4-(3-Methoxyphenyl)cyclohex-3-en-1-one | 147678-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-Methoxyphenyl)cyclohex-3-en-1-one
• 英文别名: 4-(3-methoxyphenyl)cyclohex-3-en-1-one
• CAS: 147678-66-8
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: KWERTTUNFFCHAH-UHFFFAOYSA-N

物化性质

• 沸点：
  349.5±42.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  4-(3-Methoxyphenyl)cyclohex-3-en-1-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 生成 4-(3-甲氧基苯基)环己酮
  参考文献：
  名称：

  Aryl extensions of thienopyrimidinones as fibroblast growth factor receptor 1 kinase inhibitors

  摘要：

  Optimization of thienopyrimidinone derivatives as FGFR1 kinase inhibitors is being pursued. The present results confirm predictions of computational modeling that an aryl substituent can be introduced at the 2-position in structure 3. The substituent is anticipated to project deeper into the binding site and provide opportunities for enhanced activity and selectivity. The most potent analog reported herein, 13, has a 4-hydroxyphenyl substituent and yields an IC(50) of 6 mu M for inhibition of phosphorylation by FGFR1 kinase. It was also found that the western anisole-containing substituent in 3 can be replaced by a propionic acid group with no loss in potency and with potentially significant gains in pharmacologically relevant properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.081
• 作为产物：
  描述：

  8-(3-甲氧基-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-醇 在 三氟乙酸 作用下， 反应 0.5h， 以90%的产率得到4-(3-Methoxyphenyl)cyclohex-3-en-1-one
  参考文献：
  名称：

  可见光介导的反式芳基环己烯的生成及其在环桥醚合成中的应用

  摘要：

  虽然可以通过顺式环己烯的紫外线照射获得，但反式环己烯迄今为止一直是由好奇心驱动的研究，主要是由于其寿命短，直到最近才被用于生产合成。在这里，我们提出了直接的条件，提供了获得一类反式芳基环己烯并证明它们在形成氧杂双环醚中的效用，否则相应的顺式环己烯是无法获得的。利用令人难以置信的 ca 的关键挑战。用于驱动合成的反式环己烯的 52 kcal/mol 应变能克服了其短寿命的问题。在这里，我们表明在异构化之前通过底物和反应伙伴之间的氢键进行预组织是克服反式环己烯固有的短寿命的可行策略。

  DOI：

  10.1021/jacs.8b04642

文献信息

• Desymmetrizing Isomerization of Alkene via Thiazolinyl Iminoquinoline Cobalt Catalysis
  作者：Wenbo Liu、Yushan Zheng、Yihui Mao、Jieping Chen、Xiang Ren、Zhaoyang Cheng、Zhan Lu

  DOI：10.1021/acs.orglett.1c04237

  日期：2022.2.11

  1-methylcyclohexene derivatives with good yields and enantioselectivities. A novel chiral thiazolinyl iminoquinoline ligand and its cobalt complex were designed and synthesized to control the establishment of tertiary or quaternary carbon centers at a remote position. This protocol is operationally simple, and a model for the stereochemical outcome has been proposed.

  我们报道了一种钴催化的外环烯烃去对称异构化，以产生具有良好收率和对映选择性的手性 1-甲基环己烯衍生物。设计并合成了一种新型手性噻唑啉基亚氨基喹啉配体及其钴配合物，以控制在偏远位置建立叔或季碳中心。该协议操作简单，并提出了立体化学结果的模型。
• Aryl extensions of thienopyrimidinones as fibroblast growth factor receptor 1 kinase inhibitors
  作者：Anil R. Ekkati、Valsan Mandiyan、Krishna P. Ravindranathan、Jae H. Bae、Joseph Schlessinger、William L. Jorgensen

  DOI：10.1016/j.tetlet.2010.12.081

  日期：2011.4

  Optimization of thienopyrimidinone derivatives as FGFR1 kinase inhibitors is being pursued. The present results confirm predictions of computational modeling that an aryl substituent can be introduced at the 2-position in structure 3. The substituent is anticipated to project deeper into the binding site and provide opportunities for enhanced activity and selectivity. The most potent analog reported herein, 13, has a 4-hydroxyphenyl substituent and yields an IC(50) of 6 mu M for inhibition of phosphorylation by FGFR1 kinase. It was also found that the western anisole-containing substituent in 3 can be replaced by a propionic acid group with no loss in potency and with potentially significant gains in pharmacologically relevant properties. (C) 2010 Elsevier Ltd. All rights reserved.
• Visible Light Mediated Generation of <i>trans</i>-Arylcyclohexenes and Their Utilization in the Synthesis of Cyclic Bridged Ethers
  作者：Jon I. Day、Kamaljeet Singh、Winston Trinh、Jimmie D. Weaver

  DOI：10.1021/jacs.8b04642

  日期：2018.8.8

  for productive synthesis. Herein, we present straightforward conditions that provide access to a class of trans-arylcyclohexenes and demonstrate their utility in the formation of oxabicyclic ethers, which are otherwise inaccessible from the corresponding cis-cyclohexene. A key challenge to utilizing the incredible ca. 52 kcal/mol strain energy of trans-cyclohexene to drive synthesis was overcoming

  虽然可以通过顺式环己烯的紫外线照射获得，但反式环己烯迄今为止一直是由好奇心驱动的研究，主要是由于其寿命短，直到最近才被用于生产合成。在这里，我们提出了直接的条件，提供了获得一类反式芳基环己烯并证明它们在形成氧杂双环醚中的效用，否则相应的顺式环己烯是无法获得的。利用令人难以置信的 ca 的关键挑战。用于驱动合成的反式环己烯的 52 kcal/mol 应变能克服了其短寿命的问题。在这里，我们表明在异构化之前通过底物和反应伙伴之间的氢键进行预组织是克服反式环己烯固有的短寿命的可行策略。