2-carbonylcyclopentanone | 3491-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-carbonylcyclopentanone
• 英文别名: carbonylcyclopentanone；Cyclopentanone, 2-carbonyl-
• CAS: 3491-01-8
• 化学式: C₆H₆O₂
• 分子量: 110.112
• InChiKey: OMVPGBLGIPSDKE-UHFFFAOYSA-N

物化性质

• 沸点：
  162.2±20.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  2-carbonylcyclopentanone 在 sodium bromide 作用下， 以 水 为溶剂， 生成 2-Carboxycyclopenten-1-olate
  参考文献：
  名称：

  水溶液中的 2-氧代环戊烷甲酸酮-烯醇系统：通过酰基乙烯酮的水合生成烯醇

  摘要：

  2-重氮环己烷-1,3-二酮在水溶液中的闪光光解产生2-酮环戊基烯酮，其水合为2-氧代环戊烷羧酸的烯醇，然后烯醇异构化为酸的酮形式。这种乙烯酮被证明是一种非常活泼的物质，其未催化的水合速率常数为 k = 1.4 × 106 s-1，氢氧根离子催化的速率常数为 7.5 × 107 M-1 s-1；没有发现水合的酸催化作用。烯醇的酮化是一个较慢的过程，速率常数在毫秒到秒范围内。该反应显示出复杂的速率曲线，可以解释为决定质子转移到连续电离形式的烯醇在连续碱性溶液中的 β-碳原子的速率。在浓酸溶液中，烯醇的羧酸基团也经历了其羰基的平衡质子化，pKSH = -3.86。烯醇的羧酸基团的酸度常数，pQa,E = 4.16，羟基...

  DOI：

  10.1021/ja9704390
• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 200.0 ℃ 、0.11 Pa 条件下， 生成 2-carbonylcyclopentanone
  参考文献：
  名称：

  Direct observation of .alpha.-oxo ketenes formed from 1,3-dioxin-4-ones and the enols of .beta.-keto esters

  摘要：

  The enol forms of beta-keto esters thermolyze to alcohols and alpha-oxo ketenes, which are characterized by low-temperature IR spectroscopy and on warming regenerate the beta-hydroxy-alpha,beta-unsaturated esters. The matrix isolated s-Z and s-E forms of alpha-oxo ketenes are characterized and photochemically converted into other conformers or sites. Matrix photolysis of 2,2,6-trimethyl-1,3-dioxin-4-one gives the s-Z acetylketene initially. Alpha-Oxo ketenes polymerize in the cold and dimerize only at elevated temperatures.

  DOI：

  10.1021/jo00007a008

文献信息

• NOVEL ENT-KAURENE DITERPENE COMPOUND AND ITS DERIVATIVES, THEIR PREPARATION AND THEIR USE
  申请人：Liu Hongmin

  公开号：US20100228014A1

  公开（公告）日：2010-09-09

  Novel ent-kaurene diterpene compound and its derivatives, their preparation methods and their use. ent-Kaurene diterpene in the present invention could be used as desired intermediates for preparing asymmetric organic compounds and medicaments, and could be used as antitumor agent, anti-inflammatory agent and immune agent etc. The said ent-kaurene diterpene compound could be condensed with hydroxyl compounds to obtain various acetal derivatives, could be reacted with amine compounds to obtain various amino derivatives, and could be reacted with acyl halide or acid anhydride to obtain various acyl derivatives.

  新颖的ent-kaurene二萜化合物及其衍生物，其制备方法及其用途。本发明中的ent-kaurene二萜化合物可用作制备不对称有机化合物和药物的所需中间体，并可用作抗肿瘤剂、抗炎剂和免疫剂等。所述的ent-kaurene二萜化合物可与羟基化合物缩合以获得各种缩醛衍生物，可与胺类化合物反应以获得各种氨基衍生物，可与酰卤或酸酐反应以获得各种酰衍生物。
• Periselectivity in the aza-Diels–Alder Cycloaddition between α-Oxoketenes and <i>N</i>-(5-Pyrazolyl)imines: A Combined Experimental and Theoretical Study
  作者：Juan-Carlos Castillo、Brian Castro Agudelo、Jaime Gálvez、Yannick Carissan、Jean Rodriguez、Yoann Coquerel

  DOI：10.1021/acs.joc.0c00767

  日期：2020.6.5

  N-(5-pyrazolyl)imines as the 4π partners at their 2-azadiene moiety. In contrast, other cyclic and acyclic α-oxoketenes lead preferentially to 1,3-oxazin-4-ones, which now involves the α-oxoketenes as the 4π partners at their 1-oxadiene moiety and the N-(5-pyrazolyl)imines as the 2π partners at their C═N double bond. A computational modeling study using DFT methods allowed rationalizing this change of periselectivity:

  α-氧杂环丁烯之间的热6πaza-Diels-Alder环加成反应原位是由热诱导的2-重氮1,3-二酮的Wolff重排和N-（5-吡唑基）亚胺作为典型的富电子2-氮杂二烯产生两种不同的产物，基本上是所涉及的α-氧杂环丁烯的性质的函数。例如，环状五元α-氧杂环丁烯优先导致螺氢吡啶-4-酮，其中α-氧杂环丁烯在其C═C双键处为2π配偶体，而N-（5-吡唑基）亚胺为4π。在它们的2-氮杂二烯部分上形成伙伴。相比之下，其他环状和无环的α-氧杂环丁烯优先导致1,3-oxazin-4-ones，现在，α-氧杂环丁烯在其1 -oxadiene部分和4π伙伴中涉及4π伙伴。N-（5-吡唑基）亚胺在其C═N双键处为2π伙伴。使用DFT方法进行的计算模型研究可以合理化这种选择性的变化：螺吡喃并吡啶-4-酮的形成受热力学控制，而1,3-恶嗪-4-酮的形成受动力学控制，而在热力学上略有不利。五元环系列。还详细研究了α-氧杂环丁烯的竞争性环二聚化。
• [EN] REAGENT FOR TARGETING DEGRADATION OF BCR-ABL PROTEIN AND USE IN PREPARATION OF PHILADELPHIA CHROMOSOME-POSITIVE TUMOR-CURING MEDICINE<br/>[FR] RÉACTIF POUR CIBLER LA DÉGRADATION DE LA PROTÉINE BCR-ABL ET UTILISATION DANS LA PRÉPARATION D'UN MÉDICAMENT DESTINÉ À GUÉRIR UNE TUMEUR POSITIVE POUR LE CHROMOSOME PHILADELPHIE
  申请人：UNIV SUN YAT SEN

  公开号：WO2014048109A1

  公开（公告）日：2014-04-03

  一种靶向降解Bcr-Abl蛋白的试剂及其应用。该试剂的主要成分为冬凌草甲素或以冬凌草甲素为先导化合物的具有环外亚甲基环戊酮结构的四环二萜类化合物。所述试剂可用于靶向降解Bcr-Abl和c-Abl蛋白，并治疗费城染色体阳性肿瘤。
• Direct observation of .alpha.-oxo ketenes from the photolysis of .alpha.-diazo .beta.-diketones
  作者：Regis Leung-Toung、Curt Wentrup

  DOI：10.1021/jo00044a019

  日期：1992.8

  Monitoring by IR spectroscopy of the broad-band irradiation of the symmetrically substituted 2-diazo-cyclohexane-1,3-dione (I 1), 3-diazopentane-2,4-dione (19), and 4-diazo-2,2,6,6-tetramethylheptane-3,5-dione (24) in Ar matrices at 12 K showed the formation of 2-carbonylcyclopentanone (s-Z-12), acetyl(methyl)ketene (s-E-20), and tert-butyl(pivaloyl)ketene (s-E-25), respectively, in less than 10 min. On increasing the photolysis time to >3 h, the alpha-oxo ketenes 12,20, and 25 decarbonylated to the corresponding oxocarbenes which underwent Wolff rearrangement to carbonylcyclobutane (15), dimethylketene (23), and di-tert-butylketene (28), respectively. The reaction of 2-carbonylcyclopentanone (12) with CH3OH was monitored by IR spectroscopy. Thus, it was found that the reaction started at ca. 100 K and was essentially complete at 140 K, involving the initial formation of the enol form (9) of methyl 2-oxocyclopentanecarboxylate.
• FREIERMUTH, BEAT;WENTRUP, CURT, J. ORG. CHEM., 56,(1991) N, C. 2286-2289
  作者：FREIERMUTH, BEAT、WENTRUP, CURT

  DOI：——

  日期：——