2,3-dibromo-1,3-diphenylpropan-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,3-dibromo-1,3-diphenylpropan-1-one
• 英文别名: rac-(S,S)-2,3-dibromo-1,3-diphenylpropan-1-one；(2RS,3RS)-2,3-dibromo-1,3-diphenyl-propan-1-one；(2RS,3RS)-2,3-Dibrom-1,3-diphenyl-propan-1-on；(2RS:3RS)-2.3-Dibrom-1,3-diphenyl-propanon-(1)；(2R,3R)-2,3-dibromo-1,3-diphenylpropan-1-one
• 化学式: C₁₅H₁₂Br₂O
• 分子量: 368.068
• InChiKey: LYAGBKGGYRLVTR-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2,3-dibromo-1,3-diphenylpropan-1-one 在 三乙胺 作用下， 以 苯 为溶剂， 反应 3.0h， 以99.5%的产率得到苯亚甲基苯乙酮
  参考文献：
  名称：

  邻二卤化物光脱卤制烯烃

  摘要：

  在甲醇或三乙胺存在下辐照邻位二卤化物导致有效脱卤以再生烯烃。

  DOI：

  10.1246/cl.1983.1297
• 作为产物：
  描述：

  反式-查耳酮 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 生成 2,3-dibromo-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  Modification of chemical reactivity upon cyclodextrin encapsulation:

  摘要：

  Asymmetric bromination of chalcone and benzylideneacetone (trans-isomers) in crystalline beta-cyclodextrin complex was studied. While bromination of chalcone in the absence of beta-cyclodextrin yields erythro-dibromide, bromination of beta-cyclodextrin-chalcone complex results in the formation of a mixture of erythro- and threo-dibromides respectively in the ratio 80:20. Complexation does not induce any variation in the bromination pattern in the case of trans-benzylideneacetone. These observations have been accounted for in terms of different conformations of the enones in the beta-cyclodextrin-enone complexes. Complex formation between the substrate and cyclodextrin has been confirmed by various physical methods.

  DOI：

  10.1016/s0040-4020(01)85274-1

文献信息

• Stereoselective debromination of aryl-substituted vic-dibromide with indium metal
  作者：Brindaban C. Ranu、Sankar K. Guchhait、Arunkanti Sarkar

  DOI：10.1039/a806530f

  日期：——

  Debromination of both meso and dl (erythro and threo) aryl-substituted vic-dibromides with indium metal in MeOH leads to trans-alkenes exclusively.

  在甲醇中，钌金属对间位和对位（赤型和苏型）芳基取代的连二溴化物进行脱溴反应，仅生成反式烯烃。
• Dibrominated addition and substitution of alkenes catalyzed by Mn₂(CO)₁₀
  作者：Xianheng Song、Shanshui Meng、Hong Zhang、Yi Jiang、Albert S. C. Chan、Yong Zou

  DOI：10.1039/d1cc04534b

  日期：——

  A practical method for the dibromination of alkenes without using molecular bromine is consistently appealing in organic synthesis. Herein, we report Mn-catalyzed dibrominated addition and substitution of alkenes only with N-bromosuccinimide, producing a variety of synthetically valuable dibrominated compounds in moderate to high yields.

  一种不使用分子溴的烯烃二溴化的实用方法在有机合成中一直很有吸引力。在此，我们报告了仅用 N-溴代琥珀酰亚胺对烯烃进行 Mn 催化的二溴化加成和取代，以中等至高产率生产各种具有合成价值的二溴化化合物。
• Brominations with Pr4NBr9 as a Solid Reagent with High Reactivity and Selectivity­
  作者：Jan Streuff、Sebastian Riedel、Thorsten Beck、Heike Haller

  DOI：10.1055/s-0033-1340705

  日期：——

  room-temperature solid reagent for rapid bromination reactions of various substrates. The reagent exhibits reactivity similar to that of elemental bromine, but shows higher selectivity and it is easier and safer to store and to handle. Tetrapropylammonium nonabromide (Pr4NBr9) is introduced as a room-temperature solid reagent for rapid bromination reactions of various substrates. The reagent exhibits reactivity

  摘要 引入四丙基九溴化铵（Pr 4 NBr 9）作为室温固体试剂，用于各种底物的快速溴化反应。该试剂显示出与元素溴相似的反应性，但显示出更高的选择性，并且更容易，更安全地存储和处理。 引入四丙基九溴化铵（Pr 4 NBr 9）作为室温固体试剂，用于各种底物的快速溴化反应。该试剂显示出与元素溴相似的反应性，但显示出更高的选择性，并且更容易，更安全地存储和处理。
• Organocatalysis as a Safe Practical Method for the Stereospecific Dibromination of Unsaturated Compounds
  作者：Gloria Hernández-Torres、Bin Tan、Carlos F. Barbas

  DOI：10.1021/ol300456x

  日期：2012.4.6

  Organocatalytic stereospecific dibromination of a wide variety of functionalized alkenes was achieved using a stable, inexpensive halogen source, 1,3-dibromo 5,5-dimethylhydantoin, and a simple thiourea catalyst at room temperature. The presence of a tertiary amine enhanced the rate of the dibromination reaction, and yields were good in various solvents, including aqueous solvents. The procedure was

  在室温下，使用稳定，廉价的卤素源，1,3-二溴5,5,5-二甲基乙内酰脲和简单的硫脲催化剂可实现多种官能化烯烃的有机催化立体有择二溴化反应。叔胺的存在提高了二溴化反应的速率，并且在包括水性溶剂在内的各种溶剂中产率都很高。通过使用1，3-二氯乙内酰脲衍生物，该方法扩展到炔烃和芳环以及二氯化反应。
• Solvent shifts induced by dimethylsulphoxide in α-proton magnetic resonances of carbonyl compounds
  作者：M.C. Cabaleiro、N.N. Giagante

  DOI：10.1016/0040-4020(80)80082-2

  日期：1980.1

  The chemical shifts of α- and β-proton resonances of a number of carbonyl compounds in carbon tetrachloride and dimethylsulphoxide have been determined. The magnitude of the effect of the solvent change on the α-proton resonances seems to vary directly with its lability.

  已经确定了四氯化碳和二甲基亚砜中许多羰基化合物的α和β质子共振的化学位移。溶剂变化对α-质子共振的影响的大小似乎直接随其不稳定性而变化。