α,α-dibromo-2'-methoxyacetophenone | 1121543-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,α-dibromo-2'-methoxyacetophenone
• 英文别名: 2,2-dibromo-2'-methoxyacetophenone；2,2-dibromo-1-(2-methoxyphenyl)ethanone；2,2-Dibromo-1-(2-methoxyphenyl)ethan-1-one
• CAS: 1121543-12-1
• 化学式: C₉H₈Br₂O₂
• 分子量: 307.969
• InChiKey: KNMHFQVDFCAOSW-UHFFFAOYSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  305.8±27.0 °C(Predicted)
• 密度：
  1.793±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α,α-dibromo-2'-methoxyacetophenone 在 吡啶 、 水 作用下， 以 乙腈 为溶剂， 反应 27.0h， 以76%的产率得到邻甲氧基苯甲酸
  参考文献：
  名称：

  Bromophilic substitution/carbophilic substitution cascade reactions of α,α-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles

  摘要：

  alpha,alpha-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford alpha-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.057
• 作为产物：
  描述：

  2'-甲氧基苯乙酮 在 溴 作用下， 以 氯仿 为溶剂， 以95%的产率得到α,α-dibromo-2'-methoxyacetophenone
  参考文献：
  名称：

  Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C–Br bonds

  摘要：

  An efficient method for the formation of alpha-carbonyl-monosubstituted acetophenones from ortho-methoxy-and ortho-hydroxy-alpha,alpha-dibromoacetopheiiones and a range of selected nucleophiles, occurring via a carbophilic substitution/bromophilic substitution/protonation cascade process, is described. In turn, the preparation of alpha,alpha-dibromoacetophenones, isolated in high yields, relies on the neighboring group participation of the ortho-substituents in the starting ortho-substituted acetophenones. (C) 2008 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetlet.2008.11.104

文献信息

• 一种由α,α-二溴代酮一锅法制备α-砜基酮类化合物的合成方法
  申请人：温州大学

  公开号：CN110305048A

  公开（公告）日：2019-10-08

  本发明公开了一种以α,α‑二溴代酮类化合物为原料，一锅法合成具有高附加值的α‑砜基酮类化合物的方法。本方法从简单易得的α,α‑二溴代酮出发，不需要分离α‑溴代酮中间体，一锅法合成α‑砜基酮衍生物，减少了中间产物的分离过程，缩短了步骤，符合绿色环保要求；此外，本方法步骤简单易于操作，无需添加过渡金属试剂，直接使用经济廉价、污染小的亚磺酸盐同时作为α,α‑二溴代酮还原脱溴的促进剂和砜化试剂，节约了成本，增加了反应的经济效益。本发明发展出的一锅法制备α‑砜基酮类衍生物的体系为该类化合物的制备提供了全新的合成方法，具有良好的工业化前景和潜在的应用价值。
• Substituent Effects on the Reaction of β-Benzoylalanines with <i>Pseudomonas fluorescens</i> Kynureninase
  作者：Sunil Kumar、Vijay B. Gawandi、Nicholas Capito、Robert S. Phillips

  DOI：10.1021/bi100955b

  日期：2010.9.14

  downward curvature. This suggests that there is a change in rate-determining step for benzoate formation with different substituents, from gem-diol formation for electron-donating substituents to Cβ−Cγ bond cleavage for electron-withdrawing substituents. Rapid-scanning stopped-flow kinetic experiments demonstrated that substituents have relatively minor effects on formation of the quinonoid and 348 nm intermediates

  Kynureninase是一种吡咯醛5'-磷酸依赖性酶，可催化1- kynurenine的水解裂解，生成1-丙氨酸和邻氨基苯甲酸。β-苯甲酰基升丙氨酸，的类似物升-kynurenine缺少芳香族氨基，显示出了良好的基板kynureninase从荧光假单胞菌，和从所述第二产品的释放的速率决定步骤变化，升-Ala，形成第一个产物苯甲酸酯[Gawandi，VB，et al。（2004）Biochemistry 43，3230-3237]。在这项工作中，一系列的芳基取代的β-苯甲酰基-dl合成了丙氨酸，并用荧光假单胞菌的犬尿苷酶评估了底物的活性。具有吸电子和供电子取代基的4-取代的β-苯甲酰基-dl-丙氨酸的k cat和k cat / K m的哈米特分析是非线性的，具有向下的曲率。这表明，有在对苯甲酸地层与不同的取代率决定步骤的改变，从宝石-二醇形成为给电子取代基至C β -C γ吸电子取代基的键
• [EN] ANTI VIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：PASTEUR INSTITUT KOREA

  公开号：WO2010046780A2

  公开（公告）日：2010-04-29

  There is provided small molecule anti-human immunodeficiency virus (anti-HIV) compounds as well as a phenotypic cell-based high throughput screening (HTS) assay for their identification.
• Bromophilic substitution/carbophilic substitution cascade reactions of α,α-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles
  作者：Jovana Tatar、Rade Marković、Milovan Stojanović、Marija Baranac-Stojanović

  DOI：10.1016/j.tetlet.2010.07.057

  日期：2010.9

  alpha,alpha-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford alpha-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained. (C) 2010 Elsevier Ltd. All rights reserved.
• Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C–Br bonds
  作者：Jovana Tatar、Marija Baranac-Stojanović、Milovan Stojanović、Rade Marković

  DOI：10.1016/j.tetlet.2008.11.104

  日期：2009.2

  An efficient method for the formation of alpha-carbonyl-monosubstituted acetophenones from ortho-methoxy-and ortho-hydroxy-alpha,alpha-dibromoacetopheiiones and a range of selected nucleophiles, occurring via a carbophilic substitution/bromophilic substitution/protonation cascade process, is described. In turn, the preparation of alpha,alpha-dibromoacetophenones, isolated in high yields, relies on the neighboring group participation of the ortho-substituents in the starting ortho-substituted acetophenones. (C) 2008 Elsevier Ltd. All rights reserved