2-(3-Phenylselanyl-prop-2-ynyloxy)-tetrahydro-pyran | 148367-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(3-Phenylselanyl-prop-2-ynyloxy)-tetrahydro-pyran
• 英文别名: 2-(3-Phenylselanylprop-2-ynoxy)oxane
• CAS: 148367-28-6
• 化学式: C₁₄H₁₆O₂Se
• 分子量: 295.24
• InChiKey: ZLGSPTXMLIYHLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  394.7±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-Phenylselanyl-prop-2-ynyloxy)-tetrahydro-pyran 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 以55%的产率得到2-((E)-2,3-Dibromo-3-phenylselanyl-allyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  HYDROALUMINATION AND BROMINATION OF 1-(PHENYL-SELENYL)-1-ALKYNES

  摘要：

  Hydroaluminuation and bromination of 1-(phenylselenyl)1-alkynes were studied and compared with the rate of hydroalumination and bromination of the corresponding alkynylsilanes.

  DOI：

  10.1081/scc-100105675
• 作为产物：
  描述：

  苯基氯化硒 、 哌喃 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 2-(3-Phenylselanyl-prop-2-ynyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  HYDROALUMINATION AND BROMINATION OF 1-(PHENYL-SELENYL)-1-ALKYNES

  摘要：

  Hydroaluminuation and bromination of 1-(phenylselenyl)1-alkynes were studied and compared with the rate of hydroalumination and bromination of the corresponding alkynylsilanes.

  DOI：

  10.1081/scc-100105675

文献信息

• Hydroalumination of selenoacetylenes: a versatile generation and reactions of α-aluminate vinyl selenide intermediates in the highly regio and stereoselective synthesis of telluro(seleno)ketene acetals
  作者：Palimécio G. Guerrero、Miguel J. Dabdoub、Adriano C.M. Baroni

  DOI：10.1016/j.tetlet.2008.04.072

  日期：2008.6

  (Z)-butylseleno vinyl alanates intermediates which were captured with C4H9TeBr furnishing the (E)-telluro(seleno)ketene acetals exclusively. The isomers with opposite stereochemistry (Z)-telluro(seleno)ketene acetals were obtained by the reduction of phenylseleno acetylenes with lithium di-(isobutyl)-n-butyl aluminate hydride (Zweifel’s reagent) followed by reaction of (E)-phenylseleno vinyl alanates intermediates

  丁基硒炔乙炔与DIBAL-H的氢铝化反应，然后添加原位生成的（Z）-丁基硒代乙烯基丙二酸酯中间体，用C 4 H 9 TeBr捕获的正丁基锂，专门提供（E）-碲基（硒代）乙烯酮缩醛。通过用二（异丁基）-正丁基铝酸氢化铝锂（Zweifel试剂）还原苯基硒基乙炔，然后使（E）-苯基硒基乙烯基化合物反应，可获得具有相反立体化学（Z）-碲（硒基）乙烯酮缩醛的异构体用C 4 H 9 TeBr丙酸酯中间体。
• Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes
  作者：Lothar W Bieber、Margarete F da Silva、Paulo H Menezes

  DOI：10.1016/j.tetlet.2004.02.042

  日期：2004.3

  Diphenyl diselenide reacts with terminal alkynes at room temperature in DMSO in the presence of catalytic amounts of copper iodide to give good to excellent yields of alkynyl phenyl selenides. The reaction occurs under neutral conditions and the solvent acts as the oxidant. Diphenyl disulfide and ditelluride undergo the analogous reaction, but require the presence of a weak inorganic base. (C) 2004 Published by Elsevier Ltd.
• Cryptand-22 as an efficient ligand for the copper-catalyzed cross-coupling reaction of diorgano dichalcogenides with terminal alkynes leading to the synthesis of alkynyl chalcogenides
  作者：Elmira Mohammadi、Barahman Movassagh

  DOI：10.1016/j.tetlet.2014.01.088

  日期：2014.2

  A general and efficient method for the cross-coupling reaction of diorgano dichalcogenides with terminal alkynes using copper iodide/cryptand-22 (CuI/C22) has been developed. This protocol gave allcynyl chalcogenides in moderate to excellent yields in the presence of K3PO4 as the base under aerobic conditions. (C) 2014 Elsevier Ltd. All rights reserved.