2,5-二甲基-3-苯基环戊-2-烯酮 | 36461-43-5

• 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: 2,5-二甲基-3-苯基环戊-2-烯酮
• 英文名称: 2,5-dimethyl-3-phenylcyclopent-2-enone
• 英文别名: 2,5-dimethyl-3-phenyl-cyclopent-2-enone；2,5-Dimethyl-3-phenyl-cyclopent-2-enon；2,5-Dimethyl-3-phenyl-2-cyclopenten-1-on；2,5-Dimethyl-3-phenylcyclopent-2-enon；2,5-Dimethyl-3-phenyl-2-cyclopenten-1-one；2,5-dimethyl-3-phenylcyclopent-2-en-1-one
• CAS: 36461-43-5
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: AEUZHNVVLBJJQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-dimethylamino-2,4-dimethyl-1-phenyl-pent-1-en-3-one 在 甲酸 、 磷酸 作用下， 生成 2,5-二甲基-3-苯基环戊-2-烯酮
  参考文献：
  名称：

  Jacquier et al., Bulletin de la Societe Chimique de France, 1956, p. 1653,1664

  摘要：

  DOI：

文献信息

• Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition
  作者：Aireal D. Jenkins、Ananda Herath、Minsoo Song、John Montgomery

  DOI：10.1021/ja206722t

  日期：2011.9.14

  Strategies for the reductive cycloaddition of enals or enoates with alkynes have been developed. The enal-alkyne cycloaddition directly affords cyclopentenols, whereas the enoate-alkyne cycloaddition affords the analogous cyclopentenones. The mechanism of these processes likely involves formation and protonation of a metallacyclic intermediate. The general strategy provides a straightforward entry

  已经开发了烯醛或烯酸酯与炔烃的还原环加成的策略。烯醛-炔环加成直接提供环戊烯醇，而烯酸酯-炔环加成提供类似的环戊烯酮。这些过程的机制可能涉及金属环中间体的形成和质子化。一般策略提供了从简单、稳定的 π 系统到五元环产品的直接入口。
• Reagent-free Nazarov cyclisations
  作者：Frederic Douelle、Lauren TalVisiting undergraduate from Barn、Michael F. Greaney

  DOI：10.1039/b415463k

  日期：——

  A new protocol for Nazarov cyclisation is described that involves simple heating of dienones in the absence of any external Lewis acid.

  描述了一种新的纳扎罗夫环化方案，该方案涉及在没有任何外部路易斯酸的情况下简单加热二烯酮。
• 2,2′-Biphenol/B(OH)<sub>3</sub> Catalyst System for Nazarov Cyclization
  作者：Kenji Sugimoto、Miyu Oshiro、Ryuhei Hada、Yuji Matsuya

  DOI：10.1248/cpb.c19-00399

  日期：2019.9.1

  A novel catalyst system—a combination of the readily available 2,2′-biphenol with the inexpensive, nontoxic, and eco-friendly B(OH)3—promoted the Nazarov cyclization of activated and inactivated divinyl ketones to afford the corresponding cyclopentenones up to 96% yield under, in a cis-selective manner. Compared with the conventional harsh conditions with hazardous reagents, user-friendly method was established with bench-stable and easy-to-handle reagents.

  一种新型催化剂体系——将容易获得的 2,2'-联苯酚与廉价、无毒且环保的 B(OH)3 相结合——促进了活化和失活二乙烯基酮的纳扎罗夫环化，以提供相应的环戊烯酮96％的收率，以顺式选择性方式。与传统使用危险试剂的恶劣条件相比，使用稳定且易于操作的试剂建立了用户友好的方法。
• Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl­vinyl Anion Equivalents to Access Formal Morita–Baylis–Hillman Alkylation Products
  作者：F. West、Yen-Ku Wu、Rongrong Lin

  DOI：10.1055/s-0036-1588769

  日期：2017.7

  catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita–Baylis–Hillman alkylation process.

  描述了路易斯酸催化的阳离子多米诺反应，包括顺序电环化和烯丙醇醚极性加成到所得氧烯丙基物种上。整个序列允许高度立体选择性地合成含有α-甲酰基乙烯基官能团的密集取代的环戊烷类化合物，其形式上等同于 Morita-Baylis-Hillman 烷基化过程的产物。
• 1,4‐Diketones from Cross‐Conjugated Dienones: Potassium Permanganate‐Interrupted Nazarov Reaction
  作者：Yonghoon Kwon、Devon J. Schatz、Frederick G. West

  DOI：10.1002/anie.201503696

  日期：2015.8.17

  3‐disubstituted 1,4‐diketones via a decarbonylative cleavage of the Nazarov oxyallyl intermediate, believed to be without precedent, is presented. This process allows syn substituents to be established stereospecifically on the 2‐carbon bridge connecting the ketone carbonyl carbons, and the formation of one carbon–carbon and two carbon–oxygen bonds. Two carbon–carbon bonds are cleaved in this process.

  提出了一种通过高锰酸钾中断Nazarov反应以通过Nazarov羟烯丙基中间体的脱羰基裂解产生syn-2,3-二取代的1,4-二酮的方法，据信这是没有先例的。这一过程使顺式取代基在连接酮羰基碳的2-碳桥上立体定位，并形成一个碳-碳键和两个碳-氧键。在此过程中，两个碳-碳键断裂。