2,3-dimethyl-4-phenylcyclopent-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-dimethyl-4-phenylcyclopent-2-en-1-one
• 英文别名: 2,3-dimethyl-4-phenylcyclopent-2-enone；2,3-Dimethyl-4-phenyl-2-cyclopenten-1-one
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: PWHCIZYZEVSMAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：

  (E)-2,3-dimethyl-1-phenyl-4-(phenylthio)penta-1,4-dien-3-ol 在 bismuth(lll) trifluoromethanesulfonate 、 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以78%的产率得到2,3-dimethyl-4-phenylcyclopent-2-en-1-one
  参考文献：
  名称：

  调整功能化二烯丙基醇的反应性：Brønsted与路易斯酸催化

  摘要：

  公开了在酸性介质中双官能的含烯醇硫醚的二烯丙基醇的化学发散反应性，突出了强路易斯酸和温和布朗斯台德酸催化之间的区别。在三氟甲磺酸铋（III）的存在下，烯丙醇的活化在Nazarov型电环化中提供了不同取代的环戊烯酮，而对甲苯磺酸对硫烯醇醚的活化则为α-亚磺酰基化的β，γ-不饱和酮提供了入口。两种方法都表示使用便宜且无毒的催化系统，可以在温和条件下轻松获得相应的产品。

  DOI：

  10.1002/chem.201702601

文献信息

• Brønsted Acid-Mediated Nazarov Cyclization of Vinylallenes
  作者：Yen-Ku Wu、F. G. West

  DOI：10.1021/jo101112t

  日期：2010.8.6

  Treatment of siloxy enynes with base leads to the corresponding vinylsiloxyallenes which undergo Nazarov cyclization in the presence of trifluoroacetic acid to provide the cyclized product as a mixture of regioisomers in moderate to good overall yield.

  用碱处理甲硅烷氧基烯炔会导致相应的乙烯基甲硅烷氧基丙二烯在三氟乙酸的存在下经历纳扎罗夫环化反应，从而以中等至良好的总收率提供呈区域异构体混合物形式的环化产物。
• Rearrangement of 1-(1-Alkynyl)cyclopropanols to 2-Cyclopentenones via Their Hexacarbonyldicobalt Complexes. A New Use of Alkyne−Co₂(CO)₆ Complexes in Organic Synthesis
  作者：Nobuharu Iwasawa、Takeshi Matsuo、Mari Iwamoto、Taketo Ikeno

  DOI：10.1021/ja9734004

  日期：1998.4.1

  protective group of the substrates. This rearrangement was successfully applied to cyclopentenone annulation reactions onto cycloalkenes. An efficient synthesis of alkynyl-substituted bicyclo[n.1.0]alkanol derivatives from the corresponding cycloalkenes according to Danheiser's protocol was developed, and bicyclic cyclopentenones were obtained in moderate to good yield by applying to these the cobalt-mediated

  1-(1-炔基) 环丙醇向 2-环戊烯-1-酮的新重排是在其炔基部分与八羰基二钴 (Co2(CO8)) 络合后进行的。1-(1-炔基) 环丙醇在其炔烃末端具有广泛的取代基，以良好的产率重排为相应的 3-取代的 2-环戊烯-1-酮。In case of the reactions of 1-alkynylcyclopropanols with an alkyl substituent on the cyclopropane ring, either 4-substituted or 5-substituted 2-cyclopenten-1-ones could be selectively obtained by appropriate choice of stereochemistry and protective group of the substrates. 这种重排成功地应用于环戊烯酮环化成环烯烃的反应。根据
• Nickel-Catalyzed Formation of Cyclopentenone Derivatives via the Unique Cycloaddition of α,β-Unsaturated Phenyl Esters with Alkynes
  作者：Masato Ohashi、Tomoaki Taniguchi、Sensuke Ogoshi

  DOI：10.1021/ja2059999

  日期：2011.9.28

  Oxygen-containing organic compounds, such as ethers, carboxylates, and carbamates, have recently received increasing attention because of their newly discovered applications as electrophiles in cross-coupling reactions via transition metal-catalyzed C-O bond activation. However, no cycloaddition reaction involving their C-O bond activation has been demonstrated thus far. The present study developed a Ni(O)-catalyzed unique [3+2] cycloaddition reaction of alpha,beta-unsaturated phenyl esters with alkynes in (PrOH)-Pr-i to yield cydopentenone derivatives.
• Formation of halogenated cyclopent-2-enone derivatives by interrupted Nazarov cyclizations
  作者：Vanessa M. Marx、T. Stanley Cameron、D. Jean Burnell

  DOI：10.1016/j.tetlet.2009.10.052

  日期：2009.12

  Allenyl vinyl ketones were exposed to titanium and indium halides in order to carry out Nazarov cyclizations. Whereas Til(4) and InX3 (X = Cl, Br, and I) led to cyclopentenones in which a halogen was trapped highly regioselectively, the reactions mediated by TiBr4 gave mixtures of brominated isomers. When the allenyl vinyl ketones were treated first with Br-2 and then with TiBr4, doubly brominated cyclopentenones resulted, and treatment with I-2 followed by TFA gave cyclopentenones bearing both hydroxyl and iodo groups. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] NIMBOLIDE ANALOGS AND METHODS OF USE THEREOF<br/>[FR] ANALOGUES DE NIMBOLIDE ET LEURS MÉTHODES D'UTILISATION
  申请人：[en]THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM

  公开号：WO2022150667A1

  公开（公告）日：2022-07-14

  Disclosed herein are compounds of the formula (I) or (II) wherein the variables are defined herein. Also provided are methods of manufacturing and pharmaceutical compositions thereof. In some aspects, the compounds and compositions provided herein may be used as PARP1 inhibitors. In some aspects, the present disclosure provides methods wherein the compounds and compositions described herein are used for the treatment of diseases and disorders, such as cancer.