diethyl 3,4-bis(bromomethyl)thieno[2,3-b]thiophene-2,5-dicarboxylate | 908028-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: diethyl 3,4-bis(bromomethyl)thieno[2,3-b]thiophene-2,5-dicarboxylate
• 英文别名: ethyl 3,4-bis(bromomethyl)-5-(ethyloxycarbonyl)thieno[2,3-b]thiophene-2-carboxylate
• CAS: 908028-71-7
• 化学式: C₁₄H₁₄Br₂O₄S₂
• 分子量: 470.203
• InChiKey: ZGFFGRYBPDSUJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 3,4-bis(bromomethyl)thieno[2,3-b]thiophene-2,5-dicarboxylate 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 3,11,15,17-Tetrathiatetracyclo[11.5.1.15,9.016,19]icosa-1(18),5(20),6,8,13,16(19)-hexaene-14,18-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and structures of thieno[2,3-b]thiophene incorporated [3.3]dithiacyclophanes. Enhanced first hyperpolarizability in an unsymmetrically polarized cyclophane

  摘要：

  Dithiacyclophanes incorporating thieno[2,3-b]thiophene have been synthesized. in order to investigate the nonlinear optical properties of donor-acceptor cyclophane 7. Cyclophane 7 displayed significantly higher first hyperpolarizability beta (21.6 x 10(-30) esu) compared to model 10 (9.58 x 10(-30) esu). Relatively higher in 7 presumably arises from an extra electron redistribution arising from through-space charge transfer, a feature lacking in 10. Moreover. the thermal decomposition temperature of 7 (300 degrees C) is higher than that reported for the NLO prototype DAN (295 degrees C). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.098
• 作为产物：
  描述：

  3,4-二甲基(2,3-b)-噻吩-2,5-二羧酸二乙酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以79%的产率得到diethyl 3,4-bis(bromomethyl)thieno[2,3-b]thiophene-2,5-dicarboxylate
  参考文献：
  名称：

  Oxa-bridged cyclophanes featuring thieno[2,3-b]thiophene and C2-symmetric binol or bis-naphthol rings: synthesis, structures, and conformational studies

  摘要：

  Oxa-bridged cyclophanes 4/6 and 8/10 featuring thieno[2,3-b]thiophene ring and binol or bis-naphthol have been synthesized. The Structures are assigned by 2D NMR data and the identity of 4 is also independently established by a single X-ray crystallography. From dynamic NMR analysis, the Arrhenius energy of activation Delta G(#) for bridge inversions in 4 and 6 was calculated to be 15.3 and 12.9 kcal/mol, respectively. A higher Delta G(#) for 4, relative to the ester free 6 is attributable to the steric compression stemming from C2/C5 ester substituents to the bridge inversion processes. While the methylene bridges undergo inversion in 4 and 6, the naphthyl-naphthyl pseudo-rotation appears to be restricted even at higher temperatures. This is Supported by retention of the optical purity of the chiral (-) 4 under thermal condition. For the case of bis-naphthol cyclophane 8, we observed the flipping of both the -OCH2- and the naphthyl-CH2-naphthyl bridges with Delta G(#) of ca. 11.4 kcal/mol. However, the ester free cyclophane 10 remained conformationally mobile even at -55 degrees C and its AGO was assumed to be <11.4 kcal/mol. The presence of an extra -CH2- linker in bis-naphthol cyclophanes 8/10 renders them relatively more conformationally mobile compared to binol cyclophanes 4/6, possessing a rigid naphthyl-naphthyl geometry. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.076

文献信息

• Facile one‐pot, three‐component synthesis of novel bis(heterocycles) incorporating thieno[2,3‐<i>b</i>]thiophenes via Michael addition reaction
  作者：Elshimaa M. Eid、Huwaida M. E. Hassaneen、Ismail A. Abdelhamid、Ahmed H. M. Elwahy

  DOI：10.1002/jhet.3945

  日期：2020.5

  A synthesis of novel series of bis(2‐amino‐3‐cyano‐4H‐chromene), bis(2‐amino‐3‐cyanopyrano[3,2‐c]chromene), bis(6‐amino‐5‐cyano‐1,4‐dihydropyrano[2,3‐c]pyrazole), and bis(2,7‐diamino‐3,4,6‐tricyanopyrazolo[1,5‐a]pyridine) derivatives linked to thieno[2,3‐b]thiophene core via ether or ester linkages was reported. The formation of the target compounds presumably proceeds through a three component reaction

  新型双（2-氨基-3-氰基-4 H-色烯），双（2-氨基-3-氰基吡喃并[3,2- c ]色烯），双（6-氨基-5-氰基）的合成-1,4-二氢吡喃[2,3- c ]吡唑）和bis（2,7-二氨基-3,4,6-三氰基吡唑并[1,5- a ]吡啶）衍生物与噻吩并[2,3-报道了通过醚或酯键的b ]噻吩核。目标化合物的形成大概是通过适当的双醛与2 M的三组分反应进行的 分别是丙二腈和相应的活性亚甲基化合物；在哌啶作为碱性催化剂存在下，二恶烷中的二甲酮，4-羟基香豆碱，5-甲基-2,4-二氢-3H-吡唑-3-酮或氰基甲基吡唑在回流下。新的化合物的化学结构已通过几种光谱工具阐明。
• Hantzsch-like synthesis of novel bis(hexahydroacridine-1,8-diones), bis(tetrahydrodipyrazolo[3,4-<i>b</i>:4′,3′-<i>e</i>]pyridines), and bis(pyrimido[4,5-<i>b</i>]quinolines) incorporating thieno[2,3-<i>b</i>]thiophenes
  作者：Elshimaa M Eid、Huwaida M E Hassaneen、Ahmed H M Elwahy、Ismail A Abdelhamid

  DOI：10.1177/1747519820917886

  日期：2020.11

  A novel series of bis(hexahydroacridine-1,8-diones), bis(tetrahydrodipyrazolo[3,4-b:4′,3′-e]pyridines), and bis(pyrimido[4,5-b]quinolines) incorporating a thieno[2,3-b]thiophene core via ether or ester linkages is prepared via a Hantzsch-like reaction.

  一系列新的双（六氢吖啶-1,8-二酮）、双（四氢二吡唑并[3,4-b:4',3'-e]吡啶）和双（嘧啶并[4,5-b]喹啉）结合通过类似 Hantzsch 的反应制备通过醚或酯键连接的噻吩并 [2,3-b] 噻吩核。
• Hantzsch-like synthesis of bis(sulfanediyl)bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones) linked to arene or heteroarene cores utilizing bis(sulfanediyl)bis(6-aminopyrimidin-4-ones) as precursors
  作者：Hadeer M. Diab、Mostafa E. Salem、Ismail A. Abdelhamid、Ahmed H. M. Elwahy

  DOI：10.1007/s00706-021-02825-4

  日期：2021.8

  A novel series of bis(sulfanediyl)bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones) which are linked to benzene, pyridine, or thieno[4,5-d]thiophene cores were prepared to via multicomponent reaction of bis(sulfanediyl))bis(6-aminopyrimidin-4(1H)-ones) with two equivalents of both dimedone and the appropriate aromatic aldehyde. The target molecules were alternatively prepared via the bis-alkylation

  通过多组分制备了一系列与苯、吡啶或噻吩并[4,5- d ]噻吩核相连的新型双（硫烷二基）双（四氢嘧啶并[4,5 - b ]喹啉-4,6-二酮）的反应双（硫））双（6-氨基嘧啶-4（1 ħ） -酮）与两个双甲酮的两个当量和适当的芳族醛。或者通过合适的 5-芳基-2-硫代六氢嘧啶并[4,5 - b ]喹啉-4,6-二酮与相应的二溴化合物的双烷基化反应制备目标分子。 图形摘要
• Synthesis, reactions and DFT calculations of novel bis(chalcones) linked to a thienothiophene core through an oxyphenyl bridge
  作者：Osama M. Sayed、H. Moustafa、Ahmed E. M. Mekky、Ahmad M. Farag、Ahmed H. M. Elwahy

  DOI：10.1039/c5ra27322f

  日期：——

  A synthesis of novel isomeric bis(chalcones) based-thienothiophene and study of their synthetic utilities as building blocks for novel bis(dihydroisoxazoles), bis(dihydropyrazoles) and bis(dihydropyrimidines) each linked to a thienothiophene core through an oxyphenyl bridge is reported. Density functional theory (DFT) calculations at the B3LYP/6-31G level of theory have been carried out to investigate

  报道了新型的基于异双（查尔酮）的噻吩并噻吩的合成及其作为新的双（二氢异恶唑），双（二氢吡唑）和双（二氢嘧啶）的结构单元的合成工具的研究，这些双（二氢异恶唑），双（二氢吡唑）和双（二氢嘧啶）通过氧苯基桥连接到噻吩并噻吩核上。已经进行了B3LYP / 6-31G理论水平的密度泛函理论（DFT）计算，以研究新型异构查耳酮7和10的平衡几何构型。此外，计算了总能量，HOMO和LUMO的能量以及Mullikan原子电荷。另外，两个π-等电子查尔酮7和10的偶极矩和取向 已测定了它们的含量，并研究了它们与水合肼形成二氢吡唑的相互作用。
• 3,4-Bis(bromomethyl)thieno[2,3-<i>b</i>]thiophene: Versatile Precursors for Novel Bis(triazolothiadiazines), Bis(quinoxalines), Bis(dihydrooxadiazoles), and Bis(dihydrothiadiazoles)
  作者：Osama M. Sayed、Ahmed E. M. Mekky、Ahmad M. Farag、Ahmed H. M. Elwahy

  DOI：10.1002/jhet.2373

  日期：2016.7

  A synthesis of novel bis(triazolothiadiazines) 11, 12, 13, 14, bis(quinoxalines) 16 and 17, bis(thiadiazoles) 24 and 25, and bis(oxadiazole) 31, which are linked to the thieno[2,3‐b]thiophene core via phenoxymethyl group, was reported. Thus, reaction of the bis(α‐bromoketones) 6 and 7 with the corresponding 4‐amino‐3‐mercapto‐1,2,4‐triazole derivatives 8, 9, 10 in ethanol–DMF mixture in the presence

  新颖二的合成（triazolothiadiazines）11，12，13，14，双（喹喔啉）16和17，双（噻二唑）24和25，和双（恶二唑）31，其被连接于噻吩并[2,3-报道了通过苯氧甲基的b ]噻吩核。因此，（在双反应α -bromoketones）6和7与相应的4-氨基-3-巯基-1,2,4-三唑衍生物8，9，10在在三乙胺几滴的作为催化剂存在下回流，得到乙醇-DMF混合物中的新颖双（5,6-二氢小号-三唑并[3,4- b ]噻二嗪）11，12，13，14中60–72％的产量。双（喹喔啉）16和17还通过在哌啶为催化剂的条件下，在回流乙腈中6和7与邻苯二胺15的反应，以高收率合成了唯一的产物。双（醛硫代半脲酮）20和21的环化用乙酸酐制得的双（4,5-二氢-1,3,4-噻二唑基）衍生物24和25的收率很高。通过在回流的乙酸酐中将适当的双（N-苯基reflux）29环化3 h，可以以67％的产率获得双（5-苯基-2