107-75-5|7-Hydroxy-3,7-dimethyloctanal| Ambeed

CAS No. :	107-75-5
Formula :	C₁₀H₂₀O₂
M.W :	172.26
SMILES Code :	CC(CCCC(C)(C)O)CC=O
MDL No. :	MFCD00014681
InChI Key :	WPFVBOQKRVRMJB-UHFFFAOYSA-N
Pubchem ID :	7888

Safety of [ 107-75-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317
Precautionary Statements:	P261-P280

Computational Chemistry of [ 107-75-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	0
Fraction Csp3	0.9
Num. rotatable bonds	6
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	51.58
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.31
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.64
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.15
Log P_o/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.	1.77
Log P_o/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	2.29
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.55
Solubility	4.91 mg/ml ; 0.0285 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.	-2.04
Solubility	1.58 mg/ml ; 0.0092 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	-2.13
Solubility	1.29 mg/ml ; 0.00746 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.	-6.19 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)	2.09

Application In Synthesis of [ 107-75-5 ]

* 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.

Downstream synthetic route of [ 107-75-5 ]

[ 107-75-5 ] Synthesis Path-Downstream 1~56

1
[ 2385-77-5 ]
[ 107-75-5 ]

References: [1]Journal of Organic Chemistry,1958,vol. 23,p. 689.

2
[ 107-75-5 ]
[ 18479-57-7 ]

References: [1]Journal of Organic Chemistry,1958,vol. 23,p. 689.

3
[ 68797-68-2 ]
[ 107-75-5 ]

References: [1]Helvetica Chimica Acta,1978,vol. 61,p. 2560 - 2578.

4
[ 67-56-1 ]
[ 123366-53-0 ]
[ 106-23-0 ]
[ 107-75-5 ]
[ 3613-30-7 ]

References: [1]Acta Chimica Hungarica,1985,vol. 119,p. 347 - 354.

5
[ 67-56-1 ]
[ 42822-94-6 ]
[ 106-23-0 ]
[ 107-75-5 ]
[ 3613-30-7 ]

References: [1]Acta Chimica Hungarica,1985,vol. 119,p. 347 - 354.

6
[ 67-56-1 ]
[ 42822-96-8 ]
[ 106-23-0 ]
[ 107-75-5 ]
[ 3613-30-7 ]

References: [1]Acta Chimica Hungarica,1985,vol. 119,p. 347 - 354.

7
[ 98206-63-4 ]
[ 107-75-5 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1991,vol. 40,p. 99 - 105.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1991,p. 115 - 121.

8
[ 107-75-5 ]
[ 98206-63-4 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 1681 - 1684.

9
[ 107-75-5 ]
2-(4-methylcyclohex-1-en-1-yl)prop-2-yl cation [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1990,p. 1275 - 1277.

10
[ 55035-66-0 ]
[ 107-75-5 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1990,vol. 26,p. 219 - 221.
Zhurnal Organicheskoi Khimii,1990,vol. 26,p. 262 - 265.

11
[ 107-75-5 ]
[ 106-49-0 ]
[ 90058-74-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

12
[ 107-75-5 ]
[ 106-47-8 ]
[ 90058-72-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

13
[ 107-75-5 ]
[ 150-13-0 ]
[ 90058-68-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

14
[ 107-75-5 ]
[ 75-03-6 ]
[ 3613-33-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

15
[ 107-75-5 ]
[ 100-01-6 ]
[ 90058-73-4 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

16
[ 107-75-5 ]
[ 62-53-3 ]
[ 90058-71-2 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

17
[ 107-75-5 ]
[ 74-88-4 ]
[ 3613-30-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

18
[ 107-75-5 ]
[ 81290-20-2 ]
9,9,9-Trifluoro-2,6-dimethyl-8-trimethylsilanyloxy-nonan-2-ol [ No CAS ]

References: [1]Journal of Fluorine Chemistry,1995,vol. 73,p. 21 - 26.

19
[ 107-75-5 ]
[ 108-24-7 ]
[ 39839-28-6 ]
Acetic acid 7,7-diacetoxy-1,1,5-trimethyl-heptyl ester [ No CAS ]

References: [1]Journal of Chemical Research - Part S,1998,p. 94 - 95.

Yield	Reaction Conditions	Operation in experiment
86%		EXAMPLE 14 Proceeding in the same manner as in Example 1, except using 7-hydroxyneryldiethylamine in place of the 7-hydroxygeranyldiethylamine used in Example 1, 65 g (yield: 86%) of 7-hydroxycitronellal was obtained.

22
[ 107-75-5 ]
[ 108-24-7 ]
C₁₄H₂₆O₅ [ No CAS ]
Acetic acid 7,7-diacetoxy-1,1,5-trimethyl-heptyl ester [ No CAS ]

References: [1]Synthetic Communications,2008,vol. 38,p. 106 - 113.

23
[ 141-27-5 ]
[ 107-75-5 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1990,vol. 26,p. 219 - 221.
Zhurnal Organicheskoi Khimii,1990,vol. 26,p. 262 - 265.

24
[ 72172-53-3 ]
[ 107-75-5 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1990,vol. 26,p. 219 - 221.
Zhurnal Organicheskoi Khimii,1990,vol. 26,p. 262 - 265.

25
[ 128935-79-5 ]
[ 107-75-5 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1990,vol. 26,p. 219 - 221.
Zhurnal Organicheskoi Khimii,1990,vol. 26,p. 262 - 265.

26
[ 107-75-5 ]
1,1,1-Trifluoro-4,8-dimethyl-nonane-2,8-diol [ No CAS ]

References: [1]Journal of Fluorine Chemistry,1995,vol. 73,p. 21 - 26.

27
[ 107-75-5 ]
[ 90058-69-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

28
[ 107-75-5 ]
[ 90058-70-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

29
[ 107-75-5 ]
[ 67893-08-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

30
[ 107-75-5 ]
[ 90058-75-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

31
[ 107-75-5 ]
[ 90058-76-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

32
[ 107-75-5 ]
[ 90058-79-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

33
[ 107-75-5 ]
[ 90058-77-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

34
[ 107-75-5 ]
[ 90058-78-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 948 - 951.

35
[ 107-75-5 ]
[ 34405-39-5 ]
[ 141-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; toluene-4-sulfonic acid; In methanol;	EXAMPLE 2 The starting material of Example 1 can be prepared as follows: 172.2 g. of hydroxycitronellal and 106.1 g. of orthoformic acid methyl ester are treated dropwise, while cooling with ice, with a solution of 0.5 g. of p-toluenesulphonic acid in 800 ml. of absolute methanol. After 2 hours, 5 g. of sodium acetate are added and the mixture is concentrated on a rotary evaporator at 50C. Upon distillation, the residue yields pure 1,1-dimethoxy-3,7-dimethyl-7-octanol; boiling point = 102C/0.4 mmHg; nD22 = 1.4400.

References: [1]Patent: US3983247,1976,A .

36
[ 50-00-0 ]
[ 107-75-5 ]
[ 22414-67-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dibutylamine; hexanoic acid; In water; at 95℃; for 0.666667h;	EXAMPLE 5A 3 L four-necked flask equipped with a stirrer, a thermometer and a reflux condenser was charged with 1032 g (6.0 mol) of hydroxycitronellal, 520 g (6.4 mol) of a 37% by mass formaldehyde aqueous solution, 53 g (0.41 mol) of dibutyl amine and 10 g (0.09 mol) of hexanoic acid, and the contents in the flask were stirred while heating at 95C. After the elapse of 40 min, it was confirmed that no hydroxycitronellal was present in the raw mixture, and then the mixture was cooled and separated into two layers. The thus separated organic layer was subjected to distillation treatment, thereby obtaining 1058 g (5.5 mol) of 3,7-dimethyl-2-methylene-7-hydroxyoctanal (purity as measured by gas chromatography: 95%) (yield based on theoretical amount: 92%).

References: [1]Patent: WO2007/63703,2007,A1 .Location in patent: Page/Page column 18.

37
[ 107-75-5 ]
copper dichloride [ No CAS ]
Cu(3,7-dimethyl-7-oxyoctan-1-al)2 [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 514 - 515.

38
oxovanadium(IV) sulfate [ No CAS ]
[ 107-75-5 ]
C₂₀H₃₈O₅V [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 848 - 849.

39
[ 107-75-5 ]
cobalt(II) nitrate [ No CAS ]
Co(3,7-dimethyl-7-oxyoctan-1-al)2 [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 514 - 515.

40
uranyl(VI) nitrate [ No CAS ]
[ 107-75-5 ]
UO₂((CH₃)2C₇H₁₂(CHO)O)2 [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 848 - 849.

41
vanadium (IV) oxide sulfate * 6 H₂O [ No CAS ]
[ 107-75-5 ]
VO(3,7-dimethyl-7-oxyoctan-1-al)2*2H₂O [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 514 - 515.

42
bismuth(III) nitrate hexahydrate [ No CAS ]
[ 107-75-5 ]
Bi(3,7-dimethyl-7-oxyoctan-1-al)2NO₃*2H₂O [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 514 - 515.

43
[ 107-75-5 ]
nickel dichloride [ No CAS ]
Ni(3,7-dimethyl-7-oxyoctan-1-al)2 [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 514 - 515.

44
[ 107-75-5 ]
palladium dichloride [ No CAS ]
Pd(3,7-dimethyl-7-oxyoctan-1-al)2 [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 514 - 515.

45
[ 107-75-5 ]
[ 141-82-2 ]
[ 1082301-20-9 ]

References: [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 7346 - 7349.

46
[ 107-75-5 ]
[ 3536-96-7 ]
[ 1217274-22-0 ]

References: [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 967 - 970.

47
[ 107-75-5 ]
[ 623-12-1 ]
[ 72960-20-4 ]

References: [1]Organic Letters,2010,vol. 12,p. 3670 - 3673.

48
[ 107-75-5 ]
[ 4645-32-3 ]
[ 1277172-21-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	In 1,4-dioxane; at 60℃; for 24h;	To a stirring solution of vinyl phosphonate (1 mmol) in 1,4-dioxane (1 mL) was addedaldehyde (5 mmol) and the reaction mixture stirred at 60 C for 24 h unless otherwise stated.The reaction mixture was concentrated in vacuo and the resultant gamma-ketophosphonate purifiedas described below.

References: [1]Tetrahedron Letters,2011,vol. 52,p. 1067 - 1069.
[2]Organic and Biomolecular Chemistry,2013,vol. 11,p. 7301 - 7317.

49
[ 461-72-3 ]
[ 107-75-5 ]
[ 1333480-84-4 ]

References: [1]Chemistry and biodiversity,2011,vol. 8,p. 1470 - 1485.

50
[ 107-75-5 ]
7-hydroxycitronellic acid [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 3656 - 3659.
[2]Organic and Biomolecular Chemistry,2013,vol. 11,p. 7301 - 7317.

51
[ 253-52-1 ]
[ 107-75-5 ]
2-methyl-6-(naphthalen-2-yl)heptan-2-ol [ No CAS ]

References: [1]Synthesis,2012,vol. 44,p. 2195 - 2199.

52
[ 107-75-5 ]
[ 112-62-9 ]
[ 1373279-28-7 ]
[ 1373279-29-8 ]
[ 2566-91-8 ]

Yield	Reaction Conditions	Operation in experiment
13%Chromat.	With 5% Ru/SiO2; oxygen; at 80 - 150℃; for 12h;	Example 1 [0105] This example presents a comparison of various catalysts consisting of a metal deposited on a silicon media. All catalysts were prepared using ionic exchange starting from a colloidal silica stabilized with ammonium ions and metal chloride corresponding to the active species. These items were tested in regards to the functionalization reaction of methyl oleate by hydroxycitronellal which lead to the synthesis of 9-hydroxy-10-(7-hydroxy-3,7-dimethyloctanoyloxy)methyl octadecanoate and of 10-hydroxy-9-(7-hydroxy-3,7-dimethyloctanoyloxy)methyl octadecanoate as illustrated in Diagram 2. [0106] The reaction was carried out in a 100 ml glass reactor with mechanical agitation. Twenty-five grams (25.0 g) of methyl ester of sunflower oil HTO (high oleic content-purity: 85% methyl oleate) as well as 13.0 g of hydroxycitronellal (FCC Grade: Purity?95%-Sigma-Aldrich, Ref. W258318) were introduced into the reactor. The solid catalyst of the metal type supported on silica contains 5% by weight of the quantity of methyl oleate engaged, i.e. 250 mg. The environment was heated to 80 C. with continuous air bubbling. The air flow was controlled by a ball flow meter at 70 ml/min. After 7 hours of reaction time, the air flow was stopped and the reaction medium was raised to 150 C. These parameters were maintained for 5 additional hours. Samples of the reaction medium were taken at regular intervals in order to determine the status of the reaction. The reagent conversion rates and the yield rates of the desired products after 7 and 12 hours of reaction time are shown in Table 1: [TABLE-US-00001] Conversion Function- into alized Conversion hydroxy- Epoxide products Type of Reaction into methyl citronellala yield yield catalyst time (hr.) oleate (%) (%) (%) (%) no catalyst 7 37 70 27 11 12 46 92 9 24 Ru/SiO2 7 75 95 52 24 12 80 100 13 39 Co/SiO2 7 76 100 31 19 12 77 100 16 29 Zn/SiO2 7 66 99 30 20 12 69 100 10 27 Ni/SiO2 7 51 90 34 15 12 59 98 13 25 Cr/SiO2 7 49 89 31 15 12 56 97 13 25 Cu/SiO2 7 34 90 24 16 12 38 97 11 22 Rh/SiO2 7 34 86 18 17 12 40 96 8 26 [0107] The composition of the reaction medium was determined by gas phase chromatographic analysis. The Agilent Technologies 6870N chromatograph is equipped with a capillary column (SGE-BPX-70-length: 30 m, inside diameter: 0.25 mm, film thickness: 0.25 mum), of a split/splitless injector and a flame ionization detector (temperature of the injector and the detector: 280 C.). The temperature program of the furnace was as follows: 80 C. (0 min.)-13 C./min.-180 C. (6 min.)-13 C./min.-220 C. (6 min.)-17 C./min.-250 C. (10 min.). [0108] The hold time for the various products under the conditions described above are as follows: dodecane (2.9 min.); hydroxycitronellal (8.9 min.); methyl oleate (12.6 min.); methyl trans-9,10epoxy-stearate (18.9 min.); methyl cis-9,10-epoxy-stearate (19.2 min). [0109] The conversion of reagents at time t is expressed as follows: (number of initial moles of reagent-number of moles of reagent at time t)/number of initial moles of reagent100. [0110] The epoxide yield at time t was calculated as follows: number of moles of epoxide at time t/(number of initial moles of methyl oleaterelative response coefficient of 9,10-epoxystearate in relation to methyl oleate)*100. [0111] The functionalized products, i.e. the methyl octadecanoate 9-hydroxy-10-(7-hydroxy-3,7-dimethyloctanoyloxy) and the methyl octadecanoate 10-hydroxy-9-(7-hydroxy-3,7-dimethyloctanoyloxy), were analyzed by steric exclusion chromatography. [0112] The Waters Alliance 2695 chromatograph is equipped with a refraction index detector (RI 410) and with two different columns (Styrage-HR 0.5 and Styragel-HR 1). The temperature of the furnace containing the columns is set at 30 C. and tetrahydrofurane (THF) is used as an eluent at a flow rate of 0.8 ml/min. [0113] Under these conditions, the hold times were as follows: products with high molecular weight (>1000 uma; 15.1 min); functionalized products (16.2 min.); methyl oleate and methyl 9,10-epoxy-stearate (18.1 min.); hydroxycitronellal (19.0 min.). [0114] The functionalized products yield is the relative surface area of the chromatographic peak expressed as a percentage of the total of all peaks.
52%Chromat.	With 5% Ru/SiO2; oxygen; at 80℃; for 7h;	Example 1 [0105] This example presents a comparison of various catalysts consisting of a metal deposited on a silicon media. All catalysts were prepared using ionic exchange starting from a colloidal silica stabilized with ammonium ions and metal chloride corresponding to the active species. These items were tested in regards to the functionalization reaction of methyl oleate by hydroxycitronellal which lead to the synthesis of 9-hydroxy-10-(7-hydroxy-3,7-dimethyloctanoyloxy)methyl octadecanoate and of 10-hydroxy-9-(7-hydroxy-3,7-dimethyloctanoyloxy)methyl octadecanoate as illustrated in Diagram 2. [0106] The reaction was carried out in a 100 ml glass reactor with mechanical agitation. Twenty-five grams (25.0 g) of methyl ester of sunflower oil HTO (high oleic content-purity: 85% methyl oleate) as well as 13.0 g of hydroxycitronellal (FCC Grade: Purity?95%-Sigma-Aldrich, Ref. W258318) were introduced into the reactor. The solid catalyst of the metal type supported on silica contains 5% by weight of the quantity of methyl oleate engaged, i.e. 250 mg. The environment was heated to 80 C. with continuous air bubbling. The air flow was controlled by a ball flow meter at 70 ml/min. After 7 hours of reaction time, the air flow was stopped and the reaction medium was raised to 150 C. These parameters were maintained for 5 additional hours. Samples of the reaction medium were taken at regular intervals in order to determine the status of the reaction. The reagent conversion rates and the yield rates of the desired products after 7 and 12 hours of reaction time are shown in Table 1: [TABLE-US-00001] Conversion Function- into alized Conversion hydroxy- Epoxide products Type of Reaction into methyl citronellala yield yield catalyst time (hr.) oleate (%) (%) (%) (%) no catalyst 7 37 70 27 11 12 46 92 9 24 Ru/SiO2 7 75 95 52 24 12 80 100 13 39 Co/SiO2 7 76 100 31 19 12 77 100 16 29 Zn/SiO2 7 66 99 30 20 12 69 100 10 27 Ni/SiO2 7 51 90 34 15 12 59 98 13 25 Cr/SiO2 7 49 89 31 15 12 56 97 13 25 Cu/SiO2 7 34 90 24 16 12 38 97 11 22 Rh/SiO2 7 34 86 18 17 12 40 96 8 26 [0107] The composition of the reaction medium was determined by gas phase chromatographic analysis. The Agilent Technologies 6870N chromatograph is equipped with a capillary column (SGE-BPX-70-length: 30 m, inside diameter: 0.25 mm, film thickness: 0.25 mum), of a split/splitless injector and a flame ionization detector (temperature of the injector and the detector: 280 C.). The temperature program of the furnace was as follows: 80 C. (0 min.)-13 C./min.-180 C. (6 min.)-13 C./min.-220 C. (6 min.)-17 C./min.-250 C. (10 min.). [0108] The hold time for the various products under the conditions described above are as follows: dodecane (2.9 min.); hydroxycitronellal (8.9 min.); methyl oleate (12.6 min.); methyl trans-9,10epoxy-stearate (18.9 min.); methyl cis-9,10-epoxy-stearate (19.2 min). [0109] The conversion of reagents at time t is expressed as follows: (number of initial moles of reagent-number of moles of reagent at time t)/number of initial moles of reagent100. [0110] The epoxide yield at time t was calculated as follows: number of moles of epoxide at time t/(number of initial moles of methyl oleaterelative response coefficient of 9,10-epoxystearate in relation to methyl oleate)*100. [0111] The functionalized products, i.e. the methyl octadecanoate 9-hydroxy-10-(7-hydroxy-3,7-dimethyloctanoyloxy) and the methyl octadecanoate 10-hydroxy-9-(7-hydroxy-3,7-dimethyloctanoyloxy), were analyzed by steric exclusion chromatography. [0112] The Waters Alliance 2695 chromatograph is equipped with a refraction index detector (RI 410) and with two different columns (Styrage-HR 0.5 and Styragel-HR 1). The temperature of the furnace containing the columns is set at 30 C. and tetrahydrofurane (THF) is used as an eluent at a flow rate of 0.8 ml/min. [0113] Under these conditions, the hold times were as follows: products with high molecular weight (>1000 uma; 15.1 min); functionalized products (16.2 min.); methyl oleate and methyl 9,10-epoxy-stearate (18.1 min.); hydroxycitronellal (19.0 min.). [0114] The functionalized products yield is the relative surface area of the chromatographic peak expressed as a percentage of the total of all peaks.

References: [1]Patent: US2013/211033,2013,A1 .Location in patent: Paragraph 0105-0114.
[2]Patent: US2013/211033,2013,A1 .Location in patent: Paragraph 0105-0114.

53
[ 107-75-5 ]
[ 2446-83-5 ]
dipropan-2-yl 1-(7-hydroxy-3,7-dimethyloctanoyl)hydrazine-1,2-dicarboxylate [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 7301 - 7317.

54
[ 107-75-5 ]
[ 452905-58-7 ]
pentafluorophenyl 9-hydroxy-5,9-dimethyl-3-oxodecane-1-sulfonate [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 7301 - 7317.
[2]RSC Advances,2015,vol. 5,p. 44423 - 44426.

55
[ 107-75-5 ]
[ 23055-10-9 ]
2-(9-hydroxy-5,9-dimethyl-3-oxodecan-2-yl)malonic acid diethyl ester [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 7301 - 7317.

56
[ 621-23-8 ]
[ 107-75-5 ]
C₁₉H₃₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		Compounds 46: 7-hyroxycitronellal (140 mu, 0.75 mmol), Cu(OTf)2 (2.2 mg, 2.5 mol %), ethanethiol (108 mu, 1.5 mmol) and 1,3,5- trimethoxybenzene (42 mg, 0.25 mmol) were reacted according to method B. The mixture was stirred for 2 h at rt. After the addition of Et3SiH (116 mu, 0.75 mmol) the reaction was stirred for 1 h at room temperature. The residual material was purified by column chromatography (silica gel 40-60, hexane / ethyl acetate 80:20) affording compound 46 (64 mg, 79% yield) as a thick oil. Characterization data of compound 46: lH NMR (CDCl3/400 MHz): delta 6.13 (s, 2H), 3.80 (s, 3H), 6.79 (s, 6H), 2.60 - 2.48 (m, 2H), 1.49 - 1.24 (m, 9H), 1.21 (s, 6H), 0.93 (d, J = 6.2, Hz, 3H); 13C NMR (CDCl3/100 MHz): 6 159.0, 158.7, 112.3, 90.6, 71.1, 55.7, 55.3, 44.4, 37.3, 36.6, 32.9, 29.3, 29.2, 21.6, 20.1, 19.7; HRMS (ESI): m/z calcd for Ci9H3204 [M+H]+ 325.2373 found 325.2363.

References: [1]Patent: WO2016/132355,2016,A1 .Location in patent: Page/Page column 60.
[2]Organic Letters,2015,vol. 17,p. 2924 - 2927.

Historical Records

Technical Information

• Appel Reaction • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Heat of Combustion • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Stetter Reaction • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 107-75-5 ]

Aliphatic Chain Hydrocarbons

A149671 [58888-76-9]

3-Hydroxy-3-methylhexanoic acid

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A190618 [78-69-3]

3,7-Dimethyloctan-3-ol

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A246884 [625-08-1]

3-Hydroxy-3-methylbutanoic acid

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A329783 [108-82-7]

2,6-Dimethylheptan-4-ol

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A700690 [4221-03-8]

5-Hydroxypentanal

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Aldehydes

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4-Hydroxybicyclo[2.2.2]octane-1-carbaldehyde

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A700690 [4221-03-8]

5-Hydroxypentanal

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A665119 [59-23-4]

(2R,3S,4S,5R)-2,3,4,5,6-Pentahydroxyhexanal

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A688878 [50675-18-8]

Tetrahydropyran-4-carbaldehyde

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A953470 [112-31-2]

Decyl aldehyde

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Alcohols

A475661 [878792-30-4]

4-Hydroxybicyclo[2.2.2]octane-1-carbaldehyde

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A149671 [58888-76-9]

3-Hydroxy-3-methylhexanoic acid

Similarity: 0.78

A166681 [17768-36-4]

2-(3-Hydroxyadamantan-1-yl)acetic acid

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A190618 [78-69-3]

3,7-Dimethyloctan-3-ol

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2-(4-Hydroxycyclohexyl)acetic acid

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