methyl 2-bromo-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 2-bromo-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• 英文别名: Methyl 2-bromo-1-oxo-3,4-dihydronaphthalene-2-carboxylate；methyl 2-bromo-1-oxo-3,4-dihydronaphthalene-2-carboxylate
• 化学式: C₁₂H₁₁BrO₃
• 分子量: 283.122
• InChiKey: KSXJGZMWEVLCRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,2,3,4-四氢-1-氧代-2-萘羧酸甲酯 在 ammonium cerium(IV) nitrate 作用下， 反应 3.0h， 以85%的产率得到methyl 2-bromo-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  用离子液体、[AcMIm]X 和硝酸铈铵 (CAN) 卤化羰基化合物

  摘要：

  离子液体乙酰甲基咪唑鎓卤化物 ([AcMIm]X) 与硝酸铈铵结合可促进多种酮和 1,3-酮酯在 α 位的卤化。离子液体在此既充当试剂又充当反应介质，因此该反应不需要任何有机溶剂或常规卤化剂。当使用自由基猝灭剂 TEMPO 时，反应完全停止。还提出了一种似是而非的激进机制。

  DOI：

  10.1071/ch07061

文献信息

• Halogenation of Carbonyl Compounds by an Ionic Liquid, [AcMIm]X, and Ceric Ammonium Nitrate (CAN)
  作者：Brindaban C. Ranu、Laksmikanta Adak、Subhash Banerjee

  DOI：10.1071/ch07061

  日期：——

  An ionic liquid, acetylmethylimidazolium halide ([AcMIm]X), in combination with ceric ammonium nitrate promotes halogenations of a wide variety of ketones and 1,3-keto esters at the α-position. The ionic liquid acts here as reagent as well as reaction medium, and thus the reaction does not require any organic solvent or conventional halogenating agent. The reaction is completely arrested when the radical

  离子液体乙酰甲基咪唑鎓卤化物 ([AcMIm]X) 与硝酸铈铵结合可促进多种酮和 1,3-酮酯在 α 位的卤化。离子液体在此既充当试剂又充当反应介质，因此该反应不需要任何有机溶剂或常规卤化剂。当使用自由基猝灭剂 TEMPO 时，反应完全停止。还提出了一种似是而非的激进机制。
• A quick, mild and efficient bromination using a CFBSA/KBr system
  作者：Pan-Pan Jiang、Xian-Jin Yang

  DOI：10.1039/c6ra20217a

  日期：——

  chemistry and brominated compounds as building blocks are of paramount importance in organic synthesis. In our study, we have developed an efficient method of bromination by using a CFBSA/KBr system at room temperature in a short reaction time. Notably, this approach has been proven to be applicable to a range of substrates including 1,3-diketones and β-keto esters, phenols, aromatic amines and heteroarenes

  溴化是有机化学中的一个基本转变，而溴化化合物则是有机合成中最重要的组成部分。在我们的研究中，我们通过在室温下以短反应时间使用CFBSA / KBr系统开发了一种有效的溴化方法。值得注意的是，该方法已被证明适用于一系列底物，包括1,3-二酮和β-酮​​酯，苯酚，芳族胺和杂芳烃，具有良好或优异的收率。
• A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides in ionic liquids
  作者：H.M. Meshram、P.N. Reddy、P. Vishnu、K. Sadashiv、J.S. Yadav

  DOI：10.1016/j.tetlet.2005.11.141

  日期：2006.2

  Room temperature ionic liquids (ILs) are used as a green recyclable reaction media for the α-monohalogenation of 1,3-diketones, β-keto-esters and cyclic ketones with N-halosuccinimides in excellent yields in the absence of a catalyst. The recovered ionic liquid was reused five to six times with consistent activity.

  室温离子液体（ILs）用作绿色可循环使用的反应介质，用于在没有催化剂的情况下以极好的收率将1,3-二酮，β-酮酸酯和环状酮与N-卤代琥珀酰亚胺进行α-单卤代反应。回收的离子液体以一致的活性重复使用五到六次。
• Amberlyst-15®-promoted efficient 2-halogenation of 1,3-keto-esters and cyclic ketones using N-halosuccinimides
  作者：H.M. Meshram、P.N. Reddy、K. Sadashiv、J.S. Yadav

  DOI：10.1016/j.tetlet.2004.11.140

  日期：2005.1

  A simple and rigid process has been developed for the alpha-monohalogenation of 1,3-keto-esters with N-halosuccinimides catalyzed by Amberlyst-15((R)) at room temperature to produce the corresponding 2-halo 1,3-keto-esters in high yields. This protocol also extended to alpha-halogenation of cyclic ketones. (C) 2004 Elsevier Ltd. All rights reserved.
• Visible‐Light‐Mediated Stereoselective 1,2‐Iodoalkylation of Alkynes
  作者：Jie‐Jie Liu、Ling Lan、Yu‐Ting Gao、Qi Liu、Liang Cheng、Dong Wang、Li Liu

  DOI：10.1002/adsc.201801636

  日期：2019.3.15

  visible‐light‐mediated and photocatalyst/initiator‐free addition to alkynes has been developed. An atom transfer radical addition (ATRA) mechanistic afforded a broad scope of valuable iodo‐substituted alkenyl derivatives with high E/Z‐selectivities, which are versatile intermediates for the synthesis of various tri‐ and tetra‐ substituted alkenes.

  已开发出可见光介导的和炔烃无光催化剂/引发剂的添加剂。原子转移自由基加成（ATRA）机理提供了广泛的有价值的具有高E / Z选择性的碘取代的烯基衍生物，它们是合成各种三和四取代的烯烃的通用中间体。