5-(4-chlorophenyl)-3-methylcyclohex-2-enone | 54795-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-chlorophenyl)-3-methylcyclohex-2-enone
• 英文别名: 5-(4-chloro-phenyl)-3-methyl-cyclohex-2-enone；5-(4-Chlor-phenyl)-3-methyl-cyclohex-2-enon；5-(4-Chlorophenyl)-3-methylcyclohex-2-en-1-one
• CAS: 54795-01-6
• 化学式: C₁₃H₁₃ClO
• 分子量: 220.699
• InChiKey: UEOBCBRBHZSQRB-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  331.7±42.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  5-(4-chlorophenyl)-3-methylcyclohex-2-enone 在 乙醇 、 盐酸羟胺 、 sodium carbonate 作用下， 生成 5-(4-chloro-phenyl)-3-hydroxyamino-3-methyl-cyclohexanone oxime
  参考文献：
  名称：

  Knoevenagel, Justus Liebigs Annalen der Chemie, 1898, vol. 303, p. 255

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-Chloro-phenyl)-4-hydroxy-4-methyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester 在 氢氧化钾 作用下， 生成 5-(4-chlorophenyl)-3-methylcyclohex-2-enone
  参考文献：
  名称：

  Knoevenagel, Justus Liebigs Annalen der Chemie, 1898, vol. 303, p. 255

  摘要：

  DOI：

文献信息

• d-Aminoacylase-initiated cascade Aldol condensation/Robinson annulation for synthesis of substituted cyclohex-2-enones from simple aldehydes and acetone
  作者：Ziwei Xiang、Yiru Liang、Xiang Chen、Qi Wu、Xianfu Lin

  DOI：10.1007/s00726-014-1747-6

  日期：2014.8

  As an important building block, developing efficient and green synthesis strategy of cyclohex-2-enones is of great importance. In this present work, a general approach to the mild synthesis of substituted cyclohex-2-enones derivatives starting fro m simple aldehydes and acetone have been achieved via d-aminoacylase-initiated Aldol condensation/Robinson annulation cascade reaction using imidazole as

  作为重要的组成部分，开发高效且绿色的环己-2-烯酮合成策略非常重要。在本工作中，已通过使用咪唑作为有机添加剂的d-氨酰基酶引发的Aldol缩合/鲁宾逊环化级联反应，实现了由简单的醛和丙酮轻度合成取代的环己-2-烯酮衍生物的一般方法。媒体。系统地研究了反应条件对溶剂，酶浓度，添加剂类型，酶与添加剂的摩尔比，底物范围等的影响。此外，设计了一些实验来探索d的催化作用。-氨基酰化酶和咪唑在多步级联过程中，并提出了一种可能的机理。
• <i>L</i>-Lysine/imidazole-catalyzed Multicomponent Cascade Reaction: Facile Synthesis of C5-substituted 3-Methylcyclohex-2-enones
  作者：Ziwei Xiang、Zhiqiang Liu、Yiru Liang、Qi Wu、Xianfu Lin

  DOI：10.1002/cjoc.201300367

  日期：2013.8

  A facile and simple route for the direct preparation of substituted 3‐methylcyclohex‐2‐enone via Aldol‐Robinson cascade reaction of aldehydes and acetones catalyzed by the new catalytic system of L‐lysine/imidazole in n‐heptane with 0.5% water was reported. A variety of substrates can participate in the process efficiently. The merits of this method included inexpensive and easily available starting

  一种用于直接制备取代的3-甲基环己-2-烯酮的容易和简单的路线经由通过的新催化体系催化的醛和丙酮的醛醇-罗宾逊级联反应大号赖氨酸/咪唑ñ用0.5％的水-庚烷报道。多种基材可以有效地参与该过程。该方法的优点包括廉价且易于获得的起始原料和催化剂，产物的高收率和直接的后处理。
• 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。