di-2-[(1S)-1-(methylthio)ethyl]phenyl diselenide | 278790-74-2

• 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: di-2-[(1S)-1-(methylthio)ethyl]phenyl diselenide
• 英文别名: Diselenide, bis[2-[(1S)-1-(methylthio)ethyl]phenyl]；1-[(1S)-1-methylsulfanylethyl]-2-[[2-[(1S)-1-methylsulfanylethyl]phenyl]diselanyl]benzene
• CAS: 278790-74-2
• 化学式: C₁₈H₂₂S₂Se₂
• 分子量: 460.425
• InChiKey: IZOGLAMCPKVHIF-KBPBESRZSA-N

物化性质

• 沸点：
  520.6±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  di-2-[(1S)-1-(methylthio)ethyl]phenyl diselenide 在 盐酸 、 锌 作用下， 以 乙醚 、 水 为溶剂， 生成
  参考文献：
  名称：

  A Simple Zinc-Mediated Preparation of Selenols

  摘要：

  在酸性条件下，锌可将二硒化合物还原为硒醇，这些硒醇既可分离出来，也可就地与烷基卤反应生成烷基硒醚，或与环氧化物反应得到β-羟基硒醚。

  DOI：

  10.1055/s-2008-1078408
• 作为产物：
  描述：

  (R)-(+)-2-溴-α-甲基苯甲醇 在 氢氧化钾 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 生成 di-2-[(1S)-1-(methylthio)ethyl]phenyl diselenide
  参考文献：
  名称：

  新型含硫手性二硒化物对烯烃的高效不对称硒代甲氧基化和硒代羟基化

  摘要：

  描述了新的手性非外消旋含二硒化物的合成。通过用溴和三氟甲磺酸银处理由该二硒化物产生的亲电硒试剂已用于实现烯烃的硒代甲氧基化和硒代羟基化。这些加成反应以良好的化学产率和高的非对映选择性发生。

  DOI：

  10.1016/s0040-4039(00)00358-0
• 作为试剂：
  描述：

  1-苯基-1-环已烯 在 ammonium peroxydisulfate 、 水 、 di-2-[(1S)-1-(methylthio)ethyl]phenyl diselenide 作用下， 以 乙腈 为溶剂， 以80%的产率得到(1R,2R)-1-phenyl-1,2-cyclohexanediol
  参考文献：
  名称：

  Diastereo and Enantioselective Synthesis of 1,2-Diols Promoted by Electrophilic Selenium Reagents

  摘要：

  Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO3H generated "in situ" by oxidation of (PhSe)(2) with (NH4)(2)S2O8 at reflux in a 3:1 mixture of MeCN-H2O. Interestingly the reaction can be performed in "one pot" using a catalytic amount of diselenide affording the corresponding diols (5 and 6) with good yield and good level of diastereo- and enantioselectivity.

  DOI：

  10.1080/10426500801900881

文献信息

• Efficient asymmetric selenocyclizations of alkenyl oximes into cyclic nitrones and 1,2-oxazines promoted by sulfur containing diselenides
  作者：Marcello Tiecco、Lorenzo Testaferri、Luana Bagnoli、Valentina Purgatorio、Andrea Temperini、Francesca Marini、Claudio Santi

  DOI：10.1016/s0957-4166(02)00013-7

  日期：2001.12

  were used in situ to promote the asymmetric selenocyclization of γ-alkenyl oximes and δ-phenyl-γ-alkenyl oximes. The course of these reactions and hence the structures of the cyclization products were dictated by the (E)- or (Z)-geometry of the starting oximes. The two types of cyclization products were either the cyclic nitrones or the 1,2-oxazines; in both cases the reactions proceeded with excellent

  用溴处理二-2-[（（1S）-1-（甲硫基）乙基]苯基二硒化物或二-2-甲氧基-6-[（（1S ] -1-甲硫基）乙基]苯基二硒化物三氟甲磺酸银可提供相应的亲电子的硒化三氟甲磺酸酯，该三氟甲磺酸酯原位用于促进γ-烯基肟和δ-苯基-γ-烯基肟的不对称硒烯环化。这些反应的过程以及因此环化产物的结构由起始肟的（E）-或（Z）-几何形状决定。两种类型的环化产物是环状硝酮或1,2-恶嗪。在两种情况下，反应均以优异的收率，完全的区域选择性和良好的非对映选择性进行。
• Enantioselective Methoxyselenenylation of α,β-Unsaturated Aldehydes
  作者：Claudio Santi、Stefano Santoro、Cristina Tomassini、Fabio Pascolini、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1055/s-0028-1087936

  日期：——

  In this communication we propose a convenient methodology to effect the asymmetric methoxyselenenylation of β-aryl α,β-unsaturated aldehydes using as electrophilic reagent an optically pure sulfur-containing selenenyl chloride. Mechanistic aspects of the reaction were investigated and simple manipulations to prepare optically pure derivatives are reported.

  在这篇通讯中，我们提出了一种简便的方法，即使用光学纯的含硫硒氯作为亲电试剂，对δ-芳基δ±,δ-不饱和醛进行不对称甲氧基硒化反应。报告研究了该反应的机理，并介绍了制备光学纯衍生物的简单操作。
• Conjugated Additions of Selenium Containing Enolates to Enones - Enantioselective Synthesis of ?-Oxo-?-Seleno Esters and Their Facile Transformations
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1002/ejoc.200400686

  日期：2005.2

  containing chiral auxiliary have been employed to bring about 1,4-addition reactions to enones. These reactions generate δ-oxo-α-seleno esters in good yields and with excellent regio- and diastereoselectivities. The results obtained clearly indicate that the Lewis acids, employed to activate the starting enones towards addition, greatly influence reactivity as well as the stereochemical outcomes of

  衍生自苯基硒乙酸甲酯和其他带有手性助剂硒的乙酸盐的钛烯醇化物已被用于对烯酮进行 1,4-加成反应。这些反应以良好的产率和出色的区域选择性和非对映选择性生成 δ-氧代-α-硒代酯。获得的结果清楚地表明，用于激活起始烯酮加成的路易斯酸极大地影响反应性以及这些反应的立体化学结果。TiCl4 络合导致特别有效地促进 1,4-加成。有机硒部分的简单操作允许一些对映体纯的 δ-氧-α-樟脑硒酯转化为相应的 δ-氧-α-羟基或 δ-氧-α-烯丙基酯或三取代的四氢呋喃。
• Optically active isoxazolidines and 1,3-amino alcohols by asymmetric selenocyclization reactions of O-allyl oximes
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/s0957-4166(01)00543-2

  日期：2001.11

  The selenyl triflate generated from the reaction of di-2-[(1S)-1-(methylthio)ethyl]phenyl diselenide with silver triflate reacts with various substituted O-allyl oximes to promote ring closure, which affords optically active isoxazolidines in high yields and with good diastereoselectivity (up to 93:7). Enantiomerically enriched 1,3-amino alcohols can be easily obtained by NO bond cleavage of these

  由二-2-[（（1S）-1-（甲硫基）乙基]苯基二硒化物与三氟甲磺酸银反应生成的三氟甲磺酸硒酯与各种取代的O-烯丙基肟反应以促进闭环，从而在高浓度下提供光学活性的异恶唑烷收率高，非对映选择性好（高达93：7）。对映体富集的1,3-氨基醇可以很容易地获得Ñ  ö这些杂环，其容易通过用在含水乙酸中的锌进行的键裂解。
• A sulfur-containing diselenide as an efficient chiral reagent in asymmetric selenocyclization reactions
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Luana Bagnoli、Claudio Santi、Andrea Temperini

  DOI：10.1016/s0957-4166(01)00248-8

  日期：2001.6

  Treatment of the di-2-[(IS)-1-(methylthio)ethyl]phenyl diselenide with bromine and silver triflate afforded the corresponding selenyl triflate which was used in situ as a strongly electrophilic selenium reagent to effect the asymmetric synthesis of oxygen- or nitrogen-containing heterocycles. Cyclic ethers, lactones, lactams or N-protected pyrrolidines have been prepared in good yield with complete regioselectivity and high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.