1-Methyl-5--cyclohexen-(1)-on-(3) | 91142-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Methyl-5--cyclohexen-(1)-on-(3)
• 英文别名: 5-(Furan-2-yl)-3-methylcyclohex-2-en-1-one
• CAS: 91142-55-1
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: FKRJBIQMRWRFAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Methyl-5--cyclohexen-(1)-on-(3) 、 乙醇 、 氰化钾 、 alkaline earth salt of/the/ methylsulfuric acid 生成 9-[2]furyl-7-methyl-2,4-dioxo-1,3-diaza-spiro[4,5]decane-7-carbonitrile
  参考文献：
  名称：

  Conversion of Δ²-Cyclohexenones and Cyclohexanones into Spirohydantoins¹

  摘要：

  DOI：

  10.1021/ja01245a054
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 、 水 作用下， 生成 1-Methyl-5--cyclohexen-(1)-on-(3)
  参考文献：
  名称：

  Knoevenagel, Justus Liebigs Annalen der Chemie, 1898, vol. 303, p. 246

  摘要：

  DOI：

文献信息

• Organocatalyst-mediated Aldol–Robinson Cascade Reactions: A Convenient Synthesis of Substituted Cyclohex-2-enones
  作者：Li Wang、Qing-Ping Gong、Xiao-Jun Liu、Yong-Hong Li、Ping Huang、Bi-Qin Wang、Ke-Qing Zhao

  DOI：10.1246/cl.2011.138

  日期：2011.2.5

  A convenient organocatalytic process for the chemoselective synthesis of substituted cyclohex-2-enones was developed. The cascade reaction involves a remarkable Michael addition of an acyclic ketone-based enamine onto unmodified enones. The enamine-mediated aldol–Robinson cascade reactions of aromatic and aliphatic aldehydes with acetone produced substituted cyclohex-2-enones in moderate to high yields under mild reaction conditions.

  开发了一种用于取代环己-2-烯酮化学选择性合成的便捷有机催化工艺。级联反应涉及无环酮基烯胺与未改性的烯酮发生显著的迈克尔加成反应。在温和的反应条件下，烯胺介导的芳族和脂肪族醛与丙酮的醛缩-罗宾逊级联反应可产生取代环己-2-烯酮，产率中等至较高。
• The synthesis of cyclohexenone using l-proline immobilized on a silica gel catalyst by a continuous-flow approach
  作者：Cong Zhi、Jiaqing Wang、Bin Luo、Xinming Li、Xueqin Cao、Yue Pan、Hongwei Gu

  DOI：10.1039/c4ra01231c

  日期：——

  A facile and convenient method for the synthesis of cyclohexenone compounds was developed using an L-proline immobilized silica gel catalyst combined with a continuous-flow approach. Because of the mild reaction conditions, ease of catalyst recyclability, and product isolation, this reaction approach can potentially be used in a facile scale-up reaction or in industrial applications.

  使用固定化L-脯氨酸的硅胶催化剂与连续流方法相结合，开发了一种简便，方便的合成环己烯酮化合物的方法。由于反应条件温和，催化剂易于回收利用和产物分离，该反应方法可潜在地用于简便的放大反应或工业应用中。
• Mazurewitsch, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1925, vol. 56, p. 21
  作者：Mazurewitsch

  DOI：——

  日期：——
• Jyothi, Divya; Hari Prasad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 4, p. 630 - 632
  作者：Jyothi, Divya、Hari Prasad

  DOI：——

  日期：——
• Rhodium-catalyzed tandem aldol condensation–Robinson annulation between aldehydes and acetone: synthesis of 3-methylcyclohexenones
  作者：Fen Wang、Yuchen Liu、Zisong Qi、Wei Dai、Xingwei Li

  DOI：10.1016/j.tetlet.2014.09.093

  日期：2014.11

  A simple catalytic, redox-neutral access to 3-methylcyclohexenones has been developed via rhodium catalysis in the presence of an amine additive and Ag2CO3. This process utilized simple aldehydes and acetone as substrates and tolerates a variety of functional groups. Disubstituted phenols were isolated in moderate yields when Cu(OAc)(2) was employed as an oxidant. (C) 2014 Elsevier Ltd. All rights reserved.