3-(4-fluorophenyl)-3-(4-methoxyphenyl)propionic acid | 80272-12-4

• 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: 3-(4-fluorophenyl)-3-(4-methoxyphenyl)propionic acid
• 英文别名: 3-(4-fluorophenyl)-3-(4-methoxyphenyl)propanoic Acid
• CAS: 80272-12-4
• 化学式: C₁₆H₁₅FO₃
• 分子量: 274.292
• InChiKey: UCLJFGSDWVZMEH-UHFFFAOYSA-N

物化性质

• 沸点：
  402.6±40.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-3-(4-methoxyphenyl)propionic acid 在 PPA 、 Polyphosphoric acid (PPA) 作用下， 反应 2.0h， 以13%的产率得到3-(4-Fluorophenyl)-6-methoxy-2,3-dihydroinden-1-one
  参考文献：
  名称：

  Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans

  摘要：

  A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineethanol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2nM for inhibition of dopamine uptake.

  DOI：

  10.1021/jm00361a002
• 作为产物：
  描述：

  ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate 在 硫酸 、 magnesium 、 溶剂黄146 作用下， 反应 24.5h， 生成 3-(4-fluorophenyl)-3-(4-methoxyphenyl)propionic acid
  参考文献：
  名称：

  Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans

  摘要：

  A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineethanol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2nM for inhibition of dopamine uptake.

  DOI：

  10.1021/jm00361a002

文献信息

• Photoredox Activation of Formate Salts: Hydrocarboxylation of Alkenes via Carboxyl Group Transfer
  作者：Yan Huang、Jing Hou、Le-Wu Zhan、Qian Zhang、Wan-Ying Tang、Bin-Dong Li

  DOI：10.1021/acscatal.1c04684

  日期：2021.12.17

  reagent, a wide range of alkenes can be converted into acid products via a carboxyl group transfer strategy in an additive-free fashion. Mechanistic studies revealed that radical anion species (CO2•– and carbon radical anions derived from the reduction of alkenes) are key intermediates of the transformation. This method has the advantages of high catalytic efficiency and a simple catalytic system, which

  开发了用于羧化的甲酸盐的光氧化还原活化模式。使用甲酸盐作为还原剂、羰基源和氢原子转移试剂，可以通过羧基转移策略以无添加剂的方式将各种烯烃转化为酸性产物。机理研究表明自由基阴离子物质（CO 2 •–和来自烯烃还原的碳自由基阴离子）是转化的关键中间体。该方法具有催化效率高、催化体系简单等优点，有望成为一种有前景的工业应用策略。
• Synthesis and Antibacterial Activity of 1-Aryl-3-(4-methoxyphenyl)-3-(4-fluorophenyl)propanamides and Propanoates
  作者：A. U. Isakhanyan、N. Z. Akopyan、Z. A. Ovasyan、N. S. Arutyunyan、H. M. Stepanyan、J. A. Avakimyan、G. A. Panosyan

  DOI：10.1134/s1070363222060020

  日期：2022.6

  Abstract N-Acylation of some primary alkyl-, aryl-, and heterocyclic amines with 3-(4-methoxyphenyl)-3-(4-fluorophenyl)propanoic acid chloride gave propanamide derivatives. The reaction of the above acid chloride with N,N-dimethylpropane-1,3-diamine and the subsequent action of an ethereal solution of methyl iodide affords 3-[3-(4-methoxyphenyl)-3-(4-fluorophenyl)propanoyl]amino}-N,N,N-trimethylpropane-1-aminium

  摘要 用 3-(4-甲氧基苯基)-3-(4-氟苯基)丙酰氯对一些伯烷基-、芳基-和杂环胺进行N-酰化，得到丙酰胺衍生物。上述酰氯与N , N-二甲基丙烷-1,3-二胺反应，随后与碘甲烷的醚溶液反应，得到 3-[3-(4-甲氧基苯基)-3-(4-氟苯基)丙酰基]氨基} -N，N，N-三甲基丙烷-1-碘化胺。○-酰化化合物-(1,3-苯并噻唑-2-基)甲基和 2-二甲基氨基烷基 3-(4-甲氧基苯基)-3-(4-氟苯基)丙酸酯-通过将相应化合物与 3- (4-甲氧基苯基)-3-(4-氟苯基)丙酸酐。它们随后用甲基碘的醚溶液处理产生相应的N , N , N -三甲基烷烃-1-碘化胺。研究了合成化合物的抗菌活性。
• 一种光催化烯烃类化合物与二氧化碳发生反马氏氢羧化反应的方法
  申请人：中国科学院理化技术研究所

  公开号：CN115197036A

  公开（公告）日：2022-10-18

  本发明公开一种光催化烯烃类化合物与二氧化碳发生反马氏氢羧化反应的方法，包括以下步骤：1)将光催化剂和电子牺牲体加入至溶剂中，得溶液A；2)将烯烃类化合物加入至溶液A中，得溶液B；3)在二氧化碳气氛中，用光源照射溶液B，烯烃类化合物与二氧化碳发生反马氏氢羧化反应。本发明首次通过光驱动的量子点催化实现了烯烃类化合物与二氧化碳的反马氏选择性的氢羧化反应。且该方法过程简单、条件温和、不需要高温高压、反应物范围广、光催化剂可循环利用，可以在克级规模反应制备反马氏氢羧化产物。
• BOGESO, K. P., J. MED. CHEM., 1983, 26, N 7, 935-947
  作者：BOGESO, K. P.

  DOI：——

  日期：——
• Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans
  作者：Klaus P. Boegesoe

  DOI：10.1021/jm00361a002

  日期：1983.7

  A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineethanol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2nM for inhibition of dopamine uptake.