2-methyl-3-phenylinden-1-one | 13304-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-methyl-3-phenylinden-1-one
• 英文别名: 2-methyl-3-phenyl-1H-inden-1-one；2-methyl-3-phenylindenone；2-Methyl-3-phenyl-inden-1-on；2-Methyl-3-phenyl-indenon
• CAS: 13304-52-4
• 化学式: C₁₆H₁₂O
• 分子量: 220.271
• InChiKey: UDWBAQZJOXYFCY-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  363.4±42.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 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

安全信息

• 海关编码：
  2914399090

反应信息

• 作为反应物：
  描述：

  2-methyl-3-phenylinden-1-one 在 四氯化碳 、 氢氧化钾 、 氯 作用下， 生成 2-((Z?)-2-chloro-1-phenyl-propenyl)-benzoic acid
  参考文献：
  名称：

  de Fazi; Berti, Gazzetta Chimica Italiana, 1950, vol. 80, p. 87,90

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘苄醇 在 palladium diacetate 四丁基氯化铵 、 sodium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 25.5h， 生成 2-methyl-3-phenylinden-1-one
  参考文献：
  名称：

  Synthesis of indenones via palladium-catalyzed annulation of internal alkynes

  摘要：

  A number of 2,3-disubstituted 1-indenones have been prepared in fair to good yields by treating o-iodo- or o-bromobenzaldehyde with various internal alkynes in the presence of a palladium catalyst. Synthetically, the methodology provides an especially convenient route to stable hindered indenones containing aryl, silyl, and tert-alkyl groups. The reaction is believed to proceed through a palladium-(IV) intermediate, and the regiochemistry of the reaction is controlled sterically.

  DOI：

  10.1021/jo00069a017

文献信息

• Carbopalladation of Nitriles:  Synthesis of 2,3-Diarylindenones and Polycyclic Aromatic Ketones by the Pd-Catalyzed Annulation of Alkynes and Bicyclic Alkenes by 2-Iodoarenenitriles
  作者：Alexandre A. Pletnev、Qingping Tian、Richard C. Larock

  DOI：10.1021/jo026178g

  日期：2002.12.1

  represents one of the first examples of the addition of an organopalladium moiety to the carbon-nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.

  2-碘苄腈，其衍生物和各种杂环类似物在二芳基乙炔或双环烯烃上进行钯（0）催化的环化反应，从而以非常好的至极好的收率得到2,3-二芳基萘和多环芳族酮。该反应代表将有机钯部分加成到腈的碳-氮三键上的第一个例子。该反应与许多官能团相容。提出了反应机理以及考虑取代基对腈芳环电子效应的模型。
• Ethics and Foreign Policy: The Antinomies of New Labour's ‘Third Way’ in Sub-Saharan Africa
  作者：Rita Abrahamsen、Paul Williams

  DOI：10.1111/1467-9248.00312

  日期：2001.6

  This article explores how New Labour has attempted to implement its ideas about a ‘third way’ foreign policy in sub-Saharan Africa. Through an examination of British foreign policy practices, we explore whether New Labour has succeeded in finding a ‘third way’ between traditional views of socialism and capitalism in Africa. In particular, the article focuses on New Labour's attempts to build peace, prosperity and democracy on the African continent. We conclude that although New Labour's claims to add an ‘ethical dimension’ to foreign policy have succeeded in giving Britain a higher profile in the international arena, the implementation of such a policy is intrinsically difficult. These difficulties in turn arise from the antinomies embodied in New Labour's policy, or more specifically from the tension between the liberal internationalism of the third way and traditional concerns for the national interest, as well as the contradictions inherent in a commitment to both political and economic liberalism.

  这篇文章探讨了新工党如何试图在撒哈拉以南非洲实施其关于“第三条道路”外交政策的想法。通过对英国外交政策实践的审查，我们探讨新工党是否成功地在非洲传统社会主义和资本主义观念之间找到了一种“第三条道路”。特别是，文章关注新工党在非洲大陆上建立和平、繁荣和民主的努力。我们得出结论，尽管新工党声称在外交政策中增加了“道德维度”成功地使英国在国际舞台上更加引人注目，但这种政策的实施本质上是困难的。这些困难反过来源于新工党政策所体现的矛盾，更具体地说，源于第三条道路的自由国际主义与对国家利益的传统关注之间的紧张关系，以及对政治和经济自由主义的承诺中固有的矛盾。
• Rhodium/Copper-Catalyzed Annulation of Benzimides with Internal Alkynes: Indenone Synthesis through Sequential CH and CN Cleavage
  作者：Bi-Jie Li、Hao-Yuan Wang、Qi-Lei Zhu、Zhang-Jie Shi

  DOI：10.1002/anie.201200271

  日期：2012.4.16

  Doubled up: A rhodium(III)/copper(II) system co‐catalyzes the annulation of benzimides with internal alkynes for the synthesis of indenones (see scheme; Cp*=C5Me5). The reaction involves an uncommon nucleophilic addition of a transition‐metal–carbon bond to an imide moiety. This novel reaction provides a facile route to synthesize indenones from readily available benzimides and internal alkynes.

  加倍：铑（III）/铜（II）系统共催化苯并酰亚胺与内部炔烃的环化反应，以合成茚满（参见方案； Cp * = C 5 Me 5）。该反应涉及到过渡金属-碳键向酰亚胺部分的不常见亲核加成。该新颖的反应提供了从容易获得的苯甲酰亚胺和内部炔烃合成茚满的简便途径。
• Mechanochemical Solvent-Free Synthesis of Indenones from Aromatic Carboxylic Acids and Alkynes
  作者：Liang Li、Guan-Wu Wang

  DOI：10.1021/acs.joc.1c01472

  日期：2021.10.15

  solvent-free synthesis of indenones from aromatic carboxylic acids and alkynes was achieved through triflic anhydride (Tf2O)-induced cyclization reaction. A variety of indenones including a bioactive PPARγ agonist were obtained in up to 90% yield at room temperature. The present protocol has the advantages of mild reaction conditions, high reaction efficiency, and feasibility of scalable synthesis, providing

  通过三氟甲磺酸酐 (Tf 2 O) 诱导的环化反应，实现了从芳香羧酸和炔烃无溶剂合成茚酮的机械化学溶剂。在室温下以高达 90% 的产率获得了包括生物活性 PPARγ 激动剂在内的各种茚酮。本协议具有反应条件温和、反应效率高、可扩展合成的可行性等优点，为各种茚酮提供了一条简便、可持续的途径。
• Synthesis of Chiral 3-Substituted Indanones via an Enantioselective Reductive-Heck Reaction
  作者：Ana Minatti、Xiaolai Zheng、Stephen L. Buchwald

  DOI：10.1021/jo701741y

  日期：2007.11.1

  An efficient intramolecular palladium-catalyzed, asymmetric reductive-Heck reaction has been developed, which allowed for the synthesis of either enantiomerically enriched 3-substituted indanones or α-exo-methylene indanones depending on the base used.

  已经开发了有效的分子内钯催化的不对称还原-Heck反应，其取决于所用的碱，可以合成对映体富集的3-取代的茚满酮或α-外-亚甲基茚满酮。