4-蒽-9-基丁-3-烯-2-酮 | 92683-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 4-蒽-9-基丁-3-烯-2-酮
• 英文名称: 4-(anthracen-9-yl)but-3-en-2-one
• 英文别名: 4-(Anthracen-9-YL)but-3-EN-2-one；4-anthracen-9-ylbut-3-en-2-one
• CAS: 92683-48-2
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: ADVWEJQAXPKANJ-UHFFFAOYSA-N

物化性质

• 熔点：
  113 °C
• 沸点：
  464.5±14.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-蒽-9-基丁-3-烯-2-酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以99%的产率得到4-anthracen-9-ylbut-3-en-2-ol
  参考文献：
  名称：

  Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reaction progress by an increase in fluorescence

  摘要：

  The development of fluorogenic probes for chemical transformations bearing anthracene as a fluorescent core moiety is reported. Fluorogenic probes were designed by linking anthracene with functional groups used for reactions of interest. Each fluorogenic probe, possessing a reaction group such as aldehyde, alpha,beta-unsaturated ketone, or imine at the 9-position of the anthracene, showed no or very low fluorescence. Reaction products of the probes, including aldol and addition products, were highly fluorescent. The products showed more than 1000-fold higher fluorescence than did the fluorogenic probes under the same conditions. The utility of the fluorogenic probes was demonstrated in monitoring the progress of a catalyzed aldol reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.010
• 作为产物：
  描述：

  丙酮 、 9-蒽甲醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 4-蒽-9-基丁-3-烯-2-酮
  参考文献：
  名称：

  甲基酮作为卤代烷替代物：一种用于战略性官能团转化的脱酰卤化方法

  摘要：

  卤代烷是获得多种官能团 (FG) 的通用前体。由于其不稳定性，卤代烷替代物的开发对于复杂分子的合成具有重要的战略意义。鉴于常见烷基酮固有的稳定性和易于衍生化的特点，我们在此报告了一种脱酰卤化方法，可将各种甲基酮转化为相应的烷基氯、溴化物和碘化物。该反应是通过形成芳香族副产物（即 1,2,4-三唑）来驱动的，其中使用N'-甲基吡啶甲酰肼酰胺 (MPHA) 形成前芳香族中间体，并使用卤素原子转移 (XAT) 试剂来猝灭反应。烷基中间体。该反应可有效地从多种甲基酮中生成伯烷基卤和仲烷基卤，并具有广泛的 FG 耐受性。它还适用于复杂的天然产物衍生和含氟基材。此外，还实现了甲基酮一锅法转化为各种其他FG，以及通过脱酰卤化与烯烃和炔烃成环。此外，还证明了烷基碘的不寻常的迭代同系化。最后，机理研究揭示了脱酰碘化反应的一个有趣的双 XAT 过程，这可能具有超出本工作范围的影响。

  DOI：

  10.1021/jacs.3c08176

文献信息

• Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights
  作者：Atsushi Ueda、Tomohiro Umeno、Mitsunobu Doi、Kengo Akagawa、Kazuaki Kudo、Masakazu Tanaka

  DOI：10.1021/acs.joc.6b00982

  日期：2016.8.5

  Helical peptide foldamer catalyzed Michael addition reactions of nitroalkane or dialkyl malonate to α,β-unsaturated ketones are reported along with the mechanistic considerations of the enantio-induction. A wide variety of α,β-unsaturated ketones, including β-aryl, β-alkyl enones, and cyclic enones, were found to be catalyzed by the helical peptide to give Michael adducts with high enantioselectivities

  报道了螺旋肽折叠剂催化硝基烷或丙二酸二烷基酯与α，β-不饱和酮的迈克尔加成反应，以及对映体诱导的机理考虑。发现各种α，β-不饱和酮，包括β-芳基，β-烷基烯酮和环状烯酮，都可以被螺旋肽催化，从而得到具有高对映选择性（高达99％）的迈克尔加合物。根据X射线晶体学分析和depsipeptide研究，α-螺旋肽催化剂N端的酰胺质子N（2）–H和N（3）–H对激活迈克尔供体至关重要，而N-末端伯胺通过亚胺离子中间体的形成激活了迈克尔受体。
• Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO
  作者：Nobuyuki Mase、Taishi Ando、Fumiya Shibagaki、Atsushi Sugita、Tetsuo Narumi、Mitsuo Toda、Naoharu Watanabe、Fujie Tanaka

  DOI：10.1016/j.tetlet.2014.02.007

  日期：2014.3

  Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions. (c) 2014 Elsevier Ltd. All rights reserved.
• Boehmite—An Efficient and Recyclable Acid-Base Bifunctional Catalyst for Aldol Condensation Reaction
  作者：P. C. Rajan Reshma、Sekar Vikneshvaran、Sivan Velmathi

  DOI：10.1166/jnn.2018.15205

  日期：2018.6.1

  In this work boehmite was used as an acid-base bifunctional catalyst for aldol condensation reactions of aromatic aldehydes and ketones. The catalyst was prepared by simple sol-gel method using Al(NO3)(3)center dot 9H(2)O and NH4OH as precursors. The catalyst has been characterized by X-ray diffraction (XRD), Fourier Transform Infrared (FTIR), Scanning Electron Microscopy (SEM), UV-visible spectroscopy (DRS), BET surface area analyses. Boehmite is successfully applied as catalyst for the condensation reaction between 4-nitrobenzaldehyde and acetone as a model substrate giving alpha,beta-unsaturated ketones without any side product. The scope of the reaction is extended for various substituted aldehydes. A probable mechanism has been suggested to explain the cooperative behavior of the acidic and basic sites. The catalyst is environmentally friendly and easily recovered from the reaction mixture. Also the catalyst is reusable up to 3 catalytic cycles.
• Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reaction progress by an increase in fluorescence
  作者：Nobuyuki Mase、Kunihiko Takabe、Fujie Tanaka

  DOI：10.1016/j.tetlet.2013.06.010

  日期：2013.8

  The development of fluorogenic probes for chemical transformations bearing anthracene as a fluorescent core moiety is reported. Fluorogenic probes were designed by linking anthracene with functional groups used for reactions of interest. Each fluorogenic probe, possessing a reaction group such as aldehyde, alpha,beta-unsaturated ketone, or imine at the 9-position of the anthracene, showed no or very low fluorescence. Reaction products of the probes, including aldol and addition products, were highly fluorescent. The products showed more than 1000-fold higher fluorescence than did the fluorogenic probes under the same conditions. The utility of the fluorogenic probes was demonstrated in monitoring the progress of a catalyzed aldol reaction. (C) 2013 Elsevier Ltd. All rights reserved.