[ CAS No. 111969-64-3 ] {[proInfo.proName]}

Name: 111969-64-3|(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 2,2-dihydroxyacetate|98%
Brand: Ambeed
SKU: A857378
Price: 9.0 USD
Availability: InStock
Rating: 94 (32 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

2D 3D

Structure of 111969-64-3 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 111969-64-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 111969-64-3 ]

SDS Specification

Alternatived Products of [ 111969-64-3 ]

Product Details of [ 111969-64-3 ]

CAS No. :	111969-64-3	MDL No. :	MFCD00154508
Formula :	C₁₂H₂₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BWZMJRSMHQDFIT-KXUCPTDWSA-N
M.W :	230.30	Pubchem ID :	7373179
Synonyms :

Calculated chemistry of [ 111969-64-3 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.92
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	61.29
TPSA :	66.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	2.79
Log Po/w (WLOGP) :	1.3
Log Po/w (MLOGP) :	1.44
Log Po/w (SILICOS-IT) :	1.13
Consensus Log Po/w :	1.77

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.76
Solubility :	0.399 mg/ml ; 0.00173 mol/l
Class :	Soluble
Log S (Ali) :	-3.85
Solubility :	0.0327 mg/ml ; 0.000142 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.66
Solubility :	50.3 mg/ml ; 0.218 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.31

Safety of [ 111969-64-3 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P273-P260-P280-P391-P314-P305+P351+P338+P310	UN#:	3077
Hazard Statements:	H318-H373-H411	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 111969-64-3 ]

* 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.

Upstream synthesis route of [ 111969-64-3 ]
Downstream synthetic route of [ 111969-64-3 ]

[ 111969-64-3 ] Synthesis Path-Upstream 1~8

1
[ 81529-62-6 ]
[ 111969-64-3 ]

Reference： [1] Synthesis, 1998, # 11, p. 1590 - 1592

2
[ 2216-51-5 ]
[ 111969-64-3 ]

Reference： [1] Patent: CN105130806, 2017, B,
[2] Patent: CN107382725, 2017, A,

3
[ 81529-62-6 ]
[ 26315-61-7 ]
[ 111969-64-3 ]

Reference： [1] Synthesis, 1998, # 11, p. 1590 - 1592

4
[ 26315-61-7 ]
[ 111969-64-3 ]

Reference： [1] Patent: CN105130806, 2017, B,

5
[ 2216-51-5 ]
[ 111969-64-3 ]

Reference： [1] Patent: CN105130806, 2017, B,

6
[ 40018-26-6 ]
[ 111969-64-3 ]
[ 147126-62-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With acetic acid In acetone at 50 - 125℃;	L-Menthyl glyoxalate monohydrate (1.0 g, 4.34 mmol) in acetone (10 mL), was added to 1,4-dithiane 2,5-diol (396 mg, 2.60 mmol) and a catalytic amount of acetic acid (0.5 mL). The solutions were pumped at a flow rate 0.05 mL/min (for a combined flow rate of 0.1 mL/min, and the reaction solution was passed through a flow reactor at 125°C, and exited the flow system through a back pressure regulator (lObar) to control the temperature and pressure. The reaction mixture was collected into a collection vial equipped with a septum. After completion of the reaction, as monitored by thin layer chromatography (“TLC”) and gas chromatography (“GC”), the solvent was evaporated. The reaction mixture was cooled to 0°C - 5°C and a 1percent triethylamine in heptane or hexane solution was added drop wise. The mixture was stirred at 0°C for 2 — 3 hours, observing the formation of precipitation. The isolated solid was filtered and washed with n-hexane to give (2R,5R)-((1 R, 2S,5R)-2-isopropyl-5- methylcyclohexyl) 5-hydroxy-1, 3-oxathiolane-2-carboxylate (1.1 g, 88percent) as a white solid. Spectral Analysis:IH-NMR in CDCI3 (400 MHz): a 5.96 (ci, IH), 5.57 (d, IH), 4.74 (s, IH), 3.32-3.29 (m, IH), 3.17-3.08 (dd, IH), 2.02 (d, 2H), 1.70 (d, 1H), 1.51 -1 .42 (m, 2H),1.09-1.00 (m, 21-I), 0.91(d, 61-1), 0.78 (d, 3H). 13C-NMR in CDCI3 (100 MHz): B16.27, 20.69, 23.30, 26.16, 31.42, 34.11, 38.46, 40.35, 46.86, 46.07, 80.20,101.22, 103.20, 172.18. FT-IR (Neat): 3456, 2956, 2864, 1731, 1457, 1387,1288, 1196, 1041, 986.Nature of the compound: white solidFlow rate: 0.1 mLlminResidence Time: 20 mmReaction temperature: 50 °C to 125 °CRecrystallization: 1percent in TEA in heptane/hexaneConfirmed by: GC, IR and 1H-NMR spectra
100 g	With acetic acid In toluene at 50 - 115℃;	L-menthyl glyoxylate hydrate (prepared by reaction of L-menthol with glyoxalic acid as per process described in Synthetic Commun., 1990, 20, 2837-2847 by Fernadez F.) (100 gm, 0.434 mol, 1 molar equivalents), toluene (500 ml) and acetic acid (10 ml) were mixed under stirring and thus formed reaction mixture was heated up to 1 10- 1 15°C, to remove water azeotropically. The reaction mixture was cooled up to 80°C and solvent was distilled under vacuum up to the final volume becomes 300 ml. The reaction mixture was cooled to 50°C and 1 ,4-Dithiane 2,5-Diol (33.1 gm, 0.217 mol, 2 molar equivalents) was added. The reaction mixture was refluxed (110- 115°C) and monitored the reaction by TLC. The mixture was cooled to 0-5°C after completion of the reaction. 600 ml of 10percent triethylamine in n-heptane was added to the reaction mixture drop wise over a period of an hour. The mixture was then maintained at 0-5°C for an hour to form a solid. The isolated solid was filtered, washed with n-heptane and dried. Yield: 100 g. Ή NMR (DMSO-d6 + D₂0) δ (ppm): 0.70-0.91 (m, 10H); 0.95- 1.05 (q, 2H), 1.35- 1.46 (q, 2H), 1.62- 1.64 (d, 2H), 1.84- 1.90 (t, 2H), 2.86-2.88 (d, 1H), 3.12-3.16 (q, 1H), 4.59-4.64 (m, 1H), 5.55-5.60 (t, 1H), 5.86 (s, 1H), 7.03-7.04 (d, 1H); i3C NMR (DMSO-d6) 8 (ppm): 21 , 22.2, 23.3, 26, 31.2, 34, 37.8, 38, 40.1 , 46.7, 75, 76.4, 102.4, 169.5; IR (KBr) (cm-'): 3470, 2962, 29.34, 28.366, 1734, 1465, 1 198, 1077, 1041, 902, 516; MS (EI) m/z = 287.3 (M- l).

Reference： [1] Patent: WO2017/216709, 2017, A2, . Location in patent: Page/Page column 12; 13; 14; 15; 17; 18
[2] Tetrahedron Letters, 2005, vol. 46, # 49, p. 8535 - 8538
[3] Patent: WO2013/21290, 2013, A1, . Location in patent: Page/Page column 17; 18

7
[ 111969-64-3 ]
[ 764659-72-5 ]

Reference： [1] Patent: WO2013/21290, 2013, A1,
[2] Organic Letters, 2015, vol. 17, # 11, p. 2626 - 2629
[3] Organic Letters, 2015, vol. 17, # 11, p. 2626 - 2629

8
[ 111969-64-3 ]
[ 147126-65-6 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 11, p. 2626 - 2629

[ 111969-64-3 ] Synthesis Path-Downstream 1~43

1
[ 19293-62-0 ]
[ 111969-64-3 ]
[ 91538-20-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1931 - 1938

2
[ 111969-64-3 ]
[ 622-30-0 ]
[ 85252-42-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

3
[ 7677-24-9 ]
[ 111969-64-3 ]
Cyano-hydroxy-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester [ No CAS ]

Reference： [1]Synlett,1997,p. 1379 - 1380

4
[ 81529-62-6 ]
[ 26315-61-7 ]
[ 111969-64-3 ]

Reference： [1]Synthesis,1998,p. 1590 - 1592

5
[ 81529-62-6 ]
[ 111969-64-3 ]

Reference： [1]Synthesis,1998,p. 1590 - 1592

6
[ 111969-64-3 ]
[ 26315-61-7 ]

Reference： [1]Synthesis,1998,p. 1590 - 1592

7
[ 111969-64-3 ]
[ 762-72-1 ]
2-Hydroxy-pent-4-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester [ No CAS ]

Reference： [1]Heteroatom Chemistry,2001,vol. 12,p. 534 - 538

8
[ 40018-26-6 ]
[ 111969-64-3 ]
[ 147126-62-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With acetic acid; In acetone; at 50 - 125℃;	L-Menthyl glyoxalate monohydrate (1.0 g, 4.34 mmol) in acetone (10 mL), was added to 1,4-dithiane 2,5-diol (396 mg, 2.60 mmol) and a catalytic amount of acetic acid (0.5 mL). The solutions were pumped at a flow rate 0.05 mL/min (for a combined flow rate of 0.1 mL/min, and the reaction solution was passed through a flow reactor at 125C, and exited the flow system through a back pressure regulator (lObar) to control the temperature and pressure. The reaction mixture was collected into a collection vial equipped with a septum. After completion of the reaction, as monitored by thin layer chromatography (?TLC?) and gas chromatography (?GC?), the solvent was evaporated. The reaction mixture was cooled to 0C - 5C and a 1% triethylamine in heptane or hexane solution was added drop wise. The mixture was stirred at 0C for 2 - 3 hours, observing the formation of precipitation. The isolated solid was filtered and washed with n-hexane to give (2R,5R)-((1 R, 2S,5R)-2-isopropyl-5- methylcyclohexyl) 5-hydroxy-1, 3-oxathiolane-2-carboxylate (1.1 g, 88%) as a white solid. Spectral Analysis:IH-NMR in CDCI3 (400 MHz): a 5.96 (ci, IH), 5.57 (d, IH), 4.74 (s, IH), 3.32-3.29 (m, IH), 3.17-3.08 (dd, IH), 2.02 (d, 2H), 1.70 (d, 1H), 1.51 -1 .42 (m, 2H),1.09-1.00 (m, 21-I), 0.91(d, 61-1), 0.78 (d, 3H). 13C-NMR in CDCI3 (100 MHz): B16.27, 20.69, 23.30, 26.16, 31.42, 34.11, 38.46, 40.35, 46.86, 46.07, 80.20,101.22, 103.20, 172.18. FT-IR (Neat): 3456, 2956, 2864, 1731, 1457, 1387,1288, 1196, 1041, 986.Nature of the compound: white solidFlow rate: 0.1 mLlminResidence Time: 20 mmReaction temperature: 50 C to 125 CRecrystallization: 1% in TEA in heptane/hexaneConfirmed by: GC, IR and 1H-NMR spectra
100 g	With acetic acid; In toluene; at 50 - 115℃;	L-menthyl glyoxylate hydrate (prepared by reaction of L-menthol with glyoxalic acid as per process described in Synthetic Commun., 1990, 20, 2837-2847 by Fernadez F.) (100 gm, 0.434 mol, 1 molar equivalents), toluene (500 ml) and acetic acid (10 ml) were mixed under stirring and thus formed reaction mixture was heated up to 1 10- 1 15C, to remove water azeotropically. The reaction mixture was cooled up to 80C and solvent was distilled under vacuum up to the final volume becomes 300 ml. The reaction mixture was cooled to 50C and 1 ,4-Dithiane 2,5-Diol (33.1 gm, 0.217 mol, 2 molar equivalents) was added. The reaction mixture was refluxed (110- 115C) and monitored the reaction by TLC. The mixture was cooled to 0-5C after completion of the reaction. 600 ml of 10% triethylamine in n-heptane was added to the reaction mixture drop wise over a period of an hour. The mixture was then maintained at 0-5C for an hour to form a solid. The isolated solid was filtered, washed with n-heptane and dried. Yield: 100 g. ? NMR (DMSO-d6 + D20) delta (ppm): 0.70-0.91 (m, 10H); 0.95- 1.05 (q, 2H), 1.35- 1.46 (q, 2H), 1.62- 1.64 (d, 2H), 1.84- 1.90 (t, 2H), 2.86-2.88 (d, 1H), 3.12-3.16 (q, 1H), 4.59-4.64 (m, 1H), 5.55-5.60 (t, 1H), 5.86 (s, 1H), 7.03-7.04 (d, 1H); i3C NMR (DMSO-d6) 8 (ppm): 21 , 22.2, 23.3, 26, 31.2, 34, 37.8, 38, 40.1 , 46.7, 75, 76.4, 102.4, 169.5; IR (KBr) (cm-'): 3470, 2962, 29.34, 28.366, 1734, 1465, 1 198, 1077, 1041, 902, 516; MS (EI) m/z = 287.3 (M- l).

Reference： [1]Patent: WO2017/216709,2017,A2 .Location in patent: Page/Page column 12; 13; 14; 15; 17; 18
[2]Tetrahedron Letters,2005,vol. 46,p. 8535 - 8538
[3]Patent: WO2013/21290,2013,A1 .Location in patent: Page/Page column 17; 18

9
[ 111969-64-3 ]
[ 147027-10-9 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 8535 - 8538
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3444 - 3454
[3]Patent: WO2017/216709,2017,A2

10
[ 111969-64-3 ]
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 8535 - 8538

11
[ 111969-64-3 ]
[ 288325-76-8 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 8535 - 8538

12
[ 2216-51-5 ]
l-α.α'-diphenyl-succinic acid [ No CAS ]
[ 111969-64-3 ]

Reference： [1]Synthesis,1998,p. 1590 - 1592
[2]Synthesis,1998,p. 1590 - 1592

13
[ 111969-64-3 ]
[ 115831-80-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

14
[ 111969-64-3 ]
(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

15
[ 111969-64-3 ]
[ 111969-66-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

16
[ 111969-64-3 ]
[ 111969-66-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

17
[ 111969-64-3 ]
(2S,3S)-2-Amino-3-((R)-1-hydroxy-ethyl)-succinic acid 1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

18
[ 111969-64-3 ]
(2R,3S)-2-Amino-3-((R)-1-hydroxy-ethyl)-succinic acid 1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

19
[ 111969-64-3 ]
[ 111969-67-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

20
[ 111969-64-3 ]
[ 111969-67-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

21
[ 111969-64-3 ]
[ 115936-61-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

22
[ 111969-64-3 ]
[ 111969-65-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

23
[ 111969-64-3 ]
[ 111969-65-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

24
[ 111969-64-3 ]
[ 86207-20-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1931 - 1938

25
[ 111969-64-3 ]
[ 98759-26-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1931 - 1938

26
[ 40018-26-6 ]
[ 111969-64-3 ]
[ 200396-19-6 ]

Yield	Reaction Conditions	Operation in experiment
100%		To a 1.0-lit 4-necked RB flask, charged 500 ml of Toluene, L-Menthyl Glyoxylate (100 gm) followed by acetic acid (10 ml). Heated the reaction mixture upto 110-1 15C, to remove water by azeotrope. After removal of water cooled the R.M., recovered the R.M. under vacuum up to 300 ml solvents remains in the flak Cooled the R.M. Charged 1 ,4-Dithiane 2,5- Diol (33.1 gm) and heated the reaction mixture. Maintained the R.M. by TLC monitoring. After completion of the reaction cooled the mass and concentrate the mass at 50-55C and degassed it to get Hydroxy compound Lami-1 (120-125 gm).

Reference： [1]Patent: WO2011/141805,2011,A2 .Location in patent: Page/Page column 14; 17
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3444 - 3454
[3]Organic process research and development,2020,vol. 24,p. 387 - 397
[4]Organic Letters,2015,vol. 17,p. 2626 - 2629

27
[ 111969-64-3 ]
[ 1346921-53-6 ]

Reference： [1]Patent: WO2011/141805,2011,A2

28
[ 111969-64-3 ]
[ 1346921-70-7 ]

Reference： [1]Patent: WO2011/141805,2011,A2

29
[ 111969-64-3 ]
[ 764659-72-5 ]

Reference： [1]Patent: WO2013/21290,2013,A1
[2]Organic Letters,2015,vol. 17,p. 2626 - 2629
[3]Organic Letters,2015,vol. 17,p. 2626 - 2629

30
[ 111969-64-3 ]
[ 147027-09-6 ]

Reference： [1]Patent: WO2013/21290,2013,A1
[2]Organic Letters,2015,vol. 17,p. 2626 - 2629
[3]Organic Letters,2015,vol. 17,p. 2626 - 2629
[4]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3444 - 3454
[5]Patent: WO2017/216709,2017,A2

31
[ 111969-64-3 ]
[ 147126-65-6 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2626 - 2629

32
[ 111969-64-3 ]
[ 147027-10-9 ]
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2626 - 2629
[2]Organic Letters,2015,vol. 17,p. 2626 - 2629

33
[ 111969-64-3 ]
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2626 - 2629
[2]Organic Letters,2015,vol. 17,p. 2626 - 2629

34
[ 111969-64-3 ]
[ 147126-78-1 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2626 - 2629
[2]Organic Letters,2015,vol. 17,p. 2626 - 2629

35
[ 111969-64-3 ]
C₂₅H₃₃N₃O₄S [ No CAS ]
C₂₅H₃₃N₃O₄S [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2626 - 2629
[2]Organic Letters,2015,vol. 17,p. 2626 - 2629

36
[ 111969-64-3 ]
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[5-fluoro-2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2626 - 2629
[2]Organic Letters,2015,vol. 17,p. 2626 - 2629

37
[ 111969-64-3 ]
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3444 - 3454

38
[ 2216-51-5 ]
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2,2-bis(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2,2-bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)acetate [ No CAS ]
[ 111969-64-3 ]

Reference： [1]Patent: CN105130806,2017,B

39
[ 2216-51-5 ]
[ 111969-64-3 ]

Reference： [1]Patent: CN105130806,2017,B
[2]Patent: CN107382725,2017,A

40
[ 26315-61-7 ]
[ 111969-64-3 ]

Reference： [1]Patent: CN105130806,2017,B

41
C₁₂H₂₁O₆S^(1-)*Na⁽¹⁺⁾ [ No CAS ]
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2,2-bis(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2,2-bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)acetate [ No CAS ]
[ 111969-64-3 ]

Yield	Reaction Conditions	Operation in experiment
10%; 70%	With formaldehyd; water; In cyclohexane; at 20℃; for 16h;pH 6.7 - 7.7;	General procedure: Add 10 ml in a 1000ml bottle,Adding 87.28 50% glyoxylic acid (0.591] 101) and 58 concentrated sulfuric acid,The temperature was refluxed, and 220 g of a cyclohexane solution (L-menthol 120 g (0.77 mol) and cyclohexane 100 g) was slowly added thereto, and the mixture was refluxed for about 5 hours. Nitrogen protection to reduce the temperature, adding 30ml cyclohexane and 60ml water, stirring 10 minutes, standing stratification. The organic phase was washed once with 60 g of water and 50 ml of saturated aqueous NaCl, and the organic phase was collected and allowed to stand.Add 150 g of NaHSO3 aqueous solution (0.60 mol of NaHSO3) to a 2000 ml bottle, stir the temperature to 25-30 C, add the previous organic phase, adjust rhoH- = 4.5-5.5 with saturated Na2C03, keep the temperature at 60 C and pH 8 hours, static stratification.The aqueous phase was washed once with 100 g of cyclohexane and washed once with 60 g of cyclohexane. The aqueous phase was collected and allowed to stand. The organic phase was concentrated, and the solid was precipitated by methanol (about 5%). The NMR was detected as an impurity (compound III, Figure 1, carbon nuclear magnetic spectrum shown in Figure 2 and the spectrum shown in Figure 3).The water phase temperature of 25 C, with saturated Na2C03 adjusted rhoH- = 6.7, stirring drop 60.0 g 40% formaldehyde solution, and then use sulfuric acid aqueous solution as soon as possible to adjust the pH 7.2, the oil precipitation, add a small amount of seed, temperature 25 C to maintain rhoEta = 7.3-7.7 stirring for 4 hours, filter, filter cake washed with water, crude product wet goods.long for the MGH crude product by adding 1.2 times the crude weight of cyclohexane, heated to 45 C stirring 30min, slowly cooled to 10 C for 3 hours, filter, vacuum drying, that is, MGH refined products, Yield 86%.

Reference： [1]Patent: CN105130806,2017,B .Location in patent: Paragraph 0014-0017; 0038-0043; 0059-0060

42
C₁₂H₂₁O₆S^(1-)*Na⁽¹⁺⁾ [ No CAS ]
[ 111969-64-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With formaldehyd; water; In cyclohexane; at 25℃; for 4h;pH 6.7 - 7.7;	General procedure: Add 10 ml in a 1000ml bottle,Adding 87.28 50% glyoxylic acid (0.591] 101) and 58 concentrated sulfuric acid,The temperature was refluxed, and 220 g of a cyclohexane solution (L-menthol 120 g (0.77 mol) and cyclohexane 100 g) was slowly added thereto, and the mixture was refluxed for about 5 hours. Nitrogen protection to reduce the temperature, adding 30ml cyclohexane and 60ml water, stirring 10 minutes, standing stratification. The organic phase was washed once with 60 g of water and 50 ml of saturated aqueous NaCl, and the organic phase was collected and allowed to stand.Add 150 g of NaHSO3 aqueous solution (0.60 mol of NaHSO3) to a 2000 ml bottle, stir the temperature to 25-30 C, add the previous organic phase, adjust rhoH- = 4.5-5.5 with saturated Na2C03, keep the temperature at 60 C and pH 8 hours, static stratification.The aqueous phase was washed once with 100 g of cyclohexane and washed once with 60 g of cyclohexane. The aqueous phase was collected and allowed to stand. The organic phase was concentrated, and the solid was precipitated by methanol (about 5%). The NMR was detected as an impurity (compound III, Figure 1, carbon nuclear magnetic spectrum shown in Figure 2 and the spectrum shown in Figure 3).The water phase temperature of 25 C, with saturated Na2C03 adjusted rhoH- = 6.7, stirring drop 60.0 g 40% formaldehyde solution, and then use sulfuric acid aqueous solution as soon as possible to adjust the pH 7.2, the oil precipitation, add a small amount of seed, temperature 25 C to maintain rhoEta = 7.3-7.7 stirring for 4 hours, filter, filter cake washed with water, crude product wet goods.long for the MGH crude product by adding 1.2 times the crude weight of cyclohexane, heated to 45 C stirring 30min, slowly cooled to 10 C for 3 hours, filter, vacuum drying, that is, MGH refined products, Yield 86%.

Reference： [1]Patent: CN105130806,2017,B .Location in patent: Paragraph 0014-0017; 0038-0043

43
C₁₂H₂₁O₆S^(1-)*Na⁽¹⁺⁾ [ No CAS ]
[ 111969-64-3 ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd; water; sodium carbonate; at 20℃; for 0.5h;	In a 10L esterification reactor with stirring and heating device, Followed by adding 32% menthol cyclohexane solution 7.5kg, 50% glyoxylic acid solution 0.9kg, concentrated sulfuric acid 12.0g, stirring, heated to reflux, And incubated for 4 hours. The above menthol cyclohexane solution was 30.0 mL/min, Glyoxylic acid and concentrated sulfuric acid mixture of 3.8mL/min The flow rate is continuously sent to the continuous esterification reactor for reaction by a peristaltic pump. The reaction system was controlled to reflux, the reaction temperature was 79-80 . The esterification solution continuously overflowing from the esterification tank is evenly delivered to the washing tank through a pump. At the same time, tap water was delivered to the washing vessel at a flow rate of 2.0 mL/min. Continuous overflow to the layered tank for two-phase separation, the organic phase flows out from above, The aqueous phase flows out from the lower part. The above organic phase was fed uniformly into the addition reaction vessel 1 at a flow rate of 37.0 mL / min, At the same time, take a 15% aqueous solution of sodium bisulfite 34.0mL / min metering fed to the addition reactor 1; The 10% sodium carbonate solution is sent to the addition reactor 1 The pH of the control system was 4.7-5.4, and the temperature of the reaction system was 50C. The reaction mixture continuously enters the addition reaction kettle 2 by means of overflowing, After the addition reaction vessel 2 overflows to the addition reaction vessel 3 for reaction, the addition reaction vessel 2 3 at the same time into the aqueous solution of sodium carbonate by peristaltic pump, The control system pH value 4.7-5.4, each pot reaction residence time is 1.5 hours. The reaction mixture overflows from the addition reactor 3 to a layered tank for two-phase separation. The organic phase is recycled and applied. The aqueous phase is continuously extracted with cyclohexane to obtain the aqueous phase of the adduct, The stratified organic phase recovered menthol. Extract the washed aqueous phase with a uniform flow rate of 41.7mL / min into the water analysis kettle 1, By peristaltic pump was added sodium carbonate aqueous solution (flow 0.5mL / min) to adjust the pH value, The system is controlled at 6.4-7.2. Using a metering pump to treat 37% of formaldehyde 2.7mL / min flow into the water analysis kettle 1, stirring at room temperature, the residence time of about 30 minutes. The reaction material is transported from the water analysis kettle 1 to the water analysis kettle 2 with a flow rate of 50.33 mL / min by a peristaltic pump, and the reaction residence time is about 1 hour; after the water reaction kettle 2 reaction materials are uniformly sent to the water analysis kettle 3, the reaction residence time is about 1 hour. The solid-liquid separation is performed after the crystallization is completed. Solid beating refining, cyclohexane as a solvent, Feed ratio of about 0.8 solid weight, drying the product 285.1 g / h (based on the esterification reaction feed), the product yield was 60.5% GC detection purity of 99.8%.

Reference： [1]Patent: CN107382725,2017,A .Location in patent: Paragraph 0066; 0072

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 111969-64-3 ]

Aliphatic Cyclic Hydrocarbons

[ 77-54-3 ]

(3R,3aS,6R,7R,8aS)-3,6,8,8-Tetramethyloctahydro-1H-3a,7-methanoazulen-6-yl acetate

Similarity: 0.73

[ 77341-67-4 ]

4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid

Similarity: 0.73

[ 15840-96-7 ]

Cyclohexyl cyclohexanecarboxylate

Similarity: 0.71

[ 1127-01-1 ]

Ethyl 1-hydroxycyclohexanecarboxylate

Similarity: 0.71

[ 17159-80-7 ]

Ethyl 4-hydroxycyclohexanecarboxylate

Similarity: 0.68

Alcohols

[ 1127-01-1 ]

Ethyl 1-hydroxycyclohexanecarboxylate

Similarity: 0.71

[ 3618-04-0 ]

trans-Ethyl 4-hydroxycyclohexanecarboxylate

Similarity: 0.68

[ 17159-80-7 ]

Ethyl 4-hydroxycyclohexanecarboxylate

Similarity: 0.68

[ 41248-23-1 ]

Ethyl 1-hydroxycyclopentanecarboxylate

Similarity: 0.67

[ 25265-77-4 ]

2,2,4-Trimethyl-1,3-pentanediol 1-monoisobutyrate

Similarity: 0.67

Esters

[ 77-54-3 ]

(3R,3aS,6R,7R,8aS)-3,6,8,8-Tetramethyloctahydro-1H-3a,7-methanoazulen-6-yl acetate

Similarity: 0.73

[ 77341-67-4 ]

4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid

Similarity: 0.73

[ 15840-96-7 ]

Cyclohexyl cyclohexanecarboxylate

Similarity: 0.71

[ 4430-31-3 ]

Octahydro-2H-chromen-2-one

Similarity: 0.71

[ 1127-01-1 ]

Ethyl 1-hydroxycyclohexanecarboxylate

Similarity: 0.71

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 111969-64-3 ] {[proInfo.proName]}

Quality Control of [ 111969-64-3 ]

Related Doc. of [ 111969-64-3 ]

Product Details of [ 111969-64-3 ]

Calculated chemistry of [ 111969-64-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 111969-64-3 ]

Application In Synthesis of [ 111969-64-3 ]

[ 111969-64-3 ] Synthesis Path-Upstream 1~8

[ 111969-64-3 ] Synthesis Path-Downstream 1~43

Related Functional Groups of [ 111969-64-3 ]

Aliphatic Cyclic Hydrocarbons

Alcohols

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 111969-64-3 ]