[ CAS No. 110-93-0 ] {[proInfo.proName]}

Name: 110-93-0|6-Methyl-5-hepten-2-one|98%
Brand: Ambeed
SKU: A565531
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Quality Control of [ 110-93-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 110-93-0 ]

Product Details of [ 110-93-0 ]

CAS No. :	110-93-0	MDL No. :
Formula :	C₈H₁₄O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UHEPJGULSIKKTP-UHFFFAOYSA-N
M.W :	126.20	Pubchem ID :	9862
Synonyms :	6-Methyl-5-hepten-2-one	Chemical Name :	6-Methyl-5-hepten-2-one

Calculated chemistry of [ 110-93-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.62
Num. rotatable bonds :	3
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.3
TPSA :	17.07 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) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.23
Log Po/w (XLOGP3) :	1.88
Log Po/w (WLOGP) :	2.32
Log Po/w (MLOGP) :	1.97
Log Po/w (SILICOS-IT) :	1.96
Consensus Log Po/w :	2.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.61
Solubility :	3.11 mg/ml ; 0.0246 mol/l
Class :	Very soluble
Log S (Ali) :	-1.86
Solubility :	1.74 mg/ml ; 0.0138 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.85
Solubility :	1.79 mg/ml ; 0.0142 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.22

Safety of [ 110-93-0 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P403+P235	UN#:	1224
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 110-93-0 ]

* 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 [ 110-93-0 ]
Downstream synthetic route of [ 110-93-0 ]

[ 110-93-0 ] Synthesis Path-Upstream 1~7

1
[ 110-93-0 ]
[ 6138-90-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 45, p. 13448 - 13451[2] Angew. Chem., 2015, vol. 127, # 45, p. 13649 - 13653,5
[3] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2317 - 2324
[4] Organic Letters, 2018, vol. 20, # 6, p. 1613 - 1616

2
[ 110-93-0 ]
[ 74-86-2 ]
[ 29171-20-8 ]

Reference： [1] Patent: EP1852410, 2007, A1, . Location in patent: Page/Page column 5

3
[ 110-93-0 ]
[ 4301-14-8 ]
[ 29171-20-8 ]

Yield	Reaction Conditions	Operation in experiment
5.87 g	at -78 - 20℃; for 2 h;	To a solution of 6-methylhept-5-en-2-one (5.05 g, 40 mmol) in THF (100 mL) at -78 °C was added 0.5 M ethynylmagnesium bromide in THF (96 mL, 48.0 mmol) dropwsie through an addition funnel. The formed white slurry was allowed to warm up to rt and stirred for 2 h. Quenched with sat. NH₄C1, extracted with Ether. The separated organic layers were washed with brine, dried over Na₂S0₄, filtered, evaporated in vacuo. The residual oil was purified by FCC (0percent to 35percentEtOAc-Hexanes) to afford the desired product Cap W-24 Step A (5.87 g) as a colorless oil. NMR (500MHz, CDC1₃) δ 5.28 - 5.12 (m, 1H), 2.48 (s, 1H), 2.39 - 2.26 (m, 1H), 2.24 - 2.15 (m, 1H), 2.09 (br. s., 1H), 1.79 - 1.65 (m, 8H), 1.56 - 1.50 (m, 3H).

Reference： [1] Journal of the American Chemical Society, 2002, vol. 124, # 18, p. 5025 - 5036
[2] Tetrahedron Letters, 1999, vol. 40, # 46, p. 8113 - 8114
[3] Chemistry - A European Journal, 2006, vol. 12, # 11, p. 3006 - 3019
[4] Chemical Communications, 2015, vol. 51, # 5, p. 892 - 894
[5] Tetrahedron, 2005, vol. 61, # 20, p. 4793 - 4803
[6] Journal of Organic Chemistry, 2005, vol. 70, # 11, p. 4414 - 4422
[7] Journal of Agricultural and Food Chemistry, 2003, vol. 51, # 24, p. 7100 - 7105
[8] Journal of the American Chemical Society, 2012, vol. 134, # 21, p. 8770 - 8773
[9] Patent: WO2015/5901, 2015, A1, . Location in patent: Page/Page column 612
[10] Chemistry - A European Journal, 2015, vol. 21, # 48, p. 17210 - 17214

4
[ 110-93-0 ]
[ 74-86-2 ]
[ 29171-20-8 ]
[ 62179-75-3 ]

Yield	Reaction Conditions	Operation in experiment
67.6 - 94.3 %Chromat.	With potassium hydroxide In ammonia; water at 30℃; for 0.0833333 - 5 h;	796 mg of potassium hydroxide (KOH) in 45percent (wt. /vol.) aqueous solution and 20 194.5 g of 6-methyl-5-hepten-2-one (MH) were introduced into a reactor; the molar ratio KOH : MH was thus 1 : 250. After fourfold evacuation of the air from the reactor and subsequent flushing with nitrogen (inertisation of the reactor), 369 g of ammonia were introduced. Acetylene was then added to provide a pressure of 16.1 bar (1.61 MPa) at [30°C,] corresponding to 21percent (wt. /vol.) of acetylene in the mixture of ammonia and 25 acetylene. The contents of the reactor were agitated by gas stirring. Samples were taken at various time intervals for analysis of their content by gas chromatography (GC). After 5 hours the reaction was finally stopped since by then it had been established that a predominant amount of the desired product, 3, [7-DIMETHYL-6-OCTEN-1-YN-3-OL] (dehydrolinalool; DLL) and only small amounts of diol by-product and unchanged MH were present. The results are presented in Table 1 below

Reference： [1] Patent: WO2004/18400, 2004, A1, . Location in patent: Page 5-6

5
[ 110-93-0 ]
[ 74-86-2 ]
[ 29171-20-8 ]

Reference： [1] Tetrahedron, 1983, vol. 39, # 13, p. 2315 - 2322
[2] Doklady Akademii Nauk SSSR, 1957, vol. 114, p. 796[3] Doklady Chemistry, 112-117<1957>579,
[4] Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1458,1459[5] J. Gen. Chem. USSR (Engl. Transl.), 1958, vol. 28, p. 1511,1512
[6] Helvetica Chimica Acta, 1919, vol. 2, p. 184
[7] Helvetica Chimica Acta, 1929, vol. 12, p. 1140
[8] Bl.Inst.Pin, 1929, p. 247[9] Chem. Zentralbl., 1929, vol. 100, # II, p. 2774
[10] Collection of Czechoslovak Chemical Communications, 1960, vol. 25, p. 1914 - 1921

6
[ 110-93-0 ]
[ 1066-26-8 ]
[ 29171-20-8 ]

Reference： [1] Doklady Akademii Nauk SSSR, 1956, vol. 107, p. 103[2] Doklady Chemistry, 106-111<1956>151,
[3] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2501,2505; engl. Ausg. S. 2560, 2563

7
[ 60-29-7 ]
[ 110-93-0 ]
[ 74-86-2 ]
[ 29171-20-8 ]

Reference： [1] Helvetica Chimica Acta, 1919, vol. 2, p. 184

[ 110-93-0 ] Synthesis Path-Downstream 1~43

1
[ 24443-15-0 ]
[ 1118-67-8 ]
[ 110-93-0 ]
[ 64-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide

Reference： [1]Barbier; Bouveault [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1896, vol. 122, p. 1423]

2
[ 5392-40-5 ]
[ 110-93-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With pyrrolidine; water In acetonitrile at 20℃; for 12h;
	With water; potassium carbonate man destilliert mit Wasserdampf und fraktioniert im Vakuum;
	With potassium carbonate

	With potassium carbonate
	With sodium hydroxide In water	O.III OPERATING EXAMPLE III OPERATING EXAMPLE III Approximately 500 ml water, 5 g (90% active) sodium hydroxide, and 88 g terpeneless lemon grass oil containing approximately 95% citral were charged into a one-liter round bottom flask. The round bottom flask was equipped additionally with a trap having means of permitting removal of the lower density liquid while recirculating the higher density liquid, a fractionating column, and a means for stirring. The stirred contents of the flask were heated to reflux by means of a heating mantle. The pH of the contents was set at 12 and maintained at that level during the remainder of the run by addition of sodium hydroxide when necessary. The contents were refluxed for one hour, after which time the steam distillate was slowly collected. The distillate take-off was regulated so that little or no citral distilled over. The distillation was continued until no additional oil was collected. The oil phase distillate was separated from the steam condensate. The separated oil was then short-path vacuum distilled. The main cut yielded 72 g of the citral hydrolysis product, 6-methyl-5-hepten-2-one. The other reaction product, acetaldehyde, was vented from the flask through the fractionating column during the reaction. The yield of 6-methyl-5-hepten-2-one was approximately 90% under the above conditions.
	With palladium 10% on activated carbon; sodium formate In water at 180℃; for 0.333333h; Microwave irradiation; Sealed tube;	General procedures for the reduction of citral with microwave irradiation General procedure: The reduction of citral was carried out in a quartz tube (10 mL) under microwave irradiation. The order of addition of the reagents plays an important role in the reactions [27]. We selected the following standard protocol. Hydrogen donor was first dissolved in a solvent in the reactor, catalyst was then added, and finally the substrate was added. Then, the reaction vessel was sealed and the reaction was carried out under microwave irradiation at 300 W with a stirring speed of 900 r/min. The reaction time was started to count when the reaction mixture reached the desired temperature. After the reaction, the mixture was extracted with n-hexane and the resulting solution was analyzed with gas chromatography (GC-Shimadzu-14C, FID, Capillary column Rtx-Wax 30 m-0.53 mm- 0.25 mm) and gas chromatography/mass spectrometry (GC/MS, Agilent 5890). The gas phases were analyzed by Shimadzu GC-14C with TCD and a TDX-01 packed column. The reactions in the autoclave (50 mL) were also carried out in a water-bath with the same procedures.
	With β-lactoglobulin from milk In aq. phosphate buffer; ethanol at 37℃; for 96h; Darkness; Enzymatic reaction;

Reference： [1]Location in patent: scheme or table Enders, Dieter; Nguyen, Thanh V. [Tetrahedron Letters, 2012, vol. 53, # 16, p. 2091 - 2095]
[2]Verley [Bulletin de la Societe Chimique de France, 1897, vol. <3>17, p. 175][Chemische Berichte, 1899, vol. 32, p. 107]
[3]Verley [Bulletin de la Societe Chimique de France, 1897, vol. <3>17, p. 175][Chemische Berichte, 1899, vol. 32, p. 107] Barbe [Bulletin de l'Institut du pin, 1929, p. 246]
[4]Prileshajew [Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1911, vol. 43, p. 617][Chemisches Zentralblatt, 1911, vol. 82, # II, p. 268]
[5]Current Patent Assignee: GIVAUDAN SA - US4766249, 1988, A
[6]Liu, Ruixia; Wang, Yu; Cheng, Haiyang; Yu, Yancun; Zhao, Fengyu; Arai, Masahiko [Journal of Molecular Catalysis A: Chemical, 2013, vol. 366, p. 315 - 320]
[7]Gowda, Vishruth; Foley, Brendan; Du, Jasmine; Esteb, Megan; Watanabe, Coran M. H. [Organic and Biomolecular Chemistry, 2018, vol. 16, # 13, p. 2210 - 2213]

3
[ 110-93-0 ]
[ 3536-96-7 ]
[ 78-70-6 ]

Yield	Reaction Conditions	Operation in experiment
96.3%	With zinc(II) chloride; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere; Cooling with ice;	Under nitrogen protection,Add to a 2L three-necked flask with a constant pressure dropping funnelMethylheptenone (151.4 g, 1.2 mol),Solvent tetrahydrofuran (400.0mL)And zinc chloride (3.28 g, 24.0 mmol).Put a magnetic stirrer into the three-neck bottle.Put the three bottles in the ice water bath.Turn on the agitation,Vinyl magnesium chloride (660.0mL, 2.0M,a tetrahydrofuran solution) is charged into a constant pressure dropping funnel,Add dropwise to the methylheptenone solution with rapid stirring.The temperature of the reaction solution was controlled to be below 20 C during the dropwise addition.The addition is completed within 3 hours.Continue to stir the reaction for 1 hour.GC detects the organic phase,The reaction is complete,The conversion of methylheptenone is >99.0%,Product selectivity > 99.0%.Deionized water (23.8 g, 1.32 mmol) was added dropwise to the reaction mixture through a constant pressure dropping funnel.Quenching the unreacted Grignard reagent,The reaction solution quickly became cloudy,A large amount of inorganic magnesium salt is precipitated.Post-processing,First, the reaction solution is filtered,The filtrate obtained is subjected to rotary evaporation.Recovering the solvent tetrahydrofuran,The obtained linalool crude product,The crude product was further distilled under reduced pressure to give a pure linalool product of 179.9 g.Purity is 99.2%,The yield was 96.3%.

Reference： [1]Patent: CN109704922,2019,A .Location in patent: Paragraph 0039; 0040; 0041; 0042; 0045-0050
[2]Journal of Organic Chemistry,1957,vol. 22,p. 1602,1605

4
[ 110-93-0 ]
[ 1826-67-1 ]
[ 78-70-6 ]

Yield	Reaction Conditions	Operation in experiment
95.2%	With zinc(II) chloride; In tetrahydrofuran; at 20℃; for 5h;Inert atmosphere; Cooling with ice;	Under nitrogen protection,Methylheptenone (151.4 g, 1.2 mol) was added to a 2 L three-necked flask equipped with a constant pressure dropping funnel.Solvent ether (300.0 mL) and zinc chloride (1.64 g, 12.0 mmol).Put a magnetic stirrer into the three-neck bottle.Put the three bottles in the ice water bath.Turn on the agitation,Vinyl magnesium bromide (660.0 mL, 2.0 M,a tetrahydrofuran solution) is charged into a constant pressure dropping funnel.Add dropwise to the methylheptenone solution with rapid stirring.The temperature of the reaction solution was controlled to be below 20 C during the dropwise addition.After 3 hours, the drop is completed.Continue to stir the reaction for 2 hours.GC detects the organic phase,The reaction is complete,The conversion of methylheptenone is >99.0%,Product selectivity > 99.0%.Deionized water (23.8 g, 1.32 mmol) was added dropwise to the reaction mixture through a constant pressure dropping funnel.Quenching the unreacted Grignard reagent,The reaction solution quickly became cloudy,A large amount of inorganic magnesium salt is precipitated.Post-processing,First, the reaction solution is filtered,The filtrate obtained is subjected to rotary evaporation.Remove the solvent ether and tetrahydrofuran,The obtained crude linalool product,The crude product was further distilled under reduced pressure to give a pure linalool product, 178.0 g.Purity 99.0%,The yield was 95.2%.

Reference： [1]Patent: CN109704922,2019,A .Location in patent: Paragraph 0043; 0044
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1955,vol. 240,p. 631
[3]Organic Letters,2000,vol. 2,p. 571 - 572

5
[ 110-93-0 ]
[ 4630-06-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium tetrahydroborate; In methanol; at 20℃;	Briefly, sulcatone (500 mg, 3.97 mmol, Sigma-Aldrich) was added into a 50 mL round-bottomflask and dissolved in methanol (10 mL) before NaBH4 (160 mg, 3.97 mmol) was added. The mixturewas stirred magnetically at room temperature for 1 h. The reaction was then stopped by adding 1 mLof distilled water. The extraction of the product [(±)-6-methyl-5-hepten-2-ol (sulcatol)] was performedwith ethyl acetate (20 mL), which was then removed by rotary evaporation. Sulcatol was completelydried with N2, providing a 98% yield (500 mg, 3.91 mmol), and then treated pyridine (1 mL) andacetic anhydride (1 mL) for 24 h at room temperature. Subsequently, 10% HCl (4 mL) was added tothe reaction mixture, and 2-acetyl-6-methyl-5-heptene (sulcatyl acetate) was extracted from thereaction mixture with ethyl acetate (20 mL). The solvent was removed by rotary evaporation. Thesulcatyl acetate was completely dried with N2, and an 83% yield (550 mg, 3.24 mmol) was obtained.
96%	With [Ru{1-[2'-(hydroxymethyl)phenyl]-3-[4'-(methyl)phenyl]triazene}(Cl)(p-cymene)]; potassium hydroxide; In isopropyl alcohol; at 70℃; for 11h;Inert atmosphere; Schlenk technique;	General procedure: Complexes 5-8 were tested in the catalytic reduction of acetophenoneto 1-phenylethanol under the conditions showed inEq. (2). The results of the catalytic evaluation are summarized inTable 2. After 12 h yields of 1-phenylethanol were 94% and78% for 5 and 7, respectively (entry 1 and 5).
56%	With [(N,N?-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)3][Br]; potassium tert-butylate; hydrogen; In toluene; at 130℃; under 37503.8 Torr; for 48h;Glovebox; Autoclave;	General procedure: In a glove box, an autoclave was charged with the desired ketone (0.5 mmol), toluene (2 mL), Mn complex 1 (14 mg, 5 mol%) followed by t-BuOK (5.6 mg, 10 mol%), in this order. The autoclave is then closed and charged with H2 (50 bar).

18%	With [Ir(1-(1?-methylpyrazole)-3-(4?-methylphenyl)triazenide)Cp*Cl]; isopropyl alcohol; potassium hydroxide; at 90℃; for 24h;Inert atmosphere; Glovebox;Catalytic behavior;	General procedure: In the glovebox, ketone or alken-2-one (6.3×10-5 mol), 1,3,5-trimethylbenzene(2 muL) as internal standard and 0.7 mL of 2-propanol-d8were transferred into a J. Young NMR tube, and a 1H NMR spectrum wasrecorded. The tube was brought back into the glovebox, and precatalyst2 (1.26×10-6 mol in 0.2 mL of 2-propanol-d8) was added. At this point,KOH (0.5 M, 5 muL, 2 eq.) in 2-propanol-d8 was added only to those catalyticreactions performed in presence of base. Outside of the gloveboxthe tube was placed inside an oil bath at 90 C. The tube was removedfrom the oil bath at different times, and 1H NMR spectra were recordedin order to follow the progress of the reaction. The conversions weredetermined by the integration of either the aromatic protons or the aliphaticprotons of the ketone. The value of the integral for the singlet dueto the aromatic protons of 1,3,5-trimethylbenzene (internal standard)was set to 10 units. In addition, the conversion was also determined byGC-MS analysis in order to follow the deuteration process of the substrates,which is a consequence of using 2-propanol-d8. In addition, thetransfer hydrogenation reactions of some aryl- alkylketones and 5-alken-2-ones were performed as above using the same quantities of reactants(precatalyst 2 or 3 and KOH if needed) in regular 2-propanol.The analytical GC/MS system used was Agilent 7890A GC coupledto 5975C Mass detector Agilent Technologies, equipped with a HP-5MScapillary column (30m×0.25mm×0.25 mum). An AgilentTechnologies 7693 auto sampler was used to inject 1 muL of a solutionsample. The ionization energy was 70 eV with a mass range of 30 to800 m/z. The initial temperature of the column was set at 80 C, held for2 min, and then a ramp of 10 C/min to 250 C. The temperature of theinjector was set at 250 C and the detector at 230 C. The flow rate ofthe carrier gas (He) was 1.0 mL/min injected with a gas dilution of1:50. Identification of the individual components was based on comparisonwith the mass spectra library (NIST98).
	With lithium aluminium tetrahydride;Inert atmosphere;	General procedure: All reactions were carried out using Schlenk techniques. Proline derived ligands 3a-3c and 3e-k were prepared from Boc-L-proline and the corresponding commercially available amines, as described in the literature[i]. [RuCl2 (p-cymene)]2 and (1R,2S)-(+)-cis-1-amino-indanol 3d were purchased. Racemic alcohols 2a-m were prepared by LiAlH4 reductions of the corresponding ketone. Other reagents are commercially available. Products were purified by preparative thin layer chromatography using plates prepared from silica gel. Bruker AM 250 spectrometer, operating at 250 MHz for 1H, and at 62.5 MHz for 13C, was used for the NMR spectra which are referenced to the solvent as internal standard. Infrared spectra were recorded in CHCl3 solution using CaF2 cells on a Perkin-Elmer 1000 FT-IR spectrometer. HRMS were measured with a Thermo-Finnigan-Mat 95 spectrometer. Optical rotations were determined using a Perkin-Elmer 241 Polarimeter at room temperature using a cell of 1 dm length and l = 589 nm. Data are reported as follows: [a]D20 (concentration in g/100 mL, solvent). Reactions were monitored by gas chromatography analysis on apparatus Fisons 8000 equipped with column beta-P1. Enantiomeric excesses of alcohols were determined by gas chromatograph analysis on Fisons 9000 apparatus equipped with Chiraldex beta-PM column. For the separation of the enantiomers of the mixture of alcohols 2a-g, the program was as follows: oven temperature was maintained at 50C during 30 min, then heated to 100C (5C/min) maintained at 100C during 65 min, then heated to 120C (5C/min) and maintained at 120C during 100 min.
	With sodium tetrahydroborate; In methanol; at -10 - 25℃; for 2.33h;	Comparative Example 1 Production of 4-(2,2-dimethylcyclopropyl)butan-2-ol (may referred to as Compound (XX) in the present specification) After methyl heptenone (6.3 g, 0.050) mol) and methanol (50 mL) were added to a flask and cooled to -10 C., sodium borohydride (1.0 g, 0.025 mol) was added in portions to the reaction mixture over 20 minutes. After stirring for two hours, the reaction solution was brought to 25 C. and an aqueous sulfuric acid solution was added thereto, which then was stirred for 20 minutes. Thereafter, an aqueous sodium hydroxide solution was added to the reaction mixture. After the pH of the reaction mixture was confirmed to be 6 to 7 using pH test paper, methanol was evaporated to dryness. Diethyl ether and saturated brine were added thereto and mixed therewith and then the aqueous layer and the organic layer were separated from each other. After diethyl methyl ether was added to and mixed with the aqueous layer, the aqueous layer and the organic layer were separated from each other again. Saturated brine was added to and mixed with the organic layer and then the aqueous layer was removed. The diethyl ether was evaporated to dryness from the organic layer and thereby 5.8 g of delta-methylhept-5-en-2-ol (Compound (XXI)) (purity 97%) was obtained in a crude yield of 88

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[15]Angewandte Chemie - International Edition,2016,vol. 55,p. 11806 - 11809
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[16]Organic Magnetic Resonance,1983,vol. 21,p. 94 - 107
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[39]Journal of the Chemical Society. Perkin transactions I,1979,p. 1407 - 1410
[40]Journal of Organic Chemistry,1979,vol. 44,p. 3888 - 3901
[41]Tetrahedron Letters,1982,vol. 23,p. 2143 - 2146
[42]Tetrahedron Letters,1989,vol. 30,p. 7389 - 7392
[43]Journal of Organic Chemistry,1984,vol. 49,p. 1751 - 1761
[44]Canadian Journal of Chemistry,1980,vol. 58,p. 458 - 462
[45]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 1721 - 1726
[46]Journal of general chemistry of the USSR,1962,vol. 32,p. 2181 - 2484
    Zhurnal Obshchei Khimii,1962,vol. 32,p. 2214 - 2217
[47]Tetrahedron Letters,2011,vol. 52,p. 1485 - 1489
[48]Organometallics,2011,vol. 30,p. 5793 - 5802
[49]Organometallics,2012,vol. 31,p. 6868 - 6879
[50]Chemical Communications,2013,vol. 49,p. 400 - 402
[51]Monatshefte fur Chemie,2013,vol. 144,p. 851 - 858
[52]Journal of the American Chemical Society,2016,vol. 138,p. 8781 - 8788
[53]Applied Organometallic Chemistry,2018,vol. 32
[54]Patent: US2019/55179,2019,A1 .Location in patent: Paragraph 0120; 0121
[55]ChemCatChem,2019,vol. 11,p. 5232 - 5235

6
[ 110-93-0 ]
[ 626-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	With water; ozone
	With ozone ueber mehrere Stufen;
	With acetic acid ester; ozone at -25℃; Hydrieren des Ozonids an Palladium-Calciumcarbonat in der Kaelte;

	With tetrachloromethane; ozone Darstellung;
	With ozone; triphenylphosphine Multistep reaction;
	With ozone In dichloromethane at -78℃; for 2.5h;
	Multi-step reaction with 2 steps 1: aq. KMnO₄ 2: Pb(OAc)4, K₂CO₃ / diethyl ether

Reference： [1]Harries [Chemische Berichte, 1903, vol. 36, p. 1936]
[2]Harries; Langheld [Justus Liebigs Annalen der Chemie, 1905, vol. 343, p. 347] Harries; Boegemann [Chemische Berichte, 1909, vol. 42, p. 439]
[3]Fischer; Duell; Ertel [Chemische Berichte, 1932, vol. 65, p. 1471]
[4]Harries; Langheld [Justus Liebigs Annalen der Chemie, 1905, vol. 343, p. 347] Harries; Tuerk [Justus Liebigs Annalen der Chemie, 1910, vol. 374, p. 343]
[5]Dumas, Franoise; D'Angelo, Jean [Tetrahedron Letters, 1992, vol. 33, # 15, p. 2005 - 2008]
[6]Hodgson, David M.; Bailey, James M.; Villalonga-Barber, Carolina; Drew, Michael G. B.; Harrison, Timothy [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 20, p. 3432 - 3443]
[7]Vlad,L.A. et al. [Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, # 10, p. 2008 - 2011][Zhurnal Organicheskoi Khimii, 1970, vol. 6, # 10, p. 1999 - 2002]

7
[ 110-93-0 ]
[ 928-68-7 ]

Yield	Reaction Conditions	Operation in experiment
97.3%	With hydrogen;palladium/alumina; at 60℃; under 1500.15 Torr; for 66h;Autoclave;Product distribution / selectivity;	Step aExamples 1 to 7A 125 mL-autoclave (Hastelloy) was charged with 30 g of MH with a purity of 96.7% and the catalyst as given in table 1. The amount of catalyst was 33.3 mg in all examples. The mixture was heated to 60 C. and hydrogen was added at 2 bar. After reaction, when no up-take of hydrogen was observed any more, the mixture was cooled to 20 C., the catalyst separated by filtration and the mixture analyzed by gas chromatography.
57%	With [Ir(1-(1?-methylpyrazole)-3-(4?-methylphenyl)triazenide)Cp*Cl]; isopropyl alcohol; at 90℃; for 1.33h;Inert atmosphere; Glovebox;Catalytic behavior;	General procedure: In the glovebox, ketone or alken-2-one (6.3×10-5 mol), 1,3,5-trimethylbenzene(2 muL) as internal standard and 0.7 mL of 2-propanol-d8were transferred into a J. Young NMR tube, and a 1H NMR spectrum wasrecorded. The tube was brought back into the glovebox, and precatalyst2 (1.26×10-6 mol in 0.2 mL of 2-propanol-d8) was added. At this point,KOH (0.5 M, 5 muL, 2 eq.) in 2-propanol-d8 was added only to those catalyticreactions performed in presence of base. Outside of the gloveboxthe tube was placed inside an oil bath at 90 C. The tube was removedfrom the oil bath at different times, and 1H NMR spectra were recordedin order to follow the progress of the reaction. The conversions weredetermined by the integration of either the aromatic protons or the aliphaticprotons of the ketone. The value of the integral for the singlet dueto the aromatic protons of 1,3,5-trimethylbenzene (internal standard)was set to 10 units. In addition, the conversion was also determined byGC-MS analysis in order to follow the deuteration process of the substrates,which is a consequence of using 2-propanol-d8. In addition, thetransfer hydrogenation reactions of some aryl- alkylketones and 5-alken-2-ones were performed as above using the same quantities of reactants(precatalyst 2 or 3 and KOH if needed) in regular 2-propanol.The analytical GC/MS system used was Agilent 7890A GC coupledto 5975C Mass detector Agilent Technologies, equipped with a HP-5MScapillary column (30m×0.25mm×0.25 mum). An AgilentTechnologies 7693 auto sampler was used to inject 1 muL of a solutionsample. The ionization energy was 70 eV with a mass range of 30 to800 m/z. The initial temperature of the column was set at 80 C, held for2 min, and then a ramp of 10 C/min to 250 C. The temperature of theinjector was set at 250 C and the detector at 230 C. The flow rate ofthe carrier gas (He) was 1.0 mL/min injected with a gas dilution of1:50. Identification of the individual components was based on comparisonwith the mass spectra library (NIST98).

Reference： [1]Tetrahedron,1981,vol. 37,p. 3009 - 3016
[2]Patent: US2012/53353,2012,A1 .Location in patent: Page/Page column 4
[3]Journal of Natural Products,2000,vol. 63,p. 666 - 669
[4]Monatshefte fur Chemie,1994,vol. 125,p. 1159 - 1170
[5]Journal of Organic Chemistry,2017,vol. 82,p. 211 - 233
[6]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 1720 - 1723
[7]Archiv der Pharmazie,1996,vol. 329,p. 27 - 34
[8]Inorganica Chimica Acta,2020,vol. 507
[9]ChemCatChem,2017,vol. 9,p. 432 - 439
[10]Journal of the Chemical Society,1948,p. 48
[11]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1905,vol. 140,p. 152
[12]Recherches,1957,p. 29,35
Recherches,1960,p. 18,19
[13]Acta Chemica Scandinavica,1975,vol. 29,p. 1015 - 1023
[14]Journal of Organic Chemistry,1977,vol. 42,p. 1709 - 1717
[15]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 5214 - 5224
[16]Justus Liebigs Annalen der Chemie,1915,vol. 408,p. 172
[17]Journal of Organic Chemistry,2006,vol. 71,p. 5864 - 5869
[18]Synlett,2006,p. 721 - 724
[19]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1962,vol. 255,p. 1621 - 1622
[20]Journal of the American Chemical Society,2016,vol. 138,p. 12234 - 12242
[21]Chemistry - A European Journal,2018,vol. 24,p. 2457 - 2465
[22]Catalysis Today,2018,vol. 308,p. 38 - 44
[23]Patent: US2018/361370,2018,A1 .Location in patent: Paragraph 0338
[24]Organometallics,2019,vol. 38,p. 844 - 851

8
[ 110-93-0 ]
[ 105-36-2 ]
[ 54211-39-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With zinc; In tetrahydrofuran; for 2h;Reflux;	General procedure: 2-Methyl-2-hepten-6-one (3.16 g, 25.0 mol) and BrCH2COOCH3 (7.65 g, 50.0 mol) in 50 mL of anhydrous THF were added to a suspension of Zn (3.27 g, 50.0 mol) in anhydrous THF (50 mL) at reflux. After the reaction was initiated, the other portion of the solution was added dropwise to the reaction mixture. The mixture was allowed to stir at reflux until the color of the Zn changed from gray to brownish. After 2 h, the reaction mixture was cooled to room temperature, and the reaction was quenched with 100 mL of 10% AcOH. The reaction mixture was extracted with EtOAc (3 × 100 mL). The combined organic layers were washed with brine and dried with anhydrous Na2SO4. The solvent was evaporated in vacuo, and the crude product was purified by column chromatography (EtOAc-petroleum ether, 1:7) to yield 2a (4.25 g, 85%) as a pale yellow oil; Rf 0.32 (EtOAc-petroleum ether, 1:7); 1H NMR (500 MHz, CDCl3) delta 5.07 (t, J = 6.3 Hz, 1H, CH2CH=), 3.69 (s, 3H, OCH3), 3.08 (s, 1H, OH), 2.51 (d, J = 15.5 Hz, 1H, CH2COOCH3), 2.43 (d, J = 15.5 Hz, 1H, CH2COOCH3), 2.02 (m, 2H, =CHCH2), 1.66 (s, 3H, CH3), 1.59 (s, 3H, CH3), 1.52 (m, 2H, =CHCH2CH2), 1.22 (s, 3H, COHCH3); 13C NMR (125 MHz, CDCl3) delta 173.4, 131.9, 124.2, 71.0, 51.7, 44.9, 41.9, 26.8, 25.7, 22.8, 17.7; HRESIMS m/z 201.1486 [M + H]+ (calcd. for C11H21O3, 201.1485).
95%	With zinc; In tetrahydrofuran; for 2h;Reflux;	1.47 g (22.5 mmol) of Zn powder was dissolved in a dry solution of 50 mL of THF,Heated to reflux. (15 mmol) of methylheptenone and 3.76 g (22.5 mmol) of ethyl bromoacetate were dissolved in a dry 20 mL THF solution,Was slowly added dropwise to a refluxing suspension of zinc powder in THF,The reflux reaction was continued, Until the color of zinc powder from gray to brown,The reaction solution turned green (about 2 h).After completion of the reaction, the reaction solution was cooled to room temperature and the reaction was quenched with 100 mL of 10%The solution turned yellow and transparent, zinc powder dissolved. The reaction mixture was diluted with ethyl acetate and the aqueous layer was extracted twice with EtOAc (100 mL each)The layers were dried over anhydrous MgSO4, concentrated by filtration, purified by silica gel column chromatography, eluted with ethyl acetate and petroleum ether (volume ratio1: 7) to give 3.05 g of compound 4 as a pale yellow oil in 95.0% yield. Rf 0.3 (ethyl acetate: petroleum ether, 1: 7 (v / v)). OfCompound 4
95%	With zinc; In tetrahydrofuran; for 2h;Reflux;	1.47 g (22.5 mmol) of Zn powder was dissolved in a dry 50 mL THF solution and heated to reflux. A solution of 1.89 g (15 mmol) of 6-methylhept-5-en-2-one and 3.76 g (22.5 mmol) of ethyl bromoacetate in a dry solution of 20 mL THF was slowly added dropwise to a refluxing suspension of zinc powder in THF Solution. The reaction was continued until the zinc color changed from gray to brown, and the reaction solution turned green (about 2 h). After the reaction was completed, the reaction solution was cooled to room temperature and the reaction was quenched with 100 mL of 10% AcOH. The solution became yellow and transparent, and the zinc powder was dissolved. The reaction mixture was diluted with ethyl acetate and the aqueous layer was extracted twice with EtOAc (100 mL each time). The combined organic layers were dried over anhydrous MgSO4, concentrated by filtration, purified by silica gel column chromatography, eluted with ethyl acetate and petroleum ether, (1: 7 in volume ratio) to give 3.05 g of compound 5 as a light yellow oil with a yield of 95.0%.

Reference： [1]Marine Drugs,2014,vol. 12,p. 3352 - 3370
[2]Patent: CN104803840,2016,B .Location in patent: Paragraph 0021; 0022; 0023; 0024; 0025
[3]Patent: CN104803853,2017,B .Location in patent: Paragraph 0032; 0033; 0034
[4]Journal of Organic Chemistry,1983,vol. 48,p. 4108 - 4111
[5]Chemische Berichte,1898,vol. 31,p. 827
[6]Helvetica Chimica Acta,1940,vol. 23,p. 965
[7]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 588 - 600
[8]Tetrahedron Asymmetry,1996,vol. 7,p. 2023 - 2028

9
[ 110-93-0 ]
[ 74-89-5 ]
[ 503-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	Hydrogenation;
	Electrolysis;
	With hydrogen

	Electrolysis;
	Hydrogenation;
	With hydrogen

Reference： [1]Current Patent Assignee: ABBVIE INC - AT134561, B
[2]Current Patent Assignee: ABBVIE INC - AT134561, B
[3]Current Patent Assignee: ABBVIE INC - AT134561, B
[4]Current Patent Assignee: ABBVIE INC; WILFRID KLAVEHN DR - DE617536, 1931, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 681][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 681] Current Patent Assignee: ABBVIE INC - CH163535, 1933, A Current Patent Assignee: BILHUBER E - US1972450, 1931, A Current Patent Assignee: ABBVIE INC; LONZA GROUP AG; WILFRID KLAVEHN DR - DE617879, 1932, C
[5]Current Patent Assignee: ABBVIE INC; WILFRID KLAVEHN DR - DE617536, 1931, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 681][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 681] Current Patent Assignee: ABBVIE INC - CH163535, 1933, A Current Patent Assignee: BILHUBER E - US1972450, 1931, A Current Patent Assignee: ABBVIE INC; LONZA GROUP AG; WILFRID KLAVEHN DR - DE617879, 1932, C
[6]Current Patent Assignee: ABBVIE INC; WILFRID KLAVEHN DR - DE617536, 1931, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 681][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 681] Current Patent Assignee: ABBVIE INC - CH163535, 1933, A Current Patent Assignee: BILHUBER E - US1972450, 1931, A Current Patent Assignee: ABBVIE INC; LONZA GROUP AG; WILFRID KLAVEHN DR - DE617879, 1932, C

10
[ 110-93-0 ]
[ 74-86-2 ]
[ 29171-20-8 ]

Yield	Reaction Conditions	Operation in experiment
99.1%	With sodium methylate; In methanol; at 0 - 5℃; for 0.5h;Inert atmosphere;	General procedure: In a 10 L three-necked flask, 6 L of anhydrous methanol was added, and the mixture was shielded with nitrogen. Under cooling with ice water, 550 g of sodium metal (small) was slowly added.After all the sodium metal was dissolved, 1.5 L of acetone was added, and the mixture was uniformly stirred and cooled to below 0 C. Slowly pass acetylene, The flow rate of the acetylene is controlled so that the reaction temperature is 0 to 5 C. When the reaction is no longer exothermic, the reaction is complete. Then, a small amount of acetylene was introduced, and the closed micro-positive pressure (nitrogen balloon was not changed) was reacted for 0.5 hour. In another 20 L three-necked flask, 2.5 kg of ammonium chloride and 3 L of methanol were added.Under ice cooling, the reaction solution was poured into an ammonium chloride system to carry out a neutralization reaction. The neutralization reaction temperature was controlled to be less than 20 C. After the neutralization is completed, it is filtered. The filtrate was first distilled with methanol, methanol was applied, and then the product methylbutynol was distilled under reduced pressure to obtain 1.69 kg. The product purity was 99.5%, and the yield was 99.1%.
98.52%Chromat.	With sodium cyanide; In N,N-dimethyl-formamide; at 10℃; under 750.075 - 1125.11 Torr; for 3h;Autoclave;	First add 126g of N,N-dimethylformamide to the autoclave, 1.62 g (0.03 mol) of sodium methoxide, 0.49 g (0.01 mol) of sodium cyanide, after the autoclave was sealed, the autoclave was replaced 3 times with nitrogen, and then replaced with acetylene 3 times. The acetylene pressure does not exceed 0.15 MPa (gauge pressure). Turn on stirring and set the temperature to 10 C. Adjust the pressure of the pressure reducing valve of the acetylene gas cylinder to 0.1 MPa (gauge pressure), and pass in the acetylene gas. After the pressure in the reactor is stabilized at 0.1 MPa (gauge pressure), using a feed pump, add 126 g (1 mol) of 6-methyl-5-hepten-2-one, feeding time is controlled at 1h. Control the reaction temperature at 10 C, after 6-methyl-5-hepten-2-one feeding was completed for another 2 hours, the pressure was released to release acetylene gas. 60 g of pure water was added to the reaction solution for extraction, and the aqueous phase was retained. The organic phase was extracted by adding 30 g of pure water, and the organic phase was sampled. The two extracted aqueous phases were combined and retained. N,N-dimethylformamide, catalyst and inhibitor mainly exist in the water phase, the product alkynyl compounds mainly exist in the organic phase. The reaction was detected by GC. Organic phase reaction liquid composition: dehydrolinalool 98.52%, 6-methyl-5-hepten-2-one 0.79%, 6-methyl-5-hepten-2-one alkynediol was not detected, the other 0.69%. Conversion was 99.21%, and selectivity was 99.30%. 1200 g of cyclohexane were added to the combined aqueous phases, atmospheric azeotropic distillation dehydration, the heating temperature at the bottom of the tower was 130 C, and the azeotrope was obtained at 69 C at the top of the tower, until no more was produced at the top of the tower. 122.3 g of liquid phase was obtained at the bottom of the column, filtration to separate N,N-dimethylformamide from catalysts and inhibitors, N,N-dimethylformamide recovery was 97%.

Reference： [1]Patent: CN108863717,2018,A .Location in patent: Paragraph 0036; 0037; 0038; 0043; 0044; 0045; 0046
[2]Tetrahedron,1983,vol. 39,p. 2315 - 2322
[3]Doklady Akademii Nauk SSSR,1957,vol. 114,p. 796
Doklady Chemistry, 112-117<1957>579,
[4]Helvetica Chimica Acta,1919,vol. 2,p. 184
[5]Helvetica Chimica Acta,1929,vol. 12,p. 1140
[6]Collection of Czechoslovak Chemical Communications,1960,vol. 25,p. 1914 - 1921
[7]Patent: CN110467519,2019,A .Location in patent: Paragraph 0040-0053; 0060-0068

11
[ 110-93-0 ]
[ CAS Unavailable ]
[ 503-01-5 ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium cyanoborohydride; potassium hydroxide In methanol for 0.166667h; Inert atmosphere;
	With hydrogenchloride; potassium hydroxide; sodium cyanoborohydride In methanol

Reference： [1]Kaphan, David M.; Toste, F. Dean; Bergman, Robert G.; Raymond, Kenneth N. [Journal of the American Chemical Society, 2015, vol. 137, # 29, p. 9202 - 9205]
[2]Taylor,W.G.; Coutts,R. [Canadian Journal of Chemistry, 1979, vol. 57, p. 2103 - 2107]

12
[ 110-93-0 ]
[ 4342-60-3 ]
[ 94294-81-2 ]
[ 94294-79-8 ]

Reference： [1]Journal of the American Chemical Society,1986,vol. 108,p. 7801

13
[ 110-93-0 ]
[ 13321-74-9 ]
[ 78919-97-8 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 4666 - 4667
[2]Molecules,2011,vol. 16,p. 8053 - 8061

14
[ 110-93-0 ]
[ 71846-54-3 ]

Yield	Reaction Conditions	Operation in experiment
38%	With tert.-butylhydroperoxide; selenium(IV) oxide; In dichloromethane; water; at 20℃; for 19h;	Compound 2a (3.20 g, 15.9 mmol) was dissolved in CH2Cl2 (150 mL) and added dropwise to a solution of SeO2 (825 mg, 7.4 mmol) and t-BuOOH (70% in water, 3.2 mL, 22.3 mmol) in CH2Cl2 (50 mL) at room temperature. After stirring at room temperature for 19 h, the reaction mixture was quenched with aqueous 10% NaOH, H2O and brine; then, the organic layer was dried and concentrated. The resulting yellow oil was purified by flash column chromatography (EtOAc-petroleum ether, 1:7) on silica gel to yield 4a as a colorless oil (624 mg, 25%); Rf 0.33 (EtOAc-petroleum ether, 1:3); 1H NMR (500 MHz, CDCl3) delta 9.38 (s, 1H, CHO), 6.48 (t, J = 6.9 Hz, 1H, CH2CH=), 3.72 (s, 3H, OCH3), 2.55 (d, J = 15.7 Hz, 1H, CH2COOCH3), 2.49 (d, J = 15.7 Hz, 1H, CH2COOCH3), 2.46 (m, 2H, CH2CH2CH=), 1.75 (s, 3H, CH3), 1.67 (m, 2H, CH2CH2CH=), 1.28 (s, 3H, COHCH3); 13C NMR (125 MHz, CDCl3) delta 195.3, 173.3, 154.3, 139.6, 70.7, 51.9, 44.9, 40.2, 26.7, 23.7, 9.3; HRESIMS m/z 237.1100 [M + Na]+ (calcd. for C11H18O4Na, 237.1097). Compound 3a was obtained in an analogous fashion; colorless oil (732 mg, 29%); Rf 0.22 (EtOAc-petroleum ether, 1:3); 1H NMR (500 MHz, CDCl3) delta 5.39 (t, J = 7.1 Hz, 1H, CH2CH=), 3.98 (s, 2H, CH2OH), 3.71 (s, 3H, OCH3), 2.53 (d, J = 15.6 Hz, 1H, CH2COOCH3), 2.46 (d, J = 15.6 Hz, 1H, CH2COOCH3), 2.12 (m, 2H, CH2CH=), 1.66 (s, 3H, CH3C=), 1.56 (m, 2H, CH2CH2CH=), 1.25 (s, 3H, COHCH3); 13C NMR (125 MHz, CDCl3) delta 173.5, 135.3, 125.8, 71.0, 68.9, 51.8, 45.0, 41.6, 26.8, 22.4, 13.7; HRESIMS m/z 239.1252 [M + Na]+ (calcd. for C11H20O4Na, 239.1254). Additionally, 841 mg of material were recovered. The E-configuration of Compound 3a was verified by a NOESY correlation from CH2CH= (delta 5.39) to CH2OH (delta 3.98).

Reference： [1]Synthesis,2001,p. 393 - 398
[2]Tetrahedron Letters,2001,vol. 42,p. 275 - 277
[3]Journal of the American Chemical Society,2016,vol. 138,p. 14226 - 14229
[4]Marine Drugs,2014,vol. 12,p. 3352 - 3370
[5]Journal of the American Chemical Society,1987,vol. 109,p. 2547 - 2549
[6]Journal of Organometallic Chemistry,1994,vol. 473,p. 257 - 264

15
[ 110-93-0 ]
[ 4730-22-7 ]
[ 1569-60-4 ]
[ 928-68-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 20 % Chromat. 2: 15 % Chromat. 3: 50 % Chromat.	With hydrogen In ethanol at 25℃; for 11h;
58 %Chromat.	With C₃₄H₂₈Cl₂N₃OPRu; potassium isopropoxide; isopropyl alcohol at 82℃; for 2h; Inert atmosphere; Schlenk technique; chemoselective reaction;
	With hydrogen; sodium hydroxide In methanol; water at 30℃; for 40h; Autoclave;

	With C₂₅H₃₅ClIrN₅; potassium hydroxide In isopropyl alcohol at 70℃; for 38h; Overall yield = 96 %Spectr.;
	With C₂₅H₃₅ClN₅Rh In isopropyl alcohol at 70℃; for 6h; Overall yield = 95 %Spectr.;

Reference： [1]Gallois, Philippe; Brunet, Jean-Jaques; Caubere, Paul [Journal of Organic Chemistry, 1980, vol. 45, # 10, p. 1946 - 1950]
[2]Shi, Jing; Hu, Bowen; Gong, Dawei; Shang, Shu; Hou, Guangfeng; Chen, Dafa [Dalton Transactions, 2016, vol. 45, # 11, p. 4828 - 4834]
[3]Forato, Florian; Belhboub, Anouar; Monot, Julien; Petit, Marc; Benoit, Roland; Sarou-Kanian, Vincent; Fayon, Franck; Jacquemin, Denis; Queffelec, Clémence; Bujoli, Bruno [Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2457 - 2465]
[4]Camarena-Diáz, Juan P.; Iglesias, Ana L.; Chávez, Daniel; Aguirre, Gerardo; Grotjahn, Douglas B.; Rheingold, Arnold L.; Parra-Hake, Miguel; Miranda-Soto, Valentín [Organometallics, 2019, vol. 38, # 4, p. 844 - 851]
[5]Camarena-Diáz, Juan P.; Iglesias, Ana L.; Chávez, Daniel; Aguirre, Gerardo; Grotjahn, Douglas B.; Rheingold, Arnold L.; Parra-Hake, Miguel; Miranda-Soto, Valentín [Organometallics, 2019, vol. 38, # 4, p. 844 - 851]

16
[ 110-93-0 ]
[ 4730-22-7 ]
[ 928-68-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 87% 2: 13%	With [Ir(1-(1′-methylpyrazole)-3-(4′-methylphenyl)triazenide)Cp*Cl]; isopropyl alcohol at 90℃; for 23h; Inert atmosphere; Glovebox; Overall yield = 100 percent;	2.5. General procedure for transfer hydrogenation reactions monitored by1H NMR and gas chromatography mass spectrometry (GC-MS) General procedure: In the glovebox, ketone or alken-2-one (6.3×10-5 mol), 1,3,5-trimethylbenzene(2 μL) as internal standard and 0.7 mL of 2-propanol-d8were transferred into a J. Young NMR tube, and a 1H NMR spectrum wasrecorded. The tube was brought back into the glovebox, and precatalyst2 (1.26×10-6 mol in 0.2 mL of 2-propanol-d8) was added. At this point,KOH (0.5 M, 5 μL, 2 eq.) in 2-propanol-d8 was added only to those catalyticreactions performed in presence of base. Outside of the gloveboxthe tube was placed inside an oil bath at 90 °C. The tube was removedfrom the oil bath at different times, and 1H NMR spectra were recordedin order to follow the progress of the reaction. The conversions weredetermined by the integration of either the aromatic protons or the aliphaticprotons of the ketone. The value of the integral for the singlet dueto the aromatic protons of 1,3,5-trimethylbenzene (internal standard)was set to 10 units. In addition, the conversion was also determined byGC-MS analysis in order to follow the deuteration process of the substrates,which is a consequence of using 2-propanol-d8. In addition, thetransfer hydrogenation reactions of some aryl- alkylketones and 5-alken-2-ones were performed as above using the same quantities of reactants(precatalyst 2 or 3 and KOH if needed) in regular 2-propanol.The analytical GC/MS system used was Agilent 7890A GC coupledto 5975C Mass detector Agilent Technologies, equipped with a HP-5MScapillary column (30m×0.25mm×0.25 μm). An AgilentTechnologies 7693 auto sampler was used to inject 1 μL of a solutionsample. The ionization energy was 70 eV with a mass range of 30 to800 m/z. The initial temperature of the column was set at 80 °C, held for2 min, and then a ramp of 10 °C/min to 250 °C. The temperature of theinjector was set at 250 °C and the detector at 230 °C. The flow rate ofthe carrier gas (He) was 1.0 mL/min injected with a gas dilution of1:50. Identification of the individual components was based on comparisonwith the mass spectra library (NIST98).
1: 7.4% 2: 19.6%	With hydrogen In diethylene glycol dimethyl ether; water at 30℃; for 4.5h;
	With bis[1-butyl-2-(diphenylphosphanyl)-3-methylimidazolium]tetrachloridoruthenium(III) hexafluorophosphate; potassium <i>tert</i>-butylate; isopropyl alcohol at 100℃; for 2h; Inert atmosphere; Autoclave;

	With hydrogen; sodium hydroxide In methanol; water at 30℃; for 40h; Autoclave;
	With C₂₅H₃₅ClIrN₅ In isopropyl alcohol at 70℃; for 6h; Overall yield = 100 %Spectr.;
	With water In ethanol at 65℃; for 5h; Flow reactor;

Reference： [1]Medrano-Castillo, Layla J.; Collazo-Flores, Miguel Á.; Camarena-Díaz, Juan P.; Correa-Ayala, Erick; Chávez, Daniel; Grotjahn, Douglas B.; Rheingold, Arnold L.; Miranda-Soto, Valentín; Parra-Hake, Miguel [Inorganica Chimica Acta, 2020, vol. 507]
[2]Fujitsu, Hiroshi; Matsumura, Eiichi; Takeshita, Kenjiro; Mochida, Isao [Journal of the Chemical Society. Perkin transactions I, 1981, p. 2650 - 2655]
[3]Location in patent: experimental part Zhou, Chengliang; Zhang, Jing; Dakovic, Marijana; Popovic, Zora; Zhao, Xiaoli; Liu, Ye [European Journal of Inorganic Chemistry, 2012, # 21, p. 3435 - 3440]
[4]Forato, Florian; Belhboub, Anouar; Monot, Julien; Petit, Marc; Benoit, Roland; Sarou-Kanian, Vincent; Fayon, Franck; Jacquemin, Denis; Queffelec, Clémence; Bujoli, Bruno [Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2457 - 2465]
[5]Camarena-Diáz, Juan P.; Iglesias, Ana L.; Chávez, Daniel; Aguirre, Gerardo; Grotjahn, Douglas B.; Rheingold, Arnold L.; Parra-Hake, Miguel; Miranda-Soto, Valentín [Organometallics, 2019, vol. 38, # 4, p. 844 - 851]
[6]Zienkiewicz-Machnik, Małgorzata; Goszewska, Ilona; Giziński, Damian; Śrębowata, Anna; Kuzmowicz, Katarzyna; Kubas, Adam; Matus, Krzysztof; Lisovytskiy, Dmytro; Pisarek, Marcin; Jacinto [ChemCatChem, 2020, vol. 12, # 11, p. 3132 - 3138]

17
[ 502-65-8 ]
[ 110-93-0 ]
[ 22255-36-3 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 1718 - 1719
[2]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 1718 - 1719

18
[ 110-93-0 ]
[ 145100-50-1 ]
[ 180303-11-1 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 1582 - 1583

19
[ 626-96-0 ]
[ 24470-78-8 ]
[ 110-93-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With n-butyllithium In tetrahydrofuran at -78 - 20℃;

Reference： [1]Kerrigan, Nessan J.; Upadhyay, Tejas; Procter, David J. [Tetrahedron Letters, 2004, vol. 45, # 49, p. 9087 - 9090]

20
[ 110-93-0 ]
zinc [ No CAS ]
[ 488-10-8 ]

Reference： [1]Synthetic Communications,1985,vol. 15,p. 1147 - 1152

21
[ 110-93-0 ]
[ 2051-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: NaNH₂; Na₂SO₄; diethyl ether / Reagens 4: Benzol 2: diethyl ether 3: PBr₃; pyridine; petroleum ether / Schuetteln des entstandenen Bromids mit Kaliumacetat in Aceton und Verseifen des entstandenen Acetats mit methylalkoholischer KOH 4: PtO₂; acetic acid ester / Hydrogenation_.zuletzt in Eisessig

Reference： [1]Schinz; Bourquin [Helvetica Chimica Acta, 1942, vol. 25, p. 1610]

22
[ 110-93-0 ]
[ 78-69-3 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1908,vol. 27,p. 415

23
[ 110-93-0 ]
[ 13837-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium amide 2: beim Kochen
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 2: C-undecyl resorcin[4]arene / chloroform-d1 / 43.2 h / 0 - 30 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / -78 - 20 °C 2: Amberlyst(R) 15 / dichloromethane / 6 h / Reflux

Reference： [1]Rupe; Lang [Helvetica Chimica Acta, 1929, vol. 12, p. 1140]
[2]Catti; Tiefenbacher [Chemical Communications, 2015, vol. 51, # 5, p. 892 - 894]
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/5901, 2015, A1

24
[ 110-93-0 ]
[ 40607-48-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Pd-BaSO₄ 2: (i) NaH, (ii) /BRN= 635835/, (iii) LiAlH₄

Reference： [1]Eidem; Buchecker; Kjosen; Liaaen Jensen [Acta Chemica Scandinavica, 1975, vol. 29, # 10 B, p. 1015 - 1023]

25
cupric chloride [ No CAS ]
C₂ H₅ O(C₂ H₄ O)18 CH₃ [ No CAS ]
[ 7270-50-0 ]
[ 7647-10-1 ]
[ 110-93-0 ]

Yield	Reaction Conditions	Operation in experiment
	In water;	EXAMPLE 8 Into the same reaction apparatus as in Example 1 was added distilled water (55 g), C2 H5 O(C2 H4 O)18 CH3 (45 g), <strong>[7647-10-1]palladous chloride</strong> (7.5 mmol) and cupric chloride (15 mmol) and the resultant mixture was heated to 70 C. under stirring. When the inner temperature became constant at 70 C., 6-methyl-1,5-heptadiene (10 ml) (67.5 mmol) was added while introducing air at a rate of 5 l/hr to the mixture. The reaction was continued for 1.5 hour under vigorous stirring. Yield of 6-methyl-5-hepten-2-one was 28 mmol.

Reference： [1]Patent: US4271320,1981,A

26
[ 110-93-0 ]
Cooling-agent 10 [ No CAS ]
[ 1189585-42-9 ]

Yield	Reaction Conditions	Operation in experiment
92.6%		100.0 g of 1-menthoxypropanediol (molecular weight: 230.35, 434.1 mmol) , 54.8 g of methylheptenone (molecular weight: 126.20, 434.1 mmol), 1.0 g p-toluenesulfonic acid monohydrate (molecular weight: 190.22, 5.2 mmol), and 300 ml of toluene were placed in a 1-L reaction flask equipped with a thermometer, a Dean-Stark trap, and a reflux condenser. The mixture was heated at an oil bath temperature of 1400C and additionally under reflux for two hours while water generated during reflux was removed. The reaction solution obtained after cooling was quenched in aqueous sodium carbonate solution and extracted with toluene. The toluene phase was washed with aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and condensed in rotary evaporator for removal of the solvent to give pale yellow oil. Distillation thereof under reduced pressure gave a desired product, 1-menthoxypropanediol methylheptenone ketal as colorless oil. Yield: 136.1 g, (molecular weight: 338.54, 402.0 mmol), purity: 100%, yield: 92.6%, boiling point: 110 to 111C (10 Pa) .1HNMR (500MHz, CDCl3, delta) ppm: 0.73-0.80 (m,3H), 0.74-1.06 <n="113"/>(m,3.5H), 0.84-0.94 (m, 6H), 1.16-1.28 (m, IH), 1.26-1.42 (m, IH), 1.31 (s, 1.5H), 1.31 (s, 1.5H), 1.36 (s, 1.5H), 1.52-1.75 (m, 3.5H), 1.61 (s, 3H), 1.68 (s, 3 H), 1.97-2.12 (m, 3H), 2.12-2.24 (m, IH), 3.00-3.12 (m, IH), 3.20-3.27 (m, 0.5H), 3.41-3.48 (m, 0.5H), 3.51-3.57 (m, 0.5H), 3.63-3.72 (m, 0.5H), 3.71-3.78 (m, IH), 4.03-4.11 (m, IH), 4.15-4.22 (m, 0.5H), 4.-22-4.29 (m, 0.5H), 5.07-5.16 (m, IH).IR (NaCl) cm"1: 2954, 2923, 2869, 1453, 1375, 1342, 1239, 1201, 1182, 1109, 1074, 1054, 919, 876, 844.MS (m/z) : 338, 323, 281, 267, 255, 231, 213, 199, 185, 169, 155, 139, 108, 97, 83, 69, 57, 55, 43, 41.

Reference： [1]Patent: WO2009/123355,2009,A2 .Location in patent: Page/Page column 109-111

27
[ 502-65-8 ]
[ 141-27-5 ]
[ 110-93-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 9951 - 9955

28
[ 110-93-0 ]
[ 57009-12-8 ]
[ 1326774-90-6 ]

Yield	Reaction Conditions	Operation in experiment
56%		A solution of LDA was prepared by adding a 2.7 M solution of n-BuLi in heptane (0.595 mL, 1.61 mmol) to a solution of diisopropylamine (0.227 mL, 1.61 mmol) in 4 mL of THF, stirring at 0 C under argon atmosphere. After 30 min, the solution was cooled to -78 C and added slowly with a solution of <strong>[57009-12-8]3-acetyl-4-hydroxybenzoic acid methyl ester</strong> (3) (0.125 g, 0.64 mmol) in THF (1 mL) over 10 min. The resulting solution was stirred for 1 h at -78 C (in order to secure the complete formation of the corresponding enolate) prior to slow addition of 6-methyl-5-hepten-2-one (0.143 mL, 0.97 mmol). Stirring was continued for 3 h at -78 C and then the reaction was quenched with a saturated aqueous NH4Cl solution. The reaction mixture was allowed to reach room temperature. The layers were separated and the aqueous layer was extracted with diethyl ether (3×5 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography (ethyl acetate/hexane 15:85) to afford the aldol product 4 as a viscous oil (0.115 g, 56%). [Found: C, 67.45; H, 7.52. C18H24O5 requires C, 67.48; H, 7.55]; Rf 0.74 (ethyl acetate/hexane 1:1); IR numax (liquid film) 3510, 3080, 2950, 2850, 1720, 1640, 1590, 1480, 1440, 1380, 1280, 1230, 1120, 980, 780 cm-1; 1H NMR (300 MHz, CDCl3) delta: 12.61 (s, 1H), 8.50 (d, J 2.2 Hz, 1H), 8.18 (dd, J 2.2, 8.8 Hz, 1H), 7.02 (d, J 8.8 Hz, 1H), 5.06 (m, 1H), 3.95 (s, 1H), 3.30 (d, J 16.6 Hz, 1H), 3.20 (d, J 16.6 Hz, 1H), 2.10 (m, 2H), 1.80-1.55 (m, 8H), 1.35 (s, 3H); 13C NMR (75 MHz, CDCl3) delta: 207.2, 166.0, 165.6, 137.3, 132.6, 131.9, 123.7, 120.9, 119.2, 118.8, 72.0, 52.0, 46.8, 41.8, 26.9, 25.4, 22.5, 17.4. HRMS (ESI+) calcd for C18H24O5Na+343.15159, found 343.15882.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6300 - 6307
[2]Chemistry and biodiversity,2012,vol. 9,p. 41 - 47

29
[ 110-93-0 ]
[ 67868-73-9 ]
[ 113706-59-5 ]

Reference： [1]Molecules,2011,vol. 16,p. 8053 - 8061

30
[ 497-06-3 ]
[ 110-93-0 ]
[ 1411949-48-8 ]

Yield	Reaction Conditions	Operation in experiment
78%		9 Synthesis of 2-methyl-2-(4-methylpent-3-enyl)-4-vinyl-[1,3]dioxolane EXAMPLE 9 Synthesis of 2-methyl-2-(4-methylpent-3-enyl)-4-vinyl-[1,3]dioxolane 2-methyl-2-(4-methylpent-3-enyl)-4-vinyl-[1,3]dioxolane was synthesized by analogy to Example 2, starting with 20.0 g 1-butene-3,4-diol and 28.6 g 6-methylhept-5-en-2-one. 36.5 g 2-methyl-2-(4-methylpent-3-enyl)-4-vinyl-[1,3]dioxolane with a purity of 96% were isolated (2 isomers in the ratio 1:1). This corresponds to a yield of 78% of theoretical. Boiling point: 80° C./1.4 mbar.-MS: m/z (%)=196 (M+, 2), 125 (4), 113 (30), 108 (4), 93 (3), 83 (5), 69 (14), 55 (8), 43 (100), 27 (5).-1H NMR (400 MHz, CDC3): δ (ppm)=1.35 (s, 3H), 1.38 (s, 3H), 1.60-1.63 (m, 6H), 1.67-1.69 (m, 6H), 2.14-2.3 (m, 8H), 3.55 (t, J=8.0 Hz, 1H), 3.61 (t, J=8.1 Hz, 1H), 4.11 (dd, J=8.0, 6.2 Hz, 1H), 4.12 (dd, J=8.1, 6.2 Hz, 1H), 4.46 (ddd, J=8.1, 6.2, 1.0 Hz, 1H), 4.53 (ddd, J=8.1, 6.2, 1.0 Hz, 1H), 5.07-5.15 (m, 2H), 5.21 (ddd, J=10.3, 1.5, 0.8 Hz, 1H), 5.22 (ddd, J=10.3, 1.5, 0.9 Hz, 1H), 5.35 (ddd, J=17.1, 1.4, 1.0 Hz, 1H), 5.36 (ddd, J=17.1, 1.4, 1.0 Hz, 1H), 5.83 (ddd, J=17.1, 10.2, 7.1 Hz, 1H), 5.83 (ddd, J=17.1, 10.3, 7.1 Hz, 1H).-13C NMR (100 MHz, CDCl3): δ (ppm)=17.6 (2CH3), 22.7 (CH2), 22.8 (CH2), 24.2 (CH3), 24.8 (CH3), 25.7 (2CH3), 39.3 (CH2), 39.8 (CH2), 69.3 (CH2), 69.6 (CH2), 77.2 (CH), 77.9 (CH), 110.8 (Cquart.), 110.9 (Cquart.), 118.1 (2*CH2), 124.0 (CH), 124.1 (CH), 131.6 (Cquart.), 131.7 (Cquart.), 135.6 (CH), 136.1 (CH).

Reference： [1]Current Patent Assignee: SYMRISE AG - US2012/308486, 2012, A1

31
[ 1569-60-4 ]
[ 110-93-0 ]
[ 10408-15-8 ]
[ 928-68-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 80% 2: 15% 3: 5%	With reusable unsupported rhenium nanocrystalline particle In neat (no solvent) at 180℃; for 10h; Green chemistry;

Reference： [1]Yi, Jing; Miller, Jeffrey T.; Zemlyanov, Dmitry Y.; Zhang, Ruihong; Dietrich, Paul J.; Ribeiro, Fabio H.; Suslov, Sergey; Abu-Omar, Mahdi M. [Angewandte Chemie - International Edition, 2014, vol. 53, # 3, p. 833 - 836][Angew. Chem., 2013, vol. 126, # 03, p. 852 - 855]

32
[ 110-93-0 ]
[ 373-88-6 ]
6-methyl-N-(2,2,2-trifluoroethyl)hept-5-en-2-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 9202 - 9205

33
[ 95-20-5 ]
[ 110-93-0 ]
[ 50910-55-9 ]
9,11-dibromo-6-methyl-6-(4-methylpent-3-en-1-yl)-6,7-dihydro-5H-benzo[6,7]azepino[4,5-b]quinolone [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 364 - 367

34
[ 106-72-9 ]
[ 110-93-0 ]
trans-2-(1-methylethenyl)-5-methylcyclopentanol [ No CAS ]
cis-2-(1-methylethenyl)-5-methylcyclopentanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromo-triphenyl-methane In dichloromethane at 20℃; Inert atmosphere; Overall yield = 46 %;	General Procedure for the High-Pressure-Promoted Reaction of Unsaturated Carbonyl Compounds or Activated Dienes General procedure: All high-pressure reactions were performed in a Hikari-KoatsuHR-15-B3 apparatus, which is designed for pressures up to 1.0GPa. A mixture of aldehyde or diene (0.2 mmol), thiourea (TU,10 mg, 0.02 mmol), and trityl bromide (I, 6.5 mg, 0.02 mmol) in anhydrous CH2Cl2 (2 mL) was reacted at 1.0 GPa and at r.t. for the period shown in Tables 2 and 3. After releasing the pressure,the mixture was concentrated in vacuo, and the residue was purified by column chromatography (eluted with hexane-Et2O).

Reference： [1]Nomoto, Yuya; Horinouchi, Ryo; Nishiyama, Nobuo; Nakano, Keiji; Ichikawa, Yoshiyasu; Kotsuki, Hiyoshizo [Synlett, 2017, vol. 28, # 2, p. 265 - 269]

35
[ 110-93-0 ]
[ 1569-60-4 ]
[ 928-68-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; sodium hydroxide In methanol; water at 30℃; for 40h; Autoclave;
	With [Ir{1,3-bis(4′-methylphenyl)triazenide}Cp*Cl]; potassium hydroxide In isopropyl alcohol at 70℃; for 22h; Overall yield = 13 %Spectr.;

Reference： [1]Forato, Florian; Belhboub, Anouar; Monot, Julien; Petit, Marc; Benoit, Roland; Sarou-Kanian, Vincent; Fayon, Franck; Jacquemin, Denis; Queffelec, Clémence; Bujoli, Bruno [Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2457 - 2465]
[2]Camarena-Diáz, Juan P.; Iglesias, Ana L.; Chávez, Daniel; Aguirre, Gerardo; Grotjahn, Douglas B.; Rheingold, Arnold L.; Parra-Hake, Miguel; Miranda-Soto, Valentín [Organometallics, 2019, vol. 38, # 4, p. 844 - 851]

36
[ 110-93-0 ]
[ 62150-45-2 ]
4-(2-methyl-6-oxohept-2-en-1-yl)picolinonitrile [ No CAS ]
4-(2-methyl-6-oxohept-2-en-1-yl)picolinonitrile [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 10333 - 10337
Angew. Chem.,2018,vol. 130,p. 10490 - 10494,5

37
[ 110-93-0 ]
[ 1145-93-3 ]
C₁₆H₂₂O [ No CAS ]
C₁₆H₂₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60 % ee	With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 4h; Overall yield = 92 percent; Overall yield = 9.7 g;	1 General/Typical Procedure for Wittig reaction To a solution of the phosphonium salt of benzyl bromide (12 g, 46 mmol) and 6-methyl-5-hepten-2-one (5.3g, 42 mmol) in anhydrous DMF (50 mL), NaH (60% dispersion in mineral oil, 46 mmol) was added at 0° C. portion wise. The reaction mixture was allowed to stir 0° C. for 1 h, during which time the mixture developed a red color indicating the formation of ylide. After stirring at room temperature for 3 h, the reaction is complete. The mixture is diluted with water at 0° C. and the product is extracted with EtOAc. The organic layer is washed with saturated aqueous NaHCO3 and brine then dried over Na2SO4. The solvent is removed under reduced pressure and the yellow residue was passed through a short bed of silica gel eluting with ethyl acetate-hexane (5:95) to yield the coupled product (9.7 g, 92%) in a ratio of (E/Z: 80:20) as a pale yellow oil.

Reference： [1]Current Patent Assignee: UNIGEN CO LTD - US2020/115307, 2020, A1 Location in patent: Paragraph 0108

38
[ 110-93-0 ]
[ 28480-70-8 ]
6-chloro-2,7-dimethyl-2-(4-methylpent-3-en-1-yl)chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 6-Methyl-hept-5-en-2-on With pyrrolidine; butyric acid In dimethyl sulfoxide for 0.25h; Stage #2: 5'-chloro-2'-hydroxy-4'-methyl acetophenone In dimethyl sulfoxide at 20℃; for 2h;

Reference： [1]Kapuriya, Naval P.; Bhalodia, Jasmin J.; Ambasana, Mrunal A.; Patel, Rashmi B.; Bapodra, Atul H. [Journal of Heterocyclic Chemistry, 2020, vol. 57, # 9, p. 3369 - 3374]

39
[ 110-93-0 ]
[ 62026-31-7 ]
[ 3796-70-1 ]

Yield	Reaction Conditions	Operation in experiment
110 g	In tert-butyl methyl ether at 0℃; for 6h; Inert atmosphere;	1.4 4) Synthetic geranyl acetone: Under the protection of nitrogen, add 76g (0.60mol) of methyl heptenone and 200ml of methyl tert-butyl ether into a three-necked flask, stir, cool to 0, and slowly add freshly prepared 5-chloro-2-pentanone dropwise 400ml of methyl tert-butyl ether solution of ethylene ketal Grignard agent (containing 0.66 mol of 5-chloro-2-pentanone ethylene ketal Grignard agent), drip in about 2 hours, and keep the reaction at 0 for 4 hours , Slowly add 80ml of concentrated hydrochloric acid to quench the reaction, stir for 1 hour, filter, and heat the filtrate to reflux for 4 hours. After the reaction is over, cool to room temperature, add 300ml of water to the reaction solution, stir, stand for separation, take the organic layer and wash twice with water, each time 200ml, dry the organic layer with anhydrous sodium sulfate and recover the methyl tert-butyl under reduced pressure Base ether, the residue was rectified, and the 3mmHg 100-105°C fraction was collected to obtain a light yellow transparent liquid, namely geranyl acetone (110g, yield 94%).

Reference： [1]Current Patent Assignee: SHANGHAI MODERN PHARMACEUTICAL CO., LTD.; HENAN FOOD AND DRUG EVALUATION AND INSPECTION CENTER - CN111393275, 2020, A Location in patent: Paragraph 0061; 0072; 0080-0081

40
[ 110-93-0 ]
2-triphenylphosphoniumacetaldehyde dimethyl acetal bromide [ No CAS ]
[ 5392-40-5 ]

Yield	Reaction Conditions	Operation in experiment
90.8%	With sodium ethanolate In N,N-dimethyl-formamide at 10 - 20℃; for 4h; Inert atmosphere; Green chemistry;	3.2; 4 Step (2): Preparation of Citral (I) Under the protection of nitrogen, add 100 g of N,N-dimethylformamide, 7.5 g (0.11 mol) of solid sodium ethoxide, 43.1 g (0.1 mol) to a 500 ml four-neck flask equipped with stirring, thermometer and reflux condenser. The compound of formula III3obtained in the step (1) of Example 3 wascooled and kept between 10°C and 15°C, and 12.6 g (0.1 mole) of 6-methyl-5-hepten-2-one (IV) was added dropwise, The addition is completed in 1 hour, and then the reaction is stirred at 15-20°C for 3 hours.Recover N,N-dimethylformamide by distillation under reduced pressure, add 100 grams of water and 100 grams of dichloromethane to the residue obtained, and acidify with acetic acid with a mass concentration of 50% until the pH of the system is 3.5-4.0, 35- Stir at 40°C for 2 hours, stand still to separate the layers, extract the aqueous phase with dichloromethane twice, 50 grams each time, combine the organic phases, distill the organic phase to recover the dichloromethane, and distill under reduced pressure (70-85°C/2- 3mmHg) to obtain 13.8 g of colorless transparent liquid citral (I), the gas phase purity is 99.6%, and the yield is 90.8%.

Reference： [1]Current Patent Assignee: XINFA PHARMACEUTICAL CO LTD - CN111574349, 2020, A Location in patent: Paragraph 0078; 0094-0095; 0098-0099; 0100-0102

41
[ 110-93-0 ]
[ 52509-14-5 ]
[ 5392-40-5 ]

Yield	Reaction Conditions	Operation in experiment
90.1%	With potassium hydroxide In isopropyl alcohol at 10 - 20℃; for 4h; Inert atmosphere; Green chemistry;	5.2; 6 Step (2): Preparation of Citral (I) Under the protection of nitrogen, add 100 g of isopropanol and 6.2 g (0.11 mol) of solid potassium hydroxide into a 500 ml four-necked flask equipped with stirring, thermometer, constant pressure dropping funnel and reflux condenser. After stirring to dissolve, add 42.9 g (0.1 mole) of thecompound offormula III4obtained in the step (1) method of Example 5, cooled and kept between 10°C and 15°C, and 12.6 g (0.1 mole) of 6-methyl-5-heptene-2 was added dropwise -Ketone (IV), the addition is completed in 1 hour, and then the reaction is stirred at 15-20°C for 3 hours.Then add 100 grams of water and 100 grams of dichloromethane, acidify with 50% aqueous phosphoric acid until the pH of the system is 3.0-3.5, stir at 35-40°C for 3 hours, stand still and separate, and extract the aqueous phase twice with dichloromethane. 50 grams each time, combine the organic phases, distill the organic phase to recover dichloromethane, and distill under reduced pressure (70-85°C/2-3mmHg) to obtain 13.7 grams of colorless transparent liquid citral (I), with a gas phase purity of 99.3%. The rate is 90.1%.

Reference： [1]Current Patent Assignee: XINFA PHARMACEUTICAL CO LTD - CN111574349, 2020, A Location in patent: Paragraph 0078; 0103-0104; 0107-0108; 0109-0112

42
[ 110-93-0 ]
2,4,6-tris(triphenylphosphonium)-1,3,5-trioxane trichloride [ No CAS ]
[ 5392-40-5 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With potassium hydroxide In isopropyl alcohol at 10 - 25℃; for 4h; Inert atmosphere; Green chemistry;	7.2; 8; 2 Step (2): Preparation of Citral (I) Under the protection of nitrogen, add 6.2g (0.11mol) solid potassium hydroxide and 100g isopropanol to a 500ml four-necked flask equipped with stirring, thermometer, constant pressure dropping funnel and reflux condenser. After stirring to dissolve, add 34.1 g (0.033 mol) of thecompound offormula III5obtained in the step (1) of Example 7 wascooled and kept between 10°C and 15°C, and 12.6 g (0.1 mol) of 6-methyl-5-heptene-2 was added dropwise -Ketone (IV), the addition is completed in 1 hour, and then the reaction is stirred at 20-25°C for 3 hours.Then add 100 grams of water and 100 grams of dichloromethane, and acidify with 30% ammonium chloride aqueous solution until the pH of the system is 3.5-4.0. Stir at 35-40°C for 3 hours, stand still and separate into layers. The aqueous phase is extracted with dichloromethane. 50 grams each time, combine the organic phases, distill the organic phase to recover dichloromethane, and distill under reduced pressure (70-85°C/2-3mmHg) to obtain 14.0 grams of colorless transparent liquid citral (I) with a gas purity of 99.2% The yield was 92.1%.

Reference： [1]Current Patent Assignee: XINFA PHARMACEUTICAL CO LTD - CN111574349, 2020, A Location in patent: Paragraph 0078; 0113-0114; 0117-0118; 0119-0121; 0138-0140

43
[ 110-93-0 ]
[ 105-39-5 ]
[ 106-72-9 ]

Yield	Reaction Conditions	Operation in experiment
95.13%	Stage #1: 6-Methyl-hept-5-en-2-on; chloroacetic acid ethyl ester With salcomine; sodium carbonate In 1,2-dichloro-ethane at 55℃; for 6h; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane at 20℃; for 1h; Stage #3: With copper(II) sulfate In water; 1,2-dichloro-ethane at 100℃;	1-12; 1-4 Example 2 Add 46g potassium carbonate and 0.3g bis-salicylic aldehyde ethylenediamine cobalt(II) into 200g of toluene. After mixing uniformly, the temperature is raised to 55°C to obtain the first mixed liquid; 84g methylheptenone and 41g Mix ethyl chloroacetate to obtain a second mixed liquid; add the second mixed liquid dropwise to the first mixed liquid. During the dropping process, the temperature is maintained at 55°C and the dropping time is 4 hours. After the dropping, continue to keep warm After 2 hours, the dashen reaction was completed, and then the temperature was lowered to 5° C. to obtain a first reaction liquid, and the first reaction liquid contained ethyl epoxyoctanoate.Under stirring, 65g of sodium hydroxide aqueous solution was added dropwise to the first reaction solution for saponification reaction. During the dropping process, the temperature was controlled to be lower than 20°C, and the mass fraction of sodium hydroxide in the sodium hydroxide aqueous solution was 20% After the dropwise addition, the temperature was kept at 20°C for 1 hour to complete the saponification reaction, and then the temperature was lowered to room temperature to obtain a second reaction liquid.The second reaction liquid is allowed to stand for liquid separation, and the first organic phase and the first aqueous phase are separated to obtain the first organic phase. Methylheptenone; the sodium salt and potassium salt of epoxy acid are included in the first aqueous phase, and the first organic phase is recycled for use in the Dashen reaction. 200g of toluene is added to the first aqueous phase, and then acidified with concentrated hydrochloric acid to The pH is about 4. During the acidification process, control the temperature at 10°C-25°C. After the acidification is completed, stand still for layering, discard the second aqueous phase. The second organic phase is washed with water and distilled to remove toluene at atmospheric pressure to obtain a Residues of oxyacids.Add 2g of copper sulfate to the residue to carry out decarboxylation under reduced pressure. During the decarboxylation under reduced pressure, the temperature is 100, the vacuum degree is 800pa, and the decarboxylation under reduced pressure is complete to obtain the crude melon aldehyde; the crude melon aldehyde is refined under reduced pressure Distillation purification, the temperature of the rectification was 90°C, to obtain 44.63 g product melon aldehyde, the yield was 95.13% in terms of ethyl chloroacetate, and the purity was 98.9%.

Reference： [1]Current Patent Assignee: ZHEJIANG NHU CO., LTD. - CN113563287, 2021, A Location in patent: Paragraph 0098-0165

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H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
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H302	Harmful if swallowed
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H310	Fatal in contact with skin
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H314	Causes severe skin burns and eye damage
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H370	Causes damage to organs
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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. 110-93-0 ] {[proInfo.proName]}

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[ 110-93-0 ] Synthesis Path-Upstream 1~7

[ 110-93-0 ] Synthesis Path-Downstream 1~43

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