2-[(4-biphenyl)methylene]-3-oxobutanoic acid ethyl ester | 910097-43-7

• 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: 2-[(4-biphenyl)methylene]-3-oxobutanoic acid ethyl ester
• 英文别名: Ethyl 3-oxo-2-[(4-phenylphenyl)methylidene]butanoate
• CAS: 910097-43-7
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: IRVBKDPZPMVYTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4-biphenyl)methylene]-3-oxobutanoic acid ethyl ester 在 吡啶 、 盐酸羟胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 (2Z,3E)-ethyl 2-(biphenyl-4-ylmethylene)-3-(4-(trifluoromethyl)benzoyloxyimino)butanoate
  参考文献：
  名称：

  酰基肟的可见光促进亚甲基基自由基形成：吡啶，喹啉和菲啶的统一方法

  摘要：

  已经建立了涉及可见光诱导的亚胺基自由基形成的统一策略，用于从酰基肟中构建吡啶，喹啉和菲啶。用FAC - [的Ir（ppy）3 ]作为催化剂photoredox，酰基肟通过1e中转化-还原成亚氨基自由基中间体，然后行分子内均裂芳族取代（HAS），得到含有N-芳烃其中。这些反应在室温下以宽范围的底物以高收率进行。这种可见光诱导的亚胺基自由基形成策略已成功地应用于五步精简合成苯并[ c ]菲啶生物碱。

  DOI：

  10.1002/anie.201411342
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 对苯基苯甲醛 生成 2-[(4-biphenyl)methylene]-3-oxobutanoic acid ethyl ester
  参考文献：
  名称：

  酰基肟的可见光促进亚甲基基自由基形成：吡啶，喹啉和菲啶的统一方法

  摘要：

  已经建立了涉及可见光诱导的亚胺基自由基形成的统一策略，用于从酰基肟中构建吡啶，喹啉和菲啶。用FAC - [的Ir（ppy）3 ]作为催化剂photoredox，酰基肟通过1e中转化-还原成亚氨基自由基中间体，然后行分子内均裂芳族取代（HAS），得到含有N-芳烃其中。这些反应在室温下以宽范围的底物以高收率进行。这种可见光诱导的亚胺基自由基形成策略已成功地应用于五步精简合成苯并[ c ]菲啶生物碱。

  DOI：

  10.1002/anie.201411342

文献信息

• Tacripyrines, the First Tacrine−Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer’s Disease
  作者：José Marco-Contelles、Rafael León、Cristóbal de los Ríos、Abdelouahid Samadi、Manuela Bartolini、Vincenza Andrisano、Oscar Huertas、Xavier Barril、F. Javier Luque、María I. Rodríguez-Franco、Beatriz López、Manuela G. López、Antonio G. García、María do Carmo Carreiras、Mercedes Villarroya

  DOI：10.1021/jm801292b

  日期：2009.5.14

  Tacripyrines (1-14) have been designed by combining an ACNE inhibitor (tacrine) with a calcium antagonist such as nimodipine and are targeted to develop a multitarget therapeutic strategy to confront AD. Tacripyrines are selective and potent ACNE inhibitors in the nanomolar range. The mixed type inhibition of hAChE activity of compound 11 (IC50 105 +/- 15 nM) is associated to a 30.7 +/- 8.6% inhibition of the proaggregating action of ACNE on the A beta and a moderate inhibition of A beta self-aggregation (34.9 +/- 5.4%). Molecular modeling indicates that binding of compound 11 to the ACNE PAS mainly involves the (R)-11 enantiomer, which also agrees with the noncompetitive inhibition mechanism exhibited by p-methoxytacripyrine 11. Tacripyrines are neuroprotective agents, show moderate Ca2+ channel blocking effect, and cross the blood-brain barrier, emerging as lead candidates for treating AD.
• Synthesis of 6-amino-1,4-dihydropyridines that prevent calcium overload and neuronal death
  作者：Rafael León、Cristóbal de los Ríos、José Marco-Contelles、Manuela G. López、Antonio G. García、Mercedes Villarroya

  DOI：10.1016/j.ejmech.2007.06.001

  日期：2008.3

  The synthesis and pharmacology of 6-amino-1,4-dihydropyridines, such as ethyl 6-amino-4-aryl-5-cyano-1,4-dihydro-2-methyl-3-pyridinecarboxylic acids (3-16) and 2-amino-4-aryl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinenitriles (17-21) are described. Compounds 18 and 21, at the concentration of 0.3 mu M, proved to be the best blockers of the [Ca2+] overload induced by depolarization with high [K+] of SH-SY5Y neuroblastoma cells, with values of 63.8% and 50.4%, respectively. Most of the compounds induced a remarkable neuroprotective effect against toxicity caused by high [K+]-elicited [Ca2+] overload, and against H2O2-generated free radicals, in SH-SY5Y cells. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Visible-Light-Promoted Iminyl-Radical Formation from Acyl Oximes: A Unified Approach to Pyridines, Quinolines, and Phenanthridines
  作者：Heng Jiang、Xiaode An、Kun Tong、Tianyi Zheng、Yan Zhang、Shouyun Yu

  DOI：10.1002/anie.201411342

  日期：2015.3.23

  iminyl‐radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac‐[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e− reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N‐containing arenes. These reactions proceeded with a broad

  已经建立了涉及可见光诱导的亚胺基自由基形成的统一策略，用于从酰基肟中构建吡啶，喹啉和菲啶。用FAC - [的Ir（ppy）3 ]作为催化剂photoredox，酰基肟通过1e中转化-还原成亚氨基自由基中间体，然后行分子内均裂芳族取代（HAS），得到含有N-芳烃其中。这些反应在室温下以宽范围的底物以高收率进行。这种可见光诱导的亚胺基自由基形成策略已成功地应用于五步精简合成苯并[ c ]菲啶生物碱。