2-甲基-3-氧代-环戊烯-1-羧酸 | 1909-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲基-3-氧代-环戊烯-1-羧酸
• 英文名称: 2-methyl-2-cyclopenten-1-one-3-carboxylic acid
• 英文别名: 2-Methyl-3-oxocyclopent-1-ene-1-carboxylic acid；2-methyl-3-oxocyclopentene-1-carboxylic acid
• CAS: 1909-79-1
• 化学式: C₇H₈O₃
• mdl: MFCD19228231
• 分子量: 140.139
• InChiKey: VQVGTOOKQICMAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  2-甲基-3-氧代-环戊烯-1-羧酸 在 palladium on activated charcoal 、 乙醇 、 奎宁 作用下， 生成 dihydrosarkomycin
  参考文献：
  名称：

  Arendaruk et al., Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1312,1317; engl. Ausg. S. 1398, 1402

  摘要：

  DOI：
• 作为产物：
  描述：

  木防己苦毒宁 在 barium dihydroxide 作用下， 生成 2-甲基-3-氧代-环戊烯-1-羧酸
  参考文献：
  名称：

  oodOPT: A semantics-based concurrency control framework for fully-replicated architecture

  摘要：

  Concurrency control has always been one of the most important issues in the design of synchronous groupware systems with fully-replicated architecture. An ideal strategy should be able to support natural and flexible human-to-computer and human-to-human interactions while maintaining the consistency of the system. This paper summarizes previous researches on this topic and points out the deficiencies of the existing results. A novel semantics-based concurrency control framework, oodOPT, is proposed. The main idea of the framework is to resolve conflicts by utilizing semantics of the operations and the accessed data objects. With this approach, complexities in concurrency control are shifted completely from application developers to the framework. Conflicts among operations on objects with different semantics and the strategies resolving these conflicts are analyzed. After describing the algorithm in full detail, the discussion ends up with a comparison with other related work and some considerations for open problems.

  DOI：

  10.1007/bf02943237

文献信息

• The Base-induced Reactions of 2-Halogeno-1,3-diketones in a Variety of Solvents
  作者：Tadahiro Wakui、Yoshio Otsuji、Eiji Imoto

  DOI：10.1246/bcsj.47.1522

  日期：1974.6

  The reactions of 2-bromo-2-methyldimedone (1), 2,2-dibromodimedone (6), 2-bromo- and 2-chloro-2-methylcyclohexane-1,3-dione (10a and 10b) and 2-acetyl-2,6-dibromocyclohexanone (14) with an equivalent of sodium acetate in a variety of solvents were studied. The constitutions and proportions of the products obtained by these reactions depended strongly on the structure of 2-halogeno-1,3-diketones and

  2-溴-2-甲基二甲酮 (1)、2,2-二溴二甲酮 (6)、2-溴-和 2-氯-2-甲基环己烷-1,3-二酮 (10a 和 10b) 和 2-乙酰基的反应研究了 -2,6-二溴环己酮 (14) 和等量的乙酸钠在各种溶剂中的作用。通过这些反应获得的产物的组成和比例很大程度上取决于 2-卤代-1,3-二酮的结构和所用的溶剂。结果根据提议的机制进行了讨论。
• Scalable and Chemoselective Synthesis of γ-Keto Esters and Acids via Pd-Catalyzed Carbonylation of Cyclic β-Chloro Enones
  作者：Justin M. Kaplan、Damian P. Hruszkewycz、Iulia I. Strambeanu、Christopher J. Nunn、Kelsey F. VanGelder、Anna L. Dunn、Derek I. Wozniak、Graham E. Dobereiner、David C. Leitch

  DOI：10.1021/acs.organomet.8b00468

  日期：2019.1.14

  The Pd-catalyzed carbonylation of cyclic β-chloro enones using simple phosphine ligands is described. Screening identified P(Me)(t-Bu)2 as the most general ligand for an array of chloro enone electrophiles. The reaction scope has been evaluated on a milligram scale across 80 examples, with excellent reactivity observed in nearly every case. Carbonylation can be achieved even in the presence of potentially

  描述了使用简单的膦配体的Pd催化的环状β-氯烯酮的羰基化反应。筛选确定P（Me）（t -Bu）2是一系列氯烯酮亲电子试剂的最一般配体。已在80个实例中以毫克为单位对反应范围进行了评估，几乎在每种情况下都观察到了出色的反应性。即使在潜在的敏感或抑制性官能团（包括碱性氮以及芳基氯化物或溴化物）的存在下，也可以实现羰基化。已经以克为单位运行了20个示例，证明了可伸缩性和实用性。使用P（Me）（t -Bu）2反应速率取决于亲核试剂和亲电试剂的同一性，在一组标准条件下，完成时间在3至> 18 h之间变化。切换到P（吨-Bu）3为吨他羰基化3- chlorocyclohex -2-烯酮在一剧烈的速率增加的甲醇的结果，使得能够与动力学与限速质量传递一致的有效的催化。3-氯环己-2-烯酮和3-氧代环己-1-烯羰基氯的化学计量氧化加成到Pd [P（t -Bu）3 ] 2和Pd（PCy 3）2上能够表征和分离几种潜在的催化中间体，包括由P（t
• C–O Bond Activation as a Strategy in Palladium-Catalyzed Cross-Coupling
  作者：David C. Leitch、Joseph Becica

  DOI：10.1055/a-1306-3228

  日期：2021.4

  The activation of strong C–O bonds in cross-coupling catalysis can open up new oxygenate-based feedstocks and building blocks for complex-molecule synthesis. Although Ni catalysis has been the major focus for cross-coupling of carboxylate-based electrophiles, we recently demonstrated that palladium catalyzes not only difficult C–O oxidative additions but also Suzuki-type cross-couplings of alkenyl

  交叉偶联催化中强C-O键的活化可以开拓新的含氧化合物原料和复杂分子合成的基础。尽管Ni催化一直是羧酸酯基亲电试剂交叉偶联的主要焦点，但我们最近证明，钯不仅可以催化难于C–O氧化的加成反应，而且还可以在温和条件下催化Suzuki型羧酸烯基酯的交叉偶联。我们建议，根据反应条件，典型的Pd（0）/（II）机理或氧化还原中性的仅Pd（II）机理均可操作。在后一种途径中，CC键的形成是通过烯烃的碳链发生，以及通过β-羧基的消除而进行的C-O裂解。1引言2机械挑战：
• Simple routes to sarkomycin
  作者：Montree Kodpinid、Tiwa Siwapinyoyos、Yodhathai Thebtaranonth

  DOI：10.1021/ja00329a038

  日期：1984.8

  Synthese de la sarkomycine soit a partir d'un spiro [cyclopentene-1:9'-ethano-9',10' anthracene] soit a partir d'un adduit itaconate-anthracene

  Synthese de la sarkomycine soit a partir d'un spiro [cyclopentene-1:9'-ethano-9',10' anthracene] soit a partir d'un adduit itaconate-anthracene
• Synthesis of<i>dl</i>-Sarkomycin (2-Methylenecyclopentanone-3-carboxylic Acid)
  作者：Katsuyuki Toki

  DOI：10.1246/bcsj.30.450

  日期：1957.5

  dl-Sarkomycin (2-methylenecyclopentanone-3-carboxylic acid) was synthesized in a four-stage process starting from ethyl cyclopentanone-3-carboxylate, prepared by Kay’s procedure. Namely, ethyl cyclopentanone-3-carboxylate was converted into ethyl 2-(dialkylaminomethyl)-cyclopentanone-3-carboxylate and thence to ethyl 2-methylenecyclopentanone-3-carboxylate. The ester was hydrolyzed to 2-methylenecyclopentanone-3-carboxylic acid with diluted hydrochloric acid. The final product was a pale yellow oil and was effective in inhibiting the growth of Ehrlich carcinoma of mice.

  dl-Sarkomycin (2-亚甲基环戊酮-3-羧酸)是由 Kay 程序制备的环戊酮-3-羧酸乙酯开始，经过四个阶段合成的。即，环戊酮-3-羧酸乙酯转化为 2-（二烷基氨基甲基）-环戊酮-3-羧酸乙酯，然后转化为 2-亚甲基环戊酮-3-羧酸乙酯。该酯用稀盐酸水解为 2-亚甲基环戊酮-3-羧酸。最终产物为淡黄色油状物，可有效抑制小鼠艾氏癌的生长。