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[ CAS No. 2387-23-7 ] {[proInfo.proName]}

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Chemical Structure| 2387-23-7
Chemical Structure| 2387-23-7
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Product Details of [ 2387-23-7 ]

CAS No. :2387-23-7 MDL No. :MFCD00003829
Formula : C13H24N2O Boiling Point : -
Linear Structure Formula :- InChI Key :ADFXKUOMJKEIND-UHFFFAOYSA-N
M.W :224.34 Pubchem ID :4277
Synonyms :
1,3-Dicyclohexylurea

Calculated chemistry of [ 2387-23-7 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 66.57
TPSA : 41.13 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) : -5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.68
Log Po/w (XLOGP3) : 3.09
Log Po/w (WLOGP) : 2.95
Log Po/w (MLOGP) : 2.56
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 2.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.91
Solubility : 0.274 mg/ml ; 0.00122 mol/l
Class : Soluble
Log S (Ali) : -3.62
Solubility : 0.0536 mg/ml ; 0.000239 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.81
Solubility : 0.345 mg/ml ; 0.00154 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.07

Safety of [ 2387-23-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2387-23-7 ]

* 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 [ 2387-23-7 ]
  • Downstream synthetic route of [ 2387-23-7 ]

[ 2387-23-7 ] Synthesis Path-Upstream   1~10

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YieldReaction ConditionsOperation in experiment
99.5% With bis(trichloromethyl) carbonate In 1-methyl-pyrrolidin-2-one at 30 - 40℃; for 6 h; Autoclave 1000 ml of NMP and 100 g of DCU were added to the autoclave at 30 ° C, stirred well, 200 g of BTC was added, and thenAdding the composite catalyst (the dosage ratio of DCU and composite catalyst is 1: 0.0001), raising the temperature to 40 DEG C,Reaction 6h, after the completion of the reaction, add triethylamine to adjust the pH to 7.5, hot filter, atmospheric distillation of the solvent, and then vacuum distillationDistillate, collecting 155 ± 1 ° C distillate, in the oven vacuum drying to obtain a white crystalline solid DCC.
88% With benzenesulfonyl chloride In dichloromethane at 40℃; for 3 h; Dicyclohexylurea (448.5, 2.0 mol) was added to dichloromethane (1600 ml).Maintain 40 ° C ± 2 ° C, slowly add 430 g of benzenesulfonyl chloride, drop, continue to stir for 3 h,Cool to 0-5 ° C, slowly add 5percent sodium hydroxide solution,Adjust pH=7, separate the organic layer, wash twice with water (800ml).Drying anhydrous sodium sulfate for 5 h, filtering, and distilling off the dichloromethane to recover dichloromethane.Switch to vacuum distillation and collect 155 ° C - 159 ° C / mmHg fraction,DCC (216.5 g, yield 88.0percent) was obtained.
82% With trichlorophosphate In chloroform; water at 55 - 60℃; for 2 h; The 5 kg N,N'-dicyclohexylurea raw material was placed in 10 kg of water and stirred for 40 min. The DCU was centrifuged and then dried in an oven at 110-120 ° C until the water was less than 0.5percent 175 g of trichloromethane was added to a three-necked flask, and 40.0 g of dried DCU was added with stirring. Weigh 30g of phosphorus oxychloride and add to a 250 mL dropping funnel. Stirring to the three-necked flask drop of phosphorus oxychloride, 30min added. After the addition, the reaction is maintained between 55-60 ° C for 2 hours. The reaction solution was poured into a dropping funnel. The reaction was filtered while hot, and the solid component was washed twice with 20 g of trichloromethane. The filtrate was allowed to stand for 1.5 hours and divided into an organic layer and an aqueous layer containing phosphate and sodium chloride. The water layer and the intermediate layer are filtered. The filtrate is allowed to stand for more than 12 hours. Take the supernatant as the water for the configuration of the lye. The solid components were washed twice with 20 g of trichloromethane and the organic layers of the washings were combined and the chloroform was separated by distillation. The components were collected by distillation under reduced pressure at 122-124 ° C / 6 mmHg to obtain a DCC product, As a raw material solvent reuse. 30 g of DCC was obtained in a yield of 82percent, and the purity of DCC as determined by gas chromatography was 99.5percent
78% With iodine; triethylamine; triphenylphosphine In dichloromethane for 1 h; Sonication General procedure: To a solution of 0.0844 g iodine (0.33 mmol) and 0.0872 g triphenylphosphine (0.33 mmol) in 2 cm3 CH2-Cl2 was added a solution of thiourea or urea(0.275 mmol) and 0.0701 g triethylamine (0.69 mmol) in2 cm3 CH2Cl2 under sonication. The reaction mixture was further sonicated until completion of the reaction as indicated by TLC. The crude mixture was concentrated under reduced pressure then purified by column chromatography using hexane to give the carbodiimide (see supporting information for characterization data of all products).

Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 39, p. 7047 - 7048
[2] Patent: CN105503656, 2016, A, . Location in patent: Paragraph 0027; 0028
[3] Synthesis, 1981, # 5, p. 373 - 374
[4] Bulletin de la Societe Chimique de France, 1981, vol. <II> 2, # 9-10, p. 361 - 364
[5] Patent: CN108424383, 2018, A, . Location in patent: Paragraph 0022; 0030; 0031
[6] Patent: CN104262200, 2016, B, . Location in patent: Paragraph 0038-0043
[7] Synthesis, 1983, # 2, p. 139 - 141
[8] Monatshefte fur Chemie, 2016, vol. 147, # 11, p. 1945 - 1949
[9] Zeitschrift fuer Chemie (Stuttgart, Germany), 1981, vol. 21, # 1, p. 25 - 27
[10] Biochemical Journal, 1957, vol. 65, p. 197,199[11] Biochemical Preparations, 1960, vol. 7, p. 5,11
[12] Justus Liebigs Annalen der Chemie, 1951, vol. 571, p. 83,85
[13] Justus Liebigs Annalen der Chemie, 1958, vol. 612, p. 11,17
[14] DRP/DRBP Org.Chem.,
[15] Patent: US2479498, 1946, ,
[16] Synthesis, 1980, # 9, p. 755 - 757
[17] Synthesis, 1987, # 5, p. 520 - 523
[18] Dalton Transactions, 2013, vol. 42, # 28, p. 10271 - 10276
[19] Journal of the American Chemical Society, 2018, vol. 140, # 5, p. 1627 - 1631
[20] Organic Process Research and Development, 2018, vol. 22, # 3, p. 399 - 402
[21] Patent: US2479498, 1946, ,
[22] DRP/DRBP Org.Chem.,
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Reference: [1] Chemical Communications, 1997, # 4, p. 347 - 348
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  • [ 603-35-0 ]
  • [ 538-75-0 ]
  • [ 791-28-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 1, p. 373 - 376
[2] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 1, p. 373 - 376
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1983, vol. 325, # 5, p. 787 - 802
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Reference: [1] Bulletin de la Societe Chimique de France, 1956, p. 1360
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  • [ 2407-11-6 ]
  • [ 1212-29-9 ]
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  • [ 4845-58-3 ]
Reference: [1] Journal of Organic Chemistry, 1937, vol. 2, p. 148,153
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Reference: [1] Heterocycles, 1997, vol. 46, # 1, p. 503 - 508
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Reference: [1] Heterocycles, 1997, vol. 46, # 1, p. 503 - 508
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Reference: [1] Patent: US4117004, 1978, A,
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  • [ 538-75-0 ]
  • [ 846023-24-3 ]
  • [ 2387-23-7 ]
Reference: [1] Patent: US2005/43537, 2005, A1, . Location in patent: Page/Page column 6
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