journal of Organic Chemistry, 2000, # 11, p. 2119 - 2133
[40] Russian Journal of Applied Chemistry, 2006, vol. 79, # 6, p. 1035 - 1037
[41] Russian Journal of Applied Chemistry, 2006, vol. 79, # 12, p. 1982 - 1985
[42] Journal of Fluorine Chemistry, 2007, vol. 128, # 10, p. 1235 - 1240
[43] Patent: EP1443046, 2004, A1, . Location in patent: Page 38
[44] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9473 - 9475
[45] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 6, p. 1702 - 1706
[46] Synlett, 2010, # 20, p. 3049 - 3052
[47] Journal of Medicinal Chemistry, 2010, vol. 53, # 21, p. 7664 - 7674
[48] Tetrahedron, 2011, vol. 67, # 20, p. 3659 - 3667
[49] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 2, p. 635 - 644
[50] Patent: WO2011/153197, 2011, A1, . Location in patent: Page/Page column 99-100
[51] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7219 - 7223
[52] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 4, p. 1333 - 1336
[53] Tetrahedron Letters, 2012, vol. 53, # 43, p. 5742 - 5744
[54] Journal of the American Chemical Society, 2012, vol. 134, # 45, p. 18570 - 18572
[55] Journal of the American Chemical Society, 2017, vol. 139, # 9, p. 3344 - 3347
[56] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9589 - 9606
[57] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 191 - 196
[58] Journal of the American Chemical Society, 2013, vol. 135, # 16, p. 6030 - 6032
[59] Chemical Communications, 2013, vol. 49, # 68, p. 7546 - 7548
[60] Synthetic Communications, 2013, vol. 43, # 21, p. 2955 - 2965
[61] ChemMedChem, 2013, vol. 8, # 6, p. 994 - 1001
[62] European Journal of Medicinal Chemistry, 2013, vol. 70, p. 548 - 557
[63] Central European Journal of Chemistry, 2014, vol. 12, # 1, p. 115 - 125
[64] Molecules, 2013, vol. 18, # 12, p. 14920 - 14934
[65] Organic Letters, 2015, vol. 17, # 5, p. 1200 - 1203
[66] Chemical Communications, 2015, vol. 51, # 24, p. 5089 - 5092
[67] Organic Letters, 2015, vol. 17, # 11, p. 2688 - 2691
[68] Journal of Organometallic Chemistry, 2015, vol. 794, p. 136 - 145
[69] Angewandte Chemie - International Edition, 2015, vol. 54, # 46, p. 13686 - 13690[70] Angew. Chem., 2015, vol. 127, # 46, p. 13694,1
[71] Chemical Communications, 2015, vol. 51, # 80, p. 14929 - 14932
[72] Chemistry Letters, 2015, vol. 44, # 10, p. 1365 - 1367
[73] Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 887 - 893
[74] Journal of the American Chemical Society, 2016, vol. 138, # 24, p. 7516 - 7519
[75] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 351 - 364
[76] International Journal of Biological Macromolecules, 2017, vol. 103, p. 1096 - 1106
[77] Tetrahedron Letters, 2017, vol. 58, # 10, p. 973 - 976
[78] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 8, p. 824 - 829
[79] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 17, p. 4075 - 4081
[80] Tetrahedron Letters, 2017, vol. 58, # 37, p. 3640 - 3642
[81] Journal of the American Chemical Society, 2017, vol. 139, # 35, p. 12153 - 12156
[82] Angewandte Chemie - International Edition, 2018, vol. 57, # 4, p. 929 - 932[83] Angew. Chem., 2018, vol. 130, p. 941 - 944,4
[84] Organic Letters, 2018, vol. 20, # 8, p. 2468 - 2471
[85] Organic Letters, 2018, vol. 20, # 12, p. 3487 - 3490
[86] Tetrahedron Letters, 2018, vol. 59, # 23, p. 2299 - 2301
[87] Patent: WO2018/107216, 2018, A1, . Location in patent: Page/Page column 26; 52; 53
[88] Patent: EP3357916, 2018, A1, . Location in patent: Paragraph 0093
[89] Angewandte Chemie - International Edition, 2018, vol. 57, # 40, p. 13106 - 13109[90] Angew. Chem., 2018, vol. 130, # 40, p. 13290 - 13293,4
[91] Patent: WO2009/118596, 2009, A2, . Location in patent: Page/Page column 27-28
  • 3
  • [ 2043-61-0 ]
  • [ 2719-27-9 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 3, p. 931 - 939
[2] Tetrahedron Letters, 2017, vol. 58, # 26, p. 2533 - 2536
  • 4
  • [ 79-37-8 ]
  • [ 110-82-7 ]
  • [ 2719-27-9 ]
Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 329,332
[2] Journal of the American Chemical Society, 1942, vol. 64, p. 329,332
[3] Journal of the American Chemical Society, 1940, vol. 62, p. 454[4] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[5] Journal of the American Chemical Society, 1940, vol. 62, p. 454[6] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[7] Journal of the American Chemical Society, 1940, vol. 62, p. 454[8] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[9] Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1952, vol. 56, p. 779
[10] Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1956, vol. 60, p. 956
[11] Journal of the American Chemical Society, 1940, vol. 62, p. 454[12] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[13] Patent: US2326228, 1940, ,
[14] Patent: CH228931, 1942, ,
[15] Patent: US2326228, 1940, ,
[16] Patent: US2326229, 1940, ,
  • 5
  • [ 65-85-0 ]
  • [ 2719-27-9 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 7, p. 1286 - 1290[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 7, p. 1427 - 1432
  • 6
  • [ 119520-52-4 ]
  • [ 2719-27-9 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 12, p. 3501 - 3512
  • 7
  • [ 119541-42-3 ]
  • [ 2719-27-9 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 12, p. 3501 - 3512
  • 8
  • [ 75-44-5 ]
  • [ 110-82-7 ]
  • [ 2719-27-9 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 454[2] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[3] Patent: CH228931, 1944, ,
[4] Journal of the American Chemical Society, 1940, vol. 62, p. 454[5] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[6] Journal of the American Chemical Society, 1940, vol. 62, p. 454[7] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[8] Patent: US2326228, 1940, ,
[9] Patent: CH228931, 1942, ,
[10] Patent: CH228931, 1942, ,
  • 9
  • [ 110-82-7 ]
  • [ 201230-82-2 ]
  • [ 542-18-7 ]
  • [ 2719-27-9 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 16, p. 2119 - 2122
  • 10
  • [ 79-37-8 ]
  • [ 110-82-7 ]
  • [ 94-36-0 ]
  • [ 2719-27-9 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 454[2] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[3] Journal of the American Chemical Society, 1940, vol. 62, p. 454[4] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[5] Journal of the American Chemical Society, 1940, vol. 62, p. 454[6] Journal of the American Chemical Society, 1942, vol. 64, p. 332
[7] Patent: US2326228, 1940, ,
[8] Patent: US2326229, 1940, ,
[9] Patent: US2326228, 1940, ,
[10] Patent: CH228931, 1942, ,
  • 11
  • [ 75-44-5 ]
  • [ 110-82-7 ]
  • [ 542-18-7 ]
  • [ 2719-27-9 ]
Reference: [1] Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1956, vol. 60, p. 956
  • 12
  • [ 924-50-5 ]
  • [ 2719-27-9 ]
  • [ 29342-05-0 ]
YieldReaction ConditionsOperation in experiment
34%
Stage #1: With aluminum (III) chloride In dichloromethane for 3 h; Reflux
Stage #2: With hydroxylamine hydrochloride; sodium acetate In methanol; water at 20 - 30℃; for 20 h;
Stage #3: With sodium hydroxide In methanol; water at 20℃; for 1 h;
30g of aluminum trichloride dissolved in 50ml of dichloromethane, dropwise under stirring into the mixed solution, and HBTA-2 HBTA-02, the control is completed in 20min dropwise, slowly and stirring was continued at reflux for 3 hours on a water bath, until no evolution of hydrogen chloride gas, cooled, slowly poured into ice water 100ml and a mixture of 100ml of concentrated hydrochloric acid, the organic layer was separated, the aqueous phase was extracted with dichloromethane, the combined organic phases were washed with sodium bicarbonate solution and then with water until neutral, dried over anhydrous magnesium sulfate, and evaporated dichloro methane, distillation under reduced pressure collecting 179 / 266Pa distillate, the product 5-oxo-3-methyl-5-cyclohexyl-3-pentenoate 16.7g, 75percent yield. In step (4), a mixture of 11.2g of HBTA-3A and the HBTA-3B, 4.1g of hydroxylamine hydrochloride, dubbed 8ml methanol solution at room temperature with stirring, was added 15ml water and 4.5g of sodium acetate dubbed aqueous solution, vigorously stirred at 30 20 hours and then added to 8ml of 4g of sodium hydroxide aqueous solution under cooling dubbed stirred at room temperature for 1 hour, extracted with benzene, the aqueous solution was acidified to pH 6, a precipitate was filtered, the aqueous phase continue was acidified to pH 3, and extracted with methylene chloride, methylene chloride recovered, concentrated hydrochloric acid was added to the residue, a precipitate was filtered and the precipitate washed twice was recrystallized from ethanol and washed with an aqueous solution to give the product 5g, 34percent yield.
Reference: [1] Patent: CN107417608, 2017, A, . Location in patent: Paragraph 0031; 0033; 0039; 0040-0042
[2] Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 8 a, p. 1311 - 1316
  • 13
  • [ 2719-27-9 ]
  • [ 54396-74-6 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 26, p. 5093 - 5096
  • 14
  • [ 2719-27-9 ]
  • [ 56077-28-2 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 29, p. 3714 - 3717
[2] Synthetic Communications, 2013, vol. 43, # 21, p. 2955 - 2965
  • 15
  • [ 2719-27-9 ]
  • [ 18107-18-1 ]
  • [ 56077-28-2 ]
Reference: [1] Journal of Fluorine Chemistry, 2013, vol. 153, p. 151 - 161
  • 16
  • [ 186581-53-3 ]
  • [ 2719-27-9 ]
  • [ 56077-28-2 ]
Reference: [1] Chemische Berichte, 1963, vol. 96, p. 465 - 469
  • 17
  • [ 372-09-8 ]
  • [ 2719-27-9 ]
  • [ 62455-70-3 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With [2,2]bipyridinyl; n-butyllithium; magnesium sulfate In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere
Stage #2: at -78 - 20℃; Inert atmosphere
Stage #3: With hydrogenchloride In tetrahydrofuran; methanol; hexane; water
General procedure: Cyanoacetic acid (1.7 g, 20 mmol, 2 equiv), 0.2 mg MgSO4, and ~1 mg 2,2'-bipyridyl was dissolved in tetrahydrofuran (100 mL) and placed in a 500 mL three-neck flask fitted with two dropping funnels and a mechanical stirrer. The system was flushed with nitrogen and cooled to -78 C with a dry ice/ acetone bath. An n-butyl lithium solution (25 mL, 1.6 M in hexanes; 40 mmol, 4 equiv) was added via a dropping funnel with stirring. Once the solution turned slightly purple it was stirred (30 min) after which the acid chloride (10 mmol, 1 equiv) in 5 mL of methanol was added drop-wise with stirring. During this process, the cloudy solution took on a yellow color. The solution was stirred at -78 C for one hour, then the bath was removed and the reaction was allowed to return to room temperature for one hour. An HCl solution (50 mL, 1M) was added drop-wise. At this point, the reaction became clear, while remaining yellow. Water (25 mL) and CH3Cl (50 mL) were added. The aqueous layer was extracted three times with the same volume of CH3Cl. The combined organic layers were washed with two portions (50 mL) of saturated sodium bicarbonate solution and dried over magnesium sulfate, filtered, and reduced on a rotoevaporator. Samples were purified by flash chromatography 6 Hex : 1 EtOAc resulting in percent yields from 50-80percent.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 19, p. 2440 - 2442
  • 18
  • [ 1116-98-9 ]
  • [ 2719-27-9 ]
  • [ 62455-70-3 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 5, p. 1137 - 1143
  • 19
  • [ 2719-27-9 ]
  • [ 455264-97-8 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 13, p. 2343 - 2346
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 2719-27-9 ]

Aliphatic Cyclic Hydrocarbons

Chemical Structure| 13170-66-6

[ 13170-66-6 ]

Cyclohexane-1,4-dicarbonyl dichloride

Similarity: 1.00

Chemical Structure| 84855-54-9

[ 84855-54-9 ]

Trans-4-isopropylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 67589-91-7

[ 67589-91-7 ]

Trans-4-hexylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 146606-05-5

[ 146606-05-5 ]

Cis-4-butylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 80022-86-2

[ 80022-86-2 ]

Trans-4-octylcyclohexanecarbonyl chloride

Similarity: 1.00

Chlorides

Chemical Structure| 13170-66-6

[ 13170-66-6 ]

Cyclohexane-1,4-dicarbonyl dichloride

Similarity: 1.00

Chemical Structure| 84855-54-9

[ 84855-54-9 ]

Trans-4-isopropylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 67589-91-7

[ 67589-91-7 ]

Trans-4-hexylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 146606-05-5

[ 146606-05-5 ]

Cis-4-butylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 80022-86-2

[ 80022-86-2 ]

Trans-4-octylcyclohexanecarbonyl chloride

Similarity: 1.00

Acyl Chlorides

Chemical Structure| 67589-87-1

[ 67589-87-1 ]

Trans-4-ethylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 84855-54-9

[ 84855-54-9 ]

Trans-4-isopropylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 67589-91-7

[ 67589-91-7 ]

Trans-4-hexylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 146606-05-5

[ 146606-05-5 ]

Cis-4-butylcyclohexanecarbonyl chloride

Similarity: 1.00

Chemical Structure| 80022-86-2

[ 80022-86-2 ]

Trans-4-octylcyclohexanecarbonyl chloride

Similarity: 1.00