3-N-morpholinobenzo[b]thiophene 1-oxide | 852050-24-9

• 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: 3-N-morpholinobenzo[b]thiophene 1-oxide
• 英文别名: 3-morpholinobenzo[b]thiophene 1-oxide；3-N-morpholinobenzo[b]thiophene S-oxide；3-Morpholin-4-yl-1-benzothiophene 1-oxide
• CAS: 852050-24-9
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: SGIVHZHSNBRJMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-N-morpholinobenzo[b]thiophene 1-oxide 在 二环己烷并-18-冠醚-6 、 palladium diacetate 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.5h， 生成 2-(3-Morpholin-4-yl-benzo[b]thiophen-2-yl)-benzonitrile
  参考文献：
  名称：

  Efficient Access to 2-Aryl-3-Substituted Benzo[b]thiophenes

  摘要：

  Benzo[b]thiophene derivatives are important in part because of their use as selective estrogen receptor modulators. They are usually synthesized by intramolecular cyclization. Here, we propose a method for the synthesis of 2-arylbenzo[b]thiophenes with heteroatoms at the 3-positions directly from the benzo [b]thiophene core by using an aromatic nucleophilic substitution reaction and Heck-type coupling. This methodology provides 2-aryl-3-amino or phenoxybenzo[b]thiophenes in about 35% overall yield in 5 steps.

  DOI：

  10.1021/jo0500378
• 作为产物：
  描述：

  3-溴苯并噻吩 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 3-N-morpholinobenzo[b]thiophene 1-oxide
  参考文献：
  名称：

  苯并[b]萘并[1,2-d]噻吩亚砜：仿生合成、光物理性质和应用

  摘要：

  苯并噻吩的生物降解启发了非对称噻吩稠合芳烃体系的实用合成路线。一系列π-共轭苯并[ b ]萘并[1,2 - d ]噻吩(BNT)亚砜在溶液和固态下均具有优异的荧光特性。不同布朗斯台德酸的荧光变化说明了这些化合物的高应用潜力。

  DOI：

  10.1002/anie.202203908

文献信息

• Synthesis of C2 Substituted Benzothiophenes via an Interrupted Pummerer/[3,3]-Sigmatropic/1,2-Migration Cascade of Benzothiophene <i>S</i> -Oxides
  作者：Zhen He、Harry J. Shrives、José A. Fernández-Salas、Alberto Abengózar、Jessica Neufeld、Kevin Yang、Alexander P. Pulis、David J. Procter

  DOI：10.1002/anie.201801982

  日期：2018.5.14

  Functionalized benzothiophenes are important scaffolds found in molecules with wide ranging biological activity and in organic materials. We describe an efficient, metal‐free synthesis of C2 arylated, allylated, and propargylated benzothiophenes. The reaction utilizes synthetically unexplored yet readily accessible benzothiophene S‐oxides and phenols, allyl‐, or propargyl silanes in a unique cascade

  功能化的苯并噻吩是在具有广泛生物活性的分子和有机材料中发现的重要支架。我们描述了一种高效，无金属的C2芳基化，烯丙基化和炔丙基化苯并噻吩的合成方法。该反应以独特的级联顺序利用合成的未探索但易于获得的苯并噻吩S-氧化物和苯酚，烯丙基或炔丙基硅烷。苯并噻吩S-氧化物与偶合剂之间的Pummerer反应中断，生成的aromatic盐缺乏芳香性，因此容易实现[3,3]-σ重排。随后生成的苯并噻吩盐经历了以前未经探索的1,2-迁移，以进入C2功能化的苯并噻吩。
• Efficient Access to 2-Aryl-3-Substituted Benzo[<i>b</i>]thiophenes
  作者：Emilie David、Julie Perrin、Stéphane Pellet-Rostaing、Jérémie Fournier dit Chabert、Marc Lemaire

  DOI：10.1021/jo0500378

  日期：2005.4.1

  Benzo[b]thiophene derivatives are important in part because of their use as selective estrogen receptor modulators. They are usually synthesized by intramolecular cyclization. Here, we propose a method for the synthesis of 2-arylbenzo[b]thiophenes with heteroatoms at the 3-positions directly from the benzo [b]thiophene core by using an aromatic nucleophilic substitution reaction and Heck-type coupling. This methodology provides 2-aryl-3-amino or phenoxybenzo[b]thiophenes in about 35% overall yield in 5 steps.
• Benzo[ <i>b</i> ]naphtho[1,2‐ <i>d</i> ]thiophene Sulfoxides: Biomimetic Synthesis, Photophysical Properties, and Applications
  作者：Xian‐Yan Shen、Man Li、Tai‐Ping Zhou、Ji‐Rong Huang

  DOI：10.1002/anie.202203908

  日期：2022.8.26

  practical synthetic route to nonsymmetrical thiophene-fused aromatic systems was inspired by the biodegradation of benzothiophene. Excellent fluorescence characteristics of a series of π-conjugated benzo[b]naphtho[1,2-d]thiophene (BNT) sulfoxides were observed both in solution and in the solid state. Fluorescence variation with different Brønsted acids illustrates the high application potential of these

  苯并噻吩的生物降解启发了非对称噻吩稠合芳烃体系的实用合成路线。一系列π-共轭苯并[ b ]萘并[1,2 - d ]噻吩(BNT)亚砜在溶液和固态下均具有优异的荧光特性。不同布朗斯台德酸的荧光变化说明了这些化合物的高应用潜力。