[ CAS No. 100717-32-6 ] {[proInfo.proName]}

Name: 100717-32-6|3-Cyclohexyl-1H-indole|95+%
Brand: Ambeed
SKU: A272617
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Quality Control of [ 100717-32-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 100717-32-6 ]

Product Details of [ 100717-32-6 ]

CAS No. :	100717-32-6	MDL No. :	MFCD03069640
Formula :	C₁₄H₁₇N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HYXQPIDRIDLWRT-UHFFFAOYSA-N
M.W :	199.29	Pubchem ID :	11298575
Synonyms :

Safety of [ 100717-32-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 100717-32-6 ]

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

Downstream synthetic route of [ 100717-32-6 ]

[ 100717-32-6 ] Synthesis Path-Downstream 1~50

1
[ 120-72-9 ]
[ 108-93-0 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With C₁₈H₁₈Cl₄N₂Ni₂O₂; potassium 2-methylbutan-2-olate In neat (no solvent) at 150℃; for 24h;
67%	With C₃₇H₃₆Cl₂NPRuS₂; potassium hydroxide at 135℃; for 18h; Inert atmosphere; Sealed tube;
56%	With potassium hydroxide In neat (no solvent) at 150℃; for 18h; regioselective reaction;	General procedures for the preparation of the products General procedure: To a stirred mixture of the corresponding indole (1, 1 mmol) and KOH (1.3 mmol, 73 mg), was added the corresponding alcohol (2 or 4, 3 mmol). The resulting mixture was stirred at 150C during 3 or 24 hours. The resulting mixture was quenched with deionised water and extracted with EtOEt (3 × 5 mL). The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The product was usually purified by crystallization or chromatography on silica gel (hexane/ethyl acetate) to give the corresponding products 3 or 5.

	With 4-methylisopropylbenzene; potassium 1-cyclohexyl methanoate; nickel
96 %Spectr.	With potassium phosphate; tris(triphenylphosphine)ruthenium(II) chloride; bis[2-(diphenylphosphino)phenyl] ether In neat (no solvent) at 165℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Hu, Miao; Jiang, Yong; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu; Hu, Xinquan; Jin, Liqun [New Journal of Chemistry, 2021, vol. 45, # 22, p. 10057 - 10062]
[2]Biswas, Nandita; Sharma, Rahul; Srimani, Dipankar [Advanced Synthesis and Catalysis, 2020, vol. 362, # 14, p. 2902 - 2910]
[3]Cano, Rafael; Yus, Miguel; Ramón, Diego J. [Tetrahedron Letters, 2013, vol. 54, # 26, p. 3394 - 3397]
[4]Pratt; Botimer [Journal of the American Chemical Society, 1957, vol. 79, p. 5348]
[5]Putra, Anggi Eka; Takigawa, Kei; Tanaka, Hatsuki; Ito, Yoshihiko; Oe, Yohei; Ohta, Tetsuo [European Journal of Organic Chemistry, 2013, # 28, p. 6344 - 6354]

2
[ 1027208-32-7 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol

Reference： [1]Tokuyama; Watanabe; Hayashi; Kurokawa; Peng; Fukuyama [Synlett, 2001, # 9, p. 1403 - 1406]

3
[ 64126-56-3 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
0.14 g	With hydrogen In ethanol at 20℃; for 2h;
	With 10% Pd/C; hydrogen at 20℃; for 2h;

Reference： [1]Grimster, Neil P.; Gauntlett, Carolyn; Godfrey, Christopher R. A.; Gaunt, Matthew J. [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3125 - 3129]
[2]Chen, Wen-Liang; Gao, Ya-Ru; Mao, Shuai; Zhang, Yan-Lei; Wang, Yu-Fei; Wang, Yong-Qiang [Organic Letters, 2012, vol. 14, # 23, p. 5920 - 5923]

4
[ 120-72-9 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper(II) acetate / palladium(II) acetate / dimethylformamide; dimethylsulfoxide / 18 h / 70 °C 2: 0.14 g / hydrogen / palladium on carbon / ethanol / 2 h / 20 °C

Reference： [1]Grimster, Neil P.; Gauntlett, Carolyn; Godfrey, Christopher R. A.; Gaunt, Matthew J. [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3125 - 3129]

5
[ 110-83-8 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper(II) acetate / palladium(II) acetate / dimethylformamide; dimethylsulfoxide / 18 h / 70 °C 2: 0.14 g / hydrogen / palladium on carbon / ethanol / 2 h / 20 °C

Reference： [1]Grimster, Neil P.; Gauntlett, Carolyn; Godfrey, Christopher R. A.; Gaunt, Matthew J. [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3125 - 3129]

6
[ 79202-15-6 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 97 percent / H₂ / 10 percent Pd/C / ethanol / 72 h / 100 °C / 38786.1 Torr 2.1: 57 percent / aq. KOH; BnEt₃NCl / CH₂Cl₂ / Heating 3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.2: 73 percent / HMPA / tetrahydrofuran; hexane / -78 - 20 °C 4.1: AIBN / acetonitrile / 0.25 h / 100 °C 5.1: Raney-Ni / ethanol

Reference： [1]Tokuyama; Watanabe; Hayashi; Kurokawa; Peng; Fukuyama [Synlett, 2001, # 9, p. 1403 - 1406]

7
[ 104167-26-2 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 57 percent / aq. KOH; BnEt₃NCl / CH₂Cl₂ / Heating 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 73 percent / HMPA / tetrahydrofuran; hexane / -78 - 20 °C 3.1: AIBN / acetonitrile / 0.25 h / 100 °C 4.1: Raney-Ni / ethanol

Reference： [1]Tokuyama; Watanabe; Hayashi; Kurokawa; Peng; Fukuyama [Synlett, 2001, # 9, p. 1403 - 1406]

8
[ 552-89-6 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 84 percent / KF / tetrahydrofuran / 2 h / 40 °C 2.1: 97 percent / H₂ / 10 percent Pd/C / ethanol / 72 h / 100 °C / 38786.1 Torr 3.1: 57 percent / aq. KOH; BnEt₃NCl / CH₂Cl₂ / Heating 4.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 4.2: 73 percent / HMPA / tetrahydrofuran; hexane / -78 - 20 °C 5.1: AIBN / acetonitrile / 0.25 h / 100 °C 6.1: Raney-Ni / ethanol

Reference： [1]Tokuyama; Watanabe; Hayashi; Kurokawa; Peng; Fukuyama [Synlett, 2001, # 9, p. 1403 - 1406]

9
[ 375372-41-1 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: AIBN / acetonitrile / 0.25 h / 100 °C 2: Raney-Ni / ethanol

Reference： [1]Tokuyama; Watanabe; Hayashi; Kurokawa; Peng; Fukuyama [Synlett, 2001, # 9, p. 1403 - 1406]

10
[ 375372-32-0 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 73 percent / HMPA / tetrahydrofuran; hexane / -78 - 20 °C 2.1: AIBN / acetonitrile / 0.25 h / 100 °C 3.1: Raney-Ni / ethanol

Reference： [1]Tokuyama; Watanabe; Hayashi; Kurokawa; Peng; Fukuyama [Synlett, 2001, # 9, p. 1403 - 1406]

11
[ 120-72-9 ]
[ 108-94-1 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 4-n-butyl-4-(3-sulfopropyl)thiomorpholinium 1,1-dioxide trifluoromethane sulfonate In neat (no solvent) at 100℃; for 1h;
71%	With triethylsilane; trichloroacetic acid In toluene at 70℃;
71%	With triethylsilane; trichloroacetic acid In toluene at 70℃; for 2h; Inert atmosphere;

62%	With 5% Pd(II)/C(eggshell); hydrogen; trifluoroacetic acid In dichloromethane at 0℃;	General procedure from 2-substituted indoles 1 to 2,3-disubstituted indoles 2 A solution of 2-substituted indole 1 (2 mmol) and the aldehyde or ketone 3 (2.2 mmol) in CH2Cl2 (10 mL) was added dropwise to a stirred, ice-cold solution of TFA (3.0 mmol) and 5% Pd/C (30 mg) in CH2Cl2 (5 mL) under H2 (1 atm) atmosphere. The mixture was stirred at 0 oC and monitored by TLC until completed (4-8 h). After evaporation of the solvent under reduced pressure, the product was purified by flash chromatography on silica gel using EtOAc/hexanes (1/5) as eluent
62%	With dimethylmonochlorosilane In acetonitrile at 25℃; for 12h; Inert atmosphere;	General procedure: reductive etherification of carbonyl compounds with alcohols General procedure: To a mixture of carbonyl (0.25 mmol) and alcohol (0.275 mmol, 1.1 equiv) in acetonitrile (0.5 mL) wasadded chlorodimethylsilane (0.275 mmol, 1.1 equiv) under argon. The reaction mixture was stirred atroom temperature (ca. 25 °C) for 12 h. The reaction was then quenched by adding a drop of aqueousNaHCO3 solution under air. The resulting mixture was dried over Na2SO4 and concentrated underreduced pressure. The crude product was purified by column chromatography on silica gel(pentane/DCM or pentane/MTBE).
49%	With bismuth (III) nitrate pentahydrate In neat (no solvent) at 140℃; for 5h; Sealed tube;
	With triethylsilane; trichloroacetic acid In toluene at 70℃; Inert atmosphere;
	With triethylsilane; trichloroacetic acid In toluene at 70℃; for 3h;
	With triethylsilane; trichloroacetic acid In toluene at 70℃; for 3h; Inert atmosphere;
	With triethylsilane; trichloroacetic acid In toluene at 70℃; for 2h; Schlenk technique; Inert atmosphere;

Reference： [1]Taheri, Amir; Lai, Bingbing; Cheng, Cheng; Gu, Yanlong [Green Chemistry, 2015, vol. 17, # 2, p. 812 - 816]
[2]Location in patent: body text Rizzo, John R.; Alt, Charles A.; Zhang, Tony Y. [Tetrahedron Letters, 2008, vol. 49, # 48, p. 6749 - 6751]
[3]Su, Yi-Ming; Hou, Yu; Yin, Feng; Xu, Yue-Ming; Li, Yan; Zheng, Xiaoqi; Wang, Xi-Sheng [Organic Letters, 2014, vol. 16, # 11, p. 2958 - 2961]
[4]Cao, Liang-Liang; Wang, Duo-Sheng; Jiang, Guo-Fang; Zhou, Yong-Gui [Tetrahedron Letters, 2011, vol. 52, # 22, p. 2837 - 2839]
[5]Lee, Yong Ho; Morandi, Bill [Synlett, 2017, vol. 28, # 18, p. 2425 - 2428]
[6]Kilic; Bayindir; Erdogan; Agopcan Cinar; Konuklar; Bali; Saracoglu; Aviyente [New Journal of Chemistry, 2017, vol. 41, # 18, p. 9674 - 9687]
[7]Mu, Xin; Chen, Shujun; Zhen, Xingliang; Liu, Guosheng [Chemistry - A European Journal, 2011, vol. 17, # 22, p. 6039 - 6042]
[8]Beaud, Rodolphe; Nandi, Raj Kumar; Perez-Luna, Alejandro; Guillot, Régis; Gori, Didier; Kouklovsky, Cyrille; Ghermani, Nour-Eddine; Gandon, Vincent; Vincent, Guillaume [Chemical Communications, 2017, vol. 53, # 43, p. 5834 - 5837]
[9]Yu, Lemao; Zhong, Yuan; Yu, Jicong; Gan, Lu; Cai, Zhengjun; Wang, Rui; Jiang, Xianxing [Chemical Communications, 2018, vol. 54, # 19, p. 2353 - 2356]
[10]Wang, Xin; Lou, Chenhao; Lv, Leiyang; Li, Zhiping [Organic Letters, 2021, vol. 23, # 15, p. 5978 - 5982]

12
[ 1262588-92-0 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride In methanol; water at 20℃; for 2h;

Reference： [1]Nadres, Enrico T.; Lazareva, Anna; Daugulis, Olafs [Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 471 - 483]

13
[ 100717-32-6 ]
[ 1262588-67-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: palladium diacetate; sodium carbonate; CyJohnPhos / N,N-dimethyl acetamide / 24 h / 125 °C / Inert atmosphere

Reference： [1]Nadres, Enrico T.; Lazareva, Anna; Daugulis, Olafs [Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 471 - 483]

14
[ 100717-32-6 ]
[ 74-88-4 ]
[ 172983-86-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 3-cyclohexyl-1H-indole With sodium hydride In N,N-dimethyl-formamide Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
	Stage #1: 3-cyclohexyl-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;

Reference： [1]Nadres, Enrico T.; Lazareva, Anna; Daugulis, Olafs [Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 471 - 483]
[2]Mu, Xin; Chen, Shujun; Zhen, Xingliang; Liu, Guosheng [Chemistry - A European Journal, 2011, vol. 17, # 22, p. 6039 - 6042]

15
[ 931-48-6 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; cyclohexane / -78 °C 1.2: 1 h / -78 °C 2.1: tetrabutyl-ammonium chloride; palladium diacetate; sodium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 15 h / 100 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water / 2 h / 20 °C

Reference： [1]Nadres, Enrico T.; Lazareva, Anna; Daugulis, Olafs [Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 471 - 483]

16
[ 148991-61-1 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutyl-ammonium chloride; palladium diacetate; sodium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 15 h / 100 °C / Inert atmosphere 2: hydrogenchloride / methanol; water / 2 h / 20 °C

Reference： [1]Nadres, Enrico T.; Lazareva, Anna; Daugulis, Olafs [Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 471 - 483]

17
[ 120-72-9 ]
[ 110-83-8 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: indole; cyclohexene With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 110℃; for 0.333333h; Flow reactor; Green chemistry; Stage #2: With palladium on activated charcoal; hydrogen In ethanol at 20℃; for 3h; Green chemistry; regioselective reaction;
	Multi-step reaction with 2 steps 1: palladium diacetate; trifluoroacetic acid; oxygen / dimethyl sulfoxide / 14 h / 60 °C 2: 10% Pd/C; hydrogen / 2 h / 20 °C / 760.05 Torr

Reference： [1]Gemoets, Hannes P. L.; Hessel, Volker; Nol, Timothy [Organic Letters, 2014, vol. 16, # 21, p. 5800 - 5803]
[2]Chen, Wen-Liang; Gao, Ya-Ru; Mao, Shuai; Zhang, Yan-Lei; Wang, Yu-Fei; Wang, Yong-Qiang [Organic Letters, 2012, vol. 14, # 23, p. 5920 - 5923]

18
[ 100717-32-6 ]
methyl 4-phenyl-2-oxo-3-butenoate [ No CAS ]
[ 1428236-58-1 ]
C₂₅H₂₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96 % ee	Stage #1: methyl 4-phenyl-2-oxo-3-butenoate With copper(II) bis(trifluoromethanesulfonate); [3aS-[2(3'aR,8'aS),3a,8a]]methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] In toluene at 0℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: 3-cyclohexyl-1H-indole In toluene at 0℃; for 12h; Inert atmosphere; Schlenk technique; Overall yield = 92 %; enantioselective reaction;

Reference： [1]Cheng, Hong-Gang; Lu, Liang-Qiu; Wang, Tao; Yang, Qing-Qing; Liu, Xiao-Peng; Li, Yang; Deng, Qiao-Hui; Chen, Jia-Rong; Xiao, Wen-Jing [Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3250 - 3254][Angew. Chem., 2013, vol. 125, # 11, p. 3332 - 3336,5]

19
[ 1431934-77-8 ]
[ 100717-32-6 ]
[ 1431934-68-7 ]

Yield	Reaction Conditions	Operation in experiment
23 mg	With tetrabutyl-ammonium chloride; sodium formate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 27℃; Inert atmosphere;

Reference： [1]Wang, Christy; Sperry, Jonathan [Chemical Communications, 2013, vol. 49, # 39, p. 4349 - 4351]

20
[ 120-72-9 ]
[ 108-94-1 ]
[ 1504-16-1 ]
[ 64126-56-3 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 41% 2: 20% 3: 5%	With palladium(II) trifluoroacetate; oxygen; bis[2-(diphenylphosphino)phenyl] ether In toluene at 140℃; for 8h; regioselective reaction;

Reference： [1]Chen, Shanping; Liao, Yunfeng; Zhao, Feng; Qi, Hongrui; Liu, Saiwen; Deng, Guo-Jun [Organic Letters, 2014, vol. 16, # 6, p. 1618 - 1621]

21
[ 100717-32-6 ]
[ 1504-16-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With palladium(II) trifluoroacetate; oxygen; bis[2-(diphenylphosphino)phenyl] ether In toluene at 140℃; for 30h;

Reference： [1]Chen, Shanping; Liao, Yunfeng; Zhao, Feng; Qi, Hongrui; Liu, Saiwen; Deng, Guo-Jun [Organic Letters, 2014, vol. 16, # 6, p. 1618 - 1621]

22
[ 100717-32-6 ]
[ 935-50-2 ]
C₂₁H₂₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With zinc trifluoromethanesulfonate In toluene at 25℃; for 24h;

Reference： [1]Shu, Chang; Liao, Li-Hua; Liao, Yi-Jun; Hu, Xiao-Yan; Zhang, Yong-Hong; Yuan, Wei-Cheng; Zhang, Xiao-Mei [European Journal of Organic Chemistry, 2014, vol. 2014, # 21, p. 4467 - 4471]

23
[ 100717-32-6 ]
N-(4,4-dimethoxycyclohexa-2,5-dien-1-ylidene)-4-methylbenzenesulfonamide [ No CAS ]
C₂₈H₃₀N₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With zinc trifluoromethanesulfonate In toluene at 25℃; for 24h;

24
[ 100717-32-6 ]
[ 87751-69-7 ]
C₂₉H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With bis(η3-allyl-μ-chloropalladium(II)); N-((1S,2R)-2-((R)-(4-bromophenyl)sulfinyl)-1,2-diphenylethyl)-2-(diphenylphosphino)benzamide; caesium carbonate In dichloromethane at 40℃; Inert atmosphere; Schlenk technique; enantioselective reaction;

Reference： [1]Chen, Li-Yan; Yu, Xiao-Ye; Chen, Jia-Rong; Feng, Bin; Zhang, Hong; Qi, Ying-Hua; Xiao, Wen-Jing [Organic Letters, 2015, vol. 17, # 6, p. 1381 - 1384]

25
[ 100717-32-6 ]
[ 87751-69-7 ]
C₂₉H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate; 1,2-bis-(diphenylphosphino)ethane In dichloromethane at 40℃; Inert atmosphere; Schlenk technique;

Reference： [1]Chen, Li-Yan; Yu, Xiao-Ye; Chen, Jia-Rong; Feng, Bin; Zhang, Hong; Qi, Ying-Hua; Xiao, Wen-Jing [Organic Letters, 2015, vol. 17, # 6, p. 1381 - 1384]

26
[ 67-56-1 ]
[ 100717-32-6 ]
C₁₅H₂₀N₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	Stage #1: 3-cyclohexyl-1H-indole With 1-(azidosulfonyl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In 1,2-dichloro-ethane at 40℃; for 0.0833333h; Inert atmosphere; Stage #2: methanol In 1,2-dichloro-ethane at 40℃; for 0.333333h; Inert atmosphere;
20%	Stage #1: 3-cyclohexyl-1H-indole With 1-(azidosulfonyl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In 1,2-dichloro-ethane at 40℃; for 0.0833333h; Inert atmosphere; Stage #2: methanol In 1,2-dichloro-ethane at 40℃; for 0.333333h;	3 Example 3 Under nitrogen protection,0.5 mmol of 2,3-dimethylimidazole-1-sulfonyl azide trifluoromethanesulfonate2 was added to a solution of 0.5 mmol of 3-cyclohexylindole 1e in 4 ml of 1,2-dichloroethane.The reaction solution was placed in an oil bath and the temperature was controlled at 40 degrees Celsius.After stirring the reaction for 5 minutes, 2.5 mmol of methanol was added.After continuing the reaction at 40 ° C for 20 minutes, return to room temperature and distill off the solvent under reduced pressure.The residue was purified by silica gel column chromatography using ethyl acetate and petroleum ether as eluent.The corresponding 2-sulfonimidoindoline 3e was obtained in a yield of 20%.

Reference： [1]Shen, Mei-Hua; Xu, Ke; Sun, Chu-Han; Xu, Hua-Dong [Organic Letters, 2015, vol. 17, # 15, p. 3654 - 3657]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN105153011, 2018, B Location in patent: Paragraph 0031; 0032; 0033

27
[ 496-15-1 ]
[ 108-94-1 ]
[ 120-72-9 ]
[ 63405-13-0 ]
[ 100717-32-6 ]
1,3-dicyclohexyl-1H-indole [ No CAS ]
1,3,5-tricyclohexyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 38% 2: 13% 3: 12% 4: 13% 5: 4%	With bismuth (III) nitrate pentahydrate In acetonitrile at 120℃; for 3h; Sealed tube;
1: 30% 2: 21% 3: 25% 4: 3% 5: 12%	With Cl₄Zn In acetonitrile at 120℃; Sealed tube;
1: 12% 2: 26% 3: 28% 4: 15% 5: 6%	With Cl₄Zn at 140℃; Sealed tube;

1: 25% 2: 26% 3: 4% 4: 2% 5: 19%

With zinc trifluoromethanesulfonate In acetonitrile at 120℃; for 3h; Sealed tube;

Reference： [1]Bayindir, Sinan; Erdogan, Esra; Kilic, Haydar; Aydin, Omer; Saracoglu, Nurullah [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 5, p. 1589 - 1594]
[2]Bayindir, Sinan; Erdogan, Esra; Kilic, Haydar; Aydin, Omer; Saracoglu, Nurullah [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 5, p. 1589 - 1594]
[3]Bayindir, Sinan; Erdogan, Esra; Kilic, Haydar; Aydin, Omer; Saracoglu, Nurullah [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 5, p. 1589 - 1594]
[4]Bayindir, Sinan; Erdogan, Esra; Kilic, Haydar; Aydin, Omer; Saracoglu, Nurullah [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 5, p. 1589 - 1594]

28
[ 67-56-1 ]
[ 100717-32-6 ]
[ 558-13-4 ]
methyl 3-cyclohexyl-1H-indole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With Ru(2,2'-bipyridine)3(PF₆)2*H₂O; diisopropylamine at 20℃; for 10h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;

Reference： [1]Yang, Qing-Qing; Marchini, Marianna; Xiao, Wen-Jing; Ceroni, Paola; Bandini, Marco [Chemistry - A European Journal, 2015, vol. 21, # 50, p. 18052 - 18056]

29
[ 100717-32-6 ]
[ 37051-70-0 ]
N-((5aR,10bS)-10b-cyclohexyl-6,10b-dihydro-5aH-benzofuro[2,3-b]indol-3-yl)-4-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid In acetonitrile at 0℃; for 12h; enantioselective reaction;

Reference： [1]Liao, Lihua; Shu, Chang; Zhang, Minmin; Liao, Yijun; Hu, Xiaoyan; Zhang, Yonghong; Wu, Zhijun; Yuan, Weicheng; Zhang, Xiaomei [Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10471 - 10475][Angew. Chem., 2014, # 39, p. 10639 - 10643,5]

30
[ 100717-32-6 ]
[ 143121-73-7 ]
9-cyclohexyl-1,3-diphenyl-9H-pyrrolo[1,2-a]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With copper(ll) bromide In chloroform at 20℃; for 1h;

Reference： [1]Zhang, Minmin; Liao, Lihua; Yu, Shuowen; Liao, Yijun; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 965 - 978]

31
[ 100717-32-6 ]
[ 100-39-0 ]
1-benzyl-3-cyclohexyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: 3-cyclohexyl-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 1h;

Reference： [1]Yu, Lemao; Zhong, Yuan; Yu, Jicong; Gan, Lu; Cai, Zhengjun; Wang, Rui; Jiang, Xianxing [Chemical Communications, 2018, vol. 54, # 19, p. 2353 - 2356]

32
[ 100717-32-6 ]
[ 92250-13-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrabutyl-ammonium chloride; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -10℃; Green chemistry;	6.2 Example 6: Synthesis of 3-substituted oxindole (3-cyclohexyl-1-hydrogen-oxindole) Add the starting material 6 (40 mg, 0.2 mmol), tetrabutylammonium chloride hydrate (67 mg,0.24 mmol) to the same reactor, and then add 1.5 mL of the solvent dichloromethane to control the reaction temperature to -10 °C. A0.5 mL solution of [bis(trifluoroacetoxy)iodo]benzene (103 mg, 0.24 mmol) in dichloromethane was added dropwise, and the reaction was quickly confirmed by TLC. The reaction was quenched by the addition of 10 mL of saturated sodium bicarbonate solution. Extraction with dichloromethane (2X 3.0 mL), The organic phases were combined and washed with saturated brine. Dry over anhydrous sodium sulfate, Concentrated under reduced pressure, The obtained concentrate was separated by silica gel column chromatography ( petroleum ether / ethyl acetate, 5:1) The yield of 3-cyclohexyl-1-hydrogen-oxindole is 38.3 mg, the yield is 81%, and the chemical structural formula is:
81%	With tetrabutyl-ammonium chloride; water; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 25℃;

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN108101830, 2018, A Location in patent: Paragraph 0100; 0101; 0102; 0103
[2]Liang, Peng; Zhao, Hang; Zhou, Tingting; Zeng, Kaiyun; Jiao, Wei; Pan, Yang; Liu, Yazhou; Fang, Dongmei; Ma, Xiaofeng; Shao, Huawu [Advanced Synthesis and Catalysis, 2021, vol. 363, # 14, p. 3532 - 3538]

33
[ 100717-32-6 ]
2-allyl-3-cyclohexyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; N-chloro-succinimide / dichloromethane / 0.25 h / 0 °C 2: dichloromethane / 1 h / 20 °C

Reference： [1]Saya, Jordy M.; van Wordragen, Ellen D. H.; Orru, Romano V. A.; Ruijter, Eelco [European Journal of Organic Chemistry, 2019, vol. 2019, # 31-32, p. 5156 - 5160]

34
[ 100717-32-6 ]
C₁₄H₁₆ClN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; triethylamine In dichloromethane at 0℃; for 0.25h;

Reference： [1]Saya, Jordy M.; van Wordragen, Ellen D. H.; Orru, Romano V. A.; Ruijter, Eelco [European Journal of Organic Chemistry, 2019, vol. 2019, # 31-32, p. 5156 - 5160]

35
[ 100717-32-6 ]
1-benzyl-4-(benzyloxy)-5-cyclopropyl-5-hydroxypyrrolidin-2-one [ No CAS ]
(3'S)-1-benzyl-3'-(benzyloxy)-10-cyclohexyl-8,9-dihydro-7H-spiro[pyrido[1,2-a]indole-6,2'-pyrrolidin]-5'-one [ No CAS ]
(3'S,9R)-1'-benzyl-3'-(benzyloxy)-10-cyclohexyl-7,8-dihydro-6H-spiro[pyrido[1,2-a]indole-9,2'-pyrrolidin]-5'-one [ No CAS ]
1-benzyl-4-(benzyloxy)-5-((3aS,8bR)-8b-cyclohexyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-3-yl)-1,5-dihydro-2H-pyrrol-2-one [ No CAS ]
(3'S)-1-benzyl-3'-(benzyloxy)-10-cyclohexyl-8,9-dihydro-7H-spiro[pyrido[1,2-a]indole-6,2'-pyrrolidin]-5'-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 46 % de 2: 5.3% 3: 24%	With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 13h; Inert atmosphere; diastereoselective reaction;

Reference： [1]Ryder, Greg M.; Wille, Uta; Willis, Anthony C.; Pyne, Stephen G. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 29, p. 7025 - 7035]

36
[ 100717-32-6 ]
1-(1,1,2,2-tetrafluoro-2-phenoxyethyl)-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one [ No CAS ]
3-cyclohexyl-2-(1,1,2,2-tetrafluoro-2-phenoxyethyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium L-ascorbate In methanol; water at 20℃; for 0.0833333h; Inert atmosphere;

Reference： [1]Rahimidashaghoul, Kheironnesae; Klimánková, Iveta; Hubálek, Martin; Korecký, Michal; Chvojka, Matúš; Pokorný, Daniel; Matoušek, Václav; Fojtík, Lukáš; Kavan, Daniel; Kukačka, Zdeněk; Novák, Petr; Beier, Petr [Chemistry - A European Journal, 2019, vol. 25, # 69, p. 15779 - 15785]

37
[ 100717-32-6 ]
[ 4393-06-0 ]
(S)-3-cyclohexyl-2-(1-phenylallyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; magnesium(II) perchlorate In dichloromethane at 40℃; Schlenk technique; Inert atmosphere; enantioselective reaction;

Reference： [1]Clarke, Aimee K.; Donald, James R.; Rossi-Ashton, James A.; Taylor, Richard J. K.; Unsworth, William P.; You, Shu-Li; Zheng, Chao [Angewandte Chemie - International Edition, 2020, vol. 59, # 19, p. 7598 - 7604][Angew. Chem., 2020, vol. 132, p. 7668 - 7674,7]

38
[ 100717-32-6 ]
[ 4393-06-0 ]
3-cyclohexyl-2-(1-phenylallyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']diphenyl-4-en)-dibenzo[b,f]azepine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; magnesium(II) perchlorate In dichloromethane at 40℃; Schlenk technique; Inert atmosphere;

39
[ 100717-32-6 ]
[ 96-32-2 ]
C₁₇H₂₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With disodium hydrogenphosphate; [4,4′-di-tert-butyl-2,2′-bipyridine]bis[5-methyl-2-(4-methyl-2pyridinyl)phenyl]iridium(III) hexafluorophosphate In 1,2-dichloro-ethane at 20℃; for 20h; Inert atmosphere; Irradiation; regioselective reaction;

Reference： [1]Hu, Fengchi; Liu, Qinglong; Liu, Yuchang; Pan, Zhiqiang; Shang, Wenbin; Xia, Chengfeng [Chemical Communications, 2020, vol. 56, # 36, p. 4930 - 4933]

40
[ 120-72-9 ]
[ 108-94-1 ]
[ 1504-16-1 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 78% 2: 6%	With palladium 10% on activated carbon; 10% Nb2O5/AC; 2,3-dimethyl-buta-1,3-diene In water; toluene at 130℃; for 24h; Molecular sieve; Inert atmosphere;
1: 55% 2: 45%	With palladium 10% on activated carbon; 10% Nb2O5/AC In water; toluene at 130℃; for 24h; Molecular sieve; Inert atmosphere;

Reference： [1]Ban, Kazuho; Sajiki, Hironao; Sawama, Yoshinari; Yamamoto, Yuta [Organic and biomolecular chemistry, 2020, vol. 18, # 20, p. 3898 - 3902]
[2]Ban, Kazuho; Sajiki, Hironao; Sawama, Yoshinari; Yamamoto, Yuta [Organic and biomolecular chemistry, 2020, vol. 18, # 20, p. 3898 - 3902]

41
[ 15121-84-3 ]
[ 100717-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: C₃₇H₃₆Cl₂NPRuS₂; potassium hydroxide / toluene / 24 h / 135 °C / Inert atmosphere; Sealed tube 2: C₃₇H₃₆Cl₂NPRuS₂; potassium hydroxide / 18 h / 135 °C / Inert atmosphere; Sealed tube
	Multi-step reaction with 2 steps 1: C₃₇H₃₆Cl₂NPRuS₂; potassium hydroxide / 48 h / 135 °C / Inert atmosphere; Sealed tube 2: C₃₇H₃₆Cl₂NPRuS₂; potassium hydroxide / 18 h / 135 °C / Inert atmosphere; Sealed tube

Reference： [1]Biswas, Nandita; Sharma, Rahul; Srimani, Dipankar [Advanced Synthesis and Catalysis, 2020, vol. 362, # 14, p. 2902 - 2910]
[2]Biswas, Nandita; Sharma, Rahul; Srimani, Dipankar [Advanced Synthesis and Catalysis, 2020, vol. 362, # 14, p. 2902 - 2910]

42
[ 100717-32-6 ]
[ 106-51-4 ]
(5aR,10bS)-10b-cyclohexyl-6,10b-dihydro-5aH-benzofuro[2,3-b]indol-2-ol [ No CAS ]
(5aS,10bR)-10b-cyclohexyl-6,10b-dihydro-5aH-benzofuro[2,3-b]indol-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76 % ee	With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In acetonitrile at -20 - 0℃; Overall yield = 55 percent; enantioselective reaction;	General procedure of enantioselective [3+2] coupling of 3-substituted indoles 1 with Quinones 2 General procedure: 3-Substituted indole 1 (0.20 mmol) and Quinones 2 (0.30 mmol) were placed in a flame-dried vial equipped with a magnetic stirring bar. Then 2 mL of CH3CN was added to dissolve the mixture. The solution was cooled to 0 oC. Afterwards chiral phosphoric acid (R)-PA8 (0.01 mmol, 10 mol%) was added. The reaction mixture was stirred at -20 oC until no starting material was detected by TLC. The solvent was evaporated and the residue was subjected to chromatography (silica gel, Petroleum ether/ EtOAc: 5/1 to 4/1) to afford the desired product 3.

Reference： [1]Lan, Wei-qiao; Liao, Li-hua; Liu, Fang-yi; Lu, Zhen-yu; Wang, Jun-yi; Zhang, Xiao-mei [Tetrahedron Letters, 2021, vol. 76]

43
[ 100717-32-6 ]
2-(2-(tert-butylperoxy)-2-phenylethyl)-1,3-diphenylpropane-1,3-dione [ No CAS ]
(10-cyclohexyl-9-(3-cyclohexyl-1H-indol-2-yl)-6-phenyl-8,9-dihydropyrido[1,2-a]indol-7-yl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With trifluorormethanesulfonic acid In acetonitrile at 25℃; for 24h; Sealed tube;

Reference： [1]Wang, Xin; Lou, Chenhao; Lv, Leiyang; Li, Zhiping [Organic Letters, 2021, vol. 23, # 15, p. 5978 - 5982]

44
[ 100717-32-6 ]
2-(2-(tert-butylperoxy)-2-phenylethyl)-1,3-diphenylpropane-1,3-dione [ No CAS ]
(10-cyclohexyl-6-phenylpyrido[1,2-a]indol-7-yl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With trifluorormethanesulfonic acid In acetonitrile at 100℃; for 5h; Sealed tube;

Reference： [1]Wang, Xin; Lou, Chenhao; Lv, Leiyang; Li, Zhiping [Organic Letters, 2021, vol. 23, # 15, p. 5978 - 5982]

45
[ 100717-32-6 ]
C₃₈H₃₅NP₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 24 h / 20 °C / Inert atmosphere; Schlenk technique 1.2: 2 h / Inert atmosphere; Schlenk technique 2.1: n-butyllithium / diethyl ether / 4 h / 20 °C / Inert atmosphere; Schlenk technique 2.2: 24 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 2.3: 2 h / 50 °C 3.1: n-butyllithium / diethyl ether / 1 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 3.2: 5 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

Reference： [1]Liu, Yao; Ma, Xufeng; Mi, Puke; Wang, Zhichao; Zhang, Jun; Zhao, Xing [Journal of Organometallic Chemistry, 2022, vol. 958]

46
[ 100717-32-6 ]
2-diphenylphosphino-3-cyclohexylindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 24 h / 20 °C / Inert atmosphere; Schlenk technique 1.2: 2 h / Inert atmosphere; Schlenk technique 2.1: n-butyllithium / diethyl ether / 4 h / 20 °C / Inert atmosphere; Schlenk technique 2.2: 24 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 2.3: 2 h / 50 °C

Reference： [1]Liu, Yao; Ma, Xufeng; Mi, Puke; Wang, Zhichao; Zhang, Jun; Zhao, Xing [Journal of Organometallic Chemistry, 2022, vol. 958]

47
[ 100717-32-6 ]
[ 30354-18-8 ]
1-[(dimethylamino)-methyl]−3-cyclohexylindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 3-cyclohexyl-1H-indole; N,N-dimethyl(methylene)ammonium chloride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: With triethylamine In tetrahydrofuran for 2h; Inert atmosphere; Schlenk technique;	Synthesis of 4b : Dimethylmethyleneammonium chloride (1.20 g, 12.8 mmol) and 3-cyclohexylindole 4a (1.27 g, 6.4 mmol) were added to tetrahydrofuran (20 mL). The mixture was stirred for 24 h at ambient temperature, gradually forming a yellow suspension. Triethylamine (1.8 mL, 13.0 mmol) was added to the mixture, and stirring was continued for 2 h. The solvent was removed in vacuo, affording a white residue. The residue was suspended in water (60.0 mL), and the product was extracted with dichloromethane (2 ×20 mL). The combined organic layers were dried over an- hydrous MgSO 4 , and the solvent was removed in vacuo to afford 4b (1.50 g, 91%) as a pale-yellow oil. 1H NMR (400 MHz, CDCl3) δ= 7.72 (d, J = 7.9 Hz, 1H), 7.48 (d, J = 8.2 Hz, 1H), 7.27 (t, J = 7.5 Hz, 1H), 7.17 (t, J = 7.5 Hz, 1H), 6.97 (s, 1H), 4.73 (s, 2H), 2.94 -2.91 (m, 1H), 2.36 (s, 6H), 2.20 (d, J = 6.6 Hz, 2H), 1.94 -1.85 (m, 3H), 1.60 -1.50 (m, 4H), 1.39 (m, 1H); 13CNMR (100 MHz, CDCl3) δ= 160.27, 150.29, 146.87, 145.15, 144.45, 142.23, 141.61, 132.77, 91.45, 90.86, 65.66, 58.23, 57.01, 49.85, 49.47, 48.52; HRMS (EI): m/z [M] + calcd for C17H24N2 + : 256.1939, found: 256.1940.

Reference： [1]Liu, Yao; Ma, Xufeng; Mi, Puke; Wang, Zhichao; Zhang, Jun; Zhao, Xing [Journal of Organometallic Chemistry, 2022, vol. 958]

48
[ 100717-32-6 ]
[ 685-87-0 ]
diethyl 2-(3-cyclohexyl-1H-indole-2-yl)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With N,N-diphenyl-4-methoxyaniline In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Irradiation;

Reference： [1]Gao, Xuebo; Chang, Rong; Rao, Junxin; Hao, Danyang; Zhang, Zhuxia; Zhou, Cong-Ying; Guo, Zhen [Journal of Organic Chemistry, 2022, vol. 87, # 12, p. 8198 - 8202]

49
[ 100717-32-6 ]
[ 24424-99-5 ]
N-Boc-3-cyclohexylindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-dimethylaminopyridine; triethylamine In dichloromethane at 23℃; for 2h;

Reference： [1]Wu, Jintao; Peng, Zehui; Shen, Tong; Liu, Zhong-Quan [Advanced Synthesis and Catalysis, 2022, vol. 364, # 15, p. 2565 - 2570]

50
[ 100717-32-6 ]
(3,4-dihydroisoquinolin-2-ium-2-yl)(tosyl)amide [ No CAS ]
C₃₀H₃₃N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With 3,3,6,6,9,9-hexamethyl-1,2,4,5,7,8-hexaoxacyclononane In propan-2-one at -10℃; for 2h;	8 Example 8: Preparation of 9-cyclohexyl-8-p-toluenesulfonyl-4H-indoline[1,2,4]triazolo[5,1-a]isoquinolin-9-ol Methyl-8-p-toluenesulfonyl-4H-benzo[f]indole[1,2,4]triazolo[5,1-a]isoquinolin-9-ol Take a 10 mL reaction tube, add 3-cyclohexyl indole (40 mg, 0.2 mmol), azomethine imine (72 mg, 0.24 mmol), and acetone solution of peroxyacetone (3 mL) in turn, and stir reaction 2 at -10 °C hours, then spin to dryness, pass through the column with petroleum ether:ethyl acetate=5:1,85 mg of the target compound was obtained as a white solid with a yield of 83%.Its NMR and mass spectrometry data are as follows:

Reference： [1]Current Patent Assignee: SHAOXING UNIVERSITY - CN114014859, 2022, A Location in patent: Paragraph 0093-0095; 0116

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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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

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

[ CAS No. 100717-32-6 ] {[proInfo.proName]}

Quality Control of [ 100717-32-6 ]

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Product Details of [ 100717-32-6 ]

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Application In Synthesis of [ 100717-32-6 ]

[ 100717-32-6 ] Synthesis Path-Downstream 1~50

Technical Information

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Indoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 100717-32-6 ]