8-hydroxy-4H-thieno[2,3-c]chromen-4-one | 1415703-39-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-hydroxy-4H-thieno[2,3-c]chromen-4-one
• 英文别名: 8-Hydroxythieno[2,3-c]chromen-4-one；8-hydroxythieno[2,3-c]chromen-4-one
• CAS: 1415703-39-7
• 化学式: C₁₁H₆O₃S
• 分子量: 218.233
• InChiKey: VGGOCUXKLHFCGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-溴噻酚-2-羧酸甲酯 在 potassium phosphate 、 四(三苯基膦)钯 、 三溴化硼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 22.25h， 生成 8-hydroxy-4H-thieno[2,3-c]chromen-4-one
  参考文献：
  名称：

  Design and synthesis of condensed thienocoumarins by Suzuki–Miyaura reaction/lactonization tandem protocol

  摘要：

  A concise and efficient approach to a series of chromen-4-ones with fused thiophene ring has been developed using the Suzuki-Miyaura reaction of bromothiophene-2- and 3-carboxylates with 2-methoxyboronic acids and subsequent cyclization of prepared alkyl (2-methoxy)aryl thiophene-2- and 3-carboxylates under the action of BBr3/KOtBu. Starting bromothiophenes are easily obtained from corresponding commercially available aminothiophenes by diazotization/bromination reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.096

文献信息

• Rh(<scp>iii</scp>)-catalyzed oxidative C–H bond arylation with hydroquinones: sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones
  作者：Wei Yang、Shan Wang、Qian Zhang、Qun Liu、Xianxiu Xu

  DOI：10.1039/c4cc08260e

  日期：——

  An efficient Rh(iii)-catalyzed C–H bond arylation with phenol derivatives was developed for the direct and sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones.

  开发了一种高效的Rh(iii)催化的C-H键芳基化反应，用于直接和可持续地合成二苯并[b,d]吡喃-6-酮和苯并[d]萘并[1,2-b]吡喃-6-酮。
• Rh(<scp>iii</scp>)-Catalyzed sequential <i>ortho</i>-C–H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[<i>b,d</i>]pyran-6-ones
  作者：Yaqun Dong、Jin-Tao Yu、Song Sun、Jiang Cheng

  DOI：10.1039/d0cc00176g

  日期：——

  d ortho-C–H functionalization of sulfoxonium ylides followed by intramolecular annulation reactions with quinones was described, where the carbonyl in sulfoxonium ylides served as a chelation group. This protocol leads to the efficient formation of 2-hydroxy-6H-benzo[c]chromen-6-one derivatives, proceeding with the cleavage of the C(O)–S bond in sulfoxonium ylides. This protocol featured high chemo-selectivity

  描述了铑（III）催化的亚砜基吡啶的邻位C-H官能化，然后与醌进行分子内环化反应，其中亚砜基吡啶中的羰基用作螯合基团。该方案导致2-羟基-6 H-苯并[ c ]铬n-6-one衍生物的有效形成，并进行了亚砜基磺酸盐中C（O）-S键的裂解。该协议具有高化学选择性和官能团耐受性的特点，其中亚硫酸sulf盐作为芳酰基源。
• Facile synthetic route to benzo[<i>c</i>]chromenones and thieno[2,3-<i>c</i>]chromenones
  作者：Olga Ya. Shyyka、Roman L. Martyak、Mykola A. Tupychak、Nazariy T. Pokhodylo、Mykola D. Obushak

  DOI：10.1080/00397911.2017.1380833

  日期：2017.12.17

  two-step procedure for the synthesis of fused chromenone derivatives was developed. Reduction of the obtained in the Meerwein arylation reaction aryl- and thienylquinones allowed to construct 6H-benzo[c]chromene-6-ones and 4H-thieno[2,3-c]chromen-4-one in a more cost- and time-effective manner in comparison with already known methods. The obtained products have provided a new entry to chromenone derivatives

  摘要 开发了合成稠合色酮衍生物的方便的两步法。减少在 Meerwein 芳基化反应中获得的芳基-和噻吩基醌允许以更多的成本和时间构建 6H-benzo[c]chromene-6-ones 和 4H-thieno[2,3-c]chromen-4-one - 与已知方法相比的有效方式。获得的产品为色酮衍生物提供了一个新的入口。图形概要
• Design and synthesis of condensed thienocoumarins by Suzuki–Miyaura reaction/lactonization tandem protocol
  作者：Viktor O. Iaroshenko、Sajid Ali、Satenik Mkrtchyan、Ashot Gevorgyan、Tariq Mahmood Babar、Volodymyr Semeniuchenko、Zahid Hassan、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tetlet.2012.10.096

  日期：2012.12

  A concise and efficient approach to a series of chromen-4-ones with fused thiophene ring has been developed using the Suzuki-Miyaura reaction of bromothiophene-2- and 3-carboxylates with 2-methoxyboronic acids and subsequent cyclization of prepared alkyl (2-methoxy)aryl thiophene-2- and 3-carboxylates under the action of BBr3/KOtBu. Starting bromothiophenes are easily obtained from corresponding commercially available aminothiophenes by diazotization/bromination reaction. (C) 2012 Elsevier Ltd. All rights reserved.