oct-1-yn-1-yl(phenyl)selane | 81699-87-8

• 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: oct-1-yn-1-yl(phenyl)selane
• 英文别名: Oct-1-ynylselanylbenzene
• CAS: 81699-87-8
• 化学式: C₁₄H₁₈Se
• 分子量: 265.257
• InChiKey: YLPBLEJHSVINIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  334.7±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  oct-1-yn-1-yl(phenyl)selane 在 水 、 二异丁基氢化铝 作用下， 生成 (Z)-1-phenylseleno-1-octene
  参考文献：
  名称：

  Synthesis of ketene butyltelluro(phenylseleno)acetals by the Al/Te exchange reaction

  摘要：

  Hydroalumination of acetylenic selenides occurs, regiospecifically and the vinyl alanes obtained as intermediates were transformed into ketene butyltelluro (phenylseleno) acetals by the Al/Te exchange reaction using C4H9TeBr as electrophile. The stereoselectivity of the hydroalumination of chalcogeno acetylenes was confirmed by performing the hydrolysis of the vinyl alane intermediates that results in formation of the correponding Z phenylseleno alkenes with good yields.

  DOI：

  10.1016/0040-4039(95)02333-x
• 作为产物：
  描述：

  1-bromo-1-octyne 、 二苯基二硒醚 在 Cu/Al₂O₃ 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以83%的产率得到oct-1-yn-1-yl(phenyl)selane
  参考文献：
  名称：

  氧化铝负载的Cu（II）催化的炔基溴化物和二苯基二卤代二氧杂环己烷的合成炔基硫属元素化物（硒化物和碲化物）的有效且通用的程序

  摘要：

  在锌粉或溴化铟（I）的存在下，氧化铝（Al 2 O 3）负载的铜（II）有效催化炔基溴化物与二苯基二硒化物和二碲化物的反应，从而提供相应的炔基硒化物和碲化物。已经解决了多种取代的炔基溴的反应。裂解二苯硒化物/碲化物需要锌粉或InBr。建立了反应机理。产品的产率很高，并且催化剂被回收。

  DOI：

  10.1016/j.tet.2012.08.046

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。
• Alkynyl phenyl selenides as convenient precursors for the synthesis of stereodefined trisubstituted alkenes
  作者：Marco Tingoli、Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Giancarlo Pelizzi、Alessia Bacchi

  DOI：10.1016/0040-4020(95)00153-y

  日期：1995.4

  the corresponding trisubstituted alkenes in which the tosyl group has been selectively substituted by an aryl or an alkyl group with retention of configuration. Finally, the cross coupling reaction of these vinyl selenides with methylmagnesium bromide, in the presence of a nickel catalyst, occurs with retention of configuration and affords the selenium free trisubstituted alkenes.

  加入p -toluensulfonic酸炔基苯基硒化物是区域选择性和立体有择的，并得到（Z）-α-（phenylseleno）乙烯基p以良好的收率-toluensulfonates。从这些化合物与卤化镁的反应获得α-（苯基硒代）乙烯基卤化物。（Z）-α-（苯基硒代）乙烯基对甲苯磺酸酯与氰基癸酸酯的反应提供了相应的三取代的烯烃，其中甲苯磺酰基已被芳基或烷基选择性地取代，并且保留了构型。最后，在镍催化剂的存在下，这些乙烯基硒化物与甲基溴化镁的交叉偶联反应在保留构型的情况下发生，并提供了无硒的三取代烯烃。
• THE REACTION OF TERMINAL ALKYNES WITH THE REAGENT PREPARED FROM BENZENESELENENYL BROMIDE AND SILVER NITRITE. NOVEL EFFICIENT SYNTHESIS OF 1-ALKYNYL PHENYL SELENIDES
  作者：Takashi Hayama、Shuji Tomoda、Yoshito Takeuchi、Yujiro Nomura

  DOI：10.1246/cl.1982.1249

  日期：1982.8.5

  1-Alkynyl phenyl selenides were synthesized in good yields by the reaction of 1-alkynes with a new reagent prepared from benzeneselenenyl bromide and silver nitrite.

  通过 1-炔烃与由苯硒基溴和亚硝酸银制备的新试剂反应，以良好的收率合成了 1-炔基苯基硒化物。
• Cu(I)-CATALYZED REACTION OF TERMINAL ALKYNES WITH PHENYL SELENOCYANATE IN THE PRESENCE OF TRIETHYLAMIME. SYNTHESIS OF ALKYNYL SELENIDES¹
  作者：Shuji tomoda、Yoshito Takeuchi、Yujiro Nomura

  DOI：10.1246/cl.1982.253

  日期：1982.3.5

  Treatment of terminal alkynes with phenyl selenocyanate in dichloromethane in the presence of CuX(X=CN or Br) and triethylamine at room temperature gave 1-phenylseleno-1-alkynes in high yields.

  在室温下，在 CuX（X=CN 或 Br）和三乙胺的存在下，在二氯甲烷中用硒氰酸苯酯处理末端炔以高产率得到 1-苯基硒基-1-炔。
• 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.