meta-phenylseleno acetophenone | 666743-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: meta-phenylseleno acetophenone
• 英文别名: m-phenylselenoacetophenone；Ethanone, 1-[3-(phenylseleno)phenyl]-；1-(3-phenylselanylphenyl)ethanone
• CAS: 666743-33-5
• 化学式: C₁₄H₁₂OSe
• 分子量: 275.209
• InChiKey: ITPWNFPRGWBQPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  meta-phenylseleno acetophenone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (RS)-1-(3-(phenylselanyl)phenyl)ethanol
  参考文献：
  名称：

  Preparation of chiral organochalcogeno-α-methylbenzyl alcohols via biocatalysis. The role of Daucus carota root

  摘要：

  A series of organochalcogeno acetophenones 3 has been submitted to the action of enzymes from Daucus carota root. Some of the chalcogeno ketones tested afforded the chiral organochalcogeno-alpha-methylbenzyl alcohols 4 in excellent enantiomeric excesses (>99%), under mild and environmentally friendly conditions. The stereoselectivity of the reduction is in accordance with Prelog's rule. Enzymatic kinetic resolution as alternative process was used to obtain the chiral ortho-organochalcogeno-alpha-methylbenzyl alcohols in excellent enantiomeric excess (>99%). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.011
• 作为产物：
  描述：

  3'-溴苯乙酮 在 盐酸 、 叔丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 8.5h， 生成 meta-phenylseleno acetophenone
  参考文献：
  名称：

  Preparation of chiral organochalcogeno-α-methylbenzyl alcohols via biocatalysis. The role of Daucus carota root

  摘要：

  A series of organochalcogeno acetophenones 3 has been submitted to the action of enzymes from Daucus carota root. Some of the chalcogeno ketones tested afforded the chiral organochalcogeno-alpha-methylbenzyl alcohols 4 in excellent enantiomeric excesses (>99%), under mild and environmentally friendly conditions. The stereoselectivity of the reduction is in accordance with Prelog's rule. Enzymatic kinetic resolution as alternative process was used to obtain the chiral ortho-organochalcogeno-alpha-methylbenzyl alcohols in excellent enantiomeric excess (>99%). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.011

文献信息

• Microwave-assisted reaction of aryl diazonium fluoroborate and diaryl dichalcogenides in dimethyl carbonate: a general procedure for the synthesis of unsymmetrical diaryl chalcogenides
  作者：Debasish Kundu、Sabir Ahammed、Brindaban C. Ranu

  DOI：10.1039/c2gc35328h

  日期：——

  A convenient, general and efficient procedure for the synthesis of unsymmetrical diaryl chalcogenides has been developed by the reaction of aryl diazonium fluoroborates and diaryl dichalcogenides in the presence of zinc dust in dimethyl carbonate under microwave irradiation. The reactions of a wide range of substituted aryl diazonium fluoroborates and diaryl dichalcogenides have been addressed. The

  通过在碳酸二甲酯中的锌粉存在下，在微波辐射下，使芳基重氮氟硼酸酯与二芳基二卤化氢在碳酸二甲酯存在下反应，已经开发出一种方便，通用且有效的合成不对称二芳基硫属元素化物的方法。已经解决了广泛范围的取代的氟硼酸重氮芳基酯和二芳基二卤化氢的反应。裂解二芳基二卤化氢需要锌粉。快速干燥后获得高纯度产品柱层析 后的原油残留量 蒸发 碳酸二甲酯。
• CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids
  作者：Diego Alves、Cayane G. Santos、Márcio W. Paixão、Letiére C. Soares、Diego de Souza、Oscar E.D. Rodrigues、Antônio L. Braga

  DOI：10.1016/j.tetlet.2009.09.052

  日期：2009.12

  We present here an efficient and ligand-free cross-coupling reaction of organic diselenides with aryl boronic acids using a catalytic amount of CuO nanoparticles in DMSO at 100 °C under air atmosphere. This is a general cross-coupling reaction and was performed with organic diselenides and aryl boronic acids bearing electron-withdrawing and electron-donating groups affording the corresponding selenides

  我们在此介绍了在空气中100°C的DMSO中使用催化量的CuO纳米颗粒在有机二硒化物与芳基硼酸之间进行有效且无配体的交叉偶联反应的方法。这是一般的交叉偶联反应，是用带有负载吸电子基团和供电子基团的有机二硒化物和芳基硼​​酸进行的，从而以良好或极好的收率提供了相应的硒化物。可以容易地回收CuO纳米颗粒并将其用于进一步的催化反应。
• Enantiomerically pure organoseleno-1-arylethanols by enzymatic resolution with Candida antarctica lipase: Novozym 435
  作者：Álvaro T. Omori、Leonardo F. Assis、Leandro H. Andrade、João V. Comasseto、André L.M. Porto

  DOI：10.1016/j.tetasy.2007.04.019

  日期：2007.5

  Racemic organoseleno-1-arylethanols were prepared by ortho-lithiation of arylethanols, followed by sequential reaction with elemental selenium and alkyl halides and by reaction of either aryldiazonium chlorides with diphenyldiselenide or with lithium and magnesium alkylselenolates. Enantiomerically enriched organoseleno-1-arylethanols were obtained by kinetic resolution of the racemic mixtures by esterification catalyzed by Candida antarctica lipase (Novozym 435). In some cases, enantiomeric excesses of up to 99% were obtained both for alcohols and acetates. (C) 2007 Elsevier Ltd. All rights reserved.