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[ CAS No. 26340-49-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 26340-49-8
Chemical Structure| 26340-49-8
Chemical Structure| 26340-49-8
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Product Details of [ 26340-49-8 ]

CAS No. :26340-49-8 MDL No. :MFCD10699391
Formula : C8H6IN Boiling Point : -
Linear Structure Formula :- InChI Key :ZPIHHIRJUPXETJ-UHFFFAOYSA-N
M.W : 243.04 Pubchem ID :11128498
Synonyms :

Calculated chemistry of [ 26340-49-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.02
TPSA : 15.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 2.77
Log Po/w (MLOGP) : 2.46
Log Po/w (SILICOS-IT) : 3.54
Consensus Log Po/w : 2.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.73
Solubility : 0.045 mg/ml ; 0.000185 mol/l
Class : Soluble
Log S (Ali) : -2.72
Solubility : 0.468 mg/ml ; 0.00192 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.24
Solubility : 0.014 mg/ml ; 0.0000577 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 26340-49-8 ]

Signal Word:Danger Class:6.1,8
Precautionary Statements:P501-P270-P264-P280-P391-P361+P364-P332+P313-P301+P312+P330-P302+P352+P312-P305+P351+P338+P310-P405 UN#:2928
Hazard Statements:H311-H302-H315-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 26340-49-8 ]

* 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.

  • Upstream synthesis route of [ 26340-49-8 ]
  • Downstream synthetic route of [ 26340-49-8 ]

[ 26340-49-8 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 26340-49-8 ]
  • [ 7135-31-1 ]
Reference: [1] Synthetic Communications, 2001, vol. 31, # 6, p. 947 - 951
  • 2
  • [ 120-72-9 ]
  • [ 26340-49-8 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: With carbon dioxide In tetrahydrofuran; hexane at -78℃; for 0.166667 h;
To a solution of indole (5.00 g, 42.68 mmol) in THF (80 mL) at 78 °C was added nBuLi (17 mL, 2.62M in hexane, 44.54 mmol). The resulting white suspension was stirred at 78 °C for 0.5 h, CO2 (gas)was then bubbled through the mixture for 10 min. The solvent was evaporated at 0 °C (ca. 20 1 hPa),the crystalline residue was dissolved in THF (100 mL) and cooled to 78 °C, and tBuLi (31 mL, 1.46 Min pentane, 45.26 mmol) was added dropwise. After stirring at 78 °C for 1 h, a solution of 1,2-diiodoethane (14.40 g, 51.09 mmol) in THF (80 mL) was added dropwise. After stirring at 78 °C for 1h, H2O (5 mL) was added dropwise and the solution was allowed to warm to RT. The reaction wasquenched with sat. aq. NH4Cl (50 mL). The layers were separated and the aqueous layer was extractedwith AcOEt (2 x 80 mL). The organic layers were combined, washed successively with 20percent aq.Na2S2O3 (80 mL), brine (80 mL), dried over MgSO4, and concentrated in vacuo. The residue waspurified by recrystallization from hexane/CH2Cl2 (70:1, 40 mL) to afford 6 (7.62 g, 74percent yield) as awhite crystal. The filtrate was concentrated in vacuo and the residue was purified by recrystallizationfrom hexane/CH2Cl2 (70:1, 10 mL) to afford 6 (0.56 g, 5percent yield) as a white crystal. The filtrate wasconcentrated in vacuo and the residue was purified by recrystallization from hexane/CH2Cl2 (70:1, 8 mL)to afford 6 (0.27 g, 3percent yield) as a light purple crystal. The filtrate was concentrated in vacuo and theresidue was purified by flash chromatography (silica gel, hexane/AcOEt = 35:1) to afford 6 (0.42 g, 4percentyield) as a white crystal. Iodoindole 6 was prepared in total 86 percent yield.
36% With copper(l) iodide; potassium iodide In dichloromethane at 20℃; for 2 h; Inert atmosphere General procedure: A solution of indole, azaindole or pyrrole (0.1 mmol) in dichloromethane (5 mL) was added to a suspension of 1:1 (W/W) ICl (concentration indicated in the Table; 0.1 mmol = 162 mg) and Celite.(R). (162 mg) ratio in dichloromethane (10 mL). The mixture was stirred at room temperature for the time indicated in Tables 1-4. The reaction mixture was then poured into saturated thiosulfate solution (20 mL) extracted with dichloromethane (2 x 15 mL). The organic layer was washed in brine and, dried over sodium sulfate and the solvent was removed at reduced pressure. The desired compound was purified by chromatography column using hexane and ethyl acetate mixtures as eluting solvent. Yields of iodinated compounds are summarized in Tables 1-4. All the compounds were characterized by IR, NMR and were compared with authentic samples.
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 44, p. 7661 - 7664
[2] Tetrahedron, 2001, vol. 57, # 24, p. 5199 - 5212
[3] Tetrahedron Letters, 2001, vol. 42, # 16, p. 2949 - 2951
[4] Tetrahedron Letters, 2007, vol. 48, # 10, p. 1805 - 1808
[5] Tetrahedron, 2013, vol. 69, # 45, p. 9481 - 9493
[6] Chemical Communications, 1999, # 17, p. 1761 - 1762
[7] Angewandte Chemie - International Edition, 2006, vol. 45, # 14, p. 2274 - 2277
[8] Tetrahedron, 2012, vol. 68, # 31, p. 6269 - 6275
[9] Journal of Organic Chemistry, 1992, vol. 57, # 8, p. 2495 - 2497
[10] Tetrahedron Letters, 1997, vol. 38, # 39, p. 6787 - 6790
[11] Synthesis, 2002, # 13, p. 1810 - 1812
[12] Chemistry - A European Journal, 2010, vol. 16, # 5, p. 1670 - 1678
[13] Organic Letters, 2013, vol. 15, # 1, p. 140 - 143
[14] RSC Advances, 2013, vol. 3, # 36, p. 16144 - 16151
[15] Synlett, 2017, vol. 28, # 16, p. 2189 - 2193
[16] Patent: US2010/144726, 2010, A1,
  • 3
  • [ 40899-71-6 ]
  • [ 26340-49-8 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 0℃; for 2.5 h;
Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃; for 20 h;
Stage #3: With sodium t-butanolate In 1,4-dioxane at 80℃; for 3 h;
To a solution of i-Pr2NH (3.5 mL, 25 mmol) in THF was added 1.64 M solution of n-BuLi inn-hexane (14.4 mL, 24 mmol) at –78 °C, and the mixture was stirred at 0 °C for 30 min. After thereaction mixture was cooled to –78 °C, a solution of S6 (3.0 g, 12 mmol) in THF (20 mL) wasadded. The mixture was stirred at –78 °C for 1.5 h, and then at 0 °C for 1 h. To this reactionmixture was added I2 (3.0 g, 12 mmol) at –78 °C, and the mixture was stirred at ambienttemperature for 20 h. The reaction was quenched with 3percent aqueous solution of Na2CO3 and themixture was extracted with EtOAc. The combined organic layers were washed with water andbrine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified bycolumn chromatography on silica gel (n-hexane–EtOAc 20:1) to give a 2:1 mixture of 2-iodinatedS6 and unreacted S6 (3.66 g). To a solution of the obtained mixture (3.66 g) in dioxane (37 mL)was added NaOt-Bu (1.0 g, 11 mmol) at ambient temperature, and the mixture was stirred at 80 °Cfor 3 h. The reaction was quenched with water, and the mixture was extracted with EtOAc. Thecombined organic layers were dried over MgSO4 and concentrated under reduced pressure. Theresidue was purified by column chromatography on silica gel (n-hexane–EtOAc 100:1) to give2-iodo-1H-indole (S7, 1.6 g, 6.6 mmol, 55percent) as a colorless solid.
Reference: [1] Synlett, 2017, vol. 28, # 16, p. 2189 - 2193
[2] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 2, p. 505 - 509
[3] RSC Advances, 2013, vol. 3, # 36, p. 16144 - 16151
  • 4
  • [ 99275-44-2 ]
  • [ 26340-49-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 2, p. 505 - 509
[2] RSC Advances, 2013, vol. 3, # 36, p. 16144 - 16151
  • 5
  • [ 99275-45-3 ]
  • [ 26340-49-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 2, p. 505 - 509
  • 6
  • [ 476004-81-6 ]
  • [ 26340-49-8 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 1, p. 140 - 143
  • 7
  • [ 1477-50-5 ]
  • [ 26340-49-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 22, p. 7582 - 7591
  • 8
  • [ 87954-27-6 ]
  • [ 26340-49-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 2, p. 505 - 509
  • 9
  • [ 75400-67-8 ]
  • [ 26340-49-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 2, p. 505 - 509
  • 10
  • [ 26340-49-8 ]
  • [ 74-88-4 ]
  • [ 75833-63-5 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: at 0 - 20℃; for 1 h;
[00169] A solution of 2-iodo-lH-indole (1) (1.50 g, 6.17 mmol) in THF (20 mL) was added to a suspension of 60percent NaH (0.37 g, 9.25 mmol) at 0 °C and the resulting solution was stirred for 10 min. Methyl iodide (1.75 g, 12.3 mmol) was added dropwise and the reaction mixture was allowed to warm slowly from 0 °C to rt over 1 h. The reaction was quenched with saturated NH4CI solution (15 mL) and extracted with ethyl acetate. The organic layer was dried over Na2S04and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to afford 1.27 g (80percent) of the title compound as a pale yellow oil. FontWeight="Bold" FontSize="10" H NMR (400 MHz, CDCI3) δ 7.71 (d, J = 7.6 Hz, 1H), 7.29 (d, J= 8 Hz, 1H), 7.14 (t, J = 7.6 Hz, 1H), 7.06 (t, J= 7.6 Hz, 1H), 6.78 (s, 1H), 3.74 (s, 3H).
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 44, p. 7661 - 7664
[2] Tetrahedron Letters, 2005, vol. 46, # 8, p. 1325 - 1328
[3] Organic Preparations and Procedures International, 2001, vol. 33, # 6, p. 615 - 619
[4] Patent: WO2015/197861, 2015, A1, . Location in patent: Paragraph 00168-00169
[5] Journal of Organic Chemistry, 1992, vol. 57, # 8, p. 2495 - 2497
[6] Tetrahedron Letters, 1997, vol. 38, # 39, p. 6787 - 6790
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