2-(Butylselanylmethyl)-3-(furan-2-yl)-3-hydroxypropanenitrile | 1156004-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(Butylselanylmethyl)-3-(furan-2-yl)-3-hydroxypropanenitrile
• CAS: 1156004-09-9
• 化学式: C₁₂H₁₇NO₂Se
• 分子量: 286.232
• InChiKey: JZPREOOXIZTVAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(Butylselanylmethyl)-3-(furan-2-yl)-3-hydroxypropanenitrile 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 生成 2-(furan-2-yl(hydroxy)methyl)acrylonitrile
  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：

  糠醛 、 正丁基锂 、 丙烯腈 在 selenium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以72%的产率得到2-(Butylselanylmethyl)-3-(furan-2-yl)-3-hydroxypropanenitrile
  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