6-bromo-2,3,7-trimethylbenzo[b]thiophene | 208840-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 6-bromo-2,3,7-trimethylbenzo[b]thiophene
• 英文别名: 6-Bromo-2,3,7-trimethyl-1-benzothiophene
• CAS: 208840-59-9
• 化学式: C₁₁H₁₁BrS
• 分子量: 255.178
• InChiKey: BAKRDUUIEPZDQT-UHFFFAOYSA-N

物化性质

• 沸点：
  340.4±37.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-2,3,7-trimethylbenzo[b]thiophene 在 正丁基锂 、 硼酸三丁酯 、 palladium diacetate 、 2-硝基碘苯 、 碳酸氢钠 作用下， 以 乙醚 、 正己烷 、 水 、 丙酮 为溶剂， 反应 3.5h， 以25%的产率得到2,3,7-trimethylbenzo[b]thiophene
  参考文献：
  名称：

  钯催化交叉偶联伊莎贝尔合成的6-（2'-硝基苯基）苯并[ b ]噻吩的还原环化反应合成新的甲基化噻吩并[2,3- a ]和[3,2- b ]咔唑

  摘要：

  新的甲基化噻吩并[2,3-a]和[3,2-b]咔唑（5）（R = H）的合成是通过钯催化的交叉偶联，分子内还原环化反应来实现的。通过将6-硼代甲基苯并[ b ]噻吩中间体（2）与2-溴或碘硝基苯进行Suzuki交叉偶联，得到环化前体6-（（2'-硝基苯基）苯并[b]噻吩（3）。硼化中间体（2）的制备是通过溴-锂交换，然后进行硼金属转移，并使用Pd（OAc）2原位偶联，从而从6-溴苯并[ b ]硫代苯（ 1）到环化前体（3）。在还原环化步骤中，还获得了N-乙基噻吩并咔唑（5）（R ＝ Et）。为了避免形成亚磷酸三乙酯的量和反应时间，已经进行了一些实验。

  DOI：

  10.1002/jhet.5570380334
• 作为产物：
  描述：

  2,3,7-trimethylbenzo[b]thiophene 在 溴 作用下， 生成 6-bromo-2,3,7-trimethylbenzo[b]thiophene
  参考文献：
  名称：

  Palladium-catalyzed borylation and Suzuki coupling (BSC) to obtain β-substituted dehydroamino acid derivatives

  摘要：

  Several benzo[b]thienyidehydroamino acids were prepared by one-pot palladium-catalyzed borylation and Suzuki coupling (BSC) from bromobenzo[b]thiophenes containing EDG (OMe or Me), as the component to be borylated with pinacolborane, and pure stereoisomers of beta-bromodehydroamino acid derivatives. To our knowledge it is the first time that the BSC reaction involves a non aromatic system. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01473-4

文献信息

• Synthesis of β-Benzo[b]thienyldehydrophenylalanine Derivatives by One-Pot Palladium-Catalyzed Borylation and Suzuki Coupling (BSC) and Metal-Assisted Intramolecular Cyclization - Studies of Fluorescence and Antimicrobial Activity
  作者：Ana S. Abreu、Paula M. T. Ferreira、Maria-João R. P. Queiroz、Isabel C. F. R. Ferreira、Ricardo C. Calhelha、Letícia M. Estevinho

  DOI：10.1002/ejoc.200500040

  日期：2005.7

  (Z)-N-(tert-butoxycarbonyl)-p-(2,3,5-trimethylbenzo[b]thien-6-yl)dehydrophenylalanine with Pd(OAc) 2 and Cu(OAc) 2 in DMF at 160 °C gave two indole derivatives (1:3), the major product resulting from isomerization and cyclization and the minor product resulting from direct cyclization (thienoindole). Carrying out the reaction at 100 °C gave the same products in similar amounts. Use of the methyl ester of (Z)-N-

  钯催化硼化和铃木偶联（BSC）在一锅法中成功应用于苯并[b]噻吩系列中几种β-取代的脱氢苯丙氨酸的合成，同时保持了起始材料的立体化学。带有邻位 EDG（OMe 或 Me）的溴苯并 [b] 噻吩用作要与频哪醇硼烷硼化的组分，而 β-溴代氢苯丙氨酸的纯立体异构体用作其他 Suzuki 偶联组分。用Pd(OAc) 2 和Cu(OAc)处理获得的(Z)-N-(叔丁氧基羰基)-对-(2,3,5-三甲基苯并[b]噻吩-6-基)脱氢苯丙氨酸甲酯2 在 DMF 中于 160 °C 得到两种吲哚衍生物 (1:3)，主要是异构化和环化产生的产物，而直接环化产生的次要产物（噻吩并吲哚）。在 100 °C 下进行反应得到相似量的相同产物。使用 (Z)-N-(叔丁氧基羰基)-β-(2,3,7-三甲基苯并[b]噻吩-6-基)脱氢苯丙氨酸的甲酯作为起始原料仅得到一种产物，其由异构化和在 100 °C 下环化。对两种环化
• Synthesis and antimicrobial activity studies of ortho-chlorodiarylamines and heteroaromatic tetracyclic systems in the benzo[b]thiophene series
  作者：Maria-João R.P. Queiroz、Isabel C.F.R. Ferreira、Yannick De Gaetano、Gilbert Kirsch、Ricardo C. Calhelha、Letícia M. Estevinho

  DOI：10.1016/j.bmc.2006.06.035

  日期：2006.10

  ortho-Chlorodiarylamines in the 2,3,7-trimethylbenzo[b]thiophene series were prepared in high yields (70-85%) by C-N palladium-catalyzed cross-coupling using P(t-Bu)(3) as ligand and NaOt-Bu as base. A palladium-assisted C-C intramolecular cyclization of the coupling products gave thienocarbazoles and the dechlorinated diarylamines. Studies of antimicrobial activity of the compounds obtained, against

  通过以P（t-Bu）（3）为配体和NaOt的CN钯催化的交叉偶联，以高收率（70-85％）制备2,3,7-三甲基苯并[b]噻吩系列的邻氯二芳基胺-Bu为基础。偶联产物的钯辅助CC分子内环化得到噻吩并咔唑和脱氯二芳基胺。对获得的化合物对代表性细菌（大肠杆菌，铜绿假单胞菌，蜡状芽孢杆菌和枯草芽孢杆菌）和真菌（白色念珠菌）的抗菌活性进行了研究。我们还在生物学测定中包括了我们先前制备的一些吡啶衍生物，并且有可能建立一些结构-活性关系（SAR）。
• Synthesis of new methylated thieno[2,3-<i>a</i>] and [3,2-<i>b</i>]carbazoles by reductive cyclization of 6-(2′-Nitrophenyl)benzo[<i>b</i>]thiophenes obtained by palladium-catalyzed cross-coupling isabel
  作者：C. F. R. Ferreira、Maria-João R. P. Queiroz、Gilbert Kirsch

  DOI：10.1002/jhet.5570380334

  日期：2001.5

  [3,2-b]carbazoles (5) (R=H) was achieved by a palladium-catalyzed cross-coupling, intramolecular reductive cyclization sequence of reactions. The cyclization precursors 6-(2′-nitrophenyl)benzo[b]thiophenes (3) were obtained by Suzuki cross-coupling of 6-boronated methylbenzo[b]thiophenes intermediates (2) with 2-bromo or iodonitrobenzene. The boronated intermediates (2) were prepared via bromine-lithium

  新的甲基化噻吩并[2,3-a]和[3,2-b]咔唑（5）（R = H）的合成是通过钯催化的交叉偶联，分子内还原环化反应来实现的。通过将6-硼代甲基苯并[ b ]噻吩中间体（2）与2-溴或碘硝基苯进行Suzuki交叉偶联，得到环化前体6-（（2'-硝基苯基）苯并[b]噻吩（3）。硼化中间体（2）的制备是通过溴-锂交换，然后进行硼金属转移，并使用Pd（OAc）2原位偶联，从而从6-溴苯并[ b ]硫代苯（ 1）到环化前体（3）。在还原环化步骤中，还获得了N-乙基噻吩并咔唑（5）（R ＝ Et）。为了避免形成亚磷酸三乙酯的量和反应时间，已经进行了一些实验。
• Synthesis and photochromic behaviour of new methyl induced linear and angular thieno-2H-chromenes
  作者：Maria-João R.P. Queiroz、Paula M.S. Plasencia、Roger Dubest、Jean Aubard、Robert Guglielmetti

  DOI：10.1016/s0040-4020(03)00262-x

  日期：2003.3

  New methyl induced linear and angular thieno-2H-chromenes 4, 5 and 6 were prepared by reaction of new methylated 6-hydroxybenzo[b]thiophenes 2 (a, b and c) and propargylic alcohols 3a and 3b, using acidic Alumina Brockmann I as catalyst and drying agent. Compounds 2 were prepared in good to excellent yields in a 'one pot' three step reaction from the corresponding bromo compounds 1. The photochromic behaviour of compounds 4, 5 and 6b was evaluated with the aid of a classical set of spectrokinetic parameters, and compared to reference compounds that are benzoannellated in the 5,6 and 6,7 positions of the chromene (naphthopyrans) and also to thieno-2H-chromenes 7 and 8, previously prepared, which are analogues of 5a. The resistance to fatigue (photodegradation) under continuous irradiation was also evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Tandem palladium-catalyzed borylation and Suzuki coupling (BSC) to thienocarbazole precursors
  作者：Isabel C.F.R. Ferreira、Maria-João R.P. Queiroz、Gilbert Kirsch

  DOI：10.1016/s0040-4039(03)00952-3

  日期：2003.6

  Substituted 2-methyl-2'-nitro diaryl compounds in the benzo[h]thiophene series were prepared by palladium-catalyzed, two-step. one-pot borylation/Suzuki coupling (BSC) reaction in good to high yields. The borylation reaction was performed on methylated 6-bromobenzo[b]thiophenes using pinacolborane and was followed by in situ Suzuki coupling with substituted (CF3, OMe) 2-bromonitrobenzenes. The compounds obtained were cyclized to the corresponding ring A substituted thienocarbazoles which can have biological activity or/and be used as biomarkers due to their fluorescence properties and possible DNA intercalation. (C) 2003 Elsevier Science Ltd. All rights reserved.