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Chemical Structure| 108-30-5 Chemical Structure| 108-30-5

Structure of Succinic anhydride
CAS No.: 108-30-5

Chemical Structure| 108-30-5

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Synonyms: Succinyl Oxide; SA

4.5 *For Research Use Only !

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Product Details of [ 108-30-5 ]

CAS No. :108-30-5
Formula : C4H4O3
M.W : 100.07
SMILES Code : O=C(CC1)OC1=O
Synonyms :
Succinyl Oxide; SA
MDL No. :MFCD00005525
InChI Key :RINCXYDBBGOEEQ-UHFFFAOYSA-N
Pubchem ID :7922

Safety of [ 108-30-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314-H317-H334
Precautionary Statements:P501-P272-P260-P270-P264-P280-P284-P342+P311-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 108-30-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 0
Fraction Csp3 0.5
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 20.71
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.62
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.46
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.15
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.08
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.07
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.2

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.17
Solubility 67.6 mg/ml ; 0.675 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

0.02
Solubility 104.0 mg/ml ; 1.04 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.43
Solubility 37.4 mg/ml ; 0.373 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.24 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.06

Application In Synthesis of [ 108-30-5 ]

* 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 [ 108-30-5 ]
  • Downstream synthetic route of [ 108-30-5 ]

[ 108-30-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 1003-09-4 ]
  • [ 108-30-5 ]
  • [ 52240-28-5 ]
References: [1] Journal of Organic Chemistry, 2001, vol. 66, # 22, p. 7283 - 7286.
[2] Organic Syntheses, 2002, vol. 79, p. 204 - 204.
[3] Journal of the Chemical Society, 1954, p. 4162,4165.
[4] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 1083,1103.
[5] Nippon Kagaku Zasshi, 1957, vol. 78, p. 779,783[6] Chem.Abstr., 1960, p. 22559.
  • 2
  • [ 1003-09-4 ]
  • [ 108-30-5 ]
  • [ 80885-88-7 ]
  • [ 52240-28-5 ]
References: [1] Patent: US4299769, 1981, A, .
  • 3
  • [ 108-30-5 ]
  • [ 1165952-91-9 ]
  • [ 6708-37-8 ]
References: [1] Australian Journal of Chemistry, 1981, vol. 34, # 8, p. 1719 - 1727.
  • 4
  • [ 108-30-5 ]
  • [ 57-14-7 ]
  • [ 1596-84-5 ]
References: [1] Journal of Organic Chemistry, 1973, vol. 38, p. 2058 - 2061.
  • 5
  • [ 108-30-5 ]
  • [ 2216-69-5 ]
  • [ 3562-99-0 ]
YieldReaction ConditionsOperation in experiment
86.4% With aluminum (III) chloride In dichloromethane at 33 - 37℃; for 6 h; 15.8 g of 1-methoxynaphthalene and 10.0 g of succinic anhydride were dissolved in 120 mL of dichloromethane,Stir,Cooling to 1 ~ 3 ° C,Divided into three batches of anhydrous aluminum trichloride 15.0 grams,The addition process takes about 20 minutes,The solution was then heated to 35 ± 2 ° C,Insulation reaction 6 hours (5.5 ~ 6.5 hours range),After the reaction is complete,The reaction solution was poured into an ice-water mixture (200 g of ice and 300 g of water) for 30 minutes,Standing, analysiscrystal,Filter,The filtrate was heated and distilled to recover dichloromethane,The cake is the crude of the ketone ketone;And then the crude ketoprofen water as a solvent by 2-3 times recrystallization,Activated carbon decolorization,Demon ketone boutique.The mass of the present product of the chamballone was 22.3 g,Melting point of 176 ~ 179 ° C,The yield was 86.4percent.
References: [1] Patent: CN104370734, 2016, B, . Location in patent: Paragraph 0016-0018.
[2] Helvetica Chimica Acta, 1932, vol. 15, p. 907,914.
[3] Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1936, vol. 5/2, p. 73,75.
[4] Journal of the American Chemical Society, 1940, vol. 62, p. 2750,2752.
[5] Journal of the American Chemical Society, 1951, vol. 73, p. 897,899.
[6] Journal of the American Chemical Society, 1951, vol. 73, p. 326,327.
[7] Kogyo Kagaku Zasshi, 1953, vol. 56, p. 887,889[8] Chem.Abstr., 1955, p. 6904.
[9] Journal of the American Chemical Society, 1936, vol. 58, p. 2314,2316.
[10] Bulletin de la Societe Chimique de France, 1968, p. 627 - 631.
[11] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 285.
  • 6
  • [ 108-30-5 ]
  • [ 75-15-0 ]
  • [ 7446-70-0 ]
  • [ 2216-69-5 ]
  • [ 3562-99-0 ]
References: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 2314,2316.
[2] Helvetica Chimica Acta, 1932, vol. 15, p. 907,914.
[3] Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1936, vol. 5/2, p. 73,75.
  • 7
  • [ 108-30-5 ]
  • [ 7446-70-0 ]
  • [ 630-20-6 ]
  • [ 2216-69-5 ]
  • [ 3562-99-0 ]
References: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 2314,2316.
[2] Helvetica Chimica Acta, 1932, vol. 15, p. 907,914.
[3] Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1936, vol. 5/2, p. 73,75.
  • 8
  • [ 108-30-5 ]
  • [ 7446-70-0 ]
  • [ 98-95-3 ]
  • [ 2216-69-5 ]
  • [ 3562-99-0 ]
References: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 2314,2316.
[2] Helvetica Chimica Acta, 1932, vol. 15, p. 907,914.
[3] Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1936, vol. 5/2, p. 73,75.
 

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