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Chemical Structure| 69610-41-9 Chemical Structure| 69610-41-9

Structure of Boc-L-prolinal
CAS No.: 69610-41-9

Chemical Structure| 69610-41-9

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Product Details of [ 69610-41-9 ]

CAS No. :69610-41-9
Formula : C10H17NO3
M.W : 199.25
SMILES Code : O=C[C@H]1N(C(OC(C)(C)C)=O)CCC1
MDL No. :MFCD00274186
InChI Key :YDBPZCVWPFMBDH-QMMMGPOBSA-N
Pubchem ID :2734674

Safety of [ 69610-41-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P362-P403+P233-P405-P501

Computational Chemistry of [ 69610-41-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 0
Fraction Csp3 0.8
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 56.79
TPSA ?

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

46.61 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.38
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

1.16
Log Po/w (WLOGP)?

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

1.2
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.

0.76
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

0.95
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.29

Water Solubility

Log S (ESOL):?

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

-1.54
Solubility 5.72 mg/ml ; 0.0287 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.

-1.73
Solubility 3.68 mg/ml ; 0.0185 mol/l
Class?

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

Very 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

-0.95
Solubility 22.5 mg/ml ; 0.113 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

Yes
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.

-6.69 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

1.0
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

1.0 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)

2.42

Application In Synthesis of [ 69610-41-9 ]

* 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 [ 69610-41-9 ]

[ 69610-41-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 124755-24-4 ]
  • [ 69610-41-9 ]
  • [ 104700-41-6 ]
  • [ 356788-89-1 ]
  • 2
  • [ 30094-28-1 ]
  • [ 69610-41-9 ]
  • [ 61275-22-7 ]
  • [ 873302-79-5 ]
  • [ 873302-78-4 ]
  • 3
  • [ 6216-63-3 ]
  • [ 69610-40-8 ]
  • [ 69610-41-9 ]
YieldReaction ConditionsOperation in experiment
Example 87A (S)-N-Boc-2-Formyl-pyrrolidine STR115 (S)-N-Boc-2-Formyl-pyrrolidine was prepared by Swern oxidation of (S)-N-Boc prolinol (Fluka) according to the conditions described by M. G. B. Drew et al., J. Chem. Soc. Perkin 1, 1998, 1627, for the oxidation of CBZ-prolinol.
  • 4
  • [ 69610-41-9 ]
  • [ 228244-04-0 ]
  • 5
  • [ 69610-41-9 ]
  • [ 745017-94-1 ]
  • 6
  • C18H12F6O8S2 [ No CAS ]
  • [ 69610-41-9 ]
  • [ 1007882-23-6 ]
YieldReaction ConditionsOperation in experiment
90% With ammonium acetate; In dimethyl sulfoxide; at 60℃; for 2h; The compound DSV102 (2.63g) and dimethyl sulfoxide (30ml) were added to a 50ml three-necked flask, and reacted at 30 C for 31 hours.Ammonium acetate (2.31 g), L-Boc guanaldehyde (1.99 g), and reacted at 60 C for 2 h. Add 30ml of anhydrous methanol dropwise, stir at 25 CAt night (14h), suction filtration, solid washing with water (20ml * 3), drying at 80 C under vacuum, to obtain 2.81g solid DSV01, yield 90%,The purity is 96%.
  • 7
  • [ 4072-67-7 ]
  • [ 69610-41-9 ]
  • [ 1007882-23-6 ]
YieldReaction ConditionsOperation in experiment
85% With ammonium acetate; In dimethyl sulfoxide; at 30℃; for 4h; Add to a 100ml two-neck bottleBrominated biphenyl diacetyl(1.98g),Dimethyl sulfoxide (20ml),The reaction was carried out at 25 C for 16 h, and ammonium acetate (2.31 g) was added.L-Boc-prolinal(1.99 g), reacted at 30 C for 4 h.Add 20 ml of anhydrous methanol, 20 ml of water, and stir for 45 min.Filter by suction, wash the solid with water (20ml * 3), vacuum dry at 80 C,Obtained 2.66 g of solid DSV01,The yield is 85%,The purity is 94%.
  • 8
  • [ 24860-53-5 ]
  • [ 69610-41-9 ]
  • [ 1007882-23-6 ]
YieldReaction ConditionsOperation in experiment
82% Add DSV101 (1.54g) to a 50ml three-necked flask,Potassium bromide (0.30 g), dimethyl sulfoxide (10 ml),After reacting at 75 C for 6 h, the temperature was lowered, and ammonium acetate (2.31 g) was added.L-Boc guanylaldehyde (1.99 g) was reacted at 40 C for 5 h. Add 100ml of water,The organic layer was washed with brine (100 ml)Separation by column chromatography2.56g solid DSV01,The yield is 82%.The purity is 95%
 

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