(1R,2R)-1,2-diphenyl-2-(phenylselanyl)ethanol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1R,2R)-1,2-diphenyl-2-(phenylselanyl)ethanol
• 英文别名: (1R,2R)-1,2-diphenyl-2-(phenylseleno)ethanol；2-phenylseleno-1,2-diphenylethanol；(1R,2R)-1,2-diphenyl-2-phenylselanylethanol
• 化学式: C₂₀H₁₈OSe
• 分子量: 353.322
• InChiKey: RCYOQUVKIQPOCQ-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  顺式-二苯乙烯 、 二苯基二硒醚 在 亚碘酰苯 、 水 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以55%的产率得到(1R,2R)-1,2-diphenyl-2-(phenylselanyl)ethanol
  参考文献：
  名称：

  碘代苯介导的烯烃三组分硒官能化

  摘要：

  通过市售的高价碘（III）试剂PhIO，开发了烯烃，二硒化物与水，醇，酚，羧酸或胺的三组分反应。这种方法可以在环境条件下获得大多数具有毒理学功能的亚硒代衍生物，并且产率极高，非对映选择性很高。所开发的反应显示出高水平的官能团相容性，并且适合于苯乙烯官能化生物分子的后期官能化。还介绍了反应机理的初步研究。

  DOI：

  10.1021/acs.joc.1c00257

文献信息

• Synthesis of enantiomerically enriched β-hydroxy selenides by catalytic asymmetric ring opening of meso-epoxides with (phenylseleno)silanes
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Francesca Del Verme、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/j.tet.2008.01.126

  日期：2008.4

  The first example of the enantioselective ring opening of meso-epoxides by (phenylseleno)silanes using salen(Cr)complexes as catalyst is described. This desymmetrization reaction constitutes a simple and convenient approach to synthetically versatile optically active β-hydroxy selenides.

  的对映选择性开环的第一实施例的内消旋通过使用萨伦（Cr）的络合物作为催化剂进行说明（phenylseleno）硅烷-环氧化物。该去对称化反应构成了合成通用的光学活性β-羟基硒化物的简便方法。
• Scandium–bipyridine-catalyzed, enantioselective selenol addition to aromatic meso-epoxides
  作者：Andreas Tschöp、Mecheril Valsan Nandakumar、Oksana Pavlyuk、Christoph Schneider

  DOI：10.1016/j.tetlet.2007.12.006

  日期：2008.2

  A chiral scandium–bipyridine complex catalyzes the highly enantioselective addition of phenylselenol to aromatic meso-epoxides and furnishes 1,2-seleno alcohols in good yields and up to 94% ee. In addition, a sequential, one-pot epoxide opening-reduction protocol has been developed for the direct synthesis of 1,2-diaryl carbinols.

  手性scan-联吡啶配合物催化苯硒醇向芳族内消旋环氧化合物的高度对映选择性加成，并以良好的收率和高达94％的ee浓度提供1,2-硒醇。另外，已经开发出一种顺序的，一锅法的环氧开放还原方案，用于直接合成1,2-二芳基甲醇。
• Catalytic Asymmetric Ring-Opening Reaction of<i>meso</i>-Epoxides with Aryl Selenols and Thiols Catalyzed by a Heterobimetallic Gallium-Titanium-Salen Complex
  作者：Jiangtao Sun、Minghua Yang、Fang Yuan、Xuefeng Jia、Xia Yang、Yi Pan、Chengjian Zhu

  DOI：10.1002/adsc.200800767

  日期：2009.4

  Abstractmagnified imageA chiral heterobimetallic Lewis acid complex has been developed as an efficient catalyst. The enantioselective desymmetrization of meso‐epoxides with aryl selenols and thiols catalyzed by the heterobimetallic complex has been optimized. The optically active β‐arylseleno alcohols and β‐hydroxy sulfides were obtained in good yields and high enantioselectivities (up to 97% ee and 92% ee, respectively). A strong synergistic effect between different Lewis acids was exhibited in the catalytic process.
• Enantioselective Ring-Opening Reaction of <i>m</i><i>eso-</i>Epoxides with ArSeH Catalyzed by Heterometallic Ti−Ga−Salen System
  作者：Minghua Yang、Chengjian Zhu、Fang Yuan、Yijun Huang、Yi Pan

  DOI：10.1021/ol0503034

  日期：2005.5.1

  [GRAPHICS]The first example of enantioselective ring-opening reaction of meso-epoxides with aryl selenols to give optically active beta-arylseleno alcohol in up to 97% ee was realized, using a chiral Ti-Ga-Salen heterometallic catalyst. A strong synergistic effect of different Lewis acids in the system was exhibited in the catalytic process.
• Iodosobenzene-Mediated Three-Component Selenofunctionalization of Olefins
  作者：Zhi-Peng Liang、Wei Yi、Peng-Fei Wang、Gong-Qing Liu、Yong Ling

  DOI：10.1021/acs.joc.1c00257

  日期：2021.4.2

  A three-component reaction of olefin, diselenide and water, alcohols, phenol, carboxylic acid, or amine by a commercially available hypervalent iodine(III) reagent, PhIO, was developed. This method provides access to a wide range of vicinally functionalized selenoderivatives under ambient conditions with mostly excellent yields and high diastereoselectivity. The developed reaction displays high levels

  通过市售的高价碘（III）试剂PhIO，开发了烯烃，二硒化物与水，醇，酚，羧酸或胺的三组分反应。这种方法可以在环境条件下获得大多数具有毒理学功能的亚硒代衍生物，并且产率极高，非对映选择性很高。所开发的反应显示出高水平的官能团相容性，并且适合于苯乙烯官能化生物分子的后期官能化。还介绍了反应机理的初步研究。