dimethyl benzo[b]thiophene-2,3-dicarboxylate | 41892-84-6

• 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: dimethyl benzo[b]thiophene-2,3-dicarboxylate
• 英文别名: Dimethyl 1-benzothiophene-2,3-dicarboxylate
• CAS: 41892-84-6
• 化学式: C₁₂H₁₀O₄S
• mdl: MFCD00663602
• 分子量: 250.275
• InChiKey: HBPKHFSEFDBUQO-UHFFFAOYSA-N

物化性质

• 熔点：
  91 °C(Solv: ethanol (64-17-5))
• 沸点：
  213-215 °C(Press: 18 Torr)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl benzo[b]thiophene-2,3-dicarboxylate 在 乙酸酐 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 benzothiophene-2,3-dicarboxylic anhydride
  参考文献：
  名称：

  Air promoted annulation of thiophenols with alkynes leading to benzothiophenes

  摘要：

  空气促进了硫酚与炔烃的分子间环化反应，形成复杂的苯并噻吩化合物。

  DOI：

  10.1039/c8ob00010g
• 作为产物：
  描述：

  以 甲苯 为溶剂， 反应 16.0h， 以71%的产率得到dimethyl benzo[b]thiophene-2,3-dicarboxylate
  参考文献：
  名称：

  Palladated Oligophenylene Thioethers: Synthesis and Reactivity toward Isocyanides, Carbon Monoxide, and Alkynes

  摘要：

  Phenylene thioethers XC6H4(SC6H4R-4)-a (a = 2, 4; X = Br, I; R = H, OMe, NO2) react with Pd(dba)(2) and 2 equiv of PPh3 or 1 equiv of 2,2'-bipyridine (bpy) to afford trans-[PdBr{C6H4(SC6H4R-4)-a}(PPh3)(2)] (for example, a = 2, R = H (1)) or cis-[PdI{C6H4(SC6H4R-4}-a)(bpy)] (for example, a = 2, R = H (5)), respectively. Complex 1 (as well as some of its homologues) reacts (1) with 1 equiv of [PdCl2(NCPh)(2)] to give a mixture of isomers of [{PdBr(PPh3)}(2)(mu-C,S-C6H4SPh-2)(2)], (2) with 1 equiv of XyNC (Xy = C6H3Me2-2,6) to render SP-4-4-[PdBr{C,S-C(=NXy)C6H4-2-SPh}(PPh3)], (3) with XyNC and TlTfO (TfO = O3SCF3; 1:2:1 molar ratios) to give SP-4-3-[Pd{C,S-C(=NXy)C6H4-2-SPh}(CNXy)(PPh3)TfO, (4) with 4 equiv of XyNC to give SP-4-4-[Pd{C,N-C(=NXy)C(=NXy)C(=NXy)C6H4(SPh)-2}Br(CNXy)], or (5) with TlTfO (1:1 molar ratio) to afford a mixture of compounds from which a few single crystals of (Ph3PC6H4SPh-2)TfO could be obtained. Complexes with bpy ligands react with 2 equiv of PPh3 to give trans-[PdI{C6H4(SC6H4R-4)-4} (PPh3)(2)] or with 3 equiv of XyNC affording monoinserted complexes resulting from the replacement of the PdI(bpy) group by trans-{C(=NXy)}Pd(CNXy)(2). Dinuclear complexes are prepared by reacting diiodophenylene thioethers with Pd(dba)(2) and bpy. Complex 5 reacts with TlTfO and CO or various alkynes RC CR' to afford, respectively, [Pd{C,S-C(O)C6H4SPh-2)}bpy]TfO or [Pd{C,S-C(R')=C(R)C6H4SPh-2}bpy], the latter of which decompose thermally to give the benzothiophenes resulting from the C-S coupling. Crystal structures of some model complexes have been determined.

  DOI：

  10.1021/om200607h

文献信息

• METHOD FOR PROMOTING PLANT GROWTH
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150282482A1

  公开（公告）日：2015-10-08

  The present invention provides a method for promoting plant growth, which comprises treating a plant with a compound represented by the following Formula (1): provided that a method for promoting plant growth which comprises treating plants with a compound corresponding to any one of the following (1) to (8) is excluded: (1) Methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (2) Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (3) Methyl 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (4) Methyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (5) Ethyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (6) Ethyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (7) Ethyl 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, and (8) Ethyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate.

  本发明提供了一种促进植物生长的方法，包括用下式表示的化合物处理植物： 只要排除用与以下任一化合物相对应的化合物处理植物的促进植物生长方法：(1) 甲基4-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(2) 甲基5-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(3) 甲基6-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(4) 甲基7-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(5) 乙基4-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(6) 乙基5-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(7) 乙基6-(三氟甲基)苯并[b]噻吩-2-羧酸酯，以及(8) 乙基7-(三氟甲基)苯并[b]噻吩-2-羧酸酯。
• Facile Access to Benzothiophenes through Metal-Free Iodine-­Catalyzed Intermolecular Cyclization of Thiophenols and Alkynes
  作者：Daoshan Yang、Hua Wang、Kelu Yan、Mengqi Zhang、Wei Wei、Yao Liu、Laijin Tian

  DOI：10.1055/s-0034-1378841

  日期：——

  A novel iodine-catalyzed method for the synthesis of benzothiophene derivatives through cascade reactions of substituted thiophenols with alkynes has been demonstrated under metal- and solvent-free conditions. The present protocol uses inexpensive and environmentally friendly molecular iodine as the catalyst, and the corresponding products are obtained in moderate to excellent yields. Such an efficient

  在无金属和无溶剂条件下，证明了一种通过取代苯硫酚与炔烃的级联反应合成苯并噻吩衍生物的新型碘催化方法。本协议使用廉价且环保的分子碘作为催化剂, 并以中等至优良的收率获得相应的产品。这种高效、经济和绿色的转化应该为有机和药物化学中的各种苯并噻吩提供一种有吸引力的方法。
• Metal-free n-Et₄NBr-catalyzed radical cyclization of disulfides and alkynes leading to benzothiophenes under mild conditions
  作者：Daoshan Yang、Kelu Yan、Wei Wei、Laijin Tian、Qinghe Li、Jinmao You、Hua Wang

  DOI：10.1039/c4ra08260e

  日期：——

  A novel n-Et4NBr-catalyzed method for the synthesis of benzothiophene derivatives via cascade reactions of substituted disulfides with alkynes through S–S bond cleavage and alkenyl radical cyclization reactions has been developed. The reaction has a high functional-group tolerance. The new method is environmental and practical, and the starting materials are readily available. These advantages, relative

  已开发出一种新颖的n - Et 4 NBr催化方法，该方法通过取代的二硫化物与炔烃的S–S键断裂和烯基自由基环化反应的级联反应合成苯并噻吩衍生物。该反应具有较高的官能团耐受性。该新方法是环境实用的，并且起始材料容易获得。相对于先前的方法，这些优点为构建各种有用的苯并噻吩基序提供了机会。
• THIOL MEDIATED 5-(π-<i>ENDO)ORTHO</i> VINYL RADICAL CYCLIZATIONS
  作者：Pier Carlo Montevecchi、Maria Luisa Navacchia

  DOI：10.1080/10426500008076542

  日期：2000.1.1

  Abstract The radical reaction of benzenethiol with alkynes 1a-o carried out at 154 °C affords a mixture of thiol/alkyne adduct 3 and benzothiophene 5, deriving from vinyl radical intermediates 2 through hydrogen abstraction and 5-(π-endo)orthocyclization onto the adjacent thiophenyl ring, respectively. This latter reaction occurs through the reversible formation of cyclohexadienyl radical intermediates

  摘要 苯硫醇与炔烃 1a-o 的自由基反应在 154 °C 下进行，得到硫醇/炔烃加合物 3 和苯并噻吩 5 的混合物，通过夺氢和 5-（π-内）正环化衍生自乙烯基自由基中间体 2。相邻的苯硫环，分别。后一反应通过环己二烯基自由基中间体 4 的可逆形成而发生，其可以在很大程度上取决于所采用的反应条件而演变为 5。5-邻位环化受立体电子因素的控制，有利于 p 中心的线性 α-芳基乙烯基自由基 2a-f 的环化，以及极性因素，有利于 α-EWG 取代的乙烯基自由基 2c,n,o 的环化.
• 一种苯并噻吩类化合物的合成方法
  申请人：西北师范大学

  公开号：CN107226803A

  公开（公告）日：2017-10-03

  本发明提供了提供了一种苯并噻吩类化合物的合成方法，是在有机溶剂中，苯硫酚及衍生物和丁炔二羧酸二酯以1:1~1:3的摩尔比，在空气或氧气氛围下，20~90oC；反应时间为2~8h；减压蒸馏除去溶剂后进行柱层析分离，得到目标化合物。本发明反应试剂价格低廉，反应步骤简短，反应条件温和，收率高，纯度好，后处理简单，能有效降低工业生产成本，适合用于工业化生产。