methyl 4''-bromo-[1,1':4',1''-terphenyl]-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4''-bromo-[1,1':4',1''-terphenyl]-2-carboxylate
• 英文别名: Methyl 2-[4-(4-bromophenyl)phenyl]benzoate
• 化学式: C₂₀H₁₅BrO₂
• 分子量: 367.242
• InChiKey: PYFSWHDVAVZUTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4''-bromo-[1,1':4',1''-terphenyl]-2-carboxylate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以97%的产率得到4''-bromo-[1,1':4',1''-terphenyl]-2-carboxylic acid
  参考文献：
  名称：

  维生素催化：通过（-）-核黄素介导的电子转移直接，光催化合成苯并香豆素

  摘要：

  公开了一种操作简单的方案，以促进直接从联芳基羧酸进入苯并-3,4-香豆素，而无需底物预官能化。作为经典内酯化策略的补充，这种分离依赖于光活化的（-）-核黄素（维生素B 2）的氧化能力，可通过光诱导的单电子转移生成杂环核。总的来说，催化剂的廉价性质，易于实施以及不存在外部金属添加剂，都令人信服地赞同将简单的维生素掺入现代催化剂中。

  DOI：

  10.1021/acs.orglett.8b00052
• 作为产物：
  描述：

  2-碘苯甲酸甲酯 、 4'-溴-4-联苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl 4''-bromo-[1,1':4',1''-terphenyl]-2-carboxylate
  参考文献：
  名称：

  2-Carbomethoxy-3-aryl-8-bicyclo[3.2.1]octanes:  Potent Non-Nitrogen Inhibitors of Monoamine Transporters

  摘要：

  Cocaine is a potent central nervous system stimulant with severe addiction liability. Its reinforcing and stimulant properties derive from inhibition of monoamine transport systems, in particular the dopamine transporter (DAT). This inhibition results in an increase in synaptic dopamine with subsequent stimulation of postsynaptic dopamine receptors. A wide variety of ligands manifest potent inhibition of the DAT, and these ligands include 3-aryltropane as well as 8-oxa-3-aryltropane analogues of cocaine. There has been considerable effort to determine structure-activity relationships of cocaine and congeners, and it is becoming clear that these inhibitors do not all interact with the DAT in the same manner. The functional role of the 8-heteroatom is the focus of this study. We describe the preparation and biology of a series of 2-carbomethoxy-3-arylbicyclo[3.2.1]octane analogues. Results show that methylene substitution of the amine or ether function of the 8-hetero-2-carbomethoxy-3-arylbicyclo[3.2.1]octanes yields potent inhibitors of monoamine transport. Therefore neither nitrogen nor oxygen are prerequisites for binding of tropane-like ligands to monoamine transporters.

  DOI：

  10.1021/jm000191g

文献信息

• Vitamin Catalysis: Direct, Photocatalytic Synthesis of Benzocoumarins via (−)-Riboflavin-Mediated Electron Transfer
  作者：Tobias Morack、Jan B. Metternich、Ryan Gilmour

  DOI：10.1021/acs.orglett.8b00052

  日期：2018.3.2

  photoactivated (−)-riboflavin (vitamin B2) to generate the heterocyclic core via photoinduced single electron transfer. Collectively, the inexpensive nature of the catalyst, ease of execution, and absence of external metal additives are a convincing endorsement for the incorporation of simple vitamins in contemporary catalysis.

  公开了一种操作简单的方案，以促进直接从联芳基羧酸进入苯并-3,4-香豆素，而无需底物预官能化。作为经典内酯化策略的补充，这种分离依赖于光活化的（-）-核黄素（维生素B 2）的氧化能力，可通过光诱导的单电子转移生成杂环核。总的来说，催化剂的廉价性质，易于实施以及不存在外部金属添加剂，都令人信服地赞同将简单的维生素掺入现代催化剂中。
• 2-Carbomethoxy-3-aryl-8-bicyclo[3.2.1]octanes:  Potent Non-Nitrogen Inhibitors of Monoamine Transporters
  作者：Peter C. Meltzer、Paul Blundell、Yaw F. Yong、Zhengming Chen、Clifford George、Mario D. Gonzalez、Bertha K. Madras

  DOI：10.1021/jm000191g

  日期：2000.8.1

  Cocaine is a potent central nervous system stimulant with severe addiction liability. Its reinforcing and stimulant properties derive from inhibition of monoamine transport systems, in particular the dopamine transporter (DAT). This inhibition results in an increase in synaptic dopamine with subsequent stimulation of postsynaptic dopamine receptors. A wide variety of ligands manifest potent inhibition of the DAT, and these ligands include 3-aryltropane as well as 8-oxa-3-aryltropane analogues of cocaine. There has been considerable effort to determine structure-activity relationships of cocaine and congeners, and it is becoming clear that these inhibitors do not all interact with the DAT in the same manner. The functional role of the 8-heteroatom is the focus of this study. We describe the preparation and biology of a series of 2-carbomethoxy-3-arylbicyclo[3.2.1]octane analogues. Results show that methylene substitution of the amine or ether function of the 8-hetero-2-carbomethoxy-3-arylbicyclo[3.2.1]octanes yields potent inhibitors of monoamine transport. Therefore neither nitrogen nor oxygen are prerequisites for binding of tropane-like ligands to monoamine transporters.