2-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy)acetic acid | 540803-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy)acetic acid
• 英文别名: (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl-methoxy)-acetic Acid；2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)acetic acid
• CAS: 540803-67-6
• 化学式: C₉H₁₀O₅S
• 分子量: 230.241
• InChiKey: WKUBGFWBSGWPEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy)acetic acid 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以40%的产率得到2-((5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy)acetic acid
  参考文献：
  名称：

  直接 C–H 芳基化聚合形成具有更高产率和分子量的阴离子水溶性聚（3,4-亚乙基二氧噻吩）

  摘要：

  一种简便且环境友好的 Pd 催化直接 C-H 芳基化聚合 (DAP) 已被开发用于合成阴离子基团官能化 3,4-亚乙基二氧噻吩的均聚物和共聚物，具有高产率（高达 99%）、高分子量和窄的多分散性。已经研究了各种 Pd 催化剂、膦配体和添加剂对聚合物性能的影响。该方法得到的阴离子聚（3,4-亚乙基二氧噻吩）的分子量比以前报道的化学或电化学方法产生的分子量更高。该方法还用于合成用羧酸基团官能化的聚合物，而无需保护/脱保护步骤。所得聚合物可由水或高极性有机溶剂加工而成。我们还展示了无磷化氢，水介导的 Pd 催化的 DAP。阴离子聚（3,4-亚乙基二氧噻吩）在水中稳定，有望用于传感器、药物输送和细胞工程。

  DOI：

  10.1055/s-0037-1611310
• 作为产物：
  描述：

  羟甲基 EDOT 在 sodium hydride 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy)acetic acid
  参考文献：
  名称：

  In vitro selection of electrochemical peptide probes using bioorthogonal tRNA for influenza virus detection

  摘要：

  一个含有3,4-乙烯二氧基噻吩共轭氨基苯丙氨酸的电聚合肽探针被开发用于检测流感病毒的“开启”检测。

  DOI：

  10.1039/c8cc01775a
• 作为试剂：
  描述：

  (2,3-Dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-acetic acid ethyl ester 、 乙醇 、 氢氧化钾 在 氯化钠 、 magnesium sulfate 、 raw product 、 ethyl acetate hexanes 、 2-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy)acetic acid 作用下， 以 水 为溶剂， 反应 0.5h， 以resulting in pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-acetic acid的产率得到2-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy)acetic acid
  参考文献：
  名称：

  3,4-alkylenedioxythiophene compounds and polymers thereof

  摘要：

  一种由式（I）表示的噻吩化合物： 其中A代表C1-5-烷基桥；R代表-R1-(C═O)-R2基团；-R1-代表-R3-或-R4-X-R5-基团；R2是氢、羟基、硫醇基、-NR6R7、-OR8或-SR9基团；R3、R4和R5分别是烷基或芳基；X是-O-、-S-或═NR10；R6和R7分别是氢、可选取代的氨基或可选取代的烷基；R8和R9分别是可选取代的烷基（可选地具有来自醇、酰胺、醚、酯或磺酸酯基团的至少一个取代基）、可选取代的芳基或-SiR11R12R13基团；R10是烷基、芳基或酰基；R11、R12和R13分别是可选取代的烷氧基或烷基；从中得到的聚合物；根据式（I）聚合噻吩的过程，可选择化学或电化学方法；以及含有从中得到的聚合物的溶液、分散液、糊状物和层。

  公开号：

  US06852830B2

文献信息

• Palladium-catalyzed direct C–H arylations of dioxythiophenes bearing reactive functional groups: a step-economical approach for functional π-conjugated oligoarenes
  作者：Ching-Yuan Liu、Hui Chong、Hsing-An Lin、Yoshiro Yamashita、Bin Zhang、Kuo-wei Huang、Daizuke Hashizume、Hsiao-hua Yu

  DOI：10.1039/c5ob00705d

  日期：——

  A phosphine-free C–H arylation of dioxythiophenes bearing unprotected functional groups affords oligoarenes with good yields.

  一种无磷C-H芳基化方法可用于含有未保护官能团的二氧基噻吩，产率较高地制备寡芳烃。
• Strategy to Immobilize Peptide Probe Selected through In Vitro Ribosome Display for Electrochemical Aptasensor Application
  作者：Mi Chin、Seiichi Tada、Min-Han Tsai、Yoshihiro Ito、Shyh-Chyang Luo

  DOI：10.1021/acs.analchem.0c01891

  日期：2020.8.18

  In this study, we demonstrated an electrochemical aptasensor for calmodulin (CaM) detection and the peptide sequence (YWDKIKDFIGG) is obtained from in vitro ribosome display selection. To immobilize this peptide probe on the electrode surface, cystine was incorporated at the end of this peptide sequence. After a maleimide-functionalized poly(3,4-ethylenedioxythiophene), poly(EODT-MI), film was electropolymerized on the electrode, the peptide probe was immobilized through thiol–ene conjugation with the cystine end. Four peptides with different linkers were used for the binding test of bovine serum albumin and CaM using a quartz crystal microbalance. The zwitterionic linker EKEKEKEKEKEK provided good antifouling properties and the highest CaM binding. Furthermore, the immobilization of the peptide with this zwitterionic linker resulted in a minimal increase in the electrochemical impedance. By immobilizing the peptide with the selected zwitterionic linker, we successfully demonstrated an electrochemical aptasensor with a linear detection range for CaM from 0.01 to 10 mg/L and a detection limit of 0.001 mg/L.

  在这项研究中，我们展示了一种用于检测钙调蛋白（CaM）的电化学适配传感器，肽序列（YWDKIKDFIGG）是通过体外核糖体展示筛选获得的。为了将肽探针固定在电极表面，在肽序列末端加入了胱氨酸。在电极上电聚合马来酰亚胺功能化聚（3,4-亚乙二氧基噻吩）聚（EODT-MI）薄膜后，肽探针通过与胱氨酸末端的硫醇-烯共轭而被固定。使用石英晶体微天平对四种不同连接体的肽进行了牛血清白蛋白和 CaM 的结合测试。其中，EKEKEKEKEK 的两性离子连接体具有良好的防污性能，与 CaM 的结合力最高。此外，用这种齐聚物连接体固定多肽后，电化学阻抗的增加极小。通过将肽与所选的齐聚物连接固定，我们成功地展示了一种电化学传感器，其对 CaM 的线性检测范围为 0.01 至 10 mg/L，检测限为 0.001 mg/L。
• Process for preparing an aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer
  申请人：Louwet Frank

  公开号：US20050245723A1

  公开（公告）日：2005-11-03

  A process for preparing an aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer, containing structural units according to formula (I): in which R 1 and R 2 independently of one another represent hydrogen or a C 1-5 -alkyl group or together form an optionally substituted C 1-5 -alkylene residue, comprising the step of: preparing the polythiophene or thiophene copolymer with an initiator in a reaction is medium in the presence of polyanions under oxidizing or reducing conditions under an inert atmosphere such that when said initiator is added less than 3 mg of oxygen per litre of the reaction medium is present in the reaction medium; an aqueous or non-aqueous solution or dispersion prepared therewith; the use of an aqueous or non-aqueous dispersion or solution comprising the aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer for coating an object; a printable paste containing the aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer; and an electroconductive or an antistatic layer prepared using an aqueous or non-aqueous solution or dispersion comprising the aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer.

  制备含有结构单元式(I)的聚噻吩或噻吩共聚物的水溶液或非水溶液或分散液的工艺，其中R1和R2独立地表示氢或C1-5烷基或一起形成一个可选择取代的C1-5烷基残基，包括以下步骤：在惰性气氛下，在存在聚阴离子的反应介质中使用引发剂制备聚噻吩或噻吩共聚物，在氧化或还原条件下，当添加少于每升反应介质中3毫克氧时，制备得到水溶液或非水溶液或分散液；使用含有聚噻吩或噻吩共聚物的水溶液或非水溶液或分散液的水溶液或非水溶液或分散液涂覆物体；包含聚噻吩或噻吩共聚物的水溶液或非水溶液或分散液的可印刷浆料；以含有聚噻吩或噻吩共聚物的水溶液或非水溶液或分散液制备的导电层或抗静电层。
• 3,4-Alkylenedioxythiophene compounds and polymers thereof
  申请人：AGFA-GEVAERT

  公开号：US20030176628A1

  公开（公告）日：2003-09-18

  A thiophene compound represented by formula (I): 1 in which A represents a C 1-5 -alkylene bridge; R represents a —R 1 —(C═O)—R 2 group; —R 1 — represents a —R 3 — or —R 4 —X—R 5 — group; R 2 is hydrogen, a hydroxy group, a thiol group, —NR 6 R 7 , —OR 8 or a —SR 9 group; R 3 , R 4 and R 5 are independently an alkylene group or an arylene group; X is a —O—, —S— or ═NR 10 ; R 6 and R 7 are independently hydrogen, an optionally substituted amino group or an optionally substituted alkyl group; R 8 and R 9 are independently an optionally substituted alkyl group (optionally with at least one substituent selected from the group consisting of an alcohol, amide, ether, ester or sulfonate group), an optionally substituted aryl group or a —SiR 11 R 12 R 13 group; R 10 is an alkyl, aryl or acyl group; and R 11 R 12 and R 13 are independently an optionally substituted alkoxy or alkyl group; polymers derived therefrom; a process for polymerizing a thiophene according to formula (I), optionally chemically or electrochemically; and solutions, dispersions, pastes and layers containing polymers derived therefrom.

  一种由公式（I）表示的噻吩化合物：其中A代表C1-5-烷基桥；R代表—R1—（C═O）—R2基团；—R1—代表—R3—或—R4—X—R5—基团；R2为氢、羟基、硫醇基、—NR6R7、—OR8或—SR9基团；R3、R4和R5分别为烷基基团或芳基基团；X为—O—、—S—或═NR10；R6和R7分别为氢、可选取代的氨基基团或可选取代的烷基基团；R8和R9分别为可选取代的烷基基团（可选含有醇、酰胺、醚、酯或磺酸盐基团中的至少一个取代基），可选取代的芳基基团或—SiR11R12R13基团；R10为烷基、芳基或酰基基团；R11、R12和R13分别为可选取代的烷氧基或烷基基团；由此导出的聚合物；根据公式（I）聚合噻吩的过程，可选择化学或电化学；以及含有由此导出的聚合物的溶液、分散体、糊状物和层。
• Process for preparing an aqueous or non-aqueous solution or dispersion of a polythionphene or thiophene copolymer
  申请人：Agfa-Gevaert

  公开号：US20030211331A1

  公开（公告）日：2003-11-13

  A process for preparing an aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer, containing structural units according to formula (I): 1 in which R 1 and R 2 independently of one another represent hydrogen or a C 1-5 -alkyl group or together form an optionally substituted C 1-5 -alkylene residue, comprising the step of: preparing the polythiophene or thiophene copolymer with an initiator in a reaction medium in the presence of polyanions under oxidizing or reducing conditions under an inert atmosphere such that when said initiator is added less than 3 mg of oxygen per litre of the reaction medium is present in the reaction medium; an aqueous or non-aqueous solution or dispersion prepared therewith; the use of an aqueous or non-aqueous dispersion or solution comprising the aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer for coating an object; a printable paste containing the aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer; and an electroconductive or an antistatic layer prepared using an aqueous or non-aqueous solution or dispersion comprising the aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer.

  一种制备含有式(I)中所述结构单元的聚噻吩或噻吩共聚物的水性或非水性溶液或分散液的方法，其中R1和R2独立地表示氢或C1-5烷基或共同形成一个可选的取代的C1-5烷基残基，包括以下步骤：在惰性气氛下，在存在聚阴离子的反应介质中使用引发剂制备聚噻吩或噻吩共聚物，在氧化或还原条件下，使得当添加少于每升反应介质中3毫克的氧气时，反应介质中存在氧气；由此制备的水性或非水性溶液或分散液；使用含有聚噻吩或噻吩共聚物的水性或非水性分散液或溶液涂覆物体；含有聚噻吩或噻吩共聚物的水性或非水性溶液或分散液的可印刷浆料；使用含有聚噻吩或噻吩共聚物的水性或非水性溶液或分散液制备的导电或抗静电层。