[ CAS No. 127-41-3 ] {[proInfo.proName]}

Name: 127-41-3|(E)-4-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-3-en-2-one|90%
Brand: Ambeed
SKU: A108482
Price: 9.0 USD
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3d Animation Molecule Structure of 127-41-3

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Quality Control of [ 127-41-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 127-41-3 ]

SDS Specification

Alternatived Products of [ 127-41-3 ]

Product Details of [ 127-41-3 ]

CAS No. :	127-41-3	MDL No. :	MFCD00001565
Formula :	C₁₃H₂₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UZFLPKAIBPNNCA-BQYQJAHWSA-N
M.W :	192.30	Pubchem ID :	5282108
Synonyms :

Calculated chemistry of [ 127-41-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.62
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.48
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.81
Log Po/w (XLOGP3) :	3.85
Log Po/w (WLOGP) :	3.51
Log Po/w (MLOGP) :	2.94
Log Po/w (SILICOS-IT) :	3.41
Consensus Log Po/w :	3.31

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.33
Solubility :	0.0908 mg/ml ; 0.000472 mol/l
Class :	Soluble
Log S (Ali) :	-3.9
Solubility :	0.0239 mg/ml ; 0.000125 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.65
Solubility :	0.433 mg/ml ; 0.00225 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.53

Safety of [ 127-41-3 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P201-P273-P301+P312+P330-P308+P313-P391-P501	UN#:	3082
Hazard Statements:	H302-H350-H411	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 127-41-3 ]

* 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 [ 127-41-3 ]
Downstream synthetic route of [ 127-41-3 ]

[ 127-41-3 ] Synthesis Path-Upstream 1~1

1
[ 127-41-3 ]
[ 30364-38-6 ]

Reference： [1] Synthetic Communications, 1990, vol. 20, # 12, p. 1853 - 1856

[ 127-41-3 ] Synthesis Path-Downstream 1~29

1
[ 127-41-3 ]
[ 37384-69-3 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With sodium hypochlorite; In ethanol; at 0 - 20℃; for 12h;	To a solution of a-ionone (10 mL, 48.52 mmol) in EtOH (110 mL)was added NaClO solution (220 mL, 13%) in portions at 0 C. Thereaction mixture was stirred at room temperature for 12 h. Whenthe reaction was completed, the mixture was acidified to pH 1with concentrated HCl. The reaction mixture was extracted withCH2Cl2 (150 mL), washed with water (50 mL), then washed with brine (50 mL) and dried over MgSO4. The solvent was evaporatedunder reduced pressure to give the crude product, which was purifiedthrough flash column chromatography (PE/EA 10/1 0.3%HAc) to afford racemic 1 (8.68 g, 92.1%).To a solution of (±)-1 (47.30 g, 243.47 mmol) in EtOAc (254 mL)was added (R)-(+)-1-phenethylamine (29.51 g, 243.47 mmol) inportions at 50 C. The reaction mixturewas refluxed for 10 min. Thesolution was allowed to cool and crystallization occurred within36 h at 4 C. The precipitated was collected using suction filtrationand washed three times with cold EtOAc (10 mL). This salt (36.99 g)was dissolved in hot EtOAc and recrystallized three times at 4 C.The chiral resolution salt was then dissolved in 200 mL of CH2Cl2,and adjusted to pH 2 with conc. HCl. The organic layers werecollected and dried by MgSO4, and the solvent was removed invacuo to afford the desired product 1a. The procedure describedabove (using the same quantities of (S)-(-)-1-phenethylamine andsolvent) was also followed to yield the enantiopure 1b.
70%	With bromine; sodium hydroxide; In 1,4-dioxane; water; at 20℃; for 4h;	General procedure: 3.0 ml of Br2 was added to a cooled solution (0 C) of NaOH (9.4 g, 0.23 mol) in water (39 ml) and the reaction mixture was allowed to stir 1 h at room temperature. A solution of a or b-ionone (2.5 g, 0.01 mol) in dioxane (5.5 ml) was added dropwise and the solution was further stirred for 4 h. The hypobromite in excess was destroyed with 10% aqueous sodium bisulphite and the solution was extracted with diethyl ether to remove any impurities. Acidification of the alkaline solution with concentrated hydrochloric acid gave 1b as a white solid or 1a as oil.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 245 - 253
[2]Cancer Chemotherapy and Pharmacology,2017,vol. 79,p. 725 - 736
[3]Helvetica Chimica Acta,1954,vol. 37,p. 1798,1802
[4]Helvetica Chimica Acta,1973,vol. 56,p. 2492 - 2508
[5]Helvetica Chimica Acta,1986,vol. 69,p. 1378 - 1394

2
[ 127-41-3 ]
[ 13720-37-1 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 7103 - 7106
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1936,vol. 203,p. 1376
[3]Tetrahedron,1991,vol. 47,p. 7227 - 7236
[4]Bulletin of the Chemical Society of Japan,1982,vol. 55,p. 1329 - 1330
[5]Angewandte Chemie - International Edition,2020,vol. 59,p. 7591 - 7597
Angew. Chem.,2020,vol. 132,p. 7661 - 7667,7

3
[ 127-41-3 ]
[ 31499-72-6 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3601 - 3610
[2]Organic Letters,2008,vol. 10,p. 289 - 292
[3]Tetrahedron Letters,1987,vol. 28,p. 2507 - 2510
[4]Synlett,1999,p. 1663 - 1666
[5]Chemical Communications,2008,p. 4309 - 4311
[6]Angewandte Chemie - International Edition,2020,vol. 59,p. 7591 - 7597
    Angew. Chem.,2020,vol. 132,p. 7661 - 7667,7
[7]Synthetic Communications,1980,vol. 10,p. 899 - 904
[8]Journal of Organic Chemistry,1994,vol. 59,p. 3500 - 3502
[9]Tetrahedron,1986,vol. 42,p. 4603 - 4610
[10]Bulletin de la Societe Chimique de France,1995,vol. 132,p. 243 - 248
[11]Tetrahedron Letters,1990,vol. 31,p. 59 - 62
[12]Synlett,2006,p. 3017 - 3020
[13]Helvetica Chimica Acta,1934,vol. 17,p. 633,639
[14]Helvetica Chimica Acta,1943,vol. 26,p. 2151,2159
    Helvetica Chimica Acta,1949,vol. 32,p. 605
[15]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1936,vol. 203,p. 1376
[16]Helvetica Chimica Acta,1950,vol. 33,p. 1129,1135
    Helvetica Chimica Acta,1952,vol. 35,p. 1637,1647
[17]Bulletin des Societes Chimiques Belges,1995,vol. 104,p. 439 - 448
[18]Chemistry Letters,1982,p. 1625 - 1628
[19]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 1125 - 1132
[20]Journal of Organic Chemistry,1992,vol. 57,p. 955 - 960
[21]Bulletin des Societes Chimiques Belges,1995,vol. 104,p. 439 - 448
[22]Tetrahedron Letters,1996,vol. 37,p. 3529 - 3532
[23]Helvetica Chimica Acta,1955,vol. 38,p. 1338,1339

4
[ 127-41-3 ]
[ 79734-43-3 ]

Yield	Reaction Conditions	Operation in experiment
64%		Freshly distilled (rac)-<strong>[127-41-3]alpha-ionone</strong> (20.00 g, 104.0 mmol) was transferred into a 500 mL three-necked flask using EtOAc (103 mL, 92.08 g, 1.05 mol). K2CO3 (1.44 g, 10.42 mmol) was added and the mixture was cooled down in an ice-salt bath to 0 C. under N2. A 70% solution of TBHP in water (89 mL, 80.1 g 70%?56.07 g, 0.622 mol) was added dropwise to the mixture under N2 at 0 C. in 30 min. Household bleach containing 5.25% NaOCl (295 g, 15.49 g NaOCl, 0.208 mol) was then added over a period of 5 h at -5 to 0 C. After the addition was completed, the reaction mixture was stirred at 0 C. for an additional hour. The organic layer was removed and the water layer was washed with EtOAc (2×100 mL). The combined organic layer was washed with water (2×150 mL), dried over Na2SO4, and evaporated to give 26.8 g of a yellow oil. The crude product was purified by column chromatography (hexane:acetone, from 98:2 to 92:8) to yield (rac)-3-keto-<strong>[127-41-3]alpha-ionone</strong> (13.70 g, 66.41 mmol, 64%).

Reference： [1]Synthesis,2013,vol. 45,p. 615 - 620
[2]Synlett,2006,p. 2617 - 2620
[3]Patent: US2009/264681,2009,A1 .Location in patent: Page/Page column 6-7; 20
[4]Helvetica Chimica Acta,1982,vol. 65,p. 944 - 957
[5]Journal of Agricultural and Food Chemistry,1999,vol. 47,p. 313 - 317
[6]Helvetica Chimica Acta,1952,vol. 35,p. 986,988
[7]Acta Chemica Scandinavica (1947),1973,vol. 27,p. 2107 - 2114
[8]Helvetica Chimica Acta,1981,vol. 64,p. 1092 - 1097
[9]Agricultural and Biological Chemistry,1985,vol. 49,p. 2887 - 2892
[10]Journal of Agricultural and Food Chemistry,1995,vol. 43,p. 185 - 188
[11]Photochemistry and Photobiology,1999,vol. 70,p. 111 - 115
[12]Molecules,2019,vol. 24
[13]Journal of Agricultural and Food Chemistry,2020,vol. 68,p. 5375 - 5383

5
[ 141-10-6 ]
[ 79-77-6 ]
[ 127-41-3 ]

Yield	Reaction Conditions	Operation in experiment
88.2 - 89.8%; 0.8 - 3.8%	With sulfuric acid; water; In dichloromethane; at -20 - 5℃; for 0.916667h;Product distribution / selectivity;	Example 1 In a 1.3L flask with cooling jacket equipped with a stirrer, thermometer, cooler and 2 dropping funnels, 240 grams of 95 wt-% sulfuric acid, and 400 grams methylene chloride are added. The resultant pale-yellow emulsion is cooled to -10 while stirring. Then 106 grams of psi-ionone having a purity of 90.6% were added within 10 minutes, so that the temperature is maintained between -5 and 0C. After completion the dark-red-brownish reaction product was stirred for additional 15 minutes at a temperature between -10 and -20C. Thereafter, water is added dropwise within 15 minutes in an amount to result in a final diluted sulfuric acid concentration as given in Table 1, so that the temperature at the end of the addition is 5C. Alter two-third of the water addition the cooler was switched off and the cooling liquid was removed from the jacket. Then the reaction mixture was stirred for additional 15 minutes at 5C and the two-phase system was thereafter allowed to settle. The diluted aqueous sulfuric acid phase was removed and extracted twice with 135 grams of methylene chloride. The combined methylene chloride solutions were washed with 100 grams of water-Thereafter the pH was adjusted to a pH of 8 to 9 by addition of triethyl amine, followed by washing with 200 grams of water. The methylene chloride phase was concentrated by evaporating methylene chloride using a rotational evaporator. Thereafter the raw beta-ionone is distilled for purification. In Table 1 the yield of beta-ionone, alpha-ionone and the distillation residue is given. Examples 2 - 7; Example 1 was repeated whereby water was added to achieve a final concentration of diluted sulfuric acid, as indicated in Table 1. The resultant yield of beta-ionone, alpha-ionone and the distillation residue is also reported in Table 1.; Thus, it has been shown that within the range of 45 to 65% for the final concentration of the aqueous diluted acid phase, contrary to the teaching of the prior art, the yield of desired final product is approximately the same as for the final concentration of 19%, as previously used in the standard beta-ionone process, Thus, a higher final concentration of the diluted acid can be used without compromising yield, thereby reducing the energy needed for subsequent concentration of the diluted acid for further use or re-use in the process of the present invention.
88%; 0.6%	With sulfuric acid; water; In hexane; at -20 - 5℃; for 0.916667h;Product distribution / selectivity;	Example 8; Example 5 was repeated using instead of methylene chloride, hexane. The yield of beta-ionone was 88.0%, the yield of alpha-ionone 0.6%, and the yield of distillation residue was 4.7%. This Example shows that with hexane similar ,results are obtained as with methylene chloride.
11%; 32%	With Amberlyst-36; In benzene; at 80℃; for 2h;	General procedure: The cyclization of pseudoionone (Scheme 2) was investigatedwith the FSMA/SiO2 nanocomposite. The conversion of pseudoionone and yield of ionone under FSMA/SiO2 are given in Table 3 with a comparison with the results by using Amberlyst-15, Amberlyst-36, Nafion NR50 and Nafion/SiO2. All of the catalysts containing RfSO3H (Entries 3-5) show good activity andselectivity except for Nafion NR50 because of its low surface area. Their excellent activity is attributed to their super-strong acidity of perfluoroalkanesulfonic acid group (RfSO3H). It is believed that their good selectivity is also ascribed to the bulky, lipophilic and flexible perfluoroalkyl side chain with ether linkage [46]. Due to higher surface area and more easily accessible acid sites, nanocomposites Nafion/SiO2 and FSMA/SiO2 exhibit higher yield than pure polymer catalysts. It took FSMA/SiO2 1 h to yield 62% of ?-ionone with quantitative conversion and 100% selectivity. In addition, we have tested the reusability of FSMA/SiO2 in the cyclization. FSMA/SiO2 recovered by simply washing with ethanol and drying was reused under the same conditions. In the five runs, FSMA/SiO2 showed high activity with the conversion of pseudoionone kept at 100%. In the sixth run, a slight deactivation took place with 93% of conversion. The result indicates good reusability of FSMA/SiO2 in the reaction

With sulfuric acid; water; In di-isopropyl ether; at -20 - 5℃; for 0.916667h;Product distribution / selectivity;

Example 9 (Comparative); Example 5 was repeated using diisopropyl ether instead of methylene chloride, thereby forming a single-phase reaction mixture. The combined yield of alpha- and beta-ionone was less than 50%. Example 10 shows that using a solvent that is miscible with the strong acid results in a dramatic drop of the yield of the desired product.

Reference： [1]Patent: EP1921058,2008,A1 .Location in patent: Page/Page column 7-8
[2]Patent: EP1921058,2008,A1 .Location in patent: Page/Page column 8
[3]Journal of Molecular Catalysis A: Chemical,2012,vol. 365,p. 73 - 79
[4]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 411 - 434
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 457 - 483
[5]Pharmaceutical Chemistry Journal,1998,vol. 32,p. 603 - 605
Khimiko-Farmatsevticheskii Zhurnal,1998,vol. 32,p. 36 - 38
[6]Chemical Communications,2005,p. 3556 - 3558
[7]Patent: EP1921058,2008,A1 .Location in patent: Page/Page column 8

6
[ 1055-23-8 ]
[ 127-41-3 ]
[9,9']Bianthracenyl; compound with (E)-4-((R)-6,6-dimethyl-cyclohex-2-enyl)-but-3-en-2-one [ No CAS ]

Reference： [1]Angewandte Chemie,1990,vol. 102,p. 688 - 689

7
[ 127-41-3 ]
[ 3084-53-5 ]
[ 58102-12-8 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 1877 - 1880

8
[ 127-41-3 ]
[ 190059-33-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide; m-chloroperoxybenzoic acid; In chloroform-d1; dichloromethane;	EXAMPLE I Preparation of 4-(1,3,3-Trimethyl-7-oxabicyclo[4.1.0]hept-2-yl)but-3-en-2-one To a 50-mL 2-neck reaction flask fitted with an addition funnel and an adapter connected to an apparatus similar to that described by Johnson and Schneider ?Org. Synth., 30, 18[(1950)] so that the mixture in the flask could be protected from atmospheric moisture, et al. throughout the course of the reaction were added a Teflon-coated spin bar, 1.254 g (5.81 mmoles) of 80% 3-chloroperoxybenzoic acid (purchased from Aldrich Chemical Co., Milwaukee, Wis.), and 10.0 mL of A.C.S. reagent-grade dichloromethane. After placing the flask in an ice-water bath (0 C.), a solution of 1.00 mL (4.84 mmoles) of <strong>[127-41-3]alpha-ionone</strong> (purchased from Aldrich Chemical Co., Milwaukee, Wis.) in 5.0 mL of A.C.S. reagent-grade dichloromethane was added dropwise to the stirred reaction mixture over a period of 5 minutes. The resulting mixture was subsequently stirred at 0 C. for 2 hours. After dilution of the mixture with 40 mL of ether, the organic layer was washed twice with 50 mL portions of 4:1 (v/v) 1 M aqueous sodium hydroxide: 15% aqueous sodium chloride and once with 50 mL of saturated brine. The organic extracts were then dried over anhydrous sodium sulfate and subsequently filtered. Removal of the volatile organic solvents by evaporation at reduced pressure afforded 960 mg (95% yield) of the named epoxyketone. The identity and purity of this compound were ascertained by proton NMR analysis (recorded in CDCl3 solution at 300 MHz). The latter spectrum exhibited a doublet of doublets (J=15.9, 10.2 Hz) at delta 6.73 (vinyl H), a doublet (J=15.9 Hz) at delta 6.103 (vinyl H adjacent to C=O), a singlet at delta 2.30 (CH3 C=0), a singlet at delta 1.260 (CH3 bonded to C-1 in the bicyclic system), and singlets at delta 0.937 and 0.757 (two CH3 's bonded to C-3 in the bicyclic system). For a previous synthesis of this named epoxide, see: D. W. Brooks, et al., J. Org. Chem., 50, 628 (1985).
	With peracetic acid; sodium acetate; In dichloromethane; acetic acid;	EXAMPLE 9 1-(2,6,6-Trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-penta-1,4-dien-3-ol A solution of <strong>[127-41-3]alpha-ionone</strong> (202.5g; 94% by glc) in dichloromethane (1100 ml) containing anhydrous sodium acetate (50g) was cooled to 15 and treated over 30 min with peracetic acid (250 ml; 40% in acetic acid; from FMC). After stirring for 21/2 hours the reaction was no longer exothermic and the reaction mixture was stirred a further 3 hours at RT and then washed with water (2500ml), aqueous potassium metabisulfite solution (10%; 2250ml), sodium hydroxide solution (2M; 400ml) and water (400ml). Removal of the solvents gave the 4-(2,6,6-trimethyl-2,3-epoxy-cyclohex-1-yl)-3-buten-2-one having a nmr spectrum virtually identical with a distilled sample.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 8h;Darkness;	Example 2 - Synthesis of 4,5-epoxy-4,5-dihydro-<strong>[127-41-3]alpha-ionone</strong> A solution of 600 mul of dichloromethane and 11 mul di of (R,S)-3-(E)-buten-2-one,4-(2,6,6-trimethyl-2-cyclohexen-1-yl), or <strong>[127-41-3]alpha-ionone</strong> (Sigma Aldrich) (0.052 mmol; 1 eq) is kept under magnetic stirring at T = 0 C. To said solution 13.4 mg of m-chloro-perbenzoic acid (0.078 mmol; 1.5 eg) are added, and stirring is continued in the dark and at room temperature for eight hours. The reaction is monitored by TLC (hexane:ethyl acetate:acetic acid 50:35:1). When the reaction is ended, the obtained solution is mixed with ammonium hydrogen carbonate and is extracted with ethyl acetate (3 x 3 ml). The organic phase is then concentrated to a small volume in vacuo, with a thick oil being obtained, which is purified by HPLC.

	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 2h;	To a stirred solution of Compound-1 (8 g, 41.6 mmol) in dry DCM (120 mL) at 0 C was slowly added m-CPBA (15.8 g, 91 mmol). The resulting mixture was stirred at room temperature for 2 h. Then the mixture was filtered and the precipitate was washed with DCM. The combined filtrate was washed serially with 10% aq. Na2SO3, 5% aq. NaOH,water and brine, dried over anhydrous Na2SO4 and concentrated to obtain Compound-2 (10.2 g).The crude material was used for the next step without further purification. MS (m/z): [M + H]+,209.2.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 5℃; for 1h;	(±)-4-Hydroxy-beta-ionone was synthesized as described previously[33]. The epoxidation of <strong>[127-41-3]alpha-ionone</strong> (1 g, 5.3 mmol) with m-CPBA(1.4 equivalents) at 5C for 1 h in 20 mL of CH2Cl2 yielded 4,5-epoxide. The 4,5-epoxide was subjected to a base catalyzed rearrangementby refluxing with K2CO3 (3.0 equivalent) in methanolfor 4 h to yield the final compound. Most of the methanolwas then evaporated, and the residue was dissolved in ethyl acetate.The organic phase was washed successively with water and brine. The solution was evaporated and the residue was purifiedby silica gel column chromatography (ethyl acetate-hexane65: 35) to give the (±)-4-hydroxy-beta-ionone white powder(420 mg, 48%) with 1H NMR (CDCl3, 800 MHz) delta 7.18 (1H, dq,J = 16.4, 1.3 Hz, H-8), 6.11 (1H, d, J = 16.4 Hz, H-7), 4.01 (1H, t,J = 4.9Hz), 2.55-2.53 (1H, m, H-3), 2.35 (3H, s, H-11) 1.90-1.89(1H,m, H-2), 1.80 (3H, d, J = 1.0 Hz, H-10), 1.19 (6H, s, H-12, 13);13C NMR (CDCl3, 200 MHz) delta 198.5 (C, C-9), 142.7 (CH, C-7),139.4 (C, C-6), 133.9 (C, C-5), 133.0 (C, C-8), 69.9 (CH, C-4),35.5 (C, C-1), 34.6 (CH2, C-2), 28.8 (CH3, C-12 or - 13), 28.3(CH2, C-3), 27.5 (CH3, C-12 or - 13), 27.3 (CH3, C-10), 18.4 (CH3,C-11); EIMS m/z 208 [M]+ (21), 137 (17), 123 (25), 109 (79), 95(18), 91 (20), 43 (100), and 41 (24).
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 1h;	MCPBA (22.8 g, 0.116 mol) dissolved in CH2Cl2(60 mL)was added dropwise over 30 min to a solution of <strong>[127-41-3]alpha-ionone</strong>(22.2 g, 0.116 mol) in CH2Cl2(85 mL) at 0 C. The mixturewas stirred for 1 h at 10 C to complete the reactionaccording to TLC and GC. Then, the reaction mixture wasfiltered and the residue was washed with CH2Cl2(50 mL).The above combined CH2Cl2was then washed with 10%aq Na2SO3,5% aq NaOH and water successively and dried(MgSO4). The crude product epoxide 5 was afforded by concentrationin vacuo in 95% yield (21.1 g) with a content of92.6% (GC). GC-MS: m/z (%) = 208, 193, 109.

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9
[ 127-41-3 ]
[ 13720-37-1 ]
[ 31499-72-6 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 5344 - 5348
[2]Phytochemistry,1994,vol. 37,p. 737 - 740

10
[ 127-41-3 ]
[ 30364-38-6 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 1853 - 1856

11
[ 25312-34-9 ]
[ 127-41-3 ]

Reference： [1]Chemistry Letters,1989,p. 1361 - 1364
[2]Tetrahedron,2003,vol. 59,p. 3493 - 3498
[3]Organic Letters,2002,vol. 4,p. 2669 - 2672

12
[ 141-10-6 ]
[ 127-41-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	With omega-sulfonic-perfluoroalkylated poly(styrene-maleic anhydride)/silica hybrid nanocomposites; In benzene; at 80℃; for 1h;	General procedure: The cyclization of pseudoionone (Scheme 2) was investigatedwith the FSMA/SiO2 nanocomposite. The conversion of pseudoionone and yield of ionone under FSMA/SiO2 are given in Table 3 with a comparison with the results by using Amberlyst-15, Amberlyst-36, Nafion NR50 and Nafion/SiO2. All of the catalysts containing RfSO3H (Entries 3-5) show good activity andselectivity except for Nafion NR50 because of its low surface area. Their excellent activity is attributed to their super-strong acidity of perfluoroalkanesulfonic acid group (RfSO3H). It is believed that their good selectivity is also ascribed to the bulky, lipophilic and flexible perfluoroalkyl side chain with ether linkage [46]. Due to higher surface area and more easily accessible acid sites, nanocomposites Nafion/SiO2 and FSMA/SiO2 exhibit higher yield than pure polymer catalysts. It took FSMA/SiO2 1 h to yield 62% of ?-ionone with quantitative conversion and 100% selectivity. In addition, we have tested the reusability of FSMA/SiO2 in the cyclization. FSMA/SiO2 recovered by simply washing with ethanol and drying was reused under the same conditions. In the five runs, FSMA/SiO2 showed high activity with the conversion of pseudoionone kept at 100%. In the sixth run, a slight deactivation took place with 93% of conversion. The result indicates good reusability of FSMA/SiO2 in the reaction

Reference： [1]Pharmaceutical Chemistry Journal,1998,vol. 32,p. 603 - 605
Khimiko-Farmatsevticheskii Zhurnal,1998,vol. 32,p. 36 - 38
[2]Journal of Molecular Catalysis A: Chemical,2012,vol. 365,p. 73 - 79

13
[ 127-41-3 ]
[ 22029-76-1 ]
[ 25312-34-9 ]

Reference： [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 5333 - 5336

14
[ 127-41-3 ]
[ 887256-12-4 ]

Yield	Reaction Conditions	Operation in experiment
99.6%	With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; at 55℃; for 3h;	10 g and 0.052 mol of <strong>[127-41-3]alpha-ionone</strong>, Compound A, were dissolved in 20 ml of ethanol, and then added to the flask, and 3.8 g and 0.06 mol of hydroxylamine hydrochloride were sequentially added to the flask.6.4 g, 0.07 mol of sodium acetate and 15 ml of deionized water.After all were added, the temperature of the system was raised to 55 C and the reaction time was controlled for 3 h. After the reaction, 60 ml of deionized water was added to the system, and the mixture was extracted with ethyl acetate. The organic phase was combined, and the organic phase was washed with 10% saturated sodium hydrogenAfter steaming, an orange-yellow liquid was obtained, which was placed in a refrigerator as a solid, which was <strong>[127-41-3]alpha-ionone</strong>, Compound B, and the yield was 99.6%.

Reference： [1]Patent: CN108558623,2018,A .Location in patent: Paragraph 0075-0076
[2]Molecules,2005,vol. 10,p. 990 - 999
[3]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 1032 - 1039

15
[ 127-41-3 ]
[ 459-57-4 ]
[ 905965-30-2 ]

Yield	Reaction Conditions	Operation in experiment
	With cetyltrimethylammonim bromide; sodium hydroxide; In water; at 20℃; for 24h;	General procedure: A mixture of beta-ionone (2.32 g, 2.49 ml, 12 mmol), substituted benzaldehydes (10 mmol), cetyl trimethyl ammonium bromide (0.14 g, 1 mmol), sodium hydroxide (1.0 g, 30 mmol) and water (50 ml) was stirred at room temperature for 24 hours. After completion of reaction (TLC monitoring), it was extracted with ethyl acetate. The combined organic extract was washed with water, brine solution, dried (Na2SO4) and solvent was removed. Crude product was purified by column chromatography (SiO2, 60-120 mesh).

Reference： [1]European Journal of Medicinal Chemistry,2006,vol. 41,p. 779 - 785
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 248 - 251

16
[ 127-41-3 ]
[ 555-16-8 ]
[ 905965-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	With cetyltrimethylammonim bromide; sodium hydroxide; In water; at 20℃; for 24h;	General procedure: A mixture of beta-ionone (2.32 g, 2.49 ml, 12 mmol), substituted benzaldehydes (10 mmol), cetyl trimethyl ammonium bromide (0.14 g, 1 mmol), sodium hydroxide (1.0 g, 30 mmol) and water (50 ml) was stirred at room temperature for 24 hours. After completion of reaction (TLC monitoring), it was extracted with ethyl acetate. The combined organic extract was washed with water, brine solution, dried (Na2SO4) and solvent was removed. Crude product was purified by column chromatography (SiO2, 60-120 mesh).

Reference： [1]European Journal of Medicinal Chemistry,2006,vol. 41,p. 779 - 785
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 248 - 251

17
[ 127-41-3 ]
[ 86-81-7 ]
[ 905965-28-8 ]

Yield	Reaction Conditions	Operation in experiment
	With cetyltrimethylammonim bromide; sodium hydroxide; In water; at 20℃; for 24h;	General procedure: A mixture of beta-ionone (2.32 g, 2.49 ml, 12 mmol), substituted benzaldehydes (10 mmol), cetyl trimethyl ammonium bromide (0.14 g, 1 mmol), sodium hydroxide (1.0 g, 30 mmol) and water (50 ml) was stirred at room temperature for 24 hours. After completion of reaction (TLC monitoring), it was extracted with ethyl acetate. The combined organic extract was washed with water, brine solution, dried (Na2SO4) and solvent was removed. Crude product was purified by column chromatography (SiO2, 60-120 mesh).

Reference： [1]European Journal of Medicinal Chemistry,2006,vol. 41,p. 779 - 785
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 248 - 251

18
[ 127-41-3 ]
[ 146137-78-2 ]
C₂₁H₂₂F₄O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1183 - 1186

19
[ 588-96-5 ]
[ 127-41-3 ]
[ 1225454-13-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1964 - 1971

20
[ 1277166-78-5 ]
[ 127-41-3 ]

Yield	Reaction Conditions	Operation in experiment
70%		In a screw cap vial, [{Au(IPr)}2(mu-OH)][BF4] (6.3 mg, 4.9 × 10-3 mmol) was added to a solution of propargylic benzoate 4c (73 mg, 0.25 mmol) in a mixture of butanone/water (2.5 ml + 25 mul), then the reaction mixture was stirred at 60 C for 12 h. The solvent was removed at reduced pressure and CH2Cl2 (2.5 ml), followed by two crystals of I2 were added. After 2 h of stirring at rt, the reaction mixture was quenched by the addition of a saturated aqueous solution of Na2S2O3, then the aqueous layer was extracted with CH2Cl2 (3 × 20 ml), and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The crude product was purified by column chromatography (pentane/Et2O 98:2) to give pure (E)-alpha-ionone 1, identical with a commercial authentic sample (33 mg, 70%). 1H NMR (300 MHz, CDCl3) delta 0.87 (s, 3H), 0.94 (s, 3H), 1.19-1.29 (m, 1H), 1.47 (ddd, J = 13.3, 8.3, 8.1 Hz, 1H), 1.58 (q, J = 1.7 Hz, 3H), 2.0-2.10 (m, 2H), 2.26 (s, 3H), 2.30 (d, J = 9.2 Hz, 1H), 5.48-5.55 (m, 1H), 6.06 (d, J = 16.0 Hz, 1H), 6.63 (dd, J = 16.0, 9.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 22.8 (q), 23.0 (t), 26.7 (q), 26.9 (q), 27.8 (q), 31.1 (t), 32.5 (s), 54.2 (d), 122.6 (d), 131.9 (s), 132.3 (d), 149.1 (d), 198.6 (s); HRMS calcd for C13H20O: 192.15142. Found: 192.15145.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1124 - 1127

21
[ 127-41-3 ]
[ 108-24-7 ]
[ 928781-14-0 ]

Yield	Reaction Conditions	Operation in experiment
70%		Example 1 Synthesis of alpha-Ionone Enol Acetate To a solution prepared by dissolving 164 g of diisopropylamine in 3,500 mL of tetrahydrofuran (THF) was added dropwise 1,000 mL of a hexane solution of n-butyllithium with stirring at -10 C., followed by stirring for 1 hour. Thereafter, a solution prepared by dissolving 260 g of <strong>[127-41-3]alpha-ionone</strong> (1) in 3,000 mL of THF was added dropwise to the obtained solution at -10 C., followed by stirring for 1 hour, and then 138 g of acetic anhydride was added dropwise at -10 C. After completion of such dropwise addition, the obtained mixture was subjected to react with stirring for 30 minutes. After completion of the reaction, the reaction mixture was analyzed by GC. As a result, it was confirmed that the conversion rate of the <strong>[127-41-3]alpha-ionone</strong> was 90.9%. A post-treatment was carried out by a conventional method, to give 295 g of a crude product. The obtained crude product was distilled, to give 221 g of desired <strong>[127-41-3]alpha-ionone</strong> enol acetate (DM top 80 C.; 0.2 mmHg; 70% yield).

Reference： [1]Patent: US7902404,2011,B2 .Location in patent: Page/Page column 40-41

22
[ 127-41-3 ]
[ 221046-97-5 ]
α-ionol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; potassium carbonate;trans-RuCl2((S)-2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthyl)((S)-1,1-di(4-anisyl)-2-isopropyl-1,2-ethylenediamine); In isopropyl alcohol; at 30℃; under 22502.3 Torr; for 21h;Inert atmosphere;	Example 10(1) Asymmetric Hydrogenation of alpha-Ionone (Racemic Form)Under a nitrogen atmosphere, 64 mg of RuCl2 [(S)-DM-BINAP][(S)-DAIPEN], 720 mg of K2CO3, 100 mL of IPA, and 20 g of <strong>[127-41-3]alpha-ionone</strong> as a racemic form were mixed. After deaeration, the obtained mixture was subjected to an asymmetric hydrogenation at 30 C. and a hydrogen pressure of 3 MPa for 21 hours. The reaction pressure was returned to the constant pressure. It was confirmed by GC that the raw material disappeared, and a post-treatment was then carried out by a conventional method, to give 20.2 g of desired optically active alpha-ionol (100% yield; 90% e.e.; 0% d.e.).

Reference： [1]Patent: US7902404,2011,B2 .Location in patent: Page/Page column 45-46

23
[ 127-41-3 ]
[ 144-68-3 ]

Reference： [1]Patent: US8222458,2012,B2

24
[ 127-41-3 ]
[ 27996-86-7 ]
[ 1432043-44-1 ]

Yield	Reaction Conditions	Operation in experiment
23%	With cetyltrimethylammonim bromide; sodium hydroxide; In water; at 20℃; for 24h;	A mixture of alpha ionone (1.152 g, 1.23 ml, 6 mmol), 4-(1H-1,2,4-triazol-1-yl) benzaldehydes (0.865 g, 5 mmol), cetyltrimethyl ammonium bromide (0.070 g, 0.5 mmol), sodium hydroxide (0.600 g, 15 mmol) and water (25 ml) was stirred at room temperature for 24 h. Reaction progress was monitored by TLC and compound was extracted with ethyl acetate (2 × 50 ml). The combined organic extract was washed with water (2 × 50 ml), brine solution (50 ml), dried (Na2SO4) and the solvent was removed in vacuum. The crude product was purified by column chromatography (SiO2, 60-120 mesh). Elution with 10 % ethyl acetate in hexane furnished a pale yellow coloured solid (0.400g, 23%). Mp: 108-110OC; IR (KBr, cm-1): 2915, 1651 (C=O), 1598 (C=N); 1H NMR (CDCl3, 300 MHz): delta 0.88 (s, 3H), 0.95 (s, 3H), 1.22-1.29 (m, 1H), 1.43-1.52 (m, 1H), 1.60 (s, 3H), 2.07 (brs, 2H), 2.36 (d, J = 9 Hz, 1H), 5.53 (brs, 1H), 6.39 (d, J = 16 Hz, 1H), 6.85 (dd, J = 16, 9 Hz, 1H), 7.01 (d, J = 16 Hz, 1H), 7.63-7.74 (m, 5H), 8.11 (s, 1H), 8.60 (s, 1H); 13C NMR (CDCl3, 75 MHz): delta 22.92, 23.10, 26.90, 27.95, 31.25, 32.75, 54.67, 2×120.13, 122.83, 125.72, 2×129.72, 130.54, 131.93, 134.81, 137.99, 140.89, 141.16, 149.44, 152.81, 188.53; ESI-MS m/z: 348 [M+1]+; Analysis calculated for C22H25N3O: C, 76.05; H, 7.25; N, 12.09; Found: C, 76.05; H, 7.29; N, 12.03.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2925 - 2928

25
[ 5381-20-4 ]
[ 127-41-3 ]
C₂₂H₂₄OS [ No CAS ]

Reference： [1]Investigational New Drugs,2014,vol. 32,p. 227 - 234

26
[ 127-41-3 ]
[ 3536-96-7 ]
[ 59861-10-8 ]

Yield	Reaction Conditions	Operation in experiment
60%		Ferric chloride (0.02 mmol) and ligand triphenylphosphine (0.2 mmol) were added to the reaction tube, and solvent diethyl ether (5 ml) and hydrazine-ionone (1 mmol) were added under a nitrogen atmosphere. The solution was placed at a temperature of -10 C, and a solution of vinylmagnesium chloride (1 mmol) in tetrahydrofuran was added dropwise to the reaction tube while stirring, and the reaction was continued at -10 C. After 5 hours,The reaction was confirmed by gas chromatography. The reaction tube was returned to room temperature and cooled to zero. The reaction was quenched by dropwise addition of a saturated ammonium chloride solution, and then returned to room temperature and then water was added. Extracted with ether,The organic phase is washed one by one with 1% hydrochloric acid, saturated sodium hydrogencarbonate and saturated brine.Then, it is dried over anhydrous sodium sulfate, filtered, concentrated, and purified by flash column chromatography to give 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-5-hexene-2 -ketone, yield 60%, The product was a colorless liquid, and the nuclear magnetic data of the material is shown in Example 1.

Reference： [1]Patent: CN108164401,2018,A .Location in patent: Paragraph 0017-0019

27
[ 201230-82-2 ]
[ 127-41-3 ]
[ 31499-72-6 ]

Yield	Reaction Conditions	Operation in experiment
	With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; In toluene; at 120℃; under 60804.1 Torr; for 5h;	General procedure: All chemical products were from commercial sources and used without special treatment, unless otherwise indicated. (R)-(+)-limonene (97 %), alpha-terpineol ((?95 %), (-)-terpinen-4-ol (?95 %), <strong>[127-41-3]alpha-ionone</strong> (90 %), triphenylphosphine (PPh3) and tris(2,4-di-tert-butylphenyl)phosphite, (2,4-di-tBuC6H3O)3P, were received from Sigma-Aldrich. The catalyst precursor, [Rh(COD)(OMe)]2 (COD=1,5-cyclooctadiene), was synthesized by a previously reported method [41]. Toluene (anhydrous, 99.8 %), diethyl carbonate (DEC) (anhydrous, ?99 %), anisole (anhydrous, 99.7 %) and p-cymene (99 %) were purchased from Sigma-Aldrich. Toluene was passed through a silica column and stored in an argon-filled glove box. Anisole, purchased in a Sure/Seal bottle, was opened, stored in the glove box and used without special treatment. DEC was distilled under argon and stored over 4A molecular sieves. p-Cymene was distilled in a Kugelrohr distillation apparatus, collected under argon and stored in the glove box. Catalytic reactions were run in a 100mL homemade stainless steel autoclave with magnetic stirring. Aliquots were periodically taken from the reaction solutions using a valved dip tube without depressurization of the reactor. The samples were analyzed by gas chromatography (GC) using a GC- Shimadzu GC2010 chromatograph equipped with a Rtx-5MS capillary column and FID detector. Conversion and selectivity were calculated based on the reacted substrate using p-xylene as an internal standard. Initial turnover frequencies (TOFs) were calculated at low conversions, usually less than 40 %. In a typical run, a solution (20.0mL) of the substrate (4mmol), [Rh(COD)(OMe)]2 (5.0 mumol), phosphorus ligand (0-0.30mmol) and p-xylene (2mmol, GC internal standard) in a specified solvent was placed into the reactor under argon; the reactor was pressurized with ?syngas? to 40-80atm (CO/H2=1/2 to 2/1) and heated to the specified temperature. Then, the reaction mixture was stirred with a magnetic stirrer for the specified time. After the reaction, the solutions were analyzed by gas chromatography/mass spectrometry (GC-MS) on a Shimadzu QP2010-PLUS equipment operating at 70eV. Main reaction products were isolated from the reaction solutions by column chromatography (silica gel 60, hexane/ethyl acetate mixtures) and identified by NMR spectroscopy (DEPT, COSY, HMQC, HMBC and NOESY experiments) on a Bruker 400MHz spectrometer (CDCl3, TMS) (see Supplementary Material).

Reference： [1]Applied Catalysis A: General,2020,vol. 591

28
[ 201230-82-2 ]
[ 127-41-3 ]
[ 31499-72-6 ]
C₁₄H₂₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; In toluene; at 120℃; under 60804.1 Torr; for 24h;	General procedure: All chemical products were from commercial sources and used without special treatment, unless otherwise indicated. (R)-(+)-limonene (97 %), alpha-terpineol ((?95 %), (-)-terpinen-4-ol (?95 %), <strong>[127-41-3]alpha-ionone</strong> (90 %), triphenylphosphine (PPh3) and tris(2,4-di-tert-butylphenyl)phosphite, (2,4-di-tBuC6H3O)3P, were received from Sigma-Aldrich. The catalyst precursor, [Rh(COD)(OMe)]2 (COD=1,5-cyclooctadiene), was synthesized by a previously reported method [41]. Toluene (anhydrous, 99.8 %), diethyl carbonate (DEC) (anhydrous, ?99 %), anisole (anhydrous, 99.7 %) and p-cymene (99 %) were purchased from Sigma-Aldrich. Toluene was passed through a silica column and stored in an argon-filled glove box. Anisole, purchased in a Sure/Seal bottle, was opened, stored in the glove box and used without special treatment. DEC was distilled under argon and stored over 4A molecular sieves. p-Cymene was distilled in a Kugelrohr distillation apparatus, collected under argon and stored in the glove box. Catalytic reactions were run in a 100mL homemade stainless steel autoclave with magnetic stirring. Aliquots were periodically taken from the reaction solutions using a valved dip tube without depressurization of the reactor. The samples were analyzed by gas chromatography (GC) using a GC- Shimadzu GC2010 chromatograph equipped with a Rtx-5MS capillary column and FID detector. Conversion and selectivity were calculated based on the reacted substrate using p-xylene as an internal standard. Initial turnover frequencies (TOFs) were calculated at low conversions, usually less than 40 %. In a typical run, a solution (20.0mL) of the substrate (4mmol), [Rh(COD)(OMe)]2 (5.0 mumol), phosphorus ligand (0-0.30mmol) and p-xylene (2mmol, GC internal standard) in a specified solvent was placed into the reactor under argon; the reactor was pressurized with ?syngas? to 40-80atm (CO/H2=1/2 to 2/1) and heated to the specified temperature. Then, the reaction mixture was stirred with a magnetic stirrer for the specified time. After the reaction, the solutions were analyzed by gas chromatography/mass spectrometry (GC-MS) on a Shimadzu QP2010-PLUS equipment operating at 70eV. Main reaction products were isolated from the reaction solutions by column chromatography (silica gel 60, hexane/ethyl acetate mixtures) and identified by NMR spectroscopy (DEPT, COSY, HMQC, HMBC and NOESY experiments) on a Bruker 400MHz spectrometer (CDCl3, TMS) (see Supplementary Material).

Reference： [1]Applied Catalysis A: General,2020,vol. 591

29
[ 201230-82-2 ]
[ 127-41-3 ]
[ 31499-72-6 ]
C₁₄H₂₄O₂ [ No CAS ]
C₁₄H₂₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; In toluene; at 120℃; under 60804.1 Torr; for 170h;	General procedure: All chemical products were from commercial sources and used without special treatment, unless otherwise indicated. (R)-(+)-limonene (97 %), alpha-terpineol ((?95 %), (-)-terpinen-4-ol (?95 %), <strong>[127-41-3]alpha-ionone</strong> (90 %), triphenylphosphine (PPh3) and tris(2,4-di-tert-butylphenyl)phosphite, (2,4-di-tBuC6H3O)3P, were received from Sigma-Aldrich. The catalyst precursor, [Rh(COD)(OMe)]2 (COD=1,5-cyclooctadiene), was synthesized by a previously reported method [41]. Toluene (anhydrous, 99.8 %), diethyl carbonate (DEC) (anhydrous, ?99 %), anisole (anhydrous, 99.7 %) and p-cymene (99 %) were purchased from Sigma-Aldrich. Toluene was passed through a silica column and stored in an argon-filled glove box. Anisole, purchased in a Sure/Seal bottle, was opened, stored in the glove box and used without special treatment. DEC was distilled under argon and stored over 4A molecular sieves. p-Cymene was distilled in a Kugelrohr distillation apparatus, collected under argon and stored in the glove box. Catalytic reactions were run in a 100mL homemade stainless steel autoclave with magnetic stirring. Aliquots were periodically taken from the reaction solutions using a valved dip tube without depressurization of the reactor. The samples were analyzed by gas chromatography (GC) using a GC- Shimadzu GC2010 chromatograph equipped with a Rtx-5MS capillary column and FID detector. Conversion and selectivity were calculated based on the reacted substrate using p-xylene as an internal standard. Initial turnover frequencies (TOFs) were calculated at low conversions, usually less than 40 %. In a typical run, a solution (20.0mL) of the substrate (4mmol), [Rh(COD)(OMe)]2 (5.0 mumol), phosphorus ligand (0-0.30mmol) and p-xylene (2mmol, GC internal standard) in a specified solvent was placed into the reactor under argon; the reactor was pressurized with ?syngas? to 40-80atm (CO/H2=1/2 to 2/1) and heated to the specified temperature. Then, the reaction mixture was stirred with a magnetic stirrer for the specified time. After the reaction, the solutions were analyzed by gas chromatography/mass spectrometry (GC-MS) on a Shimadzu QP2010-PLUS equipment operating at 70eV. Main reaction products were isolated from the reaction solutions by column chromatography (silica gel 60, hexane/ethyl acetate mixtures) and identified by NMR spectroscopy (DEPT, COSY, HMQC, HMBC and NOESY experiments) on a Bruker 400MHz spectrometer (CDCl3, TMS) (see Supplementary Material).

Reference： [1]Applied Catalysis A: General,2020,vol. 591

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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

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. 127-41-3 ] {[proInfo.proName]}

Quality Control of [ 127-41-3 ]

Related Doc. of [ 127-41-3 ]

Product Details of [ 127-41-3 ]

Calculated chemistry of [ 127-41-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 127-41-3 ]

Application In Synthesis of [ 127-41-3 ]

[ 127-41-3 ] Synthesis Path-Upstream 1~1

[ 127-41-3 ] Synthesis Path-Downstream 1~29

Related Functional Groups of [ 127-41-3 ]

Alkenes

Aliphatic Cyclic Hydrocarbons

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 127-41-3 ]