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[ CAS No. 111-16-0 ] {[proInfo.proName]}

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Chemical Structure| 111-16-0
Chemical Structure| 111-16-0
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Product Details of [ 111-16-0 ]

CAS No. :111-16-0 MDL No. :MFCD00004425
Formula : C7H12O4 Boiling Point : -
Linear Structure Formula :(CH2)5(COOH)2 InChI Key :WLJVNTCWHIRURA-UHFFFAOYSA-N
M.W : 160.17 Pubchem ID :385
Synonyms :
Heptanedioic acid;1,5-Pentanedicarboxylic acid;1,7-Heptanedioic acid
Chemical Name :Heptanedioic acid

Calculated chemistry of [ 111-16-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 39.31
TPSA : 74.6 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) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.94
Log Po/w (XLOGP3) : 0.61
Log Po/w (WLOGP) : 1.11
Log Po/w (MLOGP) : 0.6
Log Po/w (SILICOS-IT) : 0.47
Consensus Log Po/w : 0.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.82
Solubility : 24.2 mg/ml ; 0.151 mol/l
Class : Very soluble
Log S (Ali) : -1.75
Solubility : 2.84 mg/ml ; 0.0178 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.64
Solubility : 36.7 mg/ml ; 0.229 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 111-16-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 111-16-0 ]

* 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 [ 111-16-0 ]

[ 111-16-0 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 111-16-0 ]
  • [ 1732-08-7 ]
  • [ 20291-40-1 ]
YieldReaction ConditionsOperation in experiment
68% With hydrogenchloride; In methanol; ethyl acetate; A. Methyl hydrogen pimelate (7) A mixture of pimelic acid (15) (75.1 g, 0.47 mol), dimethyl pimelate (50.1 g, 0.27 mol), hydrochloric acid (8 mL, 0.1 mol), methanol (25 mL, 0.62 mol) and di-n-butyl ether (20 mL) was heated (oil bath: 100-110 C.) under N2 overnight. After cooling to room temperature, EtOAc (200 mL) was added and the mixture was washed with water (2*100 mL), saturated NaCl (2*100 mL) and dried (Na2 SO4). The crude oil was fractionally distilled (vigreux, 125-130 C., 0.7 mm Hg) to provide a clear oil (55.5 g, 68%, purity≅95%. Based on NMR analysis, the clear oil was determined to be methyl hydrogen pimelate (7) (1 H NMR)): TLC (SiO2, MeOH/EtOAc/hexane (2:8:15, v/v)) Rf =0.25-0.34; 1 H NMR (300 MHz, CDCl3) δ3.67 (s, 3 H), 2.40-2.28 (m, 4 H), 1.72-1.58 (m, 4 H), 1.45-1.32 (m, 2 H).
  • 2
  • [ 111-16-0 ]
  • [ 1454-85-9 ]
  • [ 26719-32-4 ]
  • 3
  • [ 6066-82-6 ]
  • [ 111-16-0 ]
  • [ 74648-14-9 ]
YieldReaction ConditionsOperation in experiment
71% With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 18.0h; [00350] Heptanedioic acid (1.6 g, 9.99 mmol) was dissolved in tetrahydrofuran (THF) (100 mL), and l-hydroxypyrrolidine-2,5-dione (2.299 g, 19.98 mmol) was then added, followed by the addition of DCC (4.12 g, 19.98 mmol). The mixture was stirred at room temperature for 18 hours until HPLC analysis indicated the completion of the reaction. The solid was removed by filtration through a celite pad, and washed with THF (3 x 2 mL). The combined filtrate was concentrated and purified by flash chromatography to yield bis(2,5-dioxopyrrolidin-l-yl) heptanedioate (ER-001236140) as a white solid (2.5 g, 71% yield). 1HNMR (400 MHz) δ ppm 2.83 (s, 8H), 2.64 (t, J = 7.6 Hz, 4H), 1.80 (dt, J= 7.6 Hz, 4H), 1.59-1.51 (m, 2H). LCMS (M+H)=355.2.
  • 4
  • [ 111-16-0 ]
  • [ 628-76-2 ]
  • [ 4224-62-8 ]
  • 5
  • [ 67-56-1 ]
  • [ 111-16-0 ]
  • [ 1732-08-7 ]
  • [ 20291-40-1 ]
  • 6
  • [ 111-16-0 ]
  • cobalt(II) acetate [ No CAS ]
  • [ 151433-25-9 ]
  • [(1-RR)-(Pimelic acid)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% 1.8 g of (R, R) -N,N'-bis (3, 5-di-t-butylsalicylidene) -1,2- cyclohexanediamine and 1.1 g of cobalt (II) acetate-4H2O were mixed in 35 ml of ethanol and stirred under reflux for 5 hours. They were filtered at room temperature and cleaned by small amount of ethanol. The obtained solid was uniformly divided into four parts and mixed with 6 ml of acetone and 10 ml of dichloromethane respectively. Also, 1.0 equivalent weight of succinic acid, glutaric acid, adipic acid, and pimeric acid were added respectively and stirred for 3 hours with injection of air at room temperature. After the solvent was eliminated under reduced pressure, the title compounds were obtained quantitatively.
  • 7
  • [ 111-16-0 ]
  • [ 4054-67-5 ]
  • [ 7732-18-5 ]
  • [ 20667-12-3 ]
  • [(silver)4(3,3′,5,5′-tetramethyl-4,4′-bipyrazole)7(pimelate)2] *12H2O [ No CAS ]
  • 8
  • [ 111-16-0 ]
  • [ 4054-67-5 ]
  • [(silver)4(3,3′,5,5′-tetramethyl-4,4′-bipyrazole)7(pimelate)2] [ No CAS ]
  • 9
  • [ 111-16-0 ]
  • [ 67-66-3 ]
  • [ 18653-98-0 ]
  • [ 1612840-98-8 ]
YieldReaction ConditionsOperation in experiment
69.8% In methanol; Salt 1 was prepared by mixing L1 (0.27 g, 1.0 mmol) and AA (0.15 g, 1.0 mmol) in an acetonitrile-methanol mixture (v/v%, 1:4, 10 ml).The resulting solution was stirred for 6 h, and filtered through Celite. The filtrate was evaporated until dryness under vacuum, and the white solid obtained was redissolved in methanol. Salt 2 was obtained by the same procedure as outlined above for 1 using PA (0.16 g, 1.0 mmol) in chloroform-methanol mixture (v/v%, 1:4, 10 ml) with 69.8% (0.68 g, 0.69 mmol) yields. Anal. Calcd.(%) for C47H65N4O12Cl3 (984.40): C, 57.34; H, 6.65; N, 5.69; Found:C, 57.07; H, 6.55; N, 5.49. FT-IR (KBr, cm-1): 3643, 3324, 2949,2411, 2269, 2161, 1933, 1697, 1567, 1412, 1354, 1139, 1033,922, 739, 697, 526. 1H NMR (DMSO-d6, ppm) δ: 12.37 (s, br, 4H,NH2), 6.07-6.62 (m, 8H, CH, Ar L1), 3.19 (t, 4H, CH2, aliphatic L1),2.31 (s, 4H, CH2, Benzylic L1), 2.17 (t, 4H, CH2, PA2), 1.55 (m, 4H,CH2, PA2-), 1.29 (m, 2H, CH2, PA2-).
  • 10
  • [ 82410-79-5 ]
  • [ 111-16-0 ]
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [Zn2(1,4-bis(2-methylimidazol-1-methyl)benzene)(pimelate)2]n [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With sodium hydroxide; In water; at 90.0℃; for 96h;pH 7.0;Autoclave; A solution of H2pim (0.2mmol) in 8mL H2O was adjusted to pH 7 with dilute NaOH. Then bix (0.1mmol) and Zn(NO3)2·6H2O (0.2mmol) in 12mL H2O were added. The mixture was added to a 20mL Teflon-lined stainless autoclave and this was sealed and heated to 90C for 4days, then cooled to room temperature to give colorless crystals of 4 in 31% yield (0.022g). Anal. Calc. for C30H38N4O8Zn (4): C, 50.51; H, 5.37; N, 7.85. Found: C, 50.42; H, 5.28; N, 7.67%. IR data (cm-1): 1587m, 1541 s, 1442 w, 1401 m, 1300 w, 1156 w, 1142 w, 1007 w, 794 w, 743 w, 718 w, 667 w, 632 w
  • 11
  • [ 14112-98-2 ]
  • [ 111-16-0 ]
YieldReaction ConditionsOperation in experiment
87% With ethanol; potassium bromide; sodium hydroxide; In dimethyl sulfoxide; at 140℃;pH 7.0; In a 250mL reactor, dissolve 3.12g acetohexanoic acid in 60mL dimethyl sulfoxide, add 140mL ethanol solution containing 1.20mol potassium bromide dropwise at 140C, and then dropwise add NaOH (concentration 2mol/L) The pH of the solution was adjusted to 7, the precipitate was removed by filtration, the pH of the reaction solution was adjusted to 1 with sulfuric acid, the precipitated solid was filtered and dried to obtain pimelic acid with a yield of 87%.
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