2-hydroxy-1-phenylethyl phenyl selenide | 79092-14-1

• 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: 2-hydroxy-1-phenylethyl phenyl selenide
• 英文别名: 2-Phenyl-2-(phenylselenenyl)ethanol；2-phenyl-2-(phenylselanyl)ethanol；2-phenylseleno-2-phenylethanol；2-phenyl-2-(phenylselenyl)ethanol；2-Phenyl-2-phenylselanylethanol
• CAS: 79092-14-1
• 化学式: C₁₄H₁₄OSe
• 分子量: 277.225
• InChiKey: FVHQAHTXLCMHAW-UHFFFAOYSA-N

物化性质

• 沸点：
  392.7±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1-phenylethyl phenyl selenide 在 N-甲基吗啉 、 偶氮二异丁腈 、 一氧化碳 、 三(三甲基硅基)硅烷 作用下， 以 二氯甲烷 、 苯 为溶剂， 20.0 ℃ 、8.11 MPa 条件下， 生成 (E)-3-phenethyloxy-acrylic acid ethyl ester
  参考文献：
  名称：

  Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization

  摘要：

  [GRAPHICS]b-Hydroxyalkyl aryl chalcogenides, readily available by regioselective ring-opening of epoxides with nucleophilic benzeneselenolate or tellurolate, were O-alkylated by treatment with ethyl propiolate or (E)-1,2-bis(phenylsulfonyl)ethylene. Subsequent carbonylation/reductive cyclization in the presence of AIBN/TTMSS and carbon monoxide (80 atm) afforded tetrahydrofuran-3-ones in moderate to good yields.

  DOI：

  10.1021/ol016127q
• 作为产物：
  描述：

  氧化苯乙烯 、 tris(phenylseleno)borane 在 碳酸氢钠 作用下， 生成 2-hydroxy-1-phenylethyl phenyl selenide
  参考文献：
  名称：

  Unusual reactivity of selenoboranes towards epoxides: new selective routes to b-hydroxyselenides and allylalcohols

  摘要：

  DOI：

  10.1016/s0040-4039(01)92941-7

文献信息

• Regioselective ring-opening reactions of 1,2-epoxides with thiols and arylselenols directly promoted by [Bmim]BF4
  作者：Ming-Hua Yang、Guo-Bing Yan、Yun-Fa Zheng

  DOI：10.1016/j.tetlet.2008.08.109

  日期：2008.11

  Regioselective ring-opening reactions of 1,2-epoxides with ArSH and ArSeH promoted by ionic liquid [Bmim]BF4 were investigated. A variety of β-hydroxy selenides and β-hydroxy sulfides were obtained in excellent yields (81–99%) with good regioselectivities using a mild, simple and environmentally benign procedure.

  研究了离子液体[Bmim] BF 4促进的1,2-环氧化物与ArSH和ArSeH的区域选择性开环反应。使用温和，简单且对环境有益的方法，可以以优异的收率（81–99％）获得各种β-羟基硒化物和β-羟基硫化物，且具有良好的区域选择性。
• A Simple Zinc-Mediated Preparation of Selenols
  作者：Claudio Santi、Stefano Santoro、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1055/s-2008-1078408

  日期：2008.6

  Under acidic conditions zinc reduces diselenides to afford selenols, which can be either isolated or treated in situ with alkyl halides to produce alkyl selenides or with epoxides to give β-hydroxyselenides.

  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。
• Active Metallic Indium-Mediated Ring-Opening of Epoxides with Diphenyl Diselenides: A Novel One-Pot Synthesis of β-hydroxy Selenides in Aqueous Media
  作者：Xian Chen、Huayue Wu、Weike Su、Rong Xu、Miaochang Liu、Jinchang Ding

  DOI：10.3184/030823407x218011

  日期：2007.6

  An efficient and simple one-pot procedure for the synthesis of β-hydroxy selenides in aqueous media through highly regioselective ring-opening of epoxides with diphenyl diselenide in the presence of active metallic indium is described.

  介绍了在活性金属铟存在下，通过环氧化物与二苯基二硒化物的高区域选择性开环，在水介质中合成 β-羟基硒化物的高效、简单的单锅程序。
• A Convenient Procedure for the Preparation of Organic Selenides
  作者：Makoto Sakakibara、Kazuhiro Katsumata、Yoshihiko Watanabe、Takeshi Toru、Yoshio Ueno

  DOI：10.1055/s-1992-26116

  日期：——

  Treatment of diphenyl diselenide with tributylphosphine in an alkaline medium forms phenylselenolate ion which converts alkyl halides, α,β-unsaturated ketones, and epoxides into alkyl selenides, (phenylseleno)alkenones, and β-(phenylseleno) alkanols, respectively, in high yield. Selenation of 3α-bromocholestane gives 3β-(phenylseleno)cholestane with complete inversion of the configuration.

  二苯二硒与三丁基膦在碱性介质中反应形成苯基硒负离子，该离子能够将烷基卤化物、α,β-不饱和酮和环氧化物转化为烷基硒化物、（苯基硒）烯酮和β-（苯基硒）烷醇，且产率较高。对3α-溴胆甾烷的硒化反应可得到3β-（苯基硒）胆甾烷，并且配置完全反转。
• Preparation of the First Bench-Stable Phenyl Selenolate: an Interesting “On Water” Nucleophilic Reagent
  作者：Claudio Santi、Stefano Santoro、Benedetta Battistelli、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1002/ejoc.200800869

  日期：2008.11

  In this communication we report the synthesis and the characterization of the first solid and air-stable selenolates, starting from commercially available phenylselenenyl halides and elemental zinc. These reagents were efficiently employed in the ring opening of epoxides as well as in other nucleophilic substitution and addition reactions showing an unexpected rate acceleration in water suspension

  在这篇通讯中，我们报告了第一个固体和空气稳定硒醇盐的合成和表征，从市售的苯基硒基卤化物和元素锌开始。这些试剂有效地用于环氧化物的开环以及其他亲核取代和加成反应，在室温下在水悬浮液中显示出意外的速率加速。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)