2-(1-naphthyl)-2-cyclopentenone | 108718-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-naphthyl)-2-cyclopentenone
• 英文别名: 1-naphth-1-ylcyclopent-2-enone；2-(naphthalen-1-yl)cyclopent-2-en-1-one；2-[1]naphthyl-cyclopent-2-enone；2-[1]Naphthyl-cyclopent-2-enon；2-Naphthalen-1-ylcyclopent-2-en-1-one；2-naphthalen-1-ylcyclopent-2-en-1-one
• CAS: 108718-84-9
• 化学式: C₁₅H₁₂O
• 分子量: 208.26
• InChiKey: XNKSSIVQBGPNAH-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  409.2±35.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2-(1-naphthyl)-2-cyclopentenone 在 lithium 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  The search for tolerant Lewis acid catalysts. Part 2: Enantiopure cycloalkyldialkylsilyl triflimide catalysts

  摘要：

  A series of 2-aryl-and arylmethyl-3-dialkylphenylsilyl cycloalkanones have been prepared and resolved. The pure enantiomers were reduced to the corresponding cycloalkane derivatives. These were used for the in situ generation of enantiopure cycloalkylsilyl triflimides by protodesilylation with bis( trifluoromethanesulfonyl) imide. The association of a bulky leaving group with a silicon atom carrying large substituents was again shown to favour the complexation of silicon with carbonyl groups: all these trialkylsilyl triflimides showed a high catalytic activity for Diels -Alder reactions. Enantiomeric excesses up to 59% were observed. This is the highest enantioselectivity ever observed for a Diels-Alder reaction catalysed by a silicon Lewis acid. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.086
• 作为产物：
  描述：

  1-溴代萘 在 叔丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 5.67h， 生成 2-(1-naphthyl)-2-cyclopentenone
  参考文献：
  名称：

  The search for tolerant Lewis acid catalysts. Part 2: Enantiopure cycloalkyldialkylsilyl triflimide catalysts

  摘要：

  A series of 2-aryl-and arylmethyl-3-dialkylphenylsilyl cycloalkanones have been prepared and resolved. The pure enantiomers were reduced to the corresponding cycloalkane derivatives. These were used for the in situ generation of enantiopure cycloalkylsilyl triflimides by protodesilylation with bis( trifluoromethanesulfonyl) imide. The association of a bulky leaving group with a silicon atom carrying large substituents was again shown to favour the complexation of silicon with carbonyl groups: all these trialkylsilyl triflimides showed a high catalytic activity for Diels -Alder reactions. Enantiomeric excesses up to 59% were observed. This is the highest enantioselectivity ever observed for a Diels-Alder reaction catalysed by a silicon Lewis acid. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.086

文献信息

• De Novo Synthesis of Benzannelated Heterocycles
  作者：Johannes Feierfeil、Thomas Magauer

  DOI：10.1002/chem.201705662

  日期：2018.1.26

  functionalize commercially available heterocycles or resort to transformations that make use of benzene‐derived building blocks. Here, we report a powerful cascade reaction that enables the de novo construction of variously substituted indoles, indazoles, benzofurans and benzothiophenes from readily available bicyclo[3.1.0]hexan‐2‐ones. The transformation can be conducted under mild, non‐anhydrous conditions

  苯并环杂环如吲哚和吲唑是在天然产物、药物和农用化学品中发现的重要结构基序。对于他们的合成，化学家传统上要么对市售的杂环进行功能化，要么求助于利用苯衍生的结构单元的转化。在这里，我们报告了一种强大的级联反应，该反应能够从容易获得的双环[3.1.0]hexan-2-ones 从头构建各种取代的吲哚、吲唑、苯并呋喃和苯并噻吩。转化可以在温和、无水的条件下进行。对于吲哚的合成，机理研究表明，双环系统的电环开环和芳构化先于 3,3-σ 重排。
• Diastereoselective Synthesis of Planar Chiral Phosphoramidites with a Ferrocenophane Scaffold
  作者：Mathilde Neel、Pascal Retailleau、Arnaud Voituriez、Angela Marinetti

  DOI：10.1021/acs.organomet.7b00700

  日期：2018.3.12

  A new family of planar chiral phosphoramidites with a [3]ferrocenophane structure was synthesized. The synthetic strategy involved diastereoselective formation of the chiral ferrocene units from suitable substituted bis-cyclopentadienyl derivatives. Preliminary coordination studies of these ligands were undertaken with the synthesis of palladium and platinum complexes.

  合成了具有[3]二茂铁结构的平面手性亚磷酰胺的新家族。合成策略包括由合适的取代的双环戊二烯基衍生物非对映选择性地形成手性二茂铁单元。这些配体的初步配位研究是通过钯和铂配合物的合成来进行的。
• Photochemical Reduction of Quinolines with γ-Terpinene
  作者：Souvik Adak、Sarah E. Braley、M. Kevin Brown

  DOI：10.1021/acs.orglett.3c04096

  日期：2024.1.12

  of complex rings. Herein, we demonstrate a process for photochemical dearomative reduction of quinolines. The process involves capture of a quinoline excited state with γ-terpinene. Importantly, the reaction is chemoselective as other easily reduced functionalities such as halogens or alkenes do not undergo reduction. The mechanism of the reaction has also been investigated. Finally, the generality of

  芳香支架的饱和对于复杂环的合成很有价值。在这里，我们展示了喹啉的光化学脱芳香还原过程。该过程涉及用 γ-萜品烯捕获喹啉激发态。重要的是，该反应具有化学选择性，因为其他容易还原的官能团（例如卤素或烯烃）不会发生还原。还研究了该反应的机理。最后，证明了该方法对其他基材的普遍性。
• The α-arylation of α-bromo- and α-chloroenones using palladium-catalysed cross-coupling
  作者：James C. Banks、David Van Mele、Christopher G. Frost

  DOI：10.1016/j.tetlet.2006.02.134

  日期：2006.4

  The palladium-catalysed cross-coupling reaction of various arylboronic acids with alpha-bromoenones and alpha-chloroenoties offers an operationally simple approach to the synthesis of both cyclic and acyclic alpha-arylenones. (c) 2006 Elsevier Ltd. All rights reserved.
• 244. Alicyclic studies. Part V. The preparation of 2-naphthyl-cycloalk-2-enones
  作者：Rivka Bar-Shai、David Ginsburg

  DOI：10.1039/jr9570001289

  日期：——