methyl dibenzo[b,d]thiophene-3-carboxylate | 60718-96-9

• 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: methyl dibenzo[b,d]thiophene-3-carboxylate
• 英文别名: 3-(methoxycarbonyl)dibenzothiophene；Methyl-dibenzothiophen-3-carboxylat；dibenzothiophene-3-carboxylic acid methyl ester；Dibenzothiophen-3-carbonsaeure-methylester；methyl dibenzothiophene-3-carboxylate
• CAS: 60718-96-9
• 化学式: C₁₄H₁₀O₂S
• 分子量: 242.298
• InChiKey: LZFLTBYQDMBDRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2'-Methylsulfanyl-biphenyl-4-carboxylic acid methyl ester 在 硫酸 、 双氧水 、 vanadia 作用下， 以 水 、 乙腈 为溶剂， 生成 methyl dibenzo[b,d]thiophene-3-carboxylate
  参考文献：
  名称：

  Efficient Synthesis of Unsymmetrical Dibenzothiophenes by Acid-Mediated Intramolecular Cyclization of Biaryl Methyl Sulfoxides

  摘要：

  A convenient and high-yielding synthesis of unsymmetrical dibenzothiophenes has been achieved by an acid-mediated ring closure of the biphenyl ring having a sulfoxide substituent at the ortho position. Various functional groups are well tolerated in this methodology.

  DOI：

  10.1080/00397911.2010.525777

文献信息

• <i>N-</i> Benzyldithiocarbamate Salts as Sulfur Sources to Access Tricyclic Thioheterocycles Mediated by Copper Species
  作者：Bingling Luo、Qingbin Cui、Hongwen Luo、Yumin Hu、Peng Huang、Shijun Wen

  DOI：10.1002/adsc.201600405

  日期：2016.9.1

  Using an easily prepared triethylammonium N‐benzyldithiocarbamate salt as a sulfur source, a dual C−S functionalization of cyclic diaryliodoniums to form tricyclic thioheterocycles is realized. Our method uses the readily available copper sulfate to accelerate the chemical transformation under mild conditions. A broad range of cyclic diaryliodoniums with a ring size from 5‐ to 7‐membered can be employed

  使用易于制备的三乙基铵N-苄基二硫代氨基甲酸盐作为硫源，可以实现环状二芳基碘鎓的双重CS功能化，形成三环硫杂环。我们的方法使用容易获得的硫酸铜在温和条件下加速化学转化。可以使用范围从5到7元环的各种环状二芳环鎓来快速接触三环硫杂环化合物，包括二苯并噻吩，噻吨酮和苯并氧杂蒽。
• Palladium(<scp>ii</scp>)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of carbon–sulfur and carbon–hydrogen bonds
  作者：Mamoru Tobisu、Yoshihiro Masuya、Katsuaki Baba、Naoto Chatani

  DOI：10.1039/c5sc04890g

  日期：——

  A new process has been developed for the palladium(II)-catalyzed synthesis of dibenzothiophene derivatives via the cleavage of C–H and C–S bonds. In contrast to the existing methods for the synthesis of this scaffold by C–H functionalization, this new catalytic C–H/C–S coupling method does not require the presence of an external stoichiometric oxidant or reactive functionalities such as C–X or S–H

  开发了一种通过C-H 和 C-S 键裂解钯 ( II ) 催化合成二苯并噻吩衍生物的新工艺。与现有的通过 C-H 官能化合成该支架的方法相比，这种新的催化 C-H/C-S 偶联方法不需要存在外部化学计量氧化剂或反应性官能团，例如 C-X 或 S -H，允许其应用于复杂的 π 系统的合成。值得注意的是，该反应的产物形成步骤在于氧化加成步骤而不是还原消除步骤，使得该反应在机理上不常见。
• Palladium(II)-Catalyzed Synthesis of Dibenzothiophenes from 2-Biphenylyl Disulfides by C−H Functionalization
  作者：Kota Nishino、Yohei Ogiwara、Norio Sakai

  DOI：10.1002/chem.201802475

  日期：2018.8.1

  The palladium‐catalyzed oxidative preparation of dibenzothiophene derivatives from 2‐biphenylyl disulfides by C−H functionalization is described herein. This procedure shows a high tolerance toward various functional groups and does not require the further addition of a metal oxidant, a base, or a ligand. Also, the present method was applied to the facile preparation of dibenzoselenophene.

  本文描述了通过CH官能化反应由2-联苯基二硫化物进行钯催化的氧化制备二苯并噻吩衍生物。该方法显示出对各种官能团的高耐受性，并且不需要进一步添加金属氧化剂，碱或配体。同样，本方法也适用于二苯并硒基苯的简便制备。
• Pairing Iron and Nickel Catalysis for Electrochemical Esterification of Aryl Halides with Carbazates
  作者：Peng Xue、Liubo Li、Niankai Fu

  DOI：10.1021/acs.orglett.2c03034

  日期：2022.10.21

  for esterification of aryl halides by pairing iron and nickel electrocatalysis. The reaction involves anodically iron-catalyzed oxidation of carbazates to produce alkoxycarbonyl radicals. The carbon-centered radicals then enter nickel catalysis that is powered by cathodic reduction to deliver the radical coupling products. Mechanistic data are consistent with arylnickel(II) species as the key intermediates

  我们报告了一种通过配对铁和镍电催化来酯化芳基卤化物的电催化方法。该反应涉及阳极铁催化的氨基甲酸酯氧化以产生烷氧羰基自由基。然后，以碳为中心的自由基进入由阴极还原驱动的镍催化，以提供自由基偶联产物。机械数据与芳基镍 (II) 物种一致，它们是能够形成所需碳-碳键的关键中间体。
• RELATIVE REACTIVITIES OF ORGANOMETALLIC COMPOUNDS. XVIII. SELECTIVE METALATIONS OF DIBENZOTHIOPHENE
  作者：HENRY GILMAN、A. L. JACOBY、H. A. PACEVITZ

  DOI：10.1021/jo01219a004

  日期：1938.5