1-Methyl-5-thienyl-(2)-cyclohexen-(1)-on-(3) | 92324-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Methyl-5-thienyl-(2)-cyclohexen-(1)-on-(3)
• 英文别名: 5--1-methyl-cyclohexen-(1)-on；3-methyl-5-(thiophen-2-yl)cyclohex-2-enone；3-Methyl-5-thiophen-2-ylcyclohex-2-en-1-one
• CAS: 92324-27-1
• 化学式: C₁₁H₁₂OS
• 分子量: 192.282
• InChiKey: RHGLFZPFPCEBPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Methyl-5-thienyl-(2)-cyclohexen-(1)-on-(3) 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  铜催化环己烯酮肟酯合成取代伯芳胺

  摘要：

  开发了一种使用环己烯酮肟酯铜催化合成具有间位取代基的伯芳胺的新方案。机理研究表明该反应通过亚胺自由基中间体的分子间 1,5-H 氢原子转移进行。这种方法具有高效率、易于使用的催化剂系统和广泛的官能团耐受性的特点。

  DOI：

  10.1021/acs.orglett.3c03501
• 作为产物：
  描述：

  2-噻吩甲醛 、 丙酮 在 四氢吡咯 、 丙酸 作用下， 反应 24.0h， 以91%的产率得到1-Methyl-5-thienyl-(2)-cyclohexen-(1)-on-(3)
  参考文献：
  名称：

  Organocatalyst-mediated Aldol–Robinson Cascade Reactions: A Convenient Synthesis of Substituted Cyclohex-2-enones

  摘要：

  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。

  DOI：

  10.1246/cl.2011.138

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。
• Controlling Cyclic Dienamine Reactivity in Radical tert‐Alkylation for Molecular Diversity to Synthesize Multicyclic Compounds Possessing a Quaternary Carbon
  作者：Shinjiro Kusano、Takashi Nishikata

  DOI：10.1002/chem.202304215

  日期：2024.3.20

  Selective formation of the desired dienamines from β-methylcyclohexenone and their reaction with tertiary alkyl radicals generated from α-bromoesters led to the synthesis of γ-oxoalkyl substituted cyclohexenone derivatives (OAC) with a quaternary carbon have been successfully synthesized. This OAC can be used as a common synthetic intermediate for fused [5,6] rings and spirocycles.

  由β-甲基环己烯酮选择性形成所需的二烯胺，并与α-溴酯产生的叔烷基自由基反应，成功合成了具有季碳的γ-氧代烷基取代的环己烯酮衍生物（OAC）。该OAC可用作稠合[5,6]环和螺环的常见合成中间体。
• 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.
• Copper-Catalyzed Synthesis of Substituted Primary Arylamines from Cyclohexenone Oxime Esters
  作者：Yong-Jie Kuang、Yan Yu、Min Zhou、Yu-Cheng Yin、Tian Cai、Qun-Li Luo

  DOI：10.1021/acs.orglett.3c03501

  日期：2023.12.8

  A novel protocol has been developed for the Cu-catalyzed synthesis of primary arylamines with meta-substituents using cyclohexenone oxime esters. Mechanistic insights suggest that the reaction proceeds via an intermolecular 1,5-H hydrogen atom transfer of an imine radical intermediate. This approach features high efficiency, a readily available catalyst system, and broad functional group tolerance

  开发了一种使用环己烯酮肟酯铜催化合成具有间位取代基的伯芳胺的新方案。机理研究表明该反应通过亚胺自由基中间体的分子间 1,5-H 氢原子转移进行。这种方法具有高效率、易于使用的催化剂系统和广泛的官能团耐受性的特点。