3-Methyl-5-(4-nitro-phenyl)-cyclohex-2-enon | 62596-10-5

• 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: 3-Methyl-5-(4-nitro-phenyl)-cyclohex-2-enon
• 英文别名: 3-Methyl-5-(4-nitrophenyl)cyclohex-2-en-1-one
• CAS: 62596-10-5
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: OHAYEDWWODUBOS-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  386.2±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-5-(4-nitro-phenyl)-cyclohex-2-enon 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：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 3-Methyl-5-(4-nitro-phenyl)-cyclohex-2-enon
  参考文献：
  名称：

  Knoevenagel, Justus Liebigs Annalen der Chemie, 1898, vol. 303, p. 238

  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。
• Iodine-catalyzed tandem oxidative aromatization for the synthesis of meta-substituted alkoxybenzenes
  作者：Dahong Jiang、Xicheng Jia、Shuhua Zhang、Zhihua Zhang、Lei Li、Yanhui Qiao

  DOI：10.1016/j.tet.2021.132219

  日期：2021.7

  A rapid method for the synthesis of meta-substituted alkoxybenzenes is achieved by oxidation of cyclohexenones. This one-pot transformation is catalyzed by molecular iodine with DDQ as an oxidant in the presence of alcohols. Diverse cyclohexenones with aryl or alkyl substitutes are well tolerated to the mild oxidative conditions affording desired products in up to 92% yield. These oxidizing processes

  一种合成间位取代烷氧基苯的快速方法是通过氧化环己烯酮来实现的。这种一锅法转化是由分子碘催化的，DDQ 作为氧化剂，在醇的存在下。具有芳基或烷基取代基的各种环己烯酮对温和的氧化条件具有良好的耐受性，可提供高达 92% 产率的所需产物。这些氧化过程适用于有效合成有用的间位取代酚类产品，这些产品很难通过传统的亲电取代获得。
• A tandem Aldol condensation/dehydration co-catalyzed by acylase and N-heterocyclic compounds in organic media
  作者：Xiang Chen、Bo-Kai Liu、Hong Kang、Xian-Fu Lin

  DOI：10.1016/j.molcatb.2010.09.014

  日期：2011.1

  A tandem Aldol condensation/dehydration of aldehydes and ketones could be performed under D-aminoacylase and N-heterocyclic compounds used as co-catalyst in organic media Some control experiments have been designed to demonstrate that either acylase or N-heterocyclic compounds could not catalyze the tandem reaction The acylase showed the highest activity in the presence of imidazole and has been used to catalyze the tandem Aldol condensation/dehydration between different aldehydes and ketones This method has provided a new strategy to perform the tandem Aldol condensation/dehydration and expanded the application of biocatalysts (c) 2010 Elsevier B V All rights reserved