2-((Butylselanyl)methyl)-3-hydroxy-3-phenylpropanenitrile | 1156004-00-0

• 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-((Butylselanyl)methyl)-3-hydroxy-3-phenylpropanenitrile
• 英文别名: 2-(Butylselanylmethyl)-3-hydroxy-3-phenylpropanenitrile
• CAS: 1156004-00-0
• 化学式: C₁₄H₁₉NOSe
• 分子量: 296.271
• InChiKey: YVCIINJMTZJLRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((Butylselanyl)methyl)-3-hydroxy-3-phenylpropanenitrile 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 生成 苯丙腈,b-羟基-a-亚甲基-
  参考文献：
  名称：

  Lithium butylchalcogenolate induced Michael-aldol tandem sequence: easy and rapid access to highly functionalized organochalcogenides and unsaturated compounds

  摘要：

  Lithium "butylchalcogenolates are generated in situ by reacting the elements (S, Se, and Te) with (n)butyl-lithium at 0 degrees C. Reaction of the lithium alkylchalcogenolates with activated alkenes and aldehydes gives the corresponding aldol adducts. The selenium-containing products give Morita-Baylis-Hillman adducts after the oxidation/elimination of the selenoxide. The whole sequence can be performed in a one-pot procedure. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.158
• 作为产物：
  描述：

  正丁基锂 、 苯甲醛 、 丙烯腈 在 selenium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以95%的产率得到2-((Butylselanyl)methyl)-3-hydroxy-3-phenylpropanenitrile
  参考文献：
  名称：

  Lithium butylchalcogenolate induced Michael-aldol tandem sequence: easy and rapid access to highly functionalized organochalcogenides and unsaturated compounds

  摘要：

  Lithium "butylchalcogenolates are generated in situ by reacting the elements (S, Se, and Te) with (n)butyl-lithium at 0 degrees C. Reaction of the lithium alkylchalcogenolates with activated alkenes and aldehydes gives the corresponding aldol adducts. The selenium-containing products give Morita-Baylis-Hillman adducts after the oxidation/elimination of the selenoxide. The whole sequence can be performed in a one-pot procedure. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.158

文献信息

• Metallic chalcogenolates mediated modular Michael-aldol cascade reaction: an easy route to multi-functionalized chalcogenides and Morita–Baylis–Hillman adducts
  作者：Bruno A. Sousa、Arthur F. Keppler、Rogério A. Gariani、João V. Comasseto、Alcindo A. Dos Santos

  DOI：10.1016/j.tet.2012.09.027

  日期：2012.12

  Chalcogenolate mediated Michael-aldol cascade reactions consists of a very efficient route to multi-functionalized gamma-hydroxichalcogenides. Although, when selenolates are employed, these gamma-hydroxichalcogenides can be readily converted into the corresponding Morita-Baylis-Hillman adducts by oxidative elimination of the selenium moiety. In this context, herein we present a complete study on the scope and limitations of this reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• Lithium butylchalcogenolate induced Michael-aldol tandem sequence: easy and rapid access to highly functionalized organochalcogenides and unsaturated compounds
  作者：Artur F. Keppler、Rogério A. Gariani、Danilo G. Lopes、João V. Comasseto

  DOI：10.1016/j.tetlet.2009.02.158

  日期：2009.5

  Lithium "butylchalcogenolates are generated in situ by reacting the elements (S, Se, and Te) with (n)butyl-lithium at 0 degrees C. Reaction of the lithium alkylchalcogenolates with activated alkenes and aldehydes gives the corresponding aldol adducts. The selenium-containing products give Morita-Baylis-Hillman adducts after the oxidation/elimination of the selenoxide. The whole sequence can be performed in a one-pot procedure. (C) 2009 Elsevier Ltd. All rights reserved.