phenyl thiophene-2-sulfonate | 1179383-43-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: phenyl thiophene-2-sulfonate
• 英文别名: Phenyl thienylsulfonate
• CAS: 1179383-43-7
• 化学式: C₁₀H₈O₃S₂
• mdl: MFCD01159723
• 分子量: 240.304
• InChiKey: RKCWASHNARHRPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  387.3±24.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenyl thiophene-2-sulfonate 、 3'-溴苯乙酮 在 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以75%的产率得到5-(3-acetylphenyl)thiophene-2-sulfonic acid phenyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Direct Arylation of Thiophenes Bearing SO₂R Substituents

  摘要：

  The palladium-catalyzed direct arylation of SO2R-substituted thiophene derivatives was found to proceed regioselectively at CS and in high yields using a variety of aryl bromides and as low as 0.5-0.1 mol % of phosphine-free Pd(OAc)(2) as the catalyst. For these reactions, sulfonyls, sulfonamides, or even a sulfonic ester as the thiophene substituents were successfully employed.

  DOI：

  10.1021/jo200918n
• 作为产物：
  描述：

  sodium thiophene-2-sulfinate 、 苯酚 以 水 、 乙腈 为溶剂， 反应 2.0h， 以53%的产率得到phenyl thiophene-2-sulfonate
  参考文献：
  名称：

  苯酚与芳烃亚磺酸钠的实用电氧化磺酰化生成芳基磺酸酯

  摘要：

  已经通过电氧化开发了一种实用且可持续的芳基磺酸酯合成方法。该反应使用稳定且容易获得的苯酚和芳基亚磺酸钠作为起始材料，在温和的反应条件下进行，无需额外的氧化剂。包括那些带有官能团的芳基磺酸酯以良好至极好的产率生产。该反应也可以在不降低反应效率的情况下以克级进行。这些结果很好地证明了该反应在有机合成中的潜在合成价值。

  DOI：

  10.1021/acs.joc.1c00260

文献信息

• Sulfonate Versus Sulfonate: Nickel and Palladium Multimetallic Cross-Electrophile Coupling of Aryl Triflates with Aryl Tosylates
  作者：Kai Kang、Liangbin Huang、Daniel J. Weix

  DOI：10.1021/jacs.0c04670

  日期：2020.6.17

  While phenols are frequent and convenient aryl sources in cross-coupling, typically as sulfonate esters, the direct cross-Ullmann coupling of two different sulfonate esters is unknown. We report here a general solution to this chal-lenge catalyzed by a combination of Ni and Pd with Zn reductant and LiBr as an additive. The reaction has broad scope, as demonstrated in 33 examples (65% ± 11% ave yield)

  虽然苯酚是交叉偶联中常见且方便的芳基来源，通常作为磺酸酯，但两种不同磺酸酯的直接交叉乌尔曼偶联尚不清楚。我们在此报告了针对这一挑战的通用解决方案，该解决方案由 Ni 和 Pd 与 Zn 还原剂和 LiBr 作为添加剂的组合催化。该反应具有广泛的范围，如 33 个实例所示（平均产率 65% ± 11%）。机理研究表明，Pd 强烈偏好三氟甲磺酸芳基酯，Ni 催化剂对甲苯磺酸芳基酯的偏好较小，催化剂之间的芳基转移由 Zn 介导，Pd 通过消耗芳基锌中间体来提高产率。
• SuFEx Reactions of Sulfonyl Fluorides, Fluorosulfates, and Sulfamoyl Fluorides Catalyzed by N-Heterocyclic Carbenes
  作者：Muze Lin、Jinyun Luo、Yu Xie、Guangfen Du、Zhihua Cai、Bin Dai、Lin He

  DOI：10.1021/acscatal.3c03820

  日期：2023.11.17

  Sulfur(VI) fluoride exchange (SuFEx) click chemistry provides a powerful tool for the rapid assembly of modular connections. Herein, we report an organocatalytic SuFEx reaction of sulfonyl fluorides, fluorosulfates, and sulfamoyl fluorides. Under the catalysis of 10 mol % N-heterocyclic carbene (NHC), or under the relay catalysis of NHC and HOBt, different SuFExable hubs efficiently undergo click reactions

  硫 (VI) 氟化物交换 (SuFEx) 点击化学为快速组装模块化连接提供了强大的工具。在此，我们报道了磺酰氟、氟硫酸盐和氨磺酰氟的有机催化 SuFEx 反应。在10 mol% N-杂环卡宾（NHC）的催化下，或在NHC和HOBt的中继催化下，不同的SuFExable中心可以有效地与醇或胺发生点击反应，生成磺酸盐、磺酰胺、硫酸盐、氨基磺酸盐和磺酰胺49 –99% 的收益率。通过该方法已制备了190多种磺酰化产物，其中包括25种天然产物衍生物。机理研究表明，NHCs 可能充当以碳为中心的布朗斯台德碱，通过形成氢键来活化醇或胺。
• METHOD FOR PATTERN FORMATION, METHOD AND COMPOSITION FOR RESIST UNDERLAYER FILM FORMATION, AND RESIST UNDERLAYER FILM
  申请人：MINEGISHI Shin-ya

  公开号：US20120129353A1

  公开（公告）日：2012-05-24

  Provided by the present invention is a method including: (1) forming a resist underlayer film on the upper face side of a substrate to be processed using a composition for forming a resist underlayer film, the composition containing (A) a compound having a group represented by the following formula (1); (2) forming a resist coating film by applying a resist composition on the resist underlayer film; (3) exposing the resist coating film by selectively irradiating the resist coating film with a radiation; (4) forming a resist pattern by developing the exposed resist coating film; and (5) forming a predetermined pattern on the substrate to be processed by sequentially dry etching the resist underlayer film and the substrate using the resist pattern as a mask.
• COMPOSITION FOR FORMING RESIST UNDERLAYER FILM
  申请人：JSR CORPORATION

  公开号：US20150197664A1

  公开（公告）日：2015-07-16

  A composition for forming a resist underlayer film includes (A) a compound. The compound (A) includes a group represented by formula (1). R represents a monovalent organic group having 1 to 30 carbon atoms. The monovalent organic group represented by R does not include an oxygen atom at an end of the side adjacent the sulfur atom. * represents a bonding hand. The compound (A) preferably includes a ring which is an aromatic ring, a heteroaromatic ring, or a combination thereof. The bonding hand denoted by * in the group represented by the formula (1) is preferably linked directly or via an oxygen atom to the ring.
• US9040232B2
  申请人：——

  公开号：US9040232B2

  公开（公告）日：2015-05-26