1-(二氰基亚甲基)-2-氧代苊 | 14619-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(二氰基亚甲基)-2-氧代苊
• 英文名称: 2-(2-oxo-2H-acenaphthylen-1-ylidene)malononitrile
• 英文别名: 2-(2-oxoacenaphthylen-1(2H)-ylidene)malononitrile；2-(2-oxo-2H-acenaphthylene-1-ylidene)malononitrile；1-Dicyanmethylen-acenaphthen-2-on；delta(sup 1),alpha-Acenaphthenemalononitrile, 2-oxo-；2-(2-oxoacenaphthylen-1-ylidene)propanedinitrile
• CAS: 14619-86-4
• 化学式: C₁₅H₆N₂O
• 分子量: 230.225
• InChiKey: WYZUQHDRPNJOCG-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  423.6±45.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  1-(二氰基亚甲基)-2-氧代苊 在 溴 、 potassium carbonate 、 三氯化磷 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 3-(2-bromoethylamino)-8-oxo-8H-cyclopenta[a]acenaphthylene-7-carbonitrile
  参考文献：
  名称：

  Synthesis and evaluation of novel 8-oxo-8H-cyclopenta[a]acenaphthylene-7-carbonitriles as long-wavelength fluorescent markers for hypoxic cells in solid tumor

  摘要：

  Novel bioreductive and long-wavelength fluorescent markers for hypoxic cells in solid tumor, 9-isocyano-8H-acenaphtho[1,2-b]pyrrol-8-one with the side chain of 2-nitroimidazole, were designed, synthesized, and evaluated in V79 379A Chinese hamster cells in vitro. Compounds A(2) and A(4) showed good hypoxic-oxic fluorescence differential in vitro (V79 cells) by using fluorescence scan ascent. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.031
• 作为产物：
  描述：

  2-dimethoxyphosphoryl-2-(2-oxo-1H-acenaphthylen-1-yl)propanedinitrile 以72%的产率得到
  参考文献：
  名称：

  MAHRAN, MOHAMED R.;ABDOU, WAFAA M.;GANOUB, NEVEN A. F.;ABDALLAH, HISHAM A+, PHOSPH., SULFUR AND SILICON AND RELAT. ELEM., 57,(1991) N-4, C. 217-225

  摘要：

  DOI：

文献信息

• A dynamic invertible intramolecular charge-transfer fluorescence probe: real-time monitoring of mitochondrial ATPase activity
  作者：Hua Zhang、Yafu Wang、Xiaopeng Xuan、Ge Wang、Haiming Guo、Jiangli Fan

  DOI：10.1039/c7cc02450a

  日期：——

  A dynamic invertible intramolecular charge-transfer fluorescence probe was successfully utilized for the real-time monitoring of mitochondrial ATPase activity.

  一种动态可逆的分子内电荷转移荧光探针成功用于监测线粒体ATP酶活性的实时监测。
• Light-induced activities of novel naphtho[1,8-ef]isoindole-7,8,10(9H)-trione and oxoisoaporphine derivatives towards mosquito larvae
  作者：Qi Xu、Hao Feng、Xusheng Shao

  DOI：10.1016/j.bmcl.2021.128225

  日期：2021.9

  oxygen produced by photosensitizer through irradiation. However, the choice of photosensitizer for mosquito control is limited. Here, we report a novel series of naphtho[1,8-ef]isoindole-7,8,10(9H)-trione and oxoisoaporphines derivatives as excellent type II photosensitizers. Meanwhile, the light-dependent activities against permethrin-susceptible and permethrin-resistant strain of Aedes aegypti mosquito

  受感染的蚊子是登革热、黄热病、基孔肯雅热、寨卡病毒和其他病原体的重要载体。从增加蚊子幼虫控制的抗性来看，光活化杀虫剂是一种利用光敏剂通过辐照产生的剧毒单线态氧的有前途的方法。然而，用于控制蚊子的光敏剂的选择是有限的。在这里，我们报告了一系列新的萘并[1,8 - ef ] isoindole -7,8,10(9 H )-trione 和oxoisoaporphine 衍生物作为优秀的II 型光敏剂。同时，对埃及伊蚊对氯菊酯敏感和氯菊酯抗性菌株的光依赖活性对这些化合物的蚊子幼虫进行了评估。其中，化合物7b由于其优异的光毒性被证明是潜在的光动力杀虫剂，可见光照射下LC 50值为0.19 μg mL -1。辐射产生的活性增强超过 520 倍。这种化合物可能是寻找新的光活化杀虫剂线索的潜在候选者。重要的是，7b 具有良好的荧光量子产率（φ F  = 0.70），可作为蚊子幼虫的荧光指示剂，观察吸收和形态变化。
• 1-Oxo-1<i>H</i>-phenalene-2,3-dicarbonitrile Heteroaromatic Scaffold: Revised Structure and Mechanistic Studies
  作者：Romaric Lenk、Arnaud Tessier、Pierre Lefranc、Virginie Silvestre、Aurélien Planchat、Virginie Blot、Didier Dubreuil、Jacques Lebreton

  DOI：10.1021/jo5016932

  日期：2014.10.17

  Synthesis of the originally proposed 8-oxo-8H-acenaphtho[1,2-b]pyrrol-9-carbonitrile led to a structural revision, and the product has now been identified as unknown compound 1-oxo-1H-phenalene-2,3-dicarbonitrile. The structural assignment was corroborated by detailed NMR studies and unambiguously confirmed by X-ray diffraction. A mechanism is proposed to explain the formation of this original heterocyclic

  最初提出的8-oxo-8 H -ac [1,2 - b ]吡咯-9-甲腈的合成导致结构改变，该产品现已鉴定为未知化合物1-oxo-1 H -phenalene- 2,3-二碳腈。通过详细的NMR研究证实了结构归属，并通过X射线衍射明确证实了该结构归属。提出了一种机制来解释这种原始的杂环支架的形成。另外，提出了一些涉及该化合物的新化学转化。
• One-Pot Synthesis of Biologically Important Spiro-2-amino-4<i>H</i>-pyrans, Spiroacenaphthylenes, and Spirooxindoles Using DBU as a Green and Recyclable Catalyst in Aqueous Medium
  作者：Pooja Saluja、Komal Aggarwal、Jitender M. Khurana

  DOI：10.1080/00397911.2012.760130

  日期：2013.12.17

  Abstract We have reported DBU-catalyzed one-pot synthesis of biologically and pharmacologically important spiropyrans from condensation of malononitrile/ethyl cyanoacetate, 1,3-dicarbonyl compounds, and ninhydrin/acenaphthequinone/istain in good yields. This new protocol employing DBU, which is a green, recyclable, and inexpensive catalyst, offers advantages such as mild reaction conditions, short

  摘要 我们已经报道了 DBU 催化从丙二腈/氰基乙酸乙酯、1,3-二羰基化合物和茚三酮/苊醌/伊斯坦酮缩合合成具有生物学和药理学意义的螺吡喃，收率良好。这种采用 DBU 的新方案是一种绿色、可回收且价格低廉的催化剂，具有反应条件温和、反应时间短和易于分离产物等优点。这些结构已通过 X 射线分析得到证实。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• One-pot, sequential four-component synthesis of novel heterocyclic [3.3.3] propellane derivatives at room temperature
  作者：Maryam Beyrati、Alireza Hasaninejad

  DOI：10.1039/c8ra01648h

  日期：——

  An efficient, one-pot, two-step, four-component reaction for the synthesis of propellane derivatives is described by the condensation reaction between acenaphthenequinone, malono derivatives, primary amines and β-ketoester or β-diketone derivatives in the presence of triethylamine in ethanol at room temperature. Using this procedure, all the products were obtained in good to excellent yields.

  通过苊醌、丙二酸衍生物、伯胺与β-酮酯或β-二酮衍生物在三乙胺存在下的缩合反应，描述了一种高效、一锅、两步、四组分合成丙丙烷衍生物的反应。室温下乙醇。使用该程序，所有产品均以良好至优异的产率获得。