(S)-N-(1-phenyl-3-(phenylselanyl)propan-2-yl)benzamide | 869383-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-(1-phenyl-3-(phenylselanyl)propan-2-yl)benzamide
• 英文别名: (S)-N-(3-phenyl-1-(phenylselanyl)propan-2-yl)benzamide；(S)-N-[3-phenyl-1-(phenylselanyl)propan-2-yl]benzamide；Benzamide, N-[(1S)-1-(phenylmethyl)-2-(phenylseleno)ethyl]-；N-[(2S)-1-phenyl-3-phenylselanylpropan-2-yl]benzamide
• CAS: 869383-49-3
• 化学式: C₂₂H₂₁NOSe
• 分子量: 394.375
• InChiKey: DVSQUTGFOMQVKG-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 (4S)-4-benzyl-2-phenyl-4,5-dihydro-1,3-oxazole 在 indium 、 碘 作用下， 以 乙二醇 为溶剂， 反应 0.33h， 以83%的产率得到(S)-N-(1-phenyl-3-(phenylselanyl)propan-2-yl)benzamide
  参考文献：
  名称：

  在微波辐射下通过硫族油酸酯铟促进的区域选择性2-恶唑啉开环反应一锅模块化合成β-硫族酰胺

  摘要：

  我们在本文中描述了微波辅助合成的β-硫属元素酰胺，其通过原位产生的双（有机基硫属元素基）碘化铟（III）促进的2-恶唑啉的区域选择性开环反应而合成。与常规加热方案相比，该方案可以在中等得多的反应时间内以中等到良好的产率制备结构多样的β-硫属元素酰胺。

  DOI：

  10.1016/j.tetlet.2020.152180

文献信息

• Efficient Synthesis of Chiral β-Seleno Amides via Ring-Opening Reaction of 2-Oxazolines and Their Application in the Palladium-Catalyzed Asymmetric Allylic Alkylation
  作者：Antonio L. Braga、Fabrício Vargas、Jasquer A. Sehnem、Rodolpho C. Braga

  DOI：10.1021/jo051451a

  日期：2005.10.1

  selenium nucleophiles. The present method is applicable to the synthesis of β-seleno amides containing thioether, alcohol, and ether moieties in good yields. As an application, the synthesis of a selenocysteine derivative has been accomplished. Additionally, these new compounds were evaluated in the palladium-catalyzed asymmetric allylic alkylation, giving the alkylated products in up to 98% ee.

  通过硒亲核试剂通过手性2-恶唑啉的开环反应，已经有效地合成了一组手性β-硒酰胺。本方法适用于以高收率合成含硫醚，醇和醚部分的β-硒酰胺。作为一种应用，已经完成了硒代半胱氨酸衍生物的合成。此外，在钯催化的不对称烯丙基烷基化反应中对这些新化合物进行了评估，得到烷基化产物的ee高达98％。
• One-Pot Indium Iodide Mediated Synthesis of Chiral β-Seleno Amides and Selenocysteine Derivatives by Ring-Opening Reaction of 2-Oxazolines
  作者：Antonio L. Braga、Fabrício Vargas、Fábio Z. Galetto、Márcio W. Paixão、Ricardo S. Schwab、Paulo S. Taube

  DOI：10.1002/ejoc.200700671

  日期：2007.11

  A set of chiral β-seleno amides were efficiently synthesized by a simple and efficient procedure involving a ring-opening reaction of 2-oxazoline with diorganyl dichalcogenides mediated by indium(I) iodide. As an application, the synthesis of selenocysteine derivatives was accomplished. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  一组手性 β-硒代酰胺通过简单有效的方法有效合成，该方法涉及 2-恶唑啉与二有机二硫属元素化物的开环反应，由碘化铟 (I) 介导。作为应用，完成了硒代半胱氨酸衍生物的合成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Modular chiral β-selenium-, sulfur-, and tellurium amides: synthesis and application in the palladium-catalyzed asymmetric allylic alkylation
  作者：Fabrício Vargas、Jasquer A. Sehnem、Fabio Z. Galetto、Antonio L. Braga

  DOI：10.1016/j.tet.2007.10.086

  日期：2008.1

  have been efficiently synthesized from inexpensive and easily available 2-oxazolines. All the selenium, sulfur, and tellurium compounds were evaluated as chiral ligands in the palladium-catalyzed asymmetric allylic alkylation. The corresponding alkylated products were obtained in excellent enantiomeric excess, using BSA/CH2Cl2 as the base/solvent system.

  已经从廉价且容易获得的2-恶唑啉有效地合成了一系列模块化手性β-硫属元素酰胺。在硒催化的不对称烯丙基烷基化反应中，所有硒，硫和碲化合物均被评价为手性配体。使用BSA / CH 2 Cl 2作为碱/溶剂体系，可以以极好的对映体过量获得相应的烷基化产物。
• Microwave-Mediated Palladium-Catalyzed Asymmetric Allylic Alkylation Using Chiral -Seleno Amides
  作者：Antonio L. Braga、Fabrício Vargas、Jasquer A. Sehnem、Ludger A. Wessjohann

  DOI：10.1002/ejoc.200600707

  日期：2006.11

  A class of enantiopure β-seleno amide palladium complexes catalyze the microwave-accelerated enantioselective allylic alkylation of rac-1,3-diphenyl-2-propenyl acetate with different malonates. Good yields and enantiomeric excess values of up to 94 % ee were obtained after irradiation times of 2 or 4 min. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  一类对映纯的 β-硒酰胺钯配合物催化 rac-1,3-二苯基-2-丙烯基乙酸酯与不同丙二酸酯的微波加速对映选择性烯丙基烷基化。在 2 或 4 分钟的照射时间后获得了良好的产率和高达 94% ee 的对映体过量值。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Mild and efficient one-pot synthesis of chiral β-chalcogen amides via 2-oxazoline ring-opening reaction mediated by indium metal
  作者：Antonio L. Braga、Fábio Z. Galetto、Paulo S. Taube、Márcio W. Paixão、Claudio C Silveira、Devender Singh、Fabrício Vargas

  DOI：10.1016/j.jorganchem.2008.08.031

  日期：2008.11

  A simple and efficient procedure for the synthesis of β-seleno and β-thio amides via the ring-opening reaction of chiral 2-oxazolines in the presence of indium metal has been developed. Features of this method include the following: (i) easily and accessible starting materials; (ii) indium metal is more stable and less expensive then its respective salts; (iii) useful to excellent yields of β-chalcogen

  已经开发了一种简单有效的方法，用于在铟金属存在下通过手性2-恶唑啉的开环反应合成β-硒代和β-硫代酰胺。该方法的特点包括：（i）容易获得的起始材料；（ii）铟金属比其各自的盐更稳定，更便宜；（iii）有利于β-硫属元素酰胺衍生物的优异产率。