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[ CAS No. 1188-35-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1188-35-8
Chemical Structure| 1188-35-8
Chemical Structure| 1188-35-8
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Product Details of [ 1188-35-8 ]

CAS No. :1188-35-8 MDL No. :MFCD28155103
Formula : C13H22O6 Boiling Point : -
Linear Structure Formula :- InChI Key :CKNUUYLRWBMMIE-UHFFFAOYSA-N
M.W : 274.31 Pubchem ID :14911875
Synonyms :

Calculated chemistry of [ 1188-35-8 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.77
Num. rotatable bonds : 12
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 68.46
TPSA : 78.9 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.29
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.47
Log Po/w (SILICOS-IT) : 2.32
Consensus Log Po/w : 1.95

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.5
Solubility : 8.71 mg/ml ; 0.0317 mol/l
Class : Very soluble
Log S (Ali) : -2.44
Solubility : 0.989 mg/ml ; 0.00361 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.712 mg/ml ; 0.00259 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.23

Safety of [ 1188-35-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1188-35-8 ]

* 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 [ 1188-35-8 ]

[ 1188-35-8 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 64-17-5 ]
  • [ 5238-65-3 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid at 135℃;
  • 2
  • [ 923-42-2 ]
  • [ 1188-35-8 ]
  • 3
  • [ 101777-46-2 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride beim Erwaermen des Reaktionsprodukts mit Benzol, Aethanol und wenig Schwefelsaeure unter Entfernen des entstehenden Wassers;
  • 4
  • [ 64-17-5 ]
  • [ 923-42-2 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
100% With sulfuric acid; for 24.0h;Heating / reflux; Example 22; N1,N6-Bis-[2-(N-(2,3-dihydroxy-propyl)-5-(2-hydroxy-acetylamino)-2,4,6- triiodo-isophthalylamino)-hexyll]-N4'-(2,3-dihydroxy-propyl)-5-(2-hydroxy- acetylamino)-2,4,6-triiodo-isophthalamide; a) 3-ethoxycarbonylhexanedioic acid diethyl ester; To an ethanolic solution of 3-carboxyhexanedioic acid (10 g) was added a few drops of cone, sulphuric acid. The mixture was heated at reflux for 24 hours. After Aquesous work up and extraction in to DCM concentration of the dried organic layer yielded a clear oil. This was found to be 3-ethoxycarbonylhexanedioic acid diethyl ester by NMR in quantitative yield.
  • 6
  • [ 1188-35-8 ]
  • [ 89896-42-4 ]
YieldReaction ConditionsOperation in experiment
With ammonia
  • 7
  • [ 1188-35-8 ]
  • [ 38230-84-1 ]
YieldReaction ConditionsOperation in experiment
With sodium In benzene Heating;
  • 8
  • [ 1113-80-0 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate
  • 9
  • [ 1188-35-8 ]
  • [ 105-36-2 ]
  • 3,4-Bis-ethoxycarbonyl-heptanedioic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
(i) Na, EtOH, (ii) /BRN= 506456/, NaOEt; Multistep reaction;
  • 10
  • [ 1188-35-8 ]
  • [ 105-36-2 ]
  • [ 38230-85-2 ]
YieldReaction ConditionsOperation in experiment
(i) Na, EtOH, (ii) /BRN= 506456/, NaOEt; Multistep reaction;
  • 11
  • [ 1188-35-8 ]
  • [ 74-88-4 ]
  • [ 3033-53-2 ]
YieldReaction ConditionsOperation in experiment
(i) Na, (ii) /BRN= 969135/, (iii) HCl, AcOH; Multistep reaction;
  • 12
  • [ 1188-35-8 ]
  • [ 38230-84-1 ]
  • [ 54697-23-3 ]
YieldReaction ConditionsOperation in experiment
1: 10% 2: 65% With potassium hydroxide In N,N-dimethyl-formamide at 50 - 60℃;
With sodium ethanolate In toluene for 2h; Reflux; Overall yield = 88 %; We designed an alternate new route in Scheme 4 (novel method of this invention) to provide a functionalization handle, ethoxycarbonyl group, attached at 5- or 6- position of the cyclopenta[d]pyrimidine. Commercially available tricarboxylic acid (compound 8, Scheme 4) treated with oxalyl chloride and a catalytic amount of DMF afforded tricarbonyl chloride (compound 9, Scheme 4) in 95% yield. Triethyl esterificaton of compound 9, Scheme 4, with anhydrous ethanol in toluene gave the triethyl carboxylate (compound 10, Scheme 4) in almost quantitative yield. Cyclization of compound 10, Scheme4, with sodium ethoxide in toluene provided two diethoxycarbonyl cyclopentones compounds 1 la and 1 ib, Scheme 4, mixture in 88% total yield. Cyclization of the mixture of compounds 1 la and 1 lb regioisomers (Scheme 4)with acetamidine afforded a mixture of cyclopenta[d]pyrimidines (compounds 12a and 12b, Scheme 4) in 91% total yield.
  • 13
  • [ 1188-35-8 ]
  • [ 54697-23-3 ]
  • 3-oxo-cyclopentane-1,2-dicarboxylic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
9 g With hydrogenchloride; ethanol; sodium In benzene for 3h; Heating;
  • 14
  • [ 70600-48-5 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
85% With water; sodium chloride In dimethyl sulfoxide at 185 - 190℃; for 5.5h;
YieldReaction ConditionsOperation in experiment
1) Cyclisier., 2) Decarboxylier., 3) Verester. u. katalisier. nach Sato -> 3.3-Aethylendioxyd-cyclopentan-carbonsaeureaethylester;
YieldReaction ConditionsOperation in experiment
1-Cyan-butan-tricarbonsaeure-(3,3,4)-triaethylester, 1) sd. konz. HCl, 2) sd. ca. 25percentig. aethanol. H2SO4, 3 d;
corresp. tricarboxylic acid in C2H5OH, p-CH3-C6H4-SO3H, ethanolysis;
2, 1. HCl, 2. A./H2SO4;
Saeure II, EtOH;

  • 18
  • [ 56-23-5 ]
  • [ 1188-35-8 ]
  • [ 38230-84-1 ]
  • [ 54697-23-3 ]
YieldReaction ConditionsOperation in experiment
in vom Loesungsmittel abhaengigem Mengenverhaeltnis;
  • 19
  • [ 1188-35-8 ]
  • [ 64-17-5 ]
  • [ 38230-84-1 ]
  • [ 54697-23-3 ]
YieldReaction ConditionsOperation in experiment
in vom Loesungsmittel abhaengigem Mengenverhaeltnis;
  • 20
  • [ 1188-35-8 ]
  • [ 71-43-2 ]
  • [ 38230-84-1 ]
  • [ 54697-23-3 ]
YieldReaction ConditionsOperation in experiment
in vom Loesungsmittel abhaengigem Mengenverhaeltnis;
  • 21
  • [ 101568-03-0 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) KOH; 2.) aq. HCl / methanol; H2O / 5 h / Heating
  • 22
  • [ 2832-14-6 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / KOH / benzyltriethylammonium chloride (BTEAC) / dimethylformamide / 40 - 45 °C 2: 85 percent / NaCl, water / dimethylsulfoxide / 5.5 h / 185 - 190 °C
  • 23
  • [ 140-88-5 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 85 percent / KOH / benzyltriethylammonium chloride (BTEAC) / dimethylformamide / 30 - 45 °C 2: 85 percent / KOH / benzyltriethylammonium chloride (BTEAC) / dimethylformamide / 40 - 45 °C 3: 85 percent / NaCl, water / dimethylsulfoxide / 5.5 h / 185 - 190 °C
  • 24
  • [ 1119-85-3 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium cyanide; pyridine / 80 °C 2: sulfuric acid / 135 °C
  • 25
  • [ 13042-02-9 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium cyanide; pyridine 2: sulfuric acid / 135 °C
  • 26
  • [ 1188-35-8 ]
  • [ 15240-03-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) Na, EtOH, (ii) /BRN= 506456/, NaOEt 2: aq. HCl / Heating
  • 27
  • [ 1188-35-8 ]
  • [ 38230-87-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) Na, EtOH, (ii) /BRN= 506456/, NaOEt 2: aq. HCl / Heating 3: H2SO4
  • 28
  • [ 1188-35-8 ]
  • (1S,2S)-1-[2-(3-Methoxy-phenyl)-ethyl]-5-oxo-cyclopentane-1,2-dicarboxylic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Na / benzene / Heating 2: K / benzene
  • 29
  • [ 1188-35-8 ]
  • (1S,2S)-1-[2-(3-Methoxy-2-methyl-phenyl)-ethyl]-5-oxo-cyclopentane-1,2-dicarboxylic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Na / benzene / Heating 2: K / benzene
  • 30
  • [ 7209-00-9 ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaOEt 2: NaOEt
  • 31
  • [ 1188-35-8 ]
  • [ 206565-32-4 ]
YieldReaction ConditionsOperation in experiment
85% With methanol; sodium tetrahydroborate In <i>tert</i>-butyl alcohol for 1h; Heating / reflux; 22.b b) 3-Hvdroxymethyl-hexane-1 ,6-diol; To a solution of 3-ethoxycarbonylhexanedioic acid diethyl ester (10 g, 0.036 mol) in tert-butanol (100 mL) was added sodiumborohydride (6 g). The mixture was heated to reflux. Methanol (10 mL) was added in 3 aliquots over 30 minutes. The solution was heated at reflux for a further 30 minutes and allowed to cool. The solution was neutralised with 5 M hydrochloric acid with care. The solution was filtered and extracted with ethanol (2 x 50 mL). The solutions were combined and the solvent was removed at reduced pressure. The residue was extracted with ethanol (60 mL), filtered and concentrated at reduced pressure to yield the desired product as a clear, colourless liquid. This was analysed by NMR in D2O and found to be 3- hydroxymethylhexane-1 ,6-diol in a yield of 4.5 g (85%).
  • 32
  • [ 64-17-5 ]
  • C21H23N5O7 [ No CAS ]
  • [ 1188-35-8 ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate In toluene Scheme 4. Synthesis of cyclopenta[d]pyrimidine scaffold.We designed an alternate new route in Scheme 4 (novel method of this invention) to provide a functionalization handle, ethoxycarbonyl group, attached at 5- or 6- position of the cyclopenta[d]pyrimidine. Commercially available tricarboxylic acid (compound 8, Scheme 4) treated with oxalyl chloride and a catalytic amount of DMF afforded tricarbonyl chloride (compound 9, Scheme 4) in 95% yield. Triethyl esterificaton of compound 9, Scheme 4, with anhydrous ethanol in toluene gave the triethyl carboxylate (compound 10, Scheme 4) in almost quantitative yield. Cyclization of compound 10, Scheme4, with sodium ethoxide in toluene provided two diethoxycarbonyl cyclopentones compounds 1 la and 1 ib, Scheme 4, mixture in 88% total yield. Cyclization of the mixture of compounds 1 la and 1 lb regioisomers (Scheme 4)with acetamidine afforded a mixture of cyclopenta[d]pyrimidines (compounds 12a and 12b, Scheme 4) in 91% total yield.
  • 33
  • [ 1188-35-8 ]
  • [ 143-37-3 ]
  • C11H14N2O3 [ No CAS ]
  • C11H14N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-ethoxycarbonylhexane-1,6-dioic acid diethyl ester With sodium ethanolate In toluene for 2h; Reflux; Stage #2: acetamidine With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide for 4h; Reflux; Overall yield = 91 %; We designed an alternate new route in Scheme 4 (novel method of this invention) to provide a functionalization handle, ethoxycarbonyl group, attached at 5- or 6- position of the cyclopenta[d]pyrimidine. Commercially available tricarboxylic acid (compound 8, Scheme 4) treated with oxalyl chloride and a catalytic amount of DMF afforded tricarbonyl chloride (compound 9, Scheme 4) in 95% yield. Triethyl esterificaton of compound 9, Scheme 4, with anhydrous ethanol in toluene gave the triethyl carboxylate (compound 10, Scheme 4) in almost quantitative yield. Cyclization of compound 10, Scheme4, with sodium ethoxide in toluene provided two diethoxycarbonyl cyclopentones compounds 1 la and 1 ib, Scheme 4, mixture in 88% total yield. Cyclization of the mixture of compounds 1 la and 1 lb regioisomers (Scheme 4)with acetamidine afforded a mixture of cyclopenta[d]pyrimidines (compounds 12a and 12b, Scheme 4) in 91% total yield.
  • 34
  • [ 1188-35-8 ]
  • [ 143-37-3 ]
  • C9H12N2O2 [ No CAS ]
  • C9H12N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 42% 2: 40% Stage #1: 3-ethoxycarbonylhexane-1,6-dioic acid diethyl ester With sodium ethanolate In toluene for 2h; Reflux; Stage #2: acetamidine With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide for 4h; Reflux; Stage #3: With diisobutylaluminium hydride In tetrahydrofuran at -30℃; Scheme 5. Reduction of compound 12 (Scheme 5), and separation of compounds 13a and 13b, Scheme 5.Reduction of ester moieties in the compounds 12a and 12b, Scheme 5, mixture with excess DIBALH at -30 °C afforded the hydroxy group. In the 5-hydroxyl regioisomer 13a, Scheme 5, the hydroxyl group formed an intramolecular hydrogen bond with the 4-oxo. This did not occur with the regioisomer 13b, Scheme 5. Thus intramolecular hydrogen bond resulted in significantly lower polarity of 13a compared with 13b, Scheme 5, (TLC (CHC13/MeOH, 10:1), Rf 0.45 of 13a vs 0.15 of 13b). Separation of compounds 13a and 13b, SchemeS, was achieved by silca gel column chromatography in 42% and 40% isolated yields respectively.
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