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Chemical Structure| 5435-64-3 Chemical Structure| 5435-64-3

Structure of 5435-64-3

Chemical Structure| 5435-64-3

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Product Details of [ 5435-64-3 ]

CAS No. :5435-64-3
Formula : C9H18O
M.W : 142.24
SMILES Code : CC(C)(C)CC(C)CC=O
MDL No. :MFCD00010441
InChI Key :WTPYRCJDOZVZON-UHFFFAOYSA-N
Pubchem ID :21574

Safety of [ 5435-64-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1989
Packing Group:

Computational Chemistry of [ 5435-64-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 0.89
Num. rotatable bonds 4
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 45.32
TPSA ?

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

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.23
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

2.72
Log Po/w (WLOGP)?

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

2.65
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.

2.39
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

2.39
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.48

Water Solubility

Log S (ESOL):?

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

-2.17
Solubility 0.958 mg/ml ; 0.00674 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-2.73
Solubility 0.264 mg/ml ; 0.00185 mol/l
Class?

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

-2.26
Solubility 0.783 mg/ml ; 0.00551 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.

-5.24 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

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)

1.79

Application In Synthesis of [ 5435-64-3 ]

* 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 [ 5435-64-3 ]

[ 5435-64-3 ] Synthesis Path-Downstream   1~7

  • 2
  • [ 3452-97-9 ]
  • silver contact [ No CAS ]
  • [ 5435-64-3 ]
  • 3
  • [ 590-28-3 ]
  • [ 5435-64-3 ]
  • [ 443-86-7 ]
  • 1.) Wang-resin supported HOOC-(CH2)5-NC [ No CAS ]
  • 6-[1-(3-Fluoro-2-methyl-phenyl)-2-oxo-5-(2,4,4-trimethyl-pentyl)-imidazolidin-(4Z)-ylideneamino]-hexanoic acid [ No CAS ]
  • 4
  • [ 590-28-3 ]
  • [ 5435-64-3 ]
  • [ 443-86-7 ]
  • CN(CH2)4CH2COOCH2-resin [ No CAS ]
  • 6-[1-(3-Fluoro-2-methyl-phenyl)-2-oxo-5-(2,4,4-trimethyl-pentyl)-imidazolidin-(4Z)-ylideneamino]-hexanoic acid [ No CAS ]
  • 5
  • [ 5435-64-3 ]
  • [ 3452-97-9 ]
YieldReaction ConditionsOperation in experiment
74% With formic acid; water; palladium diacetate; tricyclohexylphosphine; In 1,4-dioxane; at 90℃; for 6h;Inert atmosphere; Sealed tube; General procedure: An oven-dried pressure tube containing a Teflon-coated stirring bar was charged with Pd(OAc)2 (11.2 mg, 5 molpercent), PCy3 (21 mg, 7.5 molpercent) and aldehyde(1 mmol).The tube was sealed, evacuated and backfilled with N2. 1 mL of dioxane was subsequently injected. After the mixture was stirred at room temperature for 15 min, H2O (180 mg, 10 equiv) and HCO2H (184 mg, 4 equiv) were injected and the reaction was heated to 90 oC for 18 h. After the reaction was completed, the solvent was removed under vacuo. The residues were purified by flash column chromatography on silica gel to afford 87 mg of benzyl alcohol in 81 percent yield.
With thiophene; hydrogen;Pricat CZ 29/2T; at 300℃; under 150015.0 Torr; for 0 - 264h; A laboratory scale hydrogenation of nonanal, which had been produced by the [HYDROFORMYLATION OF DI-ISOBUTENE,] was carried out using a microreactor containing a [10ML] sample of PRICAT CZ 29/2 (35 wtpercent copper oxide/65 wtpercent zinc oxide) catalyst. Nonanal consists predominantly (about 90percent by weight) of a single isomer, which is 3,5, 5- [TRIMETHYLHEXANAL.] The catalyst was reduced in the micro reactor at atmospheric pressure and [250 °C] in a hydrogen-containing nitrogen stream flowing at 1 I/hr. the concentration of hydrogen in the gas stream was increased from 5percent to 100percent over a period of about 10 hours. The reactor was then brought up to operating pressure (200 barg) using neat hydrogen. The reactor was then operated at 300 [°C] at a gas: oil ratio of 7923: 1, using the nonanal feed at a liquid feed rate of 15-20 [ML/HOUR] to show the performance of the catalyst before treatment with the sulphur compound. The gas: oil ratio is the hydrogen flow rate [(RM3/HR,] i. e. measured at [20 °C] and 1 atmosphere) divided by the liquid feed rate (m3/hr). 0.2 ml of thiophene was then added to the feed vessel contents (1.9 litres) and the reactor was run continuously under the same conditions until the feed had been consumed (7 days). Subsequently the reactor was run using aldehyde feed containing no thiophene. The feed and product streams were analysed using temperature-programmed capillary gas chromatography. Table 1 shows the concentration of the major components in the feed stream and in the product stream over the course of the reaction. The abbreviations used in the table are: 244 tmp: 2,4, 4-trimethyl pentane 224 tmh: 2,2, 4-trimethyl hexane aldehyde: 3,5, [5-TRIMETHYLHEXANAL] alcohol : 3,5, 5-trimethylhexanol heavies: heavy end products including dimer (C18) ester, dimer alcohol, dimer ether, trimers and other high boiling by products. Table 1 Day 244tmp 224tmh Aldehyde Alcohol Heavies (Feed) 2. 4 0. 1 85. 4 8. 5 0. 58 0 3. 3 16. 2 0. 1 75. 9 4. 66 1 3. 6 9. 1 0. 1 81. 7 7. 25 2 3. 2 2. 7 0. 2 89. 8 6. 91 3 3. 4 1. 8 0. 4 89. 8 6. 85 4 3. 0 1. 7 0. 4 90. 2 7. 07 5 2. 6 2. 3 0. 3 90. 1 7. 5 6 2. 9 2. 6 0. 3 89. 9 6. 92 7 2. 5 2. 6 0. 3 90. 1 7. 21 8 2. 7 2. 7 0. 3 89. 9 7 9 2. 2 2. 3 0. 3 92. 3 4. 38 10 2. 7 2. 5 0. 3 91. 8 3. 78 11 2. 9 2. 7 0. 3 90. 3 5. 03 There is very little unhydroformylated olefin in the crude aldehyde product used in this example. The concentration of 2,4, 4-trimethyl pentane, which would be the product of hydrogenating di-isobutene is relatively low and constant. However, the concentration of 2,2, 4-trimethyl hexane, which is at a very low level in the feed rises to over 16percent when the hydrogenation takes place over un-treated catalyst. 2,2, 4-trimethyl hexane is present as a product of the hydrogenolysis of the product alcohol. It is very noticeable that during and after treatment with thiophene, the concentration of 2,2, 4-trimethyl hexane falls to about 2.5percent with a corresponding increase in the concentration of desired product alcohol in the product stream.
With hydrogen;Cu/Cr/Ni catalyst; at 180℃; under 18751.9 Torr; Example 3 Preparation of 3,5,5-trimethylhexyl Benzoate (Comparative Example) 1000 g of 2,4,4-trimethyl-1-pentene (diisobutene) from Oxeno (may be prepared as in DE 10106593.0, for example) were hydroformylated in a 2 l autoclave at 135° C. under 270 bar of synthesis gas pressure for 3 hours in the presence of an unmodified rhodium catalyst.The active catalyst was generated in situ from rhodium nonanoate (24.8percent by weight of Rh).rhodium concentration based on diisobutene was set at 20 ppm. After 3 hours the reaction was terminated and the autoclave was cooled to 20° C. The reaction discharge comprises 93.5percent by weight of 3,5,5-trimethylhexanal, 2.5percent by weight of 3,5,5-trimethylhexanol, 3.4percent by weight of residual C8 hydrocarbons, and 0.6percent by weight of high-boilers. The reaction discharge was freed from rhodium catalyst by distillation on a laboratory distillation column. The Rh-free hydroformylation discharge was then hydrogenated in the liquid phase in a fixed-bed reactor in the presence of a Cu/Cr/Ni catalyst at 180° C. and 25 bar. After hydrogenation of 3,5,5-trimethylhexanal to give the target product 3,5,5-trimethylhexanol, the hydrogenation discharge was freed from low-boilers (C8 hydrocarbons) by controlled distillation. [0071] The distillation process gave a 3,5,5-trimethylhexanol of purity above 99.5percent by weight.
  • 6
  • [ 107-39-1 ]
  • synthesis gas [ No CAS ]
  • [ 3452-97-9 ]
  • [ 5435-64-3 ]
YieldReaction ConditionsOperation in experiment
rhodium nonanoate; at 135℃; under 202520.0 Torr; for 3h; Example 3 Preparation of 3,5,5-trimethylhexyl Benzoate (Comparative Example) 1000 g of 2,4,4-trimethyl-1-pentene (diisobutene) from Oxeno (may be prepared as in DE 10106593.0, for example) were hydroformylated in a 2 l autoclave at 135° C. under 270 bar of synthesis gas pressure for 3 hours in the presence of an unmodified rhodium catalyst.The active catalyst was generated in situ from rhodium nonanoate (24.8percent by weight of Rh).rhodium concentration based on diisobutene was set at 20 ppm. After 3 hours the reaction was terminated and the autoclave was cooled to 20° C. The reaction discharge comprises 93.5percent by weight of 3,5,5-trimethylhexanal, 2.5percent by weight of 3,5,5-trimethylhexanol, 3.4percent by weight of residual C8 hydrocarbons, and 0.6percent by weight of high-boilers. The reaction discharge was freed from rhodium catalyst by distillation on a laboratory distillation column.
  • 7
  • [ 107-39-1 ]
  • [ 201230-82-2 ]
  • [ 3452-97-9 ]
  • [ 5435-64-3 ]
 

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