CAS号：955959-84-9

CAS号955959-84-9, 是有机发光二极管类化合物, 分子量为323.18, 分子式C18H11BrO, 标准纯度96%, 毕得医药(Bidepharm)提供955959-84-9批次质检（如NMR, HPLC, GC）等检测报告。

4-(4-溴苯基)二苯并[b,d]呋喃 (请以英文为准,中文仅做参考)

4-(4-Bromophenyl)dibenzo[b,d]furan

货号：BD262681 4-(4-Bromophenyl)dibenzo[b,d]furan 标准纯度：, 96%

标准纯度	包装	价格	上海	深圳	天津	武汉	成都	VIP价格	数量

检测信息
批次：
纯度：批次查询可见
COA MS HPLC LC-MS Microanalysis

产品名称 :	4-(4-Bromophenyl)dibenzo[b,d]furan
中文名称 :	4-(4-溴苯基)二苯并[b,d]呋喃(请以英文为准,中文仅做参考)
CAS号 :	955959-84-9
分子式 :	C₁₈H₁₁BrO
线性分子式 :	-
分子量 :	323.18
MDL NO :	MFCD19441306
沸点 :	-
Pubchem ID :	59022098
InChIKey :	RIPZSADLUWTEFQ-UHFFFAOYSA-N

常用 :

SDS-BD262681

2D :

3D :

【用途一】

计算化学

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	19
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	86.86
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	13.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.41
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	5.98
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	6.02
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	4.74
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	5.65
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	5.16

Water Solubility

Log S (ESOL)? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.25
Solubility	0.000183 mg/ml ; 0.000000565 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-6.03
Solubility	0.0003 mg/ml ; 0.000000928 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-8.31
Solubility	0.00000159 mg/ml ; 0.0000000049 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.03 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.73

合成路线：*资料仅供科研用途参考，更多细节请参阅原文出处。

1. 合成：955959-84-9

100124-06-9

589-87-7

955959-84-9

产率

合成条件

实验步骤

93%

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; for 8 h; Inert atmosphere

在氮气氛下，将二苯并呋喃-4-基硼酸（100g，472mmol）溶于1,000mL四氢呋喃（THF）1-溴-4-碘苯（160g，556mmol）和四（三苯基膦）钯（5.45）中。向其中加入g，4.72mmol）并搅拌。加入用水饱和的碳酸钾（78.3g，566mmol），并将混合物在80℃下加热回流8小时。反应完成后，将水加入到反应混合物中，并将混合物用二氯甲烷（DCM）萃取。然后，用无水MgSO 4除去水，过滤并减压浓缩。通过快速柱色谱法纯化由此获得的残余物，得到化合物I-9（142g，93％）。

89%

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 12 h; Reflux; Inert atmosphere

向圆底烧瓶中加入2-二苯并呋喃硼酸20g（94.3mmol），1-溴-4-碘苯26.7g（94.3mmol），加入甲苯（313ml）（mmol）溶解，然后加入117ml水溶液。加入溶解的19.5g（141.5mmol）碳酸钾并搅拌。在此，加入四（三苯基膦）钯1.09g（0.94mmol）并在氮气氛下回流搅拌12小时。反应结束后，将萃取液萃取到乙酸乙酯中，干燥萃取液，用硫酸镁过滤，减压浓缩滤液。通过硅胶柱色谱法纯化产物正己烷/二氯甲烷（9：1体积比），得到27g（89％）目标化合物中间体M-1，为白色固体。

89%

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 12 h; Inert atmosphere; Reflux

将4-二苯并呋喃硼酸20g（94.3mmol）置于圆底烧瓶中，加入1-溴-4-碘苯，26.7g（94.3mmol）并搅拌入117ml水溶液中以溶解碳酸钾和19.5g（141.5mmol）将溶解的溶液加入到甲苯（313ml）中。然后向其中加入四（三苯基膦）钯1.09g（0.94mmol），在氮气氛下回流搅拌12小时。反应结束后，将萃取液浓缩至干，用乙酸乙酯萃取，用硫酸镁过滤，减压下滤液。通过硅胶柱色谱法纯化产物正己烷/二氯甲烷（体积比9：1），得到中间体M-1，为白色固体27g（收率89％）。

89%

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 12 h; Reflux; Inert atmosphere

将4-二苯并呋喃硼酸20g（94.3mmol）和1-溴-4-碘苯26.7g（94.3mmol）的甲苯溶液（313ml）加入圆底烧瓶中并搅拌，加入钾水溶液（117ml）加入碳酸盐19.5g（141.5mmol），然后加入1.09g四（三苯基膦）钯（0.94mmol）并在氮气氛下回流搅拌12小时。反应结束后，用乙酸乙酯萃取反应混合物，用硫酸镁干燥，减压浓缩滤液。所得产物用硅胶柱色谱法纯化，用正己烷/二氯甲烷（体积比9：1）洗脱，得到所需中间体化合物M-1 27g（产率89％），为白色固体。

89%

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene for 12 h; Inert atmosphere; Reflux

将4-苯并呋喃硼酸（4-二苯并呋喃硼酸），20g（94.4mmol），1-溴-4-碘 - 苯28g（99.2mmol）和加入的四（三苯基膦）钯烧瓶1.08g（0.94mmol）溶于240ml甲苯中。加入溶解在120ml 28g（188.8mmol）中的碳酸钾水溶液，在氮气氛下加入120mL乙醇，将其在回流下搅拌12小时。反应后，将萃取液干燥，过滤，然后用乙酸乙酯和亚硫酸镁萃取，减压浓缩滤液。通过硅胶柱色谱法纯化产物正己烷/二氯甲烷（体积比9：1）作为中间体M-9的所需化合物，得到27g（89％收率），为白色固体。

89%

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 12 h; Inert atmosphere; Reflux

将20克（94.3毫摩尔）4-二苯并呋喃硼酸和26.7克（94.3毫摩尔）1-溴-4-碘苯置于圆底烧瓶中，并向其中加入313毫升甲苯以使其溶解。向其中加入通过溶解19.5g（141.5mmol）碳酸钾得到的117ml水溶液，并搅拌该混合物。随后，向其中加入1.09g（0.94mmol）四苯基膦钯。将所得混合物在氮气氛下回流并搅拌12小时。当反应完成时，将所得物用乙酸乙酯萃取。将萃取的溶液用硫酸镁干燥并过滤。将过滤的溶液减压浓缩。随后，用正己烷/二氯甲烷（9：1体积/体积）处理由此获得的产物。通过凝胶柱色谱法纯化，获得27g中间体M-1，为白色固体（收率：89％）。

81%

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; toluene for 10 h; Inert atmosphere; Reflux

[制备实施例1] 4-（4-溴苯基）二苯并呋喃的合成在氩气氛下，将300mL甲苯和150mL 2M碳酸钠水溶液加入到28.3g（100mmol）4-碘溴苯中，22.3g（105mmol）二苯并呋喃-4-硼酸和2.31g（2.00mmol）四（三苯基膦）钯（0），将该混合物加热回流10小时。在反应完成后立即过滤所得物，然后除去水层。用硫酸钠干燥有机层，然后浓缩。将残渣用硅胶柱色谱法精制，得到26.2g的4-（4-溴苯基）二苯并呋喃的白色结晶（收率81％）。

81%

With sodium carbonate In water; toluene for 10 h; Reflux; Inert atmosphere

; 在氩气氛下，将300ml甲苯和150ml浓度为2M的碳酸钠水溶液加入到28.3g（100mmol）4-碘溴苯，22.3g（105mmol）二苯并呋嗪-4-硼酸中。 2.31g（2.00mmol）四（三苯基膦）钯（0），将所得混合物溶液加热回流10小时。反应完成后，立即过滤，除去水层。用硫酸钠干燥有机层后，浓缩。使用硅胶柱对残余物进行色谱纯化，得到26.2g白色晶体状的4-（4-溴苯基）二苯并呋喃（收率：81％）。根据FD-MS分析，将所得白色晶体鉴定为中间体5。

81%