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Chemical Structure| 1873-88-7 Chemical Structure| 1873-88-7
Chemical Structure| 1873-88-7

1,1,1,3,5,5,5-Heptamethyltrisiloxane

CAS No.: 1873-88-7

4.5 *For Research Use Only !

Cat. No.: A913309 Purity: 98%

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Product Details of [ 1873-88-7 ]

CAS No. :1873-88-7
Formula : C7H22O2Si3
M.W : 222.50
SMILES Code : C[Si](C)(C)O[SiH](C)O[Si](C)(C)C
MDL No. :MFCD00048000
InChI Key :SWGZAKPJNWCPRY-UHFFFAOYSA-N
Pubchem ID :6327366

Safety of [ 1873-88-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P210-P302+P352-P305+P351+P338
Class:3
UN#:1993
Packing Group:

Calculated chemistry of [ 1873-88-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 61.87
TPSA ?

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

18.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.57
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

3.45
Log Po/w (WLOGP)?

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

2.54
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.

0.96
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

-2.54
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.6

Water Solubility

Log S (ESOL):?

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

-3.13
Solubility 0.165 mg/ml ; 0.000743 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.

-3.52
Solubility 0.0674 mg/ml ; 0.000303 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

-2.39
Solubility 0.904 mg/ml ; 0.00406 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.

-5.21 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

0.0
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)

4.28

Application In Synthesis of [ 1873-88-7 ]

* 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 [ 1873-88-7 ]

[ 1873-88-7 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 75-54-7 ]
  • [ 75-77-4 ]
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  • [ 16066-09-4 ]
  • [ 2370-88-9 ]
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  • [ 6166-86-5 ]
  • [ 17998-54-8 ]
  • 2
  • [ 75-54-7 ]
  • [ 75-77-4 ]
  • [ 1873-88-7 ]
  • [ 16066-09-4 ]
  • [ 2370-88-9 ]
  • [ 6166-86-5 ]
  • 3
  • [ 75-54-7 ]
  • [ 110-54-3 ]
  • [ 107-46-0 ]
  • ice [ No CAS ]
  • [ 1873-88-7 ]
  • [ 16066-09-4 ]
  • [ 17478-13-6 ]
  • [ 17998-54-8 ]
  • 4
  • [ 106-86-5 ]
  • [ 1873-88-7 ]
  • 3-(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)-1,1,1,3,5,5,5-heptamethyltrisiloxane [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With dihydrogen hexachloroplatinate; at 75 - 85℃; for 2h; Into a 500 mL round bottom flask equipped with a temperature controller, heating mantel, and condenser 3-ethenyl-7-oxabicyclo[4.I.Ojheptane (57.8 grams, 0.47 mole) was added. The solution was stirred with a magnetic stirrer and heated to 75C. Chloroplatinic acid (20 ppm) was added followed by the slow addition of 1,1,1,3,5,5,5- heptmethyltrisiloxane (100 g, 0.45 mol) via an addition fbnnel. The exotherm was not allowed to go above 85C. After the addition the reaction was held at 75C for 2 hours.resulting product was distilled through a 6 inch Vigreux column under a 0.9 torr vacuum. The product, 3-[bis-(trimethylsiloxy)methylsi lanyl-ethyl}-7- oxabicyclo[4.l.0]heptane, evolved between 110 and 120 C. The pure product (151.1 grams, 96% yield) was a clear colorless fluid.
96% With dihydrogen hexachloroplatinate; at 75 - 85℃; Into a 500 mL round bottom flask equipped with a temperature controller, heating mantel, and condenser 3- ethenyl-7-oxabicyclo [ 4.1.0 ] heptane (57.8 grams, 0.47 mole) was added. The solution was stirred with a magnetic stirrer and heated to 75C. Chloroplatinic acid (20 ppm) was added followed by the slow addition of 1,1,1,3,5,5,5- heptmethyltrisiloxane (100 g, 0.45 mole) via an addition funnel. The exotherm was not allowed to go above 85C. After the addition the reaction was held at 75C for 2 hours. The resulting product was distilled through a 6 inch Vigreux column under a 0.9 torr vacuum. The product, 3- [bis- ( trimethylsiloxy) methylsilanyl-ethyl ] -7- oxabicyclo [ 4.1.0 ] eptane, evolved between 110 and 120 C . The pure product (151.1 grams, 96% yield) was a clear colorless fluid .
96% With dihydrogen hexachloroplatinate; at 75 - 85℃; for 2h; Temperature controller, 500 ml round bottom flask 3-ethenyl-7-oxabicyclo[4.1.0]heptane(57.8 g, 0.47 mole) with a heating mantle and condenser were added. The solution is stirred with a magnetic stirrer, it was heated to 75 . It is added chloroplatinic acid (20 ppm), 1,1,1,3,5,5,5-heptamethyltrisiloxane(100 grams, 0.45 moles) after the was added slowly by addition funnel. Exotherm was not exceed 85 C.. After the addition, the reaction was carried out for 2 hours at 75 C.. Resulting product was distilled through a Vigreux column 15.24 cm (6 inches) under a vacuum of 0.9 Torr. Is the product 3-[bis(trimethylsiloxy)methylsilanylethyl]-7-oxabicyclo[4.1.0]heptane was released between 110 ~ 120 . Pure product (151.1 g, 96% yield) was a clear, colorless liquid.
94% C13H28N2OPtSi2; In xylene; at 70℃; for 4h;Product distribution / selectivity; Preparation of Preparation of silane compound by hydrosilylation of (CH 3 ) 3 Si-O-Si(CH 3 )(H)-OSi(CH 3 ) 3 and 3-vinyl-7-oxabicyclo[4.1.0]heptane (/) ) A catalyst described in Table 1 (15 ppm (6.4×10-7 mol) of platinum included in the catalyst) was dissolved in xylene and added to a 25 mL 2-necked round-bottom flask equipped with a nitrogen gas inlet tube and a cooling tube. After adding (CH3)3Si-O-Si(CH3)(H)-OSi(CH3)3 (5.38 g, 24.2 mmol) and dodecane (0.38 g, 2.2 mmol) as internal standard, the mixture was heated to 70 ºC while stirring. Then, 3-vinyl-7-oxabicyclo[4.1.0]heptane ( , 3.00 g, 24.2 mmol) was added thereto dropwisely at a rate of 1 mL/min using a syringe. Thereafter, the progress of reaction was monitored by gas chromatography.The hydrosilylation reaction of Preparation Example 7 was performed according to Scheme 10. Reaction condition and yield of the produced silane compound are given in Table 8.[Scheme 10]Used catalyst amount (ppm) Reaction condition Remaining 3-vinyl-7-oxabicyclo[4.1.0]heptane (%) Yield (%) Temp. (ºC) Time (hr) Comp. Ex. 1 15 70 4 - 92 Ex. 1 15 4 - 94 3-vinyl-7-oxabicyclo[4.1.0]heptane (/) ) A catalyst described in Table 1 (15 ppm (6.4×10-7 mol) of platinum included in the catalyst) was dissolved in xylene and added to a 25 mL 2-necked round-bottom flask equipped with a nitrogen gas inlet tube and a cooling tube. After adding (CH3)3Si-O-Si(CH3)(H)-OSi(CH3)3 (5.38 g, 24.2 mmol) and dodecane (0.38 g, 2.2 mmol) as internal standard, the mixture was heated to 70 ºC while stirring. Then, 3-vinyl-7-oxabicyclo[4.1.0]heptane ( , 3.00 g, 24.2 mmol) was added thereto dropwisely at a rate of 1 mL/min using a syringe. Thereafter, the progress of reaction was monitored by gas chromatography.The hydrosilylation reaction of Preparation Example 7 was performed according to Scheme 10. Reaction condition and yield of the produced silane compound are given in Table 8.[Scheme 10]Used catalyst amount (ppm) Reaction condition Remaining 3-vinyl-7-oxabicyclo[4.1.0]heptane (%) Yield (%) Temp. (ºC) Time (hr) Comp. Ex. 1 15 70 4 - 92 Ex. 1 15 4 - 94
C13H28N2OPtSi2; In dodecane; xylene; at 70℃; for 4h;Inert atmosphere;Product distribution / selectivity; A catalyst described in Table 1 (15 ppm (6.4×10-7 mol) of platinum included in the catalyst) was dissolved in xylene and added to a 25 mL 2-necked round-bottom flask equipped with a nitrogen gas inlet tube and a cooling tube. After adding (CH3)3Si-O-Si(CH3)(H)-OSi(CH3)3 (5.38 g, 24.2 mmol) and dodecane (0.38 g, 2.2 mmol) as internal standard, the mixture was heated to 70 C. while stirring. Then, 3-vinyl-7-oxabicyclo[4.1.0]heptane 3.00 g, 24.2 mmol) was added thereto dropwisely at a rate of 1 mL/min using a syringe. Thereafter, the progress of reaction was monitored by gas chromatography.The hydrosilylation reaction of Preparation Example 7 was performed according to Scheme 10. Reaction condition and yield of the produced silane compound are given in Table 8.

YieldReaction ConditionsOperation in experiment
hexahydro-2H-oxepin-2-one; Karstedt platinum catalyst; at 70℃;Conversion of starting material; 21.48 g (173 mmol) of VCMX and the organic compound (see table 1 below) are charged to a 100 ml reactor. [0095] The reaction mixture is heated to 70 C. with stirring. 5.5 mul (10 ppm) of a solution of Karstedt catalyst containing 10% of platinum are added to the reactor and 35 g (157.3 mmol) of heptamethyl-hydrotrisiloxane are subsequently run in dropwise onto the VCMX. [0096] At the end of the addition, the degree of conversion of the SiH units is measured.
  • 6
  • [ 75-54-7 ]
  • [ 107-46-0 ]
  • [ 1873-88-7 ]
  • [ 16066-09-4 ]
  • [ 17478-13-6 ]
  • [ 17998-54-8 ]
  • 7
  • [ 106-86-5 ]
  • [ 1873-88-7 ]
  • poly(1,2-epoxy-4-vinylcyclohexane-co-heptamethylhydrotrisiloxane) [ No CAS ]
YieldReaction ConditionsOperation in experiment
C19H35N2OPtSi2; In toluene; at 70℃; for 10h; 21.48 g (173 mmol) of 4-vinylcyclohexene oxide (VCMX) are placed in a 100 ml reactor. The reaction mixture is heated to 70 C. with agitation. 20 mul (10 ppm) of a solution of the catalytic metal complex (XXI) at 2.68% for platinum in toluene are added to the reactor and 35 g (157.3 mmol) of heptamethylhydrotrisiloxane are then poured dropwise, over 3 hours, onto the VCMX. [0247] After reaction for 5 hours, the degree of transformation of the SiH units is 99.5%, and 0.5% of the epoxide functions have disappeared. After reaction for 7 hours, the degree of transformation of the SiH units is 99.8%, and 1% of the epoxide functions have disappeared. The viscosity of the reaction crude at 25 C. is measured: v=6 mPa/s.
Karstedt platinum catalyst; In toluene; at 70℃; for 10h; 21.48 g (173 mmol) of 4-vinylcyclohexene oxide (VCMX) are placed in a 100 ml reactor. The reaction mixture is heated at 70 C. with agitation. 5.5 mul (10 ppm) of a solution of Karstedt catalyst at 10% for platinum are added to the reactor and 35 g (157.3 mmol) of heptamethylhydrosiloxane are then poured dropwise, over 3 hours, onto the VCMX. [0250] After reaction for 5 hours, the degree of transformation of the SiH units is 99%, but 12% of the epoxide functions have disappeared. After reaction for 7 hours, the degree of transformation of the SiH units is 99.3%, and 23% of the epoxide functions have disappeared. The viscosity of the reaction crude at 25 C. is measured: v=38 mPa/s. [0251] The viscosity value for the oil of example 3 is 6 times higher than that of example 2, which means that some of the epoxide functions present in the medium have polymerized during the hydrosilylation reaction in the presence of the Karstedt catalyst.
  • 9
  • [ 1721-26-2 ]
  • [ 1873-88-7 ]
  • C16H31NO4Si3 [ No CAS ]
  • 10
  • [ 106-86-5 ]
  • [ 1873-88-7 ]
  • (2-methylacryloylamino)acetic acid 2-hydroxy-5-[2-(bis(trimethylsiloxy)(methyl)silanyl)ethyl]cyclohexyl ester [ No CAS ]
  • 11
  • [ 1873-88-7 ]
  • [ 88229-16-7 ]
  • C17H32FNO3Si3 [ No CAS ]
  • 12
  • [ 1034287-04-1 ]
  • [ 1873-88-7 ]
  • (E)-1,1,1,3,5,5,5-heptamethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl]trisiloxane [ No CAS ]
  • C21H39BO4Si3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; In toluene; at 100℃; for 24h;Green chemistry; General procedure: A silane and an appropriate alkyne were placed in a 25cm3 round bottom flask equipped with a stirrer and a glass stopper. The reagents were dissolved in toluene or THF and Karstedt?s catalyst was added. Subsequently, the reaction mixture was heated to 60C or 100C, depending on the reaction. Samples of the reaction mixture were collected in intervals, and the conversion of SiH was determined by 1H NMR and GC-MS. Then the reactions were repeated in determined reaction time, and the resulting mixtures were isolated by the evaporation of the solvent under vacuum. Products were characterized by 1H, 13C, 29Si NMR, GC-MS analysis. The platinum residue was removed by filtration of petroleum ether solution through silica gel. After evaporation of solvents, the products were dried for 6h under vacuum. Isolated products were characterized by 1H, 13C, 29Si NMR, GC-MS. For new compounds, elemental analysis was performed as well.
  • 13
  • [ 1873-88-7 ]
  • [ 100342-30-1 ]
  • C15H33NO4S2Si3 [ No CAS ]
  • 14
  • [ 1873-88-7 ]
  • [ 214360-70-0 ]
  • C17H35BO4SSi3 [ No CAS ]
  • 15
  • [ 59418-09-6 ]
  • [ 1873-88-7 ]
  • C12H25NO4SSi3 [ No CAS ]
  • 16
  • [ 1873-88-7 ]
  • [ 29949-85-7 ]
  • (5-chloro-2-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)phenyl)bis(3-chlorophenyl)phosphane [ No CAS ]
  • 17
  • [ 1873-88-7 ]
  • [ 607-01-2 ]
  • ethyl(2-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)phenyl)(phenyl)phosphane [ No CAS ]
 

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