tert-butyl 3-bromothiophene-2-carboxylate | 62224-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: tert-butyl 3-bromothiophene-2-carboxylate
• CAS: 62224-15-1
• 化学式: C₉H₁₁BrO₂S
• 分子量: 263.155
• InChiKey: XCRPPRHDXKKLEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-bromothiophene-2-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.08h， 生成 tert-butyl 3-ethynylthiophene-2-carboxylate
  参考文献：
  名称：

  从乙酰胺快速合成3-氨基异香豆素衍生物

  摘要：

  报道了新颖且有效的快速合成3-氨基异香豆素的高产率至优异产率。这些有趣的支架既可以一步一步从现成的酰胺中获得，也可以通过两步序列从C–N交叉偶联后从相应的炔基溴中获得。该方案仅需要布朗斯台德酸或路易斯酸作为促进剂，为在平滑快速的条件下合成3-取代的香豆素提供了另一种方法。

  DOI：

  10.1039/c8ob02305k
• 作为产物：
  描述：

  3-溴噻吩-2-甲酸 在 硫酸 、 magnesium sulfate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 12.0h， 以39%的产率得到tert-butyl 3-bromothiophene-2-carboxylate
  参考文献：
  名称：

  五元杂芳基溴化物的钯催化氟化深度评估

  摘要：

  A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.

  DOI：

  10.1021/acs.organomet.5b00631

文献信息

• Synthesis of Thioxanthone 10,10-Dioxides and Sulfone-Fluoresceins via Pd-Catalyzed Sulfonylative Homocoupling
  作者：Gergely Knorr、Mariano L. Bossi、Alexey N. Butkevich、Stefan W. Hell

  DOI：10.1021/acs.orglett.3c04300

  日期：2024.2.2

  Our report describes the facile and scalable preparation of 9H-thioxanthen-9-one 10,10-dioxides via Pd-catalyzed sulfonylative homocoupling of the appropriately substituted benzophenones. This transformation provides a straightforward route to previously unreported sulfone-fluoresceins and -fluorones. Several examples of these red fluorescent dyes have been prepared, characterized, and evaluated as

  我们的报告描述了通过适当取代的二苯甲酮的 Pd 催化磺酰化自偶联来轻松且可规模化地制备 9 H-噻吨-9-酮 10,10-二氧化物。这种转化为以前未报道的砜荧光素和荧光酮提供了一条直接的途径。这些红色荧光染料的几个例子已经被制备、表征和评估为与具有 775 nm 受激发射损耗的超分辨率荧光显微镜兼容的活细胞渗透标记。
• PREVENTION OF LOSS AND RESTORATION OF BONE MASS BY CERTAIN PROSTAGLANDIN AGONISTS
  申请人：PFIZER INC.

  公开号：EP0946501B1

  公开（公告）日：2006-05-31
• NOVEL LXR MODULATORS WITH BICYCLIC CORE MOIETY
  申请人：Phenex-FXR GmbH

  公开号：US20210147398A1

  公开（公告）日：2021-05-20

  The present invention relates to bicyclic compounds (e.g. indoles) containing a sulfonyl moiety, which bind to the liver X receptor (LXRα and/or LXKβ) and act preferably as inverse agonists of LXR.
• In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides
  作者：Phillip J. Milner、Yang Yang、Stephen L. Buchwald

  DOI：10.1021/acs.organomet.5b00631

  日期：2015.10.12

  A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.
• Rapid synthesis of 3-amino isocoumarin derivatives from ynamides
  作者：Loïc Habert、Pascal Retailleau、Isabelle Gillaizeau

  DOI：10.1039/c8ob02305k

  日期：——

  A novel and efficient fast synthesis of 3-amino isocoumarins in good to excellent yields is reported. These interesting scaffolds can be obtained either in a single step from readily available ynamides or in a two-step sequence from the corresponding alkynyl bromide after C–N cross-coupling. This protocol, which only requires a Brønsted or Lewis acid as a promoter, offers an alternative approach toward

  报道了新颖且有效的快速合成3-氨基异香豆素的高产率至优异产率。这些有趣的支架既可以一步一步从现成的酰胺中获得，也可以通过两步序列从C–N交叉偶联后从相应的炔基溴中获得。该方案仅需要布朗斯台德酸或路易斯酸作为促进剂，为在平滑快速的条件下合成3-取代的香豆素提供了另一种方法。