2-iodo-1,3-diphenyl-1-propanone | 126550-94-5

• 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-iodo-1,3-diphenyl-1-propanone
• 英文别名: α-iodo-α-benzylacetophenone；α-Ioddihydrochalkon；2-iodo-1,3-diphenylpropan-1-one；2-Jod-1,3-diphenyl-propan-1-on
• CAS: 126550-94-5
• 化学式: C₁₅H₁₃IO
• 分子量: 336.172
• InChiKey: KSMAAKMQBDSXSF-UHFFFAOYSA-N

物化性质

• 沸点：
  415.3±45.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 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-iodo-1,3-diphenyl-1-propanone 在 锌 作用下， 反应 2.0h， 生成 ω-苄基苯乙酮
  参考文献：
  名称：

  Nesmeyanov, N. A.; Kharitonov, V. G.; Berman, S. T., Doklady Chemistry, 1984, vol. 274, p. 28 - 31

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[iodo(triphenyl)-λ5-arsanyl]-1,3-diphenylpropan-1-one 以44%的产率得到
  参考文献：
  名称：

  NESMEYANOV, NIK. A.;XARITONOV, V. G.;BERMAN, S. T.;PETROVSKIJ, P. V.;REUT+, DOKL. AN CCCP, 1984, 274, N 3, 606-610

  摘要：

  DOI：

文献信息

• Oxidative iodination of carbonyl compounds using ammonium iodide and oxone®
  作者：Mahender Reddy Marri、Arun Kumar Macharla、Swamy Peraka、Narender Nama

  DOI：10.1016/j.tetlet.2011.09.106

  日期：2011.12

  A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone® as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones

  通过使用NH 4 I作为碘的来源和Oxone®作为氧化剂，已经报道了一种简单，有效，温和和区域选择性的羰基化合物氧碘化方法。各种羰基化合物（如芳烷基酮，脂族酮（无环和环状）和β-酮酯）以中等至优异的收率发展为各自的α-单碘化产物。不对称脂族酮反应平稳，生成1-碘和3-碘酮的混合物，主要形成1-碘产物。
• Iodine-catalyzed α,β-dehydrogenation of ketones and aldehydes generating conjugated enones and enals
  作者：Yuanjie Cao、Long Liu、Tianzeng Huang、Tieqiao Chen

  DOI：10.1039/d0nj01244k

  日期：——

  A transition metal-free α,β-dehydrogenation of ketones and aldehydes was developed. This reaction was conducted in a facile I2/KI/DMSO system to produce the corresponding unsaturated compounds in good to high yields. The gram-scale experiment also indicated the potential synthetic value of this new reaction in organic synthesis. In the reaction, DMSO acted as both solvent and mild oxidant.

  研究了酮和醛的无过渡金属α，β-脱氢反应。该反应在容易的I 2 / KI / DMSO系统中进行，以高至高收率生产相应的不饱和化合物。克级实验还表明了这种新反应在有机合成中的潜在合成价值。在反应中，DMSO既充当溶剂又充当弱氧化剂。
• α,α-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones
  作者：Rafael D. C. Gallo、Anees Ahmad、Gustavo Metzker、Antonio C. B. Burtoloso

  DOI：10.1002/chem.201704609

  日期：2017.12.1

  A one‐pot alkylation–halogenation of ketosulfoxonium ylides in the presence of alkyl halides is described. The method furnishes several gem‐difunctionalized haloketones (an alkyl and F, Cl, Br, or I) in good yields. Replacing alkyl halides with a mixture of electrophilic halogen species and various halide anions led to gem‐dihalogenated ketones containing a combination of the same or two different

  描述了在存在烷基卤化物的情况下一酮醚化ox酮的一锅烷基化-卤化反应。该方法以良好的收率提供了几种宝石双官能化的卤代酮（烷基和F，Cl，Br或I）。用亲电子卤素物质和各种卤化物阴离子的混合物代替烷基卤化物，会导致宝石二卤代酮含有相同或两种不同卤素的组合。动力学同位素效应以及反应动力学实验使人们洞悉了这些反应的机理。
• Simple Diastereoselectivity on Addition of α-Haloalkyl Grignard Reagents to Benzaldehyde
  作者：Volker Schulze、Peter G. Nell、Andrew Burton、Reinhard W. Hoffmann

  DOI：10.1021/jo034138m

  日期：2003.5.1

  The addition of alpha-haloalkyl Grignard reagents to benzaldehyde occurs with simple diastereoselectivity substantially higher than that of the corresponding lithium reagents. Reaction in the presence of dimethyl-aluminum chloride suppresses subsequent Oppenauer oxidation of the resulting Mg-alkoxides by excess benzaldehyde.

  将α-卤代烷基格氏试剂添加到苯甲醛中时，其简单的非对映选择性大大高于相应的锂试剂。在二甲基氯化铝存在下的反应可抑制随后的Oppenauer通过过量的苯甲醛氧化生成的Mg-醇盐。
• An expedient protocol for conversion of olefins to α-bromo/iodoketones using IBX and NBS/NIS
  作者：Jarugu Narasimha Moorthy、Kalyan Senapati、Nidhi Singhal

  DOI：10.1016/j.tetlet.2009.03.032

  日期：2009.5

  A variety of olefins have been shown to undergo conversion to the corresponding alpha-bromo/iodoketones when reacted with NBS/NIS and IBX in DMSO at room temperature. While the reaction is found to occur rapidly with e-rich arylolefins leading to the corresponding haloketones in 65-95% yields in 0.3-3.0 h, those containing e-withdrawing groups are found to yield diketones concomitantly, such that the latter are the exclusive products over extended duration of the reactions. (C) 2009 Elsevier Ltd. All rights reserved.