1-phenylhept-6-yn-2-one | 1566092-67-8

• 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: 1-phenylhept-6-yn-2-one
• 英文别名: 1-Phenylhept-6-yn-2-one
• CAS: 1566092-67-8
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: JFSNITLCDBLWPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenylhept-6-yn-2-one 在 sodium tetrahydroborate 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.42h， 生成 1-phenylhept-6-yn-2-yl 2-diazo-2-(diethoxyphosphoryl)acetate
  参考文献：
  名称：

  A One-Pot C–H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones

  摘要：

  A one-pot C-H insertion/olefination sequence for the conversion of alpha-diazo-alpha-(dialkoxyphosphoryl)acetates into alpha-alkylidene-gamma-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.

  DOI：

  10.1021/ol501092m
• 作为产物：
  描述：

  5-己炔酸 在 1-丙基磷酸酐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 1-phenylhept-6-yn-2-one
  参考文献：
  名称：

  A One-Pot C–H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones

  摘要：

  A one-pot C-H insertion/olefination sequence for the conversion of alpha-diazo-alpha-(dialkoxyphosphoryl)acetates into alpha-alkylidene-gamma-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.

  DOI：

  10.1021/ol501092m

文献信息

• α-Methylene-γ-butyrolactones attenuate Staphylococcus aureus virulence by inhibition of transcriptional regulation
  作者：Martin H. Kunzmann、Nina C. Bach、Bianca Bauer、Stephan A. Sieber

  DOI：10.1039/c3sc52228h

  日期：——

  Bacterial pathogenesis is triggered by complex molecular mechanisms that sense bacterial density within an infected host and induce the expression of toxins for overriding the immune response. Virulence is controlled by a set of transcriptional regulators that directly bind to DNA promoter regions of toxin-encoding genes. Here, we identified an α-methylene-γ-butyrolactone as a potent inhibitor of Staphylococcus aureus virulence. Treatment of bacteria not only resulted in a markedly decreased expression of one of the most prominent virulence factors α-hemolysin (Hla) but also caused attenuated invasion efficiency. Mass spectrometry (MS) based target identification revealed this biological effect originating from the consolidated binding to three important transcriptional regulators SarA, SarR and MgrA. MS investigation of the binding site uncovered a conserved cysteine in all three proteins which gets covalently modified. Intriguingly, investigation of DNA binding demonstrated an impaired DNA-protein interaction upon compound treatment. The functional correlation between target binding, inhibition and the observed biological effect was proven by gene knockouts and confirmed the expected mode of action.

  细菌致病性是由复杂的分子机制触发的，这些机制感知感染宿主内的细菌密度，并诱导毒素的表达，以压制免疫反应。致病性由一套转录调控因子控制，这些因子直接结合在编码毒素基因的DNA启动子区域。在此，我们鉴定出一种α-亚甲基-γ-丁内酯作为金黄色葡萄球菌致病性的强效抑制剂。对细菌的处理不仅显著降低了最突出的致病因子α-溶血素（Hla）的表达，还导致侵袭效率减弱。基于质谱（MS）的靶向鉴定揭示了这种生物效应源自于对三个重要转录调控因子SarA、SarR和MgrA的紧密结合。对结合部位的质谱调查发现，在这三种蛋白中都存在一个保守的半胱氨酸，该半胱氨酸被共价修饰。引人注目的是，DNA结合的调查表明，在化合物处理后DNA-蛋白质相互作用受到损害。通过基因敲除证明了靶向结合、抑制和观察到的生物效应之间的功能相关性，从而确认了预期的作用机制。
• A One-Pot C–H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones
  作者：Matthew G. Lloyd、Richard J. K. Taylor、William P. Unsworth

  DOI：10.1021/ol501092m

  日期：2014.5.16

  A one-pot C-H insertion/olefination sequence for the conversion of alpha-diazo-alpha-(dialkoxyphosphoryl)acetates into alpha-alkylidene-gamma-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.