[ CAS No. 830-13-7 ]

Name: 830-13-7|Cyclododecanone|99%
Brand: Ambeed
SKU: A113074
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Quality Control of [ 830-13-7 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 830-13-7 ]

CAS No. :	830-13-7	MDL No. :	MFCD00003722
Formula :	C₁₂H₂₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SXVPOSFURRDKBO-UHFFFAOYSA-N
M.W :	182.30	Pubchem ID :	13246
Synonyms :

Safety of [ 830-13-7 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P201-P264-P280-P301+P330+P331-P312	UN#:	3077
Hazard Statements:	H302-H361-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 830-13-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 830-13-7 ]
Downstream synthetic route of [ 830-13-7 ]

[ 830-13-7 ] Synthesis Path-Upstream 1~4

1
[ 830-13-7 ]
[ 17278-74-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 161 - 168

2
[ 830-13-7 ]
[ 505-95-3 ]
[ 5675-51-4 ]
[ 3903-40-0 ]

Reference： [1] Patent: WO2013/116029, 2013, A1, . Location in patent: Paragraph 00131

3
[ 830-13-7 ]
[ 3903-40-0 ]

Reference： [1] Patent: CN107337592, 2017, A,

4
[ 830-13-7 ]
[ 108-95-2 ]
[ 29651-54-5 ]

Yield	Reaction Conditions	Operation in experiment
75.4%	Stage #1: at 60 - 80℃; for 1 h; Stage #2: at 64 - 68℃; for 8 h;	In a 500 ml glass reaction vessel,258.14 g (2.74 mol) of phenol,And 13.73 g (0.137 mol) of 98percent sulfuric acid were charged,The temperature was raised to 80 ° C. After stirring at the same temperature for 1 hour,It was cooled to 60 ° C.,50.02 g (0.274 mol) of cyclododecanone,5.57 g (0.0275 mol) of n-dodecylmercaptan was charged and stirred for 8 hours at 64 to 68 ° C. under reduced pressure of 2.7 kPa while blowing nitrogen gas. After completion of stirring, the mixture was allowed to stand still overnight,When the reaction mass was analyzed by gas chromatography,No cyclododecanone was detected. To the resulting reaction mass were added toluene,Ion exchanged water was added and neutralized with sodium hydroxide,Ion exchangeIt was washed with water. The obtained organic layer was cooled as it was,Precipitated crystals were taken out by filtration. The obtained crystals were recrystallized from methanol water, taken out by filtration,After drying, 72.89 g of 1,1-bis (4-hydroxyphenyl) cyclododecane was obtained (HPLC purity 100percent, yield 75.4percent).
77.04 g	Stage #1: at 80℃; for 1 h; Stage #2: at 30 - 65℃; for 52 h;	258.19 g (2.74 mol) of phenol and 13.72 g (0.137 mol) of 98percent sulfuric acid were charged into a 500 ml glass reaction vessel equipped with a stirrer, a condenser and a thermometer, and the temperature was raised to 80 ° C. After stirring at the same temperature for 1 hour, 50.09 g (0.275 mol) of cyclododecanone at 60 ° C.,5.54 g (0.0274 mol) of n-dodecylmercaptan was added and reacted at 65 ° C. while removing water at 1.3 kPa until the remaining amount of cyclododecanone reached 50percent of the initial charge amount.After recovering pressure to normal pressure with nitrogen gas, it was cooled to 30 ° C. and left to stand at the same temperature for 52 hours.0.15 g of the solidified reaction mass was scraped off, and the reaction mass was analyzed by gas chromatography. As a result, the remaining amount of cyclododecanone was 1percent of the initially charged amount, and 1, 1-bis (4-hydroxy Phenyl) cyclododecane (the molar ratio to the initially charged amount of cyclododecanone) was 90.2percent. Toluene and ion exchanged water were added to the obtained reaction mass, neutralized with sodium hydroxide, and then washed with ion exchanged water. The obtained organic layer was cooled as it was, the precipitated crystal was taken out by filtration and dried. The obtained crystals were recrystallized from methanol water, taken out by filtration and dried to obtain 77.04 g (0.219 mol, yield 79.5 mmol) of 1, 1-bis (4-hydroxyphenyl) cyclododecane percent, HPLC purity 100percent) was obtained

Reference： [1] Macromolecules, 2005, vol. 38, # 10, p. 4147 - 4156
[2] Patent: JP2016/20325, 2016, A, . Location in patent: Paragraph 0033
[3] Patent: JP2015/51935, 2015, A, . Location in patent: Paragraph 0031-0040

[ 830-13-7 ] Synthesis Path-Downstream 1~69

1
[ 830-13-7 ]
[ 693-23-2 ]

Yield	Reaction Conditions	Operation in experiment
	With chromium(VI) oxide; acetic acid
	With chromium(VI) oxide; acetic acid
	With nitric acid for 1h; Heating;	13 In an example, cyclododecanone (CDDK) (36.8 g, 0.20 moles) is heated with an excess of nitric acid and a V/Cu catalyst (e.g., ammonium vanadate and copper nitrate) in a glass reactor for 1 hour. A portion of the reaction work-up is evaporated and then allowed to cool. A product of the reaction is identified as dodecanedioic acid (DDDA) after crystallization from solution. The crystallized DDDA is further filtered and washed with cold water. A purity for the DDDA is expected to be 99% and the yield based on cyclododecanol is 88%. The filtrate upon further evaporation and crystallization will provide another crop of crystals comprising mixed dicarboxylic acids of 12, 11, 10, 9, 8 and 7 carbon atoms. The combined overall yields of DDDA and mixed di-acids based on CDDK are about 94%.

With nitric acid Green chemistry;

Step 2: Using cyclododecanone as raw material, α,ω-dodecane is obtained through oxidation reaction and heteropoly acid catalyzed transesterificationDiacid monomethyl ester, in which the molar ratio of acid to alcohol is 1:3, the solvent is anhydrous toluene, and the amount of catalyst-supported heteropolyacid used is 2% of the substrateReaction time 5h

Reference： [1]Ruzicka; Stoll; Schinz [Helvetica Chimica Acta, 1926, vol. 9, p. 250,260][Helvetica Chimica Acta, 1928, vol. 11, p. 671 Anm. 3, 685]
[2]Ruzicka; Stoll; Schinz [Helvetica Chimica Acta, 1926, vol. 9, p. 250,260][Helvetica Chimica Acta, 1928, vol. 11, p. 671 Anm. 3, 685]
[3]Current Patent Assignee: KOCH INDUSTRIES, INC. - US2009/240068, 2009, A1 Location in patent: Page/Page column 6
[4]Current Patent Assignee: LIAONING INST SCIENCE TECH - CN107337592, 2017, A Location in patent: Paragraph 0023; 0024

2
[ 830-13-7 ]
[ 294-62-2 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 3952 - 3958
[2]Helvetica Chimica Acta,1930,vol. 13,p. 1152,1172

3
[ 1502-03-0 ]
[ 830-13-7 ]
[ 1781-76-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1964,vol. 679,p. 83 - 94

4
[ 97-94-9 ]
[ 4373-12-0 ]
[ 10596-55-1 ]
[ 294-62-2 ]
[ 1501-82-2 ]
[ 88011-88-5 ]
[ 830-13-7 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 3991 - 3994

5
[ 201230-82-2 ]
[ 294-62-2 ]
[ 884-36-6 ]
[ 1724-39-6 ]
[ 830-13-7 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 4389 - 4392

6
[ 294-62-2 ]
[ 830-13-7 ]

Reference： [1]Synthetic Communications,1987,vol. 17,p. 19 - 24
[2]Chemical Communications,2012,vol. 48,p. 11576 - 11578
[3]Tetrahedron,1990,vol. 46,p. 3743 - 3752
[4]Tetrahedron Letters,1990,vol. 31,p. 1657 - 1660
[5]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 771 - 777
[6]Inorganic Chemistry,2019,vol. 58,p. 4141 - 4151

7
[ 294-62-2 ]
[ 1129-89-1 ]
[ 1724-39-6 ]
[ 830-13-7 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1992,p. 589 - 590

8
[ 294-62-2 ]
[ 7795-35-9 ]
[ 1724-39-6 ]
[ 830-13-7 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 9195 - 9206
[2]Tetrahedron,1992,vol. 48,p. 9195 - 9206
[3]Tetrahedron,1992,vol. 48,p. 9195 - 9206

9
[ 294-62-2 ]
[ 34039-83-3 ]
[ 830-13-7 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 9195 - 9206

10
[ 294-62-2 ]
[ 1724-39-6 ]
[ 830-13-7 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 19 - 30
[2]Tetrahedron,1994,vol. 50,p. 19 - 30
[3]Tetrahedron Letters,1989,vol. 30,p. 2237 - 2240
[4]Tetrahedron Letters,1986,vol. 27,p. 2849 - 2852
[5]Journal of the Chemical Society. Perkin transactions I,1986,p. 947 - 956
[6]Journal of the Chemical Society. Chemical communications,1986,p. 1727 - 1729
[7]Tetrahedron Letters,1994,vol. 35,p. 4681 - 4684
[8]Tetrahedron,1990,vol. 46,p. 3743 - 3752
[9]Tetrahedron Letters,1989,vol. 30,p. 2237 - 2240
[10]Tetrahedron,1991,vol. 47,p. 6561 - 6570
[11]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 771 - 777
[12]Chemical Communications,1997,p. 557 - 558
[13]Tetrahedron,2003,vol. 59,p. 6409 - 6414
[14]Journal of Catalysis,2005,vol. 229,p. 64 - 71
[15]Chemistry - A European Journal,2006,vol. 12,p. 3401 - 3409
[16]Organic Process Research and Development,2003,vol. 7,p. 426 - 428

11
[ 294-62-2 ]
[ 1724-39-6 ]
[ 35522-56-6 ]
[ 830-13-7 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 2483 - 2492
[2]Tetrahedron,1985,vol. 41,p. 2483 - 2492

12
[ 294-62-2 ]
[ 1724-39-6 ]
[ 122334-55-8 ]
[ 122334-56-9 ]
[ 830-13-7 ]

Reference： [1]Journal of the American Chemical Society,1989,vol. 111,p. 7144 - 7149

13
[ 1502-03-0 ]
[ 830-13-7 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 843 - 845
[2]Tetrahedron Letters,1983,vol. 24,p. 3465 - 3468
[3]Journal of Organic Chemistry,1983,vol. 48,p. 332 - 337

14
[ 4296-15-5 ]
[ 77857-65-9 ]
[ 830-13-7 ]
[ 77857-83-1 ]
[ 77857-83-1 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 3088 - 3093

15
[ 1191-08-8 ]
[ 830-13-7 ]
[ 98051-54-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With aluminium trichloride In dichloromethane for 0.25h;

Reference： [1]Nickon, Alex; Rodriguez, Abimael D.; Shirhatti, Vilas; Ganguly, Rathindra [Journal of Organic Chemistry, 1985, vol. 50, # 22, p. 4218 - 4226]

16
[ 2785-78-6 ]
[ 830-13-7 ]
[ 76836-29-8 ]

Reference： [1]Chemische Berichte,1980,vol. 113,p. 3697 - 3705

17
[ 830-13-7 ]
[ 110-94-1 ]
[ 124-04-9 ]
[ 111-20-6 ]
[ 110-15-6 ]
[ 1852-04-6 ]
[ 693-23-2 ]

Reference： [1]Journal of applied chemistry of the USSR,1982,vol. 55,p. 2492 - 2495
Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1982,vol. 55,p. 2742 - 2746

18
[ 830-13-7 ]
[ 111-20-6 ]
[ 1852-04-6 ]
[ 693-23-2 ]

Reference： [1]Journal of applied chemistry of the USSR,1982,vol. 55,p. 2492 - 2495
Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1982,vol. 55,p. 2742 - 2746

19
[ 294-62-2 ]
[ 108-93-0 ]
[ 1724-39-6 ]
[ 108-94-1 ]
[ 830-13-7 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 4681 - 4684

20
[ 294-62-2 ]
[ 121-45-9 ]
[ 1724-39-6 ]
[ 138764-44-0 ]
[ 830-13-7 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 4671 - 4674

21
[ 6914-71-2 ]
[ 830-13-7 ]
2-Oxo-1-oxa-spiro[5.11]heptadecane-3-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 7805 - 7808

22
[ 830-13-7 ]
[ 10061-02-6 ]
2-(chloroprop-3-enyl)cyclododecanone [ No CAS ]

Reference： [1]Russian Chemical Bulletin,1994,vol. 43,p. 608 - 611
Izvestiya Akademi Nauk, Seriya Khimicheskaya,1994,p. 659 - 661

23
[ 50-00-0 ]
[ 6091-44-7 ]
[ 830-13-7 ]
[ 3045-70-3 ]

Reference： [1]Pharmazie,1995,vol. 50,p. 668 - 671

24
[ 294-62-2 ]
[ 693-23-2 ]
[ 830-13-7 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 4520 - 4526

25
(+-)-2-hydroxy-cyclododecanone-⁽¹⁾ [ No CAS ]
[ 294-62-2 ]
[ 830-13-7 ]

Reference： [1]Helvetica Chimica Acta,1947,vol. 30,p. 1741,1745

26
2-hydroxy-cyclododecanone-⁽¹⁾ [ No CAS ]
[ 294-62-2 ]
[ 830-13-7 ]

Reference： [1]Helvetica Chimica Acta,1947,vol. 30,p. 1741,1745

27
[ 294-62-2 ]
[ 693-23-2 ]
[ 1724-39-6 ]
[ 830-13-7 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 7889 - 7891
[2]Organic Process Research and Development,2003,vol. 7,p. 426 - 428

28
[ 17887-80-8 ]
[ 830-13-7 ]
[ 1553-03-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With iodine In dichloromethane at 20℃; for 65h;
82 % Spectr.	With N-Bromosuccinimide In dichloromethane at 20℃; for 36h;

Reference： [1]Karimi, Babak; Golshani, Behzad [Synthesis, 2002, # 6, p. 784 - 788]
[2]Karimi, Babak; Hazarkhani, Hassan; Maleki, Jafar [Synthesis, 2005, # 2, p. 279 - 285]

29
[ 17649-86-4 ]
[ 830-13-7 ]
3-hydroxy-1-(methylthio)-5,6,7,8,9,10,11,12,13,14-decahydrobenzododecene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;

Reference： [1]Barun, Okram; Nandi, Sukumar; Panda, Kausik; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar [Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5398 - 5401]

30
[ 294-62-2 ]
[ 693-23-2 ]
[ 1724-39-6 ]
[ 830-13-7 ]
bis(cyclododecyl)dodecanedioate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2004,vol. 346,p. 286 - 296

31
[ 294-62-2 ]
[ 64-19-7 ]
[ 1724-39-6 ]
[ 1855-59-0 ]
[ 830-13-7 ]

Reference： [1]Chemistry Letters,2004,vol. 33,p. 198 - 199

32
[ 294-62-2 ]
[ 34039-83-3 ]
[ 1724-39-6 ]
[ 830-13-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 2251 - 2255
[2]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 2251 - 2255

33
[ 830-13-7 ]
[ 947-04-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium azide; sulfuric acid; In ethyl acetate; at 60 - 77℃; for 2h;	Cyclododecanone (100 g, 0.55 mol),Sodium azide (64 g, 0.98 mol) and ethyl acetate (700 mL) were mixed and stirred,The temperature inside the reactor At 60 C After heating,Concentrated sulfuric acid (167 g, 1.7 mol) was slowly added dropwise, and the mixture was refluxed at 77 C for 2 hours.The temperature inside the reactor was cooled to 50 ,The reaction solution was neutralized with 20% aqueous sodium hydroxide solution, and the organic layer was separated and washed twice with water.Then, the obtained reaction solution was cooled to 10 ,The resulting solid was filtered to obtain 106 g (yield: 98%) of laurolactam in the form of a white solid.
95%	With hydroxylamine hydrochloride; In benzonitrile; at 90℃; for 12h;Inert atmosphere;	General procedure: A typical procedure for the Beckmann rearrangement of 1 by Ti4+-mont is as follows. Ti4+-mont (0.10 g) was placed in a reaction vessel, followed by addition of benzonitrile (5 mL) and 1 (1 mmol). The reaction mixture was vigorously stirred at 90 C under Ar for 3 h. After the reaction, the mixture was centrifuged, and the supernatant was analyzed by GC with naphthalene as an internal standard to determine the conversion and yield.
84%	With hydroxylamine hydrochloride; p-toluenesulfonyl chloride; zinc(II) chloride; In acetonitrile; at 82℃; for 12h;Inert atmosphere;	To a round bottom flask (50 mL) was added anhydrous acetonitrile (10 mL), cyclododecanone (365 mg, 2.0 mmol) andAfter adding hydroxylammonium chloride (167 mg, 2.4 mmol) in succession,The mixture was stirred under nitrogen for 10 minutes. after,Para-Toluene sulfonyl chloride (TsCl, 19 mg, 0.1 mmol,)And zinc chloride (ZnCl2, 14 mg, 0.1 mmol) were added,The mixture was heated to 82 DEG C for 12 hours under reflux.After completion of the reaction, the reaction solution was cooled to room temperature,The acetonitrile used as the solvent was removed under reduced pressure.The concentrated product was dissolved in ethyl acetate (20 mL)A saturated aqueous sodium bicarbonate solution (20 mL)To neutralize the organic layer.The separated aqueous layer was extracted with ethyl acetate (20 mL)And the resultant mixture was combined with the organic layer extracted previously,The residual water in the organic layer was removed with magnesium sulfate.The magnesium sulfate was filtered with a sintered glass filter to remove it,Ethyl acetate in the filtrate was removed by distillation under reduced pressure,The concentrated product was purified by silica gel column chromatography(silica gel column chromatography) to obtain 333 mg (yield: 84%) of laurolactam as a white solid.

61%

With O-trifluorobenzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid; In water; acetonitrile; at 20℃;Inert atmosphere;

General procedure: Table 2 shows the results of examining various catalysts in the reaction of synthesizing N- (2-naphthyl) acetamide from 2-acetonaphthone. Examples of the acid catalyst include hydrochloric acid, sulfuric acid, methanesulfonic acid, tosylic acid monohydrate, trifluoromethanesulfonic acid, bistrifluoromethanesulfonimide, boron trifluoride diethyl ether complex, scandium (III) trifluoromethanesulfonate, trifluoromethanesulfone Iron (III) oxide, trifluoromethanesulfoCopper (II) trifluoromethanesulfonate, bismuth trifluoromethanesulfonate (III), titanium tetrachloride and iron trichloride have excellent effects (Entries 2 to 14).

Reference： [1]Patent: KR2017/135373,2017,A .Location in patent: Paragraph 0025; 0043-0050
[2]Journal of Chemical Research,2006,p. 218 - 219
[3]Tetrahedron Letters,2012,vol. 53,p. 5211 - 5214
[4]Journal of Organic Chemistry,2018,vol. 83,p. 13080 - 13087
[5]Science,2020,vol. 367,p. 281 - 285
[6]Patent: KR2019/10201,2019,A .Location in patent: Paragraph 0033-0041
[7]Tetrahedron Letters,2008,vol. 49,p. 4742 - 4745
[8]Synthetic Communications,2006,vol. 36,p. 2211 - 2216
[9]Patent: JP2018/135293,2018,A .Location in patent: Paragraph 0029; 0031
[10]Synthesis,1991,p. 1216 - 1220
[11]Patent: US2013/5960,2013,A1
[12]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 143 - 148
[13]Synlett,2015,vol. 26,p. 331 - 334
[14]Journal of Organic Chemistry,2018,vol. 83,p. 2040 - 2049
[15]Journal of the American Chemical Society,2018,vol. 140,p. 5264 - 5271
[16]European Journal of Organic Chemistry,2020,vol. 2020,p. 311 - 315
[17]Chinese Chemical Letters,2022,vol. 33,p. 2407 - 2410

34
[ 830-13-7 ]
[ 108-95-2 ]
[ 29651-54-5 ]

Yield	Reaction Conditions	Operation in experiment
75.4%		In a 500 ml glass reaction vessel,258.14 g (2.74 mol) of phenol,And 13.73 g (0.137 mol) of 98% sulfuric acid were charged,The temperature was raised to 80 C. After stirring at the same temperature for 1 hour,It was cooled to 60 C.,50.02 g (0.274 mol) of cyclododecanone,5.57 g (0.0275 mol) of n-dodecylmercaptan was charged and stirred for 8 hours at 64 to 68 C. under reduced pressure of 2.7 kPa while blowing nitrogen gas. After completion of stirring, the mixture was allowed to stand still overnight,When the reaction mass was analyzed by gas chromatography,No cyclododecanone was detected. To the resulting reaction mass were added toluene,Ion exchanged water was added and neutralized with sodium hydroxide,Ion exchangeIt was washed with water. The obtained organic layer was cooled as it was,Precipitated crystals were taken out by filtration. The obtained crystals were recrystallized from methanol water, taken out by filtration,After drying, 72.89 g of 1,1-bis (4-hydroxyphenyl) cyclododecane was obtained (HPLC purity 100%, yield 75.4%).
77.04 g		258.19 g (2.74 mol) of phenol and 13.72 g (0.137 mol) of 98% sulfuric acid were charged into a 500 ml glass reaction vessel equipped with a stirrer, a condenser and a thermometer, and the temperature was raised to 80 C. After stirring at the same temperature for 1 hour, 50.09 g (0.275 mol) of cyclododecanone at 60 C.,5.54 g (0.0274 mol) of n-dodecylmercaptan was added and reacted at 65 C. while removing water at 1.3 kPa until the remaining amount of cyclododecanone reached 50% of the initial charge amount.After recovering pressure to normal pressure with nitrogen gas, it was cooled to 30 C. and left to stand at the same temperature for 52 hours.0.15 g of the solidified reaction mass was scraped off, and the reaction mass was analyzed by gas chromatography. As a result, the remaining amount of cyclododecanone was 1% of the initially charged amount, and 1, 1-bis (4-hydroxy Phenyl) cyclododecane (the molar ratio to the initially charged amount of cyclododecanone) was 90.2%. Toluene and ion exchanged water were added to the obtained reaction mass, neutralized with sodium hydroxide, and then washed with ion exchanged water. The obtained organic layer was cooled as it was, the precipitated crystal was taken out by filtration and dried. The obtained crystals were recrystallized from methanol water, taken out by filtration and dried to obtain 77.04 g (0.219 mol, yield 79.5 mmol) of 1, 1-bis (4-hydroxyphenyl) cyclododecane %, HPLC purity 100%) was obtained

Reference： [1]Macromolecules,2005,vol. 38,p. 4147 - 4156
[2]Patent: JP2016/20325,2016,A .Location in patent: Paragraph 0033
[3]Patent: JP2015/51935,2015,A .Location in patent: Paragraph 0031-0040

35
[ 28657-75-2 ]
[ 830-13-7 ]
C₂₁H₂₇NO₂*HCl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With chloro-trimethyl-silane In N,N-dimethyl-formamide at 95℃;

Reference： [1]Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Plaskon, Andrey S.; Naumchik, Vasiliy S.; Tolmachev, Andrei A. [Synthesis, 2007, # 8, p. 1214 - 1224]

36
[ 118994-84-6 ]
[ 830-13-7 ]
[ 936331-89-4 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1875 - 1878

37
[ 32042-38-9 ]
[ 830-13-7 ]
[ 949-07-5 ]

Reference： [1]Organic Letters,1999,vol. 1,p. 989 - 991

38
[ 830-13-7 ]
[ 17278-74-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1986,p. 161 - 168

39
[ 943-93-1 ]
[ 294-62-2 ]
[ 1724-39-6 ]
[ 830-13-7 ]
[ 286-99-7 ]

Reference： [1]Patent: US6335472,2002,B1 .Location in patent: Example 8-10
[2]Patent: US6335472,2002,B1 .Location in patent: Example 14
[3]Patent: US6335472,2002,B1 .Location in patent: Example 13
[4]Patent: US6335472,2002,B1 .Location in patent: Example 11,15
[5]Patent: US6335472,2002,B1 .Location in patent: Example 3,16-18
[6]Patent: US6335472,2002,B1 .Location in patent: Example 7,12

40
[ 943-93-1 ]
[ 286-99-7 ]
[ 1502-29-0 ]
[ 294-62-2 ]
[ 1724-39-6 ]
[ 830-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;platinum on carbon; at 70 - 130℃; under 3750.38 - 37503.8 Torr; for 0.166667 - 2h;	In an SUS-made autoclave having an inner volume of 100 ml and equipped with a stirrer, 20 g (0.112 mol) of 1,2-epoxy-5,9-cyclododecadiene and 0.08 g of a 5 mass% Pt/C catalyst (50% hydrous product, produced by N.E. Chemcat Corporation; 0.0102 mmol as platinum atom) were added and after pressurizing to 5 MPa with hydrogen at room temperature, heated to a temperature of 70C. Under the same pressure, the contents were heated with stirring until the hydrogen absorption did not occur. After the completion of reaction, the reaction solution was cooled to room temperature, the catalyst was removed by filtration and the resulting reaction solution was analyzed. The analysis of the reaction solution was performed by gas chromatography. As a result, 1,2-epoxy-5,9-cyclododecadiene was 100% consumed and epoxycyclododecane (hereinafter referred to as "BCD") was produced in a yield of 99.6 mol%. Also, as by-products, cyclododecanone (hereinafter referred to as "CDON") was produced in 0.04 mol%, cyclododecanol (hereinafter referred to as "CDOL") was produced in 0.20 mol% and cyclododecane (hereinafter referred to as "CDAN") was produced in 0.04 mol%.

Reference： [1]Patent: EP1433771,2004,A1 .Location in patent: Page 8-9
[2]Patent: EP1433771,2004,A1 .Location in patent: Page 8-9
[3]Patent: EP1433771,2004,A1 .Location in patent: Page 5-6; 8-9

41
[ 947-04-6 ]
[ 830-13-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example 7 A refined laurolactam was prepared by the same procedures as in Example 1, except that the starting cyclododecanone material was prepared by pre-treating a unrefined cyclododecanone material containing 700 ppm of cyclododecenone with an aqueous solution of 10% by mass of sodium hydroxide at 200 C. for 5 hours, and then subjecting the resultant pretreatment reaction mixture to refining distillation.
		Example 8 A refined laurolactam was prepared by the same procedures as in Example 3, except that the starting cyclododecanone material was prepared by pre-treating a unrefined cyclododecanone material containing 2,800 ppm of epoxycylcododecane with γ-alumina at 200 C. for 2 hours, and subjecting the resultant pretreatment reaction mixture to refining distillation. In the pretreated cyclododecanone material, the content of epoxycylcododecane was 170 ppm. The resultant refined laurolactam exhibited an LT.diff of 5.8%.
		Example 9 A refined laurolactam was prepared by the same procedures as in Example 5, except that the starting cyclododecanone material was prepared by pre-treating a unrefined cyclododecanone material containing 1,50b ppm of cycloundecanecarboxyaldehyde with an aqueous solution of 10% by mass of sodium hydroxide at 180 C. for 10 hours, and subjecting the resultant pretreatment reaction mixture to refining distillation. In the pretreated cyclododecanone material, the content of cycloundecanecarboxyaldehyde was not detected. The resultant refined laurolactam exhibited an LT.diff of 5.0%.

Reference： [1]Patent: US2003/139596,2003,A1
[2]Patent: US2003/139596,2003,A1
[3]Patent: US2003/139596,2003,A1

42
[ 946-89-4 ]
[ 947-04-6 ]
[ 830-13-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 2894 - 2897
[2]Journal of Catalysis,2009,vol. 263,p. 42 - 55

43
[ 294-62-2 ]
[ 112-54-9 ]
[ 1724-39-6 ]
[ 2698-67-1 ]
[ 830-13-7 ]

Reference： [1]Synlett,2008,p. 1623 - 1626

44
[ 4904-61-4 ]
[ 1724-39-6 ]
[ 943-93-1 ]
[ 830-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen at 100℃;	7 In yet another example of a continuous oxidation process, cyclododeca-1,5,9-triene (CDDT) and oxygen gas are preheated separately to 100° C. and pumped into the bottom of a bubble column reactor. The pump at the bottom of the bubble column provides circulation to the liquid after passing through a heat exchanger. A slip stream sample from the pump circulation loop, equivalent to the amount of cyclododeca-1,5,9-triene introduced is continuously taken out as reaction product. The pressure in the reactor is maintained at 100 psig (ca. 790 kPa absolute) throughout the continuous oxidation reaction by means of a control valve in a column vent line. The cyclododeca-1,5,9-triene rate of feed is varied in order to provide different residence times for the reaction. The conversion of cyclododeca-1,5,9-triene into products (ECDDD, CDDA, CDDK) is 96% and selectivity is 97% under a best selected feed rate for the CDDT.

Reference： [1]Current Patent Assignee: KOCH INDUSTRIES, INC. - US2009/240068, 2009, A1 Location in patent: Page/Page column 5

45
[ 946-89-4 ]
[ 947-04-6 ]
2-dodecenal [ No CAS ]
[ 830-13-7 ]

Reference： [1]Journal of Catalysis,2009,vol. 263,p. 42 - 55

46
[ 316-46-1 ]
[ 830-13-7 ]
[ 1251763-85-5 ]

Reference： [1]Helvetica Chimica Acta,2010,vol. 93,p. 1500 - 1512

47
[ 294-62-2 ]
[ 1724-39-6 ]
[ 3008-41-1 ]
[ 15199-41-4 ]
[ 830-13-7 ]

Reference： [1]Applied Catalysis A: General,2010,vol. 388,p. 22 - 30

48
[ 14150-94-8 ]
[ 830-13-7 ]
5,6,7,8,9,10,11,12,13,14-decahydro-3-nitrocyclododeca<b>pyridine [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2009,vol. 45,p. 1045 - 1049

49
[ 4904-61-4 ]
[ 830-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dihydrogen peroxide / phosphotungstic acid; Aliquat 336 / water 2: hydrogen / platinum on activated charcoal 3: lithium iodide / 230 °C
	Multi-step reaction with 2 steps 1: ruthenium trichloride; triphenylphosphine; acetic acid; formaldehyd; hydrogen / water; ethanol / 6.67 h / 25 - 160 °C / 7500.75 - 15001.5 Torr 2: dinitrogen monoxide / cyclohexane / 6 h / 300 - 350 °C / 75007.5 Torr / Flow reactor
	Multi-step reaction with 2 steps 1: triphenylphosphine; ruthenium trichloride; acetic acid; formaldehyd; hydrogen / water; ethanol / 6.67 h / 25 - 160 °C / 7500.75 - 15001.5 Torr 2: dinitrogen monoxide / 1 h / Flow reactor

Multi-step reaction with 3 steps 1: acetic acid; hydrogen; ruthenium trichloride; triphenylphosphine; formaldehyd / 6.83 h / 25 - 160 °C 2: ortho-tungstic acid; phosphoric acid; Tri-n-octylamine; dihydrogen peroxide / water / 4 h / 100 °C 3: lithium bromide / 2 h / 200 °C / Inert atmosphere; Glovebox

Reference： [1]Current Patent Assignee: UBE INDUSTRIES LIMITED - US2013/5960, 2013, A1
[2]Current Patent Assignee: HANWHA SOLUTIONS CORPORATION - KR2019/80596, 2019, A
[3]Current Patent Assignee: HANWHA SOLUTIONS CORPORATION - KR2019/80566, 2019, A
[4]Current Patent Assignee: HANWHA SOLUTIONS CORPORATION - US2022/24868, 2022, A1

50
[ 1724-39-6 ]
[ 1502-03-0 ]
[ 830-13-7 ]

Yield	Reaction Conditions	Operation in experiment
74%Chromat.; 21%Chromat.	With ammonia; In o-xylene; at 170℃; under 3000.3 Torr; for 20h;Sealed tube; Autoclave;	General procedure: Ni/CaSiO3 pre-reduced at 600C was used as a standard catalyst. For the reaction of alcohols with NH3, the pre-reduced catalyst in the closed glass tube sealed with a septum inlet was cooled to room temperature under H2 atmosphere. The mixture of o-xylene (4.0 g), alcohol (3.0 mmol), and n-dodecane (0.5 mmol) was injected to the pre-reduced catalyst inside the glass tube through the septum inlet. Then, the septum was removed under air, and a magnetic stirrer was put in the tube, followed by inserting the tube inside stainless autoclave with a dead space of 33 cm3. Soon after being sealed, the reactor was flushed with NH3 from a high pressure gas cylinder and charged with 0.4 MPa NH3 at room temperature. The amount of NH3 present in the reactor before heating was 6.7 mmol (2.2 equiv. with respect to the alcohol). Then, the reactor was heated typically at 160C under stirring (150 rpm).

Reference： [1]ACS Catalysis,2013,vol. 3,p. 112 - 117
[2]Catalysis Today,2014,vol. 232,p. 134 - 138

51
[ 830-13-7 ]
[ 5675-51-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: cyclododecanone With maleic anhydride; dihydrogen peroxide In water at 46 - 49℃; for 22h; Stage #2: With hydrogen In methanol; water at 200℃; for 27h; Autoclave; Inert atmosphere;	8 Example 8: Reduction of Crude BV product in water and methanol at 2500psig [00128] A mixture of 60 crude BV product, 24 g methanol, 22 g water and 5 g of 2% Ru on carbon catalyst containing 6% Re and 1.4% Sn were charged to a 300 mL Stainless Steel autoclave containing a thermocouple, cooling coil, baffle and stirrer. The BV product contained 39.4 wt% maleic acid, 29.3 wt% LLON, 1.9 wt% 12- hydroxydodecanoic acid, 3.5 wt% 1,12-dodecanedioic acid, 3.4 wt% mono methyl ester of 1,12-dodecandioic acid, and 12.5 wt% water. The vessel was flushed first with nitrogen followed by hydrogen, and pressurized to 2500psig with hydrogen. Stirring at 1800 rpm was commenced and the reactor was heated to 200°C. The hydrogenation was run for 27 hr. Analysis of the product showed a combined 99.6% conversion of LLON, DDDA and HDDA with 86.7% molar% selectivity to C12LD. Also produced was 1-undecanol (3.5 molar%) along with un-reacted 12- hydroxydodecanoic acid (0.6 molar%) and methyl 12-hydroxydodecanoate (2.4 molar%). The ratio of hydrogenolysis products to C12LD was 0.055.

Reference： [1]Current Patent Assignee: KOCH INDUSTRIES, INC. - WO2013/116029, 2013, A1 Location in patent: Paragraph 00128

52
[ 830-13-7 ]
[ 112-53-8 ]
[ 5675-51-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: cyclododecanone With maleic anhydride; dihydrogen peroxide In water at 46 - 49℃; for 22h; Stage #2: With hydrogen In methanol; water at 195℃; for 24h; Autoclave; Inert atmosphere;	7 Example 7: Reduction of crude BV product in water and methanol [00127] A mixture of 64.1 g crude BV product, 22 g methanol, 22 g water and 5 g of 2% Ru on carbon catalyst containing 6% Re and 0.9% Sn were charged to a 300 mL Stainless Steel autoclave containing a thermocouple, cooling coil, baffle and stirrer. The BV product contained 39.4 wt% maleic acid, 29.3 wt% LLON, 1.9 wt% 12-hydroxydodecanoic acid, 3.5 wt% 1,12-dodecanedioic acid, 3.4 wt% 12- methyl dodecane of 1,12-dodecandioic acid, and 12.5 wt% water. The vessel was flushed first with nitrogen followed by hydrogen and was pressurized to 2000psig with hydrogen. Stirring at 1800 rpm was commenced and the reactor was heated to 195°C. The hydrogenation was run for 24 hr. Analysis of the product showed a combined 99.8 wt% conversion of LLON, DDDA and HDDA with 88.9% molar selectivity to C12LD. Also produced wasl-dodecanol (6.4 molar%) along with un- reacted methyl 12-hydroxydodecanoate.

Reference： [1]Current Patent Assignee: KOCH INDUSTRIES, INC. - WO2013/116029, 2013, A1 Location in patent: Paragraph 00127

53
[ 830-13-7 ]
[ 112-42-5 ]
[ 5675-51-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: cyclododecanone With maleic anhydride; dihydrogen peroxide In water at 46 - 49℃; for 22h; Stage #2: With hydrogen In methanol; water at 200℃; for 24h; Autoclave; Inert atmosphere;	9 Example 9: Reduction of crude BV product in water and methanol at 2000psig [00129] A mixture of 64.1 crude BV product, 24 g methanol, 32 g water, 22 g water and 5 g of 2% Ru on carbon catalyst containing 6% Re and 0.9% Sn were charged to a 300 mL Stainless Steel autoclave containing a thermocouple, cooling coil, baffle and stirrer. The BV product contained 39.4 wt% maleic acid, 29.3 wt% LLON, 1.9 wt% 12-hydroxydodecanoic acid, 3.5 wt% 1,12-dodecanedioic acid, 3.4 wt% mono methyl ester of 1,12-dodecandioic acid, and 12.5 wt% water. The vessel was flushed first with nitrogen followed by hydrogen, and pressurized to 2000psig with hydrogen. Stirring at 1800 rpm was commenced and the reactor was heated to 200°C. The hydrogenation was run for 24 hr. Analysis of the product showed a combined 99.8 wt% conversion of LLON, DDDA and HDDA with 88.8% molar selectivity to C12LD. Also produced was 1-undecanol (6.4 molar%) along with 12- hydroxydodecanoic acid (1.2 molar%) and methyl 12-hydroxydodecanoate (4.9 molar%). The ratio of hydrogenolysis products to C12LD was 0.099.

Reference： [1]Current Patent Assignee: KOCH INDUSTRIES, INC. - WO2013/116029, 2013, A1 Location in patent: Paragraph 00129

54
[ 830-13-7 ]
[ 5675-51-4 ]
[ 71655-36-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: cyclododecanone With maleic anhydride; dihydrogen peroxide In water at 46 - 49℃; for 22h; Stage #2: With hydrogen In methanol; water at 197℃; for 27h; Autoclave; Inert atmosphere;	10 Example 10: Reduction of crude BV product in water and methanol [00130] A mixture of 54.8 g crude BV product, 26 g methanol, 30 g water and 5 g of 2% Ru on carbon catalyst containing 6% Re and 1.2% Sn were charged to a 300 mL Stainless Steel autoclave containing a thermocouple, cooling coil, baffle and stirrer. The BV product contained 39.4 wt% maleic acid, 29.3 wt% LLON, 1.9 wt%, 12-hydroxydodecanoic acid, 3.5 wt% 1,12-dodecanedioic acid, 3.4 wt% methyl 12-hydroxydodecanoate, and 12.5 wt% water. The vessel was flushed first with nitrogen followed by hydrogen, and pressurized to 2000psig with hydrogen. Stirring at 1800 rpm was commenced and the reactor was heated to 197°C. The hydrogenation was run for 27 hr. Analysis of the product showed a combined 99.9 wt% conversion of LLON, DDDA and HDDA with 78% molar selectivity to C12LD. Also produced was 1-dodecanol (2.8 molar%) along with un-reacted 12- hydroxydodecanoic acid (2.5 molar%) and methyl 12-hydroxydodecanoate (8.6 molar%).

Reference： [1]Current Patent Assignee: KOCH INDUSTRIES, INC. - WO2013/116029, 2013, A1 Location in patent: Paragraph 00130

55
[ 830-13-7 ]
[ 505-95-3 ]
[ 5675-51-4 ]
[ 3903-40-0 ]

Yield	Reaction Conditions	Operation in experiment
		[00131] A mixture of 20 g (0.087 mole) 1 ,12-dodecandioic acid, 32 g methanol, 18 g water and 5 g of 5% Ru on carbon catalyst containing 1% Sn are was charged to a 300 mL Stainless Steel autoclave containing a thermocouple, cooling coil, baffle and stirrer. The vessel was flushed first with nitrogen followed by hydrogen, and pressurized to 2500psig with hydrogen. Stirring at 1800 rpm was commenced and the reactor was heated to 230C. The hydrogenation was run for 22 hr. Analysis of the product showed a 98.4 wt% conversion of DDDA with 30.7% molar selectivity to C12LD. Also produced was 1-dodecanol (1.8 molar%) along with the intermediate 12-hydroxydodecanoic acid (14.4 molar%) and the mono methyl ester of 1,12-dodecanedioic acid (38 molar%). It can be seen from the low molar yield to C12LD, the un-reacted intermediate 12-hydroxydodecanoic acid and mono methyl ester of 1 ,2-dodecanedioic acid that the absence of Re had a dramatic effect on the reduction rate to C12LD.

Reference： [1]Patent: WO2013/116029,2013,A1 .Location in patent: Paragraph 00131

56
[ 830-13-7 ]
[ 947-05-7 ]
[ 693-23-2 ]

Yield	Reaction Conditions	Operation in experiment
	With maleic anhydride; dihydrogen peroxide In water at 46 - 49℃; for 22h;	6 Example 6: Baeyer-Villiger oxidation of cyclododecanone (CDDK) [00126] A 100 mL water jacketed 4-necked round-bottomed spherical flask equipped with a thermocouple, a 12°C water cooled spiral surface condenser and magnetic stirrer was employed. A circulating water bath was employed for heating and cooling the jacketed vessel. MAN (5.95, 0.060 mole) and 14.1 g 1,12- dimethyldodecanedioate were added to the vessel at 25°C. The solution was heated to 38°C. H202 (70% in water, 1.94 g, 0.040 mole) was added in three increments at 35°C, followed by raising the temperature to 48-49°C and holding for 1 hr. This maximized the formation of permaleic acid. Solid cyclododecanone (3.55 g, 0.019 mole) was added in three increments. No exothermic heat was observed. The solution became turbid due to maleic acid precipitation after 2 hr run time. The mixture was heated to 46°C and run for an additional 20 hr. Representative sample analysis of the crude product after 22 hr at 46°C showed 97.5 wt% conversion of CDDK and a molar selectivity of 92.0 molar% lauryl lactone based on cyclododecanone. Dodecanedioic acid (7.2 molar%) and 12-hydroxydodecanoic (1.3 molar%) were the other co-products produced from cyclododecanone.

Reference： [1]Current Patent Assignee: KOCH INDUSTRIES, INC. - WO2013/116029, 2013, A1 Location in patent: Paragraph 00126

57
[ 830-13-7 ]
[ 1502-03-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; sodium cyanoborohydride; In ethanol; at 120℃; for 0.0833333h;Microwave irradiation;	The operation was as follows: cyclododecanone (182 mg, 1 mmol), ammonium acetate (116 mg, 1.5 mmol), sodium cyanoborohydride (75 mg, 1.2 mmol) and ethanol (2 mL) were added to a 10 mL microwave reaction tube at a power of 20 W. The reaction was carried out at 120 C for 5 minutes. reaction After completion, the mixture was evaporated to dryness. Dry, evaporated to dryness and used directly in the next reaction. The crude product obtained in the previous step, picolinic acid (133 mg, 1.1 mmol), EDCI (259 mg, 1.4 mmol), DMAP (11 mg, 0.1 mmol) and dichloromethane (2 mL) were added to a 10 mL round bottom flask, and the reaction was stirred overnight at room temperature. After completion of the reaction, it was directly separated through a silica gel column (petroleum ether: ethyl acetate = 10:1) to obtain 186 mg of the desired product 23, yield 65%.

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 245 - 252
[2]Journal of Organic Chemistry,2019,vol. 84,p. 10962 - 10977
[3]Organic Letters,2017,vol. 19,p. 4880 - 4883
[4]Patent: CN109422728,2019,A .Location in patent: Paragraph 0060-0062

58
[ 830-13-7 ]
[ 1502-03-0 ]
[ 1781-77-7 ]

Reference： [1]ChemCatChem,2015,vol. 7,p. 921 - 924

59
[ 830-13-7 ]
[ 145100-50-1 ]
(Z)-cyclododec-1-en-1-yl trifluoromethanesulfonate [ No CAS ]
(1E)-cyclododec-1-en-1-yl trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%		General procedure: A solution of ketone 1 (4.0 mmol, 1.0 equiv) in tetrahydrofuran (THF) (10 mL) was added dropwise to a stirring solution of LDA (1.5 equiv) in THF (3 mL) at -80C. After stirring at -80C for 2 h, a solution of N-(2-pyridyl)triflimide (1.2 equiv)in THF (9 mL) was added. The reaction mixture was stirred for 1 h at the same temperature and then allowed to warm to 0C, followed by stirring for 2 h. The reaction was quenched with saturated aqueous NH4Cl solution, and the reaction mixture was extracted with diethyl ether. The extract was washed with water and brine, dried, and concentrated under reduced pressure. Purification of the residue by flash chromatography (1-5% ethyl acetate in hexane) afforded vinyl triflate 2 in 50-85% yield.

Reference： [1]Chemical and Pharmaceutical Bulletin,2015,vol. 63,p. 393 - 396

60
[ 830-13-7 ]
[ 13139-86-1 ]
[ 63829-20-9 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 10794 - 10797

61
[ 14799-82-7 ]
[ 830-13-7 ]
(cyclopropylmethylene)cyclododecane [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 4028 - 4032
Angew. Chem.,2017,vol. 129,p. 4086 - 4090,5

62
[ 830-13-7 ]
[ 1731-79-9 ]

Reference： [1]Patent: CN107337592,2017,A

63
[ 830-13-7 ]
[ 3903-40-0 ]

Reference： [1]Patent: CN107337592,2017,A

64
[ 18268-68-3 ]
[ 830-13-7 ]
[ 109-77-3 ]
2-amino-4-(3-chloro-4,5-dimethoxyphenyl)-5,6,7,8,9,10, 11,12,13,14-decahydrobenzo[12]annulene-1,3-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With piperidine In acetonitrile Reflux;	12 General procedure for the synthesis of 2-amino-4-phenyl-5,6,7,8,9,10,11,12,13,14-decahydrobenzo[12]annulene-1,3-dicarbonitrile 12 General procedure: A mixture of cyclododecanone (1, 1mmol), aromatic aldehydes (2, 1mmol), malononitrile (3, 2mmol) and piperidine (50mol%) was refluxed in acetonitrile for 4-5h and the reaction progress was monitored by TLC. After completion of the reaction the solvent was removed under vacuum. The crude product was purified by column chromatography using 4:1 (v/v) petroleum ether-ethyl acetate mixture to obtain pure 12.

Reference： [1]Vivek Kumar, Sundaravel; Rani, Mani Anusha; Almansour, Abdulrahman I.; Suresh Kumar, Raju; Athimoolam; Ranjith Kumar, Raju [Tetrahedron, 2018, vol. 74, # 35, p. 4569 - 4577]

65
[ 18268-68-3 ]
[ 830-13-7 ]
[ 109-77-3 ]
2-amino-4-(3-chloro-4,5-dimethoxyphenyl)-5,6,7,8,9,10, 11,12,13,14-decahydrocyclododeca[b]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With ammonium acetate In toluene Reflux;	12 General procedure for the synthesis of 2-amino-4-phenyl-5,6,7,8,9,10,11,12,13,14-decahydrocyclododeca[b]pyridine-3-carbonitriles/carboxylates 4 General procedure: A mixture of cyclododecanone (1, 1mmol), aromatic aldehydes (2, 1mmol), malononitrile/ethyl cyanoacetate (3, 1mmol) and ammonium acetate (1.3 equiv.) in toluene (5mL) was refluxed for 6-7h and the reaction progress was monitored by TLC analysis. After completion of the reaction the solvent was removed under vacuum. The crude product was purified by column chromatography using 4:1 (v/v) petroleum ether-ethyl acetate mixture to obtain pure 4.

Reference： [1]Vivek Kumar, Sundaravel; Rani, Mani Anusha; Almansour, Abdulrahman I.; Suresh Kumar, Raju; Athimoolam; Ranjith Kumar, Raju [Tetrahedron, 2018, vol. 74, # 35, p. 4569 - 4577]

66
[ 61072-56-8 ]
[ 20356-45-0 ]
[ 830-13-7 ]
4-(4-chloro-2-fluorophenyl)-2-(1H-indol-3-yl)-1,4,5,6,7,8,9,10,11,12,13,14-dodecahydrocyclododeca[b]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With ammonium acetate; In ethanol; for 2h;Reflux;	General procedure: A mixture of 3-(1H-indol-3-yl)-3-oxopropanenitrile 3 (0.1 g, 0.543 mmol), aromaticaldehyde 4 (0.543 mmol), cycloalkanone 5 (0.543 mmol) and ammonium acetate (6, 0.1 g, 1.1mmol) was dissolved in ethanol (10 mL) and heated to reflux on a heating mantle for 2 h. Aftercompletion of the reaction as evident from TLC, the reaction mixture was set aside at ambienttemperature for 6-7 h. The precipitate formed was filtered and dried to get the pure indole-cycloalkyl[b]pyridine-3-carbonitriles. The unaromatized product was obtained in the cases wherethe product was precipitated within 2 h.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 2907 - 2915

67
[ 20356-45-0 ]
[ 830-13-7 ]
[ 54881-49-1 ]
4-(2-chloro-3-methoxyphenyl)-2-(1H-indol-3-yl)-1,4,5,6,7,8,9,10,11,12,13,14-dodecahydrocyclododeca[b]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With ammonium acetate; In ethanol; for 2h;Reflux;	General procedure: A mixture of 3-(1H-indol-3-yl)-3-oxopropanenitrile 3 (0.1 g, 0.543 mmol), aromaticaldehyde 4 (0.543 mmol), cycloalkanone 5 (0.543 mmol) and ammonium acetate (6, 0.1 g, 1.1mmol) was dissolved in ethanol (10 mL) and heated to reflux on a heating mantle for 2 h. Aftercompletion of the reaction as evident from TLC, the reaction mixture was set aside at ambienttemperature for 6-7 h. The precipitate formed was filtered and dried to get the pure indole-cycloalkyl[b]pyridine-3-carbonitriles. The unaromatized product was obtained in the cases wherethe product was precipitated within 2 h.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 2907 - 2915

68
[ 1020722-10-4 ]
[ 61072-56-8 ]
[ 830-13-7 ]
2-(5-bromo-1H-indol-3-yl)-4-(4-chloro-2-fluorophenyl)-5,6,7,8,9, 10,11,12,13,14-decahydrocyclododeca[b]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With ammonium acetate; In ethanol; for 2h;Reflux;	General procedure: A mixture of 3-(1H-indol-3-yl)-3-oxopropanenitrile 3 (0.1 g, 0.543 mmol), aromaticaldehyde 4 (0.543 mmol), cycloalkanone 5 (0.543 mmol) and ammonium acetate (6, 0.1 g, 1.1mmol) was dissolved in ethanol (10 mL) and heated to reflux on a heating mantle for 2 h. Aftercompletion of the reaction as evident from TLC, the reaction mixture was set aside at ambienttemperature for 6-7 h. The precipitate formed was filtered and dried to get the pure indole-cycloalkyl[b]pyridine-3-carbonitriles. The unaromatized product was obtained in the cases wherethe product was precipitated within 2 h.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 2907 - 2915

69
[ 294-62-2 ]
[ 1724-39-6 ]
[ 2698-67-1 ]
[ 830-13-7 ]

Yield	Reaction Conditions	Operation in experiment
		In a 100 mL stainless steel autoclave with polytetrafluoroethylene liner, place 0.0026 g (0.002 mmol) of 5,10,15,20-tetraphenyl-2,3,7,8,12,13,17,18 -Cobalt (II) octabromoporphyrin is dispersed in 22.4440g (200mmol) cyclooctane, the reaction kettle is sealed, the temperature is raised to 110C with stirring, and oxygen is introduced to 1.0MPa.The reaction was stirred at 110 , 1.0 MPa oxygen pressure, 800 rpm for 8.0 h.After the reaction was completed, ice water was cooled to room temperature, and 13.1145g (50.00mmol) of triphenylphosphine (PPh) was added to the reaction mixture3), stirring at room temperature for 30 min to reduce the generated peroxide.Using acetone as a solvent, the resulting reaction mixture was made up to 100 mL.Pipette 10mL of the resulting solution, using toluene as an internal standard, and perform gas chromatography analysis; pipette 10mL of the resulting solution, using benzoic acid as an internal standard, and perform liquid chromatography analysis.Conversion rate of cyclooctane was 42.1%, selectivity to cyclooctanol was 45%, selectivity to cyclooctanone was 35%, selectivity to cyclooctylhydroperoxide was 20%, no generation of suberic acid was detected, and no pimelic acid was detected. Of generation.

Reference： [1]Patent: CN111018673,2020,A .Location in patent: Paragraph 0073; 0074

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[ CAS No. 830-13-7 ]

Quality Control of [ 830-13-7 ]

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Product Details of [ 830-13-7 ]

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Application In Synthesis of [ 830-13-7 ]

[ 830-13-7 ] Synthesis Path-Upstream 1~4

[ 830-13-7 ] Synthesis Path-Downstream 1~69

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