(E)-5-oxo-7-phenylhept-6-enoic acid | 33407-50-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-5-oxo-7-phenylhept-6-enoic acid
• CAS: 33407-50-0
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: DIASUNJAIMMROO-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-oxo-7-phenylhept-6-enoic acid 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 葡萄糖 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 水 、 苯 为溶剂， 反应 16.0h， 生成 Acetic acid (S)-5-hydroxy-7-phenyl-heptyl ester
  参考文献：
  名称：

  Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids

  摘要：

  gamma- and delta-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3 ,4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid: the delta-lactones were always obtained in an ee% higher than the gamma-lactones and ranging from 70% to 100%.

  DOI：

  10.1016/s0040-4020(01)81944-x
• 作为产物：
  描述：

  4-氯甲酰基丁酸甲酯 在 sodium hexamethyldisilazane 、 sodium iodide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙腈 为溶剂， 反应 37.0h， 生成 (E)-5-oxo-7-phenylhept-6-enoic acid
  参考文献：
  名称：

  5-Oxo-ETE Receptor Antagonists

  摘要：

  5-Oxo-ETE is the most powerful eosinophil chemoattractant among lipid mediators. Eosinophil infiltration into the lungs of asthmatics may be responsible for the late phase of inflammatory asthma. We have designed and synthesized a 5-oxo-ETE receptor antagonist, the purpose of which is to prevent eosinophil migration to the lung during an asthma attack and thereby reduce asthma symptoms.

  DOI：

  10.1021/jm400480j

文献信息

• Discovery of Novel Peptidomimetics as Irreversible CHIKV NsP2 Protease Inhibitors Using Quantum Mechanical-Based Ligand Descriptors
  作者：Eman M. El-labbad、Mohammed A. H. Ismail、Dalal A. Abou Ei Ella、Marawan Ahmed、Feng Wang、Khaled H. Barakat、Khaled A. M. Abouzid

  DOI：10.1111/cbdd.12621

  日期：2015.12

  headache, nausea, vomiting, myalgia, rash, and chronic persistent arthralgia. To date, no vaccines or selective antiviral drugs against this important emerging virus have been reported. In this study, the design, synthesis, and antiviral activity screening of new topographical peptidomimetics revealed three potential prototype agents 3a, 4b, and 5d showing 93–100% maximum inhibition of CHIKV replication

  基孔肯雅病毒（CHIKV）是一种由蚊子传播的甲病毒。在亚洲，非洲和欧洲已经报道了最近爆发的CHIKV感染。CHIKV感染的症状包括发烧，头痛，恶心，呕吐，肌痛，皮疹和慢性持续性关节痛。迄今为止，还没有针对这种重要的新兴病毒的疫苗或选择性抗病毒药物的报道。在这项研究中，新的地形模拟肽的设计，合成和抗病毒活性筛选揭示了三种潜在的原型药物3a，4b和5d，在基于细胞的测定中EC 90的EC 90为8.76–9.57的情况下，其对CHIKV复制的最大抑制作用为93–100％。  μ克/毫升。深入的分子建模研究包括共价对接，最低的未占据分子轨道能量和原子浓缩的Fukui函数计算，强烈暗示拟肽3a，4b和5d与CHIKV nsP2蛋白酶共价结合，从而通过α /之间的迈克尔加合物形成而使酶永久失活。我们设计的拟肽和活性部位催化半胱氨酸1013中的β-不饱和酮官能团。此外，小分子拟肽3a和4b的类药物满足
• Oxidation of diethyl ω-phenylalkenylmalonates by high valent metal salts.
  作者：Attilio Citterio、Roberto Sebastiano、Marco Nicolini

  DOI：10.1016/s0040-4020(01)87248-3

  日期：1993.8

  The oxidation of diethyl ω-phenylalkenylmalonates by Mn(III) acetate in acetic acid and Fe(III) perchlorate nonahydrate in acetonitrile or acetonitrile/acetic anhydride is investigated. Diethyl cinnamylmalonates 1, 2 and 3 afford intramolecular addition products to the double bond (cyclopropanes 10) and to the aromatic ring (tetrahydronaphthalenes 8 or 9). A mechanism based on a fast and reversible

  研究了乙酸Mn（III）在乙酸中和高氯酸Fe（III）九水合在乙腈或乙腈/乙酸酐中对ω-苯基烯基丙二酸二乙酯的氧化作用。二cinnamylmalonates 1，2和3得到的分子内的加成产物的双键（环丙烷10）并和该芳香环（四氢萘8或9）。基于快速的和可逆的3-机制外-trig公司丙二酰自由基导致的-addition顺反建议平衡双键，然后进行苄基自由基的氧化和分子内芳族取代之间的竞争。用苯乙烯和金属离子进行的捕集实验阐明了所涉及的一些动力学参数。同样，化合物4和5被Mn（III）/ AcOH和FEP / AN氧化为4-和5- exo-trig-环化产物。与此相反，外球电子转移机制建议在氧化1，4和5在由FEP / AN-AC苯乙烯双键2 O和benzalketones的6和7的Mn（III）/ AcOH中，以α氧合产物21–22。
• 5-Oxo-ETE Receptor Antagonists
  作者：Vivek Gore、Pranav Patel、Chih-Tsung Chang、Sashikala Sivendran、Namin Kang、Yannick P. Ouedraogo、Sylvie Gravel、William S. Powell、Joshua Rokach

  DOI：10.1021/jm400480j

  日期：2013.5.9

  5-Oxo-ETE is the most powerful eosinophil chemoattractant among lipid mediators. Eosinophil infiltration into the lungs of asthmatics may be responsible for the late phase of inflammatory asthma. We have designed and synthesized a 5-oxo-ETE receptor antagonist, the purpose of which is to prevent eosinophil migration to the lung during an asthma attack and thereby reduce asthma symptoms.
• Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids
  作者：Mario Aquino、Silvia Cardani、Giovanni Fronza、Claudio Fuganti、Rosalino Pulido Fernandez、Auro Tagliani

  DOI：10.1016/s0040-4020(01)81944-x

  日期：1991.9

  gamma- and delta-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3 ,4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid: the delta-lactones were always obtained in an ee% higher than the gamma-lactones and ranging from 70% to 100%.