3-(3-Chloro-phenylamino)-5,5-dimethyl-cyclohex-2-enone | 50685-29-5

• 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-(3-Chloro-phenylamino)-5,5-dimethyl-cyclohex-2-enone
• 英文别名: 3-(3'-Chloranilino)-5.5-dimethylcyclohex-2-en-1-on；3-m-Chloranilino-5,5-dimethyl-2-cyclohexenon；3-(3'-Chloranilin)-5.5-dimethylcyclohex-2-en-1-on；3-[(3-Chlorophenyl)amino]-5,5-dimethylcyclohex-2-en-1-one；3-(3-chloroanilino)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 50685-29-5
• 化学式: C₁₄H₁₆ClNO
• mdl: MFCD00156401
• 分子量: 249.74
• InChiKey: CEQJQTUWWPLELV-UHFFFAOYSA-N

物化性质

• 沸点：
  357.3±42.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-(3-Chloro-phenylamino)-5,5-dimethyl-cyclohex-2-enone 在 sodium hydride 、 sodium amide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1,2,3,9-tetrahydro-4,4,9-trimethyl-2H-carbazol-2-one
  参考文献：
  名称：

  Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles

  摘要：

  The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.

  DOI：

  10.1016/s0040-4020(01)89304-2
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 生成 3-(3-Chloro-phenylamino)-5,5-dimethyl-cyclohex-2-enone
  参考文献：
  名称：

  Sawjalow S. I., Dorofeewa O. F., Rumjanchewa E. E., Sawosin A. G., Khim.-farmach. zh, 29 (1995) N 2, S 58, 65

  摘要：

  DOI：

文献信息

• Efficient Synthesis of Functionalized Dihydro-1<i>H</i>-indol-4(5<i>H</i>)-ones via One-Pot Three-Component Reaction under Catalyst-Free Conditions
  作者：Hui-Yan Wang、Da-Qing Shi

  DOI：10.1021/co4000198

  日期：2013.5.13

  A facile and efficient one-pot procedure for the preparation of functionalized dihydro-1H-indol-4(5H)-ones by a catalyst-free, three-component reaction of 1,3-dicarbonyl compounds, arylglyoxal monohydrate and enaminones under mild conditions in excellent yield is reported. This synthesis was confirmed to follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional purifications

  一种简便有效的一锅法，用于在温和条件下通过无催化剂的1,3-二羰基化合物，芳基乙二醛一水合物和烯胺酮的三组分反应制备官能化的二氢-1H-吲哚-4（5H）-酮据报道，其收率极高。证实该合成遵循组辅助纯化（GAP）化学过程，该过程可避免传统的纯化，色谱法和重结晶。
• Facile one-pot three-component synthesis of diverse 2,3-disubstituted isoindolin-1-ones using ZrO₂ nanoparticles as a reusable dual acid–base solid support under solvent-free conditions
  作者：Kamalesh Debnath、Sayan Mukherjee、Chandan Bodhak、Animesh Pramanik

  DOI：10.1039/c6ra00870d

  日期：——

  A facile one-pot three-component protocol for the synthesis of a series of multi-functionalized 2,3-disubstituted isoindolin-1-ones has been developed using ZrO2 nanoparticles as a dual acid–base solid support under solvent-free conditions. The surface of the ZrO2 nanoparticles, which is embedded with active hydroxyl groups, oxyanions and Zr4+ ions, efficiently catalyses the condensation of 2-carboxybenzaldehyde

  使用ZrO 2纳米颗粒作为无溶剂条件下的双酸碱固相载体，已经开发了一种简便的一锅三组分规程，用于合成一系列多官能化的2,3-二取代异吲哚啉-1-酮。ZrO 2纳米颗粒的表面嵌入了活性羟基，氧阴离子和Zr 4+离子，可有效催化2-羧基苯甲醛，脂肪族胺与亲核试剂的缩合（烯胺/ 6-氨基1,3-二甲基尿嘧啶/ 1 ，3-环己二酮/吲哚）产生2，3-二取代的异吲哚啉-1-酮。操作简单，减少反应时间和温度，消除溶剂，产品产率高，基材范围更广，ZrO 2的利用 作为固体载体的纳米颗粒及其在重复应用后几乎没有减弱的催化活性是本方法的关键特征。
• Iodine(III)-Promoted Ring Contractive Cyanation of Exocyclic β-Enaminones for the Synthesis of Cyanocyclopentanones
  作者：Dhananjay Bhattacherjee、Vandna Thakur、Saurabh Sharma、Sandeep Kumar、Richa Bharti、C. Bal Reddy、Pralay Das

  DOI：10.1002/adsc.201601208

  日期：2017.7.3

  A highly efficient hypervalent iodine‐promoted regiocontrolled ring contractive cyanation (RCC) reaction of exocyclic β‐enaminones for the synthesis of cyanocyclopentanone (CCP) was demonstrated at ambient temperature with a wide substrate scope. The methodology offers a facile technique to construct an amino carbonitrile‐containing quaternary stereocenter at the α‐position of cyclopentanone in good

  在环境温度下，广泛的底物范围证明了环外β-烯胺酮的高效高价碘促进的区域控制的环收缩氰化（RCC）反应，用于氰基环戊酮（CCP）的合成。该方法提供了一种简便的技术，可在环戊酮的α位上以高收率构建含氨基甲腈的季立体中心。严格研究了底物添加的顺序，该顺序可以促进反应遵循不同的途径（自由基/非自由基）以提供相同的最终产物。
• Oligosaccharide Assisted Approach: An Efficient and Facile Access to Isochromeno [4,3-b] Indoles Derivatives in the Presence of Beta Cyclodextrin
  作者：Akhilesh Kumar、Pragati Rai、Vijay B. Yadav、I. R. Siddiqui

  DOI：10.1007/s10562-018-2592-0

  日期：2019.1

  A completely eco-friendly and straightforward protocol for the biologically important isochromeno[4,3-b]indoles derivatives has been developed employing beta cyclodextrin in aqueous medium. This documented strategy includes the elimination of hazardous catalysts and volatile organic solvents. Additionally this protocol highlights environmentally benign reaction conditions, short reaction times, operational

  在水性介质中使用 β 环糊精开发了一种完全环保且直接的生物重要异色烯 [4,3-b] 吲哚衍生物的方案。这个记录在案的策略包括消除危险的催化剂和挥发性有机溶剂。此外，该方案突出了环境友好的反应条件、反应时间短、操作简单、易于后处理和纯化程序以及产品的良好收率。
• A simple method for the rapid synthesis of 2-amino-7,7-dimethyl-5-oxo-1,4-diaryl-hexahydroquinoline-3-carboxamide derivatives
  作者：Fahimeh Sadat Hosseini、Mohammad Bayat

  DOI：10.1007/s13738-020-01920-3

  日期：2020.9

  AbstractSimple synthesis of oxoquinoline carboxamide derivatives via one-pot, multi-component reaction of enaminones derived from the addition of dimedone to various anilines with aromatic aldehydes and cyanoacetamide is described. Optimal reaction conditions for the synthesis of products were obtained, when EtOH/H2O (1:1) was used as the solvent at 80 °C, in the presence of piperidine as the catalyst

  摘要描述了通过衍生自二甲酮加成各种苯胺与芳香族醛和氰基乙酰胺衍生的烯胺酮的一锅，多组分反应，简单合成氧代喹啉羧酰胺衍生物。在以哌啶为催化剂的情况下，在80°C下使用EtOH / H 2 O（1：1）作为溶剂时，获得了合成产物的最佳反应条件。反应在5至25分钟内完成，收率高至高（74％至85％）。该方案涉及迈克尔反应，亚胺-烯胺互变异构和环化序列。产物的结构由其IR，质量，1 H NMR和13推导出1 H NMR谱。该方法包括一些重要方面，包括在温和条件下的简单操作，易于接近的反应物，后处理程序，高原子经济性以及使用乙醇/水作为绿色介质。 图形摘要