4-(1-萘基)-4-氧代丁酸乙酯 | 73931-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(1-萘基)-4-氧代丁酸乙酯
• 英文名称: ethyl 4-(naphthalen-1-yl)-4-oxobutanoate
• 英文别名: ethyl 4-(1-naphthyl)-4-oxobutanoate；Ethyl 4-(1-naphthyl)-4-oxobutyrate；ethyl 4-naphthalen-1-yl-4-oxobutanoate
• CAS: 73931-66-5
• 化学式: C₁₆H₁₆O₃
• mdl: MFCD01320262
• 分子量: 256.301
• InChiKey: XWRHWEPJARAHBP-UHFFFAOYSA-N

物化性质

• 沸点：
  419.3±28.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  甲基三苯基溴化膦 、 4-(1-萘基)-4-氧代丁酸乙酯 在 potassium tert-butylate 作用下， 生成
  参考文献：
  名称：

  ortho-Halogeno Substituents Effect in Asymmetric Cyclization of 4-Aryl-4-pentenals Using a Rhodium Catalyst

  摘要：

  使用阳离子[Rh((R)-BINAP)]ClO4对4-芳基-4-戊烯醛的不对称环化反应生成了(3R)-3-取代的环戊酮；另一方面，带有邻卤素苯基的4-戊烯醛环化反应则生成了相反的(3S)-产物。

  DOI：

  10.1246/cl.1998.881
• 作为产物：
  描述：

  3-碘丙酸乙酯 、 1-萘甲酰氯 在 四(三苯基膦)钯 、 锌铜偶 作用下， 生成 4-(1-萘基)-4-氧代丁酸乙酯
  参考文献：
  名称：

  ortho-Halogeno Substituents Effect in Asymmetric Cyclization of 4-Aryl-4-pentenals Using a Rhodium Catalyst

  摘要：

  使用阳离子[Rh((R)-BINAP)]ClO4对4-芳基-4-戊烯醛的不对称环化反应生成了(3R)-3-取代的环戊酮；另一方面，带有邻卤素苯基的4-戊烯醛环化反应则生成了相反的(3S)-产物。

  DOI：

  10.1246/cl.1998.881

文献信息

• Intermolecular Addition Reaction to Alkenes of Acylmolybdenum Complexes Generated by Oxidative Addition of Aryl or Alkenyl Halides with Molybdenum(0) Carbonyl Complexes
  作者：Nobuharu Iwasawa、Kenichiro Sangu、Toru Watanabe、Jun Takaya

  DOI：10.1055/s-2007-973858

  日期：2007.4

  Acylmolybdenum species, generated by oxidative addition of aryl or alkenyl halides with molybdenum(0) carbonyl complex followed by carbon monoxide insertion, added to various kinds of alkenes intermolecularly to give simple addition products in good yields without formation of carbonylative Heck-type products.

  酰基钼物种，通过芳基或烯基卤化物与钼 (0) 羰基络合物的氧化加成，然后插入一氧化碳，分子间添加到各种烯烃中，以良好的收率得到简单的加成产物，而不会形成羰基化的 Heck 型产物。
• π-Interactions as a tool for an easy deposition of meso-tetraferrocenylporphyrin on surfaces
  作者：Andrea Vecchi、Valentina Grippo、Barbara Floris、Andrea Giacomo Marrani、Valeria Conte、Pierluca Galloni

  DOI：10.1039/c3nj00519d

  日期：——

  A bottom-up approach was employed to prepare novel Self-Assembled Monolayers (SAMs) in which a naphthyl moiety acted as a “π-binder” for unfunctionalised meso-tetraferrocenylporphyrin (H2TFcP). Four naphthalene derivatives with an appropriate functional group were synthesized and SAMs were prepared both on gold and ITO surfaces. Mixed H2TFcP–naphthalene films were thoroughly characterized using UV-Vis, XPS and electrochemical techniques. In particular, angle-dependent XPS experiments revealed an almost perpendicular orientation of the porphyrin on surfaces, suggesting that an intercalation occurred among naphthalene units. A large amount of porphyrin was deposited on both the surfaces (in the order of 10−10 mol × cm−2), comparable to that afforded by more conventional covalent linkages. However, significant differences in homogeneity between SAMs on gold and ITO resulted in a diverse electrochemical behaviour. The electrochemical activity of the oxidised porphyrin was restored by prolonged exposure of the modified gold electrode (tens of seconds) to a negative potential, whereas no response was detected after the same treatment on ITO. This novel approach provides a general and versatile strategy to bind meso-substituted porphyrins on a pre-formed monolayer without the necessity for further functionalisations.

  我们采用了一种自下而上的方法来制备新型自组装单层膜（SAMs），其中萘基是未官能化的中-四铁卟啉（H2TFcP）的 "粘合剂"。我们合成了四种具有适当官能团的萘衍生物，并在金和 ITO 表面制备了 SAM。使用紫外可见光、XPS 和电化学技术对混合 H2TFcPânaphthalene 薄膜进行了全面表征。其中，与角度相关的 XPS 实验显示，卟啉在表面的取向几乎是垂直的，这表明萘单元之间发生了插层。大量卟啉沉积在两个表面上（约为 10â10 mol à cmâ2），与更传统的共价连接所产生的卟啉量相当。然而，金和 ITO 上的 SAMs 在均匀性方面的显著差异导致了电化学行为的多样性。将修饰过的金电极长时间暴露在负电位下（数十秒），氧化卟啉的电化学活性就会恢复，而在 ITO 上进行相同处理后，则检测不到任何反应。这种新方法提供了一种通用的多用途策略，可将中取代卟啉结合到预先形成的单层上，而无需进一步的功能化处理。
• RETRACTED ARTICLE: IspH inhibitors kill Gram-negative bacteria and mobilize immune clearance
  作者：Kumar Sachin Singh、Rishabh Sharma、Poli Adi Narayana Reddy、Prashanthi Vonteddu、Madeline Good、Anjana Sundarrajan、Hyeree Choi、Kar Muthumani、Andrew Kossenkov、Aaron R. Goldman、Hsin-Yao Tang、Maxim Totrov、Joel Cassel、Maureen E. Murphy、Rajasekharan Somasundaram、Meenhard Herlyn、Joseph M. Salvino、Farokh Dotiwala

  DOI：10.1038/s41586-020-03074-x

  日期：2021.1.28

  Isoprenoids are vital for all organisms, in which they maintain membrane stability and support core functions such as respiration1. IspH, an enzyme in the methyl erythritol phosphate pathway of isoprenoid synthesis, is essential for Gram-negative bacteria, mycobacteria and apicomplexans2,3. Its substrate, (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMBPP), is not produced in metazoans, and in humans and other primates it activates cytotoxic Vγ9Vδ2 T cells at extremely low concentrations4–6. Here we describe a class of IspH inhibitors and refine their potency to nanomolar levels through structure-guided analogue design. After modification of these compounds into prodrugs for delivery into bacteria, we show that they kill clinical isolates of several multidrug-resistant bacteria—including those from the genera Acinetobacter, Pseudomonas, Klebsiella, Enterobacter, Vibrio, Shigella, Salmonella, Yersinia, Mycobacterium and Bacillus—yet are relatively non-toxic to mammalian cells. Proteomic analysis reveals that bacteria treated with these prodrugs resemble those after conditional IspH knockdown. Notably, these prodrugs also induce the expansion and activation of human Vγ9Vδ2 T cells in a humanized mouse model of bacterial infection. The prodrugs we describe here synergize the direct killing of bacteria with a simultaneous rapid immune response by cytotoxic γδ T cells, which may limit the increase of antibiotic-resistant bacterial populations. A class of compounds with a dual mechanism of action—direct targeting of IspH and stimulation of cytotoxic γδ T cells to enhance pathogen clearance—are active against multidrug-resistant bacteria.

  异丙肾上腺素对所有生物都至关重要，它们能维持膜的稳定性并支持呼吸等核心功能1。IspH 是异戊二烯合成途径中赤藓醇磷酸甲酯途径的一种酶，对革兰氏阴性菌、分枝杆菌和类鼻疽杆菌至关重要2,3。它的底物(E)-4-羟基-3-甲基-丁-2-烯基焦磷酸（HMBPP）在元类动物中不产生，而在人类和其他灵长类动物中，它能在极低浓度下激活细胞毒性 Vδ9Vδ2 T 细胞4â6。在这里，我们描述了一类 IspH 抑制剂，并通过结构引导的类似物设计将其药效提高到纳米级水平。我们将这些化合物改性为原药，并将其输送到细菌体内，结果表明，它们能杀死多种耐多药细菌的临床分离株，包括不动杆菌属、假单胞菌属、克雷伯氏菌属、肠杆菌属、弧菌属、志贺氏菌属、沙门氏菌属、耶尔森氏菌属、分枝杆菌属和芽孢杆菌属的细菌，但对哺乳动物细胞相对无毒。蛋白质组分析表明，使用这些原药处理的细菌与条件性 IspH 基因敲除后的细菌相似。值得注意的是，在人源化小鼠细菌感染模型中，这些原药还能诱导人类 Vδ9Vδ2 T 细胞的扩增和活化。我们在此介绍的这些原药在直接杀灭细菌的同时，还能协同细胞毒性δδT 细胞产生快速免疫反应，这可能会限制抗生素耐药细菌数量的增加。一类具有双重作用机制（直接靶向 IspH 和刺激细胞毒性 δδ´ T 细胞以提高病原体清除率）的化合物对多重耐药细菌具有活性。
• Nagasaka, Tatsuo; Hamaguchi, Fumiko; Ozawa, Naganori, Heterocycles, 1980, vol. 14, # 3, p. 291 - 293
  作者：Nagasaka, Tatsuo、Hamaguchi, Fumiko、Ozawa, Naganori、Kosugi, Yoshiyuki、Ohki, Sadao

  DOI：——

  日期：——
• ortho-Halogeno Substituents Effect in Asymmetric Cyclization of 4-Aryl-4-pentenals Using a Rhodium Catalyst
  作者：Masakazu Fujio、Masakazu Tanaka、Xiao-Ming Wu、Kazuhisa Funakoshi、Kiyoshi Sakai、Hiroshi Suemune

  DOI：10.1246/cl.1998.881

  日期：1998.9

  Asymmetric cyclization of 4-aryl-4-pentenals by using a cationic [Rh((R)-BINAP)]ClO4 afforded (3R)-3-substituted cyclopentanones; on the other hand, the cyclization of 4-pentenals bearing ortho-halogeno phenyl groups afforded the opposite (3S)-ones.

  使用阳离子[Rh((R)-BINAP)]ClO4对4-芳基-4-戊烯醛的不对称环化反应生成了(3R)-3-取代的环戊酮；另一方面，带有邻卤素苯基的4-戊烯醛环化反应则生成了相反的(3S)-产物。