2,3-diethylcyclopent-2-en-1-one | 41496-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-diethylcyclopent-2-en-1-one
• 英文别名: 2,3-diethylcyclopentene-1-one；2,3-diethylcyclopent-2-enone；2,3-Diethyl-2-cyclopenten-1-one
• CAS: 41496-82-6
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: FLCXXADDHWEBSV-UHFFFAOYSA-N

物化性质

• 沸点：
  213.8±10.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2,3-diethylcyclopent-2-en-1-one 、 4-tert-butylphenyllithium 以 乙醚 为溶剂， 以97%的产率得到1,2-diethyl-3-(4-tert-butylphenyl)cyclopentadiene
  参考文献：
  名称：

  1,2,3-三取代双（环戊二烯基）二氯化锆的合成与循环伏安法

  摘要：

  的1,2,3-三取代的环戊二烯的合成3 - 10和它们相应的二茂锆二氯化物11 - 18从可商购的内部炔烃被呈现。的不同substituiertem茂锆的固态结构11 - 13和15 - 17通过X射线分析的手段检测。已经显示出咬合角度不依赖于环戊二烯基配体的取代方式。循环伏安法用于测量在五元配体上引入吸电子和供电子基团对锆中心原子的路易斯酸度的影响。

  DOI：

  10.1016/s0022-328x(02)01665-0
• 作为产物：
  描述：

  2,2-Bis-((E)-but-1-enyl)-[1,3]dioxolane 在 硫酸 、 氢溴酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 2,3-diethylcyclopent-2-en-1-one
  参考文献：
  名称：

  异常的纳扎罗夫反应。一种合成 2,3-二取代 2-环戊烯酮的新方法

  摘要：

  β,β'-二取代的交叉共轭二烯酮或相应的乙烯缩醛的酸催化反应主要产生 2,3-二取代的 2-环戊烯酮，而不是简单的 Nazarov 环化产物，即 3,4-二取代的 2-环戊烯酮。这种转变是根据电环闭环、羟基溶剂的添加、所得 2-羟基环戊酮中间体的互变异构化，然后是溶剂分解和异构化来解释的。基于该工作假设，公开了一种获得茉莉酮类化合物的新途径，该途径涉及对衍生自取代戊二酸酯的丙烯酰二甲硅烷基醚进行酸处理。

  DOI：

  10.1246/bcsj.53.169

文献信息

• CuCl-catalyzed reaction of zirconacyclopentenes with oxalyl chloride: a new pathway for the preparation of cyclopentenones
  作者：Chao Chen、Yundong Liu、Chanjuan Xi

  DOI：10.1016/j.tetlet.2009.07.065

  日期：2009.9

  Zirconacyclopentenes, which are easily prepared from alkynes and EtMgBr (or ethylene) and Cp2ZrCl2, reacted with oxalyl chloride in the presence of catalytic amount of CuCl to give cyclopentenones in high yields. The reaction was performed conveniently in one pot from alkynes, EtMgBr, oxalyl chloride, and Cp2ZrCl2.

  容易从炔烃和EtMgBr（或乙烯）和Cp 2 ZrCl 2制备的锆碳环戊烯与草酰氯在催化量的CuCl存在下反应，以高收率得到环戊烯。该反应方便地在一锅中从炔烃，EtMgBr，草酰氯和Cp 2 ZrCl 2进行。
• Modulators of ATP-binding cassette transporters
  申请人：Ruah S. Hadida Sara

  公开号：US20080044355A1

  公开（公告）日：2008-02-21

  Compounds of the present invention and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

  本发明中的化合物及其药学上可接受的组合物，可用作ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节因子（“CFTR”）。本发明还涉及使用本发明中的化合物治疗ABC转运蛋白介导的疾病的方法。
• Polymer-Mediated Reactions. A Nazarov-Like Cyclization
  作者：Michael Smith、Christopher Pavlik、Martha Morton、Michael Invernale、Ian Berghorn、Gregory Sotzing

  DOI：10.1055/s-0030-1261194

  日期：2011.9

  The polymer PEDOT+ mediates a Nazarov-like cyclization of dienones, in an heterogeneous system and in hydrocarbon solvents. The polymer-mediated reactions show clear differences in product formation when compared to the same reaction with tosic acid, or when compared to reports in the literature. Comparable or improved yields are observed, as well as the ability to give a Nazarov product in cases where treatment with acid fails to give cyclization, or leads to an undesirable rearrangement. In addition, the ability to recycle the polymer makes this a potentially useful protocol for an important organic chemical reaction.
• Convenient preparative method of α,β-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO
  作者：Tamotsu Takahashi、Zhenfeng Xi、Yasushi Nishihara、Shouquan Huo、Kayoko Kasai、Koichiro Aoyagi、Victor Denisov、Ei-ichi Negishi

  DOI：10.1016/s0040-4020(97)00612-1

  日期：1997.7

  Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addition of an internal alkyne and subsequent treatment with CO/I-2 gave alpha,beta-disubstituted cyclopentenone in good to high yields. When a conjugated enyne was used as an alkyne component, alpha-alkenyl cyclopentenone was selectively formed in 80-89% yields. In the case of 4,6-decadiyne, alpha-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynytbenzene afforded alpha alpha'-bridged cyclopentenone compounds in good yields. (C) 1997 Elsevier Science Ltd.
• 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.