[ CAS No. 100956-66-9 ]

Name: 100956-66-9|N-(3,4-Dimethoxyphenyl)-4-methylbenzenesulfonamide|95%
Brand: Ambeed
SKU: A984464
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Quality Control of [ 100956-66-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 100956-66-9 ]

SDS Specification

Alternatived Products of [ 100956-66-9 ]

Product Details of [ 100956-66-9 ]

CAS No. :	100956-66-9	MDL No. :	N/A
Formula :	C₁₅H₁₇NO₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JRAYUPSJGCRNDR-UHFFFAOYSA-N
M.W :	307.36	Pubchem ID :	276461
Synonyms :

Calculated chemistry of [ 100956-66-9 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.2
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	81.51
TPSA :	73.01 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.36
Log Po/w (XLOGP3) :	2.75
Log Po/w (WLOGP) :	3.7
Log Po/w (MLOGP) :	1.84
Log Po/w (SILICOS-IT) :	2.08
Consensus Log Po/w :	2.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.57
Solubility :	0.0825 mg/ml ; 0.000269 mol/l
Class :	Soluble
Log S (Ali) :	-3.94
Solubility :	0.0354 mg/ml ; 0.000115 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.52
Solubility :	0.000928 mg/ml ; 0.00000302 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.55

Safety of [ 100956-66-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 100956-66-9 ]

* 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 [ 100956-66-9 ]

[ 100956-66-9 ] Synthesis Path-Downstream 1~51

1
[ 98-59-9 ]
[ 6315-89-5 ]
[ 100956-66-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine In dichloromethane at 0℃; for 2h;
48%	In water monomer at 20℃; Sealed tube;
	With pyridine

	Alkaline conditions; Inert atmosphere;
	With pyridine at 0 - 20℃;
	With pyridine In dichloromethane at 0 - 20℃;

Reference： [1]Martin-Matute, Belen; Nevado, Cristina; Cardenas, Diego J.; Echavarren, Antonio M. [Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5757 - 5766]
[2]Bering, Luis; Vogt, Melina; Paulussen, Felix M.; Antonchick, Andrey P. [Organic Letters, 2018, vol. 20, # 13, p. 4077 - 4080]
[3]Proctor; Thomson [Journal of the Chemical Society, 1957, p. 2312] Hackman; Todd [Biochemical Journal, 1953, vol. 55, p. 631,632, 634, 635]
[4]Phetsang, Wanida; Chaturongakul, Soraya; Jiarpinitnun, Chutima [Monatshefte fur Chemie, 2013, vol. 144, # 4, p. 461 - 471]
[5]Liu, Teng; Li, Yongqin; Cheng, Feixiang; Shen, Xianfu; Liu, Jianjun; Lin, Jun [Green Chemistry, 2019, vol. 21, # 13, p. 3536 - 3541]
[6]Chen, Ziyue; Huang, Zhiliang; Jiang, Tengfei; Lei, Aiwen; Qi, Junchao; Wan, Hao; Wang, Daoxin; Yang, Anqi; Yuan, Yong [Angewandte Chemie - International Edition, 2022, vol. 61, # 18][Angew. Chem., 2022, vol. 134, # 18]

2
[ 100956-66-9 ]
[ 1822-73-7 ]
5,6-dimethoxy-1-tosylindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 3h;

Reference： [1]Tohma, Hirofumi; Watanabe, Hiroaki; Takizawa, Shinobu; Maegawa, Tomohiro; Kita, Yasuyuki [Heterocycles, 1999, vol. 51, # 8, p. 1785 - 1788]

3
[ 100956-66-9 ]
[ 106-96-7 ]
[ 533934-31-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2h;

Reference： [1]Martin-Matute, Belen; Nevado, Cristina; Cardenas, Diego J.; Echavarren, Antonio M. [Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5757 - 5766]

4
[ 533934-31-5 ]
[ 100956-66-9 ]
6,7-dimethoxy-1-(toluene-4-sulfonyl)-1,2-dihydro-quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 50%	With hydroquinone; platinum(II) chloride In toluene for 17h; Heating;

Reference： [1]Martin-Matute, Belen; Nevado, Cristina; Cardenas, Diego J.; Echavarren, Antonio M. [Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5757 - 5766]

5
[ 100956-66-9 ]
6,7-dimethoxy-1-(toluene-4-sulfonyl)-1,2-dihydro-quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 91 percent / K₂CO₃ / dimethylformamide / 2 h / 60 °C 2: 48 percent / PtCl₂; hydroquinone / toluene / 17 h / Heating

Reference： [1]Martin-Matute, Belen; Nevado, Cristina; Cardenas, Diego J.; Echavarren, Antonio M. [Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5757 - 5766]

6
[ 100956-66-9 ]
C₁₈H₁₈⁽²⁾HNO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 91 percent / K₂CO₃ / dimethylformamide / 2 h / 60 °C 2: 40 percent / PtCl₂; CD₃OD / toluene / 17 h / Heating

Reference： [1]Martin-Matute, Belen; Nevado, Cristina; Cardenas, Diego J.; Echavarren, Antonio M. [Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5757 - 5766]

7
[ 709-09-1 ]
[ 100956-66-9 ]

Reference： [1]Biochemical Journal,1953,vol. 55,p. 631,632, 634, 635

8
[ 100956-66-9 ]
C₂₀H₂₃NO₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 0 - 20 °C 2.2: 0.5 h / 0 °C 3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 78 °C / Inert atmosphere 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C 7.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

Reference： [1]Mizukami, Megumi; Wada, Koji; Sato, Gen; Ishii, Yusuke; Kawahara, Norio; Nagumo, Shinji [Tetrahedron, 2013, vol. 69, # 20, p. 4120 - 4138]

9
[ 100956-66-9 ]
[ 1431115-94-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 0 - 20 °C 2.2: 0.5 h / 0 °C

Reference： [1]Mizukami, Megumi; Wada, Koji; Sato, Gen; Ishii, Yusuke; Kawahara, Norio; Nagumo, Shinji [Tetrahedron, 2013, vol. 69, # 20, p. 4120 - 4138]

10
[ 100956-66-9 ]
[ 1431116-00-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 0 - 20 °C 2.2: 0.5 h / 0 °C 3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

Reference： [1]Mizukami, Megumi; Wada, Koji; Sato, Gen; Ishii, Yusuke; Kawahara, Norio; Nagumo, Shinji [Tetrahedron, 2013, vol. 69, # 20, p. 4120 - 4138]

11
[ 100956-66-9 ]
[ 1431116-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 0 - 20 °C 2.2: 0.5 h / 0 °C 3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 78 °C / Inert atmosphere

Reference： [1]Mizukami, Megumi; Wada, Koji; Sato, Gen; Ishii, Yusuke; Kawahara, Norio; Nagumo, Shinji [Tetrahedron, 2013, vol. 69, # 20, p. 4120 - 4138]

12
[ 100956-66-9 ]
(3RS,4RS)-N-(3,4-epoxy-5-hydroxypentyl)-N-(3,4-dimethoxyphenyl)-4-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 0 - 20 °C 2.2: 0.5 h / 0 °C 3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 78 °C / Inert atmosphere 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C

Reference： [1]Mizukami, Megumi; Wada, Koji; Sato, Gen; Ishii, Yusuke; Kawahara, Norio; Nagumo, Shinji [Tetrahedron, 2013, vol. 69, # 20, p. 4120 - 4138]

13
[ 100956-66-9 ]
methyl (2E,4RS,5RS)-4,5-epoxy-7-[N-(3,4-dimethoxyphenyl)-4-methylbenzenesulfonamido]-2-heptenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 0 - 20 °C 2.2: 0.5 h / 0 °C 3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 78 °C / Inert atmosphere 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C 7.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere 8.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

Reference： [1]Mizukami, Megumi; Wada, Koji; Sato, Gen; Ishii, Yusuke; Kawahara, Norio; Nagumo, Shinji [Tetrahedron, 2013, vol. 69, # 20, p. 4120 - 4138]

14
[ 100956-66-9 ]
methyl (2E)-3-[(4RS,5RS)-4-hydroxy-7,8-dimethoxy-1-tosyl-2,3,4,5-tetrahydro-1H-2-benzazepin-5-yl]propenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 0 - 20 °C 2.2: 0.5 h / 0 °C 3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 78 °C / Inert atmosphere 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C 7.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere 8.1: dichloromethane / 2 h / 20 °C / Inert atmosphere 9.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -30 °C / Inert atmosphere

Reference： [1]Mizukami, Megumi; Wada, Koji; Sato, Gen; Ishii, Yusuke; Kawahara, Norio; Nagumo, Shinji [Tetrahedron, 2013, vol. 69, # 20, p. 4120 - 4138]

15
[ 100956-66-9 ]
C₁₈H₂₁NO₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 0 - 20 °C 2.2: 0.5 h / 0 °C 3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

Reference： [1]Mizukami, Megumi; Wada, Koji; Sato, Gen; Ishii, Yusuke; Kawahara, Norio; Nagumo, Shinji [Tetrahedron, 2013, vol. 69, # 20, p. 4120 - 4138]

16
[ 100956-66-9 ]
[ 106-95-6 ]
[ 1431115-88-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;	4.2.10 N-Allyl-N-(3,4-dimethoxyphenyl)-4-methylbenzenesulfonamide (18b) According to the conversion of 9c into 13, 18b was obtained in quantitative yield from 17b as colorless cubic: mp 68-69 °C (AcOEt/n-hexane); IR (neat) 3020, 1647 cm-1; EIMS m/z 347 (M+), 192, 160; HRMS m/z calcd for C18H21O4NS: 347.1190, found 347.1161; 1H NMR (270 MHz, CDCl3) δ 7.52 (d, J=8.2 Hz, 2H), 7.25 (d, J=8.2 Hz, 2H), 6.73 (d, J=8.2 Hz, 1H), 6.56-6.50 (m, 2H), 5.75 (ddt, J=16.5, 10.0, 6.6 Hz, 1H), 5.12-5.02 (m, 2H), 4.09-4.17 (d, J=10.0 Hz, 2H), 3.85 (s, 3H), 3.74 (s, 3H), 2.43 (s, 3H); 13C NMR (68 MHz, CDCl3) δ 148.7 (C), 148.6 (C), 143.3 (C), 135.4 (C), 132.9 (CH), 131.8 (C), 129.3 (CH×2), 127.8 (CH×2), 121.0 (CH), 118.6 (CH2), 112.7 (CH), 110.5 (CH), 55.8 (CH3×2), 53.9 (CH2), 21.4 (CH3). Anal. Calcd for C18H21O4NS: C, 62.22; H, 6.09; N, 4.03. Found: C, 62.04; H, 6.11; N, 3.88.

Reference： [1]Mizukami, Megumi; Wada, Koji; Sato, Gen; Ishii, Yusuke; Kawahara, Norio; Nagumo, Shinji [Tetrahedron, 2013, vol. 69, # 20, p. 4120 - 4138]

17
[ 100956-66-9 ]
[ 34711-50-7 ]

Yield	Reaction Conditions	Operation in experiment
58%	With Oxone; sodium nitrite In acetonitrile at 50℃; for 5h; chemoselective reaction;

Reference： [1]Li, Ying-Xiu; Li, Lian-Hua; Yang, Yan-Fang; Hua, Hui-Liang; Yan, Xiao-Biao; Zhao, Lian-Biao; Zhang, Jin-Bang; Ji, Fa-Jin; Liang, Yong-Min [Chemical Communications, 2014, vol. 50, # 69, p. 9936 - 9938]

18
[ 1522-13-0 ]
[ 100956-66-9 ]
6,7-dimethoxy-2,2,4-triphenyl-1-tosyl-1,2-dihydroquinoline [ No CAS ]