CAS號(hào)：955959-84-9

CAS號(hào)955959-84-9, 是有機(jī)發(fā)光二極管類化合物, 分子量為323.18, 分子式C18H11BrO, 標(biāo)準(zhǔn)純度96%, 畢得醫(yī)藥(Bidepharm)提供955959-84-9批次質(zhì)檢（如NMR, HPLC, GC）等檢測(cè)報(bào)告。

4-(4-溴苯基)二苯并[b,d]呋喃 (請(qǐng)以英文為準(zhǔn),中文僅做參考)

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

貨號(hào)：BD262681 4-(4-Bromophenyl)dibenzo[b,d]furan 標(biāo)準(zhǔn)純度：, 96%

標(biāo)準(zhǔn)純度	包裝	價(jià)格	上海	深圳	天津	武漢	成都	VIP價(jià)格	數(shù)量

檢測(cè)信息
批次：
純度：批次查詢可見(jiàn)
COA MS HPLC LC-MS Microanalysis

產(chǎn)品名稱 :	4-(4-Bromophenyl)dibenzo[b,d]furan
中文名稱 :	4-(4-溴苯基)二苯并[b,d]呋喃(請(qǐng)以英文為準(zhǔn),中文僅做參考)
CAS號(hào) :	955959-84-9
分子式 :	C₁₈H₁₁BrO
線性分子式 :	-
分子量 :	323.18
MDL NO :	MFCD19441306
沸點(diǎn) :	-
Pubchem ID :	59022098
InChIKey :	RIPZSADLUWTEFQ-UHFFFAOYSA-N

常用 :

SDS-BD262681

2D :

3D :

【用途一】

計(jì)算化學(xué)

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 ?2

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

合成路線：*資料僅供科研用途參考，更多細(xì)節(jié)請(qǐng)參閱原文出處。

1. 合成：955959-84-9

100124-06-9

589-87-7

955959-84-9

產(chǎn)率

合成條件

實(shí)驗(yàn)步驟

93%

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

在氮?dú)夥障?，將二苯并呋?4-基硼酸（100g，472mmol）溶于1,000mL四氫呋喃（THF）1-溴-4-碘苯（160g，556mmol）和四（三苯基膦）鈀（5.45）中。向其中加入g，4.72mmol）并攪拌。加入用水飽和的碳酸鉀（78.3g，566mmol），并將混合物在80℃下加熱回流8小時(shí)。反應(yīng)完成后，將水加入到反應(yīng)混合物中，并將混合物用二氯甲烷（DCM）萃取。然后，用無(wú)水MgSO 4除去水，過(guò)濾并減壓濃縮。通過(guò)快速柱色譜法純化由此獲得的殘余物，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

向圓底燒瓶中加入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）碳酸鉀并攪拌。在此，加入四（三苯基膦）鈀1.09g（0.94mmol）并在氮?dú)夥障禄亓鲾嚢?2小時(shí)。反應(yīng)結(jié)束后，將萃取液萃取到乙酸乙酯中，干燥萃取液，用硫酸鎂過(guò)濾，減壓濃縮濾液。通過(guò)硅膠柱色譜法純化產(chǎn)物正己烷/二氯甲烷（9：1體積比），得到27g（89％）目標(biāo)化合物中間體M-1，為白色固體。

89%

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

將4-二苯并呋喃硼酸20g（94.3mmol）置于圓底燒瓶中，加入1-溴-4-碘苯，26.7g（94.3mmol）并攪拌入117ml水溶液中以溶解碳酸鉀和19.5g（141.5mmol）將溶解的溶液加入到甲苯（313ml）中。然后向其中加入四（三苯基膦）鈀1.09g（0.94mmol），在氮?dú)夥障禄亓鲾嚢?2小時(shí)。反應(yīng)結(jié)束后，將萃取液濃縮至干，用乙酸乙酯萃取，用硫酸鎂過(guò)濾，減壓下濾液。通過(guò)硅膠柱色譜法純化產(chǎn)物正己烷/二氯甲烷（體積比9：1），得到中間體M-1，為白色固體27g（收率89％）。

89%

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

將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）加入圓底燒瓶中并攪拌，加入鉀水溶液（117ml）加入碳酸鹽19.5g（141.5mmol），然后加入1.09g四（三苯基膦）鈀（0.94mmol）并在氮?dú)夥障禄亓鲾嚢?2小時(shí)。反應(yīng)結(jié)束后，用乙酸乙酯萃取反應(yīng)混合物，用硫酸鎂干燥，減壓濃縮濾液。所得產(chǎn)物用硅膠柱色譜法純化，用正己烷/二氯甲烷（體積比9：1）洗脫，得到所需中間體化合物M-1 27g（產(chǎn)率89％），為白色固體。

89%

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

將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）鈀燒瓶1.08g（0.94mmol）溶于240ml甲苯中。加入溶解在120ml 28g（188.8mmol）中的碳酸鉀水溶液，在氮?dú)夥障录尤?20mL乙醇，將其在回流下攪拌12小時(shí)。反應(yīng)后，將萃取液干燥，過(guò)濾，然后用乙酸乙酯和亞硫酸鎂萃取，減壓濃縮濾液。通過(guò)硅膠柱色譜法純化產(chǎn)物正己烷/二氯甲烷（體積比9：1）作為中間體M-9的所需化合物，得到27g（89％收率），為白色固體。

89%

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

將20克（94.3毫摩爾）4-二苯并呋喃硼酸和26.7克（94.3毫摩爾）1-溴-4-碘苯置于圓底燒瓶中，并向其中加入313毫升甲苯以使其溶解。向其中加入通過(guò)溶解19.5g（141.5mmol）碳酸鉀得到的117ml水溶液，并攪拌該混合物。隨后，向其中加入1.09g（0.94mmol）四苯基膦鈀。將所得混合物在氮?dú)夥障禄亓鞑嚢?2小時(shí)。當(dāng)反應(yīng)完成時(shí)，將所得物用乙酸乙酯萃取。將萃取的溶液用硫酸鎂干燥并過(guò)濾。將過(guò)濾的溶液減壓濃縮。隨后，用正己烷/二氯甲烷（9：1體積/體積）處理由此獲得的產(chǎn)物。通過(guò)凝膠柱色譜法純化，獲得27g中間體M-1，為白色固體（收率：89％）。

81%

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

[制備實(shí)施例1] 4-（4-溴苯基）二苯并呋喃的合成在氬氣氛下，將300mL甲苯和150mL 2M碳酸鈉水溶液加入到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）鈀（0），將該混合物加熱回流10小時(shí)。在反應(yīng)完成后立即過(guò)濾所得物，然后除去水層。用硫酸鈉干燥有機(jī)層，然后濃縮。將殘?jiān)霉枘z柱色譜法精制，得到26.2g的4-（4-溴苯基）二苯并呋喃的白色結(jié)晶（收率81％）。

81%

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

; 在氬氣氛下，將300ml甲苯和150ml濃度為2M的碳酸鈉水溶液加入到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）鈀（0），將所得混合物溶液加熱回流10小時(shí)。反應(yīng)完成后，立即過(guò)濾，除去水層。用硫酸鈉干燥有機(jī)層后，濃縮。使用硅膠柱對(duì)殘余物進(jìn)行色譜純化，得到26.2g白色晶體狀的4-（4-溴苯基）二苯并呋喃（收率：81％）。根據(jù)FD-MS分析，將所得白色晶體鑒定為中間體5。

81%